Meeting Charly

Getting Ready - Jamie

Waiting in the hotel room "she" checked herself out in the mirror; for as masculine as she looked during normal times the look wasn't half bad even if it was a little dated.

The hair was a short pixie bob style with bangs, when she shook her head the feel of the ends tickle her neck just the way she liked it. A black bra 42 with a B cup, her breasts filled these nicely without falsies, she hated falsies as her nipples were very sensitive and it felt so good feeling them rub against the material. The garter was black and lace and the hose were jet black (some to hide what hair was on her legs but mostly because she loved black hose on her legs). Panties were a full cut nylon pulled up over the garter and hose, she wanted to be able to leave these on for her guest even if everything else came off at some point!

The dress was a brown velvet material, it was her favorite. The dress fell just below her knees (no miniskirts for this gurl), when she walked it felt so good swishing against her nylon covered legs and looking in the mirror her breasts stood out just enough to give a little cleavage. She had used a red lipstick and her lips were perfect, deciding to go all her eyes were lined with a sky-blue glittery mascara and she had done her eyebrows as best as could be done. The heels were a light brown, 2" and round toed, it had been ages since she had been in heels, but it finished off the look and felt good! Again, looking in the mirror the look was not bad and she could be mistaken for a girl...from a distance at least.

Mistaken? Yes, "she" (Jamie) was actually a man, a crossdresser. You've read the stories of men crossdressing, they all seem to be slight of build, feminine qualities and destined to be women. This was not Jamie's story. From a young age for at least as long as he can remember there was a fascination for women's clothes. Jim (his real name) was not slight of build, he had a normal build for a boy his age, his voice was not high and he detested playing with dolls or other feminine toys. Always a rough and tumble kid, the only time this desire would appear is when he was by himself and he could indulge. Dressing up in his grandmother's girdles, putting on her lipstick and occasionally when time permitted a dress or two. Same with his mothers things, neither women were particularly sexy women but putting on these clothes was exciting and he knew it was not "right" but that was part of the thrill.

Reflecting back on all of this while waiting for her visitor she never knew where the compulsion came from or understood it. Never knew of it as crossdressing until later in life and thought she was the only one. Finding out that this was a true desire, well that is a story for another day. Right now her visitor was about to be there and she was very nervous and excited!

They had met on the Internet. Another part time crossdresser and had been talking for months. Unlike Jamie his wife knew of his desires and supported him, at least that is what he had told Jamie and she believed him based on the pictures he sent. So lucky! "If my wife supported my dressing that's as far as I would go!" Jamie thought out loud. Talking for months because it took her that long to get up the courage to meet, their conversations had sometimes gotten steamy and Jamie was very hot and desired her very much. They agreed to meet at a motel between them and the date was set. Jamie said she would get the room and let "Chuck" know what motel and what room when she was there. She had done this early and dressed now waiting. Would he show? What would he look like? Would they be attracted to each other? All these questions swirling around in her head was making her dizzy and she giggled to herself, it was like a first date in high school and for all the nervousness she was excited it was finally going to happen! The knock on the door came! It was time, getting up Jamie made her way across the room, her hand shaking with excitement pulled the door open..

Getting Ready - Chuck/Charly

I've never done anything like this before, standing in the shower washing myself after just taking an enema to make sure I'm nice and clean, soaping myself up real good, gently playing with myself thinking of what is to come. I've shaved my face, lower stomach, rear end, balls and cock for her so their nice and smooth. I can't believe this is finally happening, a lifetime of fantasies dreaming of finding another guy who feels like I do and wants to be a woman only with a real cock that cums real sperm.

When I was just coming into sexuality at age 11, I had feelings and no one to talk to. My dad was killed when I was 8 and it was just my mom and me. Anything I learned about sex was in school as there was no real porn or internet. I enjoyed fingering my butt and masturbating. Sometimes I would put on a pair of my mom's panties for a while. They felt good but I was to afraid of getting caught so I didn't wear them long. I learned to make out with girls and what sex with them was all about. But I secretly longed for something else. Once in the Boy Scouts there were 4 of us in a tent, naked, talking about having a hard on, and just when we were going to engage our pleasures the scout master peeked in, scolded us, and told us to get to sleep. It was never mentioned again. When I was 18 another guy, friend of mine, kissed me in a store for kicks. It never happened again but I thought about it often, the forbidden fruit, and masturbated to the thought of the feel of his lips.

Over the years I'v always wanted to get sensual with another man but never had the right moment. When it may have been possible I backed out. Men don't turn me on but a "chick with a dick' does.

I'm excited, nervous and scared as I put on my crotchless pantyhose, panties and slip my dress over them to meet my internet lover, Jamie. I'm going to put my pants and t-shirt over the dress and head to a room she picked out for us to meet. I hope my body excites him when I arrive. I won't be in a wig or make-up and I hope it doesn't turn her off. Since I'm an ass man she's sent me pics of her rear and it is very hot. I want to squeeze it and rub my hand up and down it. I'm excited about our first kiss, hopefully as soon as I walk in the room. I saw her in the AFF site and when she lifted up her dress and started touching herself I got very excited.

After my 3rd wife, Nancy, told me she was bi-sexual and wanted to see me in skirts, dresses, wig and make up it awoke up a whole new girl in me. I get so excited when she puts her cock on and makes me suck it then pulls down my panties and gently fucks me. I love dressing up for her as I know she thinks of making love to another woman. She's masculine and loves to fuck me. But now I'm going to make love to a woman with a real, throbbing cock and thoughts of tender lovemaking. So many things me and Jamie have discussed and I hope to make all of them a reality in time.

Thoughts are racing through my mind as I get closer to the room. I'm very nervous but can't wait to feel her lips on mine, her hands on me, stroking, caressing. I hope she takes my hand and leads me to a chair where she wants to sit on my lap, cocks touching, and put lipstick on my wanting lips.

I'm here, time to knock on the door and melt into a new sexual freedom

My first time writing, I have continuation if I should.