I Learned Early That Playing Mary Was A Sexual Turn On For Me

This goes back go when I was a teenager in the late sixties. I lived in Toronto which is a big city, with all the sins that come with the big city. I got an afternoon job working for this store that sold binoculars, and ham radios, and all sorts of stuff for electronics. In the back they sold things for the police department, not available to the public. The owner was Jack, who was an Englishman, who had come over after the war. He had been a communications sergeant.

It started slowly. Jack wanted me to learn all about everything he was selling. I wanted to go to college not be a shopkeeper. I was growing my hair out to fit in with all the other hippie worshippers and he told me to get a haircut. If I wanted to look like a girl he was going to treat me like a girl and started to call me Mary.

One day he brought some makeup and he painted my cheeks red and applied lipstick. He held my face and kissed me, like kissing a girl. He gave me a dress a wear and a pair of women's panties. With a bow in my hair, he kissed me some more and 'made love to me', taking my virginity.

From then on I was Mary and dressed as Mary and wore the panties he brought me. He kissed me and made love to me and I enjoyed his cock in my hand and mouth and liked being Mary. Eventually I finished high school and went to college to study to industrial design. I always had a dress or two, and always several pair of panties. I would dress up, wear make up, and go out and have a man pick me up and make love to me.

I finished college and went to work for a large company designing aeronautical equipment. Always with my alter ego, dressed as Mary, I found sex with men of all sorts. On one of those outings, I ran into a man who worked at the company. He was very interested but I felt that I had to get out of there. He followed me out into the street and held me and kissed me. He reached for my crotch to confirm I was a guy, and then marched me into an alley. After a lot of kissing and sucking my cock, I managed to get away from him. It was a close call, in those days if discovered you lost your job and everything.

As I grew older the Mary outfit no longer suited me, I had grown to be a man with heavy male characteristics. I went out and if I spotted a guy in a woman's dress I was always interested. Many times if I had a guy over I dressed in panties. To this day, and I'm very much older, I still enjoy playing the woman, for example wearing a flowery apron, with nothing else on, and having the man make love to me.

Comments

Anonymous

by Anonymous on Aug 19, 2025 at 9:32 AM

I absolutely love feminine men. It makes me so hard to hold and make love to them. I really enjoy men with small shaved cocks the best, and if they have panties on when I meet them, the panties don’t come off t8ll I’ve cum in that sweet tight ass.

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Anonymous

by Anonymous on Aug 20, 2025 at 10:30 AM

I've been Mary, Mary, quite the fairie since I was in kindergarten. Panties instead of boy's cotton underpants kind of sealed my fate with boy's who prefer girlish smooth sweet faced boy's.
I was too young to get anything more than a tingling sensation when an older boy forged about me in panties but it was good enough to keep me coming back. I bottomed for another sissyboy in panties who was 15 when I was 9.
The real clincher came when came aa a panty bottom two weeks before I had my 13th birthday. Gosh his boycock tickled my senses as my perfect boipussy clenched spasming uncontrollably. Wow was I in love....

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