First Time Experience
by Princess Pervette
Every once in a while I read about women who like to put their men in dresses, and I wonder whether anybody really believes such women exist, or whether they think they are just crosdressers' fantasies.
I believe in them. I knew one. Joanie liked to put her men in dresses. She put me in one; and that's how I first got started being a crossdresser. She was a fag-hag, actually, but I guess that in me she found someone who was not too gay to keep her happily fucked. Anyway, we lived together that summer, and when she started hinting that I might look good in drag, that I might enjoy being a drag queen, I was receptive to the notion.
I was 22 when this happened, so I guess I was a late starter. I had never given any thought to wearing drag as a boy, or an adolescent, but when she begin hinting about it, it struck me right away as something I wanted to try. In part, the idea sounded good to me precisely because society disapproved of men who crossdressed, and anything I could do that society might disapprove of was just fine with me.
She had told me a number of times that I would look good in drag, and she knew I was playing with the idea. So one evening, after dinner, Joanie said to me, "This is it, Girl," and I said Okay. She went rummaging through her dresser and closet to find things for me to put on and brought out a selection of underwear and dresses.
I was going to start with a pair of panties, but Joanie overruled me. "Garter belt first, Girl. Those panties are going to come off for somebody, and they'll come off a lot easier if you don't have to remove a garter belt to get at them." So on went the garter belt, and then a pair of nylon stockings.
I found I enjoyed it right from the start. I loved the experience of putting on all these mysterious underpinnings and foundations that I had always seen, in ads, on Joanie herself, and on other women, but had never actually worn. The nylons felt terrific I drew them on my legs--so snug and yet so comfortable. (For this first time I hadn't shaved my legs, but I did the very next time.) I liked the way they changed the color of my legs to a darker, sexier shade, and the way they smoothed out the contours. I looked down at my legs and realized with a shock that suddenly they were women's legs. Then came the moment when I had to secure the stocking tops to the clips on the garter belt. This was something I remembered seeing my mother do when I was a little boy, and here I was doing it myself, with stockings that were on MY legs and a garter belt that was around MY waist.
Then came the panties.. It would probably make a better story if I could tell you that they, and the garter belt, were black and adorned with a black, hazy mist of lace; but in fact they were plain pink. In a way, that made putting them on a more meaningful experience-- no, meaningful hell, a devastating, mind-blowing one--because it said that I wasn't being a girl as a sort of special or exceptional occasion, but just routinely, as if I feminized myself regularly, as a matter of course. And I think that was the moment when I first realized that yes, I WOULD be feminizing myself as a matter of course, now and in the future.
The bra presented the usual problem. Joanie didn't need breast forms and didn't have any, so she wadded up handkerchiefs and stuffed the cups with those. She was keeping me away from the mirror--she didn't want me to see how I looked until we were finished. But I looked down at my body, at my bra, my panties (MY panties!), at those wonderful, sheer, nylons, and realized with a thrill that this was something I had always, unconsciously, wanted to do. I began to feel a stirring in my loins. It was a bit of an anticlimax, in fact, to put on a slip and cover up all those enchanting undergarments.
I remember that she picked out a blue and white striped dress for me to wear. She helped me put it on over my head, helped me draw it on, and after I had zipped up the side, she patted it down. "It's a little short for you, my girl," she said, "But then you're going to be a little slut, anyway--aren't you?--and of course you'll want short skirts. Besides, it shows off your legs this way."--and at the thought of being a slutty girl who wanted to show off her legs, the stirring in my cock became a little more imperative.
Joanie took the longest time fussing with my makeup. I didn't know what all the steps in the process were, that first time, but she must have applied some sort of foundation and then some blush to my cheeks. I didn't really pay much attention to this, because I kept wondering when she was going to put on the lipstick. Somehow wearing lipstick seemed the ultimate, girly thing to do.
Finally she got to the lipstick and, instead of applying it, handed the lipstick to me and had me put it on myself. She explained, later on, after we were all done, that she could sense me getting more and more interested and enthusiastic about the project as it went on, and figured that, since this was obviously not going to be last time I wore drag, I might as well learn to do these things myself. Similarly, she explained how to apply eye shadow and mascara. Then came nail polish and we were done, I thought.
We weren't. Joanie did some more rummaging about and came up with a scruffy-looking wig. I hadn't known she had such a thing. How many other boys had she bedecked with that wig, I wonder. She very carefully put it on my head, and then got out a comb and a brush and seemed to take just forever combing the wig and fussing with it. It took so much time, partly because the wig had not been carefully stored and needed to have the hair straightened out, but also because Joanie was, in her way, a perfectionist.
Finally, she found some high-heeled shoes that I could just manage to get into, and then she really was done. In TV fiction, there usually comes a moment when the hero(ine) looks in the mirror and sees a pretty young girl reflected there. I can tell you that that doesn't happen only in fiction. At Joanie's prompting, I teetered on my heels over to the mirror, and, sure enough, there was the pretty girl. I was devastated to realize that that pretty girl I was looking at was myself. They didn't use the word "transformation" back then, but that's what it had been. I had been transformed into a girl, just as surely as if Joanie had gelded me. It was curious that my reflection stirred no trace of sexual desire in me. I didn't have any wish to reach through the mirror and grab the pretty girl, or the pretty, made-up boy that I saw there. I felt curiously neutral toward my reflection except for a mounting excitement as it came home to me that that pretty girl in the mirror was me.
I wore Joanie's dress the rest of that evening as we sat around and talked. I knew I was going to like crossdressing, and I told Joanie so. She was thinking of all the various outfits I could wear; I spent some time wondering whether I should take a drag name, but most of the time I just sat there and, as one garment or another-- the panties, the bra, the shoes--called attention to itself on my body, I marvelled afresh at the fact that I was actually wearing drag. I asked her about the drag name, and we considered various possibilities; finally we settled on Debbie. She rarely called me that in our time together, however; most of the time I was just "Girl."
Came bedtime. How sad it was, to have to take off all those lovely things! Joanie offered to lend me a nightie, and I accepted, but I said that I wanted to sleep in my panties, too. And so I did. I remember waking up a couple of times in the middle of the night, feeling the unaccustomed tension around my waist and crotch, remembering that those were the panties I was wearing, smiling happily, and going to sleep.
And the next morning I woke with that feeling you sometimes have, when you know you've received a piece of cheering news and are still too foggy-brained with sleep to remember quite what it was. And then I remembered that I had spent the last evening in drag, and that that was the beginning of a new era in my life, and all the rest of the day I felt a warm glow of happiness at the thought. The glow lasted through the day at the office, even though the day seemed to stretch out forever. I was so impatient to get back home again and back into a dress.
That evening, Joanie came home after work with an armload of packages. She had gone shopping for me. "Can't have you wearing my things, Girl," she said. "You'll have to have some of your own." There were panties, a couple of bras, a couple of nightgowns, a blouse, and a skirt. The underwear was decorated with flowers, little ribbons, and wisps of lace, except for one pair that seemed to be all lace. She hadn't asked me about these; she hadn't needed to ask. It was remarkable how well Joanie understood me, in some ways.
And from then on, every evening, after I got home from the office, the first thing I did was to strip off my boy clothes and get into drag or, as I thought of it, to get BACK into drag. It always felt so good, doing that. Over the next few months, Joanie helped me accumulate a nice assortment of panties, and, as soon as I judged that I had enough panties, I threw out all my men's underwear. I'm happy to say that, from that day to this, I have always worn panties under my outer clothes, although I don't wear a bra except when I'm dressed.
Once something came up, and, preoccupied, I didn't change after work. Joanie came home, took one look at me, and said, "What's the matter, Debbie? Forget your girly clothes?" Now, Joanie was never what I would call a dominant woman; certainly our relationship had never had any of that sort of thing in it; but there was a note in Joanie's voice that evening that was not to be denied. And I realized with a thrill that Joanie expected me to crossdress every evening at home and might possibly find ways of enforcing that requirement. But by this time, I was so crazy about wearing drag that no enforcement could possibly be necessary. Nevertheless, that evening, our relationship subtly changed. And she started asking me to wear my stockings and garter belt when we had sex--and sometimes my bra, too. Well, they were exciting to wear, so I had no objection to doing that. In fact, it seemed to heighten the excitement for both of us.
She took to making remarks about how fuckable a girl like me would be. Even sometimes when we were having sex, she would say, dreamily, "It's funny, you fucking me. You're such a girl, you should be the one getting fucked." Well, I had been fucked plenty, so that wasn't anything upsetting to hear. In fact, I remember having sex with her one evening on a day when I had spent the afternoon at the baths and HAD gotten fucked, a couple of times. But one day she brought home a butt plug. And after that she expected me to wear the butt plug in the evening along with my girl's clothes. Once in a while she would have me bend over for "inspection," as she called it. I wonder now why she never got a strap-on to fuck me with; I certainly would have liked to try that.
Her campaign culminated on the Saturday after my birthday. Joanie told me she was having a special birthday party for me. She said we would have company that evening, but that I was to dress as Debbie, as usual. (Up to that time, any time we had guests, I had always dressed as a boy.) That day, since it was a Saturday, I wasn't going to work, and I got up and put on my drag, as I always did first thing Saturday morning. But in the evening, after dinner, Joanie had me put on full makeup, too, which I normally skipped, except for lipstick. She then went over me in detail, combing and brushing my wig, checking every detail of my appearance, and carefully exaggerating the makeup so that Debbie ended up looking like a regular slut. Then, at the end of this process, she doused me with cheap perfume.
The first guests showed up at 8:30. Two of them were gay guys we both knew, but they brought a couple of friends with them. They said something to Joanie about having promised to bring them, and I realized that Joanie had more in mind than I had thought. She introduced me to the strangers as Debbie. They for their part were delighted by my appearance. They looked me all over, cooed over me, poked and fondled me almost as if I were a kitten rather than a man in drag. They said things like,
"Doesn't she look sweet!" "Isn't she a perfect GIRL!" (How I loved hearing them call me that!) "Look at her eyes. Is that mascara, honey?"
Before I could answer, one of them grabbed the bra through my dress and asked, "Is that for real?" Then he felt the stuffing and said, "Oh. No. That's stuffing."
"That's okay, they LOOK real enough for me." "And that won't give us any trouble when we enjoy her later." That REALLY alerted me.
In the end there were five guests, and there wasn't much doubt in my mind that the entertainment, at this party, was going to be me, in my girl's clothes. We sat around, drinking and talking quietly, while I wondered just what was going to happen, and when...and how.
It started very simply. In a lull in the conversation, Joanie said, "It's time to give Debbie her birthday present." She disappeared into the bedroom and came out carrying a box, gift-wrapped and swathed in ribbons. She put it into my lap with a flourish. "Here you are. Happy birthday, Girl!"
I opened the box, and inside was a teddy, black, with a front panel in black satin and sides in black lace, and with what seemed like a regular mass of black lace all over it. Along with the teddy were two pairs of black fishnet stockings. I hadn't owned a teddy; it was beautiful.
"Well, aren't you going to model it for us?" Joanie asked. No-one more eager than I. I stripped then and there, put the teddy on, and the stockings. The teddy had long, frilly garter straps for the stockings. When I was finally dressed, Joanie got out a camera and took pictures of me.
Then she looked at our guests. "I think you could start now. She's ready." One of the guests said, "Where? Right here?" "No," Joanie said. "Take her into the bedroom." And I realized that I was about to get my REAL birthday treat: I was about to be gang banged by these five wonderful guys.
Now, it would make a terrific story if I could tell you here that they dragged me, kicking and screaming, into the bedroom and took turns holding me down while they had their way with me, one by one. But I must tell you what actually happened, and by this time you can guess what happened. They didn't need to drag me at all. I was a little apprehensive, to be sure, but eager, too. No, not eager...wild for it. I still don't know, to this day, whether Joanie had set up this supposed birthday treat as a way of victimizing me, or perhaps to derive some obscure satisfaction of her own (she sat there in the bedroom while they used me and calmly watched the whole thing); but I knew that she had somehow planned it, and the thought of being dressed as a girl and gang banged was so hot I was afraid I would come all over my nice new teddy.
But they did TAKE me into the bedroom. When I stood up, they picked me up, carried me on their shoulders into the bedroom in a sort of triumphal procession, and set me down on the bed. From there on it was one delirious blur of sexual excitement. Sometimes on the Net you see an ad from a group of guys offering to any interested woman the experience of being gang banged. No doubt some people wonder at this and at the notion that such a thing should be enjoyable. I don't. I was gang banged for the first and only time in my life that evening, and it was DELICIOUS. I had men in every orifice, and a couple of times in both ends at once. It had all the ingredients a good sex experience should have--arousal, fear, and a certain violation of one's natural fastidiousness--and the thrill of satisfying my men in my teddy, with its puffs of lace and my fishnet stockings (which were in tatters by the end of the evening's frolics.)
So that's my story. Joanie's gang-bang party was a sort of rite of passage for me. I am a crossdresser to this day, and I love it. I've never gone out dressed, except for Hallowe'en and the occasional hot sex date, if I'm going with a guy who likes a partner in slutty drag. I've never been concerned over whether I "pass," either; but the habits I formed with Joanie persist to this day: I always wear panties under my business suit, not only for the pleasure and excitement (which has never left me) of doing so, but also as a matter of principle, as a way of reminding myself of the other side of my life. And the moment I get home in the evening, off come those boring, necessary men's things and I'm into a dress. I have a closet full of nice girly things, although as the years go by I'm gradually changing over to things more appropriate to a fashionable, middle-aged charmer.
Thank you, Joanie, wherever you are.
(c) Princess Pervette
July, 1996