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
More Articles by Marian Andersen
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Marian Andersen
Latest posts by Marian Andersen (see all)
- Caught Cross Dressing By Dad! - December 18, 2020
- My Best Experience Crossdressed - November 20, 2020
I dont recal i was two young, but my sister would make me dress as Laura Ingalls and run in the tall grass and fall just like the tv show. If I wanted to play with them this was what she said she made me do. Well I never went in moms things maybe looked at them but that was a line I couldn’t cross… Now my sisters on the other hand she had her swim suits in the hall closet. I would take them but not put them back.. Nasty imo if I did. i would then put them under… Read more »
Thank you for your reply and interesting story! Seems you have had some pretty accepting people in your life, which is always helpful. -Hugs, Marian
hey marian. just wanted to answer one of your questions from a post i read from you. it did and still gets me very aroused to wear lingerie and my wife loves watching me. just to let you know i’m still kina of new to all of this. but its so fun.
Thanks for your reply Mike. Happy to see your wife enjoys participating; you are very fortunate! Also, you will realize that her awareness will greatly reduce the feeling of shame and deceit that often accompanies cross dressing. Keep the communication open with her and most importantly, keep any boundaries she may require as this will keep your mind at peace. Balance of crossdressing with your regular life is the key to maintaining this peace of mind (and marriage) throughout your life! -Hugs, Marian
I am a newbi as well and still get aroused while in lingerie, wife likes to see me subtley excited and it so fun
I came very close to being caught by my mother wearing my sister’s hose and heels. I heard her coming up the stairs and clomped across the hall to my room, losing a heel in the process. Still wearing the hose, I sat on the edge of my bed with my legs tucked under it. She entered my room, gave me a questioning look, and turned and walked out. She never mentioned it again, but I’m sure she knew what I had been up to.
Monique, your heart must have been in throat when your mother came upstairs and into your room! Have you wished she saw you dressed and questioned you about your crossdressing? I did afterwards, I hoped I would have been forced to cross-dress after school for at least a week – didn’t happen!
Thanks for commenting girl! -Marian
It probably wouldn’t have been a pleasant conversation, although several years later she did help me dress for a Halloween event.
I probably first started crossdressing about 12 or so I think. I had a sister 10 years older than me . I never thought about wearing my mothers clothes , that was old fart stuff to me , but my sister had the sexier panties and bra’s that originally sparked my curiosity. I was one of 6 children so there was not enough privacy or time to get too deep into dressing but I would occasionally try on lipstick to see what It looked and felt like , then quickly wipe it off. This was the late 70’s and we… Read more »
Wow, Natalie! Pent up frustration can be quite forceful as you witnessed. At least, after calming down she was apologetic and concerned for your state of mind. Definitely, take comfort in that! My Mom was more confused and dumbfounded but she was quite emphatic about my not using her clothes again! But, that lasted only a few months before I started using them again. But I know I didn’t want to experience her response if I was caught again!
Marian
I wasn’t caught dressed (or rather, undressed, as you were), but my mum found part of my stash of women’s clothes, makeup etc. and you can imagine the horror when I went to get dressed, only to find that it wasn’t there! I searched the house and finally found it behind mum’s chair in the living room. She had obviously hidden it there to confront me, which, eventually, she did. It turns out her main issue was that I’d been outside wearing the clothes! The answer was no, as I’ve never felt comfortable enough to venture outside, There was also… Read more »
Hi Gloria, thanks for your story. Well, that must have been a great relief for you when your Mom only needed assurances on two issues to return your stash of female items. And, you got a supportive sister as a result of your Mom’s discovery – I’d say you made out quite well following your Mom’s intervention. Also, thank you for your friendship request which I accepted. .I look forward to messaging with you.
Marian
Hello,
I was fascinated with a white lace trimmed half slip my Mom had. Once she caught me I had the spanking of my life.
That was the start of my arousal, and my dressing grew from there. I’d play sick to stay home and go through my Moms and sisters lingerie and pantyhose.
The only guilt I had was that I couldn’t be who I wanted to be when they were alive.
Jennifer
Jennifer, thank you so much for your reply. I know how you feel; wishing that they were able to know the “real" or the “other" you and that at you’re at peace with being that person.
Marian .