No father in the picture, combined with mom dressing very attractively for work every day. At the age of 13/14 I was very depressed as other boys had developed into young men; puberty had started without any noticeable enlarging of my privates.
I was ridiculed in the school showers, this made me realize I was in for a difficult life, probably undate-able by the opposite gender (who would want this pathetic little d*ck). Debby Harry was my idol; I loved the overly blonde look. I used to look at her lovingly on my bedroom wall.
I started finding comfort in magazines where lingerie was involved, and became curious about feminizing myself. Maybe my little boy bits would fit nicely into girly panties as to loosely rattling around in those big y-fronts I have to wear.
Moms’ laundry hamper got filled Mon-Sat for the weekly Sunday wash, and was located in the upstairs bathroom which had a lock on the door for privacy. The first time I tried on panty hose (with her panties attached inside) I got so excited I had my first orgasm and was just shocked what happened with the mess I made.
I felt so horribly guilty and vowed never to do it again, however I fantasized about the experience all week and went back into the laundry hamper during my next bath time.I bathed 2-3 times a week, and bath times became extended as I started spending more time dressing in moms’ clothes than in the hot bath water.
I got familiar with handling moms 36A bra’s (always white. very little padding required), selecting the sexiest panties (my tiny boy bits nested in perfectly), hose (always brown), and her silky full white slips (my favorite part of dressing); sometimes I would be rewarded with a blouse as a bonus!
Her clothes had such an intimate sweet aroma of perfume and natural sweat, and of course I quickly learned my mom’s period cycle while combing through her panties (useful as she could be really sensitive and bitchy at times).
Getting caught cross dressing as a careless teenager? Oh Yes!
I accidentally laddered multiple sets of panty hose, fluid mishaps I couldn’t clean up, possible stretching of garments.
Mom couldn’t find the strength to ask me initially, she would give me digs such as if an effeminate man was on television, she might throw at me “I bet he wears his mom’s panties” or “I bet he’d like to wear my panty hose too”.
She also tricked me by sitting a new pair of black open crotch panties on top of the laundry pile one day, I couldn’t believe my luck – I should have realized it was a trap and I was being tested. I failed.
Mom greeted me outside the door after my bath and asked if I had found anything I liked. I went bright red as she stormed downstairs. She probably threw the panties away in disgust. We generally avoided each other for a week or so and then it just became a taboo subject, I reluctantly stopped wearing her clothes for a while.
By the time I was 16 I started sneaking into mom’s bedroom for access to her skirts and dresses; the first dress I ever zipped up (a simple gray number) I thought I was going to faint with bliss when I looked at myself in her bedroom mirror. This is when I knew my life direction had changed, and I felt wonderfully positive for the first time in many dark years.
Of course, the zipper got stuck! I remember panicking and sweating as I tried to wriggle out of it as the clock was ticking towards moms coming home time. I got out of the dress somehow without wrecking it or breaking the zip! I don’t think my heart has ever pounded so heavily in absolute panic. This experience did not stop me from modelling her entire wardrobe over time.
Next time getting caught was mom discovering my own secretly purchased black panty hose (nice change from brown!) hidden in an old sneaker under my bed. That night mom sat me down and asked me if I liked girls – my reply “yes, and there is a girl who i would love to date…but she doesn’t like me in that way” – that seemed to be good enough for her (phew he is not gay and going to hell!).
She must have thrown away my hose, and we never spoke of this uncovered secret again; she probably decided not to go snooping in my ever bedroom again in case she found something else. Yes I had many hidden garments around the bedroom (hidden in much better places!)
Looking back, it was very sad that we were both too embarrassed to open up and really talk it through. Difficult dark days for a difficult teen, with no one to confide in.
Suzi. x
Your story is not that different from my own, although my mom never caught me as far as I know. When I was a young teen I could fit perfectly into her form-fitting dresses, bras, panties, stockings, garter belt. I would put on lipstick, but didn’t have a wig. I would have loved to have the wigs I bought later in my cross dressing life! I was obsessed with hair, and still am. When my hair gets long enough I set it with brush rollers. I’m married, and my wife knows about my love for makeup, hair, etc. but she doesn’t support it. She’s okay though with me doing my thing when she’s not around, which I appreciate.
I started like you about age 12 by 53years old became a female permanent ly you and your mum should have been open with each other dressed as a girl full time since age 12 love the panties tights and heels skirt and tosand dresses everyday
Such a great experience and age.