Teen Cross dressers First Man.
This is a true story that happened to me only a few monthe ago.
I just moved to a new town, I was an average 18yo male about 5'8 lean and athletic with a few female relationships before. I started to do a little bit of discreet cross dressing in my house about a year ago and thought about how great it would be to hook up with a shemale. I never thought it would happen of course, I didn't know where that stuff happened and I was always really shy.
One Friday after a grueling 4 hour study session at school one of my classmates, who I didn't know very well, invited me to have a few drinks at a local pub with a couple others from the group. We were all under 21 but the place was supposed to be laid back. I accepted because this was the last Friday before a crazy set of midterms and needed to meet some new people. Nothing too out of the ordinary, just a lot of drinking and clowning around trying to take the edge off. Around 1 in the morning his two buddies left and we figured we would stay for another drink and then share a cab home as we lived only a backyard apart.
While in the cab he mentioned that he wanted to toke and asked if I wanted to join him. I told him I didn't smoke but would chill anyway before going home. We got back to his place and he told me not to worry and that him mother was out of town for vacation with his little s****r for the next week. He totally baked out his entire room so much that I was feeling it. Somehow the topic turned to me rambling about how crazy my ex-girlfriend was and how I was not getting involved with another insane woman. Out of nowhere he says, men are better anyway and gave a really quick squeeze on my package. It was lighting fast and he just kinda laughed and took another toke.
I wasn't sure what to think but the first thing that came to mind was to just be cool, maybe it was like a pat on the ass type thing. He dressed kinda goth and I figured maybe that had something to do with it. I stayed a little longer before walking home.
He called me in the early evening the next day to see if I was down to study and have a few beers at his house. I didn't give what happened the night before any thought and made my way to his house.
Like the night before we drank a good amount and were feeling good, then he said casually that I had a big dick and could hurt a girl with it. I didn't know what to say so I just laughed and said thanks. He told me he shaves so his looks bigger and he stood up and pulled his sweat pants down just enough to not show his shaft. I say nice and he tells me he actually shaves his whole body and that he is "as smooth as young girl" and mooned me. I didnt tell him at the time that I was completely shaven too.
I could feel the mood turn right then in there as he smirked and wrinkled his brow. Immediately a rush of ideas and emotions pass through me. I was a little excited and definitely a bit curious. I never felt attracted to a guy before, I wasn't gay; although I did fantasize about shemales ever since I started cross dressing. He looked at me and said, "what do you think, have a little harmless fun?" Since all the cards were on the table I told him that I dress sometimes and thought about it. Then he says he dresses in his little s****rs clothes all the time and asked if we should both pick out something and see where it takes us.
Before I knew it I was told to pick out something and come to his room. I went straight to the hamper and found a dirty pair of cotton thong panties, a bra and stockings. I walk down to his room and my heart is racing. What am I about to do? Will I actually suck a cock or have one in my asshole? I open the door and he is fully dressed, wig and all and spread across the bed. I sat next to him and he rubbed my smooth legs, my cock swelling as he looked at me. Just relax, we are gonna do it all, he said as he lied me down on the bed peeling off my panties.
I couldn't believe it, I was getting sucked off by a guy and it was incredible. He gets in the 69 position and as I pull aside his panties it hits me. I am going to suck a cock. His cock was tiny, maybe 5 inches max but must have been as thick as a soda can and rock hard. Once my mouth was around it he would gently thrust in and out of my mouth and in no time tasted a sweet hint of precum. Just then he rolled over and pulled out a tiny bottle of lube as our cock stood straight up in the air. He just looked and said "who first" and I actually wanted to feel a hard cock pumping my asshole.
I didn't say anything, I just bent over doggy-style and waited to be filled. Seconds later his cock head was pushing to enter me. I moaned and gripped the bed sheets and he finally was inside me; it hurt so good. After maybe 3 or 4 minutes he told me to ride his cock. I straddled his lap and his cock eased into me again. Taking a cock is one thing but riding it was another. I got really into it clenching my asshole as I grinded his cock inside me. Within a minute he started to moan and said he was going to cum. Instead of stopping I bucked harder and faster until I felt warm streams shooting into my asshole. I milked every drop and when he pulled his cock out of me his cum rushed out of my hole.
Without delay he lifted his legs overhead and told me to cum in his ass. I didn't need him to tell me, I couldn't wait I thrust into his hole using his cum for lube. I was so excited I almost came instantly. I held back but not for long, seeing his cock flop around as I pumped into him was too much too handle. I blew my load without notice, collapsing on top of him as I continued to use his hole to milk my cock. There was no going back from this, it had happened and I loved every minute. We have been doing this regularly ever since and even had one of his friends join us, but that is a story for another day.
Posted by ClaireCD 3 years ago Views: