Crossdresser Eats Guys Cum 5

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On a warm spring day on a Friday, I remember, his Mistress forced a crisis. She sent him to a boutique to buy a rather cute cocktail dress she'd seen, and a simple cotton frock to use as a house dress as well as a smart-looking woman's pin-striped suit, with pinched short jacket and straight skirt, for a day at the office. From then on he was her woman, she told him, and he would be dressed appropriately whenever he appeared for his tri-weekly sessions. Later on he would need to take a few weeks off to learn how to do it really right, and he would need to ask his wife's help. But for now all he had to do was appear to be a credible woman -- she would not tolerate a clown for a client.

Jim was proud of his new purchases. He kept them at Hospitality House in a Client's Closet for a time, and changed into them just before his sessions were scheduled, and then changed back. His Mistress sent him out onto the street now and then, so he could get used to people seeing him in women's clothes. With make-up and earrings, no one ever looked twice at him.

The Closet eventually filled to bursting, and under orders he carried everything home. That evening he put on a fashion show for his wife. I told him they were nice, but not being worn tastefully. That the cocktail dress and the suit needed heels, not the one pair of flats he owned. And -- as I again reminded him -- he needed a more sophisticated hairdo. And where were his accessories -- jewelry and purses and the like? When he told me he had none he was close to tears -- the hormones had made him much more sensitive to supposed rebukes. I told him I'd shop with him to get him started, but that if he meant to appear in public dressed like a woman all the time it would take a few weeks for him to learn everything he needed to know. Was he sure he wanted to look like a woman instead of a man? He nodded. I knew that what he really wanted was to please his Mistress, that he had private reservations, but we were reaching a critical point in his transformation now and it was no time to split hairs. That Friday was his last day in men's clothes, Loretta, and that Saturday was the birth day of that gentle blonde lady you see sitting over there reading and crocheting and smiling to herself now and then.

A near knockout dose of Thorazine the next morning, and Jim put on his house dress, and we went to a salon I sometimes use for certain customers, where they do feminine make-overs on husbands if wives request it, without feeling they have to ask if the man himself wants it. Four hours of electrolysis on his beard and chest (of many more the rest of that week), and meanwhile eyebrow plucking, body-waxing, ear-piercing, fingernail strengthening, lengthening, and painting, hair-permanenting, curling, frosting, and styling, a make-up consultation, and my Jim was way past the point of no return. As a man he'd been a pitiful drudge, but as a woman he was getting to be really attractive. You can see that for yourself now, of course! When we left he looked just charming, a lot like the way he looks now, Loretta, though not quite as lovely -- that came later, when he finally agreed to add to his disguise with facial plastic surgery. But I'm getting ahead of myself. There was just time enough before the Mall closed to get him a few pairs of shoes too -- heels and more flats. And a few blouses and skirts.

The next day he didn't recognize himself in the mirror and called out to me rather frightened. It took another really heavy dose of tranquillizers to calm him down, and really, I have to say, Loretta, he's been more or less cheered or zonked by one or another kind ever since. That Monday I had him phone in sick for the week, and claim his two-weeks vacation time as well, so he had three weeks before he'd have to face going to work looking the way he now looked. I shrugged when he worried the problem to me, as if no one would bother to notice that the man they knew was now a woman. I knew, as he didn't yet know, that his days of employment at the bank had ended.