er looks had changed some too.  She wasn't wearing glasses any more.  She had also let her hair grow long instead of keeping it short.  I wouldn't say that she is drop dead gorgeous, probably just about average. I was glad she came down though.

That night we had all gone out to dinner at Outback.  As we were walking out I asked my dad which hotel Lisa and my grandmother were staying at.  He told me they weren’t.  They were going to stay with us.  I was a little confused, because we had a nice size house, but every room was being taking up.  I know I didn't want to sleep on the floor.  Dad said that my sister was going to sleep on an air mattress in my brother’s room.  My grandmother was going to sleep in my sister’s bed.  I then asked him what about Lisa?  He kind of gave me a strange look and said that she is sleeping in my room.  I looked at him and told him that I wasn't happy about it.  I told him that I go out at night and come home early in the morning.  I hated to be wakened by anyone, let alone my cousin.  With that I was off to a party with some friends.  What you have to understand was that I had already packed up most of my stuff.  I was getting ready to move to an apartment with a friend a few days after graduation.  The only things that were in my room was my bed, TV, and my parents old sofa.  They had just bought new furniture and I was getting the old sofa.  The sofa is what Lisa was sleeping on. 

Anyway, I got back home at about 2am .  I was a little surprised to see Lisa still up watching TV.  She was watching Dukes of Hazard.  She asked me what I had been doing.  I told her I had gone to a friend’s house and everyone there was just hanging out drinking and having a good time.  I told her I would be right back and went to the bathroom to brush my teeth and change into some shorts.  I laid down in bed and Lisa turned the tv off.  She was asking me more questions like what I thought it would be like to play college football (I’m 6'1 280lbs).  I then started asking her some questions.  They were all stupid questions, until I asked her if she had a boyfriend.  She said no.  She said she wasn't to keen with guys.  She didn't think she was pretty enough for a guy to like her.  She also didn't like her body.  She said she was taller than most of her friends and most of the guys.  She also said she didn't like her boobs.  She said they were just like little mounds with a Hershey kiss on top.  I couldn't believe she was telling me this.  I knew what she meant though.  She didn't look like she had any boobs at all.  The talk didn't get much further than that before she said she was tired and wanted to go to sleep.

The next day I went along with my usual business.  I saw my family off and on.  I was so busy.  For some reason or another though I couldn't stop thinking about what Lisa was telling my last night.  I found my self not being able to wait until tonight.  I had some other questions to ask her. 

Night came and I found my self at home earlier than I usually would.  I got ready for bed.  I noticed Lisa was watching tv and she didn't seem that interested in talking.  So I took a bold first step and knowing the answer already I asked her if she was a virgin.  She hit mute on the remote control and looked back at me puzzled.  Why do you ask that? she said.  I told her I was just curious after what we were talking about last night.  She told me yes she was still a virgin.  She then sat up on the sofa and asked me the same question.  When I told her no, she looked puzzled again.  She said that she thought you had to wait until your married to have sex.  See, I later found out that my grandmother is the one who told Lisa about sex.  Being that my grandmother is very old school, Lisa thought you had to be married to have sex.  I told her you don't and she still looked puzzled. 

Lisa started to ask me a lot of questions about sex.  Like how it feels?  What’s it like?  Lisa was really starting to turn me on.  I had to pull the covers over me to keep her from seeing my hard on from the light of the tv.  I then got real brave.  I told her I could answer all of her questions, but that it would be different.  I could only tell her how it felt for me, from a mans perspective.  I didn't know how it would feel for her.  I then asked her if she had ever kissed a guy before.  When she said no I jumped on the opportunity. 

I told her to come over to me and I would show her what it is like to kiss a guy.  She came over and sat down beside me.  I leaned into her and gave her a kiss on the lips.  She seemed really scared.  I told her there wasn't anything to worry about.  I then told her the next time I go to kiss you to slightly open up your mouth.  When I kissed her again she did as I said.  I put my tongue in her mouth and started to French kiss her.  She really started to get into it.  Then out of instincts I started rubbing her boobs on the outside of her t-shirt.  It didn't take her long to realize what I was doing before she pulled back.  I asked her what was wrong.  She said that she didn't want to do this.  That she wasn't ready to have sex.  I told her we don't have to have sex, but that we can fool around.  She said it's all the same thing.  I told her it wasn't.  Finally after thinking it over for a minute she said as long as we don’t have sex.   I told her we wouldn’t.   With that I leaned in and started kissing her again.   After a few minutes of kissing I started to take her shirt off.   You could tell she really didn’t want to.   She kind of fought it and then finally gave in a let me take it off.    When I looked down at her breasts I noticed that she wasn’t lying.   She really didn’t have much in the way of breasts.   Her nipples looked like little Hershey kisses too.   They would puffy and sticking out.   She quickly took her hands and covered herself up.   I told her not to, that I thought she was beautiful.   She said she would feel more comfortable if I showed her my penis.   I said ok and took my shorts right off.   I would say that I am average in size.   She looked at my penis and was kind of taken back by it.   She said she had only seen some in magazines.   She asked if she could touch it.   I told her she could.   With that she stuck her hand out and touched the head.   She said it’s so hard, but soft.   I then started to show her how to jerk me off.   I guided her hand to the base of my cock and told her to move her hand up and down.   It felt so wonderful.   While she was doing this I was playing with her breasts.  

After a few minutes I asked her if she wanted to try something else.   She said sure.   I told her I wanted to teach her how to give a blow job.   I told her to lean down and kiss the head of my penis.   She did and when she sat up she said she tasted something.   I told her it was called pre-cum.   It acts as a lubricant if you’re going to have sex.   I then told her to open her mouth and to put my penis in it.   She said it seemed kind of gross.   I told her to trust me.   When she got some of it in I told her to close her mouth.   I then told her to start sucking on my cock with out using her teeth.   To move her mouth back and forth and to use her tongue.   She was really driving me crazy.   I was getting ready to cum, but I really didn’t want to say anything to her.   I wanted to shot in her mouth and hope that she swallows it.   I looked down at her and told her to pick up speed a little.   I then told her I was close to Cumming and that I wanted to come in her mouth.   I told her to keep going and that when I cum to swallow it.   If she couldn’t do it then I told her to spit it in the trash can beside my bed.   She went at it for another minute of so and I started to feel my balls tighten.   I didn’t even warn her.   I just grabbed the back of her head and brought her mouth down over my whole cock.   I shot a few ropes of cum in her mouth and I could start to hear her gag.   I let her go and she ran over to the trash can and spit it out.   I had a glass of water on my night stand and let her use it to rinse her mouth out.   When she got back I could see she had a few tears running down her eyes.   I asked her if she was ok and she said yes.   She said that she was finished for tonight, but that we could mess around again tomorrow.  

Tomorrow night came and we started off messing around again.   I was completely naked and she had her shirt off, but her shorts on.   This time I laid her down on my bed and started to kiss her.   While I was kissing her I kept thinking about how I could get her to have sex with me.   I wanted her so bad.   I wanted to take her virginity.  

While I was kissing her I slowly made my way kissing her down her neck to her breasts.   I focused on them for a while.   I could her Lisa start to moan a little.   That is when I decided to go further.   I started kissing my way down her stomach to her belly button.   When I got to the elastic of her shorts I slowly started to pull them down.   She quickly grabbed them and pulled them back up.   She said she didn’t want to play anymore.   I then asked her if she remembered how good I felt after she gave me a blow job last night.   She said yes.   So, I told her that I wanted to give her that same feeling tonight.   I told her I wanted to lick and kiss her pussy and make her cum.   I told her it would be the greatest experience in her life.   I started to kiss her breasts again and she reluctantly said alright.   With that I slid her shorts off.   I told her she needed to open her legs wide.   She did and I put my mouth down by her pussy.   I could tell she was already wet.   I started to eat her out.   I began to really focus on her clit.   She was starting to really get in to it.   She was grabbing my head and holding me down there.   I just kept thinking man I got to get my cock in there.   While I was eating her out I decided to put a finger in her.   She was really tight.   She never said anything so I just kept going.   I could tell she was getting close to an orgasm.   Finally she came.   I looked up at her face and she had more tears running down.   She said she was so happy.   She had never felt something that good before.   She told me that she felt she was starting to have feelings for me.   I told her the same thing.   I tried to position my self to get ready to have sex with her.   I had my cock lined up to enter her.   I was looking at her eyes telling her how beautiful she is and kissing her passionately.   I then told her that I wanted to have sex with her.   She said she was scared.   I asked her of what?   She said she heard that it hurts.   I told her sometimes it does at first, but not for long.   She then said that she didn’t want to get pregnant.   I told her I didn’t either.   She asked if I had a condom.   I told her that I didn’t.   She then said that she wouldn’t do it.   I was really upset.   I asked her if we could have sex and I would just pull out before I came.   She still said no.   I then asked if I could just put it in and take it out.   She really didn’t want to and was making it known.   After a lot of begging she finally gave in to me just putting it in and then pulling out.   They whole time I kept thinking maybe she will change her mind once we started.   So, with that I slowly began to push inside of her.   I got all the way to her hymen and she said ok, you were in now get out.   I told her I was barley in her and that I wanted to be in her all the way.   She said she didn’t want to do this anymore and for me to pull out.   I told her to stop being a baby.   With that I pushed through and broke her hymen.   She started to scream, but I just put my hand over her mouth.   I could see the tears running down her face.   I felt bad for what I did, but I was too lost in the moment.   I just laid there with my cock all the way in her until she stopped screaming.   When I moved my hand away she told me to get out of her now.   I told her I couldn’t.   I told her she was the tightest girl that I had ever had sex with.   She said we are not having sex, that I promised to just put my cock in and take it right out.   I then told her that I changed my mind.   I wanted to go all the way.   She started to cry.   I told her not to worry, that it would all be over in a little bit.   She then told me that she would scream.   I told her she would be sorry if she did.   With that I slowly began to fuck her.   In and out, in and out I went.   I kept telling her how great she was.   That she was the best I had ever had.   She was just crying.   I then started to pick up speed.   I could hear my balls slapping against her butt.   I was lost in another world.   Finally I could feel my balls tighten up.   I knew I was about to cum.   I also knew that I didn’t want to pull out.   I wanted to feel what it was like to cum in a woman without wearing a condom.   Just then I shoved as deep in her as I could.   All I could do was say “Lisa, I’m Cumming, Lisa I’m Cumming.”   I just emptied my cum into her.   I just collapsed on her.   I had never cummed so hard in all my life.   When I pulled out of her she quickly got up and put her cloths back on.   She ran over to the sofa and lay down in a fetal position crying.   I just sat up and told her that there was nothing to cry about.   I told her she was very good.

Nothing happened again after that night.   Lisa and my grandmother left two days later.   Thinking back after they left, I thought maybe I shouldn’t have done what I did.   It was too late though.   You can’t change the past.  

A couple months later I had to go up with my dad to see my grandmother.   She wasn’t doing to well.   When we got there I figured I would see Lisa.   When I didn’t I asked my grandmother where she was.   My grandmother told me that she had started messing with boys and got her self knocked up.   Grandma said that she is at some special school for young pregnant mothers.   She then ventured to say that Lisa had claimed to have only had sex once.   So, was the baby mine.   I guess I would find out in seven months.

; She isn't gorgeous, but she is really beautiful.  I would guess she had about a C cup breast size.  She also has a little meat on her bones, but not much to say she is overweight by any means, mostly just somewhat leftover baby fat.

 

 

Me, my name is Matt.  I am 27.  I am 6'0 and about 280 lbs.  I am a pretty stocky and big guy.  I have short brown hair and hazel eyes.  I am pretty average in penis size I would say, about 6 inches and somewhat thick. 

 

Ok, so this night was like all the other nights so far.  After the training was over we would all go to the lobby of the hotel and enjoy the free drinks they were serving.  This usually lasted about an hour to an hour and a half.  After this, most of us would walk to one of the many restaurants in the area.  This time, however about 7 of us decided to order room service and go up and just drink and talk in Todd’s room.  Todd is a really big drinker and even brought a suitcase with just beer and alcohol for everyone. 

 

After dinner, we continued to drink and some of the people were playing an Xbox that Todd had brought.  With people starting to get really tipsy, all the funny stuff started happening.  Here I was in a room full of people I worked with who acted one way at work and was now totally different.  On this one instance, I was taking video with my cell phone and I happened to catch my manager Sandy. She was what I would say was drunk.  She walked up to Todd and slaps him on the ass.  Todd turned around and told her if she liked that then she would love touching this, and stuck his crotch in her face.  She gave it a kiss on his pants and sat back against the wall.  After seeing that, I started to show some of the guys who didn't see it happen. 

 

 

Sandy had since gotten up and came over to the couch where I and another guy were sitting.  She asked us what we kept watching on my cell phone.  I didn’t tell her anything at first, but she kept bugging us.  I finally told her that I recorded her little incident with Todd.  She couldn’t believe it.  She got a little mad at first and told me to delete it.  I told her that I couldn’t.  It was too good.  She then told me to give her my phone, which I didn’t.  She then tried to grab the phone from my hands.  I kept moving it away from her.  She finally got so mad she sat straddled on my lap trying to get the phone from me.  She still couldn’t get it.  It didn’t take very long with all the moving she was doing on my lap to get me excited.  I started to feel the bulge growing and I had a feeling she would to since I was in sweat pants.  I just for some reason hoped no one else would notice.  After about five minutes of this, and knowing she was drunk, I figured I would take this to the next step.  I said if you want my phone that bad, then you will have to get it.  I then proceeded to stick the phone in my pants between my cock and my balls.  She really didn’t do anything at first and I thought I had just blown it. 

Then, out of no where Sandy looked around the room to see if anyone was watching.  When no one was paying attention she put her right hand in my pants to get the phone.  Fumbling around trying to get it, she kept brushing against my cock which got me even harder than I was before.  She finally grabbed my phone and went back to where she had been sitting to try and delete the video.

 

 

A half hour had gone by and everyone was still drinking and playing Xbox.  I was getting kind of tired, so I told Todd and some of my other friends that I was going to go back to my room to get some sleep.  As I walked to the front door Todd stopped me and asked if I could help make sure Sandy gets to her room ok.  She hadn’t had anything to drink in a little while, but I could tell she was still a little drunk.  I told Todd that it wouldn’t be a problem. 

 

 

So, I got Sandy down to her room ok and was on my way out when I remembered that she had my phone.  I went back into her room to get it.  Luckily I still had her key she gave me when I first helped her in her room.  I opened the door and walked through the living room part to get back to the bedroom.  The door was mostly closed.  When I peeked through the crack of the door I noticed she had taken her shirt and pants off and was just laying across her bed in her bra and panties.  I started to get aroused looking at her.  Just then, I noticed she put her right hand inside of her panties.  She was really starting to work her self into a freenzy.  I tried playing it off and just opened the door and told her I forgot my phone, that I needed it back.  She jumped up and tried to get under the covers really quick.  I asked her why she was freaking out and got under the covers? I told her she wasn't wearing anything less than the bikini she wore to the pool.  She told me that she was going through a rough time in her personal life.  I sat down on the edge of her bed.  She started telling me that since her last daughter was born a two years ago that her husband and her had only had sex maybe a handfull of times and that was when he would come home drunk.  Also, that she hadn't had any sex in seven or eight months.  She also said that she believes he was having an affair with a woman he works with.  Sandy started to cry and said that maybe it's because she isn't pretty anymore.  I told her that can't be, that she was beautiful and that her husband was a very lucky man.  She told me that she didn’t think so, but I told her she shouldn’t think that because any guy would be lucky to have someone like her. 

 

Sandy, still crying started to tell me that when she was on my lap back up in Todd's room, that she got really wet from kind of grinding on me to get my phone.  Then when I stuck it in my sweatpants that she really didn't know what to do.  Sandy told me that she got married right out of highschool because she got pregnant the end of her senior year.  She then said she had a miscarriage, but still married the guy who is now still her husband.  She said he is the only man's penis that she had ever touched or seen that wasn't in a picture.  Then when I stuck my phone in my pants she didn't know what to do.  She said between the alcohol and the fact she was horny and wet, she went for my phone.  Sandy said she intentionally grabbed my penis a couple times to see how big it was and what it felt like. 

What happened next, I will never forget.

Sandy, with tears still in her eyes asked me is she could see my penis again.  I looked at her for a second and thought if this is something I want to risk.  I asked her if she was sure she wanted to see it.  She thought for a moment and then said yes.  So, I stood up from her bed and kicked my shoes off.  Then I pulled my sweatpants down to reveal my thick six inch cock.  I stepped out of my sweatpants and just stood there not know what I should do next or what would happen.  Sandy just sat in her bed looking at my dick.  I decided that I wouldn't hamper her view in any way and then took my t-shirt off and threw it on the floor.  So, there I was butt-ass naked standing in my manager's hotel bedroom.   

Sandy pushed the covers off of her and stood up next to me.  I had all these things running through my head when she did that.  I couldn't stop thinking how bad I wanted her.  I didn't care if she was my manager, or was ten years older than me, or that she was married and had two kids.   Then standing there Sandy looked at me and asked if she could touch it.  Without hesitation, I said yes.  There Sandy stood, right in front of my naked body and her in her bra and panties reaching out her hand to touch my dick.  She sent shivers down my spine when her hand first touched it.  I just closed my eyes for a second and take a deep breath.  She started to slowly stroke my dick.  I opened my eyes and looked down at her.  We stood there with her stroking my cock in her hand and just staired into each others eyes.  When Sandy started to speed up her rythem, I couldn't help my self so I leaned in a kissed her.  Her lips felt so good.  They were as soft as peaches.  Sandy was supprised by this to say the least.  I think it kind of hit her, where I wanted this to start going.  She broke the kiss and started to tell me how wrong this is, and that I shouldn't kiss her.  I asked her how that could be wrong, but her jerking me off was ok.  She looked like she had all these things, these feelings running through her head.  She told me how horny she is, but that in her eyes, she couldn't have sex with someone that isn't her husband.  For one, she said it was wrong.  Second, she said she isn't on the pill and didn't want to become pregnant.  She told me if she did get pregnant her husband would definitly know she was cheating on him.  I told her that she shouldn't have sex with anyone but her husband.  That we didn't have to have sex to have a good time.  I told her that all I wanted to do was please and pleasure her.  Make her feel good and special.Sandy looked like she was about to cry.  I didn’t know what to do, should I put my cloths back on and leave?  Step into the other room?  I just came to the point where I just said fuck it.  I walked right up to her and started kissing her again on her lips.  I was a little shocked when I could tell she was kissing me back.  I really didn’t expect her to.  So there we are, standing in her bedroom kissing.  After only a few minutes our kissing got more passionate, I got a little braver and started rubbing my hands on her breasts.  She didn't seem to object to that so I then reached around her back with my right hand and unhooked her bra.  I then proceeded to pull her bra off.  After I had it off and her tits were free, my hands were all over them.  It wasn't too long after I had her bra off that I decided to start making our way over to her bed.  Once I had gotten her laid down on her on her bed, I started kissing her again, but this time when I kissed her I moved over and kissed the left side of her neck and her left ear.  This really started to set her off, for the first time I heard Sandy start to moan as I kissed her neck.  I slowly started to work my kissing down her neck to her breasts.  I could tell that she was really getting heated.  Her nipples were so perky; I just kept going from one breast to the other sucking and kissing on them. 

After doing that for a little while, I decided it was time to move down.  I kissed my way down to her belly button, then down to her panty line.  I sat up and grabbed one of her legs and started kissing the inside of her thigh.  As I was doing this, I placed my hands on her panties and started to pull them down off of her.  At first, she put her hands down to stop me.  I couldn't think why she would go this far, and not want to finish.  When she put her hands back down to stop me a second time, I leaned up on her and started to kiss her mouth again.  While on top of her and kissing her, I reached back down and started to pull her panties off again.  She started to object this time, but I leaned over and wispered in her ear how all I wanted to do was pleasure her, and that I wanted to taste her juices.  She stopped objecting and let me finish pulling her panties off.  Once I had them off I glanced down at her pussy.  She was extremely wet.  Her pussy looked so soft and sweet.  It had a little hair around the top.  I laid back on the bottom of the bed and I spread Sandy’s legs and started to kiss around her pussy.  It didn’t take long before I felt her getting even wetter.  As I was eating her out, I could hear Sandy’s soft moans.  It was really turning me on.  I started letting my tounge rub around the outside of her lips and sometimes brushing it against her clit.  After a couple minutes of this, I focused just on her clit.  Sandy started to go crazy.  Right before I thought she was going to have an orgasm, I stopped.  She looked at me a little disappointed.  She asked me what was wrong.  Nothing, I told her and I started to kiss my way back up her stomach to her breasts, then her mouth. 

While kissing Sandy, she started to wrap her legs around the small of my back.  Lost in the moment and not really thinking with anything but my dick, I grabbed it and started to line it up to her pussy.  I started to rub the head of my dick all over her opening.  She was still so wet, so in one quick thrust I now had my cock inside Sandy's pussy.  I was in heaven.  She was so wet, and so warm, not mention somewhat tight.  When I did this Sandy kind of let her grip on me go.  She let her legs fall and rest back on the bed and took her arms that were wrapped around my neck off.  As I started to slowly pull out, I sunk right back in.  She looked at me and asked me what I thought I was doing.   I then leaned back down and started kissing her.  I told her how could something so wrong, feel so right?  As I continued my slow rythem in and out of her, she asked me if I atleasat had a condom to put on.  I told her I didn't, that I hadn't expected anything like this to happen.  She told me to get out of her, that we couldn't go any further.  I did what she wanted.  I sat up on the edge of the bed.  I asked her if she liked what I was doing and she told me it was the best feeling she has had in a very long time.  But she didn't want to get pregant so we couldn't go any further. 

I asked her if I promised to pull out early and let her finish me off in her mouth or jerking me off would she do that.  She thought about it for a second and said yes.  So, I climbed back on top of her, my erection never have gone down and grabbed my cock and lined it up to her entrance.  I slowly slid into her.  As I did, Sandy let out a moan that was heavenly.  I starting a nice slow rhythm and would increase it periodically.  After about five minutes of this, I told Sandy to get up and turn around on her hands and knees.  I slid back into her from behind.  This time I was working her pretty good.  I was really going at a faster pace now.  Sandy was also moaning pretty loudly.  After getting her from behind, I told her to lie back down on her back.  I wanted to finish everything like this.  I grabbed her legs and put them over my shoulders.  I slid back into her and knew that it wouldn’t be long before I would have to cum.  We were both pretty hot by now.  We were both sweating something good.  I was reallying giving Sandy all that I had.  My pace was so fast right now, that she would let out a little scream everytime I would plunge into her.  It wasn't long before I could feel that tingle in my balls that told me I was close to cumming.  I told Sandy that I was about to pull out. 

 

 Sandy asked me if I could hold out for just one more minute, that she was almost there.  I told her I would try and just kept pumping.  All of a sudden I felt Sandy’s pussy clinch up and I could feel her cumming.  That was all it took.  I couldn’t hold it anymore.  I wanted to be as deep as I could, so I lifted her ass a little more off the bed and I just pushed as far into her as I could and started cumming.  It was one of the best feelings ever.  I didn’t think that I would stop cumming.  I just kept filling her with my cum.  When I finally finished, I laid her back down on the bed and rolled off of her.  I could start to see my cum leak out of her pussy.  I just laid down beside her.  Sandy was still trying to catch her breath.  It was after she caught her breath that things got interesting. 

 

 

 

 

More to come if the story is well liked.