Best friend

Ive been crossdressing since like 6, when i was 16 i was staying overnight at my best friends house, he was 17 at the time it started off us playing video games eating pizza just hanging out...i went upstairs to use the bathroom,i noticed his sister's door was open since no one was there but us i went in,she had lots of clothes laying around,i couldn't help myself figuring i had a bit upstairs by myself i decided to try something on,this was the 90s so jean mini skirts were in so i stripped and found one to put on looking in the mirror something was missing....pantyhose so i found a pair to put on,checking myself in the mirror i couldn't help but see the little bulge in front so i pulled down the pantyhose and tuck myself back real good and pulled up the pantyhose, then i found a awesome Rolling Stones tee shirt and cute pink bra putting them on i was in heaven! At this time in my life i was pretty small thin and her things fit me so well.. i had gotten completely caught up in dressing i hadn't heard my friend standing in the hall.. When i turned around he said wow you actually look pretty hot in that stuff! I froze not really knowing what to do..... he came into the room and said its ok i kinda thought you may be into crossdressing you always look more at the clothes than the girls... then he ask how i felt in the clothes i said amazing! He said well you look amazing! He put his hand on my ass saying it was the best ass he had seen, then he asked me if he could see my ass without the skirt? I unbuttoned and unzipped it letting it fall to the floor,he said wow hot so where is your dick...i kinda laughed and said tucked away. I could tell he was turned on by the huge bulge in his pants.... he chuckled and said with a smile we should fool around a little.. i couldn't help myself i reached down and unzipped his pants reached in and felt his cock, it was so hard! I get down on my knees and licked the head not really knowing what I was doing i started sucking it like id seen i the movies he really seemed to enjoy it! He asked if he could maybe stick it in my little ass...i could hardly stop myself from turning around and bending over his sister's bed, he started slowly spitting on his dick for lube i could feel it entering me slowly...it hurt a bit but as i relaxed it started to feel amazing! I think be my breathing and was extremely happy so he continued fucking my little ass....then he said im about to cum! I told him to go ahead i had already cum a little bit ago... wow what an amazing feeling.. He pull out and i pulled up the pantyhose and put the skirt back on we ended up doing it a couple more times that night i stayed dressed up all night best night ever!

By Anonymous

Sex CONFESSION

Report