A kid I used to be friends with (who we'll call M) needed a date to the prom. He reminded me of all the times I borrowed money from him and never repaid him and stated that for payback I should pretend to be his date.I had laughed at M thinking it was just a joke but when he told me he was serious I tried to convince him that I was going to pay him back and there was no need for either of us to do that but he was not convinced.
Realizing I was on the losing end of this argument and that this was our final year in High School and if I got a pretty convincing makeover only a select few would even know it was me. I decided "**** it I'm never gonna see most of those people again" and I agreed to it.
I went to a dress fitting, got a hair appointment you know the whole nine yards.The dress store had been an kind of exciting experience with M making me try on at least 10 dresses in a store full of girls my age. When I came out of the dressing room to show M each dress all the girls and Moms in the shop stopped and stared as if they were all invested in what the lone boy trying on dresses was ultimately going to choose. A particularly funny moment was when I emerged from the dressing room in a particularly tight and short, form fitting red dress, a mom who was in the dressing room next to me came up to me and told me I "looked sexy" was "very brave" and was "just as much a girl as the rest of them" and then told me that I hadn't zipped up the back and did it for me. Not knowing what to say I gave her a quiet thank you.
When it finally arrived (Gulp) I lied to my parents and told them I was going to hang out with M tonight (well I was but not in the way they thought). When I got in his car stopped at the place were I got my dress and picked it up I had to change in his car, we then stopped at the salon and I got a complete makeover plus my hair and nails done, when we finally arrived at M's house I saw his whole family outside ready to take pictures. he assured me that only he and I were the only ones that know I'm a guy, he never told his family about our little deal everybody will think I'm a girl. Knowing I can't be having second thoughts now, especially all dolled up like I was in his car M 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 M said we had the same environmental science class.
His sister was chatting my ear off saying how we have got to hang out after all this. We finally arrived at the prom at 8:41 p.m. and as we walked through the hall I noticed that with the heels I was only an inch or two shorter than M, I was also nervous that people would figure out it was me. Some did and yeah they laughed at me and called me names, I took it in stride and ignored them. Others were actually amazed at how I looked and complimented me. I danced with M and actually had a great time, I also ate some damn good cheesecake. We didn't win prom king and queen sadly. We took some photos and at around 1:08 a.m. we decided to leave. We stopped at a Buffalo Wild Wings and I changed back into my regular clothes as he drove me home. The next day M asked me how did it feel and to be honest it was actually pretty fun. So I'm curious, have any of you ever cross dressed and went to a prom or dance or party? If so, how did it feel? Did anyone know it was you? Did you have a date? Would you do it again? If you haven't would you ever want to?
