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I want to thank Kelly Rodgers for her help in editing this story.
by A Happy Wife
He was marrying into money, but that didnt mean he didnt love her. He loved her very much, and had loved her very much even before he knew about the money. She was beautiful and carried herself with a style and grace that left him breathless. Plus, she was imposing. She had a confidence that was almost frightening to him, and she had always intimidated him. He felt he paled in her presence. And if she was overpowering to him, her mother was awe-inspiring. In her presence he literally was tongue-tied.
He first met Gloria, when he and Marsha had been dating for about three months. Marsha had pretty much reduced him to mush by then. He would have kissed her ass at noon on the fourth of July, on Main Street if she had just asked. He would have done it naked for Gloria. Both of these women were used to giving orders to men, and to having men hurry to please them, just for the honor of being near. Marsha had made it clear to him that she would be the lead player in their relationship and if he didnt toe the line she drew, he would be history.
Still, he wasnt expecting the opulence he found at the Windmore estate. It was apparent there was money here, and lots of it. He wasnt expecting the way Mr. Windmore looked either. When a man answered the door wearing black velvet ass-hugging slacks, a white silk shirt, and what looked to be a pair of black patent ladys flats on his feet, he didnt know what to think. The subtle, but unmistakable makeup threw him too.
Marsha kissed the man on the cheek and said, "Father, tell mother were here".
Mr. Windmore scurried off like a servant. Returning quickly, he said, "Ill show you in".
At the drawing room door, Mr. Windmore took Marshas coat and bag, and let them in. It looked as though Marshas father actually gave the woman in the room a small curtsy. Gloria Windmore rose to greet her daughter. Harold Windmore was ignored and made his way to the closet to put away Marshas things.
Gloria turned to Marshas latest and said "So this is your puppy? You call him Eve?"
Before he had a chance to correct her and tell her it was Everett she had ushered "Eve" and Marsha to a sofa. Gloria Windmore overwhelmed Eve and by the time the evening had ended, Eve knew he was in love with Marsha and just had to marry into this family.
They didnt see Mr. Windmore again until he stepped into the parlor to announce that dinner was ready. Mr. Windmores shoes click-clacked femininely as he led them to the dining room. Eve couldnt keep his eyes off those shoes as he followed Mr. Windmore and the two women down the hall. Gloria Windmore took a seat at the head of the table, Marsha took the other end and Everett, now and forevermore Eve, took the seat at the side of the table. There was no place set for Mr. Windmore. Instead, wearing a dainty tea apron, he served the meal. When he served, he stood feet together and bent forward at the waist. Then, when he stood, he would give a very delicate little curtsy. Mr. Windmores subservient behavior bothered Eve, but he didnt say anything. He did promise himself he would talk to Marsha about it as soon as they were alone.
Dinner was wonderful; he learned that Mr. Windmore had cooked dinner as well as serving it. He did join them for desert, perching delicately on the edge of his chair while he ate carefully. Then, he excused himself to clean up the kitchen.
Gloria suggested that the "men" could do the chores together. Eve never had time to respond because Marsha had immediately turned to the sideboard, opened a drawer, and pulled out a frilly apron. She had tied it around Eve before he could think of a way to object. Both the women smiled as Gloria fluffed the shoulder ruffles out and centered the huge bow in the back. "I just love a man who looks good in an apron," she said. Eve was ushered into the large kitchen to join Mr. Windmore in the chores.
Eve was definitely embarrassed to be wearing the apron and being unceremoniously dumped into this position of servant. Mr. Windmore said little and seemed worried and anxious when Eve tried to draw him into a gripe session. He put his beautifully manicured index finger to his lips in a be quiet gesture before pointing to a small camera in the corner of the room. My God, thought Eve, the room was bugged!
While Eve wondered why, Marsha and Gloria watched the two men working on the closed circuit television in the parlor. Gloria seemed to think that Eve was a good prospect for Marsha. Even though he was expressing some rebellion at being thrust into the maids role, he still had the apron on and was helping in the kitchen.
When their work was done Eve started to remove the apron, but Mr. Windmore stopped him, with a whispered "not yet." Mr. Windmore pressed a button near the door and stood feet together, hands at his sides. He motioned Eve to join him, Eve did, although he didnt know why. Both women entered the room and Mr. Windmore did his little curtsy thing once more. Instinctively, Eve started to join him, but managed to stop himself before he completed the act. Still, Marsha had noticed and gave him a disquieting smile.
When the inspection was over the women removed the aprons from their respective men and rewarded each one with a kiss on the cheek. The kiss seemed almost like a girl to girl kiss to Eve, who for some reason was finding himself extremely sexually excited. He was sure that when Marsha removed his apron his excitement was not lost on the women. In fact Gloria looked right at it and smiled. Marshas eyes followed her gaze but she looked somewhat upset about the obvious erection. Eve never wanted to have Marsha angry with him but hoped he would have the chance of using this very good erection later that night.
Mr. Windmore served coffee in the parlor and was then invited to join the group himself. He didnt say much, but he was always ready with a refill and a quick curtsy. At the evenings end, Marsha said "Betty, fetch my things" and to Eves shocked surprise, Mr. Windmore got up and almost ran to the closet for her bag and coat.
Marsha drove home that night and informed Eve that she was considering marrying him. She patted the seat beside her and he slid over and sat next to her as she drove. When they got to her apartment in the city, she gave him her purse to carry while she led him to her home and bed.
He had not yet made love to this woman, but had frequently imagined how he would seduce her and master her with his sex. But tonight the tables seemed to be turned. If anything it was totally her show. She stood and watched while he disrobed for her. She hefted his erect penis as if to size it up. It seemed to him that she was not impressed. He was really shocked when she slipped on a rubber glove and bent him forward. He felt the KY jelly and then her finger as it slid into him. He was absolutely red with shame as another finger entered his rectum, and greatly relieved when she discovered that he was too tight for a third. She gave him the soiled glove to dispose of.
When he returned, she pointed to the bed and said, "Get in." She went into the bathroom saying to herself, "way too tight, gotta do something about that."
She took him as though he was the girl. She road him three times, but when she wanted to mount him for a fourth, he couldnt get hard enough. Still, he was feeling pretty good about his performance until she said, "You must be nervous. Dont worry it happens to all men sometimes."
He was about to say, wait a minute I just did three in a row, when she slid up to his face and covered his mouth with her vagina. She was not shy about telling him exactly what she wanted. No, she instructed him in no uncertain terms, and even slapped his head around when he didnt respond quickly enough. By the time he had brought her to three very intense orgasms, he was rock hard once more and ready for that fourth time. She, however, just said, "men," and brought him off with her hand.
Not surprisingly, it took quite a while, and he ended up feeling like a little boy as she jacked him off while telling him how she would help him improve sexually, for him not to worry about his performance, and that she would help him to learn just what a woman needs. When he squirted, she said, "well it isnt much is it?" She gave him a box of tissues and rolled over and went to sleep.
In the morning she asked him to whip up some breakfast as she presented him with the apron he had worn the previous night. "Mother gave it to you. Isnt that sweet of her?" He wore the hated apron while he fixed her a nice breakfast. Then he cleaned the kitchen while she called her mother.
When he heard Marsha tell her mother, "Well he did have some trouble staying erect," his cheeks burned with embarrassment. He couldnt believe she was sharing his problem with Gloria. His problem? Hell, he didnt have any problem, he did it three times, and was ready to do it again when she masturbated him.
In spite of his problem the wedding plans were still on. He had moved into her apartment, and although they had separate bedrooms, there was plenty of sex. Well, there was plenty of sex for her. She insisted on oral sex and lots of it. She even had a small bell at her bedside and he was expected to hurry in to answer her call when she rang it. Often that call meant that he get his head between her legs and, "do the girl thing," as she called it.
Because of his "softness issue" she seldom allowed him to penetrate her. She said she was teaching him patience, and by keeping him waiting he had a better chance of reaching a full, firm erection. When she did allow him the pleasure of entering her. He would of course be so aroused that he would ejaculate very quickly and leave her unsatisfied. This new problem was cause for more concern and she once more talked it over with her mother.
Gloria visited them on a Tuesday evening. He served dinner wearing his frilly apron and the engagement ankle bracelet she had given him. He hated the anklet. It was very feminine and she insisted that he wear his shoes without socks when he had the anklet on. As his shoes would slop around on his feet without socks she had purchased some "house shoes" for him. These "house shoes" were black velvet with a feminine tassel on the vamp. He was sure that only a womans dressy flats would have the hard little heel and pointed toes that his shoes did.
He was so annoyed he had gotten sarcastic with her. "All I need with these is those tight black silk Capris of yours." When he served dinner to Marsha and Gloria he was wearing the Capris.
But Gloria liked them. "You look so sweet in your "pretty shoes and slacks," she cooed. Then she turned to Marsha and said, "Do you think his penchant for feminine clothing has any connection with his erection problems?"
He couldnt believe he was hearing this! What penchant? What erection problems? What the hell was going on? He was about to say something when he saw himself in the hall mirror. What could a small man in a frilly apron tied in a big bow, black silk capri pants and velvet flats, say? He couldnt think of a thing.
Several days later Gloria appeared at the apartment again. After sharing hugs, the women summoned Eve to the living room. He didnt like the looks of things. Marsha was crying; Gloria was comforting her and looked grim. "Eve" she said, "Marsha tells me you are having trouble satisfying her in bed. I hate to be so blunt but I want my daughter to experience a full and complete sex life."
Eve stammered around and was trying to figure out how to reply when Marsha beat him to it. "He didnt even try to go in me, he just used his tongue on me, it seems like thats all he wants to do. Oh mom, what am I going to do? Its like making love to a girl. Mom could you have a look at him, I know you havent practiced medicine in years, but could you please examine him please?"
Eve was about to die when Gloria turned to him and said, "Take your clothes off." Marsha looked at him and nodded. Then she got up and began undoing his apron and the back button and zipper on his Capris. When he was naked Gloria had him step up on a small table. She circled him and lifted his penis; she held his testicles and rolled them around in her hand. She shook her head and said to Marsha, "I can understand your disappointment, dear." Then with a dramatic sigh she said, "Well lets see if it works. Go on Eve, masturbate for us. NOW!"
Eve moved to get off the table but Gloria smacked his butt, telling him to stay where he was. Marsha moved in front of him and said, "do it girl, I know you know how."
Eve was furious. He was so mad he was having trouble maintaining his erection. The steady stream of put downs coming from Marsha and her mother didnt make it any easier.
Gloria said things like "my, he really has troubles doesnt he?" and "small and soft," and, "when he manages to become erect, is he very quick?"
Eventually Eve managed to get hard and was on the brink of ejaculating when Gloria said "thats enough Eve, I am sorry, but Ill have to help you." She gave him a small plastic cup and said, "Catch it in this dear." She bent him forward, slipped on a rubber glove, lubed it a little and inserted a finger up his rectum. Within a few moments he began to ejaculate.
Gloria turned to Marsha and said, "This is called milking. If he is unable to ejaculate he will need to be milked." Then she took the cup from Eve, looked at it and said, "Not much, is there? You know what, Marsha dear? I think that he has been masturbating on his own. He really should be controlled, at least until the wedding. Ill get something to help you with that dear." Then she turned to Eve, "Stand up Eve. Im not finished with you yet."
As Eve struggled upright, Gloria put a hand on his foot. "Marsha look at what pretty feet Eve has, his toes are so nicely shaped, he really needs to have his nails done. When were finished here you should send him to your salon for a manicure and a pedicure. In fact, while I finish here why dont you make the call and get him set up?"
Eve was dumbfounded, he was speechless, he had a hard enough time expressing himself around these two women under normal circumstances, but today things had reached a new level. They just overpowered him and took away all of his masculine resolve. He stood passively as Gloria continued to work. She took measurements of his private parts while Marsha made an appointment for him at her salon.
He heard Marsha giggle and say, "Sure, why the hell not? Make it the works". She turned to him and said, "you are in for a real treat, sweetheart, a manni, a peddi, a body and leg waxing, a perm, and best of all, a complete makeover!"
Eve had had enough. He started to object. But the women just laughed at how ridiculous he looked, standing naked on a table, his flaccid penis bobbing as he attempted to make demands. He just stopped in mid sentence and gaped at them as they laughed. He knew he had to accept his fate. He didnt have any choice.
The women were talking about what to do with his hair and nail color and which clothes would look "pretty" on him after the beauticians had worked their wonders. Marsha insisted he wear a pair of her bikini panties because he was getting a full leg waxing. To add to his already humiliated state she ordered him to wear a pair of her sandals, "so that you dont muss your toe nails."
So, dressed in pink satin panties "his" Capri's, a white tee, and "cute little white slides," Eve was off to the beauty shop. Because the Capris had no pockets, Marsha filled a small white purse with his things.
Gloria said she had to pick up a few things for Eves little problem and left Marsha to accompany Eve to the salon and get her squared away "with the other girls" before joining her mother for a little shopping. Eves eyes widened as he realized he was now one of the "other girls".
The salon was an ordeal of abject humiliation for Eve. When Sara, the manager, took her first look at Eve she just shook her head and said "Oh my". Eve just stood there as the stylists chatted with Marsha. Whatever they said must have been funny because Marsha and the young girls who would handle his transformation couldnt stop laughing.
Stripped to the panties and slides Eve was waxed right to his bikini line. Then his toenails were done in a red so bright Eve thought they had installed batteries in his toes. That was followed by silk wraps for his now long fingernails, and a very pearly pink polish with white tips.
"Very pretty", the girls all said as he was led to the shampoo and set area, his bright red toes on full and humiliating display to everyone in the salon. His hair was lightened, tipped and trimmed. It would be spiked after the perm. Once he was out from under the dryer his make over began. Just as the girls were putting the finishing touches on poor Eve, Marsha and Gloria burst into the salon with armloads of packages from a variety of very pricey womens stores. Eve just knew they were for him.
Marsha was going through bags and boxes, showing the girls the things she had gotten for Eve. Eve didnt like the looks of the goings on, especially when the salon girls were saying things like, "shell be so cute in that," or, "those are just darling." or, "Oh, I cant wait to see her in that!" Eve knew that the "her" they were talking about was "he," and adjectives like darling and adorable meant embarrassment for him.
Make up on, he was rushed into a dressing room with Marsha and Gloria. Once there, his panties were removed and his problem was once more tended to. Gloria opened a box and removed a plastic device and a tube of KY Jelly. The device was a pink, tapered, penis-shaped object with a recess near the base and a flange on the bottom. The function was obvious. It would go into his rectum and the recess would hold it in. It was a butt plug. Gloria was going to "plug him". She did so without ceremony. Bending him forward, she greased the plug and slid it in.
Much to his embarrassment he began to erect, something that didnt go unnoticed by the women. Gloria said, "tsk, tsk," and called out, "Sara, bring a strong rubber band, please ."
Sara came into the room without knocking, and seeing Eve, blurted out, "Oh my." Eve blushed all over.
Gloria took the rubber band, drew it back, and shot the end of the offending penis. Eve yelped in pain and surprise as his penis quickly softened; though it now sported an impressive red bruise. All three women agreed that the rubber band was an effective way to deal with "that."
But Gloria wasnt yet through. The next device was a curving stainless steel tube and a series of very thin chains. The tube slid over the penis and pointed it back between the Eves legs. A triangular, pink plastic codpiece went over the tube, and the chains held it all in place. Tracing the line of the chains around his hips and butt, a smiling Gloria told Eve that he would have a "panty line to be proud of. Of course," she went on, "youll have to sit to pee."
He haltingly asked how he would make "a poop," and after she stopped laughing at his infantile language, Gloria simply told him, "youll have to ask permission from your mistress, Marsha."
Marsha gave him back his panties and he was presented with his first bra. The bra was, he was told was, "just adorable, and just about the most girly thing ever." Once adjusted, the cups were filled with a full C-cup gel insert. Youll "just adore the jiggle," he was told.
As the now remarkably feminine Eve stood there, too stunned even to think, Marsha tapped the codpiece inside Eves panties with her fingernail. The shocks from the tapping went right through him and he felt his penis attempt to swell within the confines of the steel sheath. He groaned, the metal tube was going to be hell, and he knew it was to stay on until the wedding, at least.
"Walk for us sweetie I want you to feel something." Gloria said. He took about three steps and stopped. The plug in his rectum had three steel balls in its shaft. Those balls moved with each step, they banged together and sent sexual vibrations through his body. These were vibrations he had never experienced, and felt that no man should never experience such feelings. He burned with shame as he realized that the women knew exactly what he was feeling. The plug was uncomfortable, embarrassing; an intrusion - but it sexually excited him.
Gloria stood in front of him, demanding his attention. "Now that your little princess is all locked up, you have a new little buddy to keep you company. Lesson number one." She tapped the codpiece, "Whats this dear?"
"My little princess" he replied.
"And this?" she asked, as she tapped the base of the plug, sending the steel balls crashing into each other. He shuddered in both pleasure and humiliation, but answered, "My little buddy." Gloria nodded, satisfied.
Eve was handed a black half-slip and even though it seemed to be as girly as his bra, he was glad to have something to cover up his shameful plugging and forced chastity. Marsha pulled a pair of black one-strap slides from a bag. "Cant have you wearing my shoes, even though you like them," she said with a big smile.
He never said he liked them. He didnt like them. He didnt want to wear them, and he didnt want to wear the ones he had on his pretty feet right now. But he had put them on his feet without complaining and didnt resist the longish black skirt when they handed it to him. Being careful with his hair and makeup, he slipped the oversize pink silk sweater over his head just like they had requested. Marsha handed him a large black purse filled with various feminine items, including his new lipstick, mascara, and eye shadow, and a soft red leather womans wallet. Gloria held the door for him as he stepped into the salon.
Camera flashes went off and the salon staff applauded his entrance. Sara held a video camera to record his transformation. "Move around for the camera, pretty one," one of the girls shouted. Between the steel balls in his little buddy, the unyielding grip of the device around his little princess and the thrill of the attention the girls were giving him, he was light-headed, feeling things he had never felt before. The mixture of pleasure and humiliation was confusing but addicting.
(Then, he almost stumbled when he noticed Mr. Windmore standing next to Gloria. He was wearing a pink Chanel suit, and a matching bag hung from his wrist, which he held above his waist, his hand hanging limply down. Bettys blonde hair was fluffed and teased, and he was standing comfortably on high, spiked heels while Gloria held onto him possessively. He waved gaily to Eve, as if what they were doing was the most natural thing in the world.)
Then Marsha walked up to him and said, "Congratulations darling. Now you know the price of marrying me. In one month you will be Mr. Marsha Windmore."
A Happy Wife
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