whos crossdressed in front of someone they know before

daremaster1 · 12-03-2007, 02:11 PM

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

slave_boy · 12-04-2007, 04:52 AM

done it front of mg gf once and she was laughing that much she put makeup on me filled the bra and took pics

manjuice · 12-04-2007, 06:59 AM

ive done it in front of my gf too and also wore a thong and mini skirt in front of her and 3 of her friends for a dare. I was very drunk

robcam753uk · 12-05-2007, 09:37 AM

Done it for an ex gf, she thought it would be funny to get me dresse dup in her clothes ( i was little bit drunk at the time, lol) she had me wearing a thong and tights too, lol

StylishKidInTheRiot · 12-05-2007, 10:26 AM

as a dare, wore my girlfriends panties and bra at a mates party for the whole night. i was drunk at the time though.

shola · 10-18-2012, 06:15 AM

I was in my (female) cousin's (stuffed)bra, shirt, and shorts once, in front of her and my (male) cousin - though I made it to be more of a joke.

naked_lego · 10-18-2012, 11:45 AM

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).

messyalan · 10-18-2012, 11:59 AM

I have dressed for a pub fancy dress and got a good snog with a woman. As I like going out dressed but hidden my most memorable experience was when I met two women and a man without any chance of hiding. They seemed fine about it.

anonimousbob · 10-18-2012, 12:41 PM

A friend came to stay one weekend. We went out and got drunk and when we got home she put a load of her makeup on me while we waited for some oven chips and chicken nuggets to cook.

I think if the timer hadn't gone off she would have brought out some clothes for me. She took pictures as she was doing the makeup and has since told me she deleted them. I'm not sure if I believe that or not

spoon55 · 10-18-2012, 01:39 PM

i did it infront of my gf and whole of my college as part of a charity thing. our sports group dressed in full womens outfit while we played the hair and beauty group at football then had our legs waxed after on local radio

Dareholic · 10-18-2012, 01:52 PM

The only time I have ever done it; was for a play back in high school. It was a comedy. We where only trying to get a few laughs out of it.

lacelover · 09-30-2014, 11:17 PM

Yes i have worn female clothing and yes i slip into womens clothing in front of my step sister we share our lingerie and clothes

omega10 · 10-01-2014, 07:30 AM

I got tipsy with my (at the time fiance, now wife) and her two sisters were staying with us at our apartment. I decided to agree to let them do my makeup and I wore the perkiest bra they had with a low cut shirt and short shorts. I also put a thong on with them all in the room, just with the sisters looking away. They took pictures and kept them.

I was trying to secretly hit on her youngest sister. I feel down and the two of us were stuck on the floor wedge between the coffee table and couch I kept putting my hand on her thighs and almost reached crotch. I turned to this after we played a drinking game and she had to take her pants off, two separate times, once at the end of one and again at the beginning of the next. Never got any more taken off.

One other time I agree to try on a bra in front of my fiance, one of my guy friends, and her two girl friends. My friend got drunk and the hottest girl got tipsy to drunk and agreed to play strip poker with us. However she had no mentality of what was going on passed 10 seconds. So she tried to only get my clothes off but that only made me lose my socks and shoes, while everyone else chose her, thus she ended losing all of her clothes. I caught a glimpse of her vagina when she took off her thong (which she left the room to change into. After she got naked she had to play one full round without covering up anywhere. She obeyed so well.

So those were my two nights of crossdressing in front of someone. Both went well.

Underpants · 10-01-2014, 07:41 AM

Age 16, 2 female classmates, at one of their houses revising for exams one saturday afternoon.
They started talking about make-up, then offered to give me a make-over!
I ended up wearing a very short dress (being taller than them it almost showed the very girly pink knickers they gave me), hold-ups, full make-up, padded bra and a long blonde fun wig.

Luckily there are no pictures

Kelthrai · 10-01-2014, 10:59 AM

Two school ski trips I was on, there was a challenge (both times) to dress a girl as a guy and a guy as a girl. I got picked both times for the "dress a guy as a girl" part, and I passed reasonably well both times. In fact, on the second time, one of the hotel staff actually thought I WAS a lassie! So that was twice in front of about 50 people I knew reasonably well… Pictures survived, unfortunately.

12-03-2007, 02:11 PM	#1
daremaster1 Member Join Date: Mar 2007 Location: east midlands Posts: 52	whos crossdressed in front of someone they know before whos crossdressed in front of someone they no before and explain in detail why it happened

12-04-2007, 04:52 AM	#2
slave_boy Junior Member Join Date: Oct 2007 Posts: 18	xdressed done it front of mg gf once and she was laughing that much she put makeup on me filled the bra and took pics

12-04-2007, 06:59 AM	#3
manjuice Member Join Date: Nov 2007 Posts: 48	ive done it in front of my gf too and also wore a thong and mini skirt in front of her and 3 of her friends for a dare. I was very drunk __________________ male 24 uk Dares i will and wont do. Will do - Crossdressing, humiliating, anal play, risky dares where u could get caught, public (but not fully dressed because i dont want to get found out) Wont do - Anything to do with animals, poo or members of my family Pm me if u can think of a dare for me or want to requests a pic of me doing or wearing something u request

10-18-2012, 11:45 AM	#7
naked_lego Distinguished Member Join Date: Feb 2011 Location: Bricksburg Posts: 784 Blog Entries: 29	In front of my sister 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). __________________ Trans■woman PM Tasks Likes: Photography, Body Writing/Art, Clothing Control, Edging, Denial, Diapers (wearing & wetting) Pee Holding, Butt Plugs, Semi-Public, Nudity, Bondage, Ice, mild spankings Limits: Permanent, Most Pain, Social Suicide, Family, Illegal, Body Waste, curse words Likes & Limits explained

10-18-2012, 11:59 AM	#8
messyalan Member Join Date: Aug 2011 Location: Midlands Posts: 80 Blog Entries: 4	Crossdresser I have dressed for a pub fancy dress and got a good snog with a woman. As I like going out dressed but hidden my most memorable experience was when I met two women and a man without any chance of hiding. They seemed fine about it.

12-05-2007, 09:37 AM	#4
robcam753uk Junior Member Join Date: Dec 2007 Posts: 26	Done it for an ex gf, she thought it would be funny to get me dresse dup in her clothes ( i was little bit drunk at the time, lol) she had me wearing a thong and tights too, lol

12-05-2007, 10:26 AM	#5
StylishKidInTheRiot Member Join Date: Dec 2007 Posts: 49	as a dare, wore my girlfriends panties and bra at a mates party for the whole night. i was drunk at the time though.

10-18-2012, 06:15 AM	#6
shola Senior Member Join Date: Jun 2012 Posts: 207	I was in my (female) cousin's (stuffed)bra, shirt, and shorts once, in front of her and my (male) cousin - though I made it to be more of a joke.

10-18-2012, 12:41 PM	#9
anonimousbob Distinguished Member Join Date: Feb 2007 Location: UK Posts: 918 Blog Entries: 5	A friend came to stay one weekend. We went out and got drunk and when we got home she put a load of her makeup on me while we waited for some oven chips and chicken nuggets to cook. I think if the timer hadn't gone off she would have brought out some clothes for me. She took pictures as she was doing the makeup and has since told me she deleted them. I'm not sure if I believe that or not __________________ 27/M/GMT Ask me anything http://anonimousbob.tumblr.com/ask yes: secluded public, crossdressing,, chastity sexual, anal (including enemas if you want), slight pain, anything else not on the above list I can't think of right now no: openly public/involving others, bodily waste, extreme pain Add me at [email protected] Check out my profile and album on Kinktalk I am looking for a mistress to serve right now

10-18-2012, 01:39 PM	#10
spoon55 Senior Member Join Date: Dec 2007 Location: Lincs/roth Posts: 170 Blog Entries: 3	i did it infront of my gf and whole of my college as part of a charity thing. our sports group dressed in full womens outfit while we played the hair and beauty group at football then had our legs waxed after on local radio

10-18-2012, 01:52 PM	#11
Dareholic getDare Addict Join Date: Jun 2012 Location: 3rd Rock from Sun Posts: 2,329 Blog Entries: 37	The only time I have ever done it; was for a play back in high school. It was a comedy. We where only trying to get a few laughs out of it. __________________ Brian (布莱恩) - Bi-Male (双男性) - Edge Master (边缘大师) RETIRED: THANKS getDare, I HAD FUN. OH, JUST REMEMBER: "Life is not fun, unless you are having fun." - Dareholic "Adam was but human - this explains it all. He did not want the apple for the apple's sake, he wanted it only because it was forbidden. The mistake was not forbidding the serpent; then he would have eaten the serpent." - Mark Twain Yamask

09-30-2014, 11:17 PM	#12
lacelover Baby Member Join Date: Sep 2014 Posts: 1	wearing womens clothing Yes i have worn female clothing and yes i slip into womens clothing in front of my step sister we share our lingerie and clothes

10-01-2014, 07:30 AM	#13
omega10 getDare Sweetheart Join Date: Jan 2010 Posts: 272	I got tipsy with my (at the time fiance, now wife) and her two sisters were staying with us at our apartment. I decided to agree to let them do my makeup and I wore the perkiest bra they had with a low cut shirt and short shorts. I also put a thong on with them all in the room, just with the sisters looking away. They took pictures and kept them. I was trying to secretly hit on her youngest sister. I feel down and the two of us were stuck on the floor wedge between the coffee table and couch I kept putting my hand on her thighs and almost reached crotch. I turned to this after we played a drinking game and she had to take her pants off, two separate times, once at the end of one and again at the beginning of the next. Never got any more taken off. One other time I agree to try on a bra in front of my fiance, one of my guy friends, and her two girl friends. My friend got drunk and the hottest girl got tipsy to drunk and agreed to play strip poker with us. However she had no mentality of what was going on passed 10 seconds. So she tried to only get my clothes off but that only made me lose my socks and shoes, while everyone else chose her, thus she ended losing all of her clothes. I caught a glimpse of her vagina when she took off her thong (which she left the room to change into. After she got naked she had to play one full round without covering up anywhere. She obeyed so well. So those were my two nights of crossdressing in front of someone. Both went well. __________________ Likes: Dare I can do Without anyone seeing (or at least without getting caught) Limits: Parents and siblings, semi-public, day time nudity (unless in bathroom).

10-01-2014, 07:41 AM	#14
Underpants getDare Sweetheart Join Date: Feb 2010 Location: UK Posts: 336 Blog Entries: 2	Age 16, 2 female classmates, at one of their houses revising for exams one saturday afternoon. They started talking about make-up, then offered to give me a make-over! I ended up wearing a very short dress (being taller than them it almost showed the very girly pink knickers they gave me), hold-ups, full make-up, padded bra and a long blonde fun wig. Luckily there are no pictures

10-01-2014, 10:59 AM	#15
Kelthrai Member Join Date: Apr 2014 Posts: 68	Two school ski trips I was on, there was a challenge (both times) to dress a girl as a guy and a guy as a girl. I got picked both times for the "dress a guy as a girl" part, and I passed reasonably well both times. In fact, on the second time, one of the hotel staff actually thought I WAS a lassie! So that was twice in front of about 50 people I knew reasonably well… Pictures survived, unfortunately.