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
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.
Thank you Kitty for replying. Yes, I went up the “dress up" ladder pretty quickly. I would add new articles every time I dressed until I eventually achieved a complete head to toe transformation. I was mesmerized by the image looking back at me from the mirror! I didn’t really have a fetish for any particular item (heels and lipstick came the closest), I just wanted to wear everything ASAP and see my feminine alter ego appear, Thus, Marian was created! -Hugs, Marian
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That is so great, What a vision and determination!!!
Kitty, thank you again! -Hugs, Marian
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
Josline, well said! Thank you for feedback. -Hugs, Marian
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… Read more »
Roxanne, so pleased you have gained some peace of mind after reading my article and expressing yourself so eloquently! Every crossdresser goes through shame and guilt, so welcome to the club. What you must realize is that the desire to cross dress is apart of your physical self; it won’t go away and needs some attention to starve off depression. Accepting your female half will bring balance into your life. Balance between your male and female halves will relieve anxiety and help reduce shame and guilt. If you were to consider crossdressing as a neutral activity (i.e. neither good or… Read more »
Oh Thank you so much for the reply. As I said to Tara, when one opens up it is sooo comforting to find someone on the other side that gives such supportive words. Locally we have a group where I found a friend Joolleen, who I found is also on CDH, to share with – in the last 47 years that is travelling the same path and we are exploring together without judgement! Such a release!!!
Thank you again and all the other ladies that read and support myself and others!!!
Kind Regards
Roxanne.
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.
Alina, thank you for responding. -Hugs, Marian
Thank you, it was a pleasure to respond
Fortunately I’ve never been caught by my parents. I hope nothing bad happens if/when they discover my inner girl.
xoxo
Daisy
Hi Daisy Marie, thank you for replying; good luck if/when telling your parents -if you’re sincere when dealing with them, they may be more understanding. -Hugs, Marian
I wasn’t caught by mom or dad but my sister. Although I had not started wearing her clothes I was very fascinated by her nylon panties and nightgowns and was probably close to trying them on, I was holding up one of her nightgowns I found in the hamper when she walked in on me. I was very imbarned to say the least and was ready to be yelled at. But instead she smiled and said it was ok, she said lots of boys like grills silky things and had me put it back into the hamper then asked if… Read more »
Hi Sarasue, thank you for replying and for your story… you are very fortunate to have such an understanding family and friends! -Hugs, Marian
Rather to be raised by such understanding people. I wish I had had some support even if it was in the background. I think my mother figureed out I cross-dressed. She was taking care of my house one time well I was gone for a few days and a package came from Jessica London. She’s nosy so she opened it up and found a pink size 22 leather skirt. She quizzed me about it and I just played dumb. Lately I have wondered what her reaction would have been had I just looked at her and said it’s for me.… Read more »
While never caught dressed, my stash was found a couple of time by my mother. I always tried to find some excuse which did not include me dressing in women’s clothing. My parents, while loving, were not tolerant of what they believed to be deviant behavior. My Inquisition from my mother and father as to the reason I had a box of panties and other feminine items led to many unbelievable denials on my part. I never broke the cross examination and thus remained in the quasi closet even though I knew my parents always thought differently of me.
Jenna, thank you for responding and telling of your experience of nearly (maybe?) getting caught by your parents… know how tough a subject this is to broach with parents. -Hugs, Marian
I got caught by my mother when she found my “stash" between the mattress and box spring of my bed. She laundered, folded and placed the items on my bed and never said a word.
Wow, you’re were fortunate to have such a sympathetic mom. -Hugs, Marian
Thanks
I can relate to your experience. I have always felt concern/fear/trepidation at others finding me out. To answer your questions: Were you ever caught cross dressing as a child or young man by one of your parents and if you did, what happened? My sisters used to use me as a dress dummy when I was little – they said they needed me to model dresses for them, so that they could hem the dress. Even from the first time it happened, I was required to wear girls panties underneath because “boys underwear makes a dress hang funny" After the… Read more »
Robyn, thank you for your interesting reply! I can likewise relate to your experience although I had no sisters… but my upbringing said “boys who wore girls clothes were freaks and abominations" which took a long time for me to overcome the guilt and shame -Hugs, Marian ❤.
I totally get you Marian.
I had the same experience from my parents and grand parents growing up. I don’t know if I was ever caught – because a lot of my early years have gone missing in my brain, thanks to too many concussions.
I don’t know if I ever did get over the guilt of it, but the shame… I don’t care now who knows.
Robyn,
I laughed at your reference to not knowing if you were ever caught “thanks to too many concussions"! Hopefully the concussions were due to sports and not serious accidents!
I know guilt is tough to overcome, but with time and especially the realization that “she" is part of your Self-being, however, should make it go away as it did for me. The realization part is the key! -Marian
Hi Marian, I started out much the same as you except I was 12. I would dress in my mother’s panties and pantyhose, bras and heels, keeping a stash in the linen closet among the towels and sheets. I was never “caught" while dressed, however my stash was inevitably discovered. Like you, in retrospect I sometimes wish I had disclosed more about my need to dress, but in my own defence, I was very confused about it all myself. I disclosed to my first wife, who reacted very much the same as your mother did….."don’t ever put on anything belonging… Read more »
Thanks Rikki for your interesting reply, seems many of us started out with Mom’s clothes. I didn’t have a stash until I got married: I always returned my Mom’s clothes because I felt she had a good awareness of the number of her undies. My late wife was tolerant to a degree but did not like to see me fully dressed, especially with a wig. She said it made me not “me" in her eyes… which, interestingly, always had the opposite affect on me since it affirmed I was making a realistic transformation. Since we agreed to be friends via… Read more »