Strange things you might do when you're a young crossdresser

[Kitty]

I've never told this to anyone else before. I think it's weird. But when you're a young crossdresser and you can't get your hands on any female clothes to wear you get a bit desperate.

One time when I was 19, I went to stay at my sister's who was living with her husband in Derbyshire, UK. I had been without wearing any female clothes for quite some time (about six months) and I was getting frustrated. Anyway my sister always had the best clothes in my view. She's eight years older so her clothes were proper women's clothes and she's my height and even my size back then.

I remember turning up at her door and she was dressed in a wonderful black pencil skirt, white blouse, and black heels. I couldn't concentrate on the conversation. I just wanted to wear her clothes. ODD, when's it's your sister!

Anyway to cut a long story short during the night I got up, went downstairs to where the laundry was and she had clean clothes folded in the kitchen.

I so wanted to put everything on I saw (skirt, panties, tights, top) but I resisted. Imagine if I had been caught. Just too horrific. So I contemplated it for a while then went back upstairs to bed.

Thank God.

[Lacey Hadley]

Maybe not so strange but out of the norm for most of us genetic males especially as we enter puberty.

For me the years of infatuation of girls and wanting to wear their clothes etc. began from of age 5-6. By age 12 or so I was old enough to be left at home alone at times. I began my foray into my mother's clothes firstly her pantyhose. It felt so good and taboo to slip them on. As time past I began trying on her shoes, I could still fit into them back then I'd dress in pantyhose and her shoes and parade around looking at myself in mirrors and being a girl in my mind. By about age 14 I would do what I knew was a wrong thing and I'd take and keep a pair of her pantyhose, figuring she'd not notice one pair missing from her lot. I'd sleep in them and hide them in a bag of things I had until I put them on again. I'd when home alone from time to time put on a skirt or dress too

We had a pet dog at the time and on school mornings I'd get up keep on these pantyhose and dress up in my male clothes to take the dog out for a morning walk. My mom had a pair of white leather spike heel slip on 'mules'in the shoe rack. I'd grab them and take with me as I walked our dog. We lived in a semi-rural area and I could go among trees off a path way and take my pants off in all my sexy pantyhose clad legs and step into these shoes and felt so excited, outside in the cool morning air and being girly. Yes, as a teen I'd often masturbate too. pretending to be a cute teenage school girl with teen hormones flowing. I'd often wish I'd get seen and caught by most often school girls, but it was too early in the morning to have any walking by to school, but it turned me on as a 14 odd year old boy.

At this age I did not understand really why I felt a need to crossdress, but meh I felt I had to do it to keep me from being frustrated as a hormone induced teen boy.

[Kitty]

Thanks for your thoughts and memories. We are all alike! In most ways.

Yes I used masturbation too in my teens and 20s but not now. I don't get the sexual thrill I used to, but I do get another thrill. A buzz. A high.

I've been dressing every day for the last four days. Everything, make up as well. I love slapping it all on.

I've also been walking in stilettos over the past two days because I wanted to feel extra feminine!

[Emily]

But when you're a young crossdresser and you can't get your hands on any female clothes to wear you get a bit desperate.

THAT is most definitely an understatement. Sometimes, that desperation is just so overwhelming, how do you cope? What do you do? I know I've done things I'm not proud of just to be able to enjoy the feeling of wearing women's clothes... but what's done is done. When you're young and just starting to discover this side of you...

I would imagine that for most of us, it was a long, lonely journey. I have felt shame. I have felt guilt. But thanks to the friends I've made on this board, I've come to realize that I wasn't alone, and that I shouldn't feel shame or guilt. Feels good to have a place to talk about these things. It really does help... A LOT!

BTW, Kitty - back to your original post... that was probably your better judgement at work there. I can't even begin to imagine being caught in that kind of a situation - resisting the urge sounds like it was the right choice to make.

[Eileen (SO)]

Some emotions are difficult to drag out of an embarrassed spouse. My husband says that early cross dressing involved self pleasuring and thought that's why he did it, not a desire to be feminine. Despite playing with Mommy's clothes as young as 8, he thought of dressing as sexual first. At least until wanting to look like a girl became the primary goal.

When we married, both of us at age 23, is that young enough to qualify for this topic? Getting my head around the fact that my husband was a CD was hard enough, till I realized that he had 'borrowed' some of my things. We are close in size, clothing is one thing, but my bras! That is too personal.
Now, 'she' has all her own things. The only items we share are earrings and nail polish.

Eileen

[Requal Jo]

I too shared and wore my sisters cloths. They had some beautiful dresses, skirts and tops. The bras fitted well as we were all near to the same size. Panties and stockings came later in life. I loved the suspender belts and stockings.

[Deanna]

My first round of exploring cross dressing came when my girlfriend moved out of my first apartment. I wore all types of outfits in the hallways of the four story building from dresses to just lingerie. How I never got caught is beyond me. It was more sexual then I think, but it's all about an inner feeling now and I find that I may be less daring, but now I concentrate more on details, feelings, and becoming passable with body language, walking, stature, accessories, etc.

[DonnaT]

I would wear my mom's things, as she was 5'2" and most would fit for a spell. I had no sisters.

However, I wasn't always satisfied with her things, and desiring to wear more clothes more relateable to my age, I would sneak clothes off a clothes line while walking my morning paper route and wear it to the end of town and back, then return it to the line. Usually a full slip.