It was the summer I turned 18. I was really into swimming, not to compete with anyone but the clock. I swam my ass off every day, so I was in outstanding shape. I was 5' 7", 120 lbs, I was lean but not really cut. I was smoooth. Really smooth because of the swimming. I shaved or used hair removal products over my entire body except for the hair on my head. I used to get reamed about it by my freinds, but the girls loved it. In my high school career, which I had one year to go, I was sexually active with a few girls, but no steady ones. I was kind of leary of commitment. But the girls loved me, with my long hair and blue eyes with long eyelashes. Even a couple of my female teachers told me the would marry me if our ages were closer.
I lived in, not a small town, but not a big one either. It was big enough that you didn't have the " Everybody knows evrybodys business". But it was small enough that the city directors decided there would be no trash pick up, so us citizens had to haul it to the city dump ourselves. This where my odyssey began.
It was the begining of July and it was hot as hell. Our garbage was just about overflowing and begining to reak, and it was my house chore to haul it to the dump. One morning after my swim work out, I put the smelly garbage cans in the back of my truck and was off to the dump. The dump trips didn't bother me, they were actually pretty cool. See, after I'd dump our garbage, I'd ponder around, because people throw away some of the most interesting shit. The people that threw out some of this shit, you really know a bit about them, just from what they thought was trash. On that trip, after I dumped my garbage I was looking around for interesting shit when I came across a box that had VHS tapes ( in good shape ), and a stack of magazines. There were 10 tapes on top that weren't marked, and a good stack of magazines underneath. I reached in and tried to see what kind of magazines they were, but it was hard because of the tapes on top, but they looked like porn. I wasn't going to take all the shit out of the box at the dump just to find out either. But with all the unmarked tapes , and maybe some porn magazines, I was interested, so I put the box in the truck and headed home with my find.
I didn't discover what my find was right away. I put the box in my closet, and had to go to my job at the local super market. I got home later that evening, and found a note from my folks that said they went dancing at the local shitkicker honky tonk. That meant they wouldn't be home until tomorrow afternoon, because they wouldn't drive after drinking ( which they tended to do alot of when they were dancing), so they stayed at the little motel attached to the honky tonk ( what a town, huh, like something out of the 50's ). I trew the note away, and took a shower and jerked off thinking about one of my female teachers. After the relieving shower I ate some dinner and retired to my bedroom and some TV.
After about an hour I remembered the box in my closet. I got it out, and took every thing out. Well, I was kind of dissapointed in the magazines. They were all gay porn. But kind of different gay porn. There was a stack of about 20 magazines that were about older men; then older men with younger guys. I thought there were also some of older men with younger girls, but with a closer look, it was older men with younger guys dressed as girls. I'd never seen porn like this before. At first, I was kind of turned off by it, but then all of a sudden it was like I couldn't stop thumbing through them. I stopped and thought about it, and got a little confused. I wasn't gay, I loved women. But, my brain was still trying to rationaize it; I loved sex, and sometimes a little kinky too, and this was sex, a different expanded kind of sex, and damned if it didn't intrigue me, because I'd never really been exposed to it, or even once thought about it. "Hmmm, I thought........" So, I kept slowly going through the magazines.
After about an hour of getting a bit excited with the magazines, it hit me...... what about the VHS tapes? I wondered what was going to be thrown at me with those? I looked through all the tapes and there wasn't a marking on any of them. I stacked them over by TV and VCR with the rest of my tapes. I took the top one and put it in the VCR and pressed play. Sure enough, it was of older men and younger guys. As the tape played on, it also had scenes of older men with younger guys dressed as girls. Man, they looked just like girls. The make up, the hair, the feminine clothing: girls tight t-shirts, stockings, heels, pumps, and then just lingerie. I looked closer and saw some of the panties they were wearing were like specially made with a cup in the front to contain their erect cocks. A few that were wearing a thicker top, like a short sweater,and appeared to have tits, probably fake form inserts I thought. Anyway, they looked like really hot chicks, no shitin' you there. The older men were different in each scene, same as the magazines, I mean of course they were different people, but of a different genre. Like in the different scenes one would be a businessman, another he'd be a outdoorsman, another he'd be a teacher, etc. Well, as I watched the videos I became more and more intrigued to the point where my cock got hard. And I started to realize exactly what it was in those videos and magazines that was turning me on. I sat there almost all night long watching them. I finally fell asleep. A good deep sleep with no dreams.
Over the next few days I felt strange thinking about the videos and magazines, like it was taboo. But, it being shunned on by society, taboo, was exciting in itself. I'd gone out with some friends to the river fishing and got drunk off my ass. It was kind of like I wanted to clear my head or just bombard it to destroy what I been thinking, even if it was for just a little while. The next afternoon I was recovering from my beverage choices of the previous night. I layed in bed and wacthed the videos. What really turned me on I realized, were a couple of things. The older men. They were like ages of 40 to 60. Most of them were in good shape, even muscular, and then some had a slight belly. Some were hairy, some were smooth. And their cocks..... some fat and short, some thin and long and viseversa. Like I mentioned earlier, I'd never really been exposed to this stuff and now that I had, I liked it, regardless of what "normal" society thought, or what I used to think. If one of those men in the magazines or videos were there with me, nude with his hard cock pointing out at me, I'd have submitted and had sex with him. The other thing that turned me on was the younger guys submission, or the role reversal. The younger guys were playing the female role, they were the woman for the older men. That really was my excitment topper; imagining yourself as a woman as you are getting fucked by a man. In the videos and magazines the older men refered to the younger guys asshole as his boy pussy and his erect cock tied up in that cupped thong was his clit that would get rubbed, mainly by the young guy. But is some of the videos and magazines the young guy would get reciprocated, I mean the older man wouldwould suck cock and get him man pussy rammed. It was like straight gay sex. That kind of turned me on, but it was nowhere near how the role reversal topped my excitment.
Even though I had these new sexual desires, I still loved women, and wanted to have sex with them, fall in love with one, and emotionally connect with her. With my new sexual quest, it was just physical sex. I didn't feel emotional about it, love wasn't involved, just raw physical pleasure.
Well, as a few more days passed I was enhancing my fantasies to kissing, dressing as a girl, and even insserting my fingers into my ass. I even got a slightly thick and long cucumber and after a few rough tries I got it in my tight ass. I learned how to relax my muscles and take it in. I even got to the point where I could move it in and out. As I would move the cucumber in and out, or just move it around in my rectum, I dicovered that it would rub across my prostate and give me a great hard sensation. Then as I moved faster, slamming it into me, the sensations would grow to a climax. It felt just like an orgasm, like I was cummig, but with out the ejaculation. My legs would start to shake and it would be so intense I'd have to stop with the cucumber until it passed. It would last for long seconds too. It was an awsome thing.
I started wondering what I'd look like dressed as a girl. I'd pose in the mirror in my under wear and pactice feminie mannerisms. Being smooth all over helped to. But I wanted to take it further. I drove to the closest "city" and went to an adult shop. I bought a ton of shit: sexy girls clothing, those special panties with the cup, make up, perfume, a book on how to become feminine ( how to use all shit bought ), I bought a couple of dildos, and a few more videos. When I got all the stuff home and while my parents were gone I'd put it to use. After I'd get dressed up I looked hot as hell, I bet I could of walked around town and no one would have recognized me. They would have just stared and thought a new hot chick was walking around. After I'd dress up I fantasize about doing it all with an older man, as rubbed my boy clit and ream my asshole with a dildo. I was having great fun, let me tell you!
After about a week of my new way to play with myself I really started yearning for the real thing. My first thought was to go to the city and hit those certain bars, or the adult book stores, or the cruising parks. But that was way out of the question for me. I mean you don't know who you'll run in to and what their carrying, a gun, knife, or a disease. I figured it would have to someone I knew, which was hard to consider. Over a period of 2 days I carefuly went through a list in my head of older men I knew and would consider having sex with. I went through: my parents freinds, my freinds fathers, teachers, neighbors, men I worked with, men that I saw randomly as acquaintances, hell I even though of uncles. After straining my brain I was kind of at a loss. Trying to have a fantasy about someone you knew was kind of weird, but I gave it a try. I picked out a teacher, the ass. pricipal, my best freinds' dad, and one of my bosses at work. They were all cool to me, but they also had that dominant vibe about them. I could picture them treating me as a girl and fucking me. I wasn't to sure any of them would actually be interested in actually carrying though with it. Plus, how would I approach them, or get their attention to what I wanted to do? I was really stumped.
Though I ran into kind of a wall at that point, but from out of nowhere my oddysey was about come to a climax. I spent another few days having fantisies about the men I picked which I knew. The weirdness about them vanished and I was yeaning fucking hot for them. But I was still stumped on getting their interest in what I wanted. Well, a hot fucking Friday rolled around and I had to work all day at the supermarket. I checked out one my bosses pretty closely that day. I even took a chance and followed him into the bathroom. There were only two urinals, and as he stepped up to the right one and started his business. I stepped up to the left one, undid my zipper, pulled out my cock and pretended to piss. He looked over at me, recognized me and started in. " Damn it's a fucking mad house today...blah blah blah " "Yea" I mumbled. He kept rambling on about the fucked up day and didn't notice me move close in to the urinal, and put my head down as if I was watchig my piss, but I was eyeballing his cock. He was the type of guy that when he pissed he undid his trousers, zipper all the way down, and pulled down the front of his tighty whities to underneath his ball sack. He then put his left hand down flat against his lower stomach and held his cock at its base with just two fingers. I had direct view of his whole cock. He had just started to piss. His cock was long, at least 4 to5 inches. And it looked like it was mabye semi hard because pitched out straight then bent down. It was a fairly thin cock maybe 3 inches around, and it had a thick pointed head. This was as close to a real mans cock I'd ever came, especially now that I was into them. I was so fucking excited, my heart was going into the red, and my cock instantly got hard. I tried pushing my cock to the side so if he happened to glance over he couldn't see it. But he finished pissing, and shook his cock a couple times. And as he did that I was thinking - Please just turn to me with your cock still out, and say " I'd really like to give you some of this." as you hold it and point it up towards me - But it didn't happen that way, my ESP wasn't working that day I guess. He just did up his trousers, walked to the sink and washed his hands. As he walked out he said " See you in the trenches. " I whispered " I'd like to see you in my bedroom. " Now I had to walk around the rest of the day like my stomach was urting because of my raging hardon! When I got home that evening I went straight to my room and tore off my clothes. I didn't bother dressing up, I just grabbed a dildo, lubed it up real good, got on my bed leaned slightly on my right side, pulled my left knee up to my chest and slid that fake cock right up my ass and started reaming it in and out. I started jerking my cock hard while imagining that my my bosses cock was pounding into me! I came pretty quickly. I think I actually squirted a couple loads across the room. I laid there exhausted. Just before I drifted off to sleep I remembered that my parents went out of state today to visit family. I had the house until next Thursday. Six days. I planned on some dress up fun.
The day had arrived, although I didn't know it yet. ( Bet you readers though it was going down with my boss, didn't you.... ) I woke up that morning at around 8. I felt pretty refreshed. I ate breakfast, did a couple chores then wondered into my room. Since the house was empty and locked up, I wanted to enjoy the freedom while I dressed up. I wanted to dress up and get the hottest look I had. I showered, and used the bathroom to dress, with the door open as I enjoyed the freedom. It was as if there was a man waiting for me in the living room. I started to dress. I used my moms curling iron and curled my hair in big flowing curls then I tossed my head around so the curls looked natural and primped up. I put on mascarea, and brownish pink eye shadow. A slight natural base with a slight reddish pink rouge went on next, followed by pink juciy lip stick and gloss on my really full lips. I put on rubber cock rings around the base of my balls and cock, then slipped on a pink special thong with the front jock strap like cup. Over that went a tight pair of red short shorts that showed off my bubble butt and made my hips look round. I slid on some light pink mid thigh stockings. And on top I put on a pink tight girls t-shirt that only went down as far as the top of my belly buton. I used a white girls bandanna with red flowers on it, with about a three inch fold in the front of it to tie from the base of my neck, which I pulled my long curled hair out over, then I slid the front of it up across my forehead pulling my hair back to just slightly forward of the center of the top of my head. Then I pulled out my bangs over my forhead. I went to my room and look at myself in the full length mirror. I outdid myself. It was the hottest I'd ever looked.
I pranced around the empty house really displaying my feminine mannerisms. I was horny as hell, so I went to my bedroom. I got out my long thin dildo and got on my bed. I got on all fours facing my pillow. I held the dildo with my left hand, holding the base of it onthe pillow so it was sticking up in my face. Then I began rubbing my boy clit, my cock was rock hard pressing against thoughs tight ass shorts. I started sucking on the dildo pretending it was my bosses cock. After about five minutes, from my peripheral vision to my left I thought I saw a figure in the doorway. I looked up, and holy shit, my best freinds' dad was standing there grinning. His name was and still is David.
" Oh fuck " I said. I jumped up pulling my comforter up around me. I was freaking out. I was so freaked that I started shaking a bit. I wanted to run but he was in the doorway. So ended up taking a step this way and that way trying to escape the humiliation. Then I remembered I had fantasized about him....holy shit, what fucking mess this is going to be I thought. From the doorway he took a step forward and put his hand out. " Whoa, whoa. Calm down. " he said. I looked up at him kind of pissed now for some reason. " What are you doing here! " I demanded. " Holy shit its you! " he said. " I thought you were some girl in here. " I looked up at him and then just turned around, and walked over and sat on my bed. It was like I was exhausted from being so scared. " Well the jig is up.....I'm fucked. " I said when all I could do was keep my head down looking at my pink stocking feet. He walked over and stood in front of me to the right side. " Ahh is that what you think of me. " That I'm judgemental of people. I thought you might have known me better than that. " He paused, maybe waiting for a reply from me. He didn't get one. He said " Man, I'm so far from judgemental..... listen to me, I mean really listen, if what you do doesn't hurt anyone, and you enjoy and get pleasure from it, whatever it is, I say ok go for it. Look, compared to what I've seen and things I've done your a saint. " I looked up at him. " What have you done? " I asked suspiciously. " Take my word for it. " He said. " Does anyone else know? " He asked. " No. " I said. " Then its just you and me. And nobody will hear about it from me, scouts honor. " He said. " Really? " I asked " I promise." He said as he put his hand on my shoulder. I let out a huge sigh of relief. " Yea, thats it. It's reall y OK " He said. I stood up and walked over to my dresser. " I think it's cool what you're doing. " He said I looked over at him. " You do? " I asked. " Hell yea I do. You've got enough guts to go out and do what gives you pleasure. " He said. Then he added " Plus, it's pretty damn sexy. " I looked over at him as he laid back on his elbows on the bed. " You really think that? " I asked. " Oh yea, what I saw when I came in was really sexy! " he said. " Wait a minute, what are you doing here and how'd you get in? " I asked comically. He said " Your dad asked me to come ver today to fix the box freezer in the mud room, he gave a key. I guess they didn't tell you ,huh? " I shook my head no. " Well " He said " They didn't tell me you'd be here either, I guess it was just luck. " " Luck. " I said. He was just grinning. I could see that slight dominant thing come over him. And the way he was leaning back his levis were streched across his crotch, and yep, there was a nice bulge there. After all the commotion just a bit ago, I felt wore out. But now I was getting excited again, and a damn fine reason for it. He was an attractive man. He was about 5' 9", with lean muscular body, he had short wavy brown hair, brown eyes, and a sharp chiseled face. " Yea " He said. " I came in the mud room and thought I heard something and I came back and there you were. " He said. Then he started again. " So, you like the role reversal. you like playing feminine role while having sex with a man? " Thats it. " I said. " But you said earlier that no one else knows about this, so where's the man? " He asked. " I've only been into this a little over a month, so I ve just been fantasizing. " I said. Then he suprised me and got me really excited. " Well drop the comforter, let me see you. " He said. " You're kindding! " I said. " No, drop it . " He said. so I dropped it. I automatically started my feminine mannerisms. " So who did you fantasize about? " He asked. " Mostly about men I saw in magazines..... and about a few that I knew, all were older though. Thats my thing , older men " I said. " How old? " He asked. " 40 to 60 " I said. " Hell I'm 45. " He said. " Yea.... I know. " I said slowly tring to make a point. " Hmmmm, was I maybe one of those few? " He asked. I nodded. " Yes." I said. " So you imagined kissing me, and licking me all over, and you imagined sucking my cock? " He asked. " Yes. " I said. " And you imangined me sliding my cock into your boy pussy? " He asked. " Yes..... and it seems you know the lingo? " I asked. " Yea I picked it up. " He said. He stood up, and said " Turn around and put your hands of the edge of the dresser and step back towards me until your arms are streched all the way out. " I did what he said, and it made it so my ass was pointed up at him, in the most feminine way. And let me tell you, I felt so exy. I was going to be his woman right now. I was so turned on, I thought my legs were going to start shaking. He walked up behind me and put his hands on my hips, and pressed his bulging crotch against my ass. He then walked us forward and pinned me to the dresser. His bulge was pressing hard against my ass now, and his face was right up against my right ear. I could hear his breath real heavy. His hands slowly slid from my waist around to my stomach where they rested just below my belly button. He whispered in my ear. " Your the hottest thing I've ever seen..... and now I've got you...... and you're gonna get so much more than what you imagined in your little fantasy. Are you ready for this.....your first time.....your first real man......your first real cock? " I could barely talk. I was so turned on, it felt like electricity was running through me. " Ya,ya, yes. " I stuttered out best I could. He kissed the middle of my ear, then began licking my ear lobe, which quickly moved to in my ear. Then he moved down to sucking my neck. Oh, this was so, so, great.... I almost couldn't beleive it. As he was sucking on my neck, his hands udid my shorts. He peeled them over my hips and they fell to my feet, and I stepped out of them. He pulled his right hand back andtook ahold of my thong pulling it up my ass crack. Then he moved it aside over my right ass cheek. He lifted his mouth off my neck and whispered " Hold on to your thong for daddy baby.
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