- Transgender & Crossdressers
- How I Met My Boyfriend
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This is the true story of how I met John who has been my boyfriend for the past two years. I had returned to my hometown to attend our ten year class reunion- which went about as well as you would expect- meeting half-remembered people who weren't important to me then and who aren't important to me now. With some exceptions- my two old friends Bill and Bruce were there and we had a great time swapping stories and Bill invited us over to his house to play some poker the following night ( which was a Saturday).I promised to attend so about 9 pm I arrived to find the guys already well into the sauce and Bill introduced me to his friend John who seemed friendly but kind of reserved.
Bill informed us we would be playing strip poker which I thought was kind of dumb seeing as there weren't any women there but kept my mouth shut.
We played for awhile and all of us had to remove some clothing but I was down to my socks and boxers when Bill said Ok- time for a change- and brought out four plastic bags full of clothing. He said we would all dress up as women now and start all over again. I thought that was a pretty good deal as I was losing and this would give me another chance.
We all went off into the different bedrooms and I spent a good ten minutes getting dressed - putting on all the sexy lingerie- the blouse and skirt, shoes and wig- those idiots were going to have to win a lot of poker hands before I had all this stuff off.
When I came back out the guys were all just sitting around drinking- none of them had dressed up at all. I said What the hell is this? They just laughed and said it was a joke and to relax and have a beer. Well I was a little ticked off but I had a few beers and when Bill put "let the good times roll" on the stereo I pretended to be a stripper and did a little dancing.
We were all pretty wiped so Bruce and I crashed on the two chesterfields and Bill and John grabbed a piece of carpet on the floor and the lights went out.
Bill woke me up sometime later-he was poking me in the ribs- I said what do you want and he said look- I got a big woody when you were dancing and could you help me out with it? He grabbed my hand and put it on his dick and sure enough he was as hard as a rock. I moved my hand on it a bit and he whispered yeah-yeah thats great- and moved up so that he was sitting on a chair at the end of the chesterfield and was pulling me towards him.
His dick almost hit me in the face- I didn't want to blow him but it was dark so I figured what the hell and wrapped my lips around his cock.
Immediately the lights came on and as I turned my head Bruce and John were staring at us- their cocks pointing right at the ceiling. It must have been quite a sight with me dressed as a chick laying over the end of the chesterfield with Bill's cock in my mouth. Bruce got up behind me and was rubbing his cock in my ass crack. Yeah- I gotta get me some of this he said and I heard him unwrapping something and then I felt his slippery cock pressing against my hole. I was trying to get up but Bill kept pushing my head down on his cock and as Bruce pressed harder and harder I felt my ass muscles give way and his cock slid all the way up my ass till I could feel his hairy balls on my cheeks. Yeah- oh yeah- that feels great- your ass feels so good Bruce said as he stroked my ass. I was twisting and squirming but Bruce just fucked me harder and faster until I could feel him shooting in me. He then pulled out and John grabbed me around the waist and turned me over onto my back. I want to look in your eyes while I fuck you he said and I felt his thick cock slide up my well lubed ass- I instinctively squeezed my ass muscles and he said yeah- that's it baby- milk that cock-every time he pulled back I squeezed so I would be tighter as he stroked back in and after just a few minutes I could feel his cock jerking as he shot another huge load up my ass. He leaned down and kissed me and said You're my girl now Tracey. We left hand in hand.
It's a great relationship- He loves my ass and I love his cock.
- COMMENTS
Anonymousalmost 13 years agoHi Tracey,
I am a bisexual crossdresser in Augusta Georgia and enjoyed your story very much, I would love to be a loser in a strip poker game and satisfy the guys sexually, I love your profile picture, you are very attractive.
luv,
Josie
Anonymousover 14 years agoYour photo is hot,i shot cumm all over it.Would like to get behind you and fill that hot arse with cumm..Rob
Anonymousalmost 15 years agoTold it was be females to dress as males, males as females, party.I dressed in a loose red dress, no panties,sheer, shiny pantyhose,high heels, wig, even put makeup on.I must admit, my cock wouldnt stay down, the feel of the hose making me feel very sexy.I pulled out my cock and after a short time i shot my load into the shower.Better, i felt relaxed.At the party, some had come dressed up,others not,i dont think anyone recognised me.Plenty of drinks, dancing and i was sitting down,feeling good when a young guy came and sat next to me, hi im Sam,you are, umm, umm Sarah.We talked and after a while he placed his hand on my leg,stopped then slowly traced his fingers under my dress.He stopped,want to go for a walk outside, he grabbed my hand and pulled me up.We went down into the back yard, behind the garage wall he put his hand under my dress and groped my bottom.I should have stopped him,but i didnt and then he unzipped his pants and his cock popped out.He guided my head to it, and for the first time i took a cock in my mouth.He slowly pushed into my mouth as i sucked his cock, going hard.He stopped, pulled me up, turned me around. lifted my dress, rubbed his hand on my balls and just froze, i jumped forward, he pulled back, no i heard him say.He zipped up and strode back into the party, what was i thinking, it felt good, my cock was hard.Then i heard voices, he had come back with a friend, he grabbed my hand and we went out to the street.His friend opened the sliding door of a van, we hopped in and drove until we came to a block of flats.He ushered me inside and pushed me to the lounge,pull that dress up, i did, he then came and groped my bottom, gently stroked my balls.and then told me to bend over the lounge.He lifted my dress, pulled my hose partly down, and inserted a greased finger into my hole.I went to stand but his friend held me down.You want to be a girl, now i am going to fuck you like a girl and with that i felt his cock pushing at my hole.First time i tried to clench up, relax slut he said or it will be very painful, i managed to relax a little bit and the head of his cock entered me.Aaaargh as i tried to pull away but his friend held me as he kept pushing forward until his cock was all the way in.Fuck shes tight, geez,as he slowly pulled back, then rocked forward into me,repeating until the stinging got better and as he went faster my cock reacted and it didnt feel bad.Look at her she likes it now as he sawed in and out of my arse, my hole clenching and unclenching until i felt him get harder and he said im cumming and he released his cumm up into me, still fucking, my cock hard, as he kept filling me.Then he slowed and pulled out, i felt cumm running down onto my pantyhoser.I went to stand but i was held down and told now it was Rons turn, ron pushed his cock at my mouth, it was big, very big as he fucked into my mouth, then moved behind me.No i cant take that.Thats why your here, the local girls wont let him fuck them because he is too big, i have just lubricated your insides and i told Ron if we could use his place he could fuck you.I felt the head of Rons cock at my hole,then with one push, it opened my hole and went in.Just the head,sitting in my hole as Ron started to do little backward and forward rocking working his cock in for what seemed an eternity until i knew it was all the way in.Shit Ron, she took it, my hole filled, then Ron pulled back, aaaaargh, then forward, he was hitting something deep inside me as he moved faster, stretching me opening me up, my cock cumming as he moved forward, couldnt help it, big long loopy sprts as he went faster, my cock staying hard as he just continually opened me up.I felt myself pushing back, yes, yes, give it to me.You heard her Ron give it to her as he really put that cock into me, my cock still hard, trying still to cumm but no mre cumming out.Harder now, bigger, i heard him yell as with one big thrust he emptied out into my stretched hole.I blacked out.I came to as Ron was pulling his cock out of me, no leave it there, but he was finished.I heard the other guy say, geez, i thought no one could take that.The other guy pushed his cock back into me but i hardly felt it as he rooted into my hole pulling out and splattering cumm onto my back. I finally got dressed and went back home, not walking all that well.Word got around about me, and i am quite popular.Ron calls me nearly every day, he is only 19, i dress for him and he takes me when he wants, however he wants, as long as his big cock is chugging up into my backside filling me with cumm.He said no girl yet will take it, but he is happy, so am i,i cumm every time he enters me, stretching, touching me deep inside.I have even lowered my self straight down on his cock, all the way and as i get to the end of it my cock standing straight up in the air shoots my load .I have not seen the other guy.
