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Screwing Married Men 2

The next evening I came home feeling irritable after an altogether unsatisfactory group session. Five men from a single men's club, Rotary or Kiwanis, I forget which, who'd signed up for severe discipline. They'd been slow to follow my orders, so I'd set them circle-fucking each other in a daisy chain, then I'd told them I was through, no more, they could go fuck themselves now that they knew how. Then they offered me double my fee to keep them on, pleading, and I was still annoyed with myself that I'd finally relented. But I was cheered when I saw Jim fondling a couple of nighties and a half-dozen new panties and bras while he cut off their price tags.

"Do they fit?" I asked.

"Yes, they're fine, thank you," he replied calmly. The Prozac at work! "The salesgirl insisted I try on each one and come out and show her, because they don't permit returns of lingerie, she said, once it's left the store. It was humiliating, all those women shoppers gathering to see. They looked amused. I was glad I had no body hair, or I'd have felt really ashamed. When I came out wearing this beige set they actually applauded." "I can see why," I said. "It's very pretty. It's hardly humiliating, wanting to wear pretty things. A nice choice."

I noticed that the house still reeked of perfume. He'd overdone splashing it on himself, probably, but I said nothing. I had to smile that now his "after shave" or whatever he imagined people thought he was wearing was as unmistakeably dainty and feminine as lipstick. My hubby in lingerie, wearing a woman's fragrance! What next? Obviously, lipstick was next. And eye make-up. A week later he was jerking off into some really filthy panties, brown-stained cum from someone's asshole, not mine, when his Mistress stroked some light cosmetics on him. Not much, just a touch of mascara and a little eye-liner, some shadow on his lids, and a mauve lipstick. I told him his face needed more drama, a more lively expression.

Of course he'd forgotten it was there by the time he returned to the bank. He was still wearing it, I saw, when he arrived home that evening and opened his Wall Street Journal to wait for dinner. That created a problem. Should I tell him? If so, how? Should I ignore it? If so, what would he think when he was getting ready for bed and stared into the bathroom mirror, and saw those stark eyes and that fashionably dark brown mouth? What had people thought at the bank, those who had seen him? Add in his perfume and they'd be sure that he was a transsexual or faggot coming out of the closet. Not untrue. I decided as usual to say nothing, in order to build his confidence that his increasingly feminine appearance was neither feminine nor noticeable. I commented only that he looked especially bright-eyed and alert, and asked if he been working out, or had gotten a raise at the bank, or what? He was bewildered but pleased. He knew what had really impressed me, and now he felt encouraged to keep it up on his own.

As he did. The following day was especially busy for me if boring, just straight fucks one after another. I arrived home tired -- after all, Loretta, how many times a day can a woman ride how many cocks to orgasm? Or douche and then get filled up yet again with more cum? But there was Jim, wearing fresh make-up! Wonderful! He'd actually bought it on his own, actually found the courage! And put it on, presentably enough. And worn it all day at the bank, so far as I knew in a sort of reversal of "The Emperor's New Clothes," thinking that it made him look better and yet remained invisible! I commented again on how alert he looked these days, and again he looked pleased. And this time he re-applied it before coming to bed. Does he do that at work, I wondered? Take out a compact and mascara and a tube of lipstick and freshen his face at his desk?

The next weeks were routine. Jim knelt naked except for his undies three times each week, smelling wonderfully feminine and looking prettily made up, trembling, sucking on my fingers and then receiving from my hand another pair of panties streaked with who-knows-what, the sacrament of his devotion. He'd kiss them and slip them on, then stroke cum into them if he could, attach a new brassiere around nipples he said had become quite sensitive, and after re-applying his make-up he'd leave with his old undies in a "Victoria's Secret" or "Frederick's of Hollywood" bag, once in a "Lady Madonna" bag my receptionist provided for the secretaries at his bank to marvel at.

A few months more and he was mine. If he hesitated to do my most trivial bidding I spoke to him harshly, and he was crushed. When I praised him, it was always for some utterly feminine trait or gesture. He blossomed and beamed whenever this happened, and tried even harder to please me. His breasts were budding, and I gave him strict orders to play with his nipples for at least fifteen minutes every day. This gave him so much pleasure, I saw at home, that sometimes he caressed himself unthinkingly -- if we were at a restaurant or otherwise in public I had to caution him not to. Gradually I weaned him away from soiled to fresh panties -- though I still had him cum each session into a sanitary napkin and then wear it for the rest of the day. He produced very little fluid, unless I said something to excite him, like praise for the way he'd plucked his eyebrows, or comment on his two-toned lipstick and lipliner. At home even the thought of sex ceased.

His accumulating bras and panties finally overwhelmed his bedroom bureau. I remarked one day that since he seemed to prefer them and they looked so nice, he should pack away his men's things to make more room for them. He did. The next day his Mistress scornfully informed him that since he was a woman, not a man, he should wear full lingerie all the time, not just bras and panties. A woman could not feel altogether neat and sweet and pretty and respectable unless she was wearing hosiery, pantyhose, teddies, slips, and now and then even a panty girdle. That he should begin thinking about shoes and outer garments too. He was old enough to be wearing heels, and to appear at least now and then in a dress! At home Jim asked me what I thought, and as always I answered without looking up, as if the issue were trivial, "Of course wear slips -- your dresses will hang better when you get around to wearing them. I don't know why you don't. And there are tailored suits for women as nice as those made for men. Skirts are much more lady-like. Of course if you wear a skirt to work you'll have to style your hair differently." So it was two against one. Jim began wearing full regalia under his business suits, and began to think about wearing a business suit with a skirt. He played with his hair, trying to make it curve coyly over his ears. My perfumed fairy princess was developing nicely.

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.

I started him on the other things he had to learn. How to apply full, persuasive makeup, even for sophisticated occasions. How to take care of his hairdo. Now that it was permed it was manageable -- I showed him how to put it up in rollers one evening, and he was delighted the next morning when he combed it out and found it was a beautiful mass of sculpted puffs and swirls. He had to learn feminine habits of walking and moving. I taught him to walk in heels with short steps, elbows close to his body, head high, hips swaying, his now quite noticeable breasts proudly thrust forward.

I began calling him "Jamie" instead of "Jim," because that was a woman's name and would help him remember -- and if he didn't believe he was now a woman, who would? I told him to appear more feminine when doing his domestic tasks at home, to wear a frilly apron over his skirt instead of the velvet slacks he sometimes favored. He was busier in the kitchen than I'd ever been, and was doing all of the cooking now. With practice his voice became thinner and took on a wider range of inflections. I still remember the first time he used the words "sweet" and "darling" and "precious" in a single sentence. He was describing a cute-looking movie star pictured in one of his women's magazines, and I was amused that he was referring with those words not to her appearance or her figure but to her matching skirt and sweater. Of course I still had a living to earn, and clients who needed my attention, and Jim still had his tri-weekly appointments with his Mistress. But now I could greatly accellerate his feminizing -- in fact it had to be completed, essentially, before he felt he should return to work. It turned out to be a lot easier than I'd expected.

iii.

Luckily I'd overcome Jim's prejudice against oral sex a few weeks earlier, almost by accident. For an appointment just before Jim's, I was wearing a slip-on rubber love-doll mask, sitting regally on an ornate, throne-like chair and allowing a client to lick my feet as if I were some kind of goddess. That was his thing. You know those masks with their own hair and big red oval lips set in an "O," and huge bimbo eyes? Gay men use them to hide their identities when they're sucking some stranger's cock, and wives in sex clubs use them sometimes when they'd rather not be recognized by whichever next-door neighbor they're fucking. My earlier client couldn't get off at all unless I wore the kind of blow-up doll mask his girl had once worn every afternoon while he mouth-fucked her behind the high school gymnasium. So that's what I wore. He'd worship my feet, then I'd lie back with my crotch over the edge of the throne and imperiously crook my finger at him. He'd crawl forward and then, half-standing, half-crouching apologetically, he'd fuck me. What some men need to do to get off!

This client had the thickest cock I have ever seen, Loretta. It was like a baseball bat. He always left my pussy swollen and stretched wide, and his spunk was a thick, viscous fluid he'd pump into me for what seemed forever. It took forever to ooze out, too, always in huge, phlegmy globs. Well, a few weeks before Jim's final phase began, with his enforced vacation, I happened to feel too sore and too lazy to bother using the bidet after my client left. I decided that it would be more comforting to have my cunt licked clean by my next client, my queenly husband Jim, who had once refused the honor as unsanitary. In he came wearing a red satin teddy, his breasts now grown out and filling his matching red bra like half-grapefruits, perfumed and made up, looking more like a butch lesbian than a man. As always he kneeled at my feet!

My face was still masked like a love-doll, my swollen cunt was beginning to leak blobs of thick sperm, and I knew it smelled strong, freshly fucked. I gave Jim my fingers to suck on as usual, but this time I first dipped them into the slime inside my pussy. I scooped up a huge gobbet of cloudy cum. Jim hesitated for only a second, but then licked it as devotedly as always. He must have realized what it was and been turned on by the humiliation, because after a few more fingers full, without my permission he lunged his mouth onto my crotch like some starved animal, and began to suck it out of me passionately. The way he thrust his face into me so was so primal I couldn't possibly think to punish him for it. He couldn't help himself, he was obviously out of control. And besides, it felt wonderful!

You know, Loretta, he slurped and sucked and swallowed cum from me for nearly his whole scheduled session. He was transported! It was as if the mask had rendered me more than human, an immortal fit for worship. He looked up at my face once or twice, and as the cute, wide-eyed, Bimbo "Oh!" expression stared back, he seemed reassured. His tongue curled and curved and probed and poked and reached deep into me! My desires rose up and I came in a beautifully blossoming orgasm, feeling as chaste as a wild flower the whole time, and then I rose up and came yet again! So sweetly gentle, yet so full, so complete! Tim's tongue in my pussy was like an armful of heather and roses, or like a young man shyly offering his best girl a bouquet of violets. And I was always sparkling clean when he finished. I wished we'd gotten into it years before!

Well, two days later I was again brim-filled with fluids and secretions from that same fat-cocked client, with my fairy husband again scheduled next on my calendar. I took off my mask so that this time I would appear to be what I was, Jim's familiar severe Mistress with her usual black dominatrix eyes and red slash of a mouth. But this time when Jim came in and knelt down humbly I simply stepped forward over him, mounted his upraised face, and pressed my spunky cunt against his nose and mouth. Then without a word I began to squeeze my cunt muscles. Thick mixed sperm and my own cum poured from my pussy into his mouth. All of everything my prior had squirted into me ended up in Jim, and when I stepped from his face with my cunt licked utterly pristine, he was still swallowing and licking the memory of it, eyes closed, in heaven! I decided that whatever else, from then on I would use Jim instead of a bidet to clean out whatever secretions and fluids there were in my pussy. At last I'd found his primary sexual talent!

By now Jim's breasts were more than ample, and he would fondle his nipples by the hour if I'd let him, a serene smile on his face. I do believe his character changed to match -- he became more sensitive, gentler, more tentative, sweeter. His face and figure grew softer, too. Understand, Loretta, Jim didn't want to be a woman at first, and he still didn't, really. He'd only had a panty fetish when I started with him, and I'd degraded him to do nearly anything to please his Mistress. Now here he was, wearing pantyhose, make-up, everything, quite presentably feminine, sucking a stranger's cum out of my cunt like any submissive husband of any whore of a wife anywhere. And loving it! That was his sex life now -- when he tried to jerk off nothing ever happened at all. When he pleased me, my little hubby, he was overjoyed that I rewarded him by making him my douchebag.