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I was 17 and found a liking for wearing my sisters clothing, underwear to overwear. I must add the clothing being my sisters was irrelevant, it was purely the female aspect. One day I was in complete head to toe dress and decided to walk around the house when literally half my family came in and caught me stood in front of them in annaroused compromised position
Wow Kelly,
I am feeling the Embarrassment just reading this. What decade in our world did this happen ? If this happened to me in the 1960s I hate to think what would have happened. How was everything handled? I hope with as much Grace as Possible.
My brother was caught by mom and me several times like that. we finally let him wear the clothes he wanted so badly to wear. When he ask to change out of them we said no. Mom said he wanted to wear them so much that he could wear the everyday in our home.
I used to wear my mother’s things (no sisters) when I was a youth, we were about the same size in the latter years of middle school and early HS, until I grew in size. Both of my parents worked full time so I had plenty of opportunities to dress. Never got caught by family but one time my neighbor caught me when she came over to borrow something. She was my mom’s age and her good friend so I imagine she told my mom. Mom never mentioned it to me though. The neighbor just said I looked cute (I didn’t, she was just being nice), and my secret was safe with her. That was last she ever said anything about it.
I was dressing since I was 11. I know my sister and mom both saw mme numerous times. But never let me know. They understood what I was doing and always played off as they never saw anything. No father so I lived with all girls. I’m sure that started me off in this direction. I did get caught by my sister putting on mascara, she just walked into the bathroom without knoxking and there I was, leaning over the sink with the mascara brush in my hand. She didn’t tell anyone about that, she also helped me out with it, she said I put too much on. The next day i went to the bathroom and there was a new box of mascara next to my toothbrush and brush. She always covered for me and has never said anything about it to anyone. Only thing she said was don’t use my makeup please. I’m sure I was ruining it, being inexperienced using it. She later got me eyeliner and showed me how to use that too without looking like a raccoon. I was lucky I had her and also very happy she never ratted me out. Sorry to ramble on
I was at home on my own one day when I was about 12 and my mothers sister popped over for a drop in visit and I had a face of bad makeup on the full works, I tried to wipe it all of but it was still there, I told her I was doing a play and I Know she new I was not telling the truth, I am sure she told my mother but nothing was ever said to me,
OMG, I think many of us have had a similar experience of an unexpected caughtcha moment. I was 11 yrs old when my mom came home early and found her 1st born son was fully dressed head to toe as her 1st born daughter….lol…..I didn’t have any sisters so I “helped” myself to her clothing and heels. I couldn’t run and hide since I was only beginning to learn to walk in heels. All I could say through my utter embarrassment was that I just wanted to see what I would look like as a girl. She laughed, probably at how bad my make up was applied. As embarrassed as I was, in a strange way, rather than putting an end to my dressing, the desire only became stronger. Since she didn’t tell my father, in my little 11 yr old mind, I rationalized that I really wasn’t doing anything wrong. I actually began dressing as Liz for Halloween. My mother may not have approved of my xdressing, she kept it a secret so at least my story had a happy ending. It pays to have been the spoiled 1st born daughter.
See me from the age of 8 or 9 I started CDing, then for some reason I just stopped about middle school age. Then shorty after I turned 18 I meet a girl, and we liked each other. I told her about my younger years of crossdressing.
Well one day she gave me a gift box with some lingerie in it. Stuff like a few pairs of sexy satin panties, garter belt, stockings and some girly top.
She told me point-blank, and I quote “If you wear these I will (Blank) you!” I wore and never stopped wearing since then. That was well over 30 years ago.
Would I do it again? HELL YEAH I WOULD, and maybe not stop this time if I ever did it again.
That was one time, and Here is another time.
This is how some friends found out. I basically play it off as a gag, but they knew better. Friends always seem to know the truth, no how much BS you feed them.
It was New Year’s Eve 1999 and everyone was worried about the Y2K thing happening. That night I was not planing on going out, I was just wanted to drink alone, and I was already drinking at home when my buddies called me up.(Basically they wanted to try to get me out of my funk, make me go out and have some fun) They wanted if I wanted to go out drinking for a New Year’s Eve party and try to pick up women. By this time I already had enough in me to have a good buzz going.
Well I was more buzzed than I thought. Because I had this dress that I wanted to wear out like forever and the alcohol was telling me. Do it, do it you chicken (Blank). Do it! Well I did it and I showed up at the bar wearing a black maxi slip dress on. My buddies looked at me and said WTF are you wearing. I looked down to see what I was wearing(playing dumb and acting like I didn’t know I was wearing a dress), and I yelled out it. “It’s (blank) New Year’s Eve man and this is perfect for New Years.” My friend Mike said “Hey, Yeah, You lying sack of (Blank), but right what ever floats your boat” and they messed with me the whole night(They picked on me bad, real bad). I just played it off as a gag, it was too late to go back home. I started this mess I might as well live though what I created.
We party on, I was drinking steady, and I kept on wearing the dress(mainly, because I had nothing else to wear). About an hour later I was on the dancing floor, doing my own thing. A girl started dancing with me and I ended up hanging out with her throughout the night. We were really getting along so good, we traded phone numbers. All buddies stuck out and got no one. As for Me, I was the life of the party(at least in my own world I was).
That same girl I meet at the bar, and spent the night with. Well she ended being my girlfriend for most of the next year. I like to think, that my dress was my chick magnet, but what I really think is. That all the alcohol I drank gave me a false confidence. That killed my fear, gave me confidence and Women just like confidence in men, even though it was alcohol induced.
This is the time between my first wife leaving me, and before I met my second wife. I was not totally out yet, but this was a stepping stone to full-blown openness to the world.
And again I would do it again. It is just who in the hell I am.
Hippie
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My Mom caught me dressed in some of her clothes. She asked me about doing that and I told her that her clothes were just so beautiful that I wanted to wear pretty things. She didn’t get mad or upset. She was understanding and gave me a few of her older things to play dress up. I so enjoyed those times. When I got older and got a summer job I gave her some of my money to buy me a few pairs of nylon panties that fit and a skirt with blouse that I had seen in the local department store. She bought them and gave them to me with the understanding that I could not wear them out. She explained how some people would be mean and could try and hurt me if I did go out dressed. She always knew that I had a very feminine heart.
Sandy
Sandy
What a wonderful response from your mother. Warms my heart to hear loving parental response.
Caroline
I had been wearing my sister’s and Mothers clothes for a few years, I am sure I was stretching out their clothes. One day my mother confronted me about wearing their clothes and I denied it. It was so ridiculous that I would deny that I was wearing their clothes because it is obvious that I was wearing their clothes. Looking back I wish that I admitted to it.
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Even though I was never caught by my parents I did try to come out to mey mom at age 9. I told her I wanted to be a girl when I grew up. In a VERY mortified fashion she said we would talk about it tomorrow. Well tomorrow never came and I figured out what I wanted was “wrong” and it was not discussed again until I was around 28 and showed her a picture of Carolyne. She didn’t speak to me the rest of the evening and went to a counselor who said it wasn’t her fault and I was sick and needed help. My father was a career regular special forces officer so I learned early to hide everything from everyone. It took many decades to become accepting and comfortable with who and what I am and I accept I am transgender, although I can never transition, and my cross dressing is my outlet and allows me the freedom to express who I am. To those whose family knows and supports them or accept them you are lucky and should thank them for their love. For the rest of us, personal acceptance and acknowledgment that what we are and do is NOT wrong is our greatest accomplishment.
🍷C
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