Reader
Open on Literotica

Simon Sissy Slave Ch. 03

Mr Berne watched with satisfaction as the sissy paraded in the post room. Sissy walked gracefully in high heels. His ballet training made it easy. He knew how to walk like a woman. He had practiced, and he could walk with a book balanced on his head. It gave him poise, and the high heels gave elegance to his calves. The skirt was short enough to look slutty, particulary with the stockings. It was just as Berne wanted. He wanted, not so much a perfect woman, but a slut; a sexy doll to be played with and to entertain.

"Excellent, Simone!" Berne was thrilled.

"If I saw her in the street, I'd think she was a woman!" Even Barry was impressed. "And such a slutty look."

"The wig is perfect too!" Berne added with more approval. "You are almost perfect Sissy!"

"Thank you, Sir!"

It didn't seem to matter that she had no breasts to speak of. The curve of her hips and the way the sissy walked was enough.

"Lift your skirt so we can see your knickers!"

"Yes, Sir!" Sissy obediently pulled up the hem of her skirt, showing her red silk knickers.

"You'll have to learn to keep that cock of yours under control!" Berne remarked concerned.

"Yes, Sir!"

"That is difficult when the fucker is aroused all the time," Barry remarked with disgust, "the fucking slut has a hard on all the time!"

The more Barry hurled such abuse, the more difficult it was for Sissy to control her cock.

"We'll have to think of something to contain it!" Geoffrey chipped in, practical as ever.

"Castrate the fucker!" Barry suggested with enthusiasm. "That'll sort it!"

Sissy's cock throbbed harder, particularly as Mr Berne slid his hand in her knickers and took in his hand. He liked to feel his slave's cock.

"Now, now, Barry" Mr Berne responded, smiling "you must curb your enthusiasm!"

"Well, if you change your mind, " Barry continued, making scissor movements with his fingers, "I'll gladly take a knife to it and cut his balls off!"

Sissy blushed. Her knickers were already getting wet from the pre-cum oozing from her cock as her master massaged the foreskin over the rim of the glans.

"Our slave is better with a cock." Berne continued as he continued to massage it gently, "It is what makes her our slave. You like being our obedient sissy slave don't you Simone?"

"Yes, Sir!"

"Sissy, you will accompany Barry again on the trolly round this morning," Berne instructed, releasing her cock and getting down to work. He wanted to know how well the sissy could carry off being a woman. Would people notice? He wondered.

"Yes, Sir!" Sissy obediently replied

"And Barry, try to curb your instincts, and don't mess up her knew outfit!"

"I'll do my best Mr Berne," Barry responded, with a cheeky smile, "but I can still take my pleasure from the fucker can't I?"

"She is yours to do as you wish with Barry, but I need her unsoiled today!" Mr Berne insisted, and with that Barry and the sissy left; the sissy pushing the trolly.

As they went by the toilets, Barry pulled the sissy in.

"I need a fucking piss first! Leave the trolly here. You're gonna serve as my toilet slave. Now get in."

Barry pulled his cock out at the urinal and began to piss, pints of it, shooting it up the back of the urinal and watching it flow down the tiled wall. Sissy admired the shape and size of her young master's cock, remembering how it felt in her mouth. Its helmet-shaped head was perfect and she liked sliding her wet tongue just beneath its rim, feeling the effect on his throbbing cock. She loved his firm scrotum and the large balls it contained with their master's seed.

"Are you ready to taste my piss, fucker?" Barry asked as he stopped the flow of piss, holding back.

"Yes, Sir!"

"Squat down, and be careful not to spill any on that blouse!" Barry instructed, "Open your mouth wide, and look up, keep your mouth up!

Barry had saved just enough piss to humiliate the slave, and delighted in seeing it fill the sissy's mouth. He filled it once and stopped.

Sissy was disgusted by the taste. It tasted absolutely foul, but she revelled in the humiliation by her young master. Out of all of them in the post room, Barry was the one who seemed to understand instinctively what the slut wanted. He bullied, humiliated, fucked, degraded, demeaned and debased the sissy slave in what had become a mutual compact between them. He was the dominant master, the sissy was the compliant submissive, needing to be humiliated and abused. It made him feel good and it gave her what she needed.

"Swallow it!" Barry commanded, and when sissy had obediently gulped down his golden piss, she opened her mouth to receive more. Barry loved pissing directly into the sluts mouth. "You're my fucking urinal!"

The young master filled the slave's mouth several more times as the sissy drank his piss.

"What do you say to your master, slave?" Barry demanded when he had finished.

"Thank you, sir!"

"Now lick my dickhead clean, slut!"

"Yes, sir!" Sissy obediently and diligently licked her master's cock clean, licking the hole and then sliding her tongue around the head.

"I hope you can taste my piss all day fucker!" the young master insisted, "You should really drink all my piss. I should save it all for you so you don't miss a drop of it!"

"Yes, Sir!"

"OK, fucker, you know what you've gotta do now!" Barry pulled his pants down and turned his arse to the slave, and the sissy crouched down to cleaned her master's anus with her tongue.

"Yes, lick my anus clean! Taste it slut." The young master instructed, "And let me feel that tongue poking my rectum."

Sissy licked and poked diligently with her tongue around her master's anus.

"Oh, yes, that is good slut. You will clean my arse every day. Do you understand? You are responsible for keeping my arse clean!"

"Yes, Sir!"

"Tell me what you are fucker!"

"I am your toilet slave, sir!"

"Good, you are pathetic slut!" Barry sneered.

The trolly round was uneventful even when they entered the open plan offices on the first and second floors. One member of staff observed that they were employing a girl in the post room - the post room was a male preserve. The round was over fairly quickly, and the outgoing post and files were collected and brought back for sorting.

Mr Berne looked Sissy up and down when they returned to the post room, checking her outfit and feeling her cock and balls. He was particularly concerned that she had not soiled her panties. In his examination he took time to finger the sissy's delightful anus.

"I do hope young Barry that you have been careful!"

"Yes, Mr Berne, very careful!" Barry replied with a grin. The taste of the young master's piss lingered in the sissy slave's mouth.

Mid-morning, the tea lady came round with a big urn of tea, biscuits and crusty cheese rolls.

"Oh Mr Berne, you've got a girl working in the post room now I see!" the tea lady observed, "I do hope they are looking after you dear!"

"Yes, she is a pretty thing isn't she Shirley?" Barry said with a grin, quickly devouring a cheese roll and slurping a cup of tea.

After she had gone, Mr Berne expressed his pleasure that if Sissy could pass the 'Tea Lady test' then she could pass anyone's test.

The rest of the day passed uneventfully. The staff for the most part left Sissy be, other than the occasional slap on the bottom from Geoffrey, or Barry feeling her cock up her skirt, which he did often.

At four o'clock Mr Berne finished a telephone call he had received and called Sissy over.

"Simone, there's a taxi outside waiting for you." Mr Berne informed her. "A man will come in a moment to escort you and you will go with him to an apartment in the West End. You will let the guests there do with you what they want! Is that understood?"

"Yes, Sir!"

"Good girl!"

Mr Berne was pleased with how obedient Sissy was. It was quite extraordinary he thought that somebody could be so compliant.

"Try not to be too scared at what they might ask you to do Sissy, and you must be very discreet."

"Yes, Sir!"

At that moment the man arrived to escort her. He was thick set like a club bouncer and wore dark glasses. He handed over a large brown envelope to Mr Berne who opened it to check its contents. Smiling he nodded to the man, and Sissy could see that the envelope contained a wad of money.

She was being sold! Not permanently, perhaps, but she was being sold for sex. That much was clear. Her heart raced and pounded in her chest and her cock was dancing in her red silk panties.

"Go with this gentleman, Sissy!"

The taxi driver discarded the but end of a cigarette as they appeared in the street and the escort opened to cab door for Sissy to get in. He gave an instruction and the taxi set off.

They hadn't gone far before the taxi pulled up outside a block of luxury flats, probably dating from the 1920s, Sissy thought. She knew only the wealthy lived here.

The escort payed the taxi driver and escorted Sissy past a uniformed concierge and into the building. They then took a lift to the top floor apartment, a suite of rooms in a penthouse.

"You're to wait here!" The man indicated a sofa in the large hallway, and then he left her.

Sissy could hear a lot of shouting coming from one of the rooms as she sat waiting. Her heart was pounding in her chest. She had no idea what to expect, but she had suspicions about what was expected from her. Some degree of anxiety kept her cock under control.

Sissy waited for what seemed like ages. Suddenly the door to the room where most of the noise emanated opened and a middle-aged man come out followed by a dishevelled young man whose shirt was torn. He was naked from the waist down, and Sissy could see his stiff cock and his firm balls. The cock looked red and sore, as if it had been beaten. He was being led by a collar and chain like a slave.

The older man was leading the slave across the corridor and into another room and sissy noticed that the young man's bottom had been brutally thrashed, and some of the welts were oozing streaks of blood. The older man glanced at Sissy before closing the door. The noise in the room they had just left again became a raucous din. It sounded like a cattle market.

Then there was some degree of silence as something else was happening in the room. Sissy knew not what, but she was beginning to get a picture in her mind. A scream from the room where the older man had led the slave confirmed Sissy's thoughts. She heard the swishing and cracking sound of a whip followed by another scream. Clearly the poor fucker was receiving another severe thrashing. After several more screams, the room went silent and she imagined the older man finding some other way to abuse the poor sod - perhaps he was fucking him - and a few moments later she heard another scream.

As she listened her cock throbbed and oozed pre-cum. Her heart raced with mixed emotions of fear and longing. Would she be whipped too? And whatever it was the man was doing to the slave, would she get the same treatment? She almost fainted at the thought. Her mind was wild with anticipation. This was what she had read about in the magazines she got from the top shelf of the newsagent but a thousand fold more extreme.

The din in the main room once again reached a crescendo and Sissy heard several screams followed by applause and cheers. The door opened again and another wretched slave was dragged out by another middle aged man. Sissy could see that he had been soundly beaten also. He was a wreck, shaking and sobbing uncontrollable, As the man led him into another room across the corridor, Sissy could now see that blood streamed from his anus. Whatever they had done to him involved his rectum. Had they fucked him so hard that he bled? His anus gaped open. Soon after the door had been closed, she heard this pitiful slave yelping repeatedly as his treatment continued.

The door to the main room opened once more and Sissy was surprised to see that this time it was Mr Simms, The Director, who came out.

"Come this way Sissy," he instructed "it is your turn now! Just do as you are told!"

Sissy stood up and followed Mr Simms into the room. There were around twenty men seated around the walls of the large room. In the centre of the room was a leather whipping bench with straps, and Sissy could see blood stains on the sheet lain underneath it. Some poor souls had been viscously beaten as the men had watched baying for blood. She noticed also that one or two of these beaten wretches were still in the room. One was kneeling and sucking the cock of an elderly man, who occasionally. thrashed him with a cane. Sissy heard the man shouting at the slave "suck harder fucker and make me cum!". Another was being brutally abused by a man who had his fist in the slave's rectum and was viciously pumping it, fucking the poor sod with his arm. The squelching of his arm as it fucked echoes in the room as did the slave's agonising groans. She saw another licking a man's arse, another suffocating with a cock deep in his throat.

Sissy almost fainted at the thought of what might ensue for her and her cock had shrivelled with fear. Then Mr Simms led her to the centre of the room and addressed those assembled.

"Ladies and Gentlemen, thank you for your patience. We now have our final slave on the market this afternoon and I am sure you will agree she is a delight. I can vouch for the fact that she has a delightful cunt-hole. She is a most obedient slave, and as you can see she is a beauty, and she is first going to dance for you. I give you Simone."

As the men applauded Sissy heard music. It was Swann Lake.

"Dance for them slut!" Mr Simms whispered, "Or do you want a dose on the whipping block?"

Sissy, slipped off her high heels and began to dance. She entranced them, flying through the air, twirling, and pirouetting gracefully as if she had wings, and deftly landing as if she was as light as a feather. He body bent in a perfect arch backward and tthen forwards. She danced on the tips of her toes. She landed with the splits and rose up and then she danced in front of each of the men in turn, and with pirouettes she spun like a top before them. Her red silk nickers flashed as her skirt rose up. She was a ballerina. Somehow she deftly removed her skirt and blouse and now danced in just her red silk panties and stockings. The music reached a crescendo and then she deftly fell to the floor, a dying swan. Then there was silence, followed by loud applause. She had stunned them. Some were almost in tears at the shear elegance of it.

"Ladies and Gentlemen, do you want to see her whipped, or do you want to bid for her now?"

"Whip her!" "Whip!" Some of the men bayed for blood. It was clearly what they came for. These were men of importance and prestige who came to this club for one reason, to share their lust for seeing young men, their sex slaves, beaten and abused. It was a secret club for the establishment, where rich and powerful men could play out their erotic fantasies without restraint, where young men were beaten senseless or worse and where their bodies could be used in the most brutal sexual practices. They felt little if anything for the poor wretches who were abused here. They were simply their sex slaves to be discarded, and then when their debauchery was over they would go back to their respectable positions in society. Some might even be judges, hankering after corporal punishment and public floggings.

"Two hundred!" Some had already started bidding.

"Three!" Called another.

The elderly gentleman with slave still sucking his cock, then stood up kicking his slave away and beating him mercilessly with a cane. Then he spoke.

"I suggest we do this the normal way. Of course I can see why some would want to ravage this young beauty in her pristine state. If that is so, then they can bid for her while she is being whipped. If the person who wins the bidding wishes to take her and stop the beating, then that is what will happen. If the bidder wants the beating and bidding to continue then so be it. We follow the usual practice and bid for what we want."



"Whip! Whip! Whip!" A chorus welled up in the room.

"I am sorry Sissy!" Mr Simms said with genuine remorse, "Let us hope it will be brief."

One of the men then dragged her to the whipping block and ripped her knickers off.

The bidders gasped as they saw the beauty of Simone's buttocks, and the shape of her hips. So feminine! Yet still they bayed for blood as the sissy was strapped onto the whipping post.

Mr Simms chose to be the first to whip her. He chose a cane which he wielded deftly but lightly on the sissy's bare buttocks.

Thwack! Thwack! Thwack! The first three strokes landed producing three red lines across the slave's buttocks. Each produced delightful squeals; so delightful the bidders wanted to hear more.

Thwack! Thwack! Thwack! Three more strokes and Sissy's buttocks were criss-crossed with red welts. Each stroke evoking the same delightful little squeals.

"Five hundred!" Sissy heard someone bid, but were they bidding for more strokes or to stop the whipping?

"Six hundred!" She would not know the answer because someone else had now outbid them.

The room fell silent in anticipation.

"Whip her!" the man who made the bid cried as he came forward to take over the whipping.

The bidders cheered and applauded.

The man chose a bifurcated leather strap called a tawse, used by the penal system and in schools in Scotland. The bidders cheered his choice and applauded as he swished it through the air before bringing it down hard on the sissy's buttocks.

Thwack! God it stung! Sissy squealed a bit louder but still the bidders were entranced by it. Thwack! Thwack! Thwack! The man whipped her with the tawse as her squeals echoed in the room.

"Seven hundred!"

"Eight!"

Again the room fell silent.

"We have a bid of Eight hundred!" The elderly man announced. Does the bidder wish to stop the whipping and take the slave? Or is there any other bid.

The room was silent. Sissy waited.

"Nine hundred, and I say the whipping continues for more bids!"

The audience cheered as the new bidder came forward and selected a bull whip. The bull whip was difficult to use but if it found its mark it could severely lacerate the thin skin of humans.

Now a hush descended on the room in anticipation of the first lash. Would it cut the skin? Would the slave scream? They had seen its effect so many times, and seen salves mercilessly beaten senseless with it. The man deftly swung the whip round in the air above his head and it cracked as the tip struck Sissy's buttocks.

Sissy's loud prolonged scream again delighted the bidders and they applauded loudly. They had forgotten the beauty of her dance and now wanted her to be shredded senseless with the bull whip. She was breathless and she felt her heart pounding.

"Please!" she heard herself cry.

"One thousand!" A fresh bidder, "And I suggest before the bidding continues we all have a chance to examine the slave properly. We have seen her dance, but I for one wish to see what her fuck-hole is like!"

The bidders applauded and cheered. Sissy gulped. The bidder came forward with a large dildo and pushed it against Sissy's anal sphincter, which relaxed in anticipation and the object penetrated her rectum with ease. The bidders applauded as the man fucked her with it, thrusting it in and out several times to the delight of the bidders, then he fucked her with it faster and faster, banging it in and out ferociously as the sissy delightfully moaned and squealed in agony.

Another bidder, excited by what he saw, now came forward and fucked her with his hand, pushing his four fingers in with great delight.
"She has a well-trained fuck-hole" he announced.

The bidding war continued now in a frenzy. Some winners wanted to whip her and did so with cane, tawse or whip. Yet others wanted to fuck her with bigger and bigger dildos or with a hand, delighting in the squelching of their hand fucking her rectum, but, most of all delighting in the slave's powerlessness.

"Two thousand" a bidder called, "and I want her fisted!"

The audience applauded once more. Sissy had never been fisted. The first she knew of it was when she saw the poor slave with the bidders arm fucking him, his master's fist deep in the slave's rectum and the slave moaning and writhing in agony.

The man came forward and using gel on his hand and arm he probed Sissy's anal sphincter first with his fingers and then his hand. Then he pushed gently with finger and thumb sliding his hand in up to the knuckles. Sissy felt her anus being stretched as it had never been before. She tried hard to relax. At first her sphincter resisted and squeezed on the hand and then the man eased his hand in past the knuckles. His entire hand was now inside Sissy's rectum as he moved forwards and backwards, slowly. He then formed a fist inside the slave's rectum. Sissy felt the pressure and a aching inside, and he slowly pulled back against the sphincter. Sissy felt like a giant poo was pushing to come out and her anus relaxed and the man pulled his fist free, but then immediately he pushed it back in before the anus could tighten: in and out he pushed his fist past the sphincter into her rectum. Then he thrust his arm in deep almost to his elbow. He pulled it out and pushed it back, repeatedly until no resistance was given and sissy's anus gapped open when he pulled it out. He had broken the slave's arse.

Some of the bidders came closer to look at her gapping fuck hole, and feel the rim with the fingers and see how easy it was now for them to put their fists in.

The bidding stopped and the man who fisted her had won. Sissy was released from the whipping bench and dragged away by the victor, her buttocks were raw and her anus sore. To the cheering of the bidders a collar and chain had been put on her neck and she was led from the room, a slave to be used by her new temporary master. He had won her and now he could use her as he wished.

The man led her to one of the other rooms, and as he did so, Sissy saw one of the slaves being removed from the room. His arse was bloody and his face swollen. Sissy was now led by her master into the room where he laid her over a waist high whipping bench. Immediately he pulled his cock out and thrust it into her sore rectum and fucked her hard, his large cock sliding in and out with ease, but sissy's sphincter was still just firm enough to give him the pleasure he needed.

Slap, alap, slap...he fucked her on and on and on, his hips and balls banging on her sore buttocks.

"You are such a nice piece of fuck meat and you cost me a lot of money!" The man told her as he fucked her, "Now I want what I paid for!"

He pulled his cock free from her rectum and slapped her buttocks hard several times. It stung like mad and Sissy squealed at each slap. The marks of the bull-whip were raw.

This her new master loved. He slapped her again and again to make her her squeal. Then he delighted in fisting her once more. Pushing his fist in deep and the slapping her when he took it out; slapping her and then thrusting his fist into Sissy's rectum repeatedly. Occasionally he squeezed the slave's balls hard and pulled her cock.

Then when the master was finished with her rectum he turned to her throat, thrusting his cock deep in her mouth and fucking it. Pulling sissy's head down hard and holding his cock deep inside her throat until she gagged and gasped for breath. This he did repeatedly until he chest was heaving, gasping for air. Sissy was almost suffocating with his cock as he fucked her throat.

The man was now working himself to a frenzy oblivious to any damage he might cause to the slave. It was simply a piece of meat to him, to be used as he wished for his own perverted satisfaction. He pulled his cock free from Sissy's throat and took a cane to her buttocks with repeated stokes that Sissy lost count of as she squealed and screeched at the pain. Finally, he thrust his cock once more deep into Sissy's rectum and shot his load, gasping and grunting to a climax.

"You fucking whore!" he said finally and left the room leaving Sissy sobbing on the bench.

After a short while, two of the men came and pulled her off the bench and out of the room and took her back into the bidding room where she was paraded for all the bidders to see. She saw the other slaves too, some now being used ad hoc by the bidders to give there cocks pleasure. Even the one with the broken anus was being fucked hard by one of the bidders.

Sissy was dragged over to the elderly gentleman and he soon had her sucking his cock, banging her throat up and down on it. To the man's gratification he grunted to an orgasm and shot his load deep in her throat.

"You dance well and you fuck delightfully! The old man said pushing her away as another of the bidders took her and dragged her to his seat to such his cock. And so she was passed around the room, each bidder taking their turn fucking her throat.

Finally the proceedings came to an end as Mr Simms thanked all the bidders for their attendance and hoped the selection of slaves had fulfilled their expectations.

One by one the bidders left the room until only the slaves remained, exhausted and broken. Sissy had been more fortunate than some who had been severely beaten simply for the pleasure it had given their tormentors. Two 'orderlies' came in and started tending their wounds and one of them checked Sissy's wounds and her anus. She was very sore and it would take time for the welts on her buttocks to die down, but she would be ok. The man who had accompanied her to the apartment now came to take her away. To Sissy's surprise, in the taxi he handed her an envelope.

"By way of thanks from the Boss!" He told her. "You can take the taxi all the way home if you want. It has been paid for."

Sissy glanced in the envelope. She had been paid well.

"It won't be as bad next time!" the man added.

"Thank you!" she said.

"I'll collect you again next time then sweetheart!" the man replied as he got out of the Taxi.

Sweetheart! Nobody had called sissy that.
Log in or Sign up to continue reading!