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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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valerie anne

Hi CindyCD,

I loved every minute of clicking around in my heels, exposing my black bra straps under my tight see-through top and pushing out my boobs. I am quite relaxed about it and I am sure my women friends know and really don't mind.

Although I have got great legs in sheer stockings and heels (I was told so!), I am not a gorgeous pretty gurl like you, and I still look like a man in lipstick & mascara.

If I made myself up like I did for halloween, it would just look silly. I can pass as a frumpy woman in sweater, jeans and boots, but my horrible face simply doesn't allow me to wear a sheer top, plunge bra, tight skirt, sheer stockings and pretty heels with any conviction.     

     
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CindyCD

Quote from: valerie anne on November 25, 2013, 03:40:25 PM
Hi CindyCD,

I loved every minute of clicking around in my heels, exposing my black bra straps under my tight see-through top and pushing out my boobs. I am quite relaxed about it and I am sure my women friends know and really don't mind.

Although I have got great legs in sheer stockings and heels (I was told so!), I am not a gorgeous pretty gurl like you, and I still look like a man in lipstick & mascara.

If I made myself up like I did for halloween, it would just look silly. I can pass as a frumpy woman in sweater, jeans and boots, but my horrible face simply doesn't allow me to wear a sheer top, plunge bra, tight skirt, sheer stockings and pretty heels with any conviction.     

     

I'm glad you had fun Valerie Anne. I bet it felt great to show off your nice legs. Maybe with the right wig and make-up you would surprise yourself. And thank you for the complement. I was self-conscious about posting the pic, but now I feel ok. You made my day! Hugs and best wishes.

Cindy
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stephanie203

Growing up I thought I was very careful putting mom's stuff back, refolding etc. but it seems not well enough a couple of times so see accused my sister of going through her drawers and she denied it and it was as if she didn't want to have to believe it may have been me the way she asked me but had already dismissed the possibility.
She's incredibly liberal always interested in gay and transgendered people so while I was naturally nervous just in case, I always hoped she'd be understanding and supportive if I was ever caught, directly confronted, etc but when I was ultimately caught she was anything but. I snuck to a CD boutique and bought a few things I think I hid very well in places that would have been difficult for her to snoop. One of the things I bought was a wig I could have sworn came in an unmarked box. I threw the box away in my bedroom wastebasket. She was cleaning and emptied the wastebasket finding the box and apparently had some wig marking on it. Freaking out over her discovery she calls me while I'm at work and confronts me. Doing some quick thinking and thinking I was believable I told her some videotapes I mail ordered were in the box. It's too bad she was so freaked out saying things like "We can get you help" instead of being accepting and supportive and offering her help. She dresses so well and is so stylish that her help would have been great and the way she always has to over do everything I would have hoped it would have carried over to that, too. I really would have liked coming home  to find lingerie, pantyhose, pretty dresses etc. waiting for me but that'll never happen.
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CindyCD

Quote from: stephanie203 on December 30, 2013, 06:43:41 PM
It's too bad she was so freaked out saying things like "We can get you help" instead of being accepting and supportive and offering her help.

Sometimes we have to show some patience, give her some time to digest the information. I hope it all works out.
Best of luck.

Hugs,
Cindy
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FalseHybridPrincess

My brother one time had caught me...on elementary school i think...

somehow I managed to cover it up...

aaaahhh...
http://falsehybridprincess.tumblr.com/
Follow me and I ll do your dishes.

Also lets be friends on fb :D
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barbie

Quote from: FalsePrincess on December 31, 2013, 11:50:26 AM
My brother one time had caught me...on elementary school i think...

somehow I managed to cover it up...

aaaahhh...

No problem. At that age, ....
I was first caught by my mom while wearing silk stockings when I was 4 yrs old. What I remember is that they were unexpectedly too big for my legs, and I was a little bit perplexed and disappointed.

barbie~~
Just do it.
  • skype:barbie?call
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LivingTheDream

I have had numerous close calls and even been caught a few times, sorta. One time when everyone was away. I was wearing my mom's clothes in her bedroom and the front door opened! I only had her clothes on, my clothes were in my bedroom (other side of the house). I wasn't expecting anyone and my alarm didn't warn me of anybody's presence (bad dog!). I crawled under my parent's bed and hid. Omg I was lucky I did, my dad walked into the bedroom and then left the house soon afterwards. I have had many times where I was wearing female clothing and had the dog, or dogs, bark and warn me that someone has come home so I could change real quick, still do.

One day I was wearing my mom's bra outside for some reason when I was young, prolly early teens, and my brother touched either my back or shoulders. He was like, "omg you're wearing a bra". I was like, "No I'm not", moved away a bit, then ran inside a few min later and took it off lol. Can't really hide the band or straps of a bra. He prolly thought I'm gay, or still does. Never heard a peep about that, guess that counts as being "caught".

I think somebody found my stash of feminine clothing that I had hid in the bathroom, under the sink counter. I had it so I could lift the bottom piece up and had lots of room for things.

The icing on the cake was when I was in my 20's however. One day I was washing my girlie clothes and put em in the dryer, and forgot about them. I fell asleep and when I woke up I was like, Oh $*%(.... I snuck out of my room to check the dryer and you know what, all my things where on top of it. I had some of my mom's clothing and other things that I had gotten over the years in it. Ofc, after I saw my things on the dryer, my dad comes up behind me and questions me about it. I lied and said I was washing a friends things, but he knew I was lying because I had some of my deceased mom's items with them (it was just me and him living at home at that time). It was weird for a few days with us, understandingly, but we never talked about it, and since he passed a few years ago, don't have to worry about it. I wonder if he ever mentioned it to my brother tho?

So ya, now I try to be much more careful, but still I come close to getting caught quite a bit...

-Kelly

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GeorgetteSometimes

Myself, I was caught in the very most wrong way. My ex wife and I had already been having issues, but she was well aware of my dressing and would if fact buy me panties and nighties to wear, I thought all was cool, she even one night suggested I shave my armpits too, so that she could lick them.
One Sunday, as I was fully dressed as Georgette and my stepkids were gone with their dad, she came down to the rec room to let me know the kids would be home soon, and I should change back. NOT 2 minutes later my 16 year old stepson walked in for some reason. Had I just pulled some covers over myself (the tv was on) and pretended to be dozing all probably would have been cool. Instead this dummy blurts out 'hey can I get some privacy please?' Cussing and disbelief from him, too much shock for us both. I am single now and dress here as I please. Meanwhile I took all the heat never letting on that she (the ex) was very much an accomplice.
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sagitilicious

I had my own room with a bathroom that didn't have a shower or tub, so even though others used it, the bust was undeniable. I used to keep a bra and spaghetti strap top and denim skirt behind the heater in my bsthroom. I walked into it after school to find all three folded on the corner.

Dad did it, or someone did and told him because he started blackmailing me with it for years. It began the end of my cding. I hate that man, especially since my parents rncouraged me to wear nightgowns as a kid. They had a hand in starting it and still dad blackmailed me.
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Melody-Yvonne

I to have been caught crossdressing.   By my wife, who is , to put it mildly, 110 %  unsupportive, to include certain, not so nice, pronouns and so on.   So, to keep her from seeing anything, I underdress at work only.   The only time I can really be Melody Yvonne is when she goes to visit realitives in other states, like she is now.   If she found out I was still dressing?  It would not be good.     Oh!   And by the way,  I am knew to this site.  And I really enjoy being  Melody Yvonne, which is the name my mother was going to give till she found out I wasn't a girl.

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meryl21

I wasn't exactly caught crossdressing but this is what happened:

I have been dressing in the afternoon after work. My wife gets home early and comes upstairs. Duh, I thought everything was put up but my new Pleaser pumps WERE NOT. They were still in the box(I don't know if she opened the box...guess is she did). She said 'are you crossdressing?'. I didn't know what to say, only that I would be getting rid of them. I did a mini-purge that day and have done a full purge since then. OMG, all the money I've thrown away purging. And I go right back. God and I have talked about this and I look at it as one of His blessings...to be able to see my 'other side' and be okay with it.
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barbie

Quote from: meryl21 on May 13, 2014, 06:55:15 PM
I wasn't exactly caught crossdressing but this is what happened:

I have been dressing in the afternoon after work. My wife gets home early and comes upstairs. Duh, I thought everything was put up but my new Pleaser pumps WERE NOT. They were still in the box(I don't know if she opened the box...guess is she did). She said 'are you crossdressing?'. I didn't know what to say, only that I would be getting rid of them. I did a mini-purge that day and have done a full purge since then. OMG, all the money I've thrown away purging. And I go right back. God and I have talked about this and I look at it as one of His blessings...to be able to see my 'other side' and be okay with it.

So, your foot size is the same as your wife's?

barbie~~
Just do it.
  • skype:barbie?call
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Jill F

Never happened to me because I didn't crossdress.  OK, I effectively did until I was 43, but that was all in boy clothes.   I didn't ever hide the fact that I was transgender and told my wife as soon as I could sort of admit it to myself and told her that I needed to borrow some clothes.  I thought keeping a secret like that from her was probably going to be worse than telling her I was trans in the first place.  I didn't think I could have handled having some 'splaining to do if I hid it and it was accidentally discovered.   Plus I REALLY suck at lying.
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Khaleesie Fiona

Well, yeah, kinda. My wife caught me multiple times before I decided to bring her 'in'. The other times wasn't so much caught dressing as caught in something. My wife has recently starting painting my toenails and I'm currently on a business trip out the country (S. Korea). I went for a massage (the stress has been to much on this trip) and the female masseuse looked at my toenails, giggled and asked me if I was a girl.

Then the other night, my coworker came to my hotel room door and I forgot to put on socks, when I opened the door, he said 'nice nails'. I thought I would die but gave the excuse that my wife was fooling around before I left and we forgot to remove it. I think he bought it....... LOL
-Happy to be a little more open with my femininity-
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meryl21

Quote from: barbie on May 14, 2014, 12:12:41 AM
So, your foot size is the same as your wife's?

barbie~~

Nope. I wear a womans 17. Sure wish I could find some sandals in that size. All I can find are pumps.
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Dani Davis

Never been caught that I recall, but was later told by my parents they suspected something was amiss when I was in my teens.  I had the great fortune of having friends and family that when I did "come out", really didn't have a care about it one way or another.  I was always known to do my own thing and the rest of the world be damned so I think most of them just figured it was "just another Dani, thing".

There were some rare occasions outside of Halloween that I also had the opportunity to be myself around a few of them.  But being sensitive to others' sensibilities, I tried not to be too much in their faces about it.

It was interesting at times when there were gatherings at my home.  I live in a two story house and the only bathroom downstairs is through my bedroom.  Folks passing through my bedroom and into the bathroom got an eyeful of frills, shades of pink and rose floral patterns.

It did garner some gossip among the few who were not in the know...smile..

Fun times for sure...
There are few limits - just unexplored options.
Mariette Pathy Allen
Author of Transformations
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ImagineKate

Caught by my mom only once ever when I was like 4...
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Daniolivia

When I first stated experimenting at the age of 14, back then my mum used to work night shifts, one night she came into my room and my blanket wasn't covering me properly and she saw that I was wearing a pair of stockings and a skirt, we had some rather nasty arguments (more like her shouting at me with me not saying a word), it simply went away gradually though I stopped with crossdressing, until recently. (I am now 20)
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FrancisAnn

When young 4-5 years old I used to love to play dress up with my mothers clothes, lipstick, etc... She saw or I guess caught me & was not upset at all. I was just having fun like any little girl would. She just told me not to get anything dirty or break anything. It was such fun & I've always enjoyed being a girl/woman. My mother wanted a little girl anyway so everything was fine. I really thought I was a little girl anyway.
mtF, mid 50's, always a girl since childhood, HRT (Spiro, E & Fin.) since 8-13. Hormone levels are t at 12 & estrogen at 186. Face lift & eye lid surgery in 2014. Abdominoplasty/tummy tuck & some facial surgery May, 2015. Life is good for me. Love long nails & handsome men! Hopeful for my GRS & a nice normal depth vagina maybe by late summer. 5' 8", 180 pounds, 14 dress size, size 9.5 shoes. I'm kind of an elegant woman & like everything pink, nice & neet. Love my nails & classic Revlon Red. Moving back to Florida, so excited but so much work moving
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PastyPrincess

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.
Seventeen and strung out on confusion,
Seventeen and coming clean for the first time,
no mom and dad will never understand,
what's happening to me.
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