Mark's Coerced Womanhood free porn video

Mark's Coerced Womanhood

by Denise C

Chapter 1: Mark and Emily

Mark's life was boring. After graduating from College, he found a job as a loan officer at a bank in Sacramento. An average looking guy, he was naturally shy and struggled at relationships with women. But five years later, he was doing well at the bank. Promotion seemed near and, if he could find the time, he was about ready to upgrade from his apartment to a small house. His sex life, however, was not as good. Mostly, it consisted of jerking off late at night, either to porn or the memory of some hot customer who came into the bank. Mark imagined that he was kinky. But his late night fantasies of anal sex, threesomes, and eating pussy were actually quite average compared to other guys. Of these three fantasies, he had only actually tried cunnilingus.

At this time, a coworker at the bank offered to set Mark up on a date with a friend, Emily. The match was an odd one. Whereas Mark was making $40K at the bank, Emily had just joined the faculty at the local college. She made twice as much as him and, to an outside observer, was much better looking than him. But Mark's friend thought that they might make a good match. Mark decided that he might as well give it a shot.

Emily was cute by any standards, but not most guy's idea of knockout. Dirty blond hair flowed to her shoulders. Her tits were firm, but not especially large. Standing only five foot three and weighing just 95 pounds, her body was as tight and athletic as when she played field hockey during her undergraduate days. Her ass was perfect, by far her best feature.

Like Mark, Emily had not had a serious relationship in a few years. While in graduate school, she had been burned by her ex-fiance. While away at a conference, he fucked a student from another school. Who knows how many times he had done it before? But this time, the sweet young thing didn't go away quietly. Having convinced herself that Gary would leave Emily for her, she began calling his office. When he didn't answer, she called the home and the jig was up. Emily dumped him and didn't date again until after she had finished her doctorate and moved to Sacramento. 

Mark and Emily did hit it off. They began to date somewhat frequently. Their dates were hardly exciting, mostly dinner or a movie, followed by a drink. Mark was taken with Emily. He initially thought her pretty, if not gorgeous. But as so often happens with infatuation, Mark's attraction turned to lust. Mark had immediately noticed her ass. Now, anal sex with Emily was a common jerk off fantasy. Likewise, Mark desperately wanted to taste Emily's cunt.

They continued to date, and soon, thought of themselves as boyfriend and girlfriend. Mark was happy to be dating and genuinely enjoyed their time together, but he had become frustrated with their lack of a sex life. Frankly, Emily was a prude. They had made out several times but Emily stopped him as soon as he tried to feel her tits. He didn't get her frigidness. It certainly wasn't religious. Like Mark, Emily was an atheist who enjoyed making wisecracks about Christians. Most likely, Emily had some type of self-esteem issue.

For Emily, her unwillingness to fuck Mark was all about Gary's betrayal. She just didn't feel like she could trust another man. But she did like Mark. And she had a way for it to work. It was radical, to the point that most people would describe it as perverted and sick. But she decided to offer it to Mark. He would probably run away, most guys would. But why not try? If Mark told anyone, he wouldn't be believed.

She asked Mark over to dinner. At first, things were like any other date. Emily then explained her history with Gary. Becoming emotional, she said that she just wasn't ready for another conventional relationship. And then she moved to her conditions to continue seeing him. She told him matter of factly, conveying near apathy as to whether he would agree to her demands or leave. She needed him to stay in a chastity device, with her having the only key, and she alone deciding when to let his cock out for release. He could ask for the key any time of course, but that would be the end of the relationship.

Her feigned indifference convinced him that she was serious. She told him that it wasn't a bondage kink. And that was true, at that time. She was simply unwilling to trust any boyfriend after Gary's betrayal. Plus, having been the passive partner in their sex life, she insisted on having things her way in her next relationship.

Emily told Mark that she didn't want an answer right away. Mark left the date, sure that it was over between him and Emily. What self respecting guy would give up his dick for a girl? Beyond that, he was sure that her asking was a certain sign of some underlying issues that he didn't want to go near. That night, he felt that he had dodged a bullet and didn't seriously consider acceding to Emily's demands.

But Mark had fallen for Emily and his mind started convincing itself that perhaps her demands were not bizarre, but instead no more perverse than anyone else's. He had spent many nights jerking off while imagining roughly fucking Emily in the ass or watching while she ate one of her cute friend's pussies. If he gave it a shot, then he could start fucking the woman he lusted after. He wasn't getting much action as it was and sex on Emily's terms seemed better than more lonely nights with a bottle of lube. He decided to talk to Emily to find out more details. Maybe if it sounded like she would offer release often, he would seriously consider it.

The conversation that followed offered Mark nothing. Emily gave Mark no assurances that he would be let out of the cage with any type of regularity. In fact, she was clear that she would probably want many nights where she received oral or a handjob, but he would get no satisfaction at all. And were he to complain about a lack of release, they would be done. She had to have the control of their sex life, there was no other way.

Mark's mind twisted the conversation. The idea of keeping his dick in a cage, which had seemed so creepy and bizarre, became more tolerable with familiarity. When Emily talked about him going down on her, he only heard the part about him finally tasting her cunt, not the part about him being expected to quietly accept receiving nothing in return. He imagined a wild sex life when she was clear that she could make no promises. Ultimately, Mark wanted to have Emily. He decided to give it a try.

Emily was surprised by Mark's decision. She had been serious that the chastity cage was the only way that she would keep seeing him. She was glad. She liked Mark, and wanted to keep dating. Plus, she really was excited about controlling their sex life. In her mind, the cage had nothing to do with dominating or humiliating Mark. But whether it was an innate desire, or a subconscious attempt at revenge on Gary, that seed was there. And although she didn't know it at the time, controlling Mark's manhood would allow it to flourish.

The next week went on as before. Emily and Mark didn't discuss the cage. They went on three dates. As always. they kissed, but Emily didn't even allow Mark to feel her tits through her sweater. On the third date, however, Emily bluntly told Mark that the cage had arrived.  Emily asked Mark if he was ready to start. Mark was again surprised by her matter of fact way. But he told her that he was ready. Emily asked him to stop by her apartment before her morning class. She also asked if he could come over the night after. Mark excitedly asked if they would be fucking. Irritated, Emily reminded Mark that she would make the decision about that and if he objected, then it wasn't too late to change his mind. For a moment, Mark thought that Emily had backed out. He apologized, but continued to believe that he was near finally having Emily.

Emily's morning class was at 10. Mark showed up at 9. Emily was was rushed and the caging of Mark's cock which followed was remarkable for its clinical and cold nature. Despite having never been naked in front of Emily, she had Mark undress. She then showed him the cage, a simple plastic trap no longer than 3 inches. Emily had no obvious reaction to seeing Mark naked, perhaps unsurprising since his dick was average in both length and width. She explained that the cage was designed to allow him to easily take a piss and that it was loose enough for him to keep it clean through ordinary showers. The device would not allow an erection. Being partially erect would be slightly uncomfortable. Not painful, but enough discomfort to prevent becoming completely hard.

Emily put the cage on Mark's dick and then locked it with a small pink lock. She smiled, said ``thank you'', then kissed him and said that she had to run.

Mark had about 36 hours before seeing Emily. The cage certainly took some getting used to.  At work, a vapid but hot college student came into the bank. While she spoke with  the manager for 20 minutes, Mark couldn't help but notice how her short shorts showed curvy legs all the way to her hips and her tight tee shirt flashed huge tits. As usual, Mark began to get slightly aroused. But the cage made sure that he didn't get erect. It wasn't painful, but he didn't like it. Whenever he needed to piss, he used a stall. He couldn't imagine the humiliation of a coworker seeing the cage.

That night, Mark first felt true frustration. Most nights, he jerked off before bed. Not tonight. It took a while for him to fall asleep, but he had no regrets. Tomorrow night, he hoped to cum inside of Emily.

That night, Emily was aroused knowing that Mark was wearing the cage halfway across town. She looked at the key, thinking how awkward it would be if she lost it and Mark had to get help freeing himself. She had chosen an expensive and very strong lock, and only an expert would be able to free Mark without the key. Emerging from the shower, she threw on an old tee shirt and a boring pair of panties. Reaching inside her underwear, she pinched the outer lips of her pussy tightly together and began slight circular movements. She thought of Mark's head between her legs. She loved cunnilingus but had not received it in nearly 3 years. That would change tomorrow. After 10 minutes, she dipped her index finger inside her soaked cunt and began to gently rub her clit. Now she was thinking of Mark's cage and how she, and only she, decided when he could cum. She was getting off on that control when she came.

The next day was Friday and Emily did not have to teach. After work, she began to dress for her date. She wanted to look hot. She put on a tight maroon dress that showed off her perky tits and tight ass. Although she rarely wore makeup, she did herself up with lip gloss and eyeliner. Underneath her dress, she wore black thigh high stockings, a lacy bra, but no panties. She shaved her light brown pubic hair into a perfect triangle and made sure that her pussy was smooth.

The date itself was ordinary, dinner at a second rate Italian place. After dinner, they returned to Emily's apartment. Mark was not initially disappointed. The previously prudish Emily had become aggressive and horny. She didn't complain when Mark finally felt her firm tits and rock hard nipples. She purred when he felt her pussy through her dress. The cage was uncomfortable, but Mark was sure that he would finally fuck Emily that night. Emily removed Mark's pants and shirt. She then asked, ``Can I see it?'' Mark was horny enough that he didn't feel embarrassment. He took off his boxers to reveal his semi-hard cock. But for the cage, he would have been rock hard. Emily looked at the caged cock, said nothing, but instead seductively slid her dress off over her head. Mark was startled by her lack of panties. Right before him was Emily's perfect pussy. As if he needed more convincing that this was a new, sexual Emily, she said ``I need you to eat me out.''

Mark needed no convincing. He grabbed Emily, roughly kissing her. Laying her on her back, she protested, ``No, I want to be on top.''  Emily prepared a pillow for Mark's head, and without further foreplay, provocatively sat astride his chest so that her cunt was less than a foot from from his face. Swaying her hips close enough to his face for him to smell her, she asked ``if you don't mind, I would like for this to take a while.''

Not waiting for an answer, Emily began to have her way with Mark's face. She wanted to be eaten right and she didn't hesitate to offer instructions. Emily didn't like hands or fingers while being eaten. She began by having Mark keep his tongue around her outer lips for several minutes. Mark didn't mind. Emily was dripping wet and Mark, who loved the taste of a woman, craved each drop that fell into his mouth. Emily then had Mark switch to long, slow strokes that extended from her opening to above her clit. When Emily was finally ready to cum, she told Mark to kiss her pussy like it was her mouth, with his tongue getting rough with the bottom of her clit. She arrived to the best cum in years and Mark excitedly awaited his turn.

But Emily had a different idea. ``I want to go again, but my clit is too sensitive. So probe my pussy with your tongue until I am ready to go again.'' Mark obeyed, and after about ten minutes, Emily was ready. She told Mark ``this time, just stick your tongue out. I want to fuck your face.'' Mark was in heaven. Emily, who last week wouldn't let him to second base, had become a depraved slut. If this was the way she was in bed, Mark imagined that she would be into things like anal and threeways.

After about 10 minutes of roughly riding Mark's face, Emily came again. But rather than turn her attention to Mark, Emily rolled off and haphazardly began to remove her bra and thigh highs. Mark was horrified. Emily really did have no intention of releasing him from his cage tonight. While Emily reverted from the slut of a minute prior back to the mousy girl of last week, Mark lied in tremendous frustration. ``That was wonderful,'' Emily said. ``Yeah, for you,'' Mark thought. Mark desperately wanted release, even if that was nothing more than jerking off. But he knew better than to complain, he suspected that Emily was testing him on this first night. Emily, naked and satisfied, quickly fell asleep. Mark, wearing only his cage, his face covered in Emily's juices, a constant turn on, lied awake in frustration.

The next day was hell for Mark. He loved eating pussy, and the memory of spending fifty minutes between the legs of the woman he lusted after was a constant source of arousal. Mark would have been glad to eat Emily for hours, all he wanted was a 10 minute fuck or blow job in exchange. He was frustrated by last night, but his memories of Emily's cunt assured that he would neither complain or ask for the key. Emily was to come over to his apartment tonight. Hopefully the test was over.

Saturday night was far more casual. Emily came over, dressed in well worn jeans and a plain green shirt, and they watched TV. It was a foregone conclusion that the night would end in Mark's bedroom. This time, Emily had Mark give her a handjob, the whole time providing clear instructions that mimicked how she pleasured herself. Emily then begin to kiss Mark. She kissed his chest, working her way down to his stomach. She then said ``I'm ready.'' At first, Mark thought that Emily was ready to unlock the cage. But to his great surprise, she instead climbed atop him, straddled his face, and again had him eat her to orgasm. After cumming, Emily told Mark ``I think we are nearing the time for you to cum.'' She then followed ``next time, I will bring the key.''

Emily decided not to spend the night. She told Mark that she would try to come over during the week, but that she would be stuck with work the the next few days. And despite giving the appearance of deviousness, she honestly had forgotten the key. She loved having sex again and was worried that perhaps she had pushed Mark too far. But she really did have to work, an editor was pushing her on a revision that, if accepted, would all but assure tenure at the college.

Emily dropped by Mark's the following Tuesday. This time, there was no date, they went straight to the sex. Emily again had Mark eat her pussy. But this time, she did bring the key. Mark's frustration had been intolerable, and otherwise, he may have ended the relationship. Freeing Mark from the cage, Emily began to give Mark a handjob. The reality was that Emily was not particularly adept at blowjobs or handjobs, but Mark did not care. After a minute, Emily proposed, `why don't we watch each other masterbate.'' Although this was far from his first choice, Mark just needed to cum. Emily turned on the lights and sat, spread eagle, about three feet from Mark so that their feet touched. Emily began to touch herself. She did her usual technique, but added some fingering, followed by tasting herself, mostly for Mark's benefit. Mark lasted about two minutes. He then sat, his drying cum on his stomach, for 15 minutes while Emily took her time.

Mark finally felt relief. Having cum, he began to feel ashamed at the events of the past week. Emily wisely waited for his hormones to recover. After an hour, she told Mark, ``its time to go back into the cage.'' Mark dreaded the cage. But his horniness had returned, and he did not object. Emily briefly rode his face as she maneuvered the cage on his dick, and then locked him away for who knows how long.

Chapter 2: Emily's Asshole

Their sex life continued in this manner for several months. Emily would uncage Mark about once a week for a quick fuck, blowjob, or handjob. Mark would only last a few minutes. He would spend several hours per week eating Emily. Mark was frustrated, but the weekly, if unpredictable releases, were enough to keep him in line. He was madly in love with Emily, and craved her body. Emily loved it. She truly liked Mark, and for the first time felt in control of her sex life.

In March, Emily was fucking Mark's face on a Thursday night at her apartment. She had no plans to uncage Mark that night. Then, by accident, Emily rode higher on Mark's face than usual and Mark's tongue unexpectedly found itself against her asshole. Emily noticed and liked the new sensation. She finished as usual, but later that night decided that she might like to experiment with some anal play.

The next night, they went to Emily's house after dinner and a movie. Over dinner, Emily came right out and told Mark that she planned on sucking his dick and swallowing his cum later that night. This was a change. Usually, Emily kept Mark guessing until the very end whether or not he would be released. But Emily wanted Mark pliant and horny for later that night.

After a shower, Emily dressed herself in her sluttiest lingerie, a corset and shamelessly revealing panties. She whispered to Mark how she couldn't wait to taste his cum. But, as usual, Mark would have to satisfy Emily first. Tonight, she crawled onto all fours, placing a pair of pillows under her stomach. Mark needed no prompting to start eating her out.

``Mark, would you do something for me?.'' Emily asked after about 2 minutes. ``Would you mind licking my asshole?'' Mark was taken aback. He had wanted Emily's asshole, fucking her in the ass was one of his biggest fantasies. But Emily wasn't offering that, she wanted him to use his tongue. Mark had not done this before, truthfully he had not given it any thought. But Mark's lust for Emily, and his desire for that blowjob, left no doubt. Without answering, he moved his tongue up and started making circles around her asshole.  Mark discovered that Emily's asshole tasted no different than her tits or thighs, and analingus soon became a common exercise.

Over time, Emily became more assertive about analingus. Sometimes, she would simply instruct Mark to ``eat my ass,'' and there was no doubt that he would comply. Eventually, she would come exclusively from Mark rimming her asshole, although this took far longer than having her pussy eaten, sometimes over an hour.

A month later, Emily asked Mark not simply to rim her ass, but to actually probe her ass with his tongue. He did so without compliant. A session a few nights later demonstrated how the relationship was changing Emily. Although Emily occasionally came from anal play alone, analingus had usually been as a compliment to pussy eating. Mark might eat her ass as foreplay, or he might rim her in between orgasms while her pussy was still too sensitive. But that night, Emily told Mark that she didn't want him to touch her pussy or do any rimming. All she wanted was for him to slide his tongue into her backdoor and keep it inside her. The resulting tactile sensation was pleasant but inadequate to bring Emily to climax. But 15 minutes later, Emily did cum. What got her off was not Mark's tongue, but the idea of having Mark perform such an extraordinarily intimate act.

Chapter 3: From Mark to Megan

Their relationship arrived at the one year mark. An unequal relationship changes both partners. For Emily, it was empowering. Her career took off. She received tenure and a fat raise, three years early. She was well on her way to becoming a leading scholar in her field. At home, she felt nothing of asking Mark to pleasure her, and forgot to feel any regret at keeping his manhood in its cage.

For Mark, however, the relationship was destructive. His performance at work suffered. He saw no opportunity at the bank and began to worry about losing his job. At home, he became increasingly submissive. He loved Emily, and as much as he would love to get rid of the cage, never dared ask.

Two dinner conversations then further changed the relationship. In November, Mark opened up to Emily about his troubles at work and his loathing of the bank. Emily suggested that he quit and move in with her. She would love to have somebody to take care of things around the house now that she was so busy at the college. Apparently oblivious to the irony currently caging his dick, he hesitated out of concern that, in essence, Emily was inviting him to become a male housekeeper. But he eventually accepted Emily's offer and moved in.

A new routine emerged. Emily would come home around five. After a quick shower, Mark would pour her a drink, Emily would sit down in her leather chair and Mark would eat her pussy. On these occasions, there rarely would be any anal play and Mark was never uncaged. Kinkier sex, perhaps 3 or 4 times per week, would wait until later in the night.

Moving in was good for Mark. It relieved him of the self loathing that had arisen as a result of career stagnation. While he had bouts of shame at being in such a dominated position, he remained in love and devoted to Emily. He wanted more orgasms, but once a week was enough to keep him in his place.

The second conversation occurred that December. Unusually, both Mark and Emily had too much to drink. Emily asked Mark if he had any dirty sexual fantasies. Sober, Mark would never have been forthcoming. And even drunk, he was too timid to mention his desire to fuck Emily's ass. But he did tell Emily about his fantasy of seeing her with another girl.

``Really,'' Emily replied. ``I have never really thought about that.'' The reality was different. In college Emily had kissed a few girls. But this was mainly to turn on boys, behavior that Emily now regretted. She thought it might to fun to make out with a girl and would probably let a girl go down on her, but she doubted that she would ever want to interact with another woman's pussy.

``I am just not sure how practical that is,'' she added. ``I mean, it isn't like there are a whole bunch of girls out there who are willing to do that, and it would be near impossible to find one who understood our situation.'' But who would you want to see me with?'' Mark mistakingly believed that Emily had left the door for a threesome open. ``What about Kara?'' Kara was one of Emily's grad students who Mark had met twice at college functions. She was the kind of girl that stoked guys' cliched naughty librarian fantasies. Bookish on the outside, she had a very sexy body. This was interesting. Emily was not going to sleep with one of her students, but she was having fun peering into Mark's private fantasies.  She asked, ``would you want to see her eat my pussy, or vice-versa?'' Mark replied, ``probably both,'' taken aback by Emily's bluntness. ``But if you had to choose one,'' Emily responded. Mark hesitated. Although it would be hot to see Kara go down on Emily, his real fantasy was to see Emily eat Kara. But it was hard, being the submissive partner, for him to ask Emily to do something outside her comfort zone. ``If I had to pick, I would see her go down on you,'' he lied.

``How about you,'' Mark then asked, seemingly oblivious to the carte blanche that he had just given Emily. Although Emily had not set out to do so, she immediately saw the chance to act on a recent fantasy. ``Don't you think it would be a lot of fun if we femmed you up for a night?'' Emily had seen a show on TV about couples where the male crossdresses. The new Emily found it really hot, although with Mark's recent change to housekeeper, she was reluctant to bring it up. But a few drinks and the revelation that Mark secretly fantasized about her lezzing out with a student emboldened her.

``Are you serious?'' Mark had no desire to crossdress. He had never expected Emily to bring it up. But Emily pushed, ``it would be a good way for both of us to have our fantasy. If you are dressed like a girl, it will be like girl-girl sex. Since we can't find a third girl, this is our best chance.'' Mark did not find this persuasive. She added ``don't worry if other people would find it weird. Nobody has to know, and with what we have, we should do this type of thing.'' And then Emily added the clincher, ``would you do it for my birthday?''

Psychologically, Mark was no longer able to say no. He didn't agree that night, but Emily persisted, and he gave in a few days later. Emily's birthday was only a few weeks away, shortly after the new year. She played it well. The initial expectation had been that Mark might put on a dress and panties late at night, and they would have sex. But Emily talked about how much fun it would be for Mark to spend the whole day as a girl, complete with makeup, jewelry, and slutty lingerie. Gradually, Emily built it up to a full day of crossdressing.

Although Emily's fantasy had not originally been overwhelming, actually being able to live it out made it so. Mark was eight inches taller than her, and fifty pounds heavier. She had to shop for his outfits. She reveled in buying dresses, blouses, skirts, and most of all, lingerie. By her birthday, she had enough girl clothes for a week.

``Are you ready,'' an excited Emily asked the morning of her birthday. Mark had dreaded this day, but Emily had cleverly suggested that, as a girl, Mark might be allowed out of his cage for an extended period of time. Emily handed Mark a pricey pink woman's razor. ``Let's start by having you shave.''  Despite having never discussed this, Mark acquiesced. Mark assumed that Emily wanted him to shave his legs as well as his face. But Emily wanted him to shave everything except his head and eyebrows. She triumphantly stood outside the shower as he complied. Mark didn't like shaving his privates, but Emily insisted.

Even though it was winter, Emily wanted to dress Mark in a summery outfit. Despite her preference for thongs, Emily chose a more practical pair of pink frilly panties that held his dick in place. She next chose black garters and stockings. She then pulled out a C cup black bra, ``since we need to use padding anyway, I thought I would go big.'' Sitting on the bed in womens' underwear, Mark felt great shame. As Emily showed him the brown and white sundress he was to wear, he thought about asking for the key. But with great timing, Emily added ``we are going to have some really hot lesbian sex.'' Mark put the dress on. Emily then added a simple necklace, a nice bracelet, and a little makeup.

Emily thought it would be really hot to refer to Mark as ``Megan'' for the rest of the day. But she sensed reluctance and didn't want to push things too far. Unlike Mark, she planned on doing this many more times. Emily had planned a girls day in, complete with chick flicks and girly drinks.

Emily made sure that the sex was special. When mid afternoon arrived, she grabbed Mark's leg and said ``I want us to go eat each other out.'' Mark's initial discomfort was quieted by Emily's unusually adept blowjob. Mark was not allowed to keep the cage off, but Emily did let him cum in both her mouth and pussy, the first and only time he had ever had her twice in a day. All told, Mark ate Emily to orgasm 6 times that day, including a marathon session of deep analingus.

Emily insisted that Mark sleep as a girl, wearing a frilly pink nightgown with a matching set of panties. Emily told Mark that she wanted to do this again. And she played her trump card, making it clear that femming up meant more sex.

As is so often the case, familiarity reduced the discomfort of doing something originally seen as perverted. Mark never had a chance to resist a repeat performance. First, Saturdays became girl-girl day. And Emily made sure that Mark was always satisfied. After a month, Emily demanded ``Megan, eat my pussy.'' And things continued, with Saturdays now known as Megan days.

Emily used the cage to its full effect. While at first, Megan days offered extra uncagings, after a few months, Emily made it clear that while Megan was was always to be freed, Mark would never be uncaged. So Megan days became twice a week, and then three days a week. Eventually Emily announced that Megan could only cum once a week. But she made it clear that she still expected Megan three, and then four, and then five days a week.

At the two year mark, Megan only owned four pairs of male clothes. They were worn exclusively for errands outside the house or, less often, visits by family members. Emily had purchased an impressive amount of dresses  and lingerie for Megan. Megan wasn't to dress like one of Emily's sloppy undergrads. When she came home from work, she expected to receive head from a girl with some class. At Emily's insistence, Megan grew her hair long. When leaving the house, she was allowed to style it as a ponytail, allowing Megan a futile attempt to reassert her lost masculinity.

Chapter 4: Megan's Humiliation

Nobody was able to look in on Emily and Megan's relationship. Were a professional able to observe it, they would have found the change in Emily stunning. Initially, Emily's psychological irregularities were not much greater than the average adult. Her ultimatum regarding the cage had been quite out of character. But in the intervening years, Emily had been removed from all the influences that ordinarily keep a character weakness from developing into a true mental pathology. At work, she was the rising star of her department. She was in a position of authority not just over her students, but over her colleagues as well. At home, Megan's increasing submissiveness added more and more fuel to Emily's growing dominance. There was nobody in Emily's life in a position to enforce social and sexual norms. Two years ago, Emily would have found the thought of pressuring a boyfriend to live a women unfathomable. But now, it was a huge turn on. She was no longer healthy, indeed she was a control freak of the highest order. And this pathology was showing signs of developing into sadism.

Just as Megan's willingness fueled Emily's dominance, Emily's increasingly extreme and perverted demands pushed Megan to greater submission. She genuinely enjoyed the lengthy stretches of oral sex that Emily expected and found pleasuring Emily's asshole to be a major turn on. The crossdressing wasn't her kink, but she largely learned to accept it. There were some exceptions. Around three o'clock, with the house clean, and Megan waiting for Emily to come home, the old Mark sometimes seemed to return to the back of Megan's mind. Here she was, her cock in a chastity cage, wearing a skirt, bra and panties, with nothing to do but wait until Emily was ready for her to orally service her. But despite these odd bouts of self doubt, Megan was not unhappy at this time.

Emily now got off on pushing Megan's boundaries, and then erasing them. That September, Emily initiated two new humiliations. Unlike the cage, the analingus, or the feminization, Emily felt no need to strategize. She simply told Megan what she wanted her to do. The first humiliation was a collection of ten outfits that Emily expected Megan to wear on weekdays while Emily was at the college. Most were French Maids outfits with high heals, collars, and absurdly short skirts. At best, they looked like Halloween costumes, at worst, Megan was made to resemble a cheap whore. Another outfit was a fairy costume that Emily found in a catalog. Dressed head to toe in schoolgirl pink, Megan cried the first day she wore it as soon as Emily left for work. But she made sure to pull herself together in time for Emily's five o'clock orgasm, and she never considered taking it off before then.

The next humiliation was more elaborate. In November, Emily had Megan make an elaborate three course dinner to celebrate Emily's appointment to Full Professor. Near dessert, Emily said, ``Megan, there is something, something sexual, that I need you to do for me. I am not sure that you are going to like it, at least the first time, but it is important.'' Emily had Megan shower and then go into the bedroom. As usual, Megan shaved all her hair except her head. On the bed, intended for Megan, was an elaborate corset, but no panties. After putting the corset on, Emily instructed Megan to get on all fours. ``For this, I am going to tie you up.'' Emily revealed a pair of handcuffs that she used to pin Megan's arms behind her back. Emily then attached a collar to Megan's neck, which she then secured to the foot of the bed. Finally, Emily removed her thong panties. Placing them in Megan's mouth, she attached a ball gag to keep her quiet. ``This will be hard, but you will learn to like it.''

Emily then disappeared into the bathroom. Three minutes later she emerged. Emily was naked with the exception of a plastic cock protruding from her pubic area. The strapon was not overly large. Her intent was to fully possess Megan, not injure her.

Megan was shocked. Emily had never indicated a desire to peg her. Emily came to Megan and removed her cage. Working fast, she quickly brought Megan to orgasm via handjob. ``I'll be back in 10 minutes. And when I am done, you will never be able to think of yourself as a man again.''The handjob was cruel. Horny, Megan would have been able to mix her dread with some sexual excitement. But with her hormones low, Megan was only afraid. But, in bondage, she had no recourse. Emily was going to return, and she was going to receive anal sex. And Emily was right, if Megan was to assume the woman's role in bed, any future claims to masculinity would run hollow. A tear swelled and fell to the sheets.

After 15 minutes, Emily returned. ``This is going to be so hot. Real women get fucked, you must be so ready.'' Emily applied some lube to Megan's asshole and the strapon. Eventually, Emily expected Megan's mouth to supply the only lube, but that would take time. Megan felt the dildo against her hole. Emily began to work the strapon into Megan's asshole. It took two full minutes, but she managed to insert the strapon to its hilt.

Emily fully enjoyed fucking Megan. She soon realized that she wouldn't be able to cum this way, but it was a thrill to ram the cock in and out of Megan's ass. Megan experienced far less enjoyment. The assfucking hurt, for sure, but the humiliation was worse. She had been turned into a complete sissy. Emily owned her and they both know that Megan would comply with whatever sexual command Emily issued.

Emily fucked Megan for about 15 minutes. Finally, Emily had to get some relief. She untied Megan. Tears caused Megan's mascara to run down her face. ``I am going to sit on your face. I want you to alternate between my pussy and asshole. Stay away from my clit until I tell you, I don't want to cum too soon.''

The strapon then became a weekly event. It began to define an abusive relationship. Megan liked servicing Emily's asshole and she learned to accept her feminization, but she never leaned to like the strapon. She, in fact, dreaded it. Sometimes, Emily would tell Megan in the morning that she was going to ``take her ass,'' or fuck her brains out'' later that night. These days were the hardest for Megan. But Emily thought that Megan was no different than so many new brides in history, anxiously awaiting a penetration that she was powerless to stop. Emily chose not to focus on getting Megan to take larger dildos. Instead, her new fantasy became having Megan deepthroat the strapon, and then take it to the hilt without additional lubrication. The first time Emily tried to penetrate Megan in this way, Megan cried like a baby. After 4 months, it finally worked.

The relationship continued in this way until Emily and Megan celebrated their fourth anniversary. That night, Megan ate Emily's cunt and ass to orgasm 4 times. Exhausted, Emily neglected to unlock Megan's cage. It had been one month since Megan last came, and then she was only allowed to jerk off on the condition that she swallow her own cum. Megan thought about asking for release but chose not to for fear that Emily might then decide to bring out her strapon.

Chapter 5: The Ultimatum

For a year, Emily had been working with a coauthor named Anna. Anna was five years older than Emily and a star of the highest order. Whereas Emily was undersized and athletic, Anna was tall, thin, and curvy. She was also a confirmed lesbian. In June, Emily had to fly to Seattle to finish a new paper with Anna. Since meeting at a conference, Anna had desired Emily. Her lithe and fit body had been the subject of many late night fantasies.

At their previous meetings, Anna had engaged in some low level flirtation with Emily, who had not noticed. Now Anna decided to go all out and seduce Emily. After a long day of grinding out tedious revisions, Anna invited Emily to her home for drinks. There, Anna asked Emily outrageously forward questions about her sex life, ``had she ever been with a woman?'', ``how often did she masterbate?'' Emily had a clear choice to make, either sever the relationship with Anna, or fuck her. Anna was certainly attractive and she wouldn't mind kissing and feeling each other up over their dresses. But she was pretty sure that Anna would want much more and she had plenty of misgivings about trying pussy that night.

Ultimately, Emily resolved to do the right thing. Her relationship with Anna was just too lucrative to her career.  Anna had a pipeline to the top journals and continued co-authorship might allow Emily to publish her way to an elite school. Maybe Anna would be content with a handjob.

So Emily and Anna fucked that night. And the next two. As she suspected, sleeping with Anna required that she eat pussy. She didn't really like it, but she learned to tolerate it. At least Anna was far more adept at oral sex than Megan. Although Anna clearly wanted Emily to eat her asshole, Emily felt confident that she could hold her off.

After returning home, Emily and Megan continued as before. Anna now routinely asked Emily if they could mutually masterbate over Skype. Emily was uncomfortable doing that at work, and didn't really care for watching Anna, but agreed for career reasons.

Three months later, Emily and Anna again met for work in Seattle. A day full of writing was followed by sex. To her surprise, Emily was OK with eating Anna's cunt. Anna continued to position her asshole near Emily's mouth in the hopes that Emily would comply, but Emily expertly shied away. Anna was too timid to just ask. If she had, Emily had decided to suck it up and eat her ass.

On her last day in Seattle, Anna opened up to Emily. ``I love you, Emily. I want to marry you. Lets go to New York, get married. I can get you a tenured position here.'' Emily had serious reservations. She really liked Anna as a friend, but there was not a true sexual attraction. She liked what Anna did to her pussy, but she was unsure about reciprocating. She didn't mind eating Anna out now, but what about in 20 years? Plus, marriage meant that she would have to publicly live as a lesbian. She equivocated and told Anna she would think about it.

On the flight home, Emily decided to marry Anna. Her career had to come first. More importantly, she did want to get married. She was already 30 after all. She hated the thought of leaving Megan, but she decided that was fine if she gave her some cash to get restarted. That first night back, she had some of kinkiest sex yet with Megan. Emily knew the end was near and she wanted to relish the end of a fruitful relationship. She had Megan eat her pussy three times, and her ass twice. She fucked Megan with a bigger strapon that she purchased earlier, but had not yet unwrapped. Megan cried. Emily came.

The next morning, Emily told Megan about Anna. Megan was despondent. She begged Emily to stay. She asked Emily what would she have to do to keep her. Megan's pleading hit Emily hard. She realized that with Megan, she was the dominant partner. She had everything she wanted sexually and never had to do anything she found off-putting. Professionally, Sacramento was not Seattle, but she had it pretty good. With Anna, she would not be the dominant partner and she would have to do things in bed that she didn't like. She told Megan that she would think about it and went for a walk through the neighborhood.

When she returned, she gave Megan her take it or leave it demands. They were extreme.

1. Megan would legally change her name from Mark to Megan.

2. Megan would come to Las Vegas with Emily and they would get married. Megan would wear a very traditional wedding dress.

3. Emily was welcome to have affairs that helped her career.

4. They would start spending summers away from the heat of Sacramento. On these trips, Megan would bring no male clothes and would openly live as a woman.

5. Megan would receive breast implants to allow her to become a B cup. When family visited, Megan could dress as a man and bind her tits.

6. Megan would forever remain submissive and compliant in bed.

7. Emily's new fantasy was to try watersports. Megan would engage wholeheartedly. Emily would be allowed to piss on Megan and Megan would drink Emily's piss if asked.

8. Megan's cock would be released exactly six more times. Each time, she would be allowed to jerk off. After her sixth orgasm, the key would be thrown into the garbage.

9. After her last release, Megan would make a serious effort to learn to orgasm exclusively through receptive anal sex. No other type of orgasm would be allowed.

Megan was horrified. If she agreed, she would cross a threshold of deviancy from which she doubted that she could return. The pissing disgusted her. She asked Emily, ``how often would you want to do, you know, bathroom things?'' Emily replied ``I don't know. It might be once a year. Or I might really get into it and expect you to act basically as my toilet. That is all I can tell you. But if you say yes, you accept the latter possibility and I expect you to honor that without complaint.'' Oddly, the permanent incarceration of her dick hardly registered with Megan. She was only freed every month or two anyway by this point, and she had become conditioned to focus exclusively on pleasing Emily.

Megan was torn. Emotionally, she needed Emily. She was now badly psychologically damaged and only an appalling set of demands offered any chance of freeing herself from Emily's sick orbit. But with the leverage of Anna's proposal, Emily now dared make such a proposition. Part of Emily realized that the relationship had become abusive and that Emily's demands were twisted. In a few minutes, she changed her mind six or seven times. ``Can I think about it?'' she finally asked. Emily replied, ``you have one hour.''

Emily left for another walk. Megan ran her left hand through her French braid and sighed. Struggling, she nervously played with the hem of her skirt. She still didn't know what she would decide.

Part II: The Good Wife

Chapter 6: Real Womanhood

Sipping a hot cup of coffee, Megan drifted over to the kitchen window. It was only October, but hard frosts came early here in Montana. After Emily left for the college, Megan had spent over an hour on her routine. Waxing a part of her body daily, doing her long hair; it took work  stay a passable female. It would be a boring day. Megan did not have to start dinner for 6 more hours and the house was in good order. She fondled the hem of her maid's outfit, wondering how to pass the time before beginning the weekday routine of making dinner, waiting on Emily, pouring her a drink, and dropping to her knees to give her her early evening head.

It had been six years since she agreed to Emily's demands. Things now were stable. Megan had settled in as a housewife. Emily had accepted a job at a college in Montana. It wasn't as prestigious as Sacramento, but Emily was the star of the place. Megan had pretty much fallen out of touch with her family. There wasn't much to do except keep Emily pleased and herself pretty.

On good days, Megan thought about the happy times. First among these was her wedding day. Even though it was a rare occasion where outsiders saw Megan in her full womanhood, she felt no humiliation at all. In fact, she soaked up her wedding with as much enthusiasm as a girl who spent her entire childhood dreaming about the big day. Any guy that saw her would be foolish not to do the same thing if it meant getting a wife like Emily. And he only had eyes for one woman so the giggles of the women who watched didn't bother her.

Emily hired two call girls to act as witnesses and help Megan get ready. It took five hours, there would be no shortcuts. Every part of Megan's body was waxed. Padding would not do, Emily needed glued on tits when she took her vows. As the hookers helped Megan into her bridal lingerie and gown, she even looked forward to the certain assfucking she would take later that night. While it would surely hurt. it would mark the moment when she became all Emily's.

On other days, Megan thought of the degradations that she accepted to be with Emily. And while there were frequent small humiliations, Megan had plenty of time to remember about the big ones. On this cold fall morning, her mind drifted back to one of the first in Montana.

Megan's New Tits

Having married in Las Vegas, the time quickly came for Emily to insist that Megan get her tits done. Emily hated the fake tits that she saw in porn movies, often calling them ``water balloons.'' So the plan was for Megan to become a B cup, small but perky and natural looking. Emily wanted to make sure, however, that they would be big enough to render wearing a bra a necessity. If the first operation didn't work to this effect, then they would allow some time for Megan's skin to stretch out and then further augment her tits. Stretch marks and scars were not allowed. Megan was nervous, this was to be her most substantial step toward womanhood.

The first two doctors that they saw sensed that something was wrong and refused to do the procedure. Finally, they managed to locate a surgeon in Seattle who was happy to accept their money without worrying about any inconvenient ethical issues. Emily and the doctor gathered around a computer screen looking at generated images of how different sizes and implant types would look on Megan as she sat naked on the examination table. Emily was wearing a gray wool skirt without any underwear. Megan noticed a thin stream of vaginal secretions flowing down her leg as she selected Megan's new tits.

The operation and recovery were unremarkable. And the new tits had their effect. They were there all the time to remind Megan of her newfound femininity. And they represented the end of Megan's cross dressing and the real beginning of her time as a woman. The tits were not huge, but they looked real and served their purpose. Megan would not need more surgery.

Megan Learns to Seduce Emily

True to her word, Megan's cage came off exactly six more times. On none of those occasions did Emily even look at Megan's dick. Instead, having taken Emily's strapon, Megan was allowed to jerk off once Emily had left the room. On their wedding night, Emily led Megan in her gown to the top of the hotel. With a lump in her throat, Megan then acceded to Emily's demand that she throw the key, the only key, from the top of the hotel. Later that night, between a session of cunnilingus and another of analingus, Emily took care to fill the lock with super glue. If the cage was ever going to come off now, it would take a skilled locksmith.

Prior to the wedding, Megan had taken Emily's strapon about twice a week. In the immediate aftermath of marrying, Emily penetrated her most days. The goal was to train Megan to cum from anal sex. And it took time. Most days, it didn't happen. Eventually, Megan learned to concentrate and sometimes, after 30-40 minutes, the prostate message managed to pay off. Megan needed the occasional release, but it wasn't an overall enjoyable experience. She found anal sex somewhat painful and quite degrading. It was an awfully big price to pay for a quick orgasm.

A few months after the wedding, Megan abruptly returned to the old schedule of 2-3 weekly ass fuckings each lasting about 15 minutes. These were for her benefit. She got off on taking Megan's ass, but after a short while grew bored and preferred to have Megan's tongue working her own ass or pussy. Megan needed much longer to cum and the time since her last orgasm quickly mounted.

After a month, Megan had become badly frustrated and the benefit of release exceeded the cost of a hard 40 minute pounding. She finally asked Emily, ``tonight, can you do me until I cum.'' Looking at Megan, Emily replied. ``I was wondering when you would ask. And to be honest, something has been bothering me. I feel like I should not have to take the lead on this. If you want to cum, then it is only fair that you come on to me.''

``What do you want me to do?'' asked Megan. She was surprised, she thought that she was a good wife and didn't think that Emily had any complaints about her effort in bed. Emily then said ``when a girl wants a good fucking, she has to be seductive. Dress up in something special. Tell me how bad you want my cock in your mouth. Tell me how you want my cock to make you feel like a real girl. I want to be surprised when you do something unexpected and feminine.'' Megan was taken aback. ``I couldn't say that. I still feel awkward about being so girly.'' ``Suit yourself,'' said Emily. She then returned to her reading. Megan would not cum that night.

Emily had made her price clear. Megan would have to debase herself in order to obtain release. 2 more weeks passed and Megan was ready to explode. As Emily showered, she dressed herself in an elaborate red corset with the skimpiest panties that would hide her cock and thigh-high red stockings. Her needed to cum and was finally ready to give in. Emily smiled when she saw Megan, ``you look like a naughty girl tonight.'' They began to kiss, Emily naked and Megan dressed like a Nevada whore. Emily asked ``is there something you want me to do.'' ``Go get your strapon'' Megan replied. Emily chose her biggest dildo, average girth and seven inches long. She made Megan connect the device to her hips. After a few minutes, Emily told Megan, ``tell me how bad you want to suck my dick like a real girl.'' But Megan couldn't do it. She had believed that her feminization was all about making Emily happy. In her mind, that made her a good wife. Now Emily wanted her to act like a real sissy. After an awkward minute of silence, Emily crawled onto all fours. ``That is too bad. You made me really hot and I need to cum. Eat my ass until I cum and get your tongue as far in me as you can.'' What followed was one of Megan's lowest moments. Tears flowing down her face, Megan worked Emily's ass. It took her a long time to cum from analingus alone and this was no exception. 35 minutes later, Emily came.

Three times over the next two weeks, Megan resolved to seduce Emily only to back out at the last minute. Then her frustration reached the point where she was committed to following through. Then, Emily rejected Megan on several nights. First, dressing in her lingerie wasn't seductive enough for Emily. So Megan ordered new lingerie for the occasion. Again, not good enough. Emily made it clear that for her to cum, Megan had to do something special, unexpected, and girly. ``I am tired of always doing the pushing. I want you to help yourself become more of a woman.''

After three months, a desperate Megan finally came. She had ordered a cheerleader outfit, and this was to Emily's liking. As Emily sat on the edge of the bed, dressed only in her strap on, Megan shook her tits and ass doing cheers for Emily. While making out, Megan offered ``I want to take your dick in my mouth. Can I suck on it?'' Emily obliged and Megan was quickly on her knees with the plastic phallus in her mouth. Megan was by now an experience deep-throater and she had no problem taking it to the hilt. Emily laid Megan on her back. She wanted to be eaten but the strap on rendered her cunt unavailable. So she lowered her asshole to Megan's mouth and began grinding. For half an hour she called Emily a ``whore,'' ``slut'', and ``bitch.'' Finally, she came and Megan begged Emily to take her ass. ``I need to be a real girl, please fuck me.'' After Emily paused, she quickly added, ``your dick felt so good in my throat, please put it in my ass.''

Megan crawled onto her stomach and raised her ass into the air. As always, the first few minutes were painful but Megan then settled into a rhythm. Unlike before, Emily periodically stopped and waited for Megan to beg. Emily was out of her mind with frustration and obliged. ``Your dick feels so good in my ass.'' Five minutes later ``It feels so good to be your slut.'' Megan managed to cum after about 30 minutes of Emily's pounding.

And this became the only way that Megan came. About 3 weeks of frustration was usually enough for Megan to ask for the degradation. Emily made Megan earn it. If the talk wasn't dirty enough, then only Emily would be cumming that night. Megan found that a cute new outfit helped. Letting Emily catch her dressed up in bed, watching lesbian porn, helped convince Emily as well. Before cumming, Megan became a creative cross dresser committed to convincing Emily that she was girly enough to fuck. After cumming, Megan felt pure shame. About half the time she waited for Emily to fall asleep and went into the bathroom to cry.

Ass to Mouth

A couple of years after the wedding, Emily's latest internet fixation had become ass to mouth. She wanted Megan to do this for her but Megan had put her foot down. ``I know you are scared of this, but being a girl means taking it even when it isn't perfect.'' But Megan refused and Emily realized that withholding anal sex wouldn't be enough.

Emily whipped out another tool. She started raising two other fantasies. The first was to have Megan's manhood removed. She really did want this. They were only in the way and what an incredible sign of submission. She imagined keeping Megan's long lost manhood in her desk drawer as a good luck charm. But, unsurprisingly, Megan was dead set against this. And Megan knew that this was impossible anyway. Sex change operations are expensive and only done after years of therapy and preparation. And it wasn't as if there was a network of blackmarket doctors willing to cut someone's dick off. The second was that Megan fuck a guy. Megan was strictly lesbian and was just as opposed to this. And Emily had no desire for this, it was just a ploy.

So they worked out a compromise. In exchange for Emily relenting the operation and sex with a man, Megan agreed to start doing ass to mouth. And even on this, Megan was limited. She insisted that Megan give her advance notice so she could give herself an enema while Emily was at work. ``But that takes away from it. The idea is that you are so hot for my strapon that you just don't care,'' complained Emily. But Megan had reached her threat point and Emily realized that she couldn't be moved. So Megan would suck off Emily's strap on after anal sex, but Emily didn't find it spontaneous enough. And on this cold Montana morning, there continued a rare impasse. Emily devoted considerable thought on how to move Megan onto the dirty ass to mouth that she wanted.

Pissing

Watersports were an on and off feature of the relationship. Emily never got into pissing on Megan. But a few times a year, she would go through a phase where she really enjoyed having Megan drink her pee right from her pussy or serving Megan a glass of piss with dinner. Megan had initially dreaded this. But to her surprise, it ended up being pretty far down the list of unpleasant tasks. Megan didn't like drinking Megan's yellow morning pee but she actually really liked staying up late with Emily, having some drinks, watching some chick flicks, and drinking Emily's milder pee.

Now Emily's 35th birthday was approaching and they had arranged for a special present. For the weekend, Megan had agreed to be Megan's toilet. They had purchased a twin bed for the occasion. For 48 hours, Megan, dressed in her lingerie, would be tied spread eagle to the bed. And during that time, she would drink every drop of Emily's piss. Emily would not speak to Megan during that time. And Megan would only have two one hour breaks each day to eat and clean up.

Megan was apprehensive as the weekend approached. She prepared by going for daily rigorous runs on the treadmill dressed only in her pink running shorts and sports bra. She made sure she was sore for the weekend, that way the bondage would serve as a useful rest period. Emily purchased some fine wine and smoky scotch for the weekend, as well as some bottled water. She wanted to make this count. She also purchased a bunch of frozen dinners, this would be the first time she cooked for herself in a decade.

That Friday, they ate dinner together in silence. After cleaning up, Megan dressed in a simple teddy and asked Emily if she were ready. They went upstairs to the spare bedroom. Megan lay on th bed and Emily gently attached each limp to the bed using four pairs of padded handcuffs. She turned off the lights and left Megan, her toilet, in darkness.

Emily already had to pee. She wanted the first time to be strong and yellow. But she also wanted Megan to have to wait. After about an hour, she came to the bedroom. Speechlessly, she sat on Megan's face. If she just let loose, it would be physically impossible for Megan to keep pace. So she pissed in Megan's mouth in short bursts. It took her 3 minutes to finish. Again without speaking, she started to ride Megan's face. Oral sex had not been discussed. But there was never any doubt that Megan would eat Emily to orgasm.

Emily went out of her way to drink a lot of liquid that weekend. As a result, she pissed in Megan's mouth about 25 times. Only three of those, the really yellow ones, were hard on Megan. All told, she spent an astonishing 9 hours eating Emily's cunt and ass. By the end of the weekend, however, the bondage had grown extremely uncomfortable.

Megan dreaded that Emily would someday ask her to try the other type of toilet duty. She worried that it wasn't realistic to refuse that and resist Emily's request for a sex change operation, dirty ass to mouth, and sex with a guy. And so she resigned herself to going along if Emily asked. But in a rare case of good luck, it turned out that Emily had no desire to try scat and the issue never came up between them.

Chapter 7: Final Humiliations

The worst degradation came after a rainy day one October in Montana. Emily called Megan at home to tell her to ``doll herself up,'' later that night there would be a surprise. Emily told Megan to be sure to wear her sexiest lingerie underneath a ``classy'' dress. Unsure of the reason, Megan dutifully complied, adorning a black corset and thigh highs underneath a form fitting red dress. Carefully waxing and applying makeup with some jewelry, Megan calmly awaited what she expected would be a night of intense sex with Emily.

But tonight would be very different. Arriving home at 5, Emily told Megan that she needed her to do something for her at work. A prominent editor lived nearby in the country. The editor was just shy of forty, reasonably attractive, and into kinky sex. Emily needed Megan to let her have her way with her for one night in exchange for a sure top publication for Emily's career. This was, mostly, a lie. Megan was indeed going to fuck a reasonably attractive women just shy of forty who was into kinky sex. But this woman, Andrea, had absolutely nothing to do with publishing and certainly knew nothing of Emily's field. Emily had, in fact, decided it would be fun to pimp Megan out just this once. She had found Andrea online and they had agreed that Emily would be paid a princely sum for the night. The rules were carefully laid out, Emily didn't want this stranger to break any new ground with Megan. But Megan didn't know this, all she understood was that she was to do whatever sordid and humiliating sex act she was told to perform.

Megan briefly protested. But Emily quickly pointed out that this was the least that she could do given Emily's busy work schedule and Megan's ability to simply tend their home. As they drove far out into the countryside on the increasingly foggy night, Megan became so scared that her hands began to shake. This was too much. Emily was her soulmate, that made living as a woman OK in her mind. But the thought of having sex as a woman with a perfect stranger was terrifying. A tear streamed down her cheek as she imagined the utter degradation of taking the strapon of this mystery woman.

Pulling up to Andrea's home, Emily reached over Megan's lap and opened the door. ``I will be back to pick you up in the morning. I need you to show this woman a good time.'' And with that she drove off. Megan had no option now, the temperature was falling toward freezing, and there was no other shelter within miles. She tentatively walked to the door, and after a minute of hesitation rang the doorbell. The woman who answered the door wasn't gorgeous. Her features were a little above average for the most part, but her tall body was well toned, unsurprising given her hobby as a distance runner.

Their initial conversation could not have gone much worse for Megan. After a couple minutes of small talk, Andrea said, ``One of my biggest fantasies is to fuck a man in the ass. But it is hard to find a guy to do it with here in the middle of nowhere. So I am pretty psyched to fuck you tonight, even if you are a sissy and no longer a man.'' This crushed Megan. She had devised a pair of coping mechanisms to deal with her feminization. Some days, she was just a good spouse, willing to indulge her wife's kinky fantasies. On other days she had come to embrace being a woman. But she never thought of herself as a sissy, which to her was some perverted thing neither man nor woman. Megan held back her tears but she never recovered emotionally from Andrea's insult and was a mental wreck throughout the hard and painful night of sex that followed.

Andrea worked fast. A quick pizza comprised dinner, Megan barely ate. Andrea then proposed that they go to her bedroom. ``I only have one strapon. Why don't I lie down on the bed and you show me how bad you want it.'' Megan's first glimpse of the dildo scared her. It certainly wasn't huge, but it was as large as Emily's biggest. Huge didos were not one of Emily's kinks, her thing was owning Megan, not tearing her up. This toy would hurt.

Megan was dying inside but she remembered Emily's command. She dutifully performed her best striptease, aided by the knowledge that every additional minute spent on seduction delayed her impending impalement a little longer. But finally she was down to her stockings and corset.

``Emily tells me you don't like lube.''

Megan blanched. ``Oh, thats OK. We can use some if you want.''

``I don't think so. Get that mouth over here.''

Megan knew what she had to do. It had taken months, but her and Emily had reached the point where Megan's blowjob was the only lubricant they needed. The deep and sloppy blowjob that followed was not due to Megan's passion for the act, rather she knew that she had better perform if she was to avoid being split in two by Andrea.

Megan's undoing wasn't as much the size of the strapon but rather Andrea's different taste for the act. Emily usually grew tired of taking Megan's ass after about 15 minutes, preferring to then move on the Megan's oral servicing of her pussy or asshole. Plus, Emily seemed to mostly enjoy watching her dildo methodically enter and exit Megan's ass. Andrea, however, was happy to peg Megan for a much longer time, all the while pounding away like a teenage boy. All told, Emily would endure two hours of anal sex divided into three sessions. She was so sore by the third penetration that she wept through its entirety. Megan, on all fours, her mascara dripping down her contorted face, suffered her rape at the hands of a complete stranger.

The time spent servicing Andrea's pussy and asshole came as a welcome relief. After midnight, they settled into bed for the night. In the morning, Megan dressed in a black shirt and a light blue blouse and awaited Emily's return. This time, Emily came to the door.

Andrea then asked Emily, ``it wasn't clear whether it was OK if I used Emily for bathroom stuff.''

Emily replied, ``oh that would have been fine, Megan really likes to drink pee. Do you want to give it a try before we leave.''

Andrea was thrilled, ``sure, if it is OK, I can take her to the bathroom.''

Emily responded, ``I would like to watch. Do you mind doing it here. I promise Megan will not spill a drop on the floor.''

Megan was mortified. She often performed all types of degrading sex acts. But she had never had an audience. She began to protest but a harsh glance from Emily brought her around. Dropping to her knees as Andrea lifted her skirt to reveal no panties, she did manage to avoid any more tears. Within 10 seconds, Andrea unleashed a slow stream of piss into Megan's mouth. Faithfully drinking the piss while allowing some to spill on her blouse, but none to hit the floor, Megan finished to a cheerful, ``good girl'' from Emily. Then just before leaving, Andrea paid Emily for her night of prostitution. As promised, $20.

The Last Humiliation of Megan

Two years later, Emily moved on to her newest fantasy. It had come to her attention that Megan was idle for long periods during the day. So for Megan's 38th birthday, Emily gave her a present. It was a 3x4x6 pink dog cage. Megan was to finish her keeping house, get dinner ready to bake, and then lock herself in the cage until Emily came home. The cage was padded, uncomfortable but bearable. The cage was strong, once locked the only way out was with the key on Emily's chain.

On the third day, Megan sat in the cage deciding what to do. This was too much. Two or three hours of TV each weekday was all she had. Everything else was pleasing Emily. Now Emily was taking that time away. At the same time, Emily turned onto the highway heading for home. The Montana weather in Spring is unpredictable. Hail storms, like the one on that highway, can come with little notice. Within 15 seconds, the road was an ice slick. Emily's car lost control and turned 180 degrees. Right into the path of an 18 wheeler.

The sheriff started to drive to Emily's house. She hated this part of the job. If nobody answered the door, she planned to go ahead and let herself in.