Reader
Open on Literotica

Simon Sissy Slave Ch. 04

Simon staggered in for work the day after the slave auction, his body stiff and sore. Mr Berne and the others in the post room were shocked to see the sissy's bruised and lacerated buttocks.

Barry's stiff cock betrayed his feelings; whipping and torture excited him. His sadistic nature relished the thought of thrashing Sissy senseless. Sissy was his fuck toy. The more submissive 'Simone' was, the more Barry wanted to hurt 'her'. Simon was a pathetic 'pansy'; a 'poofter'. Yet, every move Simon made was effeminate and sexually provocative - from swinging his hips to the daintiness of his steps - keeping Barry's cock stiff and throbbing in his pants all day.

When Barry went drinking with his mates, they would hurl abuse at those they thought were homosexuals, or 'poofters'. They were the 'scum of the earth', and it was right that they should be punished by law. He and his mates saw them as a kind of human infestation, and the thought of two men having a sexual relationship appalled them. This was the 'swinging sixties' but there were limits.

Poofters loitered around public toilets and in parks like predators, a dirty, seedy affair with a quick bit of buggery behind a hedge. The West End, Barry thought, was teaming with them at night - down dark alleyways, mutually masturbating, sucking cocks, or pulling their pants down for a quick bunk up the arse. Barry's mates called them 'shirt lifters'. Often he read about police staking out parks and public toilets, enticing the freaks with 'pretty boys' as bait. Hundreds of them were prosecuted for 'public indecency' - all sorts, rich and poor alike, illicitly satisfying their wanton 'depravity'. They were forced into the darkness of a 'secret' underworld.

Barry and his mates were on constant alert for them - like bogeymen in the night - with their furtive looks, their language of nods and winks, gestures and phrases. They had developed a sixth-sense for them like a radar system. Poofters were everywhere - an alien species and a constant threat. Anyone different was a suspect, and fair game for ridicule and abuse.

Simone's femininity got under Barry's radar. He would never tell his mates about it. The idea of a 'she-male' hadn't really entered their heads, let alone a fucking slave. Simone was a piece of fuck meat. In any other sense, Barry had no interest in sex with men. Sissy was a 'freak', and he liked to dominate him. Almost everything about Simone was feminine - and the fact that Simone had a cock turned Barry on. He enjoyed fondling it while fucking her arse. It was delightful when soft and exciting when it was hard. He liked squeezing her balls and relished the control of her sexuality. Oh yes, he liked fucking 'her' up the arse, and the sissy's anus was now like a fuck-hole, a cunt. Barry loved his cum oozing out of it. He adored the feel of his cock shafting it. Pushing his cock in the slut's anus was an act of power.

The truth was, Barry had fucked Sissy's anus more times than he had ever fucked a girl. Simon wasn't a 'real man', so that made it different. He also thought his mates would want to fuck the sissy too. Maybe one day they would! He would throw the sissy over a table, pull her skirt up and knickers down, then every real man in the pub could fuck her! His cock danced uncontrollably at the very idea of it. He wanted to make it happen.

"She'll be ok in a few days!" Geoffrey reflected as Barry examined the sissy's sore and bruised anus, probing it with a finger, excited by how easy it was to penetrate. Simon's anal sphincter dilated to the touch.

Of all in the post room, Geoffrey was the most analytical and the least emotional. Sissy's wounds would heal because they were superficial, he concluded.

Barry wasn't that interested in whether or not the slut's wounds would heal.

"So, he fucked you with his fist, Slut?" Barry asked savouring the thought as his cock throbbed. "Fucking hell, his whole fist up there!"

Pushing three fingers deep into Sissy's rectum, Barry wondered what fisting felt like.

"Yes, Sir!" Sissy confirmed.

Barry noted with pleasure how the slave's anal sphincter reflexively relaxed as he probed it. It was now a fuck-hole to serve a master's cock. Barry felt the slave flinch as his fingers poked deep into his rectum. He imagined his entire fist up the sissy's rectum. Fucking her like a glove puppet.

"And this guy was pushing his fist in and out, fucking you with it?" Barry continued excitedly, his cock throbbing in his pants.

"Yes, Sir!"

"And did you like that, slut?" Barry asked as his fingers rapidly fucked the slave's rectum, jabbing in an out up to his knuckles. "Your fucking arse is broken-in now, isn't it? It gapes open when touched. A real fuck hole!"

"Yes, Sir!" the sissy agreed, for although it was indeed painful Simonloved being used and humiliated, particularly by young Master Barry fucking with his fingers.

"Well, I'll fist fuck you from now on, fucking slut!" Barry declared, rubbing his cock through the crotch of his trousers as he frigged the slut's rectum, feeling the wetness of pre-cum dribbling in his pants.

"Mr Simms said you danced for them, Simone," Mr Berne interjected, "and they all appreciated the beauty of it. Mr Simms told me it was wonderful."

"Thank you, Sir!"

"Mr Simms also wants to see you this morning, Simone!"

"Yes, Sir!"

"Perhaps you can go up when Barry takes the post trolly!"

"Yes, Sir!"

"And, Barry," Mr Berne continued, "don't do anything until she has seen Mr Simms. Is that clear?"

"Sure!" Barry was disappointed as he had intended to piss in the slave's mouth and to investigate her fuck-hole with his cock. "It can wait!"

Frankly, it would take all his will to resist fucking the slut's raging sore fuck hole. He wanted his cock shafting the slave's rectum. He was the slut's Master and 'she' would be reminded of it.

Fuck it! Barry decided he would fuck her no matter what Mr Berne had said, and what Mr Berne didn't see he wouldn't worry about.

As soon as they got in the elevator, sissy pulled her knickers down and bent forward with her arse sticking out as Barry pulled his stiff throbbing cock out of his pants and penetrated her hole. He was amazed at how easy it was. Sissy's anus was still mellifluously firm enough to give him pleasure. It felt so good!

Slap! Slap! Slap! Barry fucked the slave's rectum, his balls and hips banging rhythmically on Simone's buttocks as the lift made its slow ascent, and as they reached the top floor, his cock was pumping out its cum-juice deep in Sissy's rectum.

"Aaagh, aaagh, take that you slut...oh yes... you like this, don't you? You like my manhood inside you pumping my fuck juice!"

"Yes, Sir!"

"You're a pathetic little pervert who's got what's coming to you!"

"Yes, Sir!"

"A faggot!"

"Yes, Sir!"

"And now you are my faggot!" Barry loved abusing the slut, and he liked the word 'faggot' which he had read in a magazine referring to homosexuals. "Tell me what you are, slut!"

"I'm a faggot, Sir!"

"Fuck me! That was good, you faggot!" He remarked, zipping up his pants just as the doors opened. "It gets better every time!"

As they walked down the corridor to the Director's office, sissy could feel Barry's wet cum-juice deliciously oozing out of his 'faggot' hole and into his panties.

...

When they got to the Director's office, Barry suggested the sissy go in alone, and he would wait for her. The secretary told the sissy to go straight in. Mr Simms got up from his desk when she entered.

"Ah, Simone! Good! Good! Do come in. I thought it better we had a little chat!"

"Yes, Sir!"

"I hope you are not too distressed from your experience...umm...you really were terrific you know." Mr Simms continued a little awkwardly. "In fact...umm...you gave such pleasure to the elderly Judge that he wants to see you again."

"Yes, Sir! Thank you, Sir!"

"Good! Good!" Mr Simms continued smiling, "We will arrange something and let you know!"

"Yes, Sir!"

"You know you must never tell a soul about all this, and I am sure we can rely on your discretion."

"Yes, Sir!"

"Did you get the envelope?"

"Yes, Sir!"

"Good! Good! Well, there will be more if you give good service!" Mr Simms seemed reassured. "I appreciate it was ferocious, but...and I know this may seem a ridiculous question... but ..."

"Did I enjoy it? The sissy finished his question.

"I realise..."

"Yes, Sir!" Sissy interrupted again. "I...you see...yes, it was brutal..."

Sissy didn't know how to finish what he was trying to say.

"It is ok!" Mr Simms rescued him. "We will say no more about it!"

"I want to be a slave, Sir!" Sissy finally said it. "When that man was fisting me, I wanted to please him, Sir!"

"You danced divinely, slave," Mr Simms said reassuringly, "and we want you to dance for us again!"

***

The days passed relatively uneventfully. Work of the post room carried on, with Barry and the sissy doing the trolly rounds, with a regular deviation to the bathroom for the young Master to use his slave as a urinal. The sissy became adept at it, opening her mouth wide and gulping the Master's foul-tasting piss and then sucking his cock till he shot his fuck-juice. Then Barry would turn for the sissy to lick his anus clean.

"Yeh, you like that, slut, don't you?" Barry would ask, rhetorically. "Licking the shit from my anus?"

"Yes, Sir!" Sissy would obediently and humbly reply. For it was true, Sissy wanted to be humiliated in this way, and often sissy jerked himself off at night reliving the experience - tasting her Master's anus and his piss. Sissy's tongue 'knew' the feel of the young Master's hole. Simon knew how to please his cock. He would recognise Barry's cock by merely taking it in his mouth. He knew how it felt in his rectum. "She" was Barry's slave.

Barry was a vicious thug and a nobody, but the sissy adored serving him at every opportunity. Sissy loved the way Barry treated him, and the way he caressed her cock and balls in the post room or slapped his buttocks. He would lick 'her' Master's arse for hours if she could. Humiliating the sissy came naturally to Barry, as did the sissy's desire to serve her Master's needs.

The days and weeks passed and each week ended with the boys in the post room fucking her senseless, as they would do every Friday. It was their 'treat' at the end of a long week. The wounds from the slave market were healing and were barely visible. The remaining marks on her buttocks were now a delightful reminder of her ordeal. Sissy would relive the event in her mind with pleasure, and she longed for the promised return. She knew how brutal it would be, yet she wished to be auctioned again. Sold the highest bidder. It felt so good to be a chattel to be owned and sold on.

It took several weeks before the call came. Mr Berne informed sissy that a taxi would come for her and the same escort took her to the penthouse suite, leaving her waiting on the sofa in the lobby.

This time, the apartment was silent, with no loud shouting and cheering. There was no auction. There were neither screams nor the sounds of whips lashing bare flesh. Only the ticking of an imposing grandfather clock broke the silence, five minutes, ten, fifteen, twenty minutes passed before the escort returned and took Sissy to a room deep in the large penthouse.

It was a dungeon with walls painted black, and in the dim light, sissy saw iron manacles attached to the walls and a pulley contraption attached to the ceiling.

As the sissy surveyed the room, the escort attached an iron collar and chain around her neck and began removing her clothes.

"Quickly!" the escort urged, "You must get undressed. The Master will be here shortly!"

"Yes, Sir!" Sissy obeyed removing her clothing.

"You don't have to call me Sir!" the escort whispered, smiling. "I am not a master, sweetheart."

He called her sweetheart again, just as he had done previously in the taxi. For such a big, tough man, he seemed so considerate. Once Sissy was naked, the escort left her alone in the room.

Sissy took more time to look around the dungeon. A rack of whips and straps and a line of vicious-looking canes thrilled her. Two rods had been discarded in a bin and sissy could see the frayed edges with what looked like dried blood on them. They had been broken on some poor slave's buttocks; a poor wretched slave dragged into the dungeon and caned mercilessly merely for the pleasure of a blood-thirsty master.

Against one wall was a whipping block with straps to hold the victim in place. Various implements of torture were hanging on the wall. Sissy had no idea what form of torture they were for. Some were for piercing, others for clamping; all were designed to inflict enduring pain and discomfort, or to lock the slave in a degrading, contorted position.

Suddenly, the door opened, and the elderly man she had seen at the auction, 'the judge' entered the dungeon with a wretchedly beaten slave shuffling behind his Master with his ankles hobbled.

Sissy relished the slave's pitifully small cock, and she saw he had been castrated. His balls had been removed and the sac tightly closed. His manhood was gone. The thought of it made Sissy feel faint as a hot flush coursed through her body and she blushed deeply.

"Ah, the dancer!" The elderly Master proclaimed as a matter of fact on seeing Sissy, "I will get to you in a moment, slave!"

"Yes, Sir!" Sissy responded, obediently bowing her head deferentially.

The Master dragged the castrated slave into the room and ordered him to kneel. Sissy saw then that the slave had a tube inserted deep into his rectum, the purpose for which she could not comprehend, other than to keep his anus permanently stretched open, or simply to inflict discomfort. The slave was also emaciated and looked as if he had been held on meagre rations for a very long period. His head and body were shaved, and his buttocks had marks from regular, merciless beatings with cane and whip, the scars from deep lacerations inflicted repeatedly. His left thigh had been branded with a hot iron; a mark of ownership and slavery.

"This wretch is my personal slave," the elderly Master informed Sissy, delighted with her apparent excitement, "and I had him modified some time ago! I had him castrated, and his mouth is kept permanently stretched open, so I can piss in it. Tell me then, slut, does it turn you on seeing him like this?"

"Yes, Sir!" Sissy replied truthfully. For she was moved by the nature of the slave, with a mixture of fear and anticipation. She craved abuse. Would she give herself up like this wretched slave, to be used for the pleasure of others? Was this to be her destiny? From this, there would be no escape.

"Would you like to be castrated, slave?" The Master asked the sissy.

"I...do not know, Sir!" Sissy anxiously replied as fear struck her like lightning.

"Well, it matters not whether you do or you do not, slave. What matters is that it pleases your Master, isn't it?"

"Yes, Sir"

"Have you thought about it, slave?" The Master persisted, smirking, licking his lips in anticipation. "Having your balls removed?"

"Yes, Sir!" Sissy honestly replied because he had wanted to stop his progress to manhood. Signs of puberty had appaled him. He wished he had been born a girl. He wanted breasts and wished he had a cunt.

"Well, don't worry," the Master added reassuringly, "I am not going to castrate you! You're delightful as you are!"

"Look at my slave's little cock!" the Master continued with a mixture of derision and delight while fondling his slave's tiny penis, pulling the foreskin back to show its small glans. "What do you think? He was once quite virile, you know, and quite a cocky one. Now he has yielded to my will. He is here to serve. I took his manhood and gave his balls to a dog to eat. The hound swallowed the slave's manhood in seconds and then looked for more!

I am a Judge, you know, and I had the pleasure of sending this slave to prison and sentencing him to be flogged. I attended the flogging myself. It was one of the last judicial beatings in our prison service, and I paid the man wielding the rod to be particularly harsh. I wanted to hear him scream.

We thrashed him until he was a grovelling wretch begging for mercy! Then I arranged his parole, and he has served my needs since. My slave obeys without question, and if he offends me, then I beat him senseless.

Do you obey without question, Sissy?"

"Yes, Sir!"

"Let me show you the utility of my slave's mouth." The Master reached for a large rubber funnel shaped like a small urinal with a pipe that he attached to the end of the slave's mouthpiece. "There! Perfect. Now you will see what my slave is for."

The Master unzipped and pulled his trousers and underpants down and started pissing into his human urinal. Sissy could hear the Master's urine filling the funnel, and the rhythmic gulping as the slave swallowed quickly.

Sissy reflected on her own role as Master Barry's piss pot, and her cock danced and throbbed at the thought.

"There!" the Master declared as he finished and turned again to Sissy. "Now you, slave, kneel down and suck my cock clean!"

Sissy obeyed immediately kneeling and, taking the Judge's cock, she licked its head clean before running her tongue around the rim.

The Judge, sighing with pleasurable satisfaction, rocked Sissy's head on his cock as it slid between the slave's lips and into her throat. With a few more gasps and grunts, the Judge shot his cum into Sissy's mouth.

"Now you will come and dance for us, Sissy!" The Judge declared, pulling her up and leading her out of the dungeon.

Down the corridor, they entered the big room where the auction had been held. As at the auction, men were seated around the room, but there was no whipping bench.

"You will dance naked for us, Sissy, and you will please us as you do so."

As the music began, Sissy recognised the piece by Schubert. It was one he had practised at ballet school, and within moments the sissy was gracefully flying through the air with leaps and twirls. Round and round the room she flew, her jumps getting higher, her twirls more confident. She danced and danced, and her little cock and balls danced with her to the delight of the audience. On and on the music played.

"Higher! Higher!" the men demanded as Sissy danced, leaping as high as she could, urging her on until she was exhausted and gasping for breath.

"You must dance, slave!" The Judge demanded. "We haven't given you permission to stop."

Sissy summoned more energy and tried to dance on. Faltering, she stumbled and fell.

"Get up and dance, slave!" The Judge demanded, lashing Sissy's buttocks hard with a strap. "Get up! Get up!"

Sissy once more lifted herself up and falteringly danced, her legs trembling with exhaustion.

"If she won't dance, then she must suck my cock!" One of the men suggested.

"She will dance and suck all our cocks!" The Judge ruled as he pulled Sissy to her knees and towards his rampant cock. Sissy obediently took it into her mouth, still gasping for breath.

The Judge forced Sissy's head down on his cock, pushing it deep into her throat and holding it firmly, choking her as she gagged on it. Sissy was too exhausted to resist. She could feel his massive member deep in her gullet. Then he pulled it back only to thrust it back in deeper.

"Yes, slave, take my cock!" The Judge commanded as he repeatedly thrust his cock, fucking the sissy's throat. "Let it dance in your throat!"

All the time the music played, The Judge now thrusting his cock with the time and rhythm. Bang, bang, bang...bang, bang, bang...the music played. He held her face firmly as he swayed from side to side, dancing with her face on his cock, as the sissy gagged on it, pivoting her round on her knees as he rocked. During an adagio section, he held his cock firmly and swayed, slowly with the beat, but fucked her hard during an allegro banging her face down on his cock. The sissy's face and his cock danced a 'pas de deux' until eventually the Judge stopped moving and his cock pumped his fuck juice deep in her gullet.
"Aaaagh! Aaaaagh! Oh, yes!" The Judge grunted, "You dance well, Sissy, and your throat is a perfect cunt!"

Another of the men came now to take his turn as the music played on. Grabbing the sissy's head and ramming his cock in deep, just as the Judge pulled his spent member free. Bang, bang, bang...the dance continued, swaying and turning, fucking fast and then slow with the rhythm and grace of the music until in a final move his cock squirted its load.

Still, the music played as another, then another cock was thrust deep in Sissy's throat. Bang, bang, bang...cock after cock. Sissy danced for the Masters.
Log in or Sign up to continue reading!