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I'm going through some of my first steps into the real world as a crossdresser myself so I was wondering what are some of your favorite moments you've had while crossdressing?
STLCD STLCD 22-25, M 14 Answers Jul 29, 2012

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There are a couple that I have really enjoyed most. Shopping and trying on women's clothes in the dressing room was great. Having a profesional make-over and discovering my full femme potential was also fantastic. Good luck.

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Answering the door to recieve a package from the the UPS lady wearing my thigh high boots with a 5" spike heel.

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I love wearing my partners hoodies and sweatshirts and I wear his t shirts sometimes too. They smell of him and i love it :-)

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I'm not a crossdresser now but when I was in my teens I was very feminine-looking and (according to my female friends), very pretty. Sometimes when I went to parties they encouraged me to dress up as a girl, and since I was gay (and just out of the closet) I thought it was a lot of fun. I was short for a boy, and delicately-built so it was easy finding girls clothes to fit. When I was dressed up and wearing make-up, and putting on my "girl voice", people thought I really was a girl. The experience I enjoyed the best was a "girl's night out" to a nightclub in Liverpool when I was 21. Not one single person guessed that I was a boy.



As an adult, it wasn't so much fun. I did dabble in the drag scene early on but I didn't enjoy the theatrical aspect of it and the makeup got harder once I was growing facial hair.



It's been twenty years since I last wore drag, and though it was a fun time in my life, I don't really miss it at all.

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never having had 1,,, that's my #1

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wearing a tuxedo to a party

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The two times that I got to go out and pick out two formal gowns. I know that's a common thing to wear as a crossdresser but I will never forget going to JCPenny and trying on different gowns until I found the one I felt most comfortable in.

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When I was 17, I found some of my mother's old clothes. I dressed up as her and was shocked that I looked just like a picture of my mother when she was 19.



I got a paddle, pulled up the skirt and pulled down the paddle and spanked myself.



I wish I had pictures of it.

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Probably being accepted by my partner and actually being able to sit with her whilst cross dressed. Up until that time I had never been with another person (except paying for sex cross dressed) cross dressed only ever done it on my own. It was the greatest feeling.

Felicity

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You paid for sex while crossdressed? That ought to make an interesting story.

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I always go out to eat in 5 inch heels and a silk dress with panties bra and my pretriest makeup and blonde wig

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I got to go a a party dressed up. I loved it.

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Going shopping and letting the salesgirl know it was for me. Being dressed and tsken with a ******* while s party room watched.

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