A Sissy Boy is Madebylusty Vamp©
Gregory's torment was obvious to Jaclyn as she smirked wickedly, "I'll take that as a yes."
For the next couple of hours Jaclyn shopped for the female clothes that she fully intended to dress her bitch husband in. With Gregory at her side, Jaclyn shopped for panties, nylons, garter-belts and frilly little skirts for her new hubby. Jaclyn never missed an opportunity to let the female salesclerks know that her purchases were for her husband Gregory. Their giggles and condescending stares only contributed more to his growing arousal and subsequent pain. Knowing of Gregory's fetish for women's high-heeled shoes Jaclyn showed a rare streak of thoughtfulness when she allowed him to pick out his own feminine shoes. In spite of all women shoppers mulling around and blatantly staring at him, it took Gregory well over a half hour to make up his mind. Finally he settled on a pair of classic black patent-leather pumps with a six inch heel.
Back at their hotel suite Jaclyn forced Gregory to model his new clothes before she savagely took him in the ass again with her huge strap-on. Gregory had never cum as hard as he did that night. He couldn't understand it, but all he knew was those girly clothes made him feel so sexy for his big, beautiful, demanding wife and he loved that feeling. After that day, Gregory was always made to wear women's panties wherever he went.
The day the newlyweds returned from their honeymoon Jaclyn fired Gregory from his job. She took great joy in telling him that his only job from then on would be to please her, and that he would accomplish that by simply doing exactly as he was told. Soon Gregory was not only waiting on Jaclyn hand and foot while she was home, but also doing all the household chores including the laundry and the cooking.
Within a month of returning from their honeymoon Jaclyn had completely feminized Gregory. Around the house Gregory was, of course, required to wear female thong panties, with matching pink garter belt and stockings. Even though they had to be custom made to fit his size 13 foot, Jaclyn bought several pair of six inch "cum fuck me" high heels for Gregory to wear. Gregory was always required to remain bare chested since Jaclyn wanted him to be constantly reminded that he was nothing but a pathetic sissy boy. And, even though Gregory had a very light beard he was required to shave his face twice a day. His legs, arms and chest were also kept hair free as well as his ass and pubic area. The waxing of his ass to remove his hair was very painful and embarrassing to Gregory. So of course Jaclyn took great pleasure in taking him to the spa herself and watching as the girl performed her duty. Jaclyn had told the entire staff about him and they all wanted to see how he was locked up in his cage when he was being waxed. Jaclyn always let anyone come in if they wanted to see. This meant a constant stream of workers and customers were always there for his humiliation.
In addition to doing all the "bitch" work around the house Gregory found himself to be thought of as no more than Jaclyn's personal assistant or servant. He was made to dress her, bathe her and tend to all of her grooming needs. It wasn't long before Gregory was an expert at giving manicures and pedicures, as well as oil massages. Gregory found all these duties to be a gift, because he was able to be close to his true love.
Once Jaclyn had Gregory as her husband she decided there was no reason to hide the fact that she fucked other men. She told him they were men with real cocks. She also told him he should understand that a woman has needs, needs his little pee pee could never fill. She knew he would never object because the humiliation was exactly what he wanted.
On those occasions, Jaclyn would come home and announce she had a date. After serving her dinner, Gregory would be made to prepare her for that date. He had to lay out anything she wanted to wear, ironing it if need be. He would have to undress her and then dress her again. Usually she tortured him further by making him rub lotion all over her sexy, voluptuous body. Her attire was always very risqué when she went out, short skirts, tight low cut tops that showed plenty of skin, and always garter belt, nylons and very sexy high heels. This of course left Gregory in extreme pain because of his hard-on in his chastity device, which along with his ass plug had become a permanent part of his life since the marriage. Sometimes if she was feeling extremely sadistic, Jaclyn would tell him if he did a good job prepping her for her real man, she would let him prepare her pussy as well. This meant that just before she left, Gregory was made to kneel as she lifted her skirt and he would lather her already moist pussy with his tongue until it was literally dripping down her leg. Since she did not wear panties on her dates, this left the aroma of sex all about her as she went on her date. Gregory was left at home with a constantly hard and painful penis waiting for her to arrive home.
When she was dropped off, she would always look like she had just been rung out and hung up to dry. She loved being a slut for big cock. Over time he was trained for these returns. She would walk to the bedroom and without a word, Gregory would climb between her legs and clean all the cum left by her lover. He would clean it from her pussy, her ass and her tits. She loved having them cum on her big fat tits. It made her feel like such a sexy, dirty slut. After a while, she would announce that she was tired and kick him to the foot of the bed where he had a blanket that he slept under on top of the bed covers.
Sometimes when Jaclyn did not have a date and she was craving a big, thick cock, she would tell Gregory they were going out. He would prep her as if she was going on a date, and they would go to a local night spot together. Jaclyn would stand next to Gregory and openly flirt with men. She loved to tell them Gregory was her husband and how useless his little cock was. She would tell them she needed a real cock and Gregory could not provide it. Most men loved the ego boost and had no problem leaving with her and her pussy husband. Jaclyn always made Gregory drive them in their car to a hotel as they necked or she sucked the guys cock in the back seat. Then she would make Gregory register the three of them as she and her lover completely embarrassed him in front of the desk clerk. Then he was made to watch that lover fill all his wife's holes with that big fat cock. She loved to tell Gregory how good the guys cock felt as he rammed it in every orifice. Some of they guys even went along with Jaclyn when she asked if her pussy husband could suck his cock hard before he fucked her like a street whore. She loved watching her loving husband suck the monster cocks hard for her as she told him what a pathetic wimpy fagot he was for doing that so his wife could get some real cock.
Jaclyn always left her lovers cum for her pussy whipped husband to clean from her body. The more open minded men even made him clean their cocks after they were done with his wife. Gregory knew how pathetic he looked to these men, but he only cared that he was being a devoted husband to his beautiful wife.
About a year into their marriage Jaclyn was longing for a way to further humiliate her darling husband when she got a devilish idea. She purchased a tanning bed and had it delivered to the house. When she got home she explained to Gregory that she didn't like to see his bare chest with no color. So she told him she wanted him to spend ten minutes in the bed each morning to add some color to his white body.
Then she reached in a bag she was holding and said, "And when you tan, wear this, Babydoll." She held up a bra. "If you are going to dress like a fagot little girl, you should have the tan lines to back it up."
Gregory grabbed the bra. He noticed it was really small.
"It's a training bra." Jaclyn informed him. "You have tits like a little girl, you should wear what a little girl wears."
After about a week of tanning, Gregory had perfect little bra tan lines. It only added to his humiliation and degradation, especially when Jaclyn let her lovers see Gregory with his shirt off. It seemed no matter how much Jaclyn humiliated Gregory, she always found another even better way to add to it.
And so it was Gregory became a sissy boy.