So back to trying out the V-string we wen out to a bar in the next town I dressed in a short black skirt 4 in heels tight top no bra and a black thong. Nikki in a very short flirty blue skirt push up bra with a pair of very expensive breast forms they look so natural the bounce and nipples even when you lean in for a hug there is no way you can tell they are fake, she then put on a nice silk button up top and under the skirt just the v-string, Once in the bar we walked around a bit then we decided to go sit at the bar, as we did Nikki made sure that a couple of guys were looking our way as she sat down her legs spread a bit and we knew right away that the v-string worked because a couple guys jaws just dropped at the sight of Nikki's nicely trimmed pussy. The came right over and asked to dance, we went out to the dance floor and Nikki pulled up her skirt just enough to give them both another look this time closer and they both were getting pretty worked up, after a couple of dances we went to the ladies room and Nikki said she could tell Steve was pretty turned on and said she wanted some cum she was really turned on. we went out to talk with Steve and Mark and offered our usual Blow job and that would be all they would get. WIth out hesitaion they both agreed and we went out to the parking lot and got between our car and a van Nikki started to suck on steves cock and he was moaning I took Marks I watched as Nikki took all of Steve's 7 in cock down here thoat Mark was about 6 in and I had no problem with that tool Nikki said she wanted both of them to cum in her mouth so as soon as Mark was getting close I switched and took over on steves tool shortly I heard Mark gasp as he shot his entire load down Nikki's throat she was moaning the entire time. Then I stood up and let Nikki finish off Steve and she did not spill a drop we then said our good byes the whole time turning down the invite back to there place.

We got back home and said test complete, Nikki was so hot, she went down on me and ate my pussy til I came twice, I said I have a new toy for you and pulled out a 6 in dildo, I told her to het on her knees I lube up the dildo and her ass and slid the dildo in and fucked the ass for all it was worth.

Afterwards we layed there and Nikki said she wished she could get a real cock in her ass but she wanted a straight guy she wanted to keep the illusion going but new that could never happen the only way was to have a guy that was into TV's or cross dressers. with that on our minds we went to sleep.

The next week end I called home and told Nikki to dress to impress, I had a surpprise I was bringing home, she said what I said you know Jeff from work, She said no way if it gets out that I am not a woman, it will be the end for me, I said don't worry he will never find out trust me and besides you flirt with him all the time, She said I know but he thinks I am all woman, I said just be ready got to go he's walking over to my car and I hung up.

When we got back to our place Jeff was pretty excited, I have to admit i was telling him the whole way home that if he played his cards right tonite he would be fucking both Nikki and myself, We walked in and Nikki was in a short red velvet skirt red thigh highs and red patton 4 in heels and a very tight top, Jeff said holy shit you are beautiful and sexy as hell. I said Nikki would you get Jeff a drink I am going to go change, a few minutes later I came out in at white teddy and matching thong with white thigh highs and 4 in white patton heels, Jeff's jaw dropped and I said I am sure you can use that mouth for something else and walked over to him and kissed him nice and deep, he slid his hand down between my legs and pressed his middle fingure into my pussy lips just a little bit my thong was already pretty wet and he noticed it and said my god this could be the greatest day of my life, I said most likely will be first a couple ground rules if you play by them I can assure you this will be the greatest day or night you have every had and maybe will every have,

With out hesitation he aggreed, I said ok so we are in charge, there is not going to be any beating or anything like that we just have a plan of how we wanted this night to go, he said so you have been planning this, I said well mostly Nikki has been wanting this for a while he turned to her  and she walked up and kissed him deeply, with that he said ok anything I will do anything, I said ok follow me I grabbed him by the hand and led him to the bedroom, I told him to strip, he did as fast as I have every seen. I then laid down on the bed and told him to pull my thong off, he did just a fast, I said now you are going to eat me til I cum and Nikki is going to suck you cock till you blow your load in her mounth he looked over and she smilled at him I figured if he was eating me he would not have a chance to feel up under Nikki's skirt, he started eating me and he was really good at it I was afraid I may cum before he shot his load in Nikki's mouth, but luckly she has gotten really good and in no time at all he let out a moan and shot his load, then he brought me off and it was awesome.

I then had him lay down on his back and pulled out some restraints and bound his hands and feet then pulled out a blind fold and coverd his eyes. I then got up on top of him and impaled myself on his 8 in cock and started to fuck like i haven't fucked in months it was so good I was screaming and he was moaning, Nikki got into the action by kissing him nice and deep. Jeff kept saying oh fuck, oh fuck your pussy feels so fucking good, once I came again he cock was good and wet I said how would you like to fuck Nikki in the ass, he said oh please I have wanted that ass for so long and with his hands and legs bound and his eyes covered there was no way of him knowing, he would think the sting from the v-string was from her thong and the v-string would keep everything in place and the hair from it would make Jeff just think its all real, with that I added some lube to Nikki's ass and a little to Jeff's cock and then Nikki got up and I help ease his cock into Nikki's ass I took a little bit but once the head popped in Nikki started to move up and down each time getting just a little more of his cock deeper in her ass.

After a few minutes Nikki had all of Jeff's cock up her ass she sat there not moving letting her ass adjust, Jeff was going crazy saying oh god your ass is better than I ever imagined, I looked at Nikki's face and she was competely in the moment shear joy, I pulled on her hips to get her to move and when I did she looked like she was going to explode, after a few minutes she was riding the full lenght of Jeff's cock and since he had shot his load down her thought minutes earlier Nikki was able to have her ass fucked for quite some time each time she came down a little harder and faster until she was fucking him so hard he would bounce a couple of inches off the bed. Finally he yelled he was coming and with that Nikki came all the way down shoving his cock as far as it would go into her ass, I said well cum she wants you to cum in her ass, he said oh shit and came, Nikki sat there feeling every pulse and evey shot of cum shoot up her ass she sat there until his dick went completely limp then she slid it out and

rolled onto the floor, Jeff was panting as like he had just had and incredible workout, I knelt down and kissed Nikki and said how was if for you. she was panting also and said that was the most amazing thing I have ever done, I said you should go clean up and pointed that she should get dressed I will take care of Jeff, I took off the blind fold and said thank you she has wanted her ass fucked for along time, then I took off his restraints and then told him that he would have to go, he got dressed and as he walked to the door Nikki cam back out and this time she had a lace out fit on so you could see what Jeff thought was her pussy to even futher create the illussion, Nikki walked up to him and said thank you for fucking my ass, Jeff said anytime just ask. Nikki smiled kissed him and said I may just take you up on that,

Jeff left and I walked over to Nikki and gave her a kiss and said see surprise.

I said see now we can get you as much cum as you want and get you ass fucked anytime.

she smiled and said you really are my best friend.

            The more we drank the faster time went by and next thing I knew the bar was closing.  Ginger said, “Why don’t you come over to my place and we can continue this conversation?”  This usually doesn’t happen to me and I really didn’t know how to respond.  I said, “Sure, why not?”  So, we got up from the bar and went out to our cars and I followed her to her place.  When we got to her place she invited me in and told me to have a seat and relax while she fixed me a drink.  So, I went over to the sofa and sat down.  Her living room was very unique in how it was set up.  There was a metal pole behind the couch that was bolted to the ceiling and the floor.  The couch was firm but comfortable and the ambiance was very comforting.  Ginger brought me my drink and sat down beside me.  She was very soft spoken and when she talked she had a special way of making me feel good.  I was really starting to loosen up now as Ginger leaned in to kiss me.  Wow!  It was so soft and passionate.  I had never been kissed like that before.  She slowly slid up on my lap as she kissed me and wrapped her arms around my head kissing me more and more vigorously and passionately.  Things were really starting to heat up when the doorbell rang.  She said, “excuse me” and jumped up to answer the door.  Talk about depressing, things like this don’t happen to a guy like me everyday.

            She went over to the door and opened it far enough to see who was there.  I could hear a couple of ladies outside and she let them in.  They were both very beautiful also.  She invited them in and they came over and sat on the sofa next to me.  She introduced the blonde as Jessica and the Asian as Mia.  Stupid me said, “hi, I am really excited to meet you.”  They giggled and said, “We can tell” as they were starring at my pants.  I definitely was starting to get really excited.  Ginger said, “You seem really depressed tonight so I thought I would invite a couple of friends over and see if we could cheer you up.  Grinning from ear to ear I said, “It is working, you are definitely starting to cheer me up.”  Ginger went and got some more drinks while I got to know Jessica and Mia.  When Ginger returned Jessica and Mia were sitting on each side of me rubbing my shoulders.  I was in heaven.  We drank a few more drinks and I was feeling really good when Ginger said, “we want to entertain you and make you feel good.”  I said, “I am game, how are you going to entertain me?”  They told me to sit back and relax while they went into the bedroom to change. 

            A few minutes later the stereo kicked on and the girls came dancing out of the bedroom in some really sexy lingerie.  They were hot as they danced there way over to me.  Ginger came over in front of me and started doing a strip tease while Jessica and Mia dirty dancing with each other.  I was really excited now and couldn’t wait to see what else was in store for this night.  Ginger slowly grinded her ass up against my crotch making my cock rock hard.  When I put my hands on her back she turned around, took my shirt off, and put my hands behind head and hand cuffed me to the pole behind the sofa.  This was very odd, kind of scary, yet interestingly exciting.  She went back to her strip tease striping down to her panties.  She had the most firm and perfect tits I had ever seen.  She danced her way on to my lap grinding her ass on my crotch the whole time and then she smothered me with her tits before allowing me to gently suck on each perfect nipple. 

            Meanwhile Jessica and Mia were undressing each other.  Kissing and seductively caressing each other as they went.  This was the most exciting moment of my life.  Three hot women dancing and taking their clothes off for me, what more could a man ask for?  Wow, life just couldn’t get any better than this.  All three of them were stripped down to their panties and they were starting to take my pants off.  First one leg and then the other. Then they took off my socks and my boxers.  I was rock hard and ready to explode.  This really turned them on and they told me that seeing me like this really made them wet.  Then Ginger says, “I want you to wear this blind fold while we prepare to rock your world.”  I agreed and she put it on.  Now I can’t see and I can’t move my hands.  For some odd reason this excited me even more.  Next I felt one of the girls slowly start caressing my cock and playing with my balls.  Mia straddled my chest and put her tits in my face and allowed me to suck on her nipples while she whispered in and nibbled on my ears.  Then I felt Ginger join Jessica.  Kneeling between my legs she spread them wide open and started to lick my cock.  It was perfect, two beautiful women licking and playing with my cock while a third was smothering me with her tits and nibbling on my ears.

            Gingers voice was so sexy and soothing when she talked and she constantly talked to me letting me know what was going on as she was doing things.  I felt so relaxed with her and she knew it.  She started to lick my ass while Jessica sucked on my cock.  At first it felt kind of strange and then she put some lubricant on her finger and slowly started putting it in my ass.  She told me to let her know if she hurt me.  I had never had anyone play with my ass before so I wasn’t used to it.  She was very gentle as she slid it in very slowly.  She kept working on my ass slowly getting up to three fingers sliding in and out of my ass.  After the pain of the initial stretching it started to feel real good and got me even more excited.  Next, I heard a vibrating noise and Ginger said, “This will help relax your asshole.”  I didn’t really pay attention because I was deeply into Mia now as we were making out passionately.  Ginger kept working my ass with the vibrator, while Jessica was giving me the greatest blow job of my life stopping periodically to keep me from cumming, and Mia had her tongue deep down my throat playing tonsil hockey.  I wished my hands were free so that I could get more physically involved, touching and caressing them. 

            With that said, Mia stops kissing me and I feel her turn and look at Ginger and Jessica.  They all three giggle and Mia asks, “how would you like to lick my wet juicy pussy?”  I say, “I have been looking forward to that ever since you walked through the door.”  Ginger asks, “Has anyone ever fucked you in the ass with a strap-on before?”  I say, “no, but right now I am willing to give it a try.”  They all giggle again.  Ginger tells Jessica to go down on my cock while she slowly slides the strap-on in my ass.  She says it will make me forget about any pain I might feel.  She was right to; I didn’t feel a thing as she slid it in.  Meanwhile, Mia says, “open your mouth wide and stick your tongue out so I can stick my wet juicy pussy on it.”  As she grabs the back of my head, I start to notice that the strap-on feels kind of like a real cock and all of a sudden I feel a giant cock go in my mouth and touch the back of my throat.  Mia holds my head while I gag on it for a second.  Then she starts moving my head up and down on it while she fucks my face. 

            I tried to grab her with my hands and pull her cock out of my mouth but my hands were cuffed and I couldn’t get free.  I felt violated but, at the same time it excited me even more.  Every time Ginger would ram her cock in my ass, my cock would go deeper in Jessica’s mouth.  Pretty soon they all had a really good rhythm going.  Everyone was fucking or sucking something and I was fucking, sucking and being fucked.  The passion and moaning got very intense and lasted for quite a while.  Ginger and Mia started fucking me faster and harder and Jessica started massaging my balls as she sucked harder on my cock.  All of a sudden Ginger rammed her cock as deep in my ass as she could and held it there as I felt her hot cum ooze from my ass around her cock.  Mia grabs the back of my head and shoves her cock down my throat and I feel her hot cum coat the back of my throat causing me to fire mine down Jessica’s throat.  I had never felt anything so intense before in my life.  As everyone relaxed from the intense moment, Jessica says, “open your mouth, it is my turn to surprise you.” 

On that note Mia took off the blind fold and got out of the way.  Jessica climbed up on the sofa and straddled my chest.  Now, I could see what was coming.  She had one of the biggest cocks I had ever seen.  As she went to put it in my mouth I closed it and shook my head saying there is no way you are going to put that massive thing in my mouth.  Jessica said, “Shut up bitch and open up.  You are going to suck my cock. You owe me after the blow job I gave you.”  Then she grabbed the back of my head with one hand and forced my jaw open with the other shoving her cock in as far as she could.  She violently fucked my face until she shot her massive load of hot sticky cum down my throat.

            All three of them sat on the sofa looking at me trying to see if I enjoyed it or not.  Ginger asked, “Well, did we rock your world or what?”  I was still in ecstasy and didn’t know what to say.  I just got a big shit eating grin on my face and said, “Now unlock these hand cuffs and let’s try that again with my hands free.”  They looked at each other smiled and unlocked the hand cuffs.  (To be continued)

I liked my share of porn, and as I had just gotten my first computer, I finally had the resources at my fingertips to do as much online porn surfing as a young man could handle.  And it was only a matter of time with all the stuff out there that I would stumble upon shemale porn.  I'd never seen anything like it.  Here were beautiful looking women, very feminine but instead of a pretty little pussy, there were these dangling cocks hanging between their legs.  I was utterly fixated, and I've been hooked ever since.  Don't know what it is, but there's just something about t-girls that completely fascinate me.

So I would look at the pretty shemales from time to time, jack off, and wonder what it would be like to be with one for real.  Well, this went on for a couple of years, just looking at the online stuff and continuing to date real, genetic women.  But then I entered a period where I wasn't seeing anyone regularly, and my fantasies about shemales began to become even more fixated.  

I had just joined an online site for dating, and it was a little more risque than the usual dating site, almost a bit "swingerish" in some respects.  There would be gatherings and all kinds of sexuality getting thrown around, althought to be honest, I didn't participate in much of that, though I did go on a few dates, and did manage to get lucky a few times.  Well, one night I'm perusing the chat room on the dating site, and it's the same ol' usual dialogue, until a new person logs in.  I certainly didn't recognize the name, but her quick profile read that she was a woman, so of course I immediately clicked on her name gaining access to her full profile.  

I of course click on her photo album first, and wham!  What do I see but a picture of her with a big ol' cock hanging between her legs.  Dear lord, she was a shemale!  And furthermore, she was absolutely gorgeous.  I looked around her profile, and she seemed pretty cool.  She was articulate, funny and wow, very sexual.  She also must've liked to have a good time because she mentioned that she liked to "smoke".  So I'm thinking, "great, she's a pothead".  Oh well, can't have everything right?  Not like I'm looking to get married anyway, so in any case...

I'm a little nervous to strike up a conversation with her because I know many people in the chatroom, and honestly, I didn't want to give anyone the impression that I was some kind of tranny chasing weirdo!  Hey, call me what you want, but I'm thinking most of you would understand my predicament, especially considering how new I was to the whole thing.  But eventually, we do exchange pleasantries, and I end up just writing her specifically, and having a message delivered to her profile.  To my luck, she writes me back and says that she likes my profile and is definitely interested.  Wow, my mind was blown, and all of a sudden, I started getting a little nervous that I was actually maybe gonna do something about my shemale fascination.

We go back and forth on the site's messaging system for a bit before trusting each other enough to exchange emails, and then eventually phone numbers.  I was especially hesitant because I feared she would call and one of my roomies would answer the phone, giving away this "double life" I was leading.  But thankfully, I never had any problems, and when i got a cell phone, that prevented any possible problems that may have created.  But for a number of reasons, we just never actually set a date for getting together.  I was very nervous as this would be my first time with a shemale, but after several weeks, and a good phone conversation with her, I was at ease enough, and we made a date to get together that night.

She lived about a good half hour away, which would mean I'd have to do a bit of driving.  I thought that maybe a hotel would be good, but she was a little nervous about that, and we decided to have our first meeting at her place.  

I won't lie to you, I was still very, very nervous, but I was gonna go through with it.  I get myself cleaned up, run down the street and pick up some beer, wine and flowers, and off I go.  The whole drive to her place, my stomach is flipping and my mind is racing.  i can't even imagine what is in store for us, and if I will be able to actually even go through with anything even when I finally do get there, but soon enough I'm pulling up in front of her house, and I see her face poke out of a window.  Whew, nervous as hell...

I shuffle up her walkway and through the gate, hearing dogs barking as I ring the doorbell.  Soon thereafter, she answers the door.  I'll call her Valerie, and dear lord, she looks absolutely amazing!  She's even prettier, and more feminine in person.  She's wearing a lovely little flowery, red nightie that is mostly transparent, exposing much of her beautiful breasts.  She's wearing matching red fish-net garters, and I take a closer look and see that her panties are also quite see through, exposing her penis.  My heart is about to explode out of my chest, I'm not kidding.  I'm standing there wondering just what in the hell did I get myself into here.  But Valerie welcomes me inside, giving me a warm hug, although my worried self prevents me from truly embracing this beautiful creature standing before me.  Hey, I'm doing my best here!  She shows me around her house a little bit, and is very inviting.  I give her the flowers, and she chuckles a bit at the site of the beer and wine, saying that she doesn't drink, but she certainly appreciates the thought.  Well, it doesn't take me long to crack open the beer, and I'm actually a little thankful she doesn't drink, because I'm thinking I'm gonna have to polish this 6 pack off and rest my nerves!

We are soon in her bedroom, and I'm drinking my beer like it's going out of style, already polishing off 3 bottles in the first 20 minutes of our conversation.  Valerie is very inviting, very cool, relaxed and terrific in every way, but I just can't shake the nervous nellies.  It gets even worse when the conversation steers toward a sexual nature and my eyes keep drifting to her crotch, seeing her cock bulging out of her panties.  I think it's probably a good time to describe Valerie a little bit.  She's very feminine.  She has a very curvy little body, and probably stands about 5'5" tall.  She is a little Latin girl, and that only helps her femininity as it adds to her sexual ambiguity.  Her breasts are probably a perfect C cup, and she has lovely curly black hair, framing her beautiful eyes and lips.  Her fingers and toes are perfectly manicured, and her smile could light up a room.  Her voice is even quite feminine.  And it was all wrapped in a beautiful, honey brown skin.  

I sit on her loveseat, as she lounges on the bed, cracking open my 4th beer as we both light up a couple of cigarettes.  I feel my nerves easing a bit, but I'm still nowhere near ready to do anything sexual with this girl.  Thank God she was so good with newbies, and could carry a conversation.  But as our chat gets a little more sexual, she tells me to please get undressed as she'd like to get a better look at me.  I stand up and start unbuttoning my shirt as she looks on, continuing to chat, and then compliment me on my physique.  I can only giggle, and blush nervously.  I then pull off my shoes and socks, and start unbuckling my belt.  Her eyes never leave me, and my throat is dry.  My belt is unbuckled, and I unzip my pants.  She then slides off the bed and resumes my old spot on the loveseat, right in front of me.  I pull my pants down, and she slowly reaches through my fly in my boxers and starts stroking my cock, looking up at me, and making sexy talk.  I feel like I'm about to have a heart attack as she takes my cock into her mouth.  She sucks on my cock for a bit, and then asks me if I'm still nervous.  I reply that I am indeed still pretty nervous, and she asks me if I'd like to "smoke" with her.  I say sure, as maybe that will help me out nerves-wise.  

She reaches into her night table, and pulls out the stuff, and I notice right away that she is definitely NOT a pothead.  This is a completely different animal we're talking about here.  But as I said before, I like to experiment a bit with the party favors, so I'm going into this with an open mind.  Hey, frankly, it's nothing I hadn't done before on a couple of occasions, only this time, I'd be doing it in a sexual setting, and not a social, party kind of setting.  So she fixes herself up as a giant cloud of smoke wafts through her room and then gets everything ready for my toke.  I inhale nice and slow, and blow out an equally huge cloud.  And WHAM!!!  All of a sudden I am NOT nervous anymore.   

All of a sudden, I'm Chatty Cathy and pulling my underwear off.  I'm a sexual force and the feeling is absolutely incredible as all of my inhibitions go by the wayside.  Valerie and I chat for a bit more and she asks me if I'd like to see more of her.  Of course!  She pulls off her little nightie, fully exposing her gorgeous breasts.  My eyes are glued to this beautiful woman as she wiggles out of her panties, exposing her beautiful cock.  And I'm here to tell you, she has a BEAUTIFUL COCK.  She has a little trimmed patch of pubic hair directly above her cock, but the rest of her organ is perfectly shaved from her asshole, to her balls, to her shaft.  Smooth as a baby's bottom.  She resumes her spot in front of my cock, getting down on her knees this time and starts sucking on my cock as I feel myself getting hard in her mouth.  The feeling is incredible, and watching this beautiful shemale wrap her lips around my cock is about more than I can handle.  But I soon feel like I'm missing out a little bit, and I ask her if I can suck her cock.  Yeah, I'm not nervous at all anymore.  She stands up, and I kneel down in front of her dangling she-cock as I touch a cock other than mine, for the first time in my life.  Her cock feels so soft, and while it's much like my own, it's a completely different feeling touching someone else's cock for the first time.  I tell her this, and it only excites her that much more, knowing that I am a shemale virgin.  Her cock slowly grows in my hand as I begin to stroke it up and down before finally kissing it on the head.  Her cock jumps a little bit, and she sighs as I wrap my lips around her pretty cock.  Wow, I'm sucking a cock for the first time in my life, and it's absolutely wonderful.  I ask her periodically if I'm doing a good job.  Hey, I know what I like when a girl is giving me head, and you'd think as a man I would know how to suck a cock, but this IS my first time.  She tells me I'm doing great as my head bobs up and down on her beefy dick.  And yeah, it was a beefy cock.  As she got hard in my mouth, I could finally see just how big her dick was, and it was just the perfect size.  She was probably about 7 inches long, nice and thick, and very rigid.  Perfect!

I'm sucking her cock for a good 10 minutes or so, and by now she's reclining lazily on the loveseat, as we gaze into each other's eyes with my hungry mouth wrapped around her cock.  We move over to the bed and get into a nice 69 position.  She is laying on top of me feeding me her meat as I feel her perfect lips slide down my cock, getting hard in her mouth.  While sucking on her cock as she lays on top of me, I also get a nice view of her asshole.  I instinctively move my lips and tongue to her little hole and start licking.  I feel the vibration of her heavy moan as her mouth still sucks on my cock.  I ask her if she likes that, and she says yes, she loves it.  I keep licking her little asshole and tell her that I want her to fuck me.  She happily agrees!  As it is my first time getting fucked, I'm a tad nervous, but I'm so sexual at the moment, I long to feel her slamming into me, knowing that she'll be fucking my virgin ass.  I know she feels the same excitement knowing she'll be popping my cherry.  She figits around in her night table again, and tells me to take another hit off of the good stuff.  I happily oblige and get another heavy rush of euphoria.  Then she tells me about something called "rush".  I watch her as she gets a little bottle out from her night table and tab a cloth with whatever is in the little bottle.  She says it will help relax my asshole as she's fucking me, and will also make the entire episode that much more pleasurable.  Hey, who am I to turn down more pleasure?!?  She also inhales the vapors eminating from the little bottle and turns me over onto my stomach.  I feel her dab my asshole with lube as I take in my first breaths from the dabbed towel.  My head is spinning and everything feels so good.  And then.  I feel the head of her cock enter my virgin ass.  Wooooooooooowwwwwwww.  The feeling is INCREDIBLE.  She slowly starts fucking me doggie style and I feel her hands gripping my muscular ass as her hard cock pounds inside of my tight asshole.  She is grunting and moaning like an animal as I try to find her rhythm.  Soon I'm feeling so good, I'm talking dirty and meeting her hips in perfect unison with her pounding hips.  I reach behind her and grip her ass, forcing her deeper.  The feeling is just so good, i can't get enough.  I'm a total sexual animal, and I can't even begin to say how good it all feels.  Her pounding is causing us to slowly move from traditional doggie to my face being forced into her pillow as she just pounds at my asshole.  The towel is close and I take another breath as I feel her also taking another breath when she says that she's getting close to cumming.  I tell her I want to see her cum and as she pulls out, i flip over and her cock explodes all over me.  Her hot cum sprays on my chest, my neck and my face, a little bit hitting my lips.  The heat coming off of our bodies is extrordinary.  Our bodies are damp with perspiration and the room smells of sex.  

She grabs a towel and wipes it down my asscrack and asshole, cleaning me up a bit as I rub her cum into my skin, taking a nice long look at us in her mirrors.  That's one of the nice things about her bedroom, she has several large mirrors throughout the room and we can look around and see ourselves fucking and sucking in every position, and from every angle.  Very sexy I must say.

And now it's my turn.  I lay down on the bed as her head dives between my legs, sucking on my cock, getting me nice and hard again.  Doesn't take long, and I long to fuck her sweet ass.  Her ass really is a thing of beauty.  She's got that latin blood if you know what I mean, and I tell ya, her ass is a true blessing.  Nice and round, and very feminine.  Total J-Lo ass and perfectly smooth.  We lube up her ass and dab the towels a bit more from her little bottle of "rush", freshening it up.  We're on her bed, and she gets on her hands and knees, her asshole ready to be fucked.  I take a nice look at us in the mirrors and the scene is truly amazing. Looking down at her asshole, I squirt a healthy amount of lube all over her hole and on my cock before insertion.  I slowly slip my cock into her pretty little asshole and the feeling is amazing.  I've never had anal sex before, so this too is a brand new experience for me.  I inhale heartily from the dabbed towel and my brain catches fever turning every sensation into sheer pleasure.  And boy, it doesn't take long before I have to cum.  I'm watching her head sway, and her hair bouncing up and down.  Her ass meets my every thrust and it isn't gonna be long.  I hunker over her and start fondling her breasts and sucking on her neck as I feel my hot cum boiling in my balls.  I tell her I'm about to cum and she actually pushes her ass harder against my cock, preventing me from pulling out.  I feel my body quake as I heave into a tremendous orgasm.  My cock explodes into her ass, pumping stream after stream of cum deep inside her hole.  Wow, my head and body are spinning.  Our bodies are covered in perspiration and my cock finally slips free from her little asshole, a long string of cum dangling all the while, still keeping us connected.

She turns over and we kiss passionately, our tongues lapping at each other's still hungry mouths before she dismounts from the bed and makes a quick trip to the bathroom for a little cleaning up.  I follow her into the bathroom when she is finished and clean myself up a bit as well.  Soon we're both back in her bedroom, blowing some more smoke and talking the night away before another nice session of sucking and fucking.  She cums all over my face, and I leave a very, very happy young man.  It won't be our last time together, and she even goes so far as to tell me that I was one of her most incredible sexual experiences ever.  Trust me, the feeling was definitely mutual.  I'd love to share more experiences, and trust me, there are plenty, if anyone is interested, but I think this is  good stopping point for this first shemale experience.  Hope everyone enjoys it, and now, I've got to jack off.  Because reliving this experience has left me with quite a spot of precum on the front of my boxers.  I think I better take care of that! 

" Oh my god why don't you try to wear a top that fits you look like a cheap slut." She laughed and her friends joined in a half seconded behind her. She walked around the side of the car, luckily for me she didn't take her eyes of my tits. She grabbed my top and ripped it open the cold air hitting my boobs making my nipples errect. I stood there shocked not knowing what to do.

" Do you want me to kiss you?" she mocked as they all laughed

" Yes " the words fell from my mouth with out me knowing it.

"On my god you really are a little whore, all those rumours where true."

"Yes they are" she lent fowards and kissed me it was wonderful her lips where so soft. She stopped and looked at me shocked she looked down , my cock was rubbing against her leg. She stepped back stunned 

" She has a cock!!" she yelled as her three friends joined her " Hold her on the bonnett i want her."the girls held me there ripping my skirt from me, they prised my legs open as Kerry climbed up on top of me and lowered herself down onto my cock.

" what the fuck are you doing get off me" i yelled and tried to move but i was held down by the three other girls "get off, this is rape stop it please" she kept riding my huge cock her pussy was so wet and warm i couldn't help but moan with pleasure.

" She loves it listen to her, my god she is so big, ive never had one this big before it feels so good." Her thrusting got faster and faster before her orgasmic screams echoed around the alleyway as i sparayed my hot cum inside her. She dressed herself picked up my clothes and started to walk off before turning back to me. " Everybody is gonna know about you bitch, everyone is gonna know about your huge cock, you will be treated like the freak you are."

I ran back into Claire's clinic and burst into her office

" Please please im begging you please turn me back, take it away give me my pussy back."

" ok i will but seeing as you are my greatest work i wanna show you off to any of my pretential clients."

"yes ok i'll do it, i want to be me again, i so sorry for what ive did to you im so sorry."

" Well i hope you've learnt that you are a bitch and that you need to be nice" she held the door open for me "Go home and wait for me to call you, i'll orgainise some people who want to see my work and you can show off those lovly boobs."

I left the surgery praying that i would get my body back before Kerry told of my penis, i was just glad i was near the end of this weridness, but i knew there was another twist yet to come.

            Carefully rummaging through the drawer I selected a pair of lace covered bikini bottoms.  My cock was fully erect and begging to feel them.  Dropping my pants I pulled off my shirt and boxers and slowly slid them up my legs.  I savored their silky smoothness and was about to reach for the bra when a voice behind me said, “What are you doing?”

            I froze, horrified at being caught.  Slowly I turned around to face Sam.  I tried to think of something to say but could only manage a meek stammer.  Sam just stood there with her arms folded, staring at me.  Her eyes lingered on my erection and a devilish grin came to her face.

            “So you like to wear panties do you?” she asked.  “Well I think I’ve got something we can have some fun with.  Will you do that for me? After all you are wearing my panties.”  Not waiting for a reply she said, “Stand in the corner and don’t turn around.”  Silently I obeyed her.  She knew that I was going to be pathetically easy to control from now on.  As I faced the corner I could hear her going through drawers behind me.  Finally she commanded me to turn around.

            When I did I saw that she had laid out a slutty outfit on the bed.  It was a red lace thong with matching bra and garter belt, black lace-trimmed pantyhose, and three inch stiletto heels.  “Put it on Ray,” she commanded.  Slowly I lowered her panties to the floor and picked up the red thong.  As I pulled it on my erection sprang back to life.  “It would appear that you like this,” she commented.  “Hurry up with the hose and belt.”

            As quickly as I could I donned the garter belt and slid on the hose.  I’m on the swim team so I keep my body shaved and the hose felt incredibly rich against my smooth skin.  I hooked the garter belt straps to the hose and put on the bra.  Sam stepped over with some silicone pads and slipped them into the bra.  She ran her fingers through my shoulder-length hair (the one vice I’d allowed myself since I could tuck it up under swim cap).  “You look pretty in that whore’s outfit,” she said.  “Step over here please.”

            I sat on the stool so she could apply makeup, blush, eyeliner, mascara, and lipstick, feminizing my soft features to the fullest.  “Turn around, let me look at my whore.”

            I complied, twirling slowly so she could see her handiwork.  My hardon was standing out beside the thong and she gently squeezed the head.  She threw her arms around me and began kissing me.  She pulled her tank top over her head and guided my mouth to her bare breasts.  I sucked first one and then the other, rolling the nipples gently in my teeth.  Pushing me down on my knees she said, “Close your eyes.”  I did and waited patiently as I heard her unzip and slide out of her jeans.  When she commanded me to open my eyes I got the shock of my life.  Staring me in the face was a nine-inch erection.  I could only stare in disbelief.  She flexed it up and down, breaking my trance.

            “Do you like it?”  I nodded.  “Then kiss it, take it in your mouth.”

            Slowly I extended my tongue to the head of her cock.  I licked up a drop of pre-cum and savored its salty-sweetness.  I took the head into my mouth and began to slowly suck on it.  I could only take about six inches so I concentrated on that, wrapping my hand around the base of her shaft and jerking her into my mouth.  While I worked on her cock she was running her fingers through my hair and telling me that I was a good cocksucker. 

            Soon her breathing became ragged and she said, “If you’re not careful I’m going to cum in your mouth.”  My response was to increase my tempo, sucking her with a vigor I didn’t know I possessed.  Soon I was taking all of her into my mouth, working my swallowing muscles on her cock head while her balls slapped my chin.  Finally she could hold it no longer.  She came with a rush, shooting her load down the back of my throat.  I swallowed as fast as I could but it was more than I could handle.

            I continued sucking her cock until I had every last drop.  Then I let her go with an audible pop.  She smiled and leaned over to lick up the cum that had dribbled down my chin.  Then she kissed me.

            “Your turn,” she said and pushed me onto my back.  She grabbed my seven inch cock and parted her lips.  She plunged down the length of my cock, taking it all in at once.  I moaned softly as she expertly worked on my cock.  Her left hand held the base of my cock, her fingers lightly massaging my balls, and her right hand probed my ass.  The sensation of receiving a blowjob while dressed up like a cheap whore and having my ass finger fucked was too much.  With a loud groan I came, filling Sam’s mouth with my cum.  She drank all of it, and then moved up to kiss me.  She had saved a mouthful of my cum and she now shared it with me.

            Sitting up she licked her lips.  “Mmm…” she said, “that was fun, but I’ve got more to give you.”  Reaching down she stroked her fully revived nine inch cock a few times.  Pushing me onto my back she said, “I’m going to fuck you like the horny little slut you are.”

            Grabbing my knees she forced them up to my chest, completely exposing my ass hole.  Placing the head of her cock at the edge of my sphincter she paused to apply some personal lubricant.  Then she slowly pushed forward until the head of her cock disappeared into my ass, causing me to cry out in pain.

            Sam waited patiently until my ass had ceased to spasm around the head of her cock.  Then she began to move her hips back and forth, working deeper and deeper into me with every stroke.  When she had about half of her cock inside me she withdrew all but the head then in one smooth motion she pushed in all the way to the base of her cock.

            The pain was excruciating, but the intense feeling of pleasure was even greater.  Slowly Sam fucked my ass, sliding almost completely out, and then gliding back in one fluid motion.  I lost all track of time, intent only on the great fucking I was receiving.  Then we heard a voice say, “Well, well, well.  What do we have here?”  Sam and I turned as one to look.  Jan was standing in the door wearing one of those extremely short skirts and a red halter top.  Here I was dressed like a horny slut with my legs wrapped around a shemale buried up to her balls in my ass with my girlfriend looking on.  What a fix.

            “It looks like Sam found herself a slut,” Jan said while walking over to the bed.  Leaning in she kissed Sam deep and passionately.  Hiking up her skirt she dropped her panties to the floor.  Hopping up on the bed she straddled me and said, “I like fucking sluts!”  With that she plunged herself down on my shaft, causing me to gasp.

            The three of us fell into a frenzied rhythm of fucking.  It wasn’t long before Sam tensed up and unloaded her balls into my ass.  I in turn came inside of Jan who was busy riding me like a jockey.  She came also and the three of us collapsed together in a pile on the bed.  It was the single greatest life changing performance for any of us.

“Your mine sugar,” 

“Shake that arse for me baby,” and other demeaning harangues were yelled my way.  I was so scared about what would happen to someone like me in here.

One of the guards laughed “I’d get a big bad friend if I were you,”

His mate retorted “I’d get two big friends.”

I spent first night in Chelmsford alone in a cell, scared to death and didn’t sleep a wink.  The next day I was assigned a cell in the general population wing and my cellmate was ‘Big Bill Stevens’.  He gave me the some advice.

“Mike, you need a really, really big friend or two, otherwise those lads will eat you alive. Or should I say you will spend your life eating them!” he laughed.

Bill went on to explain prison life to me; how there were two types of inmates really; the hunters and the hunted.  With my small stature and my soft body, unused to any physical work, I was a sitting duck for the freaks.  I explained my background to Bill, about how I was a successful businessman who had the misfortune to drive home after consuming nearly a bottle of scotch.  About how I didn’t even remember hitting the girl.

“We all have our stories to tell,” said Bill, “and yours don’t mean shite in here.” He added callously.

“However,” said Bill, “there is another class of inmate.  The kind like you that has a lot of money on the outside; the kind that can buy protection; the kind that can get a get a guard or two in his hip pocket. Your kind.” He half laughed.

And that was it, the deal was struck. Big Bill Stevens became my minder.  With a liberal sprinkling of cash, which was provided by a bent guard to whom I set up a special account to access to my money outside, (and who took twenty five percent of every penny I had him withdraw); I was assigned to a larger more comfortable cell with Bill. We lived like kings; special food, special privileges, special packages from the outside containing booze, cigarettes, pornography, anything to make life more comfortable or anything that could be used for trade inside the nick.

I figured it was costing me more to live in jail than it was to live the high life outside, but I was locked up for five years with no hope of release, and without Bill as my minder, a few guards in my pocket, and the influence and protection of my money, life would be hell.

Then about three months ago, it all went to shit.  I found out there was another class of prisoner, a very special class of inmate who was so unique that there could be only one in each jail, the kind of inmate that ate the hunters just as easily as the hunted.  The kind of hard man that had nothing to lose, and was so hard the other kingpins in the nick paid him tribute and did his bidding without question.  The kind of inmate who didn’t need to bribe guards (although he kept them well paid anyway), because with one phone call to the outside he could have any guard’s family battered or worse.  The real boss of Chelmsford prison was not the Governor, It was Eddie McGuire, or actually, Mister McGuire to anyone but his closest confidants.

Eddie was in for life, but Eddie still ran one of the most successful criminal gangs on the outside.  Eddie wanted for nothing on the inside, the only thing he couldn’t have was freedom. And now Eddie had me!

Four month’s ago Eddie approached me and said he was impressed with how a faggot little man like me had set myself up.  He said he had no problems with the way I lived, as long as I bought my ‘special concessions’ from him, and as long as he got ten percent of any cash that I had smuggled inside.  From the look on Bill’s face I knew I had choice but to comply.  I figured it was just life in the nick and what the hell I had plenty of money working for me outside.

Then about a month after that I was sitting in the cell I shared with Bill wondering what was taking him so long to do the daily rounds of bribes and trading when I had an unexpected visitor.  One of Eddie’s minders came in to the cell and said,

“Bill won’t be back.  In fact he ain’t going anywhere any more.  When the fracas is over, you get your ass down to Eddie’s you little toerag.”

I wondered what the fuck he was on about, but next minute 2 prison officers came in and turfed me out. They searched the cell from top to bottom removing all my contraband and luxuries.

“You can go back in now arsehole.” One of the guards sneered. “Bill has had an accident and won’t be back.  You’re on your own until we re-assign you to another cell.  Sleep well sweetie!” The guard crooned and sauntered off.

I was scared shitless but knew better than to ignore the summons to Eddie’s cell.  I hurried down, minder-less for the first time since my arrival.  Eddie was waiting for me.  He was a slim man in his fifties, but sinewy with muscle.  I had heard he had choked more than one man to death with his bare hands.

Eddie wasted no time explaining the situation; Bill had been withholding some of the money I was supposed to pay Eddie.  Bill was now a permanent guest of the hospital and would never walk again.  Bill had fucked up big time.  And more importantly, Bill was my minder so I was responsible for his actions.  I tried to explain the situation; that I didn’t know Bill was skimming from the tribute I was supposed to pay.  Eddie quickly went on to explain that he didn’t give a fuck, that my girly ass belonged to him now.  I was going to become his accountant, his financial adviser, and I was going to pay him for the privilege of his protection.

I was moved into a cell next to Eddie that evening. What could I do? I had to have a minder otherwise I would be every hard man’s toy. I complied with Eddie’s wishes. I managed his funds and barter inside and I paid my tribute. After a couple of weeks I though I had nearly a better set up than before. Then some changes started to happen and at first I didn’t realise how drastically they would affect me.

Eddie had me organise some women’s clothing be bought in.  We had become sort of friendly; well as friendly as you could get as an underling; probably because a little chap like me was no threat to him.  He showed me some fashion magazines that he had bought in and pointed out some skirts, blouses, suits, and lingerie.  I have to say I was not suspicious at this stage, fashion mags in jail were poor mans porn that you didn’t have to hide them from the guards. I had also come to find out that some of the other effeminate inmates dressed as women and performed sexual favours for money. I also knew some of the more powerful prisoners had ‘wives’, crossdressed men who lived with them in their cells in homosexual relationships, either for protection or because they were just queer.  The guards turned a blind eye or took part of their take from the ‘working girls’; either way, I wasn’t really interested. 

I figured Eddie had me order in the clothing either to sell to the ‘working girls’ or he had his own ‘wife’ hidden away somewhere discrete in the jail.  I was really puzzled at how much interest he had me show in ordering the lingerie and shoes. He took special care in selecting sizes. Together we poured over the catalogues and I feigned interest as much as I could. I agreed with him that high heels looked lovely on a nice set of legs, but were hardly practical for a crossdressed inmate to get around the jail.

“You fucking nonce!” He laughed, his voice roughened from forty cigarettes a day. “She won’t be wearing them around the nick, just in my cell, and mainly on my cot.” He laughed again.

We spent ages looking at stockings and pantyhose.  He told me how much he loved nylons on a shapely leg and had me order in large quantities of fully-fashioned stockings and sheer to the waist pantyhose in many different shades.  I explained to Eddie that they would cost a fortune, as even the guards who were on the pad didn’t like prisoners having nylons because they were an ideal medium for suicide by hanging.  One or two inmates in the past had suicided by hanging themselves with a stocking.

“Just get on with the order, secretary!” he scowled.  “Just fucking pay the price! Just fucking do what your told!” 

I hated upsetting Eddie in any way as he scared me to death, and now I leapt to my feet to make the deal with the bent guards and pay their ridiculous prices for the smuggled in lingerie and other girly items.  Another thing I didn’t like was that for a week or so Eddie kept calling me his ‘secretary’ for some reason. I figured it related in some way to me being his accountant. 

Then the fateful day happened. Today!

I could walk around the jail with immunity now that I was ‘one of Eddie’s’.  I had sometimes seen other inmates point to me and I overheard them referring to me as ‘Eddie’s new secretary’.

“Oh yes, I can see what he sees in her.” One ‘noncer’ said, which I found puzzling.

It was just after dinner when I returned to my cell to find one of the prison ‘wives’ waiting for me.  I had seen him before and knew him as Craig, one of Eddie’s underlings.  I only just recognised him though as he made a quite attractive and convincing woman.

“Fuck off you poofter!” I shouted at him, her, It!  “Don’t you know who I work for!”

“Oh I know darling,” she cooed at me. “ And Eddie said it’s time.  You’re coming with me honey.   I’m going to prepare you for him.”

“What the fuck are you talking about,” I said.

“Look honey, my name is Carmel and I work for Eddie.  And you’re coming with me and I’m going to show you how to transform yourself for Eddie.” Carmel said calmly.

“I still don’t know what the fuck you are talking about.” I said

“Well honey is you look over your shoulder you will see ‘Iron Bar’ Steve.  You can either be transformed by him or by me ok?” Carmel crooned.

I turned around, and sure enough, there was ‘Iron Bar’, Eddies enforcer. He was grinning at me and slapping a piece of steel pipe in the palm of his hand.  I made my decision and nodded to Carmel who led me out of my cell down into E Block.  E Block was pretty much deserted and I had heard rumours that it was a part of the prison used by prisoners and guards alike for activities the general population didn’t need to know about.

Carmel led me into one of the bathrooms in block and turned into the small room where a big old white bath sat.  It was full of steaming soapy water.

“Strip and get in sugar,” Carmel said.

I looked around saw all manner of soaps, shampoos, razors and such.

“Fuck off hag fag,” I sneered at Carmel.

“Steve, she wants you!” Carmel yelled out the door, and sure enough there was ‘Iron Bar’ with a smirk on his face, smacking his trusty pipe into the other palm. Carmel pushed her face right into mine.

“You don’t seem to understand do you Mike? You either do exactly as I say, which is what Eddie wants; or, I let Steve there take you for the last walk you’ll ever have!”

I now realised the severity of the situation but was still confused. Although enough to do exactly what Carmel said or I would have my legs broken in such a way they would never mend.  I shucked off my clothes and lowered myself into the bath.  Carmel threw me a loofah and said “Scrub!” So I did.  Then she sat on the edge of the bath and took one of the disposable razors from a pack.  I was not surprised that one of Eddie’s ‘girls’ would access to an item that anyone else in the prison population could never get.

Carmel lifted my leg and stated shaving it.  I tried to pull my leg away and she held it tight, gave me a stern look, then glanced towards the door where Steve was lounging outside. I surrendered.

“Watch how I do this hon,” Carmel said,  “you doing this shit yourself from now on.”

Then it dawned on me what was happening, the significance of the word ‘transform’; the reason Carmel was shaving my legs.  I felt numb.  I couldn’t comprehend why Eddie would do this to me.  I was in a trance as Carmel fished shaving my legs and then the soft down on my arms.  She shaved my face and rubbed moisturiser onto it.  Then she led me out of the bath and dried me off.  I was just like a mannequin that Carmel could move around and pose as she liked.  Carmel led me to the part of the bathroom that had about ten sinks and mirrors lined up along the wall. It wasn’t until later that I took notice that the usual stainless steel mirrors had been replaced with glass and that each of the mirrors had a bright light over it.  One of the sinks had a high stool set up in front of it and Carmel sat me on it.

“Now pay attention honey, you need to learn how to do this,” she said.

I noticed that on the shelf below the mirror was a large assortment of makeup.  Carmel took a damp sponge and applied generous amounts of foundation to my face, cooing at how lovely my skin was and that I didn’t need to use 'dermablend' or other such heavy-duty foundation.  After she had applied the foundation to my face and neck she picked up brush and applied a slightly lighter coloured powder to set my face.  She rouged my cheeks, accenting my high feminine cheekbones.  She fussed around my eyes applying liberal amounts of eyeshadow, eyeliner, and mascara. She then finished with another light dusting of powder. All the time Carmel was explaining to me how I would need to learn how to apply my own makeup. I was still too dazed to really accept what was happening. The final touch was the application of a bright red nail polish to my toe and fingernails.

Then Carmel reached under the sink and opened a cupboard.  She pulled out three wigs sitting on wig stands and I noticed there were a lot more in there.  Carmel looked at me seriously for awhile then selected a blonde bob and pilled it on my head.  She turned me towards the mirror and made some adjustments.  I was shocked as I looked at myself; I looked stunning.  I couldn’t believe the transformation to my face.  I looked like a sexy, mid thirties, over made-up, slut.

“You like?” Carmel smiled at me.

“I look like a fucking woman!” I shrieked.

“Well that’s the idea stupid,” Carmel Laughed. “Follow me.”

I followed her out of the bathroom, stark naked and with my face made up to look like a whore. ‘Iron Bar’ Steve followed at a menacing distance.  Carmel led me into a cell in a set of six on the next level up.  The five others around it were all deserted but the cots were made up with what looked like satin sheets and comforters.

“This is your workroom honey, hope you like it,” Carmel said as she led me inside the cell.

I couldn’t believe it, the oversized cot was made up with satin sheets and a full sized wardrobe was open and hanging there were the clothes that Eddie had made me help him pick out.  Four pairs of different coloured high heels were arranged on the bottom of the wardrobe and in the drawers that were pulled open was the lingerie Eddie had spent so much time selecting with me. Now I knew why! Carmel led me over to the bed and sat me down.

“Well I guess I better show you how to dress too,” she said.  “Eddie was quite specific about what you were to wear for him tonight.”

Carmel selected a pair of shiny, sheer to the waist taupe pantyhose and rolled them up my legs. She stood me up and showed me how to pull them tight around my arse.  The nylon felt cool and slippery on my legs, not unpleasant. I had always loved to run my hands up a nyloned thigh but had never imagined what it would be like to wears them.  I nearly died when Carmel put her hands inside the gusset of the hose and grabbed my cock and pushed back between my legs. The tight nylon held it snugly against my ass.

“There,” Carmel said, “lets get that little thing out of the way shall we?” she laughed.

I heard Steve laugh at the door and realised to my humiliation that he was watching the proceedings. Next Carmel pulled a pair of silky nylon peach coloured full cut panties from the drawer with a matching bra.

“Here,” she said, handing me the panties, “put these on while I get the breastforms”.

I didn’t know what the fuck she was talking about, Breastforms?  I slid into the panties, the silky nylon of the panties created little electric shocks of pleasure as they rubbed against the sheer nylons as they slid up my legs.  Carmel turned around and was holding two perfectly formed small breasts, one in each hand.  She put them down and put the bra on me then placed each of the plastic breasts in each cup.

“There is some adhesive in the dresser draw that has instructions on how to adhere the breastforms to your chest. You can learn to do that later.  The way I’m dressing you tonight it won’t matter you just need the shape.” Carmel said, sounding serious about subject totally alien to me.

I was still in shock as to what was happening to me when Carmel sat me down again and lifted my feet one by one and placed a back shiny high heel on each one.  She pulled out a little jewellery box from out of a draw in the base of the oversize cot. 

“For fuck sake keep this locked away from now on and never lend your jewellery to any of the other girls.” Carmel said very seriously.

‘My jewellery!’ ‘Other girls!’ ‘My workroom!’ What the fuck is happening to me I wanted to scream.  I kept my cool though, I realised I had no choice but to succumb to the ministrations of this freak man/women who was dressing me or have ‘Iron Bar’ Steve cripple me for life.  One I saw Eddie I knew I could convince him that he had his little joke and that I would make up for what ever mistake I had made as soon as I got back to work as his finance manager, back in the general population of the jail.

Carmel selected a simple gold ankle chain and fastened it around my slim ankle.  The gold twinkled in the light against the sheen of the sheer nylon. Carmel put two gold bands around my right wrist, and a simple but elegant, gold ladies watch on my left.  She placed another simple gold chain around my neck, for which hung a black onyx stone set in gold.  She clipped matching earrings to my ears.

“We’ll pierce your ears tomorrow hon,” she said humming away as she worked.

Like fuck you will, I though to myself.  Next Carmel had me stand and I teetered on the high heels, steadying myself by holding on to her. 

She smiled, “You’ll soon get used to them.”

I thought again, like fuck I would because after tonight I’ll never need to wear them.  Eddie will see this is a mistake. Carmel selected a satin waist-cincher that matched my bra and panties and pulled it tight around my waist.  My already un-masculine body was now positively effeminate.  My smooth long legs enhanced by the sheer hose, my arse had been pushed out slightly by the squeeze of the cincher, my false tits that just proportional to my small build, and my little waist. I looked like a well looked after thirty-year-old woman.

Next Carmel took a cream coloured silk blouse and pulled it up my arms and buttoned up the front.  It was open down to the second button and showed a hint of my peach bra.  Next she had me step into a peach nylon half slip, that again matched my bra and panties.  It too gave me little electric shocks of pleasure as it slid up my nyloned legs. Carmel reached into the wardrobe and pulled out a hanger on which there was a bark blue women’s business suit.  I remember Eddie picking it out of a catalogue and wondered at the time why his ‘working girls’ would need something so sophisticated.  But along with nurse’s uniforms and other fetish clothing I figured it was just to pander to some expensive punter’s peccadilloes.

Carmel had me step into the skirt and pulled it up my legs and fastened it around my waist. She straightened my blouse, ensuring it was tucked in and then surprised me as reached under the skirt and pulled the half-slip that had become rucked up when I donned the skirt.  I got another of those little electric shocks of pleasure form her hands straightening the slip and touching my stocking legs.  I looked down and was surprised to see a pair of sexy pantyhosed legs showing from below the hem of a navy blue skirt that was six inches above my knee.  Attached to those legs were a pair of sexy nylon encased feet, the red toenails showing though the gossamer nylon.  Around one slim ankle a gold bracelet reflected a glint of light.

Finally Carmel helped me into the matching jacket and led me over to a full-length mirror that was attached to the wardrobe door.  I was amazed! Staring back at me was a gorgeous woman in her mid thirties. Her bottle – blonde hair and over made-up face atop the cream blouse and navy blue power suit made her look sophisticated but strumpet like.  Carmel spun me around so I could see my side and rear.  My ass stuck out provocatively and stretched the material of the skirt taught against my arse. It was forced that way by the pull of cincher and stance I had to adopt to remain on feet in the high heels. The rear of the skirt had a small split that showed about another six inches of the back of my nyloned thighs.

Just then I saw hand reflected in the mirror as it grabbed my arse.  It was Steve.

“You look great,” he growled as he pawed my arse and legs.

“Get the fuck off her Steve or I’ll tell Eddie,” Carmel screamed smacking Steve’s hand away.

Steve retired to the door sheepishly.

“You know Eddie always gets them first!” she yelled after him.

Then the full light of the situation dawned on me.  As I looked at the reflection of the trampy woman in the business suit I realised she looked just like a caricature of the ‘sexy secretaries’ I had seen posing in porn magazines just before they stripped off their clothes, page by page.

Now I knew why Eddie had called me his secretary! Oh my god! He had been planning this for weeks, having me help him pick out clothes, obviously getting his ‘girls’ to find out my sizes for clothes and shoes.  And now I had no choice but to be Eddie’s ‘sexy secretary’ or suffer an agonising beating and the loss of my limbs!

“Mike, now you are Michele, you look beautiful. I hope you enjoy your first time as much as I did,” said Carmel as she slid past me and out the door.

And that is how I became to be dressed as a woman and standing in the far corner of a darkened cell on E Block of Chelmsford Correction Facility for Men, and waiting for the most dangerous inmate in the jail.

To be continued………………………………..

All i could think of to say after that was that i could pretend to be a woman if they want which made them all crack up laughing. Then blondey said you can buy us a drink but we are all leaving in half an hour and don’t expect to come with us.  Damn i thought but fuck it i’ll buy them a drink and see.

Anyway i found out that the redhead was Linda and the blonde was Erin and the brunette was called April, they were all 30 and pretty to boot, all single and had been best friends since 5 years old. We finished our drinks and then Erin smiled at me and said how about another but then we must leave and as she said that she squeezed my ass. So i got the bartender to get us all another drink and excused myself to go to the toilet. When i got back the girls were smiling at me a bit funny i thought! Erin came over and put her arm around me and whispered in my ear “ We changed our mind! We’re still leaving but your coming with us!” Well i couldn’t help but let out a big smile which had April saying that i looked pretty happy with myself, which i did! I replied that i was which made them all laugh. We finished our drinks and jumped into a taxi and we went to Erins house which was close by.

I paid for the cab and April and Linda rushed inside whilst Erin had her tongue down my throat at the front door. Anyway after a bit of kissing we went inside and found the other two girls had made up a few lines of coke for us all, i don’t usually do drugs but if it was gonna help me with these three then i thought i better. Linda poured us all a drink of vodka whilst April put on some music. But Erin grabbed me by the arm and said i have to have a shower first.

Anyway she took me into the bathroom and stripped me off, then grabbed hold of my cock and gave it a squeeze. She grabbed a bottle of shower gel and said let me rub it all over you, so i did. Next thing i know all of my body hair is all falling off. Erin freaks out and says how sorry she is and that she passed me the wrong bottle. I shrug my shoulders and told her not to worry cos i look sexier like this anyway. She smiled and told me that i most certainly did. Luckily she didn’t wash my hair or i would have been pissed off big time as i have really long curly brown hair.

Well we finished the shower and she made me shave my stubble off then she handed me a silken robe that was white with lot’s of pretty pink flowers on it. We went back into the lounge room and had another line of coke, which by the way was really choice stuff and got us all pretty bloody high when Linda said that she liked my robe which made me blush. April piped up that after all in the bar i said i would pretend to be a woman and Erin and Linda said yes that i most certainly did! So i told them that my name was really Lulu darlings and pouted my lips a bit. Erin grabbed my arm and said follow me if i want to have some fun.

We ran into her bedroom and she pulled the robe off of me and told me to sit on the bed. Then she went over to her drawers and started rummaging around till i heard her giggling and then she tossed me some pink panties and a bra and told me to put them on. I had a good laugh and put them on for her and when finished she handed me some stockings and garter belt. She told me to take the panties off until i had the garter belt and stockings on and whilst i was doing this she made up some boobs for me with stockings. She told me to look through her wardrobe for a dress to wear while she got another drink for us so i searched through them and found a lot that i thought might look alright. It was strange because i had never done anything like this before but i was a pretty good turn on and probably because of the drugs i was gonna do anything and everything that Erin wanted me to because at the end of it i should get to sleep with her.

She came back in the room and told me to swallow this pill which she said was an exctasy tablet so i opened my mouth and poked out my tongue and she placed it there. I’d had a few pills before and this tasted terrible which is a good thing and she then wanted to know which dress i wanted to wear. I had picked out a beautiful little pink dress the same colour as my underwear. It had thin shoulder straps and showed off my new boobs wonderfully and came down to just above my knee. She obviously liked what she saw as she was telling me to put it on and nodding her head at the same time then she went back to the wardrobe and found some nice pink high heels for me to try on. Luckily my feet are only a size 9 and they fit perfectly and i did the buckles up and Erin looked so pleased with herself.

Now she said we have to do hair and i felt in heaven while Erin pleated my hair and put it into ponytails, then she put some fake nails on my fingers and painted them pink and then told me to sit still while she put some makeup on me. She seemed to be taking a while and the exctasy was kicking in nicely when after about half an hour she took me over to the mirror and i got to see what i looked like. Shit i looked pretty fucken good actually and even though i’m pretty high i thought and told Erin that if i seen me in the bar dressed like this i would have been over in a jiffy to introduce myself. She pulled a camera out of nowhere and started taking photos of me and i posed for her and did whatever she wanted me to.

that come on we have to go out Lulu but first we need another line of coke. By this stage my head was spinning out of control with these ladies and the drugs but i was loving every minute of it. We walk out onto the street and thought it shouldn’t be busy as it was 3 in the morning now and went down to the servo. When we got there Linda hands me a fifty dollar note and tells me to get three packets of smokes and a bottle of water while they all giggle and wait. There is a young guy about 20 years old working and his eyes are about falling out of his head perving on the four of us girls in his shop, he wasn’t bad looking either and i could hear the girls whistling and making comments about him as i went to the counter and asked in my most feminime voice for 3 packets of smokes please.He smiled and said “no worries Miss, can i get you anything else?” to which i replied “just this bottle of water”. He wrote something on a bit of paper  and gave me the change  holding onto my hand and smiling for several seconds and all i could think was that he had no idea. I handed Linda her change and we walked out of the shop arm in arm with each other and after we got out the door April asked if she could see what the young lad put in my hand. I didn’t know any of the girls had noticed but i was mistaken and i still hadn’t looked at it either and when i said i hadn’t been game to look Erin had grabbed it off of me before i could blink. She burst into laughter and said that it was his phone number and his name was Mark, then put it in her purse.

Anyway we kept walkingand as we passed a nightclub on the way home the girls all turned and dragged me in there with them with me nearly shitting myself at the thought of being there like this. Linda ordered us all vodkas and lemonade and we sat at a booth not far from the bar. It wasn’t a bad club and i had been there plenty of times before to pick up chicks but never with myself looking like one! Before you know it a guy came over and asked Linda to dance and off she went, Erin went to the ladies with April and they told me to stay there and watch the drinks. Then about a minute later a tall well dressed man came over to me and introduced himself as Marty and said he wanted to dance with me but i said i couldn’t as i was watching all our drinks so he sat down next to me and said if it was alright then he would wait for my friends to get back then dance with me. I didn’t know what to say and my head was spinning when Linda came back from her dance with a guy called Gavin who seemed rather smitten by her and who could blame him. So then Marty insisted that i go dance with him and Linda said “go on be a devil” so i did. It was good music with a good dance beat and then the song finished and the dj put on a slow one, i started to go back to the table but Marty grabbed me and pulled me in for a slow dance so i put my arms around his shoulders and went with the flow thinking it couldn’t hurt i suppose.

Erins place. I mentoined that it might not be a good idea but before i could finish what i was saying Linda had lifted my dress and pulled out my cock and started sucking on it. Now this girl knows what she’s doing i thought and after a few minutes of this i was about to cum when she stopped and said “i will finish you off if they can come home with us or you can leave right now by yourself and find your own way home.” So i reluctantly said ok and she made me promise we would take Marty and Gavin home with us and then proceeded to give me a wicked blowjob. Then Linda quickly touched up our makeup and we went back out to our table.

The boys had gone to the bar to get another round of drinks and Linda was smiling and told April and Erin it was all set up and when the boys got back April asked them if they wanted to carry this on back at our house to which the boys couldn’t agree to fast enough. So we all finished our drinks and left the club. We got outside and it was still dark but wouldn’t be for long as it was already six in the morning and we got a taxi back to Erins house.

When we got there we all indulged in some coke that Marty had and that blew us all away even more than before and April put some tunes on the stereo while Linda grabbed us all a drink. Gavin grabbed Erin and was fooling around doing some wacked out dance and Marty grabbed me and was doing the same then the other two girls joined in and we were all having a ball of a time. Next thing i know was Marty had his arms around me and started kissing me, now i didn’t think of myself as gay at all but tonight was different and shit, i was enjoying myself so i kissed him back. Linda and April took Gavin by one hand each and led him to the bedroom and this left me with Erin who i wanted so badly and Marty who wanted me but sure wasn’t going to complain if Erin came along for the ride.

Anyway we all settled on the nice wooly rug in front of the fire and Erin pulled out a joint to try to relax us all a little. When we finished the joint Marty started kissing me again and then Erin told him that if he wanted a fuck it was going to have to be her because i was having my period. Marty said “Damn” and then said he wanted us both but would have to wait till he could have me, maybe next Friday night after my womens business had finished. Then she spun me out by saying that Lulu can still pleasure you though Marty. With that she grabbed his fly and opened it to reveal a nine inch weapon that looked good enough to eat and Erin stuck her mouth over it straight away. Marty grabbed me and started kissing me and after a couple of minutes Erin ordered me to get down with her. When i got down there she told me to go for it if i wanted her afterwards and after she said that i didn’t hesitate and put it in my mouth. I must have been doing something right cos Marty kept saying things like “that’s it Lulu your fuckin awesome” and before i knew it he unleashed a torrent of come into my mouth. Straight away Erin told me to swallow it if i want my reward later so once again i did as she instructed and swallowed the lot, which to be honest i loved every second of it. Then Erin and i kissed and kept licking and playing with Marty’s cock until it got hard again and when it did Erin jumped on top of Marty and ordered him to fuck the guts out of her, and he did. April, Linda and Gavin came out and joined in with us whilst this was happening and all i could think was that it’s not fair that Erins getting it when i was the one he picked up!

Gavin hitching my dress up and pulling down my lovely little pink panties. I was scared then because i thought Gavin would see my cock for sure but if he did he didn’t say anything and rammed his big cock into my asshole. I hurt like hell to start off with but then started to feel nice and it was turning me on big time when Gavin reached around in front of me and grabbed a hold of my cock! Without missing a beat he told me i was the sexiest piece of ass he had ever had and filled me full of his spunk which felt wonderfully warm filling me up.

So now my secret was out and i realised that Gavin didn’t care but what about Marty? Well i found out soon enough cos Marty jumped off of Erin and told Gavin to get out of the way cos he wanted a go. Next thing i know is Marty is fucking me hard up the ass and Erin is sucking my cock at the same time. April and Linda got into a 69er with each other and Gavin watched us all go for it and i reckon we all came at the same time and it was mind blowing to say the least. I had never been fucked up the ass before but somehow i’m pretty sure i will be again!

After that was finished we all sat back and had another drink and all agreed that it was fun and then i had two guys and three girls all look at me and say “can we do this again next Friday night” to which i replied that i didn’t know if i could or not but Erin said “you will, you’re not going home, you are moving into my room and you will do as i command and we have pictures of you that your friends might be interested in seeing if you don’t agree”.

I knew she was right and to be honest didn’t care as it had been the best night of my life, ever. Afterwards they let the guys go home and April and Linda went off to one bedroom whilst Erin took me to hers and we made love for hours which was heaven for me.

The End of part one...........

If you like this i will be glad to write some more, just ask me!

 xxx Lulu

Well the bouncer at the door searched my ID for flaws then allowed me to pass.  As I walked by he whistled at me and I blushed and turned and said, “Thank you.”

He chimed back with, “No thank you for the view of your butt.”

I had on a silk shirt buttoned half way up; it was hot pink and with white slacks and shoes made me look good.  I had my nails filed and on the way there I coated them with clear polish. 

As I walked in several others followed behind me, there were a few guys already mingling so I strolled up the bar and ordered a margarita.  I had drunk one a couple of times when my mom would make them and leave the rest in the blender.  I was sipping on it when I noticed two hunks that were coming near me.  I acted coy and shy and it paid off big time.  The two of them were interested and as my cock showed, so was I, though I acted different.  They seduced me into the back booth for another round of drinks and we talked about things in general while I gulped the second one down.

Ivan was 6’2” light sand for hair that was tailored and short.  His blue eyes look like the sky and his dark tan was hot.  Hugh the guy by him was equally as attractive and they were almost the same except for his dark curly black hair.  They asked me how old and I lied, and said 19.  Then as we talked I found out that Hugh was 29 and Ivan was 25.  They were funny and sort of witty with me through the third round of drinks, but when the fourth round came they had the bartender use Vodka and I started to feel the effects right away.  Suddenly I started telling them, “I came here tonight to get myself screwed and to see if I can suck a cock like I have dreamed about for years.”

“What does it take to get your horny Billy?” Ivan asked as he petted my hand and slowly rubbed up my right arm.

“Oh that’s easy to do, but if you caress my nipples and suck them you can get into my pants and anything else as well,” I honestly replied wishing I hadn’t later.

“Sounds like you wish you were a girl then Billy.  Maybe we should rape you like a girl?  Come on what do you say to letting us take you right here and now?”  Hugh said as he slid his finger to my lower buttons and undone them.

As Ivan helped soon my shirt was opened and each man had a finger inside it caressing my nipples, and between the coos and ayahs, I replied, “Oh hell why not.”

Just about that time a couple of other men came over that were friends with them.  They were hard to make out as the drinks made my vision fuzzy, but one was big black and handsome and the other was a smaller red headed man.  Hugh had my shirt in the booth as Ivan began to undo and remove my pant sand sexy little silky white thong briefs.  I felt my cock exposed to the cool air and warm hands of Ivan just as Hugh leaned over and kissed me on the mouth.  I turned towards him a bit and off went my pants underwear and shoes.  His hands were playing with nipples as I felt my body float up and onto the table.  These men had done this before and in the bar, even though it was against the law.  The owner seemed to know that if he stopped them it would only make things worse so he let us go.

Hugh helped himself to my ass and began to lick and rim my asshole out, Ivan moved to drop his pants then kiss me before he offered his cock to my wanting mouth.  I looked at it for a few seconds before Hugh plunged inside me.  Then as I got use to the cock in my ass I licked Ivan and started to suck him slowly.  A few other people in the bar began to gather around and watch us as the bouncer stopped letting anyone else inside and told them the bar was full.  I was on my side naked as these two experts took full advantage of my horny virgin body.  When I felt Hugh pulsing to his orgasmic climax, I got so hot that I sucked Ivan like a vacuum and boy did he explode.

My night was far from over as the two of them relaxed the other two men took over and soon I had a new cock to suck and bigger dick in me.  The sounds that we were making were animalistic and raw and the feeling of his cock in my mouth aroused me to suck him off and swallow as much as I could.  The black man drove in my ass and made squirm from it a few times until he launched his load in me.

Suddenly I realized that I was being a slut and I looked up to see more blurry images of people and hear another set ask to take me as Ivan began to caress my nipples.  Men fucked my mouth and ass and as the night grew on I was fast becoming a male whore, and loving it.

One cock came to my lips it was bent rough and huge and as I took it in my mouth I was sucking the cum in from my lips of another one and there in the midst of this were my very well hung next door neighbor and his lesbian wife.  They slid up to me and started to enjoy me as well and before I knew it the man had me suck his cock off and then fucked me before the night ended.  At just after three in the morning they closed the bar and tossed me out the back door naked into the alley and no clothes.  I was so drunk that I couldn’t care and after passing out I have no really ideal of what happened to me the rest of the night.  Sometime early the next morning I awoke to find myself in a bed.  The room was dark and cold and the only light came from a screen at the base of the door.  I stumbled from the bed to find the floor bare cold concrete and then I saw a small handle on the door and turned the knob but it was locked.  I fumbled around until passing out again.  The next time I awoke the room was much plainer and I could see it was a cell.  I had been arrested by the police for public drunkenness and taken to the intake center.  They had kept me several hours before I realized what had happened to me and when they released me to my angry and upset mom, I wished they just had kept me in jail.  They had me in the adult prison and were just as mad at mom when they found out I was a minor.  She took me home and kept me inside until I was clearly berated beyond all words. 

I was grounded and told to stay home for eight weeks.  Then came my appearance and parole and was made to be home bound for another six months.  Since I refused to admit being in the bar they couldn’t fine them or anything for what happened to me and they couldn’t get anyone who said they had seen me there either.

Then after a few weeks more, my mom finally allowed me some freedom, two weeks before I turned 17.  I got me a part time job and saved all the money I could because while all this happened to me, all I really wanted was for it to happen every night.  I knew my mom understood I was gay, but she didn’t realize I wanted to become a woman.  My brother who began to understand me and accept me also used me during my home bound time.  I let him fuck me every night.  Pretty soon he like my ass better than his girlfriends and started finding ways to take advantage of me being home.  Including having me naked and tied over the exercise machine while he fucked me.  I made him shave my legs and arms and cock bald and then he started getting me the pills I needed to transform.  That’s why I got the job to save money to pay for it.

When my brother found out that I was going to do it, he helped me pay for it.  Then finally I found out how much I needed it one night when he was gone on a date with a girl.  I was just out of my bondage and the neighbor saw me and invited me over.  His wife was there with a camera and showed me some images she had saved on it.  It was me being fucked like a dog by her husband and some other men.  It made me so horny that I stripped naked and begged for him to fuck me and her to shoot it.  They made a copy of the pictures and put it on a disc and I used them to get dates on the net with.  Pretty soon I came to realize I could get money from men for sex, so I sold my body for $25 a fuck or $50 for a gang bang.  I made enough money by my 18^th birthday to pay the whole thing and make enough contacts to enjoy it afterwards.

Today I am know as Sylvia Dee, I am the same height but I now have a set of 36D boobs and a soft little slit where a cock use to be.  I have been fucking men so long now I don’t miss my dick.  But if I go without sex for more than a day I miss getting dicks.

"Mike, now you are Michele, you look beautiful! I hope you enjoy your first time as much as I did," said Carmel as she slid past me and out the door.

And that is how I became to be dressed as a woman and standing in the far corner of a darkened cell on E Block of Chelmsford Correction Facility for Men, and waiting for the most dangerous inmate in the jail.

 

Part II

 

"She's all yours Eddie. She looks beautiful." I heard Carmel say as 'she' disappeared down the corridor, her high heels clicking on the tiled floor.

Eddie appeared at the door to the cell, he stepped inside and closed the door behind him.

"So what do you think of the little nest I have here for you 'secretary bird'," he asked sarcastically.

"Eddie, what's going on, what's all this about," I implored.

"Well if you haven't figured it out by now hun, you are a lot dumber than I thought. I needed a secretary, but not just to be my accountant, I need a 'Girl Friday' who can help run my business and take dictation; emphasis on the DICK," he smirked.

"I recognised your potential early, so now I have made you into Michele, my secretary, confidant, and soon to be my personal assistant. Very fucking personal if you know what I mean!"

Eddie stepped towards me. He was dressed in a pair of light tan linen pants, a smoking jacket, and expensive looking moccasin slippers adorned his feet.

"You look beautiful hun, just what I was hoping for; come here," he whispered hoarsely and reached out to pull me to him.

I immediately tried to step back out of his reach but he gripped my forearm and pulled me forward. As he did his other hand came up and slapped me soundly across the face. It was what the inmates referred to as a 'bitch slap', and it really stung. My eyes started to water.

Eddie took a handkerchief out of his pocket and put it to my teary eyes.

"Now Michele, don't cry; I would hate to ruin all the hard work that Carmel did with your makeup," he said.

"Just behave yourself and there will be no more pain."

He lifted my chin and looked deeply into my eyes.

"God your just fucking beautiful," he whispered and put his arms around me.

Eddie embraced me, locking his strong arms around me. His faced moved forward and I sensed he was about to kiss me. My involuntary action was to move back. His right hand came up again and was held out flat near my face, ready to slap me again. I forced myself to stay still.

He enclosed me in his arms again and this time his lips came down on mine. It was the strangest feeling, I could feel the slight rasp of afternoon shadow on his face, smell the faint scent of his aftershave and the press of his thick lips against mine. He pushed his tongue into my mouth and I could taste my lipstick mingled with his mouthwash. His tongue started to explore my mouth and he pulled me even closer.

I forced myself not to back away, rather I became limp. I knew there was no way out of my current predicament without extreme pain and punishment. Even then Eddie would take what he wanted from me. I tried to clear my head and just endure what was happening to me without further antagonising him.

Eddie was now kissing me passionately, his lips pressed hard against mine, his tongue exploring under mine then slowly working its way around my mouth, flicking and probing. His body was hard against me and I felt a hand slide down my back and come to rest on my buttock. He rubbed his hand there, the material of my dress and half-slip whispered against the smooth nylon of my panties and hose.

"Mmmm," Eddie whimpered, his lips still against mine.

He lifted his face and looked at me again. I realised he was not looking at another man, but a gorgeous woman in her mid thirties, her hair styled in a bottle – blonde bob and wearing thick makeup, rouged cheeks and plum red pouting lips.

"God I just have to have you hun, my lovely little secretary bird; this is just how I imagined it would be!"

Eddie started kissing me again and I felt his other hand slide down so that he had both of my buttocks in his grip. I felt him lift up the hem of my business suit skirt and caress the material of my half-slip. His hands worked in a circular motion in time with his tongue, rubbing the silky slip against my tight pantied buttocks. I was so shocked that it took me a while to realise that he was also gyrating his hips against mine; pulling my lower half against his as his passion intensified.

I commanded myself not to move, to just take what was coming; it couldn't be worse than a beating or broken legs!

Then I felt it, I went from being a limp rag doll and tensed up, almost pulling myself away. Using the utmost self-control I forced myself to go limp again in his arms and allow him to ply my body against his. What I felt was a long iron bar that could only be an erection pushing against my stomach. I could feel it though the material of his slacks and my skirt.

Eddie was gyrating against me now, his tongue working feverishly in my mouth, his lips crushing mine. The hands on my ass gripped my buttocks and pushed my lower body harder against him. He was 'dry humping' me I realised; pushing his erect member against me through our clothes. I heard and felt a deep humming from his throat and he was breathing heavily in and out of his nose as he continued to kiss me deeply.

Eddie suddenly stopped pushing on my buttocks and I felt a hand leave my ass, glide across my hip then move between us. He fumbled there, his hand between my navy blue skirt and his loose tan linen pants. My god I knew what he was doing! And then I felt the fruits of his efforts down there.

Eddie had freed his erect penis from the confines of his pants and it was now like a hard iron bar between us. His hand flew back to my ass and he again rucked up my skirt and used both hands to caress my buttocks through the slip as he pulled me back against him.

He ground himself against me, his cock hard against my lower abdomen. I could feel the girth of it though the layers of skirt, slip, panties and pantyhose. I concentrated harder on not panicking and just allowing Eddie to do as he wanted; surely this would be over soon.

Eddies kisses had now become a hard insistent invasion of my mouth; every few seconds he had to break to take a breath; I could feel my lipstick smeared over my lips and over my teeth. During these little gasps for breath he would pant,

"Yes! oh yes baby! so good! so good!!!"

"Gotta do it soon! gotta do it soon!!!"

Eddie again removed a hand and fumbled around down there between us. This time I felt him lift my skirt up completely so it was rucked up around my waist. He lifted me up and forced me to my toes, my heels left the ground and I fell further against him, my face now level with his as I balanced in the awkward high heels that I had never worn before. Eddie struggled with his erection and I felt him push it down then release it so it sprag forward whilst at the same time he pushed our lower extremities together.

His cock was now wedged between my legs, hard against my crotch and encased in the silky sheer material of my half-slip.

"Oh my god!" Eddie groaned and began his hard circular humping against me yet again.

He got into rhythm, dry fucking me in time to his feverish kisses; slowly circling his manhood he had trapped between us. Eddie tugged hard on my slip and I felt it start to drag down my thighs until it was around the tops of my knees. Now I could feel his turgid penis trapped between my pantied crotch and gossamer hosed thighs. Eddie was pushing up now as he thrusted, fucking the silken trap made by my pantyhosed thighs and nylon pantied crotch. I could feel the head of his penis rubbing itself along mine through my panties. My penis was still held in place tight between my legs by the gusset of my pantyhose.

Eddie had just what he wished for I guess. His slutty secretary forced to stand tiptoe in shiny black heels, her silken pantyhosed legs circled by her pretty peach half-slip just above her knees. Her dress rucked around her waist, her blonde bobbed hair framing a heavily made-up face that was locked to his in a powerful stream of kisses.

The big strong man held his sweet secretary in his tight embrace, sliding his tumescent member between her thighs, the gossamer of her hose and silken sheen of her panties serving to provide little electric shocks of pleasure through his body.

I felt Eddie quicken his pace and his cock begin to throb. He pushed against me harder and he held me so tight I though he would squeeze the breath out of me. His tongue was now a wild wet animal, thrashing in my mouth, fluttering and exploring every crevice.

Both his hands gripped my buttocks squeezing them roughly through the gauzy nylon panties and pushing me forward and back to the rhythm of his thrusts. Then he groaned and gripped my ass so tight that I felt the nylon panties tear and his fingers burst through and bury themselves into the gusset of my pantyhose. He forced me against him as hard as could and I felt his penis begin to pulse and throb.

Hot wet fluid suddenly soaked the tops of my thighs and the crotch of my panties. I felt stream after stream of his creamy seed shoot against my silken hosed thighs and being to slowly run down my legs. My crotch was soaked with hot sticky liquid and as I struggled to breathe I could smell the salty, slightly swampy smell that is associated with fresh semen.

Eddie had ejaculated against me. He slowed down his thrusts and slightly eased his grip on me. His spend had now invaded the layers of panty and hose and I could feel it warm and milky against my penis.

Eddie's hands slid up my body to my shoulders and he gently eased me back and lowered me to my feet. He looked down, pulled up my half-slip and smoothed down my dark blue skirt, the hem coming to rest against my sticky thighs. Then he did something that summarised in my mind how used I felt; he took a handful of my skirt and wiped his slowly deflating penis on it; the globs of semen and silvery seminal fluid staining the dark material as he cleaned himself on me.

"Not bad Michele," he chuckled, "Now clean yourself up sweetheart, you look a complete fucking Mess."

 

 

To be continued………………………………..

 

 

Eddie's hands slid up my body to my shoulders and he gently eased me back and lowered me to my feet. He looked down, pulled up my half-slip and smoothed down my dark blue skirt, the hem coming to rest against my sticky thighs. Then he did something that summarised in my mind how used I felt; he took a handful of my skirt and wiped his slowly deflating penis on it; the globs of semen and silvery seminal fluid staining the dark material as he cleaned himself on me.

"Not bad Michele," he chuckled, "Now clean yourself up sweetheart, you look a complete fucking Mess."

 

Part III

 

Carmel appeared as if from nowhere and took me by the hand. I was so shocked at what had happened that I just followed her instinctively, as I passed Eddie, clattering on my high heels, he reached out and spanked my arse.

"Have her ready in half an hour Carmel, I haven't finished with her tonight; not by a long shot."

"Oh, and tell Steve he can use for ten but he's not to fuck her, ok." Eddie bellowed down the corridor.

"Of course Eddie, you want the secretary thing again or you want her ready for bed?" Carmel asked.

"I think I'll have her fully dressed again; stockings this time though, I don't want to have to rip any more pantyhose to get what I want ok!" Eddie answered.

"Sure honey, I know what you like, she'll be ready for you in half an hour."

"And don't forget to tell Steve he can't fuck her, I don’t want slops."

"Of course Eddie," Carmel smiled sweetly at Eddie, "Now come along Michele lets get you cleaned up honey," Carmel whispered dragging me down the corridor towards the bathroom on E Block.

"What's he on about?" I asked Carmel as we went into the bathroom and she led me to the sinks.

"Eddie is going to use you until you bore him, then you are going to be just one of us girls; a common prostitute hawking your pretty arse for Eddie; making him money and occasionally making him come." She sneered at me.

"Just get used to it; learn to like it!"

"Learn to like it!" I scoffed.

"Learn to like being dressed as woman and used by these poofters in this jail; you're fucking joking! I hurled at her.

Then I felt an enormous slap across my backside; the pain was excruciating.

"Oh god!" I moaned.

"No not god, just little old iron-bar Steve. Fucking hurts don't it; my steel bar crashing against your arse like that?"

"So you think I'm a 'poofter'; well I've got a another steel bar right here in my jeans honey and you've got about ten minutes to take care of it!"

It was Eddie's enforcer Steve, undoubtably he had heard Eddie say he could use me briefly and was wasting no time coming to claim his prize. I realised at once that fighting him would be futile and decided to let him take what he wanted. I had heard Eddie say he couldn't fuck me so I figured the best defence was attack. If I excited him enough maybe I could get him to orgasm against me just like Eddie had done. That was humiliating enough but I didn't want to consider any alternative.

I turned around and forced myself to move towards Steve and embrace him. I rubbed one nyloned thigh against his leg and reached up and kissed him. His breath was atrocious, I forced myself not to gag and pushed my tongue into his mouth and gave him a long kiss.

"Steve honey, you don't have to use that bar on me; lets just take care of the bar I can feel throbbing in the front of your jeans," I whimpered in what I hoped was a sexy parody of a seductive female.

"Oh but you don't understand Michele," he sneered, "its more fun to take what I want!"

Steve pulled me roughly to him and locked his lips on mine. At the same time his hand went to my skirt and yanked it up around my waist. He twisted his hands in the nylon of my slip and yanked it down around my knees and ground his body against mine. I felt his hard member pushing against me though the rough denim of his jeans.

Then Steve pushed me away to arm's length.

"Drop the skirt bitch'" he hissed.

"What?" I answered not understanding quite what was going on.

'SLAP'!

My head exploded with the force of the slap to my face; I thought my head had been knocked off.

"Don't you fucking mark her!" Carmel warned Steve.

"Well you tell that bitch, I ain't half as nice as Eddie so she better just take what's coming ok," Steve hissed at Carmel.

"Ok Steve, I think she gets it!" Carmel retorted.

"Well let's just make sure," Steve answered and then punched me in the stomach. I doubled over in pain completely winded.

"Right I'm wasting time, no more talk; just action. I tell you what to do and you do it bitch ok?"

I nodded as best I could, my face was on fire from the slap and I still couldn't breath.

"Skirt!" Steve demanded.

I put my hands to the waistband of my skirt and tugged it down around my ankles then stepped out of it along with my slip.

"Now my jeans!"

I stepped forward and tugged at Steve's belt.

"On you your fucking knees you stupid cunt!" Steve bellowed and brutally pushed me down.

Now my face was level with Steve's crotch and I reached out and undid his belt. I noticed again my manicured painted nails as I eased the zip of his fly down and snapped the button at the top of his jeans. As I eased the jeans down his legs a fetid aroma assaulted my nose and I noticed his putrid underwear.

"Stand!" Steve ordered.

I stood, tottering on my heels trying to recover my breath. Steve grabbed me and forced himself against me pushing his tongue deep into my mouth and pushing his hips against me. Carmel looked on at Michele; this attractive petite woman in heavy ruined makeup, dressed in her blouse and jacket but without her skirt, wearing torn and laddered hose and panties was teetering on her stylish black pumps as this jailhouse hooligan with fetid breath and stained boxers ravaged her.

I felt Steve reach between up and knew what he was up to. He was freeing his penis from his underwear as Eddie had done. I was still determined to get this over with as soon as possible and seized the initiative. As soon as I felt Steve's erect member against me I reached down and gently held it. I had never held another man's penis before and it felt tactile and spongy, I could feel the thick veins running along it. It also felt slick and warm. I commenced a slow stroking motion, easing my hand along the shaft and circling the enormous head. The cock was so thick that I couldn't grip its full girth in my hand.

Steve groaned, "Oh yeah bitch, you know what daddy likes."

He pushed me back slightly so he could see my painted nails trailing along his shaft as I wanked him. A thin thread of shimmering clear pre-come ran from the purple head of his penis across to my gauzy nyloned thigh. Steve reached out and rubbed my pantyhose thighs and then worked his way up to my panties. I stiffened as I felt his hand go inside my panties and begin to fumble about. I forced myself to relax otherwise I knew Steve would belt me again. Steve eventually found my thin soft cock nestled in the crotch of the sheer nylon panties and he began to free it from its little nylon prison.

I concentrated on slowly masturbating him to the best of my first-time ability. I gripped his member tightly and slowly squeezing and stroking as I worked my hand up and down his penis. He must be enjoying it I though, because he was just staring at my hand wanking him while one of his hands stroked my nyloned thighs and pantied crotch. As his other hand had finally freed my member, he began to squeeze it harder and harder. I just concentrated on getting this over with as soon as possible, the feel of his hand on my penis was vile.

I decided to move things along and pushed myself against him stroking his cock with firmer faster strokes. I lifted my head and kissed him, gently sliding my tongue along his gums and exploring his mouth, blocking out the awful taste of his breath. I guided his member against my pantyhosed thigh and rubbed it there, the underside of his cock with all those nerve endings rasping against the diaphanous nylon as my painted fingernails gently raked the top of his turgid cock.

I began to pump my leg up and down so that he was dry fucking me, similar to what Eddie had done. With my fingers stroking and squeezing in time with my humping leg I was hoping he would soon climax. He was groaning now and breathing heavy; his fetid breath puffing in my mouth. Combined with the meaty stench coming from his crotch I was ready to gag but kept control and tried harder to please him, kissing him deeper and stroking him harder.

Then he suddenly grabbed me by the shoulders and threw me back away from him. I stumbled back on my heels and my back crashed into one of the sinks, winding me again.

"Oh no you fucking bitch! You fucking cunt! I know what you're up to!" Steve roared.

"You're trying to get to come like this ain't you?"

"Well I ain't going to come in Eddie's leftovers. Get back here!"

I moved forward towards Steve warily. This parody of a secretary in a blonde wig, come-soaked and torn hose and panties, tottering on shiny black heels, dressed from the waist up in blouse and business jacket. What a sight!

Steve reached out and put his hands on my shoulders and pulled me to him. He kissed me deeply, forcing his tongue deep in my mouth. Then he eased his hands up to my shoulders and commenced to push me down.

'Oh God! I know what he wants,' I thought.

I dropped to my knees on the cold tiled bathroom floor and stared eye level at Steve's disgusting throbbing penis. He grabbed my head in both hands and pushed it forward so that the head of his cock was between my lipstick lips. He kept pushing but I couldn't open my mouth. The smell coming from his loins was fetid and I was sure that monstrous member would make me gag and vomit..

SLAP! I saw stars and the ringing in my ears blocked all other sounds. I started to cry and as I did Steve grabbed my head in both his hands and pushed his hard, throbbing cock into my mouth.

"You take this bitch, and don't bite or you're fucking dead!" Steve fumed.

He pushed the filthy thing into my mouth until he felt me start to gag and then commenced raping my face. That's the only way I can describe what he was doing to me. He held my head and raped it! He thrust his filthy, foul tasting, pulsing, penis in and out of my mouth. Besides the cheesy rancid taste there was also a sweet salty taste that I knew to be pre-come. My gag reflex was suppressed as long as he didn't drive his cock too deep into my throat, but it was so huge I couldn't breath.

Then I sensed Carmen beside me.

"Breath through you nose hun, breath your nose. He won't be long, I can tell he's nearly there."

Steve tightened his grip on my head and slammed me back and forth against his cock. He pulled me back until just my lips circled his plum coloured knob; then drove me against him as he thrust forward, forcing his turgid meat into my mouth. As a reflex I moved my tongue around the shaft and sensed his enjoyment. I was hoping he would come soon as every time his cockhead hit the back of my throat I had to gag. Then I realised the sick bastard was getting pleasure out of my gagging. Now he increased his attack on my virgin mouth and I tasted more and more of his pre-seminal fluid. He was groaning and panting.

"Yeah bitch, I'm coming whore, take this!"

He slammed forward hard and pushed my face into his groin and held it with two hands at the back of my head. His penis throbbed and erupted in my mouth and I felt the hot salty taste of his seed as it exploded from his glans. I started to gag and tried to force myself free as his semen flooded my mouth and slid down my throat.

"Take it bitch, take it!" Steve howled in his orgasm.

"OH Yeah baby, on your face yes! On your face!"

Steve pulled my face out his groin and held it close to his crotch with one hand; with the other he rubbed his still ejaculating penis all over my face. His ejaculate shot across my cheeks and landed on my eyelashes, a string of hot semen running across my face. Another spurt shot against my lips and up my nose. I felt stream after stream of semen scald my face and start to run down my neck. The thick gobbets of milky come smeared my cheeks, nose and lips. Looking out my eyes I could hardly see because of the ropes of hot come across my eyelids and lashes.

Steve's orgasm started to subside and he continued to rub his cock all over my face. He smeared his spend all over me, it combined with my lipstick and makeup to make a hot sticky film that covered my face. Steve stepped back and looked down at me, on my knees, may face covered in come, my clothes a mess and makeup mixed with semen, caking my face.

He reached out and grabbed a hand-full of my blonde hair and wiped his cock clean in it.

"Get this useless bitch cleaned up and dressed for Eddie; her night's only just started!" Steve sneered at Carmen as he turned his back and walked away zipping up his fly.

 

To be continued……………………………………………………………………………..

Part IV

Fifteen minutes later I was back in the cell Carmel had described as my 'work room'. She had cleaned me up in the shower and led me back here, dressed me, and was now putting the finishing touches to my makeup.

I was in daze; Eddie coming against my crotch and thighs was one thing, but 'Iron-bar' Steve's brutal rape of my mouth and then the humiliation of him ejaculating over my face had left me blank and bewildered. I had followed Carmel like a drone and let her take care of me and prepare me for my next encounter with Eddie. Now she was getting angry.

"Oh for fuck sake pay attention hun; I can't be doing your makeup for you every day, from tomorrow on your on your own!" she scolded.

She had selected my clothes and dressed me again but had to constantly remind me to watch what she was doing as I would need to dress myself in future. She dressed me like a whore!

After making up my face with heavy foundation, powder and blush, she had applied three different hues of eyeshadow ranging from frosty pink to mauve purple on my eyelids, working up to my plucked brows which she had highlighted. She applied lashings of mascara to my full lashes and finished with ruby red lipstick. She put on three coats and made me bite down on a tissue between each application to set the lipstick.

"This will stay on even during the most serious blow job she laughed," when she was done.

Next she had me put on a red nylon and lace garter belt. (Again I had vague recollections of helping Eddie select this item amongst the range of lingerie he ordered for his 'working-girls', as he referred to his transvestite prostitutes, who created a large part of income in the jail.) Carmel attached black, sheer, fully-fashioned nylons to the garter clips. As she smoothed them up my legs the electric spark of nylon on my legs bought me out of my daze long enough to admire my well-formed legs in the reinforced heel and toe nylons; the back-seam ran up to the gauzy reinforced stocking top cinched in the garter clip.

Again she fastened a gold chain around my slim ankle and had me step into a pair of shiny black, patent leather, open-toe sandals which had to be the highest heels I had ever seen. When I remarked I would never be able to walk in them Carmel laughed and said,

"What the fuck makes you thing Eddie even wants you on your feet tonight sugar; you'll be just fine on your back!"

Carmel pulled a pair of black see-through nylon panties up my legs and gave my arse a squeeze as she adjusted them on my hips with their high cut sides showing my upper thighs. She pushed my flaccid penis between my legs and hid it away, tucked under the gusset of my panties. She had me put on a red lacy bra to match the garter belt, again showing me how to adjust the breastforms just right. Over this ensemble she helped me into a purple cape of shimmering satin with long flowing sleeves, it buttoned only at my neck and came down to mid calf. She touched up my red nail polish and led me on shaky heels to the mirror.

Carmel had arranged on my head a long black wig with red highlights. My hair was dead straight, "Morticia Addams" style, and as I looked in the mirror I looked like some cheap Goth whore. The cape was open at the front displaying my lingerie clad body and the ultra-high heels caused my arse to push out and forced me to adjust my posture like a street walker strutting her stuff.

Carmel led me over to the bed and sat down next to me.

"Now Michele, you know what's coming so I won't pretend like its going to be nice the first time it happens. My advice is to get Eddie good and randy; the more excited he is, the sooner he will come hun."

"Under the pillow there is a tube of lubricant, if you get the chance use it; it will make things a lot easier on you babe."

"Now I know you don't believe all this is happening to you, but it is. There is nothing you can do about it; the only other alternative is not worth thinking about; you don’t wanna spend the rest of your life in a wheelchair doing Eddie's books."

"Believe me Michele you will either grow to like this life; or you will grow to tolerate it, but there ain't nothing else in your future while you are in this prison."

Carmel left me with these fateful words while I sat and waited for Eddie McManus, the most ruthless man in Chelmsford prison. The man who had only an hour before forced himself against me and orgasmed against my body, then gave me to his underling who orally raped me and ejaculated over my face. The man who was about to sodomise me, then put me to work as a transvestite prostitute for use by the scum, the guards, or anyone who could afford the price.

I made a futile effort to try and work out in my mind how often Eddies 'girls' were used. As his 'secretary' and bookkeeper I knew how much profit he made from his crossdressed whores but had no idea how many he had or how much they charged. It was a useless exercise but it kept my mind off the inevitable fate about to befall me.

I felt a hand slide up my thigh and I jumped about a metre in the air.

"Fuck!" I cried in hoarse whisper.

"Well yes please honey; you sure look like you need it 'Secretary bird', you're dressed just like that’s what you need; a good fucking!" Eddie laughed.

"Oh sorry Eddie, I didn't realise you had come in." I offered in a conciliatory tone.

"Oh fuck the small talk Michele, I've got my second wind now; I just loved watching what Steve did to you in the shower block; it's got me hot as hell!"

"You…….. you saw!!!" I whispered.

"Oh yes honey, I saw. Your plump red lips looked really good clamped around Steve's big cock; you've just got to learn to swallow girl, then you won't get that yucky mess on your face."

"Of course some of your future customers like to see a pretty girl with come on her face, its adds to their pleasure and puts snotty 'Secretaries' in their place. Imagine how many of your new customers are going to be guys that you treated without the courtesy and respect they have come to expect. When you were my number one confidant you had my protection, but now you are just another prostitute. I think some of them will pay nicely to see you humiliated." Eddie stated matter of factly; cruelly!

"Anyway enough small talk," Eddie pulled me to him roughly.

I was prepared this time, rather than fight him or become pliant in his arms I responded. As his tongue invaded my mouth I pushed mine into his and commenced a passionate kiss. I made my mind go blank and remembered what Carmel had advised me, 'get him aroused and he will come sooner'.

Eddie's hand went straight to my thigh and he stroked the cool sleek satin cape over my stockinged thigh. He obviously liked the feeling because he stated to grunt as he continued to kiss me. He pushed me back on the bed and straddled me, all the time keeping his lips locked on mine as he grunted and snuffled like a pig. Eddie was now running his hand up and down my stocking legs working his way from my ankles up to my thigh as he pulled my legs up and bent my knees so that my enormous heels were flat on the bed pulled up close to my buttocks.

Eddie now ran his ran over my panties and reached into the gusset and found my flaccid penis tucked away. He pulled it free and rubbed his hand over it through the gossamer of the light clingy nylon. I shuddered.

"Oh don't be shy Michele; some men won't even kiss you before they fuck you in here; at least I'm giving you some foreplay," Eddie chuckled then again attacked my mouth with his.

He took my hand and bought it up to his shorts, he was only wearing his smoking jacket over them, the light pants he had been wearing earlier had obviously been discarded. He put my hand against the front of his jockey shorts and I felt the heated bulge of his package. I remembered how Steve had reacted when I masturbated him; the first time I had touched another man's penis, and I used the same technique on Eddie.

I dragged the back of my hand over the bulge so that my fingernails dragged agonisingly slow over his tumescent erection. Then I feathered my fingers back down his member, softly fluttering them against the rigid pole. Eddie groaned and broke the kiss so he could look down at my painted red nails running up and down across his sac and his rampant member which was straining against the light material of his shorts.

I now made a clinical decision to increase the tempo of this foreplay to excite Eddie further so that when he eventually sodomised me he would hopefully be ready to climax quickly. Maybe if I was lucky I could just get him to come against me again before he could rape me!

I reached into Eddie's shorts and gently stroked his scrotal sac using my fingernails to lightly scrape against the puckered sensitive skin. Eddie groaned and began to kiss me passionately again and with my free hand I stroked his face and ran my fingers through his hair. I circled the girth of his erect member and started a slow feathery stroking motion up and down the shaft; as I came to his glans I flicked a finger over the spongy mass of his knob.

Eddie adjusted himself over me and shucked off his jacket, pulled down his jockey shorts and discarded them. He was now naked and stretched over me, his rampant penis sticking out proudly hard against his belly. Eddie lowered himself on top of me, pushing my legs down so I was suppliant; lying beneath him with my legs splayed apart.

Eddie lifted himself up on his elbows and gazed along my body. He took in the shiny black ultra-high heeled open-toe sandals on my feet with the fully-fashioned heel and toe of my nylons exposed. He caught a glint of light off the gold chain on my ankle and ran a hand under my leg to follow the seam of my stocking to the decorative stocking tops on my thighs. His hand followed the garter strap up to the red lacy garter belt and across the sheer black nylon see through panties where he gently stroked my still flaccid penis. His hand continued upward to dwell briefly on my red lacy bra then continued up, following his gaze to my face.

He stroked my cheek as looked into my heavily made-up face, he pushed a finger into my mouth and I sucked on it seductively. Eddie stroked my jet-black hair following the mane to where it caressed my shoulders, the red highlights in my hair enhanced by my mauve eyeshadow and ruby red lips.

"Oh my fucking God you are beautiful!" Eddie whispered and lowered his lips to mine.

I tried to push my hand between us to arouse him further but he was rubbing his cock against my stocking thigh as he had done earlier in the evening. I pushed back against him, encouraging him, responding to his kisses with false passion, hoping I could make him ejaculate against me.

He moved on top of me again and to my horror I felt his strong hands pull my calves up again, bending my knees so he was between my legs with my heels flat on the bed. I tried to push myself down into the bed but he forced his hands under my buttocks and lifted my arse clear of the bed. In a swift movement he grabbed two of the pillows from the many that were scattered around my 'work bed' and positioned them under the small of my back. I knew what was coming next as he reached down to my stockinged calves and pushed upward so that my knees came up almost under my chin.

I was terrified about what was to come next but remembered the advice Carmel had given me. I kissed Eddie deeply, my arms locked around his back. I felt his hard cock punching at the thin gauzy nylon panties that were the only thing between Eddie's erection and my puckered anus. I broke the kiss and reached underneath the pillow under my head; my hand came in contact with a cold hard tube.

I pulled it out and glanced at the object in my hand; it was a tube of KY jelly. Eddie followed my gaze.

"Please," I whispered.

Eddie snatched the tube and flung it across the cell.

"No Michele, not the first time. I want your virgin arse without any lubricant except mine!"

With that Eddie clamped his lips over mine again and his tongue assaulted my mouth. I felt his grip tighten on my legs, pushing them hard against my body, forcing my pantied arse high in the air, supported by the pillows under the arch of my back. He thrust forward with his rock hard cock and I felt it tear through the flimsy nylon of my see-through panties and slam against my sphincter.

I wanted to scream but he clamped his mouth tightly against mine, kissing me hard but keeping his tongue out of my mouth for fear of me biting it. Eddie started to push hard against my puckered ring gripping my legs even tighter. I felt my sphincter stretch as Eddie's glans began to invade my arse; the slight lubrication from his pre-come easing the passage only slightly. I felt a pain that was almost unbearable as Eddie continued to push against me. He was still kissing me but grunting at the same time; his breath exploding in little gusts between my lips.

The head of Eddie's penis was now just inside the entrance to my back passage and my sphincter clamped tight around his shaft. There was now no lubrication whatsoever as Eddie commenced to rape me. He pushed into me slowly, forcing his engorged member deeper into me. The pain was excruciating and I began to cry. I couldn’t help it. The fear, the humiliation, the pain; it was too much.

Large tears ran down my cheeks leaving trails of mascara as I began to sob in earnest. Eddie released one hand and bought it up and slapped me hard against my face.

"Stop that fucking shit right now!" he demanded.

"You've been a good girl up until now Michele, so just take it. Take it!!!"

He replaced his hand on my limbs and continued pushing into me. I knew now that all I was going to get was more pain unless I relented and assisted Eddie in his rape. Passive compliance was doing nothing but causing me agony. I concentrated and forced myself to try and relax the muscles creating the resistance to Eddie's cock as it intruded deeper into me. It was hard to do but I was able to make my inner passage muscles relax and suddenly Eddie's cock slid about four inches into me.

More pain now as the thicker part of his member tried to force itself still deeper into me. Eddie was panting now and was supporting his weight on his forearms that held my legs locked to my body. He was looking down so he could see his penis disappearing through the hole he had forced in my panties as it buried itself into me. Then he looked at my beautiful face, the makeup running from my tears.

"Oh yeah, this is so good!" he groaned and gave a mighty thrust.

As I felt the thrust coming I forced myself to relax and Eddie's hard cock thrust in all the way, deep into my bowels. His scrotum bounced against the soft nylon covering my arse cheeks and as he ground his cock inside me his balls rubbed against my slinky nylon panties.

I screamed, the pain was the most incredible thing I had ever felt. I tried to stop but one long agonising scream escaped me. Eddie lifted a hand and I knew he was going to belt me again. I did the only thing I could. I raised the leg that he no longer held and wrapped it around him; then I encouraged him to release the other leg so my that my legs were locked around his waist, the shiny high heels pointed to the ceiling.

I pulled his lips down to mine and thrust up to meet him and I slid my tongue into his mouth. I started to fuck Eddie McManus! At first the pain was so bad that I was sobbing into Eddie's mouth as we copulated. Eventually though, enough of his pre-seminal fluid had leaked so that it slightly lubricated my anus. Although it felt immensely uncomfortable I was able to bear the pain and concentrate on trying to get the rape over and done with.

I bucked against Eddie matching his thrusts and getting into his rhythm; I scrunched my panty ass against his scrotum as he slammed his cock home inside me and rubbed my stocking legs along his back to excite him further. My arms were locked around his back and we both kissed passionately between our gasps for breath as we rutted.

I felt Eddie quicken his pace and he plunged harder and faster, I worked hard to keep up with his rhythm and held his face in my hands and kissed him all over as my legs remained locked around his back. I eased my legs down slightly and dug my high heels into his sides to stimulate him further, I just wanted this to be over.

Then, just as Eddie was moaning and running his hands up and down my stocking legs; I guessed he was approaching his orgasm; a strange thing happened. During his thrusts I began to feel a pleasant warm feeling deep in my bowel. My penis was beginning to stir in the soft nylon of my panties, encouraged by the pressure of Eddie's body against mine as he fucked me. What the fuck was happening? Then I realised, I had read about this somewhere, stimulation of the prostate gland.

'I am not enjoying this! I am not enjoying this!! I AM NOT ENJOYING BEING RAPED!!!' I thought to myself in terror!

Eddie gave one huge lunge and pushed his cock fully inside me, he ground his balls against the silky fabric of my panties and madly stroked my stockinged thighs. He clamped his lips hard against mine and I felt his hot seed expel itself inside me. His cock convulsed and shuddered.

I had an uncontrollable reaction; my high heels drummed on Eddie's back as I lifted my arse up off the pillows to push as hard as I could against him. My tongue lashed around wildly in his mouth and I sucked his tongue deep into my mouth. My sphincter spasmed and my back passage convulsed against Eddie's ejaculating penis. My prostate pushed out rings of pleasure moving through my body in waves. I ejaculated into my panties; I wasn't even erect although my flaccid penis was pushed hard against Eddie's torso, the soft silky nylon of my panties caressing my soft member trapped between us.

We lay like that for what seemed like an eternity as our mutual orgasms subsided, gradually relaxing our fierce grip on each other and our kisses becoming more delicate and soft.

Eventually Eddie eased himself out of me and I felt the strangest feeling as my arse muscles remained relaxed and my sphincter dilated. I felt Eddie's spend leak from me and slowly seep from my arse into my torn panties. Eddie sat on the edge of the bed his member slowly deflating. He reached out and caressed my cheek with the back of his hand then bent and kissed me tenderly.

"That was lovely Michele," he whispered a genuine smile on his face.

I was still in shock at my response, trying to rationalise it. It was just my body reacting to a stimulus; 'I DID NOT ENJOY BEING RAPED!!!' I kept this mantra going over and over in my head.

Then Eddie looked down at my body and noticed the semen pooled at the front of my panties. My semen! He looked down at his tight belly and saw a slimy stain that was the result of my ejaculate spread there when he had pressed his body against me.

I watched the terrible storm brood in his eyes as he reached out and smashed me across the face.

"You dirty Cunt!!!" he screamed, and pushed my face into his belly.

"You lick that disgusting mess off my body before you lose some teeth!" he bellowed, rubbing my face against his belly as I made a vein attempt to lick my own spend off his stomach.

He pushed me back on the bed, my makeup ruined, mixed with semen and tears and smeared all over my face.

"Now get yourself cleaned up and get changed you filthy whore; you're open for business!!!"

 

To be continued……………………………………………………………………………..

The owner was definitely waiting on her, because they wasted no time getting it on.  Someone mistakenly (yeah right)touched the intercom button giving me full verbal access to what was going on.  I heard what sounded like kissing at first.  I heard the owner say that she missed her kisses but most of all missed "this."  I knew right away what she was talking about.  That cock had a mesmerizing effect.  The owner must have went right to work on that rock hard cock, because I heard Leslie telling her how good her mouth felt.  After a little more sucking, Leslie told her that she was ready to ram deep into her pussy.  The next thing I heard was Leslie asking her if it felt good and the owner screaming out "yes, yes".  By that time I had taken hopped up on the counter and was using two fingers in my pussy imagining that cock was going inside of me.  Oh how I wanted it inside of me.  After a few more minutes I heard Leslie tell her that she was "coming."  I heard moaning and grunting and the owner telling her to "give it to me."  After Leslie had finished coming and had plopped our of the owner's pussy I heard Leslie tell her that she wanted their "cum" to dry on her cock.  The owner obviously was about to  assume the position between the those beautiful legs.  The owner told her "okay" with a confused tone.  I heard the owner say she was going in her bathroom to take and shower.  Leslie kissed her goodbye and said she was headed back home and would shower then.  As I was hopping down off of the counter, I heard the intercome cut off and a few seconds later Leslie walked out of the office with a wicked smile on her face.  She walked straight to the dressing rooms and becked for me to follow her.

By the time I arrived in the dressing room, she was already sitting on the bench with her skirt (after our first encounter, she told me that we would always skirts to work for easy access) raised and her legs spread wide with that COCK hanging and begging for me to suck.  She stopped me as I was walking towards her and asked me "how bad do you want it."  I told her "I want it "bad".  She told me to get on my knees and crawl to her.  I was happy to oblige.  I got down on my knees and crawled to that COCK that I knew was covered with a mixture of her cum and our owner's cum.  When I arrived between her legs I grabbed and gobbled her cock so fast she laughed and told me to slow down.  I couldn't because it tasted so good.  The mixture was intoxicating and I was loving it.  As I was sucking she was talking dirty to me and asking me if I enjoyed listening to their sex adventure.  I nodded "yes" not wanting to take her cock out of my mouth.  After a few minutes of sucking, she stopped talking and gradded my head.  As she was fucking my mouth, I gagged a few times, but I didn't stop.  When she told me she was coming, I locked my jaws around that COCK because I wanted every drop of cum.  She came so hard I couldn't contain her in my mouth and it slipped out and spewed all over my face.  When she finished, she quickly leaned down and started kissing me with a passion that I have only felt with her.  Leslie licked up every drop of her cum that was on my face as I lifted up on the bench next to her.  When she finished licking, she looked me in the eyes and told me that she had to leave but wanted to satisfy my wet pussy.  With that she put her hand under my skirt and dipped her finger in my wet pussy, then took her finger and put it in her mouth.  She kissed me agian, told me to come to her house when I got off and with that she left.  As I straightened myself up and was headed out of the dressing room, I ran into the owner.  She had a very satisfied look on her face.  I had the same look on my face.  Just sucking Leslie's cock satisfies me.  I went to the bathroom, got myself off and washed up before the store opened. 

Later in the day while I was waiting on a customer, the phone rang.  It was Leslie and her voice made my pussy twitch.  She asked me if my pussy was still wet.  I told her "yes".  She told me that her cock was rock hard and waiting for me.  When she said that it felt like I was about to have an orgasm, but I had to keep myself composed in front of the customer.  She told me that she was also going to see about us having a threesome with the owner.  With that she hung up.  I was weak at the knees.  I was grateful that the customer was engrossed in a conversation on her cell phone, so she didn't notice me.  I couldn't wait for my shif to be over.

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