First time sex

Seems most have good memories of thier first time having sex! Mine is slightly different but I have very fond memories of it! I was 16, I'm a little on the small side in all aspects,my best friend since elementary school was and still is a girl named Amy. So I was a young man in high school not many friends, short skinny long hair not very popular. Out of the blue Amy says let's have some fun this weekend and go to a party.......being not popular I protested a bit, she says hear me out.. So you are cute but I believe you would look killer as a girl! We just need to make you over and see if im right. After so thought I figured what have I got to lose... After a long hot shower shaving all the hair off my body, didn't really have much truthfully, she started out by giving me some cute little panties to put on, after I put them on she looked me over saying that won't do.... a quick Google search and she found how to tuck my little penis, a little tape later I looked more flat like a girl in front. Next came the pantyhose tan shade,then a little denim mini skirt, sexy purple bra stuffed with two balloons with water, not filled enough to pop but enough it looked like I had a nice little set of boobs, then a cute blue top...and one to some black 3 inch heels to complete my look...she styled. My hair and did my make-up before letting me look in the mirror......wow she says I was freaking totally right you are damm hot! If you don't make a friend tonight!! The time came to leave for the party after some time of me learning to walk sexy in heels. We arrived and went in, it was crowded!
Amy led my around a bit and introduced me to some boys, I was so afraid and concerned that I'd never been with anyone much less a boy! After a drink I was much more relaxed. This tall hansom guy kept looking at me and finally walk over and said hi.... did my best to not look nervous and said hi how are you? My name is Cassidy... he asked if I'd like to maybe step outside it would be a little quiet and we could talk. We made it outside and talked for like an hour, when he leaned in and kissed me long and hard on the lips.... I melted a bit and found myself kissing him back and really liking it!! He then pulled back and said Amy told me a bit about you....and I like what I heard... can we kiss some more? Hell yes I said I couldn't believe this I'm kissing a boy and really liking it! We made our way to his car and made out more, he became a little more brave and I could tell he was excited by the bulge in his jeans.... I reached down and unzipped his pants and his cock popped out hard as a rock! I couldn't help touching it and then rubbing it, he seemed to like it so I stopped kissing he lowered myself down and took it in my mouth.....
I couldn't believe what I was doing but it turned me on having his cock in my mouth.. I sucked it the best I could not knowing really what I was doing. Before long he grunted a bit and said he was about to cum, I just kept doing my thing when he explodes in my mouth wave after wave of cum! It tasted so good! After we went back to the party, I met up with Amy and she asked how it went I told her the whole story, she turned to me and said you lucky bitch! And on your first time out even!

By Anonymous

Sex CONFESSION

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