I want to present a few short vignettes concerning crossdressing. A most interesting and individual form of sexual gratification and fulfillment.
The first story concerns a strong man, happily married and happy with the sex he is getting from his wife, but something seems missing in his life. He often walks the streets and window shops, but seems to be drawn to the windows displaying ladies' wear, from dresses, to frilly underwear, to stylish shoes. He is drawn to it all.
And he forms the opinion that he could enjoy just wearing them once in a while. What could it hurt? It wouldn't harm anyone.
So, over a period of months, he slowly acquires a collection of items that he wears only in secret. Not even his wife is aware. And most interesting of all, wearing these garments causes a great deal of arousal. It is totally sexual but doesn't necessarily include another person.
But he dreams of sharing this love of his with others, especially understanding women, because his desires still race toward the ladies. He just wants to feel the same way they feel when they put on their undergarments, put on their makeup, do their hair, and get dressed to the nines for a night on the town.
He can't tell his wife, but he does have old friends and he takes the chance. He mentions his proclivities to a dear friend from years ago, and, gratifyingly, the friend isn't appalled. In fact he suggests something our friend has only dreamed of. "Let's go out on the town, you in your best and me in mine, and maybe, after we have spent an evening displaying you to the world, something good will happen," his friend suggested.
That is exactly what they did. Our friend, on a night that his wife was visiting her mother, spent hours on his coiffeur, his make-up, and his beautiful dress with the matching pocketbook and low heels. And when his friend appeared he expressed a great deal of approval, giving him a kiss on the cheek, and saying, "Is my lady ready for the evening?" Our friend was very ready.
The old friend had rented a limo, and they went to the best restaurant in town. They made a grand entrance, the old friend dressed in a rented tux, and our friend wearing his best gown. They were take to the best table, and the evening progressed like a dream.
The old friend had done his homework. He had called two of his lady friends and described the possible evening to them. As he knew, they were good girls, and were happy to oblige.
So, as they were dining, the two girls approached and asked to join them. Our friend was a little disconcerted, but they were attractive, and he was feeling especially attractive, so there was little chance he would reject their request. They spent a wonderful evening with both girls treating him as if he was just another girl. It was great fun for all of them.
Afterwards, they all went out to the limo, and the old friend directed the driver to the best hotel in town. There they went upstairs, arm in arm, to a beautiful suite.
These were mature, thoughtful, progressive people all, so it wasn't long until they had chosen partners and were preparing to share some long looked for loving. Our friend was a little shy at first, but the lady who had virtually grabbed him in the room said, no worries, my friend. I understand. You were beautiful tonight and now I want to make love to you. But leave the clothes on. I'll only need to remove your pantyhose.
And she did. And proceeded to give him a great blow job, while she fingered herself. When he finally came, she drank it down and then sat on his still hard cock for a good, strong fuck. She was bi-sexual so all of this was mother's milk to her. She loved women, but she loved cock, and our friend filled both bills, so to speak.
At the same time the old friend was hammering his cock into the cunt of the other girl, not a first-time for either. In fact, it was a very joyous fuck-fest for all.
Afterwards, they squared themselves away, our friend again dressed perfectly as a lady, and all went down to the limo for the ride home. But it wasn't wasted. Much tonguing and kissing and loving went on in that limo. Finally, they dropped the ladies off, and the old friend escorted his crossdressing friend home. He escorted him to the door, gave him a goodnight kiss, and said, "Thanks for the memories, my friend."
Our next story concerns a woman who lived her whole adult life in men's clothes. This was a habit she had acquired while growing up on a horse farm, where everyone wore the most practical clothes, which happened at the time to be men's clothes. Her mother had passed so her father saw nothing wrong in it. She found them comfortable. So, when she went away to get her degree in agriculture she continued to wear the clothes she owned.
During college she matured and found that she didn't in the least care to have men groping her, whatever clothes she wore. She was drawn to the women around her, her female professors, her friends in the dormitory. She just loved the friendship of women.
But, she also found that some women were totally fascinated with her men's clothing. She became very popular among a certain set of women, who might themselves be girly and frilly.
It soon became the habit for one or another of these little women to knock on her door and ask her to go out to the local bar. She always went. She loved the company of women. And she loved to feel like she was as powerful, and as potent as a man.
And each week-end she proved this potency by taking on whatever girl she was with. She loved having her cunt sucked and licked, and loved having her small titties sucked. She was never disappointed. She also loved to cram as much of her hand as she could up the cunts of the girls she was with. If she could get the whole fist in it made her cum instantly.
Wearing men's clothes, she would take a girl or two out for, maybe even wearing a suit. But she loved the girl or girls to be frilly and soft. Then they would go back to the dorm and finger fuck, and suck, and use dildoes the way they were meant to be used, fucking pussy and ass without an unnecessary man present.
For the rest of her life she dressed as a man, and came to be treated as one by her friends, except in bed, of course.
Our next little story concerns what some would call transvestites. These were born male, but felt so much more comfortable dressed as women, the more flamboyantly, the better. One such "fellow" found the perfect job at a bar where the "girls" performed for the patrons, often lip-syncing to popular songs. From now on we'll just use the terms girl, or she, or woman. That makes it easier.
Our special friend in this story was a girl who loved to do her own performances, not lip-syncing but doing imitations of the goddesses of these girls; Madonna, Cher, Liza, and, of course Judy. She did it so well the clientele grew.
And she was never alone after the performances. If one of her compatriots didn't want to go out and have some fun, then a patron would. And every evening ended in the massive blow-jobs and cock-sucking they all loved. Our friend had learned early how to deep-throat, and she practiced it well on her lovers.
They weren't always as adept, but she had all the cock-sucking she could wish for. And she loved cumming so much that she often couldn't sleep unless she had shot her wad, whether with a lover or alone. She kept many toys in her room to play with when hungry for sex.
One thing though, it was always her choice. One night as she was leaving, a patron of the club, unknown to her, approached and demanded a blow job outside the stage-door.
"Fuck off, dip-shit," she exclaimed. He pushed her up against the wall. She took the little whistle each girl had hidden in her "bosom" and blew it as loud as she could. All of the transvestite girls swarmed out, and a major ass-whipping occurred that night. That patron licked his wounds and never showed his face again.
And our fine friend gained the glory she deserved from her fine performances at that very popular club, in a major city.
Finally, we are visiting a couple. A very unusual couple is some ways, but not so unusual in our times, one supposes. The man was small, and loved to dress as a girl, while his wife was tall and stalwart (the only word), and loved to dress as a man.
They were lucky enough to live in a large city where one can be what one is. And they took advantage of their luck. They were often seen together, walking the streets arm in arm, she being very solicitous of him, an he acting the part of the little lady. They were quite sweet in their own way.
They were a common sight in all the best restaurants, because they were wealthy. Even if he dressed like a frilly girl he was a prominent scientist, well-published, and acclaimed; and even if she dressed as a large man, she was a novelist of note, published all over the world and well remunerated.
But what of their sex life. They loved each other dearly, and surprisingly, he always took the lead in whatever sexual activities they enacted. In fact, in an odd way, he was a dominate and she was a submissive. But only behind closed doors. In public they played the typical roles of little lady and big man protector.
So their love life was one where he demanded her submission, took cock-sucking as worship, and whipped her buttocks and titties as he felt they needed. She in turn would let him fuck her first in the asshole, without lube, then into her pussy, loving every cock stroke. And neither ever failed to cum copiously.
She, of course, was always told to eat any cum on any body where she could find it. She did so, with gusto. Many a time she would lick his whole tiny body for hours on end, so much did she love him. And after each love-making he would always hold her large body with his small arms and show her how much he loved her.
So, as one can see, there are numerous ways to crossdress. None better that the other, just as no sexual acts are necessarily better that others. As long as we are all willing participants, and we are of age, it should all be one happy fuck-fest.
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