My Pleasures Were (to Say The Least) Undignified
Copyright© 2007 by Optimizer
Chapter 2
Fantasy Sex Story: Chapter 2 - A classic story, extrapolated to modern times.
Caution: This Fantasy Sex Story contains strong sexual content, including Ma/Fa Fa/Fa Mult Consensual Reluctant BiSexual Heterosexual TransGender CrossDressing Fiction MaleDom FemaleDom Light Bond Humiliation Gang Bang Interracial Oral Sex Anal Sex Sex Toys Exhibitionism Transformation
"... in my case, to be tempted, however slightly, was to fall."
Friday night, though... my resolve could not hold. When Sherry re-emerged, she had big plans. I remained as her for the whole weekend - and a very busy, and expensive, weekend it was. The first thing she did was take a taxi ride back to the store, paying in her customary fashion, and open the safe. (Like many small business owners, I kept a moderately substantial supply of cash readily available for an unexpected crisis.) The second thing she did was go clothes shopping.
My own clandestine purchases had familiarized me with the costs of women's fashion. Later, as myself, I was dismayed but not surprised that Sherry was able to spend nearly twenty-five hundred dollars in the space of four hours at the mall. She'd recruited with ease two guys to help her carry her purchases, and they drove her back to our house.
Before anything else she made sure to procure a bottle of olive oil from the kitchen. She had the guys strip and chose the boy with the largest equipment - perhaps not surprisingly the black one - and took loving care anointing his tool and making it quite slippery. Then she bent over the side of the bed and presented herself for mounting. Anal was everything she'd anticipated. Some pain, of course, but that simply added spice to the affair. Feeling him come inside her ass while the white boy manhandled her tits was inspiring. That was only the introduction; a long night ensued as she modeled several of her new outfits for them. She enjoyed every minute of the process, and didn't mind that many of her brand-new clothes were so quickly torn or stained.
After she'd worn the boys out to the point of uselessness, she idly masturbated herself to sleep. Sherry's dreams are surreal and, of course, highly sexual. An endless stream of porn done by Salvador Dali and David Lynch.
Early Saturday, after a brisk morning romp with her companions, she sent the pair on their way. Her first shower brought to her attention the scandalous lack of a massager, something she resolved to correct as soon as feasible. Then she took a taxi to a local adult novelties store and spent over a thousand dollars. The clerk closed up early, loaded everything into his own truck, and gave her a ride to a nearby Lowe's, then home. She gave him several rides once they got to my house, breaking in a few of her new toys, including the shower massage she had him install.
From the clerk she got an introduction that afternoon to the owner of an area strip club, the 'Corinthian Lounge'. Of course Doug 'Dawg' Simmons hired her on the spot. He was upset about the issue of her lacking any official identity, however. Not out of any moral qualms, of course - he didn't even evince much curiosity about her situation - but apparently tax people paid particular attention to businesses like his. Fortunately this was not a permanent obstacle; it would only delay her start date. Dawg evidently had some extralegal acquaintances that could make such arrangements. Sherry convinced him to front the money for the new identity and take it out of her earnings.
By then it was early Saturday evening. She couldn't be an official dancer yet, but an impromptu 'audition' was held on the center stage and she was a smashing success. There was a certain amount of resentment from the other dancers, but she had clearly won the hearts of the patrons. Sherry enjoyed watching the other girls as much as any of the men there, and her earnings were quickly distributed among their g-strings. (She wasn't heterosexual or homosexual or even bisexual; she was pansexual, omnisexual. Freud had claimed that everything was really about sex. For Sherry, that was literally true.)
She left the club with a particularly rowdy bachelor party. The six guys took her back to the best man's house in the suburbs. She'd never been in a Hummer before, and took full advantage of the ample space to partake of one of the groomsmen on the way. She sat in his lap and the vibration and jostling of the ride added some excitement to the festivities. The stares they drew at a few stoplights were utterly priceless.
Once they arrived Sherry decided she wasn't in the mood for a gangbang. They were fun, of course, but she felt like focusing and take her time. She appropriated the master bedroom and instructed them to send in one man at a time. She lay on the bed, idly toying with the tassels on the throw pillows, a pleasant anticipation building in her loins.
She wasn't surprised that the best man came in first. The house showed that there was a Mrs. Best Man, but he had demonstrated earlier that he was no stranger to strip clubs. And he'd seemed put out that he had to drive, so Sherry couldn't do much with him on the way from the club. She had him sized up as a macho, take-control type... or, at least, a wannabe. So she gave him what he was looking for.
As he paused at the door, sizing her up himself, she put on a half-fearful, half-anticipating expression. A little tentatively, she asked, "So... whaddaya got in mind?" Her tone, her delivery was just so; it said that he would be able to make her do whatever he had in mind, and he would be able to make her love it.
He paused uncertainly for just a moment, then strode briskly toward the bed. "What I got in mind is for you to get your ass off that bed!" She jumped to comply, and he began pulling off her clothes. She didn't directly help him but he didn't run into any trouble. Soon she was naked, standing shyly but with erect nipples and a modicum of color in her cheeks. He turned her about, and slapped her ass appreciatively.
He shoved her down onto the bed so she was bent over it, her rear facing him. His hand insolently explored her pussy, fondling lips and clit. She yelped and shivered but made no attempt to pull away. Her juices drenched his fingers. "Oh, yeah, bitch, that's a nice tight box."
Then, peremptorily, he stepped back and waved at himself. "Your turn. Go." Sherry leapt hungrily to the task, and stripped him as well, but much more respectfully. She started with his shirt and worked down, so she was kneeling in front of him in a most convenient position as she pulled down his underwear.
She started to kiss his tool but he jammed his dick to the back of her throat. She coughed theatrically. (Not sincerely, though; Sherry had total control of her gag reflex.) Then she began sucking and licking, moving her mouth up and down his shaft, letting out little moans and hums of appreciation.
"You like that, huh? Yeah, suck it just like that, you little slut!" He was acting out his own little porno movie, complete with bad dialogue, but Sherry was happy to star in it. After all, she did like it, and she was a little slut. She sucked him harder, looking up into his eyes as she savored the taste. Then she pursed her lips and pulled back, kissing just the head as her tongue flickered across it inside. With a smacking sound she released him. One hand glided smoothly up and down his saliva-soaked cock as she ran her tongue along his scrotum, lifting and dropping each ball in turn. It was his turn to let out a choked groan.
Her other hand ran her nails gently up and down one of his legs. She brought her mouth back to his tool and resumed servicing. He grabbed her hair as he grunted approvingly. "Uuuh, yeah, that's it, you bitch, you whore, take it all!" Sherry found his words exciting, arousing, nasty in the best way. He stiffened and pulled her head back by the hair as his other hand grabbed his cock and began stroking. An instant later his cum began spilling onto her face and breasts. She extended her tongue to catch some of the sticky rain.
Sherry was wet and turned on by the whole experience. His shudders subsiding, Best Man seemed a little sheepish now that his little drama was over. He gruffly thanked her and put on his clothes as she went to the bathroom to clean up. He was gone by the time she returned.
Next in was the groom himself, pushed along by the the other members of the bachelor party. His reluctance was not a surprise - he'd seemed embarrassed by the entire bachelor party and Sherry thought he was probably fairly shy. He seemed to mostly be going along with his best man's plans. More, she had the idea that he probably genuinely loved his bride-to-be and didn't want to cheat on her.
That just made things a challenge for Sherry, though. She didn't care about his feelings except insofar as they involved getting her rocks off. The groom seemed to sense this, too. He stepped forward like a man entering a she-bear's cave. "Look, really, no offense, but I'd rather just..."
"Shut up," she snapped. "Get over there by the bed." Best Man wouldn't have recognized her; the submissive toy was gone, replaced by a forceful dominatrix. The groom meekly though apprehensively obeyed as Sherry marched to the closet.
She searched for a moment and came out with several neckties. Groom's eyes widened as she stalked toward him but the look in her eyes kept him frozen. "On your knees!" she barked, and he complied. Roughly she hauled his arms up and deftly tied them to one of the short posts at the foot of the bed. A second tie went around his neck as a leash.
"Now, let's see what I've got to work with." He tried to mumble some words of protest as she began to take off his pants but again her glare quelled any actual rebellion. Her hunch was confirmed as his dick was freed; he was getting hard. "Yeah, I figured you were whipped," she sneered, giving his dick a pinch. He looked away from her but his cock stiffened further in her hand, as if it was eagerly admitting the charge.
She deftly stripped him from the waist down. She stepped in front of him, legs spread. and grabbed his head by the hair. Bending over, she dragged his red-flushed face to her feet, his arms straining and stretched. "Worship me. Now."
He balked for an instant, and she icily hissed "Now!" once more. Groom commenced licking her toes and rubbing his face on her feet. She was almost dripping with the intoxicating power she felt. A few guiding tugs on his 'leash' and he started to gradually work his way up her legs.
Once he reached her thighs, she lost patience and directed him insistently to her crotch. "You should know what to do. Get to work!" He began mediocre cunnilingus, but Sherry would have none of that. "Get in there and lick boy!", she commanded imperiously. At that, he started pleasuring her in earnest. He wasn't particularly skilled but she was direct and insistent about what she wanted and soon enough he was doing a creditable job. Without for a moment diverting attention from the experience at hand, she amusedly reflected that she was probably doing his bride a favor.
It went on like that for some time, Sherry being in no hurry. Eventually she came, quietly but very intensely, only a sharply-drawn breath indicating the violence within. He might have heard her, or sensed the tremors - he began to slack off. But a firm hand yanking his head forward restored his vigor. Once the climax had fully passed, she released her grip and let him pull back.
His dick was rock-hard, waving gently in the air as he caught his breath. She bent over and stroked it with just her fingertips. He froze and the tip swelled... Slap. "Not yet, you pansy. I'm not finished with you."
She loosed him from the bedpost and used his leash to drag him onto the bed. First one hand, then the other, was lashed to the headboard. His apprehension grew visibly when she constrained his legs, too, in a spread-eagle arrangement. He tried to sputter an actual protest as yet another necktie was formed into a gag, but by then it was too late.
His struggles to free himself only increased his anxiety as Sherry ambled unconcernedly to her purse, since her knots held fast. But actual terror filled his eyes when he saw what she pulled out of it. She began strapping a dildo onto her crotch, finding his muffled shrieks terribly cute. It was rubbery and flexible, with a longish base that would offer her pussy excellent stimulation during its use. She'd been wanting to try it out all day.
"You don't have a choice about this, boy. But if you quiet down, I promise to use this," she teased, waving a tube of lubricant in her hand.
Once that sank in, he lapsed into silence, save for the racing breath through his flaring nostrils. As she approached she noted that drops of sweat had broken out on his forehead. His tool had deflated markedly, but not completely, she was pleased to see. She sat down on the bed next to him and, with a superior expression on her face, began masturbating him. In no time he was stiff again; his eyes kept being drawn to the phallus wobbling slightly in front of her hips.
"Yeah, that's right, you've probably even fantasized about this, right? Being humiliated, being totally owned?" The throbbing of his prick showed her words struck home. "Does she know? Is she into that?" His downcast eyes gave her the answer. "Didn't think so." If anything, his embarrassment seemed to excite him more. "Oooh, you're getting wet..." Drops of fluid had started emerging from his meatus.
She stood and, as he stared, she drizzled lube onto the shaft at her crotch. She made a show of spreading it around, then climbed onto the bed between his legs. Groom was breathing very fast now, and his muscles strained against his bonds fruitlessly. Her hand guided the tip of her instrument to his anus. She left it there for a few seconds, milking the tension. Then she gradually pushed forward and slid it inside. A muffled moan escaped from Groom as she did so.
"You even sound almost like a girl," she sneered. "I do that, too, when a real man takes me in the ass." She started to move, slowly, back and forth. "Better relax down there, or this'll hurt."
Somehow it didn't seem to be hurting him - or at least, the pain was being outweighed by something else. His cock waved ineffectually in the air as she thrusted; she was careful not to give it any direct stimulation. But one hand snaked forward under his shirt to pinch his nipples. He didn't seem to experience that as pain, either. By now, she knew, his balls would be aching with pressure. He'd been feverishly on edge for almost half an hour now without any relief.
For Sherry's part, she was thoroughly enjoying the exquisite rubbing on her clit as she worked him mercilessly, and revelling in the domination. Her own orgasm arrived, and she tweaked his cock as she began ramming into his ass as hard as she could. His own climax was practically a seizure, shaking the bed. She was impressed with how far his cum sprayed up onto his torso, staining his shirt.
When all was done, she unstrapped the tool and left it inside him. Then she untied one of his hands, and ordered, "Clean that up. And yourself. And send in the next one." She rolled off the bed as he began to untie himself, inspecting the dressers and cabinets for anything useful. His face burned with obvious shame as he went to the bathroom holding the dildo. In a few minutes he was dressed, and he left without a word.
The next groomsman was tall and skinny and not nearly as fetishistic, which suited Sherry just fine. She got things going with a minimum of preliminaries; her pussy needed some serious plumbing. They fucked happily on the bed, with her on her back this time. He rode her high and hard, and kissed her deeply as he pounded into her cunt. She screamed as she came three times before he finally exploded himself.
Once he'd left, another groomsman came in. He was older and on the short and thick side. There was a vague resemblance to Carl, which turned her on in an odd way. She took charge again, though less forcefully, and had him sit on the bed while she performed extended fellatio. He reacted much as Carl would have - with disbelief, wonder, and in the end almost pathetic gratitude.
The revelry continued through the night in that fashion, the men taking their turns with her - except the groom, who devoted himself to drinking with a vengeance and eventually passed out. At least, that's what Sherry heard; she never ventured out of the bedroom. It was quite late before the exhausted group finally gave up and slept.
"... within I was conscious of a heady recklessness... a solution of the bonds of obligation..."
Sherry was awakened by a frantic hand jostling her shoulders. "Oh, shit, wake up, wake up!" She smacked the hand away and sat up, rubbing her eyes.
"What the fuck is your problem?" she snapped, recognizing Best Man.
"You've got to get out of here. I didn't set the alarm, my wife'll be home any minute. She can't fucking find you here!" Best Man looked worried.
Sherry thought for a moment, then slid out of bed. "Okay, fine. I'll just get a shower and go."
"No, you stupid cunt, it's almost nine! She'll be here any minute! I've got to clean this place up!" He grabbed her arm and tried to drag her toward the heap of her clothes in the corner.
Sherry refused to be budged. Best Man glared in her eyes for an instant but then froze as he met what Groom had encountered the night before. His hand fell away from her limply.
"I'm covered in cum. I don't mind that, but when it dries it itches. You clean up, whatever, I don't care. But I'm gonna take a shower." Best Man stared desperately after her as she strode unhurriedly to the bathroom.
She peed, and then took her time in the shower. It was not out of any malicious impulse, she was simply indifferent to anyone's desires unless they matched her own. Cleaning out her vagina was both necessary and fun, and Mrs. Best Man apparently enjoyed shower massagers, too.
When she turned off the water she heard someone outside the stall. She opened the glass door to reach for a towel and beheld Tall Groomsman vomiting into the toilet. She stepped past him and dried herself off. He finished and wiped his mouth with the back of his hand and looked up at her miserably.
She was wrapping her hair up in a towel as she remarked, "There's another bathroom, you know."
"Occupado. Jerry's in there. I told him to take it easy on the tequila." She vaguely remembered that had been Groom's name. Tall was hovering over the toilet, as if waiting for more.
"Guess you should have, too." She located what looked like Mrs. Best Man's toothbrush and went to work.
Apparently satisfied he was done for now, he sat back on his haunches and grabbed some toilet paper. "Hell, I've drank more'n that before. Don't even have much of a headache. I hope I didn't catch what my kid had..."
Sherry left him in the bathroom and walked out into the bedroom, where Best Man had tossed the dirty bedclothes in a corner and was frantically making the bed with new sheets. He shot her a murderous look as she began putting back on what little clothes she had been wearing. Skimpy panties, a short dress, and some shoes comprised the entire ensemble, so she was dressed, though hardly decent, in seconds.
Best Man had just started pulling the comforter onto the bed when a low hum thrummed from somewhere else - the garage door opening. "Fuck fuck fuck!" he cried. "Look, get out the back, I got Don, he'll give you a ride." He started bustling her down the hall.
Now that Sherry was clean, she didn't mind leaving, even in a rush. A confrontation would be tedious and possibly even annoying. Their haste was in vain, however, as two women came into the kitchen from the garage as they tried to pass by. One of them called out, "Tell Jerry to hide! We're just gonna..." Sherry's presence finally registered, and she trailed off.
There was a tense pause, and stormclouds gathered on both women's faces. "Who is she?" the other one demanded frostily.
"Uh, honey, this is..." Best Man fumbled for words.
"I'm Sherry." She smiled. "I was just leaving." It didn't mollify them. She had seen hints of this before. Women tended to get defensive of their men in her presence. Though, certainly, the present circumstances didn't help.
"What the fuck is she doing here?" Mrs. Best Man shouted. "What is she, a stripper? A hooker? You said it was just going to be 'the boys', not..."
"I'm not a stripper yet." Sherry interrupted. She realized she could lie at this point, and possibly smooth things over. But she was getting bored and she just did not care what happened after she left. "Like I said I'm leaving now anyway." She turned to Best Man. "Where's Don?"
"You're goddamn right you're leaving, bitch," spat out Mrs. Best Man. She couldn't seem to decide who she wanted to glare at more, Sherry or Best Man.
"Where's Jerry?" asked the other woman, apparently the bride, in a tone that foretold doom. "If he fucked you, I'll kill him. And you," she pointed at Sherry.
Now she was not bored but actually irritated. "Shut up. He didn't fuck me," she said as she rummaged in her purse. "You might want to ask Jerry where this's been, though." Then she tossed something underhand at the bride, who caught it reflexively. Then she dropped it in shock as she recognized the strap-on. She looked back up at Sherry with confusion and mounting horror.
"Go ahead, keep it," Sherry smirked. "Might come in handy with him." As she'd expected, that was a conversation-stopper, and she was allowed to depart unhindered.
Don turned out to be the Carlish guy. She had him drop her off at a nearby mall. She breakfasted in the food court, and got in some shopping time. At noon the court was much more crowded. Her food was purchased by a store manager on his lunch break, who ended up taking the rest of the day off and driving her to a nearby hotel.
Regrettably, though, his reach exceeded his grasp, so to speak. Inside of an hour he was too tired to continue. Sherry donned a swimsuit she had bought at the mall (that was right on the borderline of legal) and went down to the pool to 'advertise'. It was the work of minutes to pick up some travelling businessmen and she moved between three rooms as the afternoon proceeded.
By Sunday evening, though, Sherry was feeling more than a bit queasy. She concluded that the vomiting groomsman had not had a hangover after all. Given the volumes of bodily fluids she'd exchanged, infection was practically inevitable. In her usual selfish manner, she did the only logical thing - she returned home and changed back to me, intending to leave me to suffer through the symptoms. But as the wracking pains of the change subsided, I realized that I felt fine. I was tired, but I wasn't nauseous.
Later experience has borne out what I theorized then - a side effect of the transformation somehow eliminates diseases. I'm uncertain as to the mechanism. Perhaps some aspect of the change kills germs. Or perhaps being sick isn't part of my 'self-image'? However it works, that little byproduct wiped away my last major worry about Sherry's lifestyle, the last hurdle that might have kept me from my current predicament.
"... the situation was apart from ordinary laws, and insidiously relaxed the grasp of conscience..."
Monday the store was closed as I cleaned the house, laundered the sheets, and attempted to organize the rooms for their new second tenant. I was hooked, being Sherry was intense and exhilarating and irresistible. I knew that I would be Carl only part of the time from now on.
Monday night saw Sherry in a photographer's studio doing some promotional shots. Dawg had called and sent her there - he was spending a goodly amount on advance publicity for the debut of 'Sherry Sweet'. He knew a sure thing when he saw it.
The shutterbug was a guy in his forties who was apparently a friend of Dawg. He was black, and a veteran of some kind; she didn't really care about the details. His girlfriend was there, watching the shoot; she was also a dancer at the club. Sherry enjoyed the process, posing among a pile of pillows and cushions in various outfits and assorted states of undress. Imagining guys stroking off to her image was incredibly hot. Eventually, she was naked and masturbating openly, taking pictures that could be used for the club's "members only" website.
The girlfriend had been watching with awe. Sherry was distinctly aware of her gaze... and equally aware that she herself hadn't fucked a woman yet. "Hey, Jesse? Wanna get a few shots of me and Mercedes?"
"Hell, yeah," Jesse breathed. Mercedes didn't need much convincing to join her in front of the backdrop. At Jesse's insistence Sherry put on a thong and a frilly negligee. They started by looking into each others eyes, and then moving close. "Yeah, just like that," Jesse called, "you're in love and you can't hold back anymore."
Sherry ignored him and kissed Mercedes gently on the lips, one hand on her shoulder. She was a thin black girl, but full-chested with a wonderful caboose. Her hair was straightened and lightened to a tawny brown. She wore a pink cutoff t-shirt, jeans, and sandals. Sherry thought she looked delectable. Mercedes was breathing faster, now, as she leaned in for a hug and a longer, slower, juicier kiss. Sherry reached forward and pulled the other girl's shirt up over her head. The camera clicked wildly.
She leaned forward and nuzzled the offered breasts. They were implants, of course - few skinny girls could have such a bosom naturally - but they felt wonderful, and the stiff nipples tickled her face and lips and, as Jesse took shot after shot, tongue as well. Mercedes was trembling, unsteady on her feet, her eyes squeezed shut.
Sherry stepped back and bent forward, undoing the other girl's jeans. The dusky girl remained still, eyes closed, but she spread her legs slightly to help as the brown-haired beauty eased the pants down. Mercedes was wearing a red thong that flashed invitingly as she stepped, one leg at a time, out of the pants.
Sherry stood up, and Mercedes opened her eyes. She reached forward and lifted the negligee off as Sherry raised her arms, presenting her own bosom for best display. The girls moved close, kissing and embracing. Sherry found Mercedes' soft smooth skin to be eminently touchable, and her full lips felt too wonderful on her own.
Jesse had fallen silent. It was clear that no direction was needed. Mercedes was fondling Sherry's breasts now, and the girls sank down gently to lay upon the scattered cushions and pillows. Sherry eased her hand down between Mercedes' legs and deftly slipped past the strip of fabric. The dancer was quite wet, and she squirmed, moaning through the kisses as Sherry explored her pussy. Sherry commenced gently humping Mercedes' leg through her thong, voicing deep moans as well.
The moans peaked - just shy of screams - as the girls both experienced passionate orgasms. But there was no slowdown as Sherry helped Mercedes remove her thong. She lay on her back, propped up on an overstuffed pillow as Mercedes' head dipped between her legs and began to lap at her sopping cunt. The sensations were enchanting; a girl really did know what a girl liked. Sherry admired what she could see of the dark-skinned body for a few moments, before the exuberant slippery probing at her lips and clit demanded her full attention. She yelped joyfully and rode the surge of excitement to a quick series of climaxes.
The stripper came up with a pleased expression on her face, that Sherry quickly showered with kisses. The smell and taste of herself on the other woman was piquant and provocative. She had to taste the other girl's musk at once. She laid Mercedes onto her back and, with easy, acrobatic grace, flipped herself about to enable them to 69. She buried her face in the girl's shaved and succulent pussy. There was a hint of stubble - not something she'd encountered before - but it made a nice contrast to the smooth slippery convolutions of her labia and channel. She loved the contrast between the dark skin of the labia and the pink sweetness within them.
Matters continued like that for some time, each girl exploring the other intimately. No words were needed as they coaxed repeated ecstasy from their conjoined flesh. The first actual sentence in over an hour was Jesse, hoarse with lust, saying, "That's it. I don't have any more film, or cards." Sherry had forgotten he was even there. Mercedes had consumed her total attention.
And the pair had obviously consumed Jesse's attention. His pleading expression made Sherry giggle and it took her a few moments to compose herself and invite him in with a wave. Scarcely another moment passed before he had dived onto the haphazard softness they were playing upon. Mercedes got to work on stripping his lower half while Sherry took charge of the upper half; she was slower because it was more difficult to pull off his shirt while kissing him.
The contrast was striking and enticing. Jesse was urgent, forceful. Mercedes was passionate, too, but the dynamics were different. Not exactly less selfish, but less... using. More aware of what Sherry wanted. Of course, what Sherry wanted from a man was generally that very male aggression, so in practice she got what she craved. That was the case now, as in short order she settled onto his dick with a sigh while Mercedes sat on his face. Her hips moved in sinuous flow while she kissed and stroked the other girl.
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