Early Teenage Crossdressing Memories

[lynda]

Hi girls I started dressing very young with my mom stuff but I was lucky my mom caught me in her girdle she came home early from work and caught me she told me she didn't care about dressing up but not in her clothes so she took me to JCPenney's and pour me some my own clothes to where she said she was not going to tell my father cuz he wouldn't understand so every night when my father went to work it worked from 7 to 7 all night my mom will let me dress I just love my mom until the day she passed we were close friends I think she enjoyed having a little girl sometimes

[KelleyB]

By the time I was 12-13, when my sister and I visited my mother at her apartment (divorced parents, father got custody), I'd always do my utmost to stay home when they went out shopping or whatever.

It was during these times I explored my mother's half slips, bras, and a few dresses/skirts. I've just recently gotten back into wearing dresses/skirts along with bras, blouses, and half slips. My wife is just fine with it, as "they're just clothes". I was quite relieved, as she'd never seen me dressed to that degree until last year.

[Susan Thomas]

My experience is very similar to the other girls. I was about eleven or twelve and found myself attracted to my fifteen year old sister's one-piece swimsuit. After trying on the swimsuit, I progressed to her panties and bra. The trigger for my crossdressing might have been an incident that happened on our vacation, a month earlier. We were in Ontario, Canada at a cottage on a lake. I was playing with my cousins in the yard and then out of the blue, my aunt and uncle (for an unknown reason) held me down and put a bra on me. I still remember it was a white padded bra. My aunt took a picture of me wearing the bra. Years later, she sent me a copy of the picture. I really do look quite upset. I always wonder if I would have become a crossdresser if not for being forced to wear that bra. I suppose most boys would have just laughed it off, so maybe I had a feminine side that waiting to be awakend.

As far as my pre-teen crossdressing, it only lasted a few weeks. I was in my sister's bedroom, admiring my refection in the mirror. The red one-piece swimsuit just seemed so right and I felt so feminine. Unfortunately, I had lost track of time and my mom returned home way sooner that I was expecting. I was caught red-handed. She started yelling at me and asking me if I wanted to be a girl. Nothing else was said and I don't think that she told my dad or my sister. I must have been quite frightened, because I didn't again crossdress for ten years. I am still in the closet, but I have managed to have a happy marriage as well a nice career as a military and airline pilot.

[Sporco]

I remember playing "dress up" when I was 7 or 8. I'm not sure how it got started but dress up involved some of my mom's satin briefs in bright colors. At some point that stopped. I really didn't think much about it until just now.

Then when I was 12 I found a pair of girls forest green cable knit knee high socks. I had developed quite an interest in feminine socks so getting a chance to actually wear them had my heart racing.

Then at 14 I found a pair of black pantyhose at school and tried them on. The hook was fully set with this. I remember riding my bike to the pharmacy to buy pantyhose of my own after that and wore them under my pants to school pretty much all the time unless I had gym that day.

I've been dressing underneath ever since. I still love girly socks and hosiery, but also panties, lingerie and pretty much any other feminine clothing. I wish I looked better in it, but I still enjoy it.

[Vintage4sarah]

I was fascinated with my mother's nylons from an early age and that would extend to my sister and my other close relatives. The problem occurred that by 13 years old I was nearly 6' tall and my mom was 4'11" and my sister 5'3". Nothing really fit as I desired the opportunity to go beyond just wearing nylons.

At 14, I started to dog sit for neighbors who left on vacations. The moment would come when I starting sitting for neighbors where both the mom and her daughter were taller, especially the daughter. Everything lined up one day when I toke the leap and I was able to completely done their stuff from the girdle and bra to skirts, tops, nylons and shoes to fully become the image of a female. That first time viewing me in the mirror was electrifying. The next day, I snuck out of our house with a hair piece of my sister's. This time the image in the mirror was a true revelation of my potential. There was some guilt with this, but this only made me more cautious and looking for more opportunities.

More sitting jobs would follow until I left to attend university not to be relived until well into my mature years when it all fell in place once more.