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

 

 

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Gail Rich
Member
6 months ago

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… Read more »

Kathryn Lynn Peters
Active Member
6 months ago

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,… Read more »

Peggy Sue Williams
Duchess
Noble Member
6 months ago

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… Read more »

Mika Malone
Duchess
Active Member
6 months ago

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… Read more »

Mika Malone
Duchess
Active Member
6 months ago

Yeah, I am extremely lucky to not have had the negative emotions. It’s really been an eye opener being here and reading about other girls that have had to deal with it. My heart goes out to them and I always wish that I can comfort all of them and help them.

Celeste Starre
Active Member
6 months ago

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.

Heather Jameson
Duchess
Active Member
6 months ago

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… Read more »

Alexis West
Alexis West
6 months ago

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… Read more »

Lucinda Hawkns
Active Member
6 months ago

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… Read more »

Revel
Active Member
6 months ago

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.… Read more »

Revel
Active Member
6 months ago

Thank you Marian for the kind compliment regarding my name.   Actually my Daddy is very elderly, and VERY old school. He’s one of the few in this day and age that doesn’t own a cell phone or computer! I do all the technical stuff for him. I also do a lot of research on the CD and TG community and helped him with the truth. Crossdressers are very misunderstood people, but he and I realize that CDs are very kind and beautiful people. Cross-dressing doesn’t hurt anyone, but judgment can hurt deeply. So yes, you are correct. I’m… Read more »

Jenny Thigh High
Active Member
6 months ago

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.

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