Tom's Emasculation
By: sissy cindy
Tom came home that fateful evening a defeated man. In spite of all the long hours he had put in, the dozens of nights he had settled for a few hours sleep on his office couch, the word had come down from the home office today... Tom would not be the new CEO, the job instead would go to a woman! Patricia Sommersby, to be exact. Sure, she had all the prerequisites for the position, Harvard MBA, Michigan Law, but then, so did Tom. And Tom was just not used to losing, not in anything. He always had to be the best, from his days of playground kickball to a middleweight golden gloves championship. Tom just did not know the meaning of defeat.
But that evening, he felt it from his head to his toes. His loving wife, Eileen had never seen him so hurt, so vulnerable. She fixed him a strong drink of a fine single malt scotch, and eased him into his favorite chair. She removed his shoes and loosened his tie and then got down on her knees and unzipped his pants. His cock was wilted and was the smallest she had ever seen it. Still, she gently licked and sucked it to life, and eventually he shuddered from a nice orgasm. Later that night, Eileen tucked Tom into bed, not caring that he had not made any efforts to give her any similar sexual relief.
Since Tom had lost the big race, he was terminated at Andrews Electronics, though not without a fat "golden parachute". He really had enough money to never work again, and for several weeks, that is precisely what he did. Most days he stayed in bed until lunchtime, and then lounged about the house, either in a bathrobe or some sweat pants and tee shirt. Eileen had never asked Tom for any help around the house, and he never offered any.
Eileen did not mind Tom's laziness so much, but she was very disturbed about what was happening to their sex life. Tom had always been a wonderful lover, despite a cock that measured five inches when fully aroused. But, this defeat seemed to knock the manhood right out of him. He was completely passive in bed, and Eileen was at her wit's end as to how to snap him out of it. Finally, she made a decision that would either bring her Tom back to her, or end their marriage, at least what was left of their marriage. With a long weekend coming up, Eileen decided to put her plan into action that evening.
In preparation for what she hoped would be a long night of hot love making, Eileen bathed in perfumed water, the bath oils making her already soft skin silky smooth to the touch. She applied her makeup in a seductive manner and put her hair up, to accent her gorgeous neckline, which led to her perfect 36c breasts. She wore a short night gown with a plunging neckline and matching lace panties. Finally she lit several candles around the bedroom and shut off the lights, striking a seductive pose when Tom finally came up to bed after watching television the entire evening.
"Wow, look at you, is this a special occasion or something?" he asked. "Could be this is your lucky night, sailor, you like what you see?" "God, you look fantastic Eileen, you really do, I just wish I were man enough to give you what you need." Tom looked down at his crotch, where his cock remained pitifully soft, in spite of the gorgeous temptress lying before him.
This was it for Eileen, the moment of truth. She had been talking to a therapist friend and reading everything she could about Tom's problem, which is not all that uncommon. She had already tried all of the more supportive types of therapy to help him regain his self esteem, and now she was down to her last hope, a form of tough love therapy that had been shown to work in a fairly large percentage of cases. However, it was going to take everything Eileen had within her to pull this off. She was going have to totally humiliate Tom until his sense of pride kicked back in and made her stop. When, and if that happened, Eileen prayed that Tom would understand and forgive her for what she was about to do...
"Hmmmmph, I guess you're right Tom, I don't know what I was thinking, you obviously don't have what it takes to satisfy a real woman. Hell, you couldn't even beat a woman out for the CEO job. You really are a pathetic excuse for a man. I don't know why it's taken me this long to realize it. All of my girlfriends have been telling me for years what a little pansy you are. Maybe you should call Ms. Somersby and ask if she could use an extra secretary. You do know how to type and make coffee, don't you Tommy? Hmmm, no Tommy won't do for a secretary, how about Tammy? That's a more appropriate name for a sissy, wouldn't you say, Tammy?
Tom stood before his wife's humiliating onslaught simply stunned. In the old days, his blood would be boiling and someone would be paying physically for this, though he would never harm a woman. No, in the old days, he would have gone down to some biker bar and and pretty much leveled the place. But these days, there was no fight in him, and her words just caused him to blush in shame.
"I asked you a question, Tammy, don't you think that Tammy is a more appropriate name for a sissy like you?" Tom just nodded, but Eileen would have none of that. "I want to hear you say it, sissy, what is your new name?" "Tttammy" came Tom's stuttered reply, his head bowed and tears trickling down his cheeks. "That's better, sissy, it's about time you stopped pretending to be a man and admitted what you really are, a tiny dicked little sissy girl. Now take off those sweat pants and sweat shirt, little sissies don't get to wear men's clothes!"
Tom trembled as he pulled the sweat pants and shirt off his body and stood naked before his beautiful, but suddenly demanding wife. "Now tell me, Tammy, what do little sissies wear to cover their privates?" "Underwear, I guess," mumbled Tom. "No, that's not right," corrected Eileen, "men and women wear underwear, but sissies wear something else. Now, I want you to tell me what sissies wear, Tammy, and I don't want anymore mumbling!"
Tom turned a deep shade of red, "panties is what sissies wear to cover their privates," he said in as clear a voice as he could manage. "Very good, Tammy, that's right, little sissies wear frilly panties to cover their tiny sissy cocks. Would little Tammy like some nice panties of her own to wear, so she can cover up her tiny thing?"
Tom didn't know what to say, why was his wife treating him like this? Why was she now asking if he wanted some panties to wear, what the hell was happening to him? A few months ago, he would have thought this was all a joke, and they would have had a good roll in the hay, especially looking like she did tonight. But now, he couldn't muster the courage to look his wife in the eyes, or move his hands from in front of his cock, which seemed to be almost pulling inside of himself, like a frightened turtle.
"Well, Tammy, do you want some panties or are you going to stand there covering yourself all night?" Eileen demanded. "I guess some panties would be okay, Eileen," Tom answered, not quite believing it was his own voice he was hearing. "No, Tammy, that is not how a sissy asks for things, and that is not how a sissy addresses her superiors. Now, you can start by getting on your knees with your head bowed."" Eileen waited until Tom had complied with her command.
"Now, when a sissy asks for anything, she must always remember to say pretty please, and she must sound very sincere. Also, when you address me from now on Tammy, I expect you to call me Miss Eileen, is that understood?" "Yes, Miss Eileen, I understand you, but, I don't understand why you want me to address you as Miss, when the proper title for a married woman is Mrs."
Eileen walked over to wear Tom was kneeling and put her warm hands on his cheeks, lifting his face to meet hers. "For nineteen years I have been so proud to be known as Mrs. Tom Sullivan, and one day I hope to be known as that again. But my husband Tom has left me, at least in spirit, and I will not besmirch his memory by pretending to be married to a sissy girl named Tammy. Is that clear enough for you, sissy, or should I get out my hairbrush to drive home the point?" "No, Miss Eileen, I understand you perfectly."
"Very well, Tammy, now, I believe there was something you wished to ask me?" "Yes, Miss Eileen, may I pretty please borrow a pair of panties to wear?" Tom cringed as he finished his request, hoping he had asked in the proper manner, and disgusted with his inability to stand up for himself.
Eileen patted Tom on the head. "That's a good polite little sissy. Yes, of course you may borrow some panties, Tammy, I think I have some nice frilly ones in the back of my lingerie drawer that I keep for special occasions, and what could be more special than my little sissy's first pair of panties!" Eileen then went to her dresser and began rummaging through her drawers, pulling out several pairs of lacy panties, along with some matching bras and garter belts, and a few pairs of stockings. Tom just kept his head bowed shamefully as Eileen would occasionally hold up a bra, or a pair of panties and giggle as she waived them in Tom's direction.
Returning to the bed, Eileen laid her selections neatly and then clapped her hands loudly. "Okay, Tammy, stand up and come over here. I thought since this will be the first time you have officially dressed as the sissy we both know you really are, I would let you decide what you will wear. Here you can see there is a nice pink bra and panty set with matching garter belt and even pink stockings; and here is a black merrywidow, with black seamed stocking and a thong bikini, verrrrrry sexy; finally, here is a yellow baby doll nightie, with white ruffles on the bottoms of the panties. No stockings to match, but, then it is almost bed time anyway, at least for little sissies like you."
Tom looked over the feminine attire, and finally selected the yellow baby dolls. He didn't know why, he just somehow felt they were the most appropriate for him. Eileen concurred with his selection, and did not mind telling him why. "Yes, Tammy, I knew you would go for the baby dolls. The other clothing would be something a real woman would want to wear, but, only a true sissy would pick a baby doll nightie with ruffled panties, like a little girl would wear to a slumber party. Say, that's an idea, let's have a slumber party! Oooh, I haven't had one of those since I was a teenager. It will be such fun, we can do each other's nails and hair! Too bad yours is still a little too boyish, but, I think I have something that can fix that. Here, let's get you into your nightie and I'll go get some pretty hair clips that will help your hair look pretty, okay, Tammy?"
Tom raised his arms and Eileen floated the frilly yellow nightie over his head, making sure his arms went through the thing straps and then pulled the nightie down over his chest. The hem of the nightie stopped right at his cock, leaving it temporarily exposed. Eileen then picked up the panties and held the waistband open for Tom to step in. "Come on, Tammy, don't be shy, let's get that ugly little thing covered up." Tom reluctantly placed one leg and then the other through the waist and the elastisized leg openings, and Eileen then reached down and pushed his puny cock head between his legs before pulling the panties up tightly to hold it there. When Tom looked down, it looked like he had a vagina, instead of a cock.
Eileen went into the bathroom and returned with two matching hairclips, in the shape of yellow bows. She then took a comb and parted Tom's hair down the middle, then uses the clips to hold the hair to either side. Next she took some blush and brushed Tom's cheeks to a pinkish glow, and then she made him purse his lips as she applied a bright red lipstick. "There, now you look like just the perfect little sissy, Tammy, why don't we go potty and then go to bed. I think I can find a use for that pretty little mouth of yours, even if I can't for that little thing in your panties."
Eileen led Tom by the hand to the bathroom and then made sure that he pulled down his panties and sat down to pee. After he was done, she had him wipe his little thing with tissue, as well as his bottom. Then, just to be on the safe side, she pulled out a Stayfree Maxipad from under the sink and undid the pink wrapper. She handed the maxipad to Tom. "Pull off the cover on the adhesive strip, Tammy, and then press the pad into the crotch of your panties. That way, we won't have any unsightly spots on your pretty panties." Tom did as instructed and pulled the panties up, now feeling the pad rubbing against his tucked in cock.
When Eileen and Tom returned to their bed, Eileen began kissing him passionately, pushing her tongue into his mouth. She ground her groin into his, her breathing quickening, she reached under his nightie and groped at his nipples. She worked her way down his body, licking and sucking on his small nipples, until they hardened to little nubs. Then she continued down to his panties, and began rubbing her face against the maxipad, feeling his cock swelling underneath. Then she roughly turned him over onto his stomach and got off the bed. He could not see what she was doing, but could hear drawers being opened, and buckles being fastened.
"Okay, sissy, it's time for you to find out what being a girl is all about, " Eileen whispered. "Lift that pretty bottom of yours baby, and I'll try to be gentle." Tom lifted his bottom up, as he felt Eileen pulling down his panties, exposing his virgin ass, while leaving the front of the panties covering his cock. Then Tom could feel something cold in his bottom, as Eileen pushed a big glob of ky jelly into him. Then she waited for a bit, letting the expectation build for Tom. "Here comes my nice big cock, Tammy, much bigger than that poor excuse you have been trying to pass off as one for all these years." In truth, Eileen had selected a small and thin dildo, not wanting to hurt Tom. It wasn't the pain she was seeking, it was his total humiliation.
Eileen pressed the tip of the dildo against Tom's sphincter, which, naturally was tightly constricted. "Come on, Tammy, open wide and get fucked like the sissy you are...come on, beg me to fuck you...now...let me hear you beg, like I taught you earlier."
The last thing Tom wanted was to have his ass fucked by his wife, but, his fear of losing her like he had seemingly lost everything else recently made her wishes impossible for him to resist. "Pretty please, Miss Eileen, will you fuck me in my sissy bottom?" The words had barely passed his lips, when Eileen rammed her dildo past his sphincter muscles and deep into his ass. "Very good sissy, if it's a fucking you want, it's a fucking you will get!" And, Eileen pushed her dildo in and out of him, faster and faster, the base of the dildo rubbing just right against her clitoris, causing her to get more excited with each thrust. Suprisingly to Tom, he found that he too was getting excited. The dildo was not really hurting him, and his wife was clearly getting near orgasm. He found himself panting like a girl, his cock now rubbing against the maxipad, and when he felt Eileen's body start to spasm from orgasm, his cock followed suit, squirting over and over again into the maxipad. They laid there, Eileen on top of Tom, panting and sweating for several minutes. Until Eileen finally pulled her dildo out of Tom's bottom, rolled off him, pulled his panties back up and patted his sissy bottom.
"You sure you haven't done this before, Tammy, you seemed to have enjoyed that as much as I did." Tom blushed because Eileen had spoken the truth, he did enjoy it, and now he was really confused. "Tell you what sissy, why don't you get down between my legs and taste a real woman, and while you are down there, give some thought about the rest of our lives. I'll give you a choice, you can continue to live with me as my sissy, Tammy, in which case I'll be getting you some maid's uniforms, and you'll be moving into your own room, so I can fuck a real man without disturbing your beauty sleep. Or, you can wake up tomorrow, as the man I married, and go out and kick the shit out of that bitch Sommersby and Andrews Electronics. Go out and fuck them, and then come back and fuck me, like I know you can! Let me know in the morning what you decide, in the meantime I want you to lick me until I can't take it anymore."
Tom tongued his wife's wet vagina tenderly to several orgasms. As she was about to nod off, he asked, "Ms. Eileen, may I pretty please change my maxipad, it's all sticky and yucky." Eileen just laughed, "fraid not sissy, I sleep like that at least four nights every month. Get used to it."
Tom did not sleep much that night...