I've been a crossdresser since I was in middle school, and as soon as I got out on my own I started working on becoming transgendered. Only recently have I been confident enough to go out in public, and I've been going on walks getting used to wearing and walking in heels in a public setting. I cannot walk very far yet, and as I stopped rest my feet, I was leaning against a lamp post and rubbing my toes, when a car drove up. The person inside asked me if I was interested in a party. I blushed and looked at him, then he said: "200 for the evening."

I made 200 bucks for doing something I would have gladly done for free.

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Anonymous

by Anonymous on Dec 15, 2013 at 1:29 PM

When I was 16 I'd dress like a girl, my sisters clothes fit me just right, I wore a few of her dresses, but perfered her jeans best. I'd get dressed and head over to the the country and western dance place on Saturdays nights. There were always lots of older drunk guys around, some would offer me 50 dollars to let them play with me. They would pay upfront after getting in their car, I'd get their dick out and play with it, most would pass out before anything happened.

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Anonymous

by Anonymous on Aug 7, 2015 at 9:00 AM

I'm an almost everyday crossdresser. I'm 26, 5'6", slim and athletic. I look drop dead passable in public, total fish. I pretty much date tranny-chasers. One tranny I'm friends with once told me I could make bo-koo $$$ as an escort. I was intro'd to a professional escort who said that girls like me are in demand, the client were totally upscale, and was I interested.

I do this about once a month. The guys are somewhat "bottom", letting me be assertive. It's very cool. TOTAL safe sex, and I make $1500 - $2000 a date.

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