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Breaking Him (Up)
Breaking Him Up
© Ed Cantor 2012

Edward had been living with his girlfriend for nearly a year. Their sex life had slowed considerably and he found his thoughts more and more drawn to fantasies of more experimental and less inhibited activities.

His thoughts and fantasies wandered aimlessly at first, but then found himself more and more communicating with one specific woman, via email and on the phone. She wasn’t just any woman, however, she was a Domina. She was skilled, personally and professionally in taking control of the men (and women he found out) she was in relationships with.

He began to realize he was now searching out every spare moment he could to spend talking to her. He was lying to his girlfriend, Cheryl, to carve out spare moments. More than once he had pretended to be at work late so that he could sit in his car and speak to her on his mobile. He’d made up evening or weekend appointments with friends and colleagues to talk to her or find internet cafes to compose long emails to her.

The more he needed her, the more she loved it. She fed off his growing addiction, and she was beginning to make use of it to fulfill her own agenda and to satisfy her own pleasures.

She’d made it clear to him that he was now only allowed to cum if she permitted. That put a quick end to any unplanned sex with Cheryl. Once she had come home randy after a night out with her friends, and in a panic he had hit upon a strategy of plying her with oral sex instead. She had still wanted him inside her after her first orgasm, so he just attacked her clit with his tongue again, and again, until she finally drifted off to sleep.

He had thought, upon reporting his ingenuity to Ms Katy (she insisted upon the title), that she might be proud of him for the creativity. He was wrong.

“Next time, silly boy, you’re going to tell her you’re just not in the mood. If she presses you on it, maybe you’ll have to tell her that the sight of her drunk in kind of turning you off.”

He sat in his car, his heart in his throat. He could only imagine the fight that would trigger.

He was reminded of Ms Katy every time he took any call now, as she had insisted he buy a new phone. She wanted him to have one with a camera, as she was more and more giving him instructions of photos or audio recordings she wanted sent to her.

Some of the photos were quite embarrassing. She insisted he carry a Sharpie marker on him at all times, and without warning she’d tell him of specific words or silly drawings he’d have to make on his body. After he’d sent her each photo, he knew he’d be in for days of trying to hide the marks on his skin. Even with the most vigorous scrubbing, there was at least a two day mark.

With each instruction, there was the clear and spoken understanding that failure to obey to her satisfaction would result in punishment. The ultimate punishment, one he couldn’t even bear to think about, was the denial of her presence in his life. Once when he had hesitated for too long when she had asked him to share his home address and phone number, she had refused to answer his calls for a week. He had nearly been driven mad by the ordeal, unable to think clearly by the seventh day.

He had to make it up to her by sharing now only his address and phone number, but also his work address and the name and email addresses of three of his superiors at work, as well as that of his young assistant. The last penance was an online gift of $500. Now his bank statements were something else he had to hide.

Sometimes he was afraid of Ms Katy and her seemingly endless stream of ways to tease him and push him. It no longer seemed enough for her to have his secret obedience.

She had once given him one hour to send her a photo of him outside in a public place in a pose that showed that he was wearing women’s underwear. It was only 11am, so had had to make up some vague excuse to tear out of work and find a department store, buy himself a pair of panties, change into them in the mall washroom and find a place to take the photo. He hadn’t thought to bring any briefcase or jacket, so had to throw out his boxers rather than carry them awkwardly around. He made it with just ten minutes to spare. He was walking back to his office, feeling embarrassed and silly when she had called him. Rather than being done with him, she ordered him to lunch at the nearest strip club. Along with the club sandwich he was to have three consecutive lap dances, so that he was sent back to work in panties stained with precum and a body aching with unsatisfied desire.

Some of her tasks for him were purely pleasurable, like when she had him tell her in detail how he would go down on her, all while he was allowed to be stroking his cock while he spoke to her. Some tasks were just instructive, as was the full course of cooking lessons she sent him on. The only tease during that experience was her instruction that he bring his own lace-trimmed apron. There were a few whispered comments and giggles, but he was among strangers. She also had him healthier and fitter than he had been in years, as she had also imposed a strict routine of working out at a gym at least three times a week.

The hardest ones were those that were just tests of his obedience, demonstrations of the ever-increasing scope of her power. One Saturday night he’d had to dress himself in a pink rubber thong, snug leather pants and a skin-tight t-shirt and spend the entire night, from 8pm until closing at one of the more notorious gay bars in town. He’d had to turn on the tracking application on his phone for Ms Katy, to prove his continued presence, as well as emailing her photos of himself sharing the drinks he’d had to buy for each man who came up to speak to him. By the end of the night he was drunk and humiliated, clumsily changing back into his normal clothes in his car before hailing a cab home.

She teased him mercilessly the next day, reading out the names and phone numbers of each and every one of the men. She taunted him, joking about what she might have him do with those men the next time, and whether she’d have him do it drunk or sober.

She was also inserting herself more and more into his relationship with Cheryl. She would deny him permission to have sex with her for longer and longer periods. He would be instructed to feign disinterest in sex to her, but at the same time she would insist that he begin leaving men’s magazines in his briefcase or in his bedside table. It started with things like Maxim, then quickly moved on to Playboy, Penthouse and Hustler.

Ms Katy instructed him to become more verbally critical of Cheryl’s appearance, her choice of clothing, even her body. One instruction that Ms Katy could barely speak through bursts of laughter, was to initiate a discussion with Cheryl about whether or not she’d ever considered breasts implants. That fight, all recorded for Ms Katy on his iPhone, meant a night in the spare bedroom for him.

One of Ms Katy’s more elaborate, not to mention expensive, tasks for him involved weeks of anticipation and planning. He’d had to tell Cheryl of an upcoming trip for work. He had to go so far as to book a flight to Chicago and reserve a downtown suite. He dutifully kept up the charade, packed his bag, and made the trip on the appointed weekend. He felt strangely free and trapped at the same time, standing in the hotel room, looking out over the skyline.

He wasn’t allowed any sightseeing. Instead Ms Katy, using his credit card number and the information he’d sent her about the suite, had lined up a series of appointments for him. He was allowed one trip out to by a complete and matching set of bra and panties, stockings and garters as well as high heels and lipstick, as well as a bag of party balloons and two cartons of milk. Back in the hotel room, he had to dress in those items and nothing more -- nothing but the lingerie and balloons full of milk as his own fake breasts, stuffed inside the bra. And like that, feeling humiliated and silly, he had to take photo after photo. He also had to answer the door this way, no matter who answered.

There were plenty of visitors, as Ms Katy had lined up a stream of escorts to come see him. Every three hours there would be a new knock. For each one he had to display his appearance, giving her his camera to take photos. Rather than receive sex of any kind, he instead had to serve them. Some he went down on, some he massaged, and some he just had to crawl around on the floor for. There were two visitors that stood out from the rest. One was a professional Dominatrix. She bent him over the edge of the king size bed and spanked his panty-clad ass red and raw, and then proceeded to put him through his paces giving her rather large strap-on cock a very convincing blow job.

The second was a male escort. His heart was pounding in fear and horror, never knowing what might be asked or commanded of him, and knowing in his heart there was probably nothing he would hold back. After two hours of teasing and more crawling and posing, he found himself on his knees, his wrists cuffed behind him with his head back and his mouth wide open. The man jerked himself off, his free hand holding Edward’s phone and recording video, until he came all over Edward’s face and chest. Afterward, while Edward knelt with cum drying on his face, waiting to be freed, the young man made sure to destroy all of the underwear Edward had brought along in his luggage.

A text message instructed Edward he wasn’t allowed to change clothing or shower until morning, so he spent the remainder of the night a humiliated mess, wondering just what the hell had happened to his life, and what more he’d have to do to be allowed a chance to cum. Having to wear the panties on the flight home made being picked up at the airport by Cheryl all the more nerve-wracking.

He was now aching for sex, for release, and Cheryl was getting pretty confused and hungry as well. The situation became more fodder for Ms Katy’s wicked mind, inserting herself and her desires into their relationship. Cheryl had a short blond hairstyle, so Edward was instructed that he was allowed to fuck her only if she agreed to wear a long brunette wig and sunglasses. As part of the role play story to convince her, it was also made clear that he was going to be calling her “Kat” during sex. Cheryl was confused, but she went along with it. After all, it had been months since they’d slept together. Again, the audio experience was to be recorded, and Ms Katy seemed to orgasm herself as she listened to it during his next phone call.

Cheryl had gone along with the wig and disguise the first time, but she became more and more annoyed since Edward had been told to spend the entire month to come looking for sex from her at least every other night, but only if she would wear it again. After a week and a half, it became another fight, another night in the spare room, and another two and a half weeks of chastity for Edward.

Edward often worked at home, and he had turned the smallest spare bedroom into a makeshift office. A new addition to the room was a small home safe, secured with a combination. Inside the safe was the growing collection of items that Ms Katy had insisted that he purchase and keep nearby. He was now the far-from-proud owner of over fifteen pairs of panties, two bras, breast forms, three sets of stockings and garters, four colours of lipstick, a rubber ball gag, a lewd rubber dildo (molded far too realistically for his liking), two anal plugs and a set of anal beads.

Sometimes when he was alone in the apartment, on the phone with Ms Katy, she’d have him model pair after pair of panties for her, taking photos in addition to the live video stream over webcam. Other times, she’d give him detailed pointers as she had him practice cock-sucking technique with the dildo -- never without first applying lipstick, of course. During one session he went through an entire tube of lube as she had him perform for hours on all fours, fucking himself in the ass with the dildo while wearing the bar, fully stuffed, drooling around the gag.

By now there also didn’t seem to be a single day that he didn’t have to stop in there on his way out, after having gotten dressed, to secretly replace his boxers with panties, which he’d have to wear all day at work. The thongs at least didn’t give him visible panty lines, but it was a constant reminder of his situation to have to always go the stall when he had to urinate, for fear of anyone seeing a peek of lace or satin.

She would play with his body with near-medical skill. She would have him go for weeks without being allowed to cum but forcing him to stroke himself to the edge of release over and over, so that his balls were full and aching and sore. He swore he could see that they were bigger than normal. The teasing would train his body to keep producing cum, but it had nowhere to go. Then, finally, when he was permitted relief, he’d have to spurt the thick, yellowish cum into a wine glass, and then down every last drop of it.

In fact, unless it was during one of his allowed sessions of sex with Cheryl, there was no longer a time that he came that he didn’t taste his own cum, one way or another. Some were simple, like drinking it out of the wine glass, or being instructed to add it to his coffee if she made him cum at work. Other times it was more of an ordeal. He’d been made to jerk off into a condom, knot it, then carry it around in his ass for half a day, then drip the warm goo over his tongue at a time of Ms Katy’s choosing. The most humiliating for him was when she made him cum all over his dildo and then have to suck and lick every single drop off of it. It felt to much more humiliating to have to do this after the high of his erection was faded, leaving him with just the humiliation of the acts he seemed to have no choice but to perform.

To remind him of her power over him, Ms Katy would occasionally talk about all the things he’d done for her, naming dates and places. He had given her his full name almost immediately after they started talking and his home and work addresses followed soon after. Before he had time to think of the implications of sharing these things, she knew just about everything about him. She’d insisted on password access to his Facebook profile and had also created an incredibly explicit and frank Fetlife page for him.

In no time, Ms Katy knew the names, phone numbers and email addresses of all of his friends and family as well as Cheryl’s. She had the password to all of his email accounts. She made him sit in his home office, gagged and plugged, wearing nothing put panties and a bra, slowing teasing his cock, while she took control full of his computer through online conferencing software. He had to watch and stroke as she browsed through his files and photos, making copies for herself as well.

Copying those photos must have inspired or pleased her, as it wasn’t long after that that she commanded that Edward find a way to take more and more explicit photos of Cheryl. Ms Katy would give him specific instructions as to what kind of lingerie to buy for her, and how to praise her body, tell her how much she turned him on, how much he’d love it if she’d let him take a picture or two of her, how he’d do anything if he could. Eventually Cheryl gave in, and since she was rewarded each time with enthusiastic sex of the kind that was now all too rare between them, she was easier to convince each time.

Without fail, the next morning an email would be waiting for him, demanding a full recount of the evening. She wanted to know how Cheryl had reacted, and if she had seemed embarrassed or aroused. Of course, Ms Katy would also demand that he email her the images, or she would simply take control of his computer remotely and copy them over herself while he watched.

Edward felt a new and fresh panic the day he saw Ms Katy’s name appear on Cheryl’s Facebook page -- noting her as a recently added friend. He could just feel the colour drain from his face. It took about two days before he dared ask Cheryl about it, trying to sound as casual as he could manage.

Cheryl’s face lit up as she told him about this new woman she’d met at her book club. She was fun and outgoing and and always was in a good mood. She was smart, had a lot to contribute but never in a overbearing way at all. She seemed to like just about all the same books that Cheryl did and even more importantly she seemed to hate all the same things as well. Edward tried to keep a straight face, nodding along, thinking to himself that it was his own actions that had let Ms Katy see to intimately into Cheryl’s interests. Now Cheryl had a new friend, and it sounded like they were even going to get together outside of the book club too. After all, Cheryl had pointed out, he was so much busier with work these days, it was nice for her to have her own friends and plans.

Ms Katy had a good laugh at his expense when she spoke of this friendship with him. She teased him about how she couldn’t take her eyes off Cheryl when she met her in person, and how her mind kept going to all the sexy photos he’d sent of her, wondering just what kind of lingerie she’d be wearing underneath her casual clothing. She joked she was going to have some wonderfully intimate talks with Cheryl about her ‘boyfriend,’ and about how he was getting into her panty drawers. Maybe she’d even give Cheryl some pointers about how to deal with a man who seemed to be spending too much time looking and dirty magazines and not enough at her.

As was always the case, she had him touch and teasing himself while she taunted him. No matter how humiliating or degrading the suggestion, no matter how much it might expose him, she was training him to love her control over him with this simple Pavlovian connection between her wickedness and his arousal.

Edward found out, much sooner than he could have even feared, that Ms Katy did not bluff. In fact, she played this game even more completely that she had let on.

Not two weeks later, it was Book Club night on the Friday. Now that Ms Katy was attending regularly, she had started to send Edward on errands, with chores to complete that ranged from humiliating to degrading and back. Last week he had been sent shopping at the mall, with instructions to make a very good customer of himself at both of the “plus size” shops at the mall. He’d come home with bags full of panties, stockings, nylons, bras and even a little black dress. This week it seemed he would be shopping again, but in no ordinary store.

As was the case the week before, he waited until Cheryl left, kissing her goodbye, and then immediately starting his obedience. He stripped out of his street clothes and re-dressed himself in dark stockings with garter belts and a pink rubber thong. He leaned over (in front of the webcam set to record video) and filled up his ass with one of his larger plugs. He then turned again, reaching into the panties, to ease his cock and balls into the “three-ring circus” cock ring set. It would have been easier to do these things before putting on the lingerie, but Ms Katy dictated the order. She liked that the panties made it into all the pictures.

Once he was prepared, he was to dress in a simple black suit with a white shirt and black tie. She had made an appointment for him at Northbound Leather, one of the more complete and serious fetish shops. That was all he knew of his errand, other than he was to buy the correctly fitting and chosen versions of what he was being sent to try on.

He arrived and nervously made his way up to a shop girl. She smiled upon hearing his name and led him to the back of the store -- the front of the store was full of leather good and clothing, but the back was where the more extreme items were kept. His appointment was with with a woman who identified herself only as Miss Neutel, and she had clearly seen it all and was well informed of his situation. She asked him almost nothing, and instead gave him a series of simply instructions to follow.

The first item for him to try on was a lace-up leather corset and it was fitted to him and laced so tight that it was difficult for him to breathe. Once she was satisfied she removed it from him and set it aside. Next was a gag, or more accurately, a gag system. There was a harness around his head that secured a leather device against his mouth. A small rubber protrusion pushed into his mouth, while on the other side of the leather panel was a mounting sleeve for a variety of attachments. She fit the gag to him but didn’t bother showing him the attachments that were being included.

For the last item, she instructed him to pull remove his trousers, and after just a moment of shock, he complied. There were far too many risks to even contemplate disobedience. She removed the cock rings he wore and replaced them at with a single ring, constantly evaluating its size and fit. Once she was satisfied, she guided his cock into a matching clear plastic sleeve, guiding it into waiting posts that projected from the base. He was starting to worry about it, but not soon enough to make any decisions before he heard three small clicks.

She pulled his panties back up, covering up the bulge of the device. He stammered something about the locks, and got only the reply that he wasn’t to worry about it, and that Ms Katy already had all the keys for these locks. After settling up the hefty bill, he was sent on his way.

He had completed the items on his list, so he decided to head home. The bags were heavy and bulky and were quite a chore to carry. Adding to his discomfort was the building dull ache of his plugged and stretched ass. He was also finding the tight fit and strange sensation of the chastity device locked upon him quite distracting and uncomfotrable.

He heard voices in the apartment as soon as he opened the door, so he dashed quickly toward his office to stash the bags and change. Cheryl heard the door open, however, and was immediately calling out to him to come in and say hi.

His head was pounding. There was no way he could make up an excuse to stall for enough time to get out of all his fetish trappings. He dropped the bags into the office, behind the door and looked down over himself, checking to see if the bulge of the chastity device was noticeable or if there were any lines through his pants from the panties or stockings. He took a deep breath and walked toward the living room.

To his horror, there on his sofa was Ms Katy. She was reclining across it, cradling a large glass of red wine in her hand. She was wearing a very wide smile and a grey wraparound knit dress that seemed to just cling to her.

“Edward, come on in. This is Katy. She’s the woman I told you about, who joined the book club. We were having so much fun that I simply had to ask her over for a drink”

He could hear his heart pounding in his ears. He tried with all he had to keep a straight face as he stepped over to her and extended his hand.

“Hi there, Katy. It’s nice to finally meet you.” He swallowed hard. “Cheryl has been saying how happy she’s been to have you in her club.”

Her smile only widened. “Oh, thank you so much. I simply love Cheryl too. Better be careful or I’ll try to steal her away from you.” She laughed immediately, no doubt enjoying Edward’s discomfort as much as her own jest.

“Well, I’ll get out of your way and leave you two to keep chatting,” he said, trying desperately to get some distance, to get out of the room.

“Oh nonsense, Edward. One of the reasons I wanted Katy to come here was I wanted you to meet her,” Cheryl said. “Sit down, I’ll get you a glass of wine.” And off she was into the kitchen. As Edward watched her go with a growing sense of doom and defeat, he flinched at the sudden feel of an unexpected intimate touch.

Ms Katy was leaning forward, giving a generous view of her cleavage in the V neck of the dress, but more importantly she was gripping his trapped cock and balls. She cupped him, feeling the outline of the hard plastic trap around his cock and and rubbing at his exposed balls.

“Come. Sit. I’m sure your full ass would prefer to be on the soft sofa with me,” she whispered at him.

Defeated he sat down, trying to find a comfortable way to sit, and forced a smile and thanks as Cheryl returned with his wine.

They chatted and laughed, and Edward did all he could to try to be a part of the conversation, while fighting the urge to squirm and wriggle with his growing physical and emotional discomfort. He was also making his way to the bottom of his wine glass rather quickly.

“Oh, you’re empty too,” Ms Katy exclaimed. “Here, my turn to serve.” She hopped up and grapped all three wine glasses to refill. “Just point me to the kitchen!”

“She’s amazing, isn’t she?” Cheryl whispered to him, as soon as Ms Katy was out of earshot.

“Oh yes, she seems really interesting and fun,” was all he could think to say.

“Here we go again,” laughed Ms Katy as she redistributed the glasses.

Edward was trying to let go of his worries and paranoia and just enjoy the evening. The wine was helping, that was for sure. He just kept trying to tell himself that he was here with the two women in the world he found the most sexy and arousing. It was sort of working, but he was also starting to notice that the chastity device was aching more than it was before. His cock felt like it needed to get hard right now, but of course the thing was keeping him tightly trapped.

He was so distracted by his own discomfort that it took him a while to notice that Cheryl was really starting to yawn. She was making apologies, giggling that she was tipsier than she thought. He smiled and laughed with Ms Katy and they continued to talk for a few more minutes. Then, without a sound Cheryl yawned another huge yawn and let her head fall back against the back of her chair. She was fast asleep.

Ms Katy was smiling wide. “Just you and me now, lover.”

He jerked his head over, watching for any reaction from Cheryl to this kind of language.

“Oh don’t worry, Edward. After what I put in her wine, she’ll be out cold until morning.”

“God. You didn’t!”

“Yes, I did. Now it’s time to end the foreplay and get down to business. I’ve been waiting for hours for this. Get the fuck out of that suit, right here, right now, and let me see your pretty ass in those panties.”

Even now, with his unconscious girlfriend just a few feet away, he knew that Ms Katy was serious and he didn’t hesitate. He stood and piece by piece stripped out of his jacket, shirt, tie and trousers, until he stood before her in the straining panties, stockings and garters.

“Very pretty, you dirty little whore. Very pretty indeed.” Her smile was so dangerous. “Now, I’m going to get rest of what I need from your dirty little office. By the time I get back, I want you to have Cheryl stripped down to her bra and panties.”

His eyes widened in horror.

“Don’t worry, she won’t wake up. Don’t disappoint me, slave.”

What the hell had he gotten himself into he wondered. With growing fear he made his way over to Cheryl, still laying limply in her chair. He opened the buttons of her blouse and lifted her forward to ease it back off her shoulders and arms. Next he opened up the button and fly of her jeans. They had a bit of stretch to them, so it was quite a struggle to wriggle them down over her hips and down her legs. By the time she was free of them, reclining so peacefully and beautifully exposed, he was also feeling the throb of his cock quite painfully.

Ms Katy returned hauling what seemed to be the complete contents of his safe as well as the bags he had brought home that evening.

He shifted from foot to foot as he stood waiting for what was next.

“You seem uncomfortable, Eddie. Something bothering you?” She was nearly giggling out loud.

“Yes, Ms Katy. This chastity device is really aching. I think it may be too small for me.”

She laughed out loud. “It was big enough before, wasn’t it?”

“Yes,” he said, blushing.

“When your cock was soft, you mean?”

He nodded.

“But now, as you are getting turned on and hard, it is bugging you?”

He nodded again, his face red and burning.

“That might be because of the Viagra in your wine pet.” Again she roared with laughter. “Just one more reason to be a good boy, and maybe I’ll let your horny cock free. But first, we have a lot to do. Come here, let’s get you properly dressed.”

He stepped over to her, and between the items from his collection and a few she seemed to have brought with her, she carefully composed his look. She put him into the new corset, cinched up even tighter than in had been at the store. She put a sexy lace bra onto him, stuffing it full of his largest pair of breast forms. She painted his lips with garishly red lipstick and made up his face with foundation, blush, and whorish eye makeup. Next was a long blond wig. Every step was documented with photos he had to pose for, both on his own and standing or sitting with the peacefully sleeping Cheryl.

The final step was a very short red latex minidress. It took him quite a bit of struggling to get into, but when he did, he cut quite the silhouette thanks to his corseted waist and immense fake breasts. Finally she had him step up onto four inch spike heels. He struggled to balance atop them as she closed and secured their locking straps.

“Follow me,” she instructed as she walked out onto the balcony.

He was incredibly nervous about being seen like this, but he had no choice but to obey.

Out in the cool air, she stood and looked out over the balcony railing. “You see that spot down there, on the sidewalk, brightly lit by the street light?”

He nodded nervously. He hadn’t really noticed it getting dark, but it came to him just how late and night it now was.

“You’ve got five minutes to get down there. You’re going to stand down there on the sidewalk, in the middle of that light, for fifteen minutes. When your time is up, I’ll flash the lights here in the living room and you may return. Understood?”

“Yes, Ms Katy.”

“Good. Get going. Your time starts now.”

He was glad it was late, as he at least knew that his building was generally quiet at this time. All he could do was hope no one would see him. He thought about taking the stairs, but he knew that he’d never make it in time in the high heels.

He looked at himself in shame in the mirrored interior of the elevator.From a distance his forced curves and long blond hair might be able to fool someone, but up close he was just one ugly cross-dresser.

He scurried through the lobby, his heels clicking on the terrazzo flooring. Going through the lobby, he thought about the closed circuit TV, and wondered if anyone was watching him jiggle and wobble out the door. He found his place on the sidewalk and looked up at his lit windows. Ms Katy had closed the blinds, but he could still see their glow. He wondered just what secret she was trying to keep from him. Only now did he realize that he’d left Cheryl up there alone and unconscious with her.

He also noticed as he paced around the small circle, stepping and shifting his weight back and forth, trying to ease the pressure on his feet and the discomfort of his ass, that he was looking and acting like the cheapest of hookers on a street corner. One or two cars did drive by, and he knew he was getting some strange looks, but all he could do was to turn away from each oncoming vehicle, hiding his face and she showed off his latex-clad behind.

His time in exile out on the street seemed to last forever. He had no watch, of course, so all he could do was wait and watch the window. Finally the lights flashed and he rushed back to the building as quickly as he could. He cursed at the doorway, realizing he didn’t have keys either. He buzzed up, and heart ring after ring, as Ms Katy made him wait. After a few agonizing minutes in the brightly lit lobby she answered, laughing, and buzzed him in.

He had to wait again after knocking at his door. He was nearly broken, his nerves ragged and jangly when she opened the door and escorted him back inside. As he entered the living room, Ms Katy pulled open all the shades again, exposing them all to whomever might be gazing in from across the street.

His eyes, however, were locked onto Cheryl. Ms Katy had indeed included her in her depraved plans. She was still seated, sound asleep, in the large chair. The simple bra and panty set she had been wearing were gone, replaced by a leather shelf bra with only enough cup to hold her beautiful breasts up but leaving the majority of them exposed, including her tight nipples. There were leather panties as well, but they were hidden beneath a strap-on harness fitted with an immense pink rubber dildo.

“Get on your knees, pet. Crawl to her,” Ms Katy instructed with cutting malice. “Show me how your skills at cock-sucking have been developing.”

His eyes jerked back between Ms Katy’s gaze and the blank expression on Cheryl’s face, but of course there was nothing he could do but obey. As he slid down onto my knees, Ms Katy was already taking photos.He wondered just how many incriminating photos had been taken while he had been in exile down on the sidewalk.

The corset, the plug, the restrictive chastity device, and the weight of his stuffed bra made him very aware of the ache and strange sensations of his body as he moved on all fours across his floor. He approached Cheryl’s spread thighs and raised himself up. He took a deep breath and opened his painted lips to the obscenely protruding dildo.

“Don’t just suck it like a greedy whore! Lick it, kiss it, worship it. Show me how much you love that cock,” Ms Katy instructed.

He always hated this part most of all. It was always a humiliating challenge when he had to practice taking these things into his mouth and throat, but it was degrading on a whole other level to have to act out this seduction, as though he was working to tease and arouse a living cock. He knew that was why she did this to him, so that his mind would be full of the horror of having to complete this service for real. She’d brought him so close in the past, but it was still a threshold he’d not been forced over.

“Mmmmm, that’s it. Good slut. Show me how much you want that cock inside you!”

He kept on kissing the far-too realistic rubber cock head, tracing his tongue around the ridge as he’d been taught, then kissing and licking up the underside of its full length. He licked and kissed all around it before finally taking its girth inside his mouth.

She seemed to approve, as she took her instructions to the next level. “Now, get your ass up in the air while you work that cock, whore.”

He arched his back, lifting his bottom higher, only to feel his panties pulled down around his knees. His anal plug was quickly and painfully pulled from him, leaving him moaning around the rubber cock. He hated this sensation too. After having been plugged for so long, he could just feel how slow his ass was to close. He felt -- and was sure he looked like -- a well-used whore.

He wasn’t empty for long. As soon as Ms Katy could step into her own strap-on harness, she was on her knees behind him, thrusting deep and hard into him. Impaled between the two massive rubber toys, all he could do was ride the rhythm of the thrusts, moan and drool, and hope Ms Katy would be please and amused quickly.

She pushed and rammed against him so hard, driving the strap-in so deep into his mouth. Almost immediately he was gasping, groaning, and nearly gagging on it. It was murder to feel her ram her dildo up so hard into him, so deep and full, stretching him even wider, but it was even more humiliating and horrifying that he was here, fucked his way while he was drooling all over Cheryl’s inner thighs.

Despite his physical agony and the unbelievable level of this depravity, being so close to Ms Katy when she was enjoying herself so fully and starting to sound quite aroused was definitely inspiriting his own lusts. Lusts that only increased his discomfort, as she cock fought to burst the confines of his chastity device.

Pain and aches were building upon each other. His ass was sore, stretched and roughly used. His jaw was sore and he felt a rawness building in his throat. The rubber of the dildo he was servicing was unyielding, and it was being pushed deeper into his mouth with every thrust. And of course his cock was still so painfully in the midst of its drug-fuelled rebellion against the confines of the chastity device.

Ms Katy suddenly slowed with her thrusts, then pulled out of him altogether. He was sure she hadn’t climaxed yet, so she was either not getting all the sensation she needed or she was just pausing for the next act in some secret script.

He knelt there, frozen, not wanting to move without direction, despite the fact that he was still bent over in this humiliating position, and drooling around the rubber strap-on cock that filled his mouth.

“We need to pause, princess, despite the wonderful show you are putting on,” Ms Katy giggled. “Actually, it’s more accurate to say we need to pause because of the quality of slutty performer you are. You see, Bull has become quite excited.”

With those words she pulled back on his head, drawing him off the dripping dildo with wet slurp. She turned his head to the open doorway to his bedroom.

Standing there, taking it all in, witness to his humiliating oral service and the exposure of Cheryl’s body was a man he’d never seen before. He was huge. A mountain. He must have been about six and a half feet tall and he looked like he was crafted out of marble. All of him, as he was also completely nude.

As hard as it was to ignore the rest of his physique, what stood out to Edward’s greatest horror was his massive cock, standing straight out at attention, pointing at him.

“Your slutty show, your big bouncing tits and your red swollen lips devouring Chery’s cock have made our friend Bull here rather excited, as you can see,” Ms Katy continued. “He was sure, looking at you pacing the sidewalk like a common whore, that you were nothing but a cock-tease, but I’ve assured him that nothing could be further from the truth.” She was smiling wide, clearly loving the effect she was having on his tortured mind.

“Come nice and close, Bull. There’s no need for you to be a stranger to my slutty kitten and his Cheryl.”

“Bull” was far from shy. He walked right up to where Edward still knelt before Cheryl, so close that his thick, rigid cock stood erect between them.

“Get to work, tramp, with your hands... unless you’d rather keep practicing with that slutty mouth,” she commanded, with a fearful strength in her voice. She was not going to let him humiliate her in front of this man.

He reached out, with both hands trembling, and took hold of the massive shaft. He was so big, so thick and long -- putting Edward to shame, as though the chastity belt, fake tits, wig, stockings and dress were not enough.

He started stroking rather tentatively, forcing himself to do that much. Somehow, feeling the warmth and fleshiness of a real cock in his hands was more degrading and humiliating that servicing the rubber versions in his mouth had been. Her heard Ms Katy clear her throat, and a glance up at the expression on her face let him know very quickly that his current efforts were not sufficient.

As he returned his focus to Bull’s cock, stroking harder, faster, and working the whole, damnable impressive length of him, Ms Katy seemed to approve, as she switched from direct supervision back to taking photographs of his humiliation.

“That’s it,” she started calling out, like a photographer coaching a model, “work it all. Work his balls too. Massage and squeeze them... I’m sure they are quite full by now.”

He had to adjust himself, getting even closer, now using both hands to work over the cock. He blushed, realising with a sinking feeling that Bull was getting even larger in his grip. He could feel his muscles tensing, see his cock throbbing, even see and smell the precum making his cock head glisten. In a few minutes, his hands were sticky with it.

“Oh, you’re a natural cock-pleasure, slut. Look what a good job you’re doing. Look how wonderful you are at pleasing a real man. We might have found your true calling!” Her words sliced at his soul.

“Ready to cum, Bull?” she asked this trembling mountain of a man.

“Yes,” was his only response, grunted out in a deep baritone voice.

“You can feel him ready to explode, slut, can’t you?” She didn’t bother waiting for a response before continuing. “Tell me, Eddie, do you think that if Bull here let go of his full load all over Cheryl’s face and hair and tits, that you’d be able to get her completely clean in time for morning? I wonder how long those sleeping pills last? Do you think a shower or washing her hair would wake her up? Those would be difficult questions to answer, wouldn’t they? I suppose you could tell her that you just jerked off into her hair after she want to sleep... Maybe that’s a bit better, do you think?”

His voice broke with the horror of it, as he pleaded. “Please Ms Katy, please! Please don’t do that to her. Please! Please don’t!”

She laughed in his face. “I’ll tell you what, whore. You seal your lips around his cock and you take every drop into that well used mouth of yours. Every drop. You miss any, and I’ll mark her with it myself. Understood?”

His heart fell, but once again, she had placed him in a situation with no other choice.

“Yes, Ms Katy, I understand,” he sighed.

“Good. Do it now; I don’t think you’ve got much time left.”

He leaned forward, guiding Bull to him, and took the strangers huge cock into his mouth, sealing his painted lips around him tightly, as he continued to stroke and jerk him. The strong, salty taste filled his mouth immediately.

“One more thing, pet,” she whispered into his ear. “Do NOT swallow. Not yet. Hold it all in your mouth until I say so.”

He certainly did not have to wait long. His stroking was at a fever pitch, and with a word from Ms Katy, Bull released. Cum hit the back of Edward’s throat, hard, fast and hot. He fought his gag reflex, taking it in, spurt after spurt after spurt. Dammit, he just kept cumming, and Edward’s mouth was filling up, and jizz was threatening to spill out around his lips. He drew back a bit keeping just Bull’s cock head in his mouth, making extra room.

Finally, with his cheeks swollen and full, Bull sighed and stopped thrusting. Edward’s stroking turned to milking, making sure he drew every drop of the disgusting load out of him. He couldn’t risk leaving any to be smeared over Cheryl.

Bull finally pulled back, popping out of his mouth, which Edward quickly sealed shut. He seemed perched on the edge of gagging or vomiting, but he had to hold on. He was breathing rather rapidly through his nose.

“Kneel upright, get your ass off your heels,” she instructed, and he obeyed. He felt her hands on him. Oh thank god, she was freeing him from the chastity device. But why? Fear flowed through him. She placed a wine glass in his left hand.

“Lower yourself now,” she said, and as he did, he found that she had placed a new plug beneath him. She made sure it was worked completely up inside him before she was satisfied to let him continue.

“There. Just as you should be. Your ass stretched full and your mouth full of cum. This is how a slut like you should orgasm. Go ahead, jerk and please your little cock for me. Try not to compare it to Bull’s while you play with it.” She laughed, her voice filling the apartment, as Cheryl lay back, slumped still in her chair, the obscene strap-on still protruding from her body. “When I see you start spurting into that glass, then you can swallow the gift Bull has given you. Go now, we don’t want to wait too long, do we?”

He reached down and found his cock with his hand. It was sensitive from having been crammed into the device for so long, and still so hard from the effects of her drugs.

She not only kept taking photos of him, but also took the time to pull Cheryl’s full height dressing mirror in front of him, so he could see just what she had made of him.

His wig was crooked, and his garish red lipstick was smeared. His cheeks bulged fool like a chipmunk's. His shape was still formed by the corset narrowing his waist and the breast forms giving him swollen curves hugged tight by the clingy dress. The dress was bunched up around his waist and his panties were stretched around his knees. And through it all, there he was, stroking and jerking and pulling at his cock with the fervour of a man possessed. It was all he could do to get enough air through his nose as his heart pounded and his faced reddened.

He didn’t want to see what he had become, but he couldn’t look away either.

Finally, finally, finally he came, spurting out thick ropes of cum into the glass. As the pleasure and extreme physical high buzzed through him, narrowing his vision into a focused tunnel, he swallowed down the mouthful of gooey cum. Cum that he had sucked and slurped from another man. This degrading horror mixed intimately and strangely with the undeniable pleasure of being finally allowed relief and release, as pleasure did with pain. When his mouth was empty at last, he tried to lick the taste from his teeth, but it clung there.

“You’re not done yet, silly,” she pointed out to him. With a resigned knowledge, he lifted the wine glass to his painted lips and tilted it back, letting his own cum pour into his mouth as well. He couldn’t help but notice that the tastes were different, and with a shudder he hoped, likely vainly, that he’d never have to notice something like that again.

Ms Katy put down her camera after taking her last shots, and passed him a glass of wine. “Here you go, pet, unless you’d like to savour those tastes for a bit longer.”

He received the glass from hand thankfully, and drank it down, letting the red wine’s strong taste fill his mouth. God, he was tempted to gargle with it, but he swallowed it down, letting it mix with the warm lump of cum he could almost feel inside him.

He was still plugged, still dressed in this sissifying ensemble, but at least his cock was free, and the aching pain was gone, the all-encompassing need satisfied. But with that release, the sexual high of arousal quickly fled. Now it was all just harsh reality. She had made him go out in public in drag, dressed like a prostitute. She had used him, in his own home, in the home he shared with Cheryl. She had drugged Cheryl, made him strip her down to her lingerie, only to strip her completely with him sent outside. She had made him leave her there, alone with Ms Kat, all the while knowing what she was capable of. She’d made Cheryl part of her games, part of these photos. And she’d made him suck a man’s cock, swallowing down his load for the gift of his own pleasure.

She’d turned him into something he could barely recognize. The weight of it all shamed him. He knelt there, still on the floor as she reclined on the sofa. He felt exhausted.

He yawned, as the tired feeling only seemed to grow and grow. Was he that cliche? Needing to sleep just after cumming? Was it that late already? But then his eyes widened, for just a moment, enough to look up into her smiling eyes with realization.

“Yes,” she said, picking up his wine glass from the table where he’d set it down, “those pills do work fast, don’t they?”

His vision was blurring, looking up at her and then at poor Cheryl, before he could keep his eyes open no longer and slumped sideways in a heap on the floor.

comments and suggestions welcomed!
I like the story very much. The idea of someone being 'broken' and 'developed', and even blackmailed into performing such acts is something I find very exciting. I hope you write more soon.
As an idea for how it develops, perhaps poor Cheryl can be blackmailed into becoming Ms Katy's lesbian pet? Or both 'victims' can become Ms Katy's whores...earning money for her. Or even, Eddy and Cheryl can get married, and Bull can breed Cheryl? Eddy of course needs to continue his development into a total, yet unwilling, sissy slut.
Keep up the good work.
Well given that @edcantor hasn't been on here since 6months after posting this story I can only assume it won't be continued. ☹
(03 Jan 2012, 22:59 )edcantor Wrote: Breaking Him Up
© Ed Cantor 2012
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comments and suggestions welcomed!
I did enjoy this story a lot. I know how much it takes to keep writing, but I do hope you will continue. A great talent. Please write more.

Contributors: bob_masters (2) , edcantor (1) , ltxrob (1)