I Am a Teenage Crossdresser

Powderpuff Game

By: AliceSnow

Written on February 2nd, 2013

So, in our school we have a club for all the club presidents called interclub Council ( It's kind of like the UN), I'm the "step-in" president for Art Club, and every year there's a powderpuff game for the Juniors and Seniors. We discussed how we were gona do that, and they want me as one of the Cheerleaders at the game. I honestly don't know i I should go all out to look like a girl or just go with the rest of the guys and just be very sloppy about it. But, wither way, I'll probably get to wear cheerleading uniform! If anything I'll have to hide my "pride" from everyone attending the game! I'm very excited about it, but I truely do not know how to approach this. As a crossdresser, I want to look the prettiest and actually look like girl, but I'd hate to be the only guy out there dressed as a chick and pulling it off. Not many people still know about my dressing and I know if I went all out it could go one way or another. I don't know, any suggestions?

By: AliceSnow

Age: 16-17

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10 responses

Needitbad100

I'd say decide whether or not you want people wondering if you are or not. Going all out could start to make people wonder or even know then. I'd love to see you in your cheerleader uniform.

Feb 14
1 like
griffti6

do it! if people ask, tell them you go big or go home! it is a game isnt it? ;)

Feb 9
1 like
glasscitycd90

go with what feels right to you if it were me id have fun with it an go all out if anyone asked id say my mom did my makeup but thats just me

Feb 4
1 like
Blueboy212

If I were you I would go almost in drag. Go a little to much eyeliner or some bright red lipstick- basically make it look like youre almost making fun of the cheerleaders. You could possibly even wear some clear nail polish if not colored.
Just a suggestion

Feb 4
1 like
Kim1girl

Alice, I am in the camp of going for it. Your doing it well doesn't mean that everyone will conclude you dress.
Most (all?) of us will tell you how we regret not pursuing the opportunity when presented. I wish you the best!

Feb 3
1 like
SissyHWAdmirer

I think that you should go all in. A guy that I went through school with dressed on every occasion that he could get away with it and on some that he could not - he was sent home one Halloween. He always looked great and truthfully we really never thought much of it other than how surprisingly attractive he looked. In hindsight I realized that we were pretty naive thinking that he was just being a goof.

Feb 2
1 like
highsockssissy

Have some fun and look better than the usual cheerleaders :)

Feb 2
1 like
andreaneejustinfield

Go all out and enjoy the moment. This will be a memory of a lifetime. Talk to the girls and see what they think of you being all dolled up. They may want to dress you more often.

Feb 2
2 likes
nicolecrossdresser

do it girl.

Feb 2
1 like
STLCD

Just do it! This is a chance that many of us never get so if I had this chance I'd be all over it and not care what anyone else will think. And you may just impress a lot more people than you think.

Feb 2
2 likes

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