whos crossdressed in front of someone they know before

[Jah Brother]

I did it in front of about 100 people of which I know most.
But it was for a playback show, so I did it just for the laughs, didn't get any sexual pleasure from it. Though I was one sexy bitch! (and quite drunk)
We didn't even win

[DoingMyBest]

I did it daily for the better part of two weeks.

A truly hideous blouse (a little too small), made of a dull lime green and a horrid brown swirling pattern, paired up with a orang, African-style-pattern skirt. I additionally had tracksuit bottoms, trainers and a hat of Pakistani origins.

Happily walked throughout Manchester like that, filmed like it and even had one of the other cast members decide to scream and shout down the street "Look, it's a man weaing a dress!" repeatedly as he flicked up the skirt, whilst I walked under a see-trhough Hello Kitty brolly with the tiny actress - they all stared at him, not me.

[mrpropel]

Couple years back in front of one of my male friends, it was awesome and a very exciting day. I won't go into details..

[MisterDare]

I did it in front of my friend from school. Mainly because he had a sister and I didn't, he wouldn't do it because he said he was to nervous even though I think he was hard.

[-misti]

Originally Posted by daremaster1

whos crossdressed in front of someone they no before and explain in detail why it happened

Yeah, many times. Sometimes just dressing up around the house or when chilling with friends. Others when out at fetish clubs or similar

[naked_lego]

This was from 10/18/2012... I can't believe replied to this in WAAAY back then.
Of course I don't really consider myself a crossdresser now. Which says something how I grew over the last 6 years.

Originally Posted by naked_lego

I have crossdressed infront of my sister before. We were playing a dare game I made up. We lost and had to do the same dare. For me it was more thrilling because we had to wear dresses and play guitar hero. :P

Then 1 other time we were playing the same game and we lost again so we had to switch outifts. I was wearing her cloths (comfy pants, undies, bra, and t-shirt) and she had to wear mine (T-shirt, shorts, boxers).

Now since this is a crossdressing reply thread the only other interesting time I "crossdressed" (now with quotations) is with a friend of mine and her mom. It was Halloween. I went as a "girl" (this was when I started coming to the thought I was trans). To explore the feeling I had my friend and her mom dress me up. Well, I got to their house and their mom put out some outfits in the bathroom for me to try. I chose a black long skirt and red/black blouse. I wore my panties there. It was an odd feeling being mostly naked in someone else's bathroom and them knowing it.

I walk out of the bathroom and they all say I look good. Her mom does my makeup, just eyeshadow, lipstick, and blush. To be honest I looked super ridiculous.
We didn't go out just at night and I was paraded around late afternoon for an hour before I had the cover of darkness to hide my ridiculousness :P

[Truckernaut42]

An old friend of mine I really wanted her to get naked and see me so I talked about us wearing each other's clothes but even though I get totally naked and then put her clothes on after, she only let me see her dressed, though I could see her nipples through my shirt because I was wearing her bra.