Caution: This BDSM Sex Story contains strong sexual content, including Ma/Ma, Drunk/Drugged, NonConsensual, Reluctant, Shemale, TransGender, Fiction, BDSM, DomSub, Humiliation, Rough, Sadistic, Snuff, Anal Sex, Analingus, Cream Pie, Oral Sex, Body Modification, Prostitution, Transformation, .
Desc: BDSM Sex Story: Chapter 1 - A most unusual brothel, both in its staff and its clients. Run by the beautiful, ruthless, Maitresse Marie, this house of ill repute is in the business of changing men into the sissies they long to be, even if they don't know it yet.
It was a most unusual brothel, highly specialized in both its cliental and in its performers. All will be revealed. Read on.
“Who do we have coming in today, Cheri” the tall dark haired woman asked as her assistant pranced into the office.
“Three gentlemen from the insurance convention, two senators, the CEO of that credit card company who comes in every month, and a movie producer,” the slight blond replied. She was about 5 feet tall, perky, and cute as a button. She was a complete contrast to her boss, who was six feet four inches tall with big tits, a narrow waist, sleek muscular legs, and shapely ass.
“And we’re ready?”
“Yes, Maitresse. Ready as always.”
“Who’s up today?”
“Carmen, Rose, Phyllis, and Vivian.”
“Excellent. I want those men completely satisfied.”
“Of course. That goes without saying.”
“Well, I’m saying it anyway. And if they aren’t I’m taking it out on you, dear,” the tall woman said, standing and looming over the young woman.
“Y-y-y-yes, M-m-maitresse. I’ll m-m-m-make sure of it.”
“Yes, I think you will,” the brunette said, smiling. “Now come over here and give me some sugar,” she added, pursing her lips.
Cheri, quickly pranced around to the other side of the desk and planted a passionate kiss on the offered lips. Maitresse Marie grabbed Cheri by the waist. Cheri didn’t resist as Marie pulled her into a powerful embrace. Soon Cheri was in the familiar position of sitting on the Maitresse’s lap, and she could feel the characteristic bulge indicating that Maitresse was interested in more than a little tonsil hockey.
The kiss continued until Maitresse Marie broke it and gave Cheri a meaningful look. Cheri knew exactly what that look meant and slipped off her owner’s lap and onto her knees. Marie hiked her micro mini up around her waist and spread her legs. Between those muscular, yet aesthetically pleaseing, legs lay a monstrous cock – 13 inches of hot, hard, she-dick that already glistened at the tip with a bead of pre-cum. Cheri’s tongue flicked out and swiped the drop of spunk leaving a coating of saliva in its wake. She moaned as her taste buds registered the salty tang. Cheri knew she would have a belly full of it shortly.
Gripping the base of Marie’s massive missile, Cheri began working the head and shaft into her mouth and throat. Up and down she bobbed, drooling copiously, her hands distributing the saliva over the entire surface of the thick cock, and on each stroke more and more of it disappeared until she felt her lips touch her fist at the bottom of a stroke. She removed her hand and, with a jerk of her head, swallowed the last three inches of cock shaft. Marie placed her hands on the back of Cheri’s head and held it in place, enjoying the feeling of Cheri’s throat spasming around the mighty cockhead buried there. Marie let Cheri come up for air, briefly.
“Please fuck my face, Maitresse,” Cheri gasped, as she always did.
Marie said nothing. Cheri opened her mouth and swallowed the huge dick again. Marie gripped Cheri’s head and began to slowly move it up just far enough for Cheri to gasp a breath and then back down. At no time was there less than four inches of cock in Cheri’s face.
Someone knocked on the door.
“Come in,” Marie ordered.
“Some new candidates have arrived, Maitresse. You asked to be informed,” said another petite blond who was, as was Cheri, naked except for panties and thigh high stockings. Blonde number two watched with rapt attention as Maitresse continued to use Cheri’s throat as a fuck sleeve without missing a beat.
“Very well. Instruct Caroline to hold them in the processing area and I will be down shortly.”
Marie grunted and came directly into Cheri’s gullet. The little blond couldn’t hope to swallow the flood of spunk spewing from her owner’s massive pole, and it backed up quickly until it shot from her nostrils and from between her lips despite her valiant efforts.
“Come here and help this cum slut,” Marie said, pointing to her crotch.
“Yes, Maitresse,” came the instant and enthusiastic reply.
Moments later two little blonds were happily gobbling cock snot, each licking and swallowing all they could find. Cheri got most of it, of course, but her cohort got a fair amount and seemed well satisfied to get a taste of Marie’s bounty.
“Enough,” Marie said, pushing the little sluts away from her crotch. She stood up, smoothing her skirt as she strode to the doorway and set off down the hall toward the receiving area. A new shipment was in and she needed to see to its disposition.
It was a short walk down a hall, through a locked door, and down another hall into an unadorned room where three young men were standing bound and gagged. They were naked. Attending them were a pair of beings who looked a lot like Maitresse except one was black and the other had pale, freckled, skin and flame red hair. Both were tall with muscular yet very attractively feminine bodies barely hidden in leather vests and shorts. Only the tell tale bulges in their crotches gave them away. Like Maitresse, these bitches were shemales.
Puzzlement and fear radiated off the young men -- you could almost see it rising from them like heat waves in the desert. They had been drugged at a local bar the previous night and when they woke up they found themselves hooded, naked, and bound. They had been driven to this place and herded into this room. They squinted against the sudden glare as their hoods were removed. They had no idea what was about to happen to them.
“These look wonderful. Not too tall or too big. Not much in the dick department either,” Maitresse said, chuckling. The two attendants chuckled as well – it was always a good idea to laugh at Marie’s little jokes. Besides, they thought her remark was genuinely funny.
“Well, boys, I expect you wonder what’s happened, eh? A bit confused? Maybe a little scared? Good. You should be. You’re about to start a new life. And in case you were thinking that mummy and daddy were going to come and rescue you, think again. They’re the ones who sold you to me. I am Maitresse Marie. You will not speak to me unless I give you permission, and when you do speak to me, you will call me Maitresse. I own your sorry asses and if I decide you are untrainable I’ll snuff you like a spent match,” she added, snapping her fingers in front of their faces.
“You’re about to be transformed into pretty little whores who live to provide pleasure to my clients. You see, I run a very special brothel catering to a specific set of tastes. Unfortunately I tend to wear out my ‘ladies’ and need a constant supply of new ones to train as replacements. That’s where you come in. You’re about to start a strict training regimen. If you make it through that we’ll see about the next step. If you make it all the way onto the team your own parents won’t recognize you, although your fathers will be glad to come and fuck your little brains out.”
“OK, ladies, you know what to do with ‘em. Take them down stairs and clean them out, then let’s start the training. I’m guessing none of these little twats has ever sucked a cock before – at least not a full grown one, so let’s start with that. If any of them bites you we’ll just go ahead and remove all of its teeth and have our house dentist come in and fit it for a set of dentures. Everybody likes a good gum job,” Maitresse added with an evil laugh. The poor boy in the middle of the trio pissed himself. All three of the shemales laughed at him. One of the others started to cry causing more laughing.
“You little girls need to learn how to suck cock really fast because if you don’t you’re going to get your balls stomped on, and I am not kidding,” Maitresse said, smiling a secret, evil, smile. She knew what the eventual fate of their balls was going to be and it gave her a great deal of pleasure to keep that knowledge from these poor unfortunates for as long as possible. Of course it was also possible that one or more of them would beg to have their balls cut off for her pleasure.
“Go!” She commanded and her minions dragged the frightened young men out of the room.
“Yes? What is it?”
“You asked to be informed when Cynthia was ready, Maitresse. Madame Sydni says it’s time.”
“Thank you sweetie,” Maitresse said, smiling. She planted a kiss on the messenger’s forehead, and the young thing curtsied before dashing out of the room on another errand.
Marie set off down the hall in the opposite direction from the one that the three new “recruits” had been taken. Cynthia was a project that had been percolating for about seven months. Intense hormone therapy, breast and buttock implants, and rigorous training had brought her to the point of no return. Cynthia was about to give up her testicles. Marie stepped into a sterile looking white room – a small surgical center – where another of her minions, Sydni, was waiting.
“So, Sydni, you say Cynthia is ready to transform?”
“Yes, Maitresse Marie. She has been begging for this for the last week. I think the little tart means it.”
“Good. Let’s get it done then.”
Sydni snapped her fingers and a door opened, allowing Cynthia to enter. She (for that is how she now thought of herself) sashayed into the room, smiling and giggling like a schoolgirl on holiday. She stopped when she saw Marie, and dropped to her knees, her forehead touching the floor.
“Crawl to me girl,” Maitresse Marie growled.
Cynthia complied, crawling to Marie and, unbidden, covering her feet with kisses.
“You desire to complete your transformation then, girl?”
“Yes, Maitresse,” Cynthia said in a reverent whisper.
“Good. Get on that table over there.”
Cynthia scrambled to her feet, stripped herself naked, and climbed onto a table in the middle of the room.
“On your knees girl and spread your legs,” Sydni ordered.
Cynthia quickly complied. Her nutsack hung down between her thighs. But not for long.
“Numb her up, Sydni. We don’t want her to jerk or scream.”
Sydni went to a nearby cabinet and got out a syringe and a small bottle of clear liquid. She filled the syringe with the liquid and walked to the table where Cynthia was kneeling, her whole body trembling in fear and anticipatory excitement. Her cock was stiff and she made little whining noises in her throat.
“This is going to sting a bit. Stay still and don’t complain or you’ll earn yourself a trip to the punishment room,” Sydni said, grasping one of Cynthia’s butt cheeks in one hand and pulling it aside to provide a better angle for her needle. She stuck it into Cynthia’s scrotum and pressed the plunger. Cynthia twitched once and gasped but that was all. Sydni refilled the syringe and injected Cynthia twice more, once on each side of her nut sack.
“There. Five minutes from now that sack should be numb and ready to be removed,” Sydni said.
“Prepare the device,” Maitresse Marie said.
“It is ready, Maitresse,” Sydni said, retrieving a strange looking metal object from a nearby autoclave. It was about 18 inches long and looked like a pliers with three handles. Anyone who’d grown up around livestock would recognize it as an emasculator, a piece of equipment used to castrate bulls or geld horses.
Maitresse Marie put on a pair of latex gloves. She took the emasculator from Sydni and examined it closely, a satisfied smile on her lips as she contemplated the completion of another project. She wondered whether or not one of the three newbies brought in tonight would eventually beg for similar treatment.
“I think she’s ready, Maitresse,” Sydni said. “See?” She added, flicking Cynthia’s nuts with her finger nail and getting zero reaction.
“Excellent. Hold her in position.”
Marie stepped to the table and, with Sydni’s help, she placed Cynthia’s ball sack in the jaws of the emasculator.
“Remember, Maitresse, we must leave the clamp in place for three minutes to ensure complete hemostasis.”
“I know,” Marie snapped, “this is hardly my first.”
“Sorry Maitresse. I just don’t want anything to go wrong. You’ve worked so hard to bring Cynthia to this point.”
“Your eye for detail does you credit, Sydni. Now, let’s get this (grunt) done!”
So saying, Marie closed the emasculator, simultaneously cutting off Cynthia’s testicles and crushing the spermatic cord. She left the device clamped in place to achieve the required three minutes waiting time to make sure Cynthia didn’t bleed to death. There was a small amount of blood which dripped onto the white sheet covering the table. Cynthia hadn’t moved an inch during the process, but she was trembling. Her cock and nipples still quiveringly erect.
Maitresse Marie went around to the head of the table and took Cynthia’s head between her hands, Marie kissed her deeply. Cynthia moaned into her owner’s mouth. Being kissed by the goddess was an incredible honor.
“Brave little slut puppy wants to be a real woman. Well, at least you’re no longer a male. Maybe we’ll give you a cunt. What do you think slut puppy? Would you like a nice tight little cunt for all the clients to fuck?”
“Whatever Maitresse desires is what I most want, Maitresse,” Cynthia whispered. “Even my very life.”
“Nicely put little slut puppy. You are right of course. I will decide what happens to you. In the meantime you will heal from this wound and resume pleasing my clients. How long again Sydni?”
“Before she can be back on the job, Maitresse? I’d give it five or six days, anyway.”
“Very well. See that she is properly cleaned up. Have her balls sent to the chef. I think I’d like some Rocky Mountain Oysters for my dinner.”
Marie left the room, whistling a little tune and in a generally happy state of mind.
In spite of the ball draining orgasm she’d had in her office, Marie was still horny. Chopping the balls off a sex toy always made her cock hard. But Marie didn’t want another blow job. She wanted to fuck and there were a lot of holes available to her at any time of the day or night in the Bizarre Brothel. She briefly thought about breaking in one of the newbies, but quickly discarded that idea. Until they had been prepared, taking on Maitresse Marie’s cock was a terminal experience. She was horny but not in a killing mood.
Back in the office she punched a button and Cheri answered, perky as ever.
“I’m horny. Get in here. Bring some lube.”
“Right away Maitresse,” Cheri answered, her voice trembling slightly. She felt the combination of arousal and fear that attended a summons the inner chamber coupled with an order to bring some lube.
Maitresse Marie’s perky little assistant pranced back into the office, set the jar of lube on the massive desk, and stripped off her panties. Her tiny little penis stood at attention. Cheri had been transformed, just as Cynthia had been, two years earlier. Marie had yet to decide whether to take the next step and give the little thing a cunt. In the meantime, she got off on fucking Cheri, who squealed like a little piggy every time Marie buried her massive meat missile balls deep in the little thing’s guts.
Maitresse Marie stood up from her desk and stripped off her skirt and bustier. Her she-cock was fully erect and bobbed up and down slightly as she stepped over to the sofa. conveniently placed against one wall of the office. Cheri was already there, kneeling with her head toward the back of the sofa, legs spread, hands on her ass cheeks holding them apart.
“Good girl, Cheri,” Maitresse Marie purred, “I see you’ve already lubed up your little shemale-cunt for me. Damn, Cheri, I never get tired of this view,” she added as she applied copious amounts of lube to her girl-dick.
Placing the tip of her huge cock against the center of Cheri’s well trained backdoor, Marie moved her hips forward and was rewarded with a gasp from Cheri as the thick helmet of Marie’s she-cock overcame the resistance of Cheri’s tiny sphincter. It was a mystery to Marie how Cheri was able to accommodate her length and girth – that little sissy-cunt seemed far too tiny to accept Marie’s endowment.
“Ahhhhhhhhhhh ... still tight as a virgin,” Marie cooed as she pressed forward, pushing more and more of her tumescent torpedo into Cheri’s colon.
“Ooooooooo ... thank you Maitresse ... please ... put it all in me Maitresse...” Cheri gasped as her sissy-cunt strained to accept the giant stalk that hung between Marie’s muscular thighs. Even though she’d done this hundreds of times, Cheri never tired of the feeling that being fucked by Maitresse Marie created. Cheri had been here four years. She could barely remember a life before being Marie’s pet. Whatever that life had been it was nothing compared to the joy she experienced every time Maitresse noticed her, or, better yet, used one of her fuck holes for her pleasure. Cheri prayed that she would be given a real cunt so that she could offer it to her Maitresse.
“Fuck ... that’s tight...” Marie gasped as she felt her balls press against the lightly scarred flesh that marked the place where Cheri’s little nut sack had once dangled uselessly from between her legs. She gripped the tiny thing’s hips and began to saw her prick back and forth through the tight grip of Cheri’s sphincter. Maitresse Marie was not after a quick orgasm. She relished the feeling of plowing her favorite slave’s sissy-cunt and wanted it to last.
“Oh, Maitresse ... you fuck this little slut puppy so good ... thank you Maitresse ... may this little slut puppy whore play with her clitty Maitresse?”
“No, slut puppy. Maitresse will play with it. You are not to touch it, understood?”
“Y-y-yes, Maitresse,” Cheri responded. She feared punishment for her impertinent request. What happened next completely shocked her.
Marie lubed her right hand and reached under the belly of her little service animal and engulfed the thin little spike that stuck out from between Cheri’s legs. It was only about 3 inches long, erect, and useless for fucking. It did make a nice little morsel to suck on, and Marie had sampled it several times. She enjoyed Cheri’s gasp of pleasure and surprise as the little puppy felt her sissy-clit being expertly stroked by the one who could decide her ultimate fate with a word.
“Oh ... oh ... oh ... Maitresse ... oh ... oh ... oh,” Cheri cried out in pleasure.
Marie began to seriously stroke her big dick in Cheri’s asshole while simultaneously frigging Cheri’s little penis. Cheri helped by rocking her hips back and forth alternately impaling her ass and Marie’s fist. Cheri was in heaven. She was being used by the one whom she worshiped and feared above all others. And Maitresse was giving HER pleasure. This didn’t happen often. Maitresse must be in a good mood today, Cheri thought. And then coherent thought became impossible as she was engulfed by a wave of pleasure.
“Don’t you dare cum yet, bitch,” Marie hissed in Cheri’s ear. “Maitresse always comes first!”
“Yes, Maitresse,” Cheri groaned, trying as hard as she could to stave off the climax that had been building inside her since she first felt her sissy-cunt opened by Maitresse’s fantastic cock. Cheri still had a prostate and Marie’s big dick was hitting it flush on each inward stroke. That combined with her heavily lubed fist gripping Cheri’s tiny little love muscle was almost more than the little slave could take. But she was well trained and knew what would happen if she came now, before Maitresse had unloaded in her.
Cheri focused on using her inner muscles to maximize Marie’s pleasure. That focus kept her from going over the edge and earning the wrath of one who, to her, was a goddess. She would never willingly, or on purpose, do anything to displease Maitresse Marie. Worship is too tame a word for what Cheri felt toward the one who had given her everything.
Marie was surprised that the little chippy hadn’t blown a load. Marie was an expert at using her cock to make slaves give up their pathetic little squirts. Cheri was fighting to obey and Marie could tell that the little slut was working as hard as she could to give her owner pleasure. If Marie had retained the ability to love, she would have loved little Cheri.
“Tell ... me ... what ... you ... are,” Marie whispered in Cheri’s ear; each word punctuated with a hammer stroke of her enormous cock.
“This ... one ... is ... a ... worthless ... piece ... of ... shit ... Maitresse ... a ... set ... of ... fuck ... holes ... for ... your ... use.”
“Oh, Cheri, you say the most beautiful things,” Marie said, chuckling.
“Thank ... you ... Maitresse,” Cheri gasped, her control now hanging by a thread.
“Do you want to cum little cunt?”
“Y-y-y-yes, Maitresse. P-p-p-lease Maitresse.”
“When you feel my cum shooting into your dirty little sissy-cunt, you can cum. We will cum together.”
“Ohhhhhh ... yessssss ... Maitresse ... Thank you ... Maitresse.”
Marie quit talking and began stroking her cock in and out of Cheri like a trip hammer. Marie’s hips were almost a blur. No human should have been able to take such a fucking without being torn apart, but, somehow, Cheri always managed to survive. She did walk funny for days after a drubbing like this though.
“AAAAAHHHHHHHHH,” Marie shouted as she loosed a torrent of semen into Cheri’s bottom. She’d never stopped stroking the poor little thing’s cock.
“MMMMMAAAAAAAIIIIIITTTTTTRRRRREEEEESSSSSEEEEE! I LLLLLLOOOOOOVVVVVE YOOOOOOOOOOOOOU!” Cheri screamed as she came, her tiny penis ejaculating a surprisingly thick rope of cum, quickly followed by three or four more spurts, one after another. Each one made Marie grunt as Cheri’s sissy-cunt contracted around her dick, which was buried to the balls.
Marie wrapped her arms around the little shemale and lifted her completely off the couch. The big woman held her little lover tight and stroked her tiny penis until the spurts became dribbles and then stopped.
Cheri turned her head and Marie kissed her on the mouth. Marie squeezed Cheri with her massive arms once more and then pulled Cheri off her cock and tossed her on the couch. Cheri scrambled off the couch and knelt at Marie’s feet.
“Please, Maitresse. May I clean your cock?”
“Yes, you may, little one. Clean it well.”
“Yes, Maitresse,” Cheri said as she began vigorously licking every square inch of Marie’s big dick. When it was covered with saliva, Cheri once again swallowed it to the root.
“Ahhh ... that’s nice. I think it’s clean enough.”
Cheri gave a final swallowing suck and released Marie’s cock. She lowered her head and waited.
Marie put her hand on Cheri’s head. “Good girl. Yes, you’re my good girl. Look at me,” Marie said.
Cheri looked up, hesitant to make eye contact.
“Look me in the eyes, baby. It’s OK.”
Cheri looked into the eyes of the woman she loved and feared most in the entire world.
“Sugar, I know you love me very much. You’re the best little slut puppy I’ve ever trained. If I could love anyone, it would be you. But I had the love burned out of me a long time ago. I can’t love you baby, but I can keep you safe. You do exactly what Maitresse Marie says every time and you’ll stay safe. You step out of line and I’ll have to punish you. You feel me?”
“Yes, Maitresse. May a slave speak, Maitresse?”
Marie was slightly taken aback. Cheri never asked to speak.
“What is it little one? What do you want to say to Maitresse?”
“Please, Maitresse, forgive me for speaking out of turn.”
“Yes, yes, you’re forgiven. Now what was it. Speak. I don’t have all day.”
Marie tried to sound stern, but inside she was smiling. The little bitch had it bad.
“It doesn’t matter to this one that you cannot love her. She will love you and serve you her whole life anyway. Maitresse has saved her from a life of misery and lies. Maitresse has allowed a slut to find her highest purpose. This one would gladly give up her life to Maitresse, the goddess who owns her body and soul.”
Marie was touched. But only a little.
“Don’t move,” Marie said.
The amazon shemale went to her desk and opened a drawer. When she stepped back to where Cherie was kneeling on the thick carpet, she had a .44 Magnum revolver in her hand.
“Open your mouth, cunt.”
Cheri opened her mouth wide. Marie stuck the barrel of the gun in the little shemale’s mouth and pulled the hammer back. Cheri closed her eyes when she heard the click.
“You mean what you said?”
Cheri nodded her head. A tear ran down her face. She nodded again and sighed.
Marie uncocked the revolver and pulled the barrel out of Cheri’s mouth.
“Good. That is as it should be. Now, little cunt, you seem to have dribbled cum all over my carpet. You’d better clean up that mess or I’ll whip the skin right off of BOTH your ass cheeks.
“Yes, Maitresse. Right away Maitress.”
“And clean yourself out too. I don’t want you leaking my cum all day long,” Marie added.
“Yes, Maitresse,” Cheri said. She scampered out of the room, beaming with pleasure and secure in the knowledge that her Maitresse really did love her.