Gay Roommate crossdress

I have been cross-dressing since I was 7, always been a bit in the closet about my homosexuality and cross-dressing but I have always loved it and kept it close.

I had one roommate when I was living in Boston his name was James. he was a pretty good looking guy who seemed to always be doing well with the ladies and I always secretly watched him as he paraded around the apartment in his underwear always hoping one day he'd notice m little did I know he already had.

it was a typical Saturday morning I had gotten up and said hi to James on my way out for a jog, went out the door and started walking towards the park when I realized I had forgotten to recharge my iPod the night before I had been gone for about 15 minutes and decided to go back to the apartment for my spare.

It was when I walked into the apartment and back into my room that I made a shocking discovery, shocking but beautiful. There was james my hot roommate in my room wearing my black lacy french cut panties, matching lacy bra and 4" heels, his cock bulging in his panties, god was he hot, completely smooth shave except for a five o'clock shadow it took my breath away. he was startled for a second as was I, playing on my computer was a video from my own personal gay porn stash. we looked at each-other for what seemed an hour and then James smiled. without saying a word he reached into my panty drawer and handed me a white thong, bra and knee high stockings. there he was smiling at me handing me my own panties. I took them from his hand, he stepped close to me, kissed me gently on the lips and whispered in my ear. dress up for me, be a sexy gay boi with me.

I could not believe it I got so excited and I sat on the bed and undressed while he stood in front of me smiling, I kept running my eyes up and down his sexy, lingeried body. I quickly slipped on my panties, bra, knee highs and reached for pair of heels, he extended his hand to me and I stood up, our pantied cocks barely touch and immediately got hard. we kissed, we kissed hard. we each reached for our asses and pushed each-other close, our cocks hard against each-other we were going wild.

I stopped for a second, looked him in the eye and said "I've wanted this for so long" as I dropped to my knees to rub my lips against the hot bulge in his panties. I rubbed his cock through the panties, kissed it and finally pulled his panties aside and swallowed his glorious cock whole......he moaned.

i could not get enough, his hot, throbbing cock felt so good coming in and out of my mouth, his hand on my head, I pulled out my own cock from my panties and started stroking it hard I was in heaven.

Periodically he would stop and kiss me and again shove his cock in my mouth, I would rub his pre-cum on my lips and love every second of it.

finally he pulled me up and kissed me, threw me on the bed and got on top of me, our cocks rubbing against one another, so hard, so hot.

Slowly he kissed my lips, my neck, sucked on my nipples through the fabric of my bra, my belly until he began to suck my cock like only a gay man can suck cock, he put a finger up my ass and I almost lost it.

Finally he had me laying there in bed, my butch roommate in his sexy bra and panties, pulled my panties aside, kissed me and said "I am going to make you my bitch now" and I felt his hard cock against my ass, slowly pushing in, i gasped for air, I moaned, "James whimpered "sshhh" he responded, I held him tight as he put his cock in my ass and started to fuck me hard like the slut I am.

He kept fucking me harder and deeper and harder again I was in heaven with my roommates cock all the way inside of me. i was screaming until I just could not take it and started to cum wildly over both of us. he smiled and kept on fucking my ass.

we looked at each other and I said “james please cum in my mouth, all over my face” he just smiled and kept fucking me until finally he pulled out, sat on my chest and his throbbing cock started to shoot his hot, sticky cum all over my lips, my face, on my tongue and down my throat I was in heaven.

as I laid there sucking every last drop of his hot cum, he laid next to me, held me closed and kissed me and said “well we are going to have to do this often, nothing prettier than two gay boys in lingerie fucking” and we shared a passionate cum kiss and feel asl**p.
98% (152/4)
 
Categories: Gay MaleShemales
Posted by alex_boycd
4 years ago    Views: 2,747
Comments (29)
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4 months ago
my college roomie would always go through the panties I had collected from girls with whom I had sex in school and would try them on always believing that I never knew he liked to dress in panties. I have not seen him in years but Greg has decided he likes boys better than girls. I hope I had some small part in his self-realization.
9 months ago
perfect fantasy of mine
10 months ago
this is really hot
10 months ago
very hot
1 year ago
fun
THECROSSO...
retired
1 year ago
ENJOYABLE SHORT STORY THANKS FOR POSTING
1 year ago
wish I had a roomate like that
1 year ago
OH! YOU Are SOooo lucky..! I was so turned on bi this...
2 years ago
so hot so sexy so great
thanks
Jay
2 years ago
hot very hot
2 years ago
that was hot,had the same thing happen to me,only, I was caught by my roomate who walked in on me fully dressed,it was like hot guy fucking his slutty tgirl roomate
2 years ago
nice one. I would like to have that experiance...
candi0058
retired
3 years ago
wow what a surprise thanks for the story
Candi
3 years ago
this is so hot
jacquin001
retired
3 years ago
Wow that was a fantastic story had me jacking off thanks
3 years ago
god i luv your stories
3 years ago
wow gr8 story happened to me just like in the story
quin058
retired
3 years ago
Thanks dor a great story hope you write more thanks
3 years ago
wow!! loved your story :))
csng69
retired
4 years ago
hottt
4 years ago
I must have done something wrong, or went about things the wrong way, cause I never had a roommate like that... dammit

BTW, very hot story, and a big turn-on!
4 years ago
Again, you are so lucky. Great
Story.
4 years ago
mmmmmmmmmmmmm
mike4u212
retired
4 years ago
great story love it
augustboy17
retired
4 years ago
excellent perfect
4 years ago
loved it
4 years ago
loved it more please: sexy knickers , and hard cock , perfect together
jackguns
retired
4 years ago
Wow that was hot and horny had to jack off so i could see staright thanks
Wire99
retired
4 years ago
Very hot!! I've always dreamt about doing somthing like that (wearing panties, and the sex lol) Hope you write more!