How I became a Crossdresser (long read)
For as long as I can remember, I've always been "intrigued" by women's clothing. I would wear my sister's clothes, and I once stole one of my mom's nightgown's out of the laundry and wore that to bed every night. I had no idea that others did this. We're talking mid 70's, no internet, small midwest town full of farmers. The entire world I lived in told me how gross it was to be gay and men in dresses were perverts. This was something I had to keep hidden and couldn't tell to anyone. I grew up thinking I was the only one in the world that was "gross and perverted". I legit thought there was something wrong with me and I couldn't tell anyone so that I could be fixed. I had to hide this my entire childhood!
I tried everything to "turn myself into a real man". I played sports, went hunting with my family, dated girls, told gay jokes, called my friends ******s, even joined the Army and became a Paratrooper with 2 combat tours. Just to prove to myself and others that I was a man!
After I got out of the Army in Spring of 91, I went to college using my Montgomery G.I. Bill. While there, I had heard rumors about gay clubs in the city. I would go to the street it was on and sit on a bench that was across the street from the club, and just watch the people going in and out. I wanted to go in, but I was too scared. I was afraid of what people I knew would say about me if they found out. I just sat outside for hours. I did this a few times a month. I don't know what I was thinking or expecting by doing this, I guess I was just trying to work up the nerve to go in.
One night while I was being a chickenshit as usual, a "lady" sat down next to me. She asked me if I got banned from the club because I would watch but never go in. When she spoke, I knew right away she wasn't female. My surprised look scared her. She starts to get up, apologizes, and said she mistook me for someone else. I asked her to sit back down, I wanted to talk. Her name was Samuel/Samantha. She was a crossdresser with all the details. Makeup, wig, high heels, purse, and to my shock, IN PUBLIC! We talked on the bench for a bit. I asked her a million questions. Do people make fun of you? Where do you get your clothes and wigs? Do you get funny looks buying women's clothing? On and on, why she didn't walk away from me and all my questions is beyond me, but she answered them.
Now this is way before the internet, finding this kind of information back then was almost impossible if you didn't know where to look. I had what I thought was going to be my only opportunity to see my dream all the way through. She asked me if I wanted to go back to her place and smoke some weed. I absolutely did. We hung out at her place, got high, she showed me some of her outfits, showed me the magazines she bought to learn how to do makeup, and through those magazines she would find ads for wigs and fake breasts, then through one of her orders, she came across a company catalogue that specialized in Crossdressers. I ended up subscribing to that magazine for 5 or 6 years, then the internet became popular and I could find specific information at a moment's notice.
Sam helped me with dressing up for the first time. I had all this makeup, a wig, heels, a summer dress, falsies, bra, panties, nylons, garter belt, and no clue how any of it worked! When Sam was done with her magic, I looked almost as good as her. We went out to that club I ***** on and walked up and down the street trying to get laid. Seems gay guys weren't into crossdressers like they are now. We didn't get any action that night, but other times we did get lucky.
After a few tutorials from Samantha, I was almost good at putting on my own makeup. I was really good at walking in high heels, and I absolutely sucked at finding my feminine voice. I had two options, my deep voice that I have naturally, or a Mickey Mouse voice because I suck at impressions. I whisper most of the time on a date.
The only time I ever went out in public as a CD, was with Samantha. She was my rock. As long as she was with me, what others did or said, didn't matter. With her I was confident. The rest of the world didn't matter when her and I were together. She was the best friend I ever had. I lost my friend Oct 3rd, 1999 to a car accident. I haven't been out in public since her passing.
Anyways, that is how I became a crossdresser.
I tried everything to "turn myself into a real man". I played sports, went hunting with my family, dated girls, told gay jokes, called my friends ******s, even joined the Army and became a Paratrooper with 2 combat tours. Just to prove to myself and others that I was a man!
After I got out of the Army in Spring of 91, I went to college using my Montgomery G.I. Bill. While there, I had heard rumors about gay clubs in the city. I would go to the street it was on and sit on a bench that was across the street from the club, and just watch the people going in and out. I wanted to go in, but I was too scared. I was afraid of what people I knew would say about me if they found out. I just sat outside for hours. I did this a few times a month. I don't know what I was thinking or expecting by doing this, I guess I was just trying to work up the nerve to go in.
One night while I was being a chickenshit as usual, a "lady" sat down next to me. She asked me if I got banned from the club because I would watch but never go in. When she spoke, I knew right away she wasn't female. My surprised look scared her. She starts to get up, apologizes, and said she mistook me for someone else. I asked her to sit back down, I wanted to talk. Her name was Samuel/Samantha. She was a crossdresser with all the details. Makeup, wig, high heels, purse, and to my shock, IN PUBLIC! We talked on the bench for a bit. I asked her a million questions. Do people make fun of you? Where do you get your clothes and wigs? Do you get funny looks buying women's clothing? On and on, why she didn't walk away from me and all my questions is beyond me, but she answered them.
Now this is way before the internet, finding this kind of information back then was almost impossible if you didn't know where to look. I had what I thought was going to be my only opportunity to see my dream all the way through. She asked me if I wanted to go back to her place and smoke some weed. I absolutely did. We hung out at her place, got high, she showed me some of her outfits, showed me the magazines she bought to learn how to do makeup, and through those magazines she would find ads for wigs and fake breasts, then through one of her orders, she came across a company catalogue that specialized in Crossdressers. I ended up subscribing to that magazine for 5 or 6 years, then the internet became popular and I could find specific information at a moment's notice.
Sam helped me with dressing up for the first time. I had all this makeup, a wig, heels, a summer dress, falsies, bra, panties, nylons, garter belt, and no clue how any of it worked! When Sam was done with her magic, I looked almost as good as her. We went out to that club I ***** on and walked up and down the street trying to get laid. Seems gay guys weren't into crossdressers like they are now. We didn't get any action that night, but other times we did get lucky.
After a few tutorials from Samantha, I was almost good at putting on my own makeup. I was really good at walking in high heels, and I absolutely sucked at finding my feminine voice. I had two options, my deep voice that I have naturally, or a Mickey Mouse voice because I suck at impressions. I whisper most of the time on a date.
The only time I ever went out in public as a CD, was with Samantha. She was my rock. As long as she was with me, what others did or said, didn't matter. With her I was confident. The rest of the world didn't matter when her and I were together. She was the best friend I ever had. I lost my friend Oct 3rd, 1999 to a car accident. I haven't been out in public since her passing.
Anyways, that is how I became a crossdresser.
1 year ago