Cross Dressing for Valentine's Day

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With some men accompanied by their wives or girlfriends, making him wonder if this one was a woman or a man, mistaking women for men, he looked around the room and the first ones he noticed were the ones that most looked like women. Some men were stunning and he had to look longer and more closely to discern if they were male or female. Some men looked so good that they looked like professional female impersonators. The one thing that always gave them away was when they looked too perfect. Even women don't look that good.

Then, he spotted some men that looked horrible dressed as women, especially those who didn't bother shaving off their mustaches, beards, and even shave their legs. They looked like characters dressed for ladies night in a beer commercial, just to get the reduce beer prices. He imagined that they must figure, if they shaved off their facial hair, maybe they'd be questioned why they suddenly shaved hair from their face that had been there for years. Maybe they just enjoy wearing the lingerie.

He saw some men that were so tall, especially with high heels and their hair up, that they'd never be mistaken for a woman. Too many men had a face that had a jutting jaw or a bulging forehead and no matter how much makeup, they'd never look like a woman. Yet, that wasn't the reason why they were here. They were here for the same reason he was here. To play dress up and have some sexy female fun.

He realized that each one had a story to tell, just as each one had a reason for cross dressing. Even though they all shared the same desire to cross dress, there were different levels of cross dressing. Even though he'd never have sex with a man, was never attracted to a man, and was one hundred percent heterosexual, he was a rarity in the fact that he dressed more like a woman and could actually pass as a woman than most of the men here. After listening to some of the dialogued, he noticed that many of those men who more looked like a woman were gay or transsexuals.

He'd never go the route of a sex change operation, nor would he get breast implants. This was enough for him, pretending that he was a woman a few times a year, while attending the Valentine's party and the upcoming Fourth of July, Halloween, Christmas, and New Year's parties. With having his hair, makeup, and outfit, that was enough for him to express what he wanted to express.

He was looking forward to going home to masturbate over all that he saw and all that he experienced. As far as he was concerned, his first public cross dressing adventure was a success. He made some friends and he got a chance to talk with men, who were just like him. This was better than group therapy. This was the best Valentine Day he's had in a long time and he didn't even need a woman to have fun.

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  • COMMENTS
9 Comments
Kathryn65Kathryn65over 1 year ago

Simply lovely story probably true for so many people here . Thank you for sharing your thoughts and craft .

shoeslayershoeslayerabout 13 years ago
Very well written

Well superheroralph,

I have to say you did an excellant job with this story.Were i not a part time woman i could not say that but I am and damn glad I am.I suffered the guilt

shame and anxieties any guy would when he found himself donning his moms patent black heels, bra skirt and stuffin socks in to make bossoms.

But I stuck with it over the yrs and my dressing has only gotten better.

working on the railroad an dressing as a woman in her mid 60's has got to

be one of the most oposites in the guy gurl thing,not at the same time of course.

Anyways thanks dearly for a great story,almost as if you really knew or

know a +dresser.

Most sincerely,

Ramona S.

fireguy365fireguy365about 13 years ago
Been there, done that...

It's as if you were writing about me. For the most part, I'm still married, this story is right-on story of my life as a cross dresser, as I'm sure it is for many others. I thank God for the internet because it let me explore the side of me that never would have been experienced except for the internet and a local cross dressers club. I even had a clothing and make-up store that catered to CDs and TGs. Thankfully I wasn't one of those that looked like "a man in a dress". I could pass, from a distance and dim lights, and it was so exciting getting out while dressed and having a chance to be the women that was inside me. Thanks for such a thoughtful and sensitive story.

JentvcdJentvcdabout 13 years ago
Very Good

Very well thought out as far as the way most of us closeted ones think n feel.

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