Newsgroups: alt.sex.stories
John and his wife had gone to a party at the home of Barbara, one of their friends. Barbara was tall and statuesque. A very striking divorcee who gave every indication of being eager for sexual activity. John had met her before his marriage at a time when his finance was living in another city. Barbara had come on strong at the time, but John hadn't responded.
The party had gone on for several hours and most people had left when John went upstairs to use the head. As was his habit, he quickly checked for evidence of stray feminine undergarments which he might fondle. None were in immediate evidence so he stepped into the bedroom and slipped open a drawer. John had done this routine sufficiently often so that he had a sixth sense for the location of the lingerie.
He was rewarded by the sight of satin and nylon in a profusion of colors and styles. As he had suspected, this was a woman who pampered herself with a delicate selection of panties and bras. As John had surmised from hugging Barbara whenever they met, (this was always an opportunity to make a cursory check of the type bra being worn). There was a selection of front and backhook bras. Most were very flimsy and delicate and there also were many with underwires to support her luscious breasts when she did not want them to jiggles. Some were demibra styles for wear with cleaving decolletage. Even better, they were 36-C which meant that they would be a perfect fit for Jacqui.
While the temptation to linger over this find was strong, John was emboldened to try another drawer. Again, his desires were realized when he found lacy slips and several garterbelts with real nylon stockings among the pantyhose. Needless to say, John was rapidily transported into ecstasy as he began to contemplate playing Jacqui with this treasure trove.
Unfortunately, his preoccupation was so complete that he failed to hear footsteps coming up the stairs and into the room. His first clue was when he heard Barbara's husky tone saying, "Well, can I infer that you prefer my lingerie to me? This will interest your wife and our friends."
John could only throw himself on Barbara's mercy, explaining about Jacqui and begging her not to disclose his secret yearning for feminine garments. "Very well she replied", indicating her long held contempt for all men which derived from her former husband's behavior in leaving her for a much younger woman. "I have always wanted a sissy male to serve me and you should fit the bill nicely. I will make you sorry that you intruded into my privacy and you can expect ample humiliation to be coming your way. I won't share this with your wife for now, but if you don't follow my instructions, you can bet your pantyclad ass she will find out about you quickly."
"Tell your wife that you must work next Saturday and be here at 9 a.m. Wear your bra and pink satin panties and be sure to bring along a waist cincher, garter belt, stockings, heels and a butt plug. I will begin your training as a humiliated sissy shemale. Don't ever expect the pleasure of wearing my feminine finery, although I may allow you to earn the privilege of worshipping it as a symbol of my superior body and your weakness.
Needless to say, John thought of Saturday with both fear and anticipation, knowing that he could indulge his love of lingerie, while at the same time he could be humiliated by this striking creature as she feminized him still further.
Getting out of the house already wearing his bra and panties was a problem because the bra was clearly visible through his shirt. However, he quickly got to his car without being seen by the neighbors. On the other end, he was not so lucky as he had to walk a distance. Of course he encountered a group of teenaged girls who were chatting and giggling with youthful exuberance. He could not avoid them and although it made him nervous he wanted to see the outlines of their brassieres, even though doing so increased his risk of exposure. How he envied their developing breasts, swelling inside lovely lacy bras.
Barbara greeted John by demanding that he demonstrate that he was wearing a bra and panties before she would let him enter her house. Although John was certain that the teenaged girls could be observing him, along with whoever else might be watching, he had no choice. He carefully raised the front of his shirt, trying to keep the back in place until Barbara could see the nylon and lace cups of his flimsy beige bra held snugly in place with y-straps.
Far from being satisfied, her only comment was, "And what else are you wearing? I want to see your pink little panties, now." John fumbled with his fly, but was informed that he was to open his belt and lower his trousers before he would be allowed the safety of having the door closed behind him. He could only comply.
Once she had him inside, Barbara instructed John to remove all of his masculine clothing which she then locked away in a trunk. Tying his hands behind him, she demanded that he present himself kneeling before her to pledge obedience to her superior female titties and pussy. She demeaned his pathetic little nipples and clitty-cock, reminding him that they were not worthy of the nylon and lace lingerie that he so coveted. However,she promised, in return for his devotion, to work on improving his worthiness.
John was then blind-folded and required to stand clad, only in bra, panties and heels, without moving until Barbara returned. After a few minutes, she returned to the room. To John's surprise she began to rub and squeeze his nipples. The effect on his cock was immediate. " Shall I take your panties down? 'Oh yes' "Yes is not acceptable, you will never address me except as 'Mistress'. "Yes Mistress, please." John felt the panties being slipped down to his knees.
Next he felt something being tied around his erect cock. When the blindfold was removed he saw a pink bow decorating his cock. Almost immediately there was a flash and he realized that Barbara had taken his picture. His erection quickly disappeared. "That, she announced, is for documentation of your journey and as further insurance of your continued obedience to my commands."
Pulling his panties up tightly wedged into the crack of his ass, Barbara untied Jacqui's hands and directed him to don the rest of his feminine attire. With trembling anticipation, Jacqui inserted rice-filled nylon bags into the cups of her 36-C brassiere, carefully adjusting the straps. The beige bra had been replaced with a black underwire with satin cups to cover the bra forms. Jacqui would have preferred a demi-bra, but pushup styles don't work well for shemales with pretend titties.
He often wore less sturdy bras which allowed his pretend titties to jiggle, but had decided that this was likely to be a situation requiring some restraint, especially if Mistress Barbara wanted to have him remove the bra forms so that she could administer nipple punishment (which, of course, Jacqui fervently hoped would be the case).
After requesting permission to remove the pink panties which Mistress Barbara had pulled up to cover his clitty-cock, Jacqui next forced himself into the black waist cincher to flatten his tummy and to shape his hips. He then fastened the red nylon garterbelt around his waist. Sitting on a stool, he drew each of his black nylons up his legs, attaching them carefully to the garters. In front, the garters stretched tauntly down his thighs, framing his pubic hair and flaccid cock. The back two suspenders curved over his buns. Jacqui then stepped into black leather pumps with three inch heels.
Finally, before pulling up her snug satin panties, Jacqui squatted down and inserted a gob of K-Y jelly, followed by a butt plug into her puckered little asshole. Squeezing her buns together to retain the buttplug, she stood and pulled her panties snugly over her buns. While the panties would help to hold her plug in place, Jacqui knew that she would have to keep her anal sphincter muscles tightly clasped around the plug and that doing so would remind her to maintain a more feminine posture.
When Jacqui had completed that task, she pulled on a short black half-slip which barely covered the tops of her stocking as she stood uncomfortably before Mistress Barbara, not knowing what was next. Jacqui hoped that her clitty-cock would behave and remain in a flaccid state. But, she knew that eventually it would demand attention and Jacqui was apprehensive about her Mistress' reaction.
CHAPTER 2
Well," Barbara chuckled, "I can't decide whether you look ridiculous, pathetic or cute." "I suppose you are a bit of each. Perhaps some make-up would improve your appearance, but I think that will have to wait until you earn it by taking care of my needs."
"Now that you are all dressed-up, we'll go outside so I can use the remainder of this film in natural light. We do want to have an adequate record of your progress." John was terrified because although he knew that the backyard was fenced, it was visible from the upstairs windows of adjoining houses. His terror was heightened when they got outside and he could hear voices from the next yard. But, he also knew that he had no choice but to cooperate.
"If you want to pretend that you are a woman, I'll want to see that your posture and gait are feminine. I don't want you to be an embarassment to we genetic girls who have real titties to jiggle when we walk and long shapely legs with well rounded buns for men to covet. Put some sway into your walk so I can decide whether you are sexy enough to excite my lesbian friends. Then perhaps we'll see whether horny men notice you when I put you on public display."
Jaqui, of course, had often practiced walking in heels. She loved the feel of tension in her calves when walking in heels, and adored the taut garters snugly holding her stockings to her thighs. When Jacqui walked, the butt plug wiggled, requiring strict attention to maintaining a tight grip with her pretend pussy. And,she had to keep her thighs tightly clasped to hold his clitty-cock and scrotum tucked away so that they would not create an unsightly bulge in Jacqui's panties. The result was short, mincing steps which displayed an exaggerated femininity, and provided a delicate bounce to Jacqui's pretend titties.
"Well," declared Barbara, "even though you walk like something is sticking up your ass, the effect isn't bad. Training you may not take as long as I anticipated. If I allow you to remove your butt plug, will you still be able to stand and walk like a sissy male doing an imitation of a real woman?" "Yes, Mistress," Jacqui replied. "Very well, you may remove it, but don't think that I'm finished with your little rosebud. If you want to have a pretend pussy, I'm going to have to stretch your little hole so it can accomodate my largest dildo."
"First, I want some more pictures. Sit demurely with your ankles crossed. Now, cross your hands across your breasts as though you were shielding them from prying male eyes trying to undress you. Lift your slip so I can capture your garter tabs and your bulging mound which is pretending to be labia. Now turn around and bend down so we can see your panty covered ass."
"Now trot inside, remove your plug before you get too excited and get yourself back here to me. If there is any evidence that you have relapsed and done naughty little boy things to your pathetic excuse for a pecker while you are out of my sight, you will be severely punished and our game will be over. I have more plans for you and they do not include your sexual gratification except under my control."
Keeping her tightly puckered asshole clasped around the buttplug, Jacqui teetered across the patio and quickly went to Barbara's powder room. Lowering her satin panties, and delicately lifting her slip, Jacqui expelled the buttplug, carefully wiping her asshole so that no lubricant dripping from her shemale pussy would stain her panties. She then pulled the panties snugly up into her crotch so that her clitty-cock would be held tightly out of sight and her scotal sac with its unfeminine balls retracted up into where her pussy would be if only she had one.
Jacqui then washed her smelly plug with hot water and soap and put it aside, wondering what was next in store. Jacqui didn't have long to wait as Barbara immediately summoned her with a brusque reminder that a Mistress must never be kept waiting.
"You really are a titless, pussyless wimp who needs to be chastized both for keeping me waiting, and for having the audacity to pretend that you have breasts and a vagina as though you were a real woman. You aren't anything but a flat chested sissy shemale. Take that padding out of your bra and get on your knees in front of me. I'll see if you can get erect nippples just as we ladies are expected to have when a man fondles us."
Jacqui immediately kneeled in front of Barbara who was seated in a lounge chair with her legs slightly spread and her miniskirt hiked up to mid-thigh. Her creamy white thighs were visible beyond the exposed tabs of her garters. She was wearing a gauze-like blouse through which the outline of her sheer lacy bra and the brown circles of her nipples were noticeable.
"All little boys believe that girls titties grow from being fondled and mauled. Do you believe that I can make your titties grow by playing with them?" "Oh yes, Mistress, please do", replied an ecstatic Jacqui. "You really are a foolish twit," replied the haughty Barbara. "You could't fill that bra even if you overdosed with hormones. What I will do is to make those nipples so sensitive that you will know how it is for a woman when her breasts are tender and distended because of the time of the month and some pig of a man has mauled them thinking that it felt good for her. "
"I know that is what you want, but first you must get me in the mood. You can start by licking my thighs, above my stockings, until you have your nose buried in my pubic hair and your tongue is licking my clitty. If you can keep your hands to yourself, and away from yourself, you will be allowed to suck my pussy for as long as I enjoy it. If you can get me hot enough so that my nipples push against my bra, I'll work on your pathetic titties until you beg me to fuck your sissy shemale ass. Now get started."
Jacqui was, of course, delighted at this opportunity to serve her Mistress who already had Jacqui in an absolute state of internal arousal and fighting hard to keep the excitement from causing her clitty to become noticeably tumescent. She quickly began licking the inner aspect of Barbara's thighs. It was no time at all before Jacqui's nose and lips were nuzzling Barbara's labia and tasting the moist nectar inside of her cunt.
Jacqui knew, that in spite of Barbara's seeming indifference, she was becoming aroused too. Not only was Barbara's pussy getting more and more moist, but Jacqui could sense the muscular quivers anticipatory to orgasm in a woman whose cunt was throbbing from the attention it was receiving. There were some telltale moans, as well.
Suddenly, however, Jacqui's head was pushed away from that delectable pulsing cunt so that her tongue was just out of reach of those luscious labia, and she was gripped between Barbara's powerful thighs. Simultaneously, Jacqui felt Barbara's long fingernails probing through the satiny fabric of her bra, raking across Jacqui's nipples. "Now, you sissy bitch," breathed Barbara, "you are about to experience the exquisite torment of nipple punishment and pleasure."
With that, Barbara pinched and rubbed Jacqui's nipples until the shemale was aroused almost beyond tolerance. Both Barbara and Jacqui were wracked with great orgasmic convulsions as wave after wave of release swept over them. The pressure of Barbara's thighs, the taste of her pussy on Jacqui's lips, the stimulation of her nipples, and the gentle friction of stockings and panties caressing her genitals were causing Jacqui to cum in the satiny panties even though no one had touched her clitty-cock.
She could feel the sticky exudate collecting in her crotch. It was warm and wonderful, and Jacqui knew she would still be horny after her satin panties had turned damp and sticky.
As they both lay exhausted, Barbara reclined in her chair and Jacqui kneeled on the ground awaiting further instruction from her Mistress. Barbara informed Jacqui that while she had made a good start, it would be necessary for Jacqui to exercise bettter self control during future sessions. "You may leave now. Change into the bra you wore when you arrived, but leave those panties on so that you will be reminded of how a woman feels when some man's cum is dripping from her cunt after she has been fucked. And, be back here at 9 next Saturday. I'll have some new adventures for us. You know the rules so dress accordingly."
"You also have an assignment. I expect you to spend at least one hour a day with that plug inserted deeply into your virgin asshole. I want it to be well dilated next week for you to feel what it is like to be be on the receiving end of a hard prick, or to wear a tampon as genetic girls must."
I alsoo expect you to be wearing a training bra. You don't deserve the luxury of satin cups, a firm underwire and delicate lace. I saw you admiring those teenage girls outside and I just know you were thinking about their cute little bras and panties. I'll bet you were wishing that your titties were growing just like theirs. Perhaps I should invite them in to show them how ridiculous you pathetic men are. They should be learning how to appreciate their soft downy pussies and tender young titties which are superior in every way to male bodies."
"I am going to give you more nipple training. Your pathetic pretend titties certainly need it. And one other thing, except for a sanitary belt and napkin to keep your butt plug in place, you are forbidden to wear any lingerie until you dress to come here next week. I don't want you getting aroused and wasting your cum. I have plans for every drop that you can store between now and your next training session."
"Oh Mistress," pleaded Jacqui, "please don't make me wear my bra when I leave here. I will wear my cum filled panties, but how can I get into the house wearing a bra without Mimi detecting it?"
"You should have thought about that before you went rummaging into my underwear and agreed to have me give you petticoat training, you pathetic pussy. You should be pleased that I am permitting you to wear it for a few more minutes. Remember, its going to be a long week before you are to be allowed the pleasure of a bra with the feeling of nylon and lace around your tiny nipple-buds, and that will be only a flimsy teen bra and not an exquisite creation of satin and lace which molds and caresses the breasts and nipples of a real woman."
"I will see you next week, and be prepared for more petticoat training. I want those nipples and that hole ready."
CHAPTER 3
Mimi had been asleep when John left the house that morning. He could only hope, as he drove home, that she would be distracted when he got home long enough for him to remove his bra and cum filled panties.
When he enterd the house, however, Mimi greated him with a smile and a hug. "My," she whispered as she traced her finger over the outline of his bra, "what is this?" Jake gasped and replied, "I felt sorry that I had to leave you this morning so I wanted to be thinking about your titties snuggled in your bra all day since I didn't have an opportunity to fondle them this morning."
Pushing John away, Mimi said softly, "Dont lie to me you sissy. You wore this bra all day because you wanted to pretend you had luscious tits like mine. Now drop your trousers so that I can see what you have under them. Have you been wearing my panties again?"
John knew she suspected something so he decided to respond directly, "You know that I'm wearing the panties that you had around your pussy and buns yesterday, dearest."
"I want to see them," insisted Mimi. "I want to be certain that you have't stretched them with a naughty erection."
With great trepidation, not knowing how accepting Mimi would be, John turned around and dropped his trousers so that Mimi could see his buns but not the damp stain in his crotch. "Turn around," Mimi demanded.
When John didn't respond, Mimi slapped his ass with her hand. "Barbara called me, and I know all about your day and what led up to it. She and I have discussed your behavior and training and I have decided to help her. I know that you have been wearing my panties without permission and stretching my bras by wearing them without my permission. I've found your cache of undies, your heels, buttplug and fantasy articles. I want you dressed in your sissy clothes now so that you can demonstrate what you have learned and I can determine how best to continue your training."
"It would be good punishment for you to follow Barbara's orders and not wear lingerie for a week. But, we have discussed a better arrangement. You will remain dressed as a sissy shemale, including a plug up your ass and a sanitary napkin, at all times in my presence. That way I can be sure that you are punished if your clitty gets hard and you are tempted to play with it. If you are not with me, you will wear male clothes, including baggy cotton underpants."
"Now," she continued, "take off those disgusting, soiled panties and that bra. Go to the bathroom and shave your legs and body including your balls. I want you to trim your pubic hair so it is nice and feminine. When you have removed all the ugly maleŠhair that you can reach, I will inspect you and shave your back."
Even though he was uncertain as to where this would all lead, John was excited and pleased, although hoping that his clitty-cock would behave. At least he would be able to continue to wear nylon panties and bras, even though he would have preferred real brassieres to a skimpy training bra. John had also long secretly fantasized about shaving his legs and trimming his pubic hair. He looked forward to smooth legs so that he could try stockings other that the dark ones he customarily wore to hide his shapely but hairy legs.
John quickly went to the bathroom, relieved that his secret was in the open. Although he was somewhat apprehensive about the future, he quickly decided that if he behaved, he could expect to be treated as a female and would have two real women with wonderful tits and pussys and a whole new supply of lingerie to adore. He stepped into the shower and began his transformation.
When he had finished shaving, including his face so that he would be smooth all over, Jacqui (for he was now feeling very feminine) shyly and demurely called to Mimi. She inspected him carefully and pronounced her satisfaction. Reaching into the vanity, she produced a large buttplug which she lubricated.
"It's time we got you accustomed to the experience of having an object inserted into your most intimate body cavity. Real women spend almost 25 per cent of their time wearing a tampon and are expected to accept male cocks at other times. Since you only have one pathetic hole, it will have to serve both functions. Until we can get you some tampons, a sanitary belt and pads to chafe between your thighs, and a dildo for me to use on you, this will do. Bend over so you can start to feel filled while I finish shaving you."
Jacqui obediently bent over, gratefully accepting the plug into her (for she was now ecstatically into her female self) puckered rosebud. She immediately and reflexively tightened her anal muscles and squeezed the buttplug with her buns so that it would remain in place. She then kneeled in the hard tub while Mimi shaved the remaining hair from her back.
"Now go to the bedroom and put on the pink panties and pink training bra that you will find there. Put on the white shorts and knit shirt and wear the low heeled shoes I have purchased for you. Then we are going shopping to buy sanitary supplies for you and a variety of dildoes for me to use in converting your tight asshole into a usable cunt for Barbara and me to use at our pleasure. We may find other uses for it as well."
"But Mimi," cried Jaqui, "I can't go out that way. Everyone will see the outline of my pink panties and bra, and what will they think of a man wearing heels?"
"In the first place," replied Mimi, "you will address me as Mistress, because that is what I am. I do not intend to permit my pussy-worshipping, sissy-slave to be on a first name basis with a superior female person. Second, you have always enjoyed secretly observing panty and bra outlines on real women. It is about time that you were the object of lewd and rude stares from men and women.
"If I hear one more word of argument, you will have some cute red polish for you fingernails and toes so that you will be even more obvious as a sissy. To make certain that you receive enough attention, you had better work at putting a seductive wiggle in your ass when you walk. Barbara tells me that your are skilled at wiggling your ass especially when your are busy trying to retain your tampon. Now get going. I am impatient to get you to the Mall where you can be seen."
Under Mimi's watchful eye, Jacqui went to the bedroom where she found the panties, bra and low heeled shoes laid out. Although she was disappointed to see that the panties were cotton rather than nylon, they were a feminine cut and their snug fit carerresed Jacqui's buns. The bra was nylon. It didn't really have defined cups, but only simple nylon triangles held together with thin elastic bands which Jacqui knew would not be nearly as enticing as the underwire bra with satin cups and a wide band that she preferred. The silky nylon did rub gently against Jacqui's nipples which were still erect and tender from Barbara's earlier teasing.
Mimi sensed Jacqui's reluctance to wear these plain garments, commenting "You will have to earn the right to wear truly feminine undergarments just as little girls must go through the uncertainty of waiting to see whether their little nipple buds will grow large enough to require sexy brassieres. Now get dressed."
"You will need some careful training before you get into nylon, satin and lace. We are prepared to share our female hormone pills with you. They won't give you wonderful titties like ours, but they will enlarge your breasts. Better still, your nipples will become engorged and sensitive just as ours do before our period. Then some nipple training will lead you to appreciate a real brassiere. Perhaps you need some silicone implants."
Jacqui dressed quickly for going out in public where everyone would know that he was not a real woman but a sissy- shemale as they noticed the outline of his feminine panties and his pink teen bra. Jacqui hoped that she would soon be allowed to make a more complete female appearance with real lingerie and makeup including nail polish and a wig.