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Thread: Most embarrasing moment when caught as a child.

  1. #26
    Aspiring Member Alex!'s Avatar
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    Oy. I was never caught wearing women's clothing and makeup. But there were two incidents of note. My mom discovered my very poorly hidden stash of various items. I believe this was 1984 or something. I came home from school, and she didn't talk to me. I had no idea why. Then dad came home. He took me aside and talked to me. I don't remember what he said, only that mom had called him about it. He didn't seem hugely concerned, now that I reflect on it, but clearly he wasn't thrilled either. Over time, mom moved on, of course. It represents the most embarrassing event in my life. Even to this day I would love to erase it from the historical record!

    Then a few years later, I was almost caught by my dad. Everyone was out of the house, and that meant I had a few hours to dress up in mom's yellow dress. I went all out with makeup, shoes, hosiery, and even messed with my hair. I was in my bedroom admiring myself when I heard keys in the main door, and the door opening. What the hell!? Dad had come home early. I somehow had to run across the short distance between my bedroom and the bathroom to get cleaned up. I was one flight of stairs above the living room, so theoretically anyone in the living room could look up and see me. I kept looking to make sure the coast was clear. It was. I made a dash for it and, of course, dad walks through the living room. He didn't see me though. I cleaned up and afterwards pretended I had been taking a crap. What a nightmare it would have been had he seen me. We would have both been scarred to life. After that, I didn't dress until college many years later...
    Alex Forbes
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  2. #27
    Member dawn459's Avatar
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    mostembarassingmomentwhencaughtas achild

    My most embarassing moment came at 14 by my dad i had hid a pair of moms panties in my room to wear+help releive my self so i did and went to the bathroom to cleanup+get ready to go back to bed+was putting the panties backin the dirty clothes hamper+had forgot to lock the door when dad walked in to use the bathroom+he asked what i was doing with moms panties imumbled something+he said dont do that it could lead to blindnessand walked out that was 53 years ago not blind but do wearpanties+glasses.

  3. #28
    Silver Member justmetoo's Avatar
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    I never got caught. For better or worse. Maybe my sisters would've helped me if they had known.

  4. #29
    Silver Member DanaR's Avatar
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    When I was in grade school and about 7 years old, I would come home and sometimes dress up. It was easy, as would be the only one home until about 5 in the afternoon; which is when my sister and mom would come home. One day after school, I was dressed up and my sister (ten years older) came home early and found me in my moms bedroom hiding in the closet, wearing panties and stockings. I don't think that she told my mom, but years later she told my wife after we got married. When my sister told my wife, my wife didn't know that I dressed up and didn't tell me about my sister telling her until after I told my wife that I crossdressed. My wife has told me several times that my sister brings it up occasionally and laughs about it. BTW, my sister doesn't know that I still dress up.
    Dana Ryan

  5. #30
    New Member Ashley84's Avatar
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    when i was really young, im gonna say somewhere between 3 & 5
    my aunt dressed me up as a girl. my parents didn't think anything of it because it was my aunt's idea.
    they had a good laugh
    in fact I think they still have the picture.

    I didn't actually start crossdressing for my self until later in life. I think I was about 20 when I started, but it was a once in awhile thing. I didn't start going all out until I was about 26 or 27. I guess I'm a late bloomer in the crossdressing department.

    although when i was 14 or 15 I started doing something similar to crossdressing. when I would get out of the shower instead of wrapping the towel around my waist like most men do. I wrapped it like a women would & i would pretend i was wearing a dress.

    I think i also wore nylons once when i was about 16.
    I never got caught with/in women's clothes, but I kinda wish I had.

  6. #31
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    Got caught more times than I can remember. Was sent to a doctor the second or third time (G.P. of all things, but then again this was the 50s' and 60s' and in a town of about 2500 people. After that parents just ignored it. When I came out in 1975 they were not surprised.

  7. #32
    Silver Member STACY B's Avatar
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    The closest I ever was to getting BUSTED-- I mean out and out Busted was when I was about 15 or 16 I guess my 2 sisters were long gone as I am the youngest, Never messed with my moms stuff because I had an older sisters that were different in every way. One was a Tom boy who NEVER dressed up at all.
    The other was a girly girl all the way and mine you this was late 70's early 80's back when everyone wore pantyhose even with shorts, lol. Anyway my oldest sister was the Girly one an moved away and left almost all of her clothes and shoes so you already know (Whats Up) and I took Full advantage Trust Me!

    Being that young and not hardly ever dressing all the way mostly just a few quick things from time to time this time was different to say the least. If was a weekend mid afternoon Mom was gone and not returning anytime soon Dad was at work out of town and I was all alone to do whatever I wanted, So I thought, My oldest had this Prom Gown and I had my eye on it for awhile so why not I said, This time I went to the bathroom and put on some makeup, Like I said not very offen did I do that because it was so hard to remove and I knew that.
    Anyway after putting it on BADLY I might add down to the dressing part, Panties , Pantyhose, Bra, Slip, Formal Dress and Heels, I was looking at myself in the Mirror and Guess what? Ohhhhhhhhhhhhh YEA, My middle sister drove up, We had a small house and a very short driveway and a shorter walk to the front door, There I was couldn't run to the Safety of the bathroom like everyone else does, To clear of a shot to see so the only thing I could do was go into her old room, No locks, Nothing, She seen me, No way to get out of it at all, So she comes into the room and my Dumb self goes into the closet, lol,, What the hell was I thinking?

    Anyway you have to know this sister, She was a WILD ONE, So it didn't take long to figure out she was DRUNK, So what I said when she was pulling on the door was I just got out of the shower and was getting dressed and saw her and just ran into the closet, As I said she was drunk and pulled on the door a few times laughing and yelling and ended up getting what she came for a lost interest and just left. Boy was that a close one, Needless to say I locked the doors after that.
    An I wasn't much on that makeup for a long time after that Crap,lol. Trust me that's just one of the MANY CRAZY times for me !

  8. #33
    Senior Member Ally 2112's Avatar
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    I never got caught although my mom did mention a few times about how clothes of hers seemed to be out of place or someone besides her had tried them on .I never said a word and i know i would of denied it .I also came very close to getting caught a few times im not sure what would have happened
    I have a hubcap diamond star halo

  9. #34
    Multi-Blogger Barbara Black's Avatar
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    I was caught right in the open, on our street. The girls of the neighborhood were playing dress-up, and left a pair of dresses across the street while they went across the road. I suggested to a friend that it would be funny to put on the dresses and then go at the girls. Well, we were caught getting dressed, got horribly embarrassed, dropped the dresses, and ran!! I must have been really small because I still recall how far the distance across the street seemed to be, but it was really a very narrow street actually. I remember thinking that they wouldn't see us from all the way over there. I was wrong. LOL

  10. #35
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    I was never caught in the act. My mom was a secretary and wore dresses, heels and pantyhose every single day. So there was always things laying around to try on. I did tell her I wore her nylons once when I was in grade school. I never wore her things very long. If I saw something I liked I put it on quick and then took it off. I didn't wear full outfits until my 20's.

  11. #36
    New Member Amy1980's Avatar
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    I was caught twice growing up. the first time i was 10 and my brother walked in on me trying on one of my moms bras. i told him i was putting together a halloween costume. the next time i got caught and the reason i grew ashame of myself and am still in closet to my family is when i was 12 i dressed all the way up even makeup. and my mom came in. she caught me and made a big deal about it. putting me into the corner and poking fun at me pointing and laughing and makeing jokes. after that i made sure if i ever tried anything on it was a mission not to get found out. i would lock doors set traps take pictures so things went back as i took them. i never got caught since.

  12. #37
    Senior Member Jennifer in CO's Avatar
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    I've shared before about my mom's DADT approach in my teens but the closest "embarrassing" moment was actually her doing...trying to embarrass me in front of my friends. Halloween when I was 11 she let me go out dressed as a girl..."all the way". Panties, garter-belt and hose, one of my Sisters padded early bras, Sis's maroon velvet micro-mini dress - so short it had a matching pantie cover, 2 inch heeled white go-go boots, maroon painted nails and full "teen" makeup. Not gaudy, just what a 14/15 year old would wear in 1968/69. My shoulder length hair got a wet-set when I got home from school. At about 6 I was put under the hair dryer and was quite curly (up-curled) for the evening. (I think that was Mom's first attempt at embarrassing me - making me wear curlers all afternoon including dinner with Dad). Went out T-or-T then was to go over to a friends house for a party. Well, when I got back from T-or-T Mom told me she couldn't find her cold cream to remove the makeup so if I'm going to that party I have to go as I am or as a boy in makeup.
    I went as I was.
    No one laughed, the girls thought it was cool, and parents who were there and didn't know me asked me several times why I didn't wear a costume or treated me just like another girl in the mix. After an hour or so, even those who knew me treated me just like one of the girls...including the girls. It was great. One of the other girls at the party gave me a lift home when her parents came for her. They thought I was just another girl. Mom was waiting up for me and "amazingly" she had found her cold cream when I got home...but not the finger nail polish remover. So I went to school the next day with maroon fingernails, curly hair and the perfect excuse... like I minded. She didn't "find" her polish remover till late that next night (two days) but for some reason didn't make me wash my hair till Sunday morning before going to church (three or four days if I remember).
    So, was I embarrassed? No. Was she trying to embarrass me? I'm guessing yes

  13. #38
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    I got caught quite often wearing others tights but cannot remember feeling embarressed?

    Julie

  14. #39
    AKA Lexi sometimes_miss's Avatar
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    Getting out of the cold lake water at boy scout camp, and going right into the boathouse to change. The cold water having done it's worst, my male genitals almost completely disappeared, making me look like a girl. Then the scoutmaster taking me to be checked by the camp nurse to check my genitals to see if I really was a girl. I prayed for an earthquake to make a giant crack in the earth to swallow me up. That was on the second day of camp. I still had to endure the rest of my time at camp with all the other boys thinking I was a girl. I really thought they were going to kill me.
    Some causes of crossdressing you've probably never even considered: My TG biography at:http://www.crossdressers.com/forums/...=1#post1490560
    There's an addendum at post # 82 on that thread, too. It's about a ten minute read.
    Why don't we understand our desire to dress, behave and feel like a girl? Because from childhood, boys are told that the worst possible thing we can be, is a sissy. This feeling is so ingrained into our psyche, that we will suppress any thoughts that connect us to being or wanting to be feminine, even to the point of creating separate personalities to assign those female feelings into.

  15. #40
    Crossdresser Taylor186's Avatar
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    Quote Originally Posted by Ally 2112 View Post
    I never got caught although my mom did mention a few times about how clothes of hers seemed to be out of place or someone besides her had tried them on .I never said a word and i know i would of denied it .I also came very close to getting caught a few times im not sure what would have happened
    My story is similar. I remember going into my mom's room in my early teens and trying on a pair of her new, still-in-the-box stockings. I stupidly runnered one putting it on ... panicked ... quickly took them off and refolded them and replaced them like I had never been in her room. As Sargent Schultz would say back then, "I know nothing." A few days later she generally mentioned with my dad and brother present that she had found one of her new stockings had a runner in it. I looked over at her and she was looking directly at me. Nothing more was said but yes, I too would have denied it if asked directly. I tried to be more careful from then on.

  16. #41
    closet dresser Melissa73's Avatar
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    i got caught many many times! and when i came out to my sister, i swear she would say she remembered... but she admitted she let it all pass without another thought, while i held onto the memory and fear that everyone knew!...
    BUt anyways the most funniest time i was caught (not by a person) but caught outside........i was living in a local motel (where i was employed. as a condition for work, the owner gave me one of the larger rooms to live. nice deal). Anyways, on this particular night i was off, and the whole city had a blackout (no power). And so i dressed up in a bra-panties, whit top and demin skirt and socks. And being daringly, i opened the door and looked down the hall. Well, my cat escaped! And so i went after him (still dressed) and low and behold the door shut. Being a hotel room (doors lock automatically). Well i grabbed the ca and walked to my door to find i was locked out. i was paranoid! what was i to do?

    Then i remember the maintence room was usually open (and i could find a key) ... so, carrying my cat, i walked down stairs in my outfit... scared someone would see me. BUt i forgot, no lights.... i could not see the key area. using my brain, i grabbed a comforter and covered up and wen to the front desk and asked for a key.... and then went back up.... but it was sooo scary!!!! next day i was waiting for someone to comment but noone ever did

  17. #42
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    Yes, I was "caught" a couple of times. However my uppermost thought in reading these stories was- Wouldn't it be good if it didn't matter and children were just allowed to dress as they liked in whatever clothing they most desired.

  18. #43
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    Not caught in the act, but mom mentioned she'd found my skirts in my bedroom. She promised to tell nobody else and asked if I would like advice on dressing.

    I never took her up on the offer as I was so embarrassed.

  19. #44
    ashleighfl
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    I was only caught dressed twice. However my stash was found a few times growing up. The first time I was caught, I was 16 my sister had just moved to college and I had moved into her old room. She had left some of her older clothes in her closet. My parents were out of town for the weekend and i took the chance to dress. I had dressed in panties, bra, a tank top and cheer leading shorts. I went outside for a walk (I grew up on a farm, so I was safe), however when I returned I walked in and my sister was in the living room. She had come home for the weekend and I didn't notice her car in the driveway. We ended up talking the rest of the night about my cross dressing and I thought she was OK with it. A few weeks later she would tell my parents about everything and I ended up having to go to counseling.
    The other time I was caught was by my best friend. We were 18 and after a night of drinking we ended up staying at his house since his parents and sister were gone. That night I decided to sneak into his sisters bathroom where she usually kept her dirty clothes. About the time I got the panties, bra, and dress on I hear my friend ask what I was doing. I didnt know what to do, so I acted like I was still drunk. He laughed and said he would get me some water. I quickly got undressed and climbed back into bed. He never said anything about that night.

  20. #45
    Member JessMe's Avatar
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    Jeez... I got caught so many times that it's really hard to pick just one to take the grand prize of embarrassment. Lol ...it always came with the same sinking sensation and despair at the loss of my treasured wardrobe, BUT if I had to choose just one, it would be one that actually reared it's ugly head again just a week or so ago, at age 31.
    Once, when I was a kid, I went on vacation to visit my aunt and cousins... and somewhere during that two week period, my mother decided to clean my room. Of course, me being a kid at the time, I assumed that my super awesome hiding spot for all things naughty (in a backpack under the bed), would NEVER be discovered. How could it? So clever. Lol
    Anyway, the phone rings at my aunts... it's mom. She wants to talk to me?? "Is there anything we need to talk about? Anything you want to tell me? " I casually said no. of course the thought crossed my mind that I was busted, but after another week of vacation and playing dress-up with the cousins and all was forgotten. Until I got home and saw the two lighters from within the aforementioned bag 'o' naughty (yes, I was also a firebug. Lol) sitting on the microwave... a quick check confirmed my suspicions. I was BUSTED.
    Nothing was ever said about it until a week or two ago when my dad, a few bourbons into a casual coversation said in his Appalachian Drawl "I thought yer mother'd sh** when she found 'em panties in yer room when you's a keed." ...cue the same old shock, shame, and horror... like it was yesterday all over again. The conversation turned to something else when he sensed my anguish, but yep... that happened. Lol

  21. #46
    Member Tabitha_Lynn's Avatar
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    I remember one time as a teen, I was caught by my mom while wearing my sister's swimsuit.

    It was late at night and I had slipped from my room while wearing my sister's one piece. My mom came out of her room and caught me. She sat me down on the sofa and had the "are you gay" question for me. After a minute or two, which seemed like hours at the time, she told me to go change. Nothing was ever said about it again.

  22. #47
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    I have a few:

    1, i got caught looking at lesbian porn and denied it.

    2, My dad found some of my moms lingerie hidden in my bathroom ( I just hit puberty then). I denied i put it there.
    "Be who you are, and don't let anyone tell you otherwise"

    "If you're not transgender, you don't understand, so STFU"

  23. #48
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    I was never caught. But I think my mom knew. When I was home alone sick or something I would try on her dresses. She also had several 80s secretary style blouses. Satin with billow sleeves and pussy bow. I had long arms so the sleeves were a bit tight. BOOO!!!! anyway, she had a red dress with puffy sleeves and a belt. I was trying it on and saw she came home. I quickly took it off. I forgot to put the belt back. She was cleaning and asked why her belt was out. She never said a word to me asking if it was me that did it.

    Gwendolyn

  24. #49
    Krysten Krystenw's Avatar
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    The neighbor girl and I had played the whole summer as sisters but when school started, Mom started dressing me up as a little boy to go to school.
    I couldn't figure out why.
    My dad was a roughneck in the oil fields and was gone for weeks at a time.
    I never understood why I never got to wear dresses when he was home.
    Anyway, for Halloween my Mom and the neighbor lady decided that her daughter and I should go to school as twins.
    They put us in frilly little dresses and had our hair in ringlets, we thought we were pretty special.
    That was until we got home from school.
    I guess the rig had shut down and my dad was home several days early.
    When he saw me he had a fit.
    He took me and put me in the car and we went to the barber shop and he had the barber give me a butch haircut.
    I couldn't believe it. I was so humiliated.
    When we got home and my mother saw what he had done she proceeded to have a fit herself.
    It was quite some time before I was able to wear a dress again.
    I still cringe 60 years later when I think of that.

  25. #50
    Junior Member charlenemichaels's Avatar
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    Most embarrassing moment at the age of 10 i was trying my grandma's stockings on and left the bathroom door unlocked. She had them drying on a rack in the BR.

    The pleasure of her hose overwhelmed and i made that error of leaving the door unattended.

    She did not make a fuss just scolded me to left her things alone and get ready for dinner.

    She was babysitting at the time. Never said a word to my folks, thank goodness!

    Those stockings were silk and i never forgot the feeling!!

    ~Char
    "Little darling, the smiles are returning to the faces. Little darling, it feels like years since its been here. .... Here come the sun... - George Harrison "Here Comes the Sun"

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