First Time Fantasy
Keywords: Fantasy, Time, First,
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I'd never had a real experience before. Years of wearing panties and fantasizing, but nothing legitimate. I imagine it's the same story as many other panty lovers: started when I was about 13 by stealing some of my mom's things. Bras at first, then panties. Soon I began looking forward to being home alone so I could slide on silky under things. When I got the internet in my room I started chatting more and more, and then dressing at the same time. This continued through high school.
Fast forward to university; same deal. Although then I fell into the dangerous habit of stealing panties. You know, late at night, after a wild house party when everyone was asleep. I'd creep through the house, drunk, and search through drawers in the dark for anything silky. Panties are so small they're easy to shove down your pants and conceal. My record was carrying 7 pairs inside my own underwear until I arrived back home with my friends! A very dangerous habit, but so very exciting. Believe me, nothing beats sliding on a pair of 100% silk string side bikinis previously owned by a hot 22 year old university girl and cumming like a little slut.
But these are other stories! Eventually I had my own apartment and bought some panties and things on the internet. I loved sliding these girly things on, feeling feminine and fantasizing about being fucked like a girl, servicing a man. Eventually I got a dildo and started fucking myself whenever I put panties on, the backside pulled aside harshly so I could still wear the panties and have the pleasure of cumming in them. The next step was phonesex, which I could only do if I was extremely horny. Usually this only happened after hours of hot chatting so I was flushed like a girl, my panties soaked with precum. During my first experience with phonesex I nearly cummed inside my panties only seconds after picking up the phone out of sheer excitement. To this day I've only ever been turned on enough to do phonesex maybe 4 or 5 times.
It takes a lot of courage to organize a meeting, and a lot of time. I had chatted a lot, and played with the idea of meeting a man for the first time, sent some emails. But it took years before I ever made a positive plan. The first meeting I ever had was strictly for dressing, no sex. A fellow cd invited me to his house and we dressed in different outfits while his wife was at work. We changed clothes for hours like two excited schoolgirls. Eventually I got hotter and more mentally feminine - this was the first time I had the pleasure of wearing stockings and a garter belt, and it made me ultra horny - and played with a dildo in front of him; my panties pulled aside, skirt hiked up and stuffed bra cups bouncing.
As I sat on the dildo he moved behind me to watch it slide in and out of my freshly shaved ass. Out of the corner of my eye I could see him fiercely jerking off - he wanted me, and I don't blame him: I was perfectly girlied up in a plaid kilt, white satin panties and matching bra with a white garter belt and stockings. Being dressed like that, and feeling my girly hole being stretched, I would have easily sucked him off (it would have been the first time I'd done anything like that). All he would have had to do was move around in front of me and dangle his cock in front of my face. But unfortunately, nothing of the sort happened. By the time we were ready to change into out final outfits - the ones we would jerk off in - I was so girly and aching for cock. I changed into different panties, bra and stockings, this time being careful to make it obvious that I had slid the panties on over the garter belt like a little whore. But we had agreed that we would only meet for dress, so after cumming, I went on my merry way.
This first experience taught me how easy it could be to meet, and I began fantasizing more and more about a sexual encounter, either with another cd or a man. It's funny though, I was never attracted to men, only to the idea of being a girl for one. I loved girls, and still do. It's ironic that the idea of kissing a man disgusts me, yet the idea of being fucked my one turns me on! Anyway, I began chatting to more and more men who were looking for a cross-dressing girl to use. There was obviously plenty of interest. Some were just jerks, some never replied to emails. Some wanted to take me shopping for clothes to wear; this idea turned me on immensely, but I was way too shy to risk being exposed in public. So my search continued. And actually, it still does. I have yet to find the perfect man - or rather, "cock owner," for this is what I actually want. So, the following is a fantasy. Maybe it's an ideal picture of how my first time would be, I don't know.
We'd chatted on the internet plenty of times, at first in public rooms and later on MSN. Lots of cybersex and email meant that he knew exactly what kind of girl I wanted to be: shy and innocent, but ready to please and be used like a toy. Many times he had made me orgasm like an angel in my silky under things. We had talked about a meeting, and he was very anxious. He knew my pussy was virgin, and super tight. He wanted to be my first cock, and perhaps this is the reason he was so patient, enduring months of cybersex before the real thing. I had also explained that my first time, if it were to happen, would have to be perfect: perfect clothes, make up and so on. He had only one request,
"I want you in virginal white."
I readily agreed to this, as it seemed appropriate. After weeks of schedule checking and nervous procrastination, we set a definite date. I was to meet him at a hotel downtown in the afternoon. I need not bring anything; he'd have the clothes and make-up waiting for me. When the day came, I prepared extensively. I carefully shaved all around my ass, or "pussy" as I always called it when chatting, until I was smooth. I did the same around my cock, and soon I was completely bald in all the important places.
After showering, I rubbed a generous amount of baby powder over these areas until I felt entirely girly. Baby powder was ideal; it made my skin smooth and it's scent was not strong enough to be detected on the subway! Lastly, I decided to slip on some panties under my jeans. I knew he had said he'd have clothes, but I needed to feel girly during the trip downtown. This would help ensure I didn't chicken out and turn back. I selected a little satin thong in pink; it had always done the trick when I wanted to feel feminine. It's material was very thin and flimsy, and it barely contained my cock. I also ensured that the string sides rose above my jeans onto my hips. This was a favorite trick of mine - I'd wear a long shirt to cover the panties, but just knowing that they were potentially visible was such a turn on.
And so I set out for the hotel. the subway ride was uneventful, but I enjoyed the feeling of my panties on my soft skin every time I moved. By the time I arrived at the hotel I was hard, and my little thong could no longer contain my erection. I stood outside the hotel for nearly half an hour, my nerves tingling. Many times I almost turned around and returned home. Finally I had to move. I had arrived early, but now I was late. I summed up the courage and walked into the hotel, straight into the elevator.
The hotel halls were quiet, which made me even more nervous. Occasionally I passed a person and paranoia set in; it seemed like everyone knew where I was going and what I was about to do. The feel of my little satin thong between my cheeks was driving my wild though, and I kept walking. I reached his room, and, after some more procrastinating, knocked. It seemed like an eternity before he answered the door. I don't know if he was handsome or not; as I said before I had no interest in kissing him, only in being his girl.
"Juliah?" he asks, for this is my favorite girly name. I nod because I'm too nervous to speak. He invites me in and I notice my outfit carefully laid out on the bed. I crouch down to inspect everything, letting my shirt ride up and exposing the top of my little thong above my jeans. I hear him sigh and fall silent at this sight.
I examine the clothes, most of which we had agreed upon earlier, some of which were his ideas. Shiny white satin string side panties with pink lace trim around the legs and hips, tied at the sides with cute little bows. A sexy pink and white satin and lace bra to match these. Sheer white thigh high stockings with black satin bows at the tops, and a cute pink satin garter belt. A shiny white satin chemise lays beside these, along with a light brown wig. I stand up and my cock is already hard under my jeans.
"Everything else you'll need is in the bathroom. How long do you need to get ready? I'm going out, and I'll be back in about an hour, is that all right?" I tell him yes. He thanks me and leaves the room. It's 2:00.
I inspect the clothes further and discover they're expensive; the panties are not satin, but silk, as are the stockings. I can't help to feel special being pampered like this, and this makes me feel more girly. I grab the clothes and go to the bathroom, where my makeup is waiting. Lipstick and eye shadow, along with lip-gloss and perfume. Some fake pearl clip on earrings and a matching necklace are on the counter. He wants his little girl to be beautiful! After removing my shirt, I decide to do the makeup first, because this would be the difficult part. I have little experience with makeup. The lipstick is easy, and I spread the light pink shade over my lips evenly. The eye shadow is harder, and it takes me a few tries; I have to start over several times. By the time I finish I'm looking pretty hot, considering my lack of skill, and and kiss at myself in the mirror.
It's time to get dressed. I take off the rest of my clothes and slip the bra on first, carefully inserting the jelly like breast forms. Next I let the satiny chemise fall over my breasts, admiring the way the material curves around them.
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Keywords: Fantasy, Time, First,