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Like most boys, I started cross-dressing by wearing my mom’s panties and nylon stockings. Doing so was both erotic and enjoyable, but being a pre-puberty 8 year old child, I was not sure of the reasons why. Eventually, with puberty, came the desire to wear my quintessential items of womanhood: bras and lipstick! Although strongly drawn to these two items, I was overtaken by fear. Fear that I may reach a point of no return and become a sissy (i.e. a boy dressing in girl’s clothes without any sexual reference applied). It was an embarrassment, what would my family and friends now think of me? Thus, my “secret” was born and it would be kept for another 6 years, during which, I resolutely expanded into mom’s remaining trappings: dresses, skirts, blouses, heels, jewelry, additional lingerie and makeup. I still felt guilty about my “secret” (and the arousal it caused) but I enjoyed even more my womanly transformation and seeing her reflection in the mirror. However, an unexpected day of reckoning was fast approaching.
I was 15 years old when one afternoon my dad left to watch a bowling tournament my mom was participating in. Great! Several hours alone, more than enough time to watch television and relax while dressed as a woman. However, I forgot to lock the door and as I headed to the bathroom to put on my makeup, my dad unexpectedly returned home for a forgotten item. He was gone long enough for me to put on my mom’s bra, panties, garter belt, nylons and heels. When he came in his draw dropped. I ran to the bathroom in my heels and locked its door. I was caught! Eventually, my dad came to the door and asked me to come out. I said “no, you saw me, I can’t come out!” About 15 minutes later I came out with only a towel on. We talked, and he said “I’ll need to tell your mom about this when she comes home”. I pleaded with him not to, but to no avail. I was told to get dressed and go with him to see my mom’s tournament. No more being left alone to cross-dress. After what seemed to be forever, we arrived home. When dad told mom, the s—t hit the fan as she told me to never get into her things again or else…! Next day we talked about it and she asked if I liked dressing up? I said “no, and I wouldn’t do it again”. Sadly, I wish I could have said “yes” and maybe been able to dress up after school and be my parent’s pretend daughter helping with meals, washing dishes and cleaning the house.
After several months, I began to again dress secretly in mom’s things. I’m sure she noticed that her bureau draws and closet items were not quite as she left them, but she never mentioned it. I would continue to dream of being a sometimes female for another ten years. Then following graduate school, I got my own place and with my initial paycheck, I splurged and purchased the latest female fashions thereby creating my own hoard of feminine garments, heels, makeup, and a first wig. It was thrilling and surreal; I could dress as a woman on demand! Something I had dreamed about since childhood. Thus, after work, I dressed up and became the lady of the house. On occasion, I would wait for dark to journey out for either a walk or a drive. These nightly excursions were both terrifying and exhilarating as I sometimes got cat calls or whistles, but that’s another story!
Thanks for taking the time to read my article. Now please take a little extra time to either leave a response to my article or provide an answer to one or more questions I've posed to you below:
- Were you ever caught cross dressing as a child or young man by one of your parents and if you did, what happened?
- When you first started cross dressing as a young boy, was there a sexual arousal associated with your cross dressing?
- Was there guilt and shame associated with your early years of cross dressing?
Thanks so very much girls and I look so forward to reading your responses!
Sincerely, Marian
Yes there was sexual arousal associated with cross dressing, along with guilt and shame.I thought I was the only cross dresser in the world.
I was caught by my mother when I was a senior in high school.They sent me to a psychiatrist. They wanted me “cured”. After a while I told them I was “cured”. After that, I didn’t dress for a while. Then I was very careful not to get caught. As soon as I graduated college, and got a job, I got my own apartment. I was free to buy and wear my own clothes whenever I wanted.
Great story Marian! To answer your questions:
1) I was caught at about age 8 or 9 when I put on lipstick during the night and after freaking out, I wiped it off on the sleeve of my pajamas! Of course, when my mom found the top in the laundry, she told my father and they sat me down after school next day. I got the standard, "boys don't do things like that!" and made me promise not to do it again;
2) Of course crossdressing caused sexual excitement;
and 3) Guilt and shame were part of it for many, many years; with cycles of purging and self-loathing.
The good news is 14 months ago, I told my wife of 20 years about me and she has been my biggest cheerleader and mentor!
Thanks for a wonderful story!
A well-written description of your CD journey, Marian, and so typical of most our stories. The guilt, the shame, the stress, mom & dad's reaction or lack of, the eventual spouse and the part she plays, etc. Almost always the parents "catch" us. Later, if we did not inform her from the beginning, our spouse, in all likelihood, will eventually "catch" us, all so typical, the classic CD story. Job stress and substance abuse, psychological counseling, the list goes on and on...
Thank God many of us do eventually find peace. The peace that comes with knowing who we are and for those of us who seek it, the spiritual peace with our Creator.
I feel an obligation to support those who are still on their journey seeking peace.
Thanks for sharing your story. I never got caught because I didn’t wear my mom’s things often. I can still remember each time I ever did though. I don’t recall being aroused by it because I was so young when I did. But by the time I started underdressing in my 30’s, there was definitely arousal at first. That quickly faded as I underdressed 24/7 and it just felt normal to me. I never felt ashamed except for one experience. I was in my tween years and was spending the night at a friend’s house. His mom cut the legs off some old hose and have them to us to use as masks to play bank robbers (or something along that route). I decided to put mine on one leg and proceeded to do a half man/half woman routine like I had seen on some old cartoons like when one profile was female and the other profile a male. She was reading a book and just ignored the whole thing. Looking back, my embarrassment was more about the silliness of my routine than the actual wearing of the hose. I imagine that I probably would have experienced guilt and shame if my parents ever found out about me trying my mom’s things because they were ultra conservative and would have come down pretty hard on me.
Thanks for sharing. In order asked: No I did not ever get caught. I was around 12 when I first started so yes it was very arousing sexually. As to guilt,very much so. I remember those early dress up sessions usually ended with climax and right after that happened I couldn't get out of the clothes fast enough.
Luckily I got over the guilt but also luckily it still can be arousing even though I'll be 72 next month.
Hi Marian, I can sympathize with you I've been dressing since I was 10. When I was about 14 I figured since I crossdressed I must be gay so I started experimenting with boys. I had a boyfriend and my parents were at work. He came over and we were fooling around. I was wearing stockings, heels, garters, and bra and I was on my knees in front of him. Mom came home early and came in through the garage door into the recroom and there I was.
She didn't say a word just went upstairs. My boyfriend left, quickly and I got changed and went upstairs. Mom was really cool about it, she said she knew I was up to something, you couldn't get nothing by Mom and it didn't matter, I was her child and her love came without question. All she advised was don't let my Dad find out, he spent 6 years in the British army and really wouldn't have been pleased.
Thankful many times for Mom. She left us a couple of years back now and I really miss her, especially this time of year.
I too 'borrowed' mom's clothes, shoes, lingerie, hose, etc., and I left a box of pantyhose out on the table next to the front door. Mom and Dad came home and I got up to unlock the door and they had their key in the lock before I could get there. I saw the box, grabbed it and dropped it behind the piano. They really didn't say much as I found out much later in life when I came out to my mother 3 years after dad died. She told me that dad was a closet CD. Both myself and mom were both surprised that day of discovery. She did say that 'now a lot of things make sense'. I'm sure I didn't always put her things back exactly as they were in her dresser. Anyway, mom supported my dressing up until the day she passed (I sure miss her).
i was caught dressed up also but by my grandfather where i was wearing my grandmothers dress and nylons and wig, shooting pool in basement where there was no one else home, my grandfather came down stairs to see how i was doing i did not hear him come down. i was caught he did not say much but to make sure i put all her things back in the same spot, but i guess i did not for my grandmother left a note by her dresser, it said to stay out of her dresser drawer, she never talked about it. my x dressing went away for a few years and i started back up with my Gf dress and she never knew. we got married later in 83. that was it i was hooked i could not resist dressing up again so i got dressed up one year and took a pic of me and forgot to put it away,, my daughter seen it and showed mom, daughter said its his body not hers. so my wife knows now. she is OK with me dressing up but will not help or see me even thou she has seen me dressing up and dressed up. but she still will not let me sit in same room as her and talk like 2 woman. she does let me dress up and tells me i can do what i like to do. that's the hint that i can dress up meaning no one is home. still have a 23 year old still at home. i now have my own collection of dresses, nylons, bra's panties, and i even buy my own pads, make up, perfume, ear rings, necklace, heels , wig, nail polish, i even took over my wife's dresses for she does not fit into them.
Thanks for sharing your story, Marian. It’s too bad that you got caught, your Dad had no acceptance in his heart, and then he told your Mom. It’s a good thing that you got your own place in time, had your own privacy and continued the thrill of cross-dressing.
Rather than take the risk of being “caught” by my Father that I live with, I decided to gather the courage on Halloween night this year, dress up as a woman, and reveal that I’m a CD. He had acceptance in his heart, and it went very smoothly. I’m very fortunate. I wish you the best, sister!
Sincerely, Revel
Never caught growing up, but definite sexual arousal when dressed. In my teens I felt some shame and confusion, but also knew deep down that I liked men and other boys. The dressing was a big part of that, I thought it would make me more desirable to other men.
Wow, that's a really bold beginning....Straight into underwear and tights!!! I began with a gorgeous little gold pair of heels (meant for my sister!) ..But hey-ho!
I was never 'caught' I really didn't open up until I moved out and left home and began 'adult life' on my own.
There's never been guilt, but certainly experienced confusion. More so trying to identify as a boy. That was always weird. Uncomfortable.
Hi , Reading your story is a typical to all of us who passed thru this experience and enjoyed every moment ,,,yet getting caught is part of our dangerous life experience but the thrill of trying not to be caught is a pleasure indeed
Hi Marian
For me it started at 4 years old in a satin feel pixie outfit my sister wore to a school play...
Not sure why but my mother told everyone during pregnancy that I would be a girl... maybe it penetrated!
After the pixie event and as the years went by it was my sister's panties stockings and bra.
My mother caught me with the panties... promises were made but not kept!
Just went into stealth mode... then came the cross dress group meetings in the wrong groups - no support.
So back to stealth mode for years and years. Almost caught by a guy that insistantly wanted to give me a lift home in his car... didn't think I would get to mine!!
So I declined repeatedly...
Another close call amongst others while walking the streets at night (stealth - not pick-up!) I turned the corner and a whole group of guys were by their car with beers... I retreated with speed and disappeared into an unknown garden. They drove past a few times looking for me and then left - a close call of note! This followed by opening up to my bio girlfriend that did not want any secrets between us - my Gay experience did not go down well!!
So now I have gone full circle and the only happiness is when I am in stealth mode again...
This time though I have recently found two groups for support - this one and another local one that will allow me to express my inner truth?
This is the first time I have written about my experiences and it has given me unbelievable peace!!
Thank you to those that read this and will not judge me.
Roxie.
There first time, no sexual feelings, just wanted to see what I looked like and feel the difference. I liked it and did it again and again. I t got sexual about 13, then it become my undressing a girl.nthank you.