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
My story is a little different. I started wearing my grandmother’s hats when I was two or three. Mostly everybody thought it was cute. Then I started putting on her shoes which were much too big. She was a businesswoman yeah, so she had a lot of dresses high heels lingerie and hats as well as of course all of the foundation is necessary. At one point I started wearing her camisoles as dresses. I think this is when they gently discouraged me. I have always hung out with girls and had female friends. I developed somewhat of an aversion… Read more »
Samantha, thank you for your story. You’re fortunate your wife allows you the freedom to cross dress. -Hugs, Marian
Thank you for your story Marian. I was around 4 years of age when I put on one of my sisters dresses. I hid in the closet so I was not seen. When I was about 6 or 7 I would play dress up with my sister and her friends. The girls always put Mom’s cloths on over there’s. I would take all mine off and put on mom’s. I loved the silky feel of mom’s panties against my skin. I mom always had a fit when she seen me wearing her cloths. In my teen years I would continue… Read more »
Dorothy. thank so much for your story and kind salutations. I too prefer garter belt and stockings over pantyhose; love the feel of the tension between the garter belt and the stockings on my upper thigh! But with a short skirt or dress, I do feel more comfortable with pantyhose, especially if I’m going out. -Hugs, Marian ❤
Wonderful story Marian.
I was never caught when wearing my mom’s bra or slips, but they did get me excited. I had no idea what was going on, being only 10. Didn’t know why my cock got hard, but I did know it felt REALLY good!!!!
Thanks for your reply Michele, I can relate to having no idea as to what was going on downstairs, it’s funny now but back then I remember thinking “what have I done, how do it get it back to normal"??? -Hugs, Marian ❤
I don’t remember my first time, but I am sure it was before I was 8. It was definitely before puberty since my first erection was some time later when putting on hose. I didn’t even know what an erection was. It was just a weird thrill to put on female clothes. Sex was still an unknown. Stockings were the most wonderous thing in the world. Staring at women’s or girls’ nylon clad legs quickly became my most favorite hobby. I would get a yeaning, a hunger to see them and to touch them, and of course to wear them.… Read more »
Diane, enjoyed your reply. Don’t you just miss women wearing nylon stockings? I prayed to God too, but like you, I’m still dressing (and believing in Him). -Hugs, Marian
Yes, I certainly miss women wearing stockings. What irritates me is the rich and famous walking down the red carpet wearing $1,000’s dresses, shoes, etc., yet they don’t bother covering their less than perfect legs with nylons. I don’t understand it. Is it a women’s lib kind of thing?
Most likely, it seems women lib types have branded some of their clothing and accessories as male preferences forced upon them so have liberated themselves from these items. It was almost comical how women overdressed for all occasions in the 1950’s and 60’s. Now the pendulum has swung to underdressing! They now are more casual and laid back in their appearance, similar to how men have traditionally been categorized. Or “what’s good for the goose is good for the gander" logic. Maybe men need to spruce up more to trigger a dress revival reaction by women! But at least us… Read more »
Men dressing up? Never happen.
Touche!
I started borrowing my Mom’s things around 12, and loved the feeling it gave me, and there definitely was some arousal involved. I was caught at it couple of times. My Mom was looking for a specific item of underwear and couldn’t find it, but it was in my room! She was very cool about it, and didn’t berate me at all. Then another time I was laying on my bed in one of my Mom’s slips, and I think I had dosed off and my Dad comes through and asks what are you wearing, then answers his own question!… Read more »
Amy, thank you for your informative and well written reply. Our stories are similar up until we got own places, I found the urge too great so off I went shopping! -Hugs, Marian
I can relate to your story,Marian. I began crossdressing when I was 11. Also experimenting with my Mom’s panties, bras, stockings,nighties and makeup. I nearly got caught once by my Mom, but was able to escape to the bathroom before she saw me. I’m sure she knew what I was doing because I left all of her makeup on her dressing table and probably left her lingerie drawer partly open. She never mentioned the event but years later she said that I would have made a wonderful daughter
HI Janine, thank you for your reply. Merry Christmas & Happy New Year!! -Hugs, Marian
similar to my life . I am the oldest of 5 boys and Mom always claimed we were each supposed to be twin girls. 1st I would take a bra and panty of my moms , then I would wear them at night . I slept so comfortly , one night my parents checked on me and found me wearing them. Next was counseling and promise to stop of which I could not. I progressed to taking underwear off local cloths lines as well as getting caught breaking into a house for items . I would use softballs for breast… Read more »
Thank you Georgia for your reply. Regarding 2 inch heels, wearing any size heel is a feminine experience, so enjoy them! If you’re shy about buying make-up and a wig in person, realize that you can order them on the internet. Even if the credit card is in your name, the store could assume it’s your wife doing the ordering and you doing the paying. -Hugs, Marian
Hi Marian. My story is similar. I started putting on my moms stuff around 7. To me the only thing wrong was that it was her stuff not that it was women’s clothing. My parents caught me numerous times. I was around 11, my parents left the house for awhile. I got all dressed up. Bra ( socks in them to make boobs) hose slip dress and lipstick. They came home early oops. They sat me down for “the talk”. I sat there like the little girl I was. Now this was the early 70s but I knew about trans… Read more »
Hi Abby,
I really liked your reply. We have had similar “Gotcha Moments", at least you had your lipstick and clothes on! (tehe) I actually visited the psychiatrist in my ordeal, he seemed more interested in the extent of my knowledge when answering his general test questions. He concluded I was within the “normal" range but to be aware of it impacting my future life.
If you want to chat again, let’s do it! Stay safe from Covid and Merry Christmas!
-Hugs, Marian
thank foryour story althoug never been caught or was my mother ask me once if I use mascara which to I denied but Irealy did not so I wonder if she ever knew and wonder why that question is always been so exilarating and my blood p goes to the sky sometimes wonder if is healthy to do it I am just silly sorry hug to you
Hi Lisette, So nice to hear from you! That exhilaration you feel is called the “Pink Fog" by cross dressers. Once in it, it’s near impossible to come out! So read up on it before getting serious because cross dressing is a life changing event! You need to control it (not very easy) and not let it control you. -Hugs, Marian
It is always comforting to read others recount their journey and see the many similarities. While the “initiating event" usually differs, the feelings and lifelong desires are the same. My start is among the different kinds. My best friend in early childhood was the girl who lived a couple houses down from me. She was two years older and two grades higher. Odd, irrelevant fact: she was the person who “took me to school" for my first day of kindergarten. Somewhere along the line, we started playing doctor. I was probably 6years old. We lived in a small town in… Read more »
Kimmie, thank you so much for your interesting reply. And your photo is of a very attractive woman! For me, after my wife’s passing in 2014, I have been dressing nearly every day and dress each night in a night gown, panties and bra. Just enjoy being dressed as a woman! -Hugs, Marian