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How I Started


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A kid I used to be friends with who for anonymous reasons we'll call X needed a date to some lame dance his school was hosting, now this was maybe my first year. It's been so long though so my memory is a little fuzzy anyway he jokingly stated that since I owed him money, I should pretend to be his date and then he'll consider us even. We both had a good laugh about it and each went our separate way but then a week later I was reminded that with the the way my funds were set up at that time, I wouldn’t of been able to pay him off properly (I had just recently funneled all of my money to get a very cheap car) Realizing I was a poor bastard and had asked multiple times for extensions for the date that I owed him I called him up and asked about that whole date thing and he told me he was only joking when he said that and that he didn't really want me to do that but I was able to convince him ( it was mostly just me telling him that we did not go to the same school and if I got a pretty convincing makeover nobody would even know I was a boy) he agreed to it.
I told one of my girl friends about this whole deal I worked out and she gave me an old dress she wore to one of her dances, and a wig she originally bought for one of her friends. For makeup she called her friends and they came over to see what they could do and if they could 'fix' me (mostly make it look like I have breasts).
 While this was happening I lied to my parents and told them I was staying the night at my friend X's house and was going to hang out with him tomorrow night (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 again). I had to change When I got in his car, we stopped at his house to take pics and then went on our way. We finally arrived at his school at around 7:00 p.m.
"Alright! You ready?" He said,
"One sec." I nervously replied back, he assured me that only he and I were the only ones that know I'm a guy, everybody else 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 X went to open the door as I zipped myself up, grabbed my shoes, and with a deep breath, stepped out.
We walked through the hall and I noticed that with the heels I was only an inch or two shorter than him, I was also nervous that people would figure out it I was a boy. X confessed that he had told some of his friends about our little deal but they swore not to tell anyone(they didn't but oh boy did they give me hell) I danced and actually had a great time. We took some photos and I ate some damn good cheesecake, I also realized X was a really great dancer.
At around 11:08 p.m. we decided it was time to leave I changed back into my regular clothes in the school bathroom and he drove me home. I guess you could say that awakened something in me because I began having fantasies of doing it again I tried ignoring them but they kept getting stronger. Eventually, I just had to give in and do it one more time (I guess to get it out of my system) so I did and when I put those panties on for the second time the rest was history.
So I'm curious, have any of you ever cross dressed and went to a dance, or party? Was it intentional? 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?

here are some pics:


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Great story.  My first experiences were at a younger age during halloween and i certainly didn't rock the look as you did in those photos!





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Just now, Charlize said:

Great story.  My first experiences were at a younger age during halloween and i certainly didn't rock the look as you did in those photos!





Thanks Charlize!

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This is a wonderful story. You look amazing. I dont't think i would have had the courage to do you did when i was young (that would have beem the 1980s). Thank you for sharing.

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You totally rock, girl! Back in the 60's that was impossible. The closest I came was a ballerina for freshman initiation and a cheerleader for a skit for a pep rally. Would have loved to do that, tho.

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