My First Time With Anal Sex

This cross dresser provided me with some silver panties and a bra with b-cup foam breast forms. Also included was a plaid skirt with a white button shirt that stopped at the top of the silver bra. Her (that's what the cross dresser wanted me to call her) boy friend was standing their in his boxer, she was just in a top and panties. I immediately went over to her boyfriend and pulled down his boxers and kissed the shaft of his ****.

I took it in and began to grind my teeth against the shaft, not really knowing what to do. He was really kind about it, the cross dresser pulled her panties off and tried to penetrate me; since I was a virgin it didn't go so well. She told me to lay down so she could **** me but I wanted to keep sucking his **** a little more, and they let me. He started to hump my face but I gagged and that was really the end to my first blow job....

...But it wasn't the end of the night as they set up a pillow and lubbed up the cross dressers ****. I felt sharp pain and then an immense pleasure as I moaned and humped her ****. Her boyfriend stroked his **** and my fake **** before his girlfriend backed away; letting him (and his 8' ****) have free reign. And that hurt initially; but good god was it orgasmic after that. Apparently I was able to out last him as he pulled out, removed his condom, sucked/jacked me off till I finally orgasmed and cummed.

It was amazing.
jessicafemme169 jessicafemme169
18-21, M
9 Responses Jan 7, 2013

Wow...what a GREAT intro to crossdressing and gay sex. So hot that there were 3 people there, and 3 ***** (no *****!) Lol.

Wow that's some story

very nice and exciting story

mmmm sounds like you had such a fun time, wish i could have been there

really hot story

love your story wish j had some friends like that how did you like the way you looked

You know how to party young girl!

What a hot story. I would like to do the same

It was XD
I learned though that it takes time to get the stamina for the really fun stuff like spit roasting. I wish I had gone back again

sounds like a wonderful time

It was an absoulutely amazing time :)