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My Journey into Crossdressing

My Journey into CrossdressingMy interest in female clothing began at an early age, I don’t know where it came from or why it is so powerful. I started with a pair of my mother’s pantyhose, from the moment I put them on for the first time, the bug had a hold on me.

From then on I would put them on every chance I got, that got to the point where, that was not enough, I started taking huge risks on getting caught but I didn’t care. The next thing I knew, I was putting on my older sister’s panties & bra along with the hose, it seemed that every couple of months I had to add more clothing.



By the age of 13, I was dressing completely & starting to experiment with makeup & hair, by the age of 14, I was sneaking out of the house at night completely dressed as a girl. That lasted until I was 17 years old, that’s when I learned about shaving my body & wearing nail polish on my fingers & toes, I let my hair grow out & I was taking some of my mother’s supplements to help grow my nails.

At 19 years old I met my ex wife, I thought that would be the answer to my dressing up boy, was I ever wrong, having all of my wife’s clothes, shoes, makeup & nail polishes at my disposal, I just withdrew from everyone & stayed home & dressed up.



My wife hated my dressing up & because of that, that is how I found out about plucking ones eyebrows & having your ears pierced, my wife would threaten to tell all of our family & friends about my dressing up if I didn’t stop doing it well, one time I told her to make me up as a woman then go ahead & tell everyone that I want to be a woman, so she did.

She double pierced my ears & plucked my eyebrows into really thin, highly arched lines, when she was all done with my makeover, I looked in a mirror then told her I loved how she made me look & I asked her if she would take me to a beauty salon to get my hair cut, colored & styled, she gave me a resounding no.



She did, however bring a number of her co workers by the house to meet her sissy husband who wanted to be a woman, soon after that she left me. With her gone I began dating men & I found that I loved being with men, I never had a shortage of s*x. I know that I will never stop dressing as a woman, I couldn’t even if I wanted to so I just embrace it & be who I was meant to be.

Submitted by Joanne Watters

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  1. Joanne,

    My crossdressing story is very similar to yours! I started dressing at 5. I remember finding my sister’s clothes in the laundry and wearing them and I knew that’s what I preferred. My grandmother and my mother let me paint my nails, wear lipstick and blush and perfume. When I was 8 my mother was starting to wonder a bit about me because I really wanted to wear girls clothes all the time and I think she thought she might ‘cure’ me by dressing me up fully and making me play with my sister and her friends. Obviously I was tickled pink and so excited to be ‘one of the girls’!

    I kept dressing up and about that time I was also getting sexually aroused when I dressed but I didn’t tell anyone. I wasn’t interested in the girls that way but I know my rock hard erections felt strange but good. I kept dressing this way until I was about 13 but I was getting tired of little girl and adolescent girls clothes and I wanted to dress like a big girl.

    I was visiting my cousins and I was playing and I noticed a few pairs of my aunt’s pantyhose hanging to dry in the spare room so I made a mental note of this and when I could finally sneak in I did and took a pair. I took those because she was petite and I figured they would fit me best. I had them in my pocket and then got worried that they might get damaged so I snuck into the bathroom to put them on. I was amazed by the feeling and obviously my penis agreed because I had an erection that wouldn’t go away!

    When we got home later I took them off and put them in my drawer. The next time I dressed I wore them and my mother said it had to stop and I couldn’t go out dressed like that because people wouldn’t understand and frankly she didn’t understand either. I secretly wanted to show my friend down the street because I wanted to know if he thought I looked sexy in them.

    I finally did go out dressed sexy on Halloween in 1974 and I had a great time. Not all the guys wanted to be around me but there were a few that came around meet when I was by myself asking me a lot of questions. Later on I started getting brave and I said to one of the boys that I was horny and he just looked at me and I thought “uh-oh, I’m in trouble” but he told me he was excited and glad I said something. We’re just looked at each other kind of stupidly and then I got a lot closer and took one of his hands and brought it down to the back of my pantyhose covered thigh, he started shaking, I was shaking and then he slid his hand up to my butt. He pulled me tight, we ground against each other and then I felt his penis against mine and we decided to make out. We found a bedroom and both started kissing and petting. We both felt each other’s penis and we gave each other a hand job. We both came, it was the first time I ever came and it was amazing!

    I dated a few boys in high school, mostly with me dressed as a woman. I dated a fair number of men until the early 80s until I got scared because of AIDS. I ended up going with a woman, it was different. I knew women didn’t have a penis but I didn’t exactly know what was down there. I told her I’d never been with a woman before, didn’t tell her about the boys and men but just said I didn’t know what to do. She got on top and sat down on me with her crotch against mine and played with me and I did get hard, she lifted a little and sort of sucked me in with her vulva and vagina. It felt good and I eventually came but it wasn’t anything amazing. We went through 30 years of marriage, maybe had sex 25 times, didn’t really get excited about it and about 15 years into our marriage I started dressing up and seeing men again it kept me sane.

    In the end we divorced when I left my email logged in on her computer and found out about my boyfriend and that I was ‘his special girl’. It was a bad day but now I’m finally happy. I wish you the best, I know you’ll be happy

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