Crossdress For Sex

This confession may sound made up or off the wall but it's true. I am a crossdresser, I have been dressing since I was in my teens. When I had the chance I would put on my older sisters things and I love how I felt wearing them, so feminine! As the years passed I got married, three kids so all of that stopped, I still had that strong desire but was so paranoid about getting caught and found out. Fast forward......I got divorced, retired and the kids were grown and on their own and scattered all over the country. I live way out in the country and being alone so much I started dressing again, the feeling was even stronger than before and I was dressing everyday at some point and I loved it! I guess it had something to do with age, mid-sixties, but I wanted to dress feminine all the time. I liked the way I looked and how it made me feel make-up and all (which I got very good at) and I felt my manhood slowly slipping away. I was buying things, thanks for Christmas and even Halloween and Valentines Day and soon I had a complete wardrobe. I started watching porn with men and crossdressers and that urge came over me and soon that's all I was thinking about everyday. I went to the adult book store and bought several dildos and to satisfy the urge I would dress late at night then get into bed with my store bought cocks and fuck myself until I would cum thinking this is close to how a Woman would feel. Over time and watching more crossdresser porn the urge to be with a man for real came over me like a tital wave. To get caught would be total humiliation and would surely ruin my life. Nevertheless I continued looking on a site called Locanto and there it was........the ad read "Single Dominate man looking for a Crossdresser, must also be single and must understand I am very demanding". Along with the ad was a photo with a picture of him standing by his pool naked and to say he was well endowed was an understatement. I was not sure about this and after looking over the ad and the picture for over a month I answered! We texted, then we phoned then planned to meet a a nice restaurant the fallowing weekend. As they say it's now or never so we met! The rest of the story is coming!

Comments

Anonymous

by Anonymous on May 2, 2024 at 4:49 AM

Oooohh....I love crossdressers. So hot. Can't wait for your next installment.

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Anonymous

by Anonymous on Oct 13, 2024 at 5:42 PM

My grandmother made my father crossdresser, my mother told me she used to dress him as girl… little did she know I got started by my granny too, by teen years I was using all my mom lingerie, she has a good collection, then I basically used all woman clothes I was near to, all girlfriends, I would steal undies and if possible even dresses from neighbor girls, at college I even learned how to break into the departments in the building and I got dresses with a lot of the girls around, I loved to use a SIL jeans and skirts, I started going out dressed, even with a dildo or vibrator inside my butt, I did way too much, except getting fucked, I should have, the only experience I had was with a tranny but no sex, just touching and kissing… I stopped when I found my wife and finally got into actually satisfying sex, she is great in bed and also likes anal both in her and me, so I get my need to feel girly satisfied so good. Sometimes I get the idea of dressing up but is not big enough anymore

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