This was back in either '03 or '04 forgive me for it's been some time, but anyway at this point in my life I had been dressing for some years, but that was of course only in the confines of my home, I never really done anything in public. But the opportunity to do so would come very soon and in a very big way, a close friend of mine had asked me to go to our school's senior prom (I was in a grade below him) at first I thought he just wanted a friend to accompany him, but I soon realized later when he called me at home that he wanted me to be his
DATE date, I was flattered and told him thanks but no thanks. I explained that this was going to be really difficult, not only because I never truly did anything that risky before, but I also had to do a whole damn lot to even be able to pull this off as well. I was very high strung at that point but he calmed me down and said that since I was a year below him nobody I knew would be there and that because I already had pretty fair features I could get a pretty good makeover and pass with flying colors, I was still didn't agree, then he offered me some money, and I decided 'F*ck it' and agreed.
I decided a sleeveless blue gown around my neck was the best bet, finding shoes to match that was actually the hardest part honestly. My hair was pretty big already, so all I had to do was press it and have it curled, my nails were done in the same blue as my dress, and my 'breasts' belonged to my sister and were held in place with adhesive (looking back now that was a really, really painful, dumb and not to mention bad idea) I put on my mother's girdle to 'hide' myself, I lied to my parents and told them I was staying the night at my friend's house and was going to hang out with him tonight (well I was but not in the way they thought, hey if they really knew what I was going to do I would've never been able to come home or show my face again) and I left, god my stomach was practically doing flips. I had to change When I got in his car.
When we arrived at his house I saw his whole family outside ready to take pictures, he went to open the door as I zipped myself up, grabbed my shoes, and with a deep breath, stepped out and posed with him for everyone. His mom asked how we met and he said we had the same science class.
we finally arrived at the prom at 8:41 p.m. and as we walked through the hall I noticed that with the heels on I was shorter than him, I was also nervous that people would figure out I was a boy and when I also saw some of my other friends there I tried my best to avoid them, didn't want to deal with them seeing me like this so I tried to be discreet, although my 'date' parading me around the hall and showing me to everybody like some sort of damn trophy and giving my ass the occasional smack and squeeze certainly didn't do me any favors except cause a red mark on my ass my panties to bunch. We danced and some people were able to figure it out and oh god did they give me hell, but I really didn't care because I had a great time, we didn't win prom king and queen sadly but we got to take some beautiful photos and I ate some damn good cheesecake (It was practically orgasmic lol). At around 1:08 a.m. we decided to leave, we stopped at some restaurant and drove to a hotel for the night. Although we slept in the same bed nothing happened I promise, but I did forget to bring regular underwear so I had to wear the lingerie I bought for my gown so it was really awkward, well I guess for me it was awkward because whenever I got up to use the bathroom he would smack my ass and smack it hard, and would caress my butt while we slept. When we woke up I had a huge red mark on my butt, I changed back into my regular clothes and he drove me home. When I got home I didn't even have time to change my underwear because my parents decided now would be a good time to visit my grandmother so I spent the entire day wearing lingerie at my grandmother's house. I'm now married with a family and am still friends with him, he always refers to me as 'my friend that was stupid enough to actually be my prom date' and will always tell people the story, he seems to enjoy that time we had a whole lot more than I did, but hey on the bright side I earned some easy money and I had a date to the prom (which is funny because I went single to
MY prom).
