He looked at the breast forms and shook his head slowly. They would fit his bra perfectly. His bra, he couldn’t believe that he had gotten used to saying "his bra". She had broken him in to the wearing of "his bra". She had broken him in to the bra, the panties, the stockings, the shaved legs, the women’s shoes. The painted toe nails and now she was adding the forms to the list of humiliations. He wanted to protest but didn’t, he had learned that to protest would only had time to his sentence in his chastity device.
It was the chastity device that started this whole thing for her and him. The degradation and the humiliating situations were a result of his wearing of the device. The device itself was simple enough. She had commissioned a friend to build it for her, he was amused at the request and she has kept him updated on her husband Jim’s progress. The Device consisted of a stainless steel tube that fitted over Jim’s penis. A ring just behind the head and at the base kept it from being able to slide off. The tube and the rings kept the poor penis from becoming erect. Another ring was fitted around the testicle sack, a small chain joined them and a tiny lock kept it all on. She had the key. He earned the right to wear the device by agreeing to do so. He walked into the whole thing with his eyes open. She had offered him his greatest fantasy, and he jumped at it.
They had played orgasm denial games with light bondage before; usually he had held her or lightly secured her wrists to the bedposts. He then would bring her close to orgasm two or three times with his hands before entering her then he would ride her for a few minutes until he huffed and puffed and spent his seaman. It was okay for her but no big deal. She had no idea that he was the one who desired the control, and she found that out by accident. She knew he masturbated in front of his computer, she hated it but didn’t know what to do about it. She assumed he was masturbating to porn sites that featured women in bondage, something she found repugnant. It came to a head one night when she wanted sex but Jim was unable to reach an erection. She knew he had been in the computer room that evening and had wasted his sexual energy looking at that screen, she was pissed. She did some snooping around in his computer and discovered that it was female domination and male chastity sites that he frequented. Jim wanted a woman to lock up his penis, my God! Further reading of letters supposed to be from wives and "key holders" extolled the virtues of a chaste male submissive. They were supposed to be very attentive and eager to please a women, they would give oral sex willingly, clean house, give pedicures and other personal care to their keepers. "I could learn to like that," she thought. When she presented the idea to Jim she couldn’t believe how quickly he went for it. Especially after she told him "you won’t be getting any sex anyway, you might as well live your dreams, my subbie hubbie".
It took her friend Don about two weeks to get the device right. Jim had to endure three humiliating fittings. Don and Jim’s wife, soon to be key holder, seemed to have a great time enjoying Jim’s emasculation. To Jim’s great embarrassment he seemed to enjoy it also. On the third visit the device stayed on. To celebrate Jim washed and waxed Don’s car then took Don and Jim’s wife out to dinner. Jim waited in the car while she and Don had a nice meal, Jim then paid with his credit card.
The penis remained restrained all week. Jim was very unhappy, she had said "we’ll do it for one week little one. Then we will let it out" but some mistakes and some anger on his part had added time to that. A week was over and he now had nine days more to go. That was the day she broke him to the decorative sheath and the testicle skirts. All it took was a two-day reduction in sentence time and he agreed. The sheath was a humiliating little bit of feminine fluff. Just a piece of vinyl lined with satin that laced its full length; there was a double row of lace at each end when worn the penis looked very small and dainty. "A girly little princess" she had called it. He had been instructed to call it that from now on. The Testicle skirts were no more than doll size skirts worn over the testicles, what would be the waist was up high on the sack the "balls" themselves were covered by the skirt. All in all she had successfully feminized Jim’s genitals. And since erection was impossible Jim was useless as a man. Jim’s girly little princess was let out thirteen days after the first belting. Don was there to ensure that she would be able to get Jim back into the device. Don hadn’t as yet seen the feminine little skirt and sheath Jim’s former manhood now sported. Don, bless his heart, introduced the collar to Jim and her. Don had purchased a large dog collar and mounted a ring in it. The ring could be at the front of the neck or the back of it. She could use the collar to attach a lead so she could lead Jim around or to help guide Jim’s head to wherever she wanted. Don smiled when he suggested that. But most importantly she could attach Jim’s hands to the ring, then when she removed the device it would be impossible for him to overcome her when reattachment time came around.
When she asked Don how Jim could masturbate with his hands clipped to his neck. Don said Jim would just have to rub against something, a foot, a pair of panties, the floor it didn’t matter. Jim would be so desperate he would find a way, and it would be fun to watch. Jim was released on a Sunday afternoon at 1:45 PM he would remain free until 7:00 he could have unlimited masturbatory freedom till his time was up. The only condition was that she or Don witness each ejaculation. When the penis was freed it erected immediately she had Jim remove her shoes with his clipped hands and use her feet to rub against for his penis for sexual pleasure. She and Don watched this disgusting display and ran a continuous string of comments about it. The remaining orgasms would have to be asked for. Jim would come to her, kneel and beg to ejaculate she thought that was a nice twist. Jim was kept naked the whole time. He ejaculated in a pair of panties, on a chair leg; a stocking and she did it for him the last time before it was tucked away. She and Don took Jim’s credit card and went to dinner while Jim pondered his fate. That was the night he was told she would begin breaking him into panties. Jim balked at the panty wearing he told her he would not wear her panties and he wanted out of the chastity device. She told him he would be wearing his own panties and the device would stay, in fact because of his little out burst it would stay on for three weeks. The denial of orgasm was difficult, doing without sex was difficult also but Jim hadn’t figured on what the denial of an erection would be like. God he wanted to get hard, to feel it, the weighty feel of a good hard penis, so manly, so strong he wanted to just get hard. He thought he could live without the sex or even the ejaculation but to not ever get hard, to never feel it swell, never to reach down and adjust it. Two weeks into his sentence she lopped three days of and began breaking him in to shaved legs. For the privilege of two additional hours out of the device she started breaking him into toe nail polish. She and Don had him dress in shorts, sandals and a tee shirt just a bit too small for him, dropped him off at a nail salon with instructions to "make them as red as red gets", they took his credit card and had a nice lunch while he did girl chat with the girl who gave him his first pedicure. He didn’t like it but nobody was going to see his toes, panties or shaved legs. When she broke him into stockings he was worried that someone would see when he crossed his legs. She smiled and said "two more weeks, or matching shoes, your choice" he chose shoes. That was a break in process. She had him buy women’s loafers in dark brown, black and tan and for fun a pair of red flats. His secretary noticed the shoes and hose; she just loved the shoes and wanted to know where he got them. She had been his secretary for ten years and felt safe in telling him that "she felt they were more like girlfriends now". It took a while to break him to girls shoes. The bra was next, worn at all times, he knew people would see it under his shirts. She walked over to the calendar took up her marker and he said, "may I please wear a bra?" "Of course you can wear a bra sweetheart, We’ll get you some today". Jim stood on the coffee table and turned around slowly so that she and Don could enjoy seeing how nice Jim now looked. His breasts had been referred to as "pert and perky and proud" Don sat with her on the couch his arm over her shoulder she had kicked off her shoes and placed her feet on the table her skirt had ridden up well past her knees the dark tops of her pantyhose were just visible. Jim couldn’t help but look at her legs. God he wanted to make love to her, to let his penis spring free, to feel it get hard, to feel it enter the velvety softness of her vagina. He wondered if Don was making love to her now. He knew they were good friends and had been since college. He wanted to ask her but was afraid of the answer as well as of making her mad. Don suggested that Jim might need to wear blouses now instead of men’s shirts, she agreed. "That would be ok wouldn’t it fluffy?" With a big smile he just said "yes." Jim would have to go to work wearing his new breasts. He wore them in a white bra with a cute little rose bud between the cups, over his darling bra he wore a white women’s button down shirt. The shirt was tucked into white women’s slacks with out pockets, worn with a narrow navy leather belt, navy microfiber loafers with a one and one half stacked heel, nude knee high stockings a red and navy women’s wide tie. Over the blouse he wore a navy blazer, his wife had transferred all his personal items, and a few, more to a small tan shoulder bag. He wore gold studs in his pierced ears, clear nails polish, a ladies watch and a gold tone bangle bracelet. His lips had been given just a touch of pink gloss, his cheeks a hint of color and his eyes a dose of mascara. He didn’t feel good about his looks at all. He looked like a sissy and he could no longer get hard. He sighed as he got into the passenger side of his wife’s car for the drive to work.
Work went surprisingly well, he kept his jacket on and seemed to go unnoticed, and by the time it was almost quitting time he was ready to breathe a little sigh of relief. Cheryl, Jim’s secretary came in to his office about fifteen minutes before time to go home with some papers for Jim to sign. While he was looking them over she said, "let’s have look at them cup cake." What are they about a B cup?" Jim’s jaw dropped my God she knows. "Stand up girl let’s see them". Jim stood, Cheryl smiled, and she reached over and untied Jim’s tie, unbuttoned four buttons of Jim’s blouse, retied the tie around Jim’s bare neck and turned it a little off center. She laid the collar of his shirt outside his jacket looked at her handiwork and nodded. She then reached into her pocket and took out a lipstick. Jim said "no". But she went ahead anyway and did Jim’s lips in red. She added blush to his cheeks, mascara to his eyes, said get your purse and follow me. Like a broken man he followed her out of his office. All the female office staff stood waiting in the work place. When Jim stepped out they stood and applauded, some gave him girlfriend hugs, they asked him about his shoes, his new breasts and those cute slacks. Jim and his new girlfriends all left the building together. One girl had engaged Jim in a conversation about handbags. Jim’s wife waited in the car for her feminized husband to appear when she saw the group of young ladies and her sissy approaching. She was delighted at this turn of events and saw it as an opportunity to further escalate her plans.
She sat in the chair that used to be his recliner. She was naked from the waist down Jim’s head was deep in her crotch; his hands cradled her buttocks. He had gotten very good at this task. He used his tongue in quick short darting stabs, then took long slow full length licks lifting her bottom and kissing the area between her anus and vagina, then he would move to the rosebud of her anus and use his tongue or nose to add to her pleasure. Back to her vagina he would suck and swallow any juices. She had already had three shuddering orgasms. He would bring her to one more hard one then bring her down slowly until she was back to earth. Without being told he would then drop to her feet and began a long slow foot and toe mouth massage finishing up with a foot and calf rub. He loved to serve her to feel her shudder under the ministrations of his tongue. He felt almost like a man when he serviced her this way. He always held the hope that she would allow him sexual intercourse. She hadn’t yet.
She patted his head when she wanted him up. He knelt in front of her, eyes looking at her beautiful feet. She spoke to him with kindness. "This is all very hard for you isn’t it sissy?" "Yes Mistress, I don’t even feel like a man anymore". "The girls at work think of me as one of them". "And Don has taken my place in our bed." "Oh sissy," she said "poor poor sissy, Don and I aren’t sleeping together, Don is gay, you silly girl." "And sissy I think you are cute and Don is very attracted to you and he likes men." Somehow that didn’t make Jim feel any better.
Don introduced prostate milking to Jim and her. He had Jim kneeling on the coffee table, a wad of tissues in his hand held in front of his bound penis. Don put on latex gloves took a gob of KY jelly and inserted two fingers into Jim’s rectum. Jim was suffering abject humiliation at this treatment. Then he began to ejaculate with out feeling it other than the feeling of having something in his butt and this dripping from his penis, his cheeks burned with shame. When Don pronounced the milking through, he gave Jim the soiled glove, and with a swat on his rear sent him to clean up. His wife decided that Jim could do his own millings from now on unless Don was around to help. To facilitate that she had a small ivory phallus that Jim could use to penetrate himself, and she brightly said "you can do it anytime you want, all you have to do is ask" Jim was too embarrassed to ask, for about two weeks when he finally did she was all smiles. Jim began to get small pleasure from his self-penetration and this added to his low self worth. Then it happened, Jim was moving the small ivory penis in and out one day when he had a magnificent orgasm. A great shuddering feminine orgasm. Jim had hit his G spot.
Jim was now hooked on anal stimulation he was embarrassed to keep asking her for the little dildo, but he needed this sex real bad.
Jim had just gotten home from running some errands for her. He had on a cute sundress with flat white sandals he was bare legged and had gotten a pedicure while he was out. She had done a little shopping herself while he was gone. When he came home she motioned him to the bedroom, striped him to bra, she clipped his hands to the collar and released his penis. She had him kneel on the bed head down, he felt the KY being applied. She tapped his shoulder and he turned to see her wearing a strap on dildo. With out a word she got behind him and mounted him. Before she was through she had thoroughly used him he had multiple orgasms, he had screamed and begged for more. When they left the bedroom he positively glided, her knelt at her side, kissed her shoes, suggested that he wear dresses to work. He gazed at her with the adoration of a puppy; She kissed his forehead and said "all broken in now"