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ever been caught crossdressing? how did it make you feel ?

Started by cc43, December 29, 2008, 09:50:47 PM

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Dani Davis

Quote from: PastyPrincess on October 22, 2014, 12:06:34 AM
I remember this one time I was dressing in drag for my girlfriend because we both enjoyed it and I had a great time and I guess some of the makeup just didn't come off when I went to school the next day and this guy in class pointed out the blush on my face and I didn't know how to feel, because I don't know if he was judging me or not, and it confused me.

Back in the mid/late 1990s, I had a houseful for 4th of July festivities.  What most of the guests didn't know is that for the two days prior to everyone showing up, I was completely dressed, make up and all.

Even though I had tried making sure ALL of the make up was off my face, my 9 year old nephew looked at me (as we were all sitting in the living room conversing) and said, "You look like you're wearing lipstick, Uncle D.!"

Thankfully, most of the adults in the room knew who I was but like you, it was one of those moments of "how the hell do I respond??"
There are few limits - just unexplored options.
Mariette Pathy Allen
Author of Transformations
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amyd

My mother walked in on me a couple of times. It made me feel highly embarrassed but her response was fine. In fact from that point she would give me clothing and shoes so it was probably one of the best mistakes I made.  :D
Amy Xx
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Sandy74

When I was younger at around thirteen or so I would constantly steal my sister's underwear until it got to the point where my parents brought it up to me and I think I apologized to my sister for taking them and returned them. I am not sure if they knew I was wearing them or what not. That's the only moment I have been close to being caught cross dressing.
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Polina

I think there should be some safe places for that) Like we have in St Petersburg, Russia)))) To try outfits, to learn how to apply make up, to treat oneself with a great photosession with a new look)))) But your stories are so interesting
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barbie

Quote from: Sandy74 on November 21, 2014, 09:26:00 PM
When I was younger at around thirteen or so I would constantly steal my sister's underwear until it got to the point where my parents brought it up to me and I think I apologized to my sister for taking them and returned them. I am not sure if they knew I was wearing them or what not. That's the only moment I have been close to being caught cross dressing.

Kids are curious, and your parents probably did not related it to ->-bleeped-<-.

barbie~~
Just do it.
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Clhoe G

Haha Yeah my mum caught me with eyeliner  on because I couldn't wash it all off in time..
o n mineral power once or twice, my excuse was rockers wear makeup because I use to play a little guitar until it broke
Thank-you scorpions...

For looking like Goth lobsters.  :laugh:

Quote.
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Wow, I could have sworn I've been on HRT for longer.
O well this ticker will help me keep track.

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Sammy

Nope, never. I was too smart and cautious to be caught :D
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LauraSpiral

I got caught sleeping in my underwear once... My parents weren't impressed! After getting changed into my "male" clothes, I had to explain what was happening, but they still didn't understand. They kept looking it up like it was a disease. That sucked. :(
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Ally.G

I have been a couple of different times and under a variety of circumstances. I  would dress up (as I call it), then drive around in my vehicle into Toronto and other cities where people did not know me or my vehicle. I have corresponded with others who were into relating experiences and fantasies. I would often find places to park and sit dressed up, while writing. I also alternated playing with myself when I got turned on from reading letters and writing replies. There were a couple of times when I stepped out of my vehicle, late at night to post letters/drop them into a mailbox, a car happened along and the guys in it would drive by hooting, whistling and yelling as they passed by. They only were able to see a back view of what appeared to be a tall, slim brunette, wearing a short skirt and heels. Those times it turned me on. In another scenario, I was in a conservation area late at night walking around and a guy approached me, initiated a conversation which turned to me giving him oral sex. While I was doing this other people walked by on a nearby path and could see my head bobbing up and down. They could not see my face due to the wavy shoulder length brunette wig hanging down. I wanted to stop when I realized these people could see what I was doing. Only the guy I was doing told me that they think I'm a female and not to stop. There was another guy who happened upon this scene, who kept walking by, back and forth, looking or watching. I paused in what I was doing to look up and over to see this person. Again the guy asked me to go back to doing him. Afterwards the watcher was nowhere to be seen. We figured he was behind some bushes jerking off.     
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shinyJ

SO Last night, My wife was out with our Daughter, and I thought I had the whole house to myself for the evening.  I got my stash out of the attic and put om some sexy panties, and got out some of my toys.  I was right in the heat of some hot backdoor self play, when I heard a car pull up.  OH CRAP!!!!!! My wife and daughter had come home, and here I was in the bedroom. Femme clothes and heels splayed out all over the place and I was pleasuring myself.  I scurried to shove all of my stuff under the bed. But I forgot to put away the bag on the bed.  I scurried into the bathroom and locked the door, and then I realized that I left a big bag of lingerie and toys on the bed.  I came out of the bathroom and my wife was standing there looking at the items in the bag.  for about 20 minutes I was speechless, then I finally came out with it. That I like to crossdress and I like anal stimulation.

She seemed over cool about it, and we aren't sure how this will pan out.  I'm hoping we can stay together as she has said she's pretty open and cool about it.  She suggested finding a community where I could talk to others about it, so here I am.  The day after my wife found out that she married a crossdresser. 

I'd love to hear other stories, or maybe a little reassurance that a marriage can still make it even with this.
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alexbb

i never got busted as i was super paranoid and cautious but i had a little dress i found in a box of old stuff which i claimed. i used to feel so good wearing it id often go to sleep in it and then im pretty sure my mum saw a corner of it waking me up for school. she never said anything and says she doesn't remember now.
i went out with all my friends last night, straight guys and girls, dressed up. it was so great. i feel like i can let the past 30 years of worrying and being scared about being caught crossdressing go after going out in public as a 'girl'.

YoungZep

Room mate caught me with nail polish on my toes. Hid from him for a week. emberrased beyond belief, but never mentioned anything to me about and we still talk and hang out so I guess he already came to the conculusion im weird and doesn't care :P

jessi9

I was caught by my mum when i was about 7 or 8, she was mortified and sent me to a child psychiatrist. I learned to hide it better after that  :)
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darlene143

The first time I went out dressed up I took a walk at 2 am and all was going well feeling comfortable when a car drove by and it was the local police they turned around and shined the spotlight on me got out asked me some question then asked for my I.D. and I didn't have it on me so they drove me home I gave them my drivers liscence and just stood there while they checked it out.  my heart was pounding so hard they left and couldn't believe how turned on i got standing there as they looked at me :)
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Kelly_1979

Not straightforward. I haven't practically cross-dressed anyway. Only when I was 13-16 I used to wear one of my mother's dresses. I guess some day my mother found out because the way I had put the dress back in the closet. Back then I dismissed trying to say "just forget it". Other than that I had worn jewellery, nail polish and some other things but I was quick to take them off before my parents got back home (That was like ...20 years ago). I was so terribly scarred of my parents and neighbors finding out. Maybe that's one reason why I didn't really cross-dress. It wasn't really sexual though and sometimes I hit myself for trying to forget it all those years.
Trying to emerge to my real self
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jessi9

Just got sprung by my alcoholic neighbour...he called me a ->-bleeped-<-got, I told him to eff off cos I'm bigger than him and could hurt him  lol
What a difference getting older makes  ;)
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Hannah Samira

The first time (and the last time so far) that I wore mascara I didn't wash it off properly. When my mum, dad and sister got home the first thing each of them said to me was "oh, it looks like you're wearing mascara!" Somehow I managed to convince them that it was because I had been sitting in a dark room for hours while they were gone, no idea how I got away with that!!

The second time I got caught was when I accidentally left my underwear inside my sister's jeans when I was trying them on one day. My mum and sister called me in to her room and said "these are yours" giving me the underwear. Then my mum looked at me and said "have you been wearing N******'s jeans?" I just said no and walked away nervously, that was the last I heard of it.

The third and final time I got caught was the only time I ever tried nail polish - huge mistake in the situation I was in!! My sister was staying at our cousin's house for the week so I took this opportunity to snoop around her room. I found a lovely red nail polish and put it on without thinking. It was only after it had dried and I had admired it for a while that I realised she had no nail polish remover!! In the end I genuinely attempted to sand it off with sand paper but in the end there was still some left at the bottom of my nails. My dad came home and I was talking to him, trying to hide me hand. He instantly noticed it, grabbed my hand and looked at me with such a mixture of disbelief and disappointment. I'll never forget that look. He asked me what it was in a stern voice and I just burst out into tears. I looked for the easiest thing to blame it on so I just bawled "I miss my sister!!" We hugged it out and that was the last I ever heard of it.

This is the first time I've ever written out all the times I've been caught and to be honest it does make me feel a bit confused. Looking back on it, the reactions that everyone had were nowhere near as bad as I had expected!!Granted I wasn't completely caught in the act, but still kind of intriguing!! :)

xx
Twitter: @HannahSamira14
Instagram: @hannah_samira14

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torig

Yes,by mom when I was 6 years old wearing her pantyhose.I felt a little guilty and she knew there was something different about me after that.Let me have the pantyhose,she was going to throw them away.
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puddles420

Ive been caught at a fuel station filling up truck. Nervous but felt good. Was wearing pink aeropostale with skinny picetless jeans and thigh high buckled heeled platforms ;) fav!!! Have tons of new clothes since but was a rush:)



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Mariah

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