Gender bending

Master and i have talked about me dressing up as a boy a few of times, but have never really got around to doing it. We just discussed it a couple of days ago, and we might try it over the weekend. Will keep you posted on how it goes. :)
 
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My ex would enjoy it when I'd dress up like a boy, and I liked it too, especially in a military roleplay-context... Usually, it'd end with my crossdressing exposed, etc. He never crossdressed... And he probably wouldn't have made a very pretty girl xD
 
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A couple of weeks ago, I did some more cross dressing as part of a switch session...well, I was a cat burglar, dressed all in black and wearing a ski mask. I managed to overpower my master, and he said afterward that it was deply humiliating, and yet such an unbelievable turn on, to be overpowered and controlled by someone so little ;) And we're doing the same thing again this weekend too... :D
 
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Well I've never had an interest myself but I remember on the last day of high school I was on the bus there and saw, like, 20 boys all dressed in skirts and wigs! They were like that all day! lol

Any excuse, huh :p?
 
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Boy clothes are the only way that I feel comfy, jeans and a baby tee with no bra...no need...I'm just a sexy little twelve year old boy with very perky nipples.
 
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I crossdress a lot and my wife seems to enjoy it. We switch up, when I'm the subbie I dress accordingly and am more frilly - love it! When I'm topping, I dress in more of a b*tch mode, lots of powerful-looking attire, boots with heels, PVC, etc., and that's magnificent feeling. I make a great dominatrix - shame I'm not a real girl, but, as my wife and I already know, I'm a lesbian trapped in a man's body! :)
 
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^To the above poster, my boy often uses the phrase "lesbian trapped in a mans body" too so you're not the only one. :) Even my friends who don't know the particulars of our relationship think he's proof I'm a lesbian. Amuses me greatly.

To get back on topic, my boy crossdresses for me a lot. Most of the time I'm in mistress mode he's all dolled up for me. I like getting to choose his clothes and do his makeup for him.
 
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