Mistress X 04: Orgasm Roulette

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Note to readers: This short story is not part of any series. The setting and characters are based on those from my “Laura’s Femdom” stories. My Mistress X stories stand on their own but are best read in order.

This story describes a female domination session between Mistress Alexis X and two male chastity slaves.


Mistress X was a very experienced dominatrix. Through the years she had trained countless male submissives and dozens of female submissives.

She was highly sought after due to her skill and uncanny understanding of the submissive mind. Sadism and masochism is, first and foremost, a mental game. Alexis spent as much time studying the submissive mind as methods of inflicting pain and humiliation.

Alexis was a sadist. Nothing aroused her more than inflicting physical pain and mental anguish on her willing slaves. Another of her favorite activities was humiliation.

She rarely spoke of favorite subs or activities but naturally she had both. Her favorite submissives were young, hard bodied men, for several reasons, some obvious and some not so obvious.

Of course it was exciting to torment handsome and muscular “twenty something” men. What she enjoyed most about them was their sex drive.

They were at their sexual peak. Their fundamental sexual need was the key to their servitude.

For these reasons she had two favorite male slaves. She kept them both locked in stainless steel chastity cages and they served her under chastity contract. She was their key holder and the only decision maker of if and when they were allowed to ejaculate. These two particular slaves had never met each other. They were both heterosexual and physically similar.

They had served her for five and six months respectively. They were both on a twice monthly orgasm schedule. She knew it was difficult for young, healthy men to go two weeks without orgasm and she enjoyed the control it gave her.

At the culmination of each session they were truly desperate for orgasm. They had no idea how far they could be pushed but Alexis knew. She was going to teach them about desperation.

Years prior Alexis had seen a movie involving prisoners of war. Their captors forced them to play Russian roulette. It was a terrifying game of life or death.

That was the impetus for her idea of orgasm roulette. Each slave’s goal would be to make the other slave shoot his load first. The price of ejaculating first? A humiliating act of servitude.

All Alexis needed was to find two horny subjects. She had a humiliating challenge in mind to confirm that these two young men were perfect candidates. Her idea was to play on their fears. If they behaved as she expected, they would be perfect for orgasm roulette.

John was first. He was in session early on Friday evening. His chastity cage had been removed and Alexis had been tormenting him for an hour. She had brought him to the edge of orgasm multiple times. He was on his knees and she was going to test him. She wanted to confirm he would be an ideal candidate for her humiliation game.

Alexis said, “Slave John, do you want to cum?”

Of course John responded, “Yes please Mistress X.”

She went to the storage cabinet and returned with a shiny black salad plate. She placed it on the floor between his knees. He looked at her with fear in his eyes. She said, “Slave John, have you ever tasted your semen?”

He said, “No Mistress X.”

She reached out and pointed his cock down at the plate and began slowly stroking it. He watched her hand as she stroked. She continued with her mind game and said, “Eventually I will make you eat your cum.”

She was stroking gently. Just enough to heighten his arousal but not bring him to orgasm. After a few minutes she paused and squeezed his erection and said, “Look at me.”

He looked in her eyes as she held him firmly by the penis. She said, “Do you want to taste your semen tonight?”

John shook his head and said, “No Mistress.”

That was the response she was expecting, and wanting. She resumed stroking. She moved her hand faster to get him to the edge of orgasm once again.

John felt his orgasm approaching and said, “Mistress may I cum?”

Alexis stopped stroking and said, “Not yet.”

Johns balls were aching. He was nearing his breaking point. His balls were aching and he needed his orgasm like a junkie needed his needle.

Alexis said, “Slave I want you to taste your cum tonight. Just a tiny taste from my fingertip.”

She reached down and used just her fingertip to stroke his cock. She stroked from the base slowly to the head and back to the base.

Alexis continued, “I’m not going to force you to taste your semen tonight. However, if you refuse I will make you play a game at your next session. If you lose that game you will eat your entire load. Now, with that knowledge, are you willing to taste it tonight?” She resumed stroking his erection.

John thought for a moment as his orgasm was approaching. He ran out of time and said, Tipobet “Mistress may I cum?”

Alexis said, “Yes you may.”

She grabbed his penis and pointed it at the plate as she stroked his cum onto it. When he was done squirting she lowered her finger to the plate. She dragged her finger across the plate forming an “X”. She lifted her cum covered fingertip up in front of his face.

She said, “Last chance slave. Suck my fingertip now or there’s a fifty-fifty chance I’ll be feeding you your entire load in two weeks.”

Slave John said nothing but he shook his head no. Alexis said, “Very well slave. Put your chastity cage back on.”

Later, on the same Friday night, it was slave Robert’s turn. She put him in the same situation and offered him the same choice. He refused to taste his semen as well.

It was exactly what Alexis was hoping for. She scheduled John and Robert’s next session together. They had no idea how creative and cruel Mistress X could be.

Two weeks later Pixie had special instructions. She was told to have John strip and prepare for his session in the dungeon changing room like normal. But Robert was to strip and prepare for his session in the interrogation changing room.

She was to give John a black leather hood to obscure his identity. Robert was to wear a red leather hood. She told them that for this session their names were to be slave black and slave red.

Alexis was wearing only a black silk bra and panties. She wore strappy black high heels. She had a silver anklet on each ankle. From each anklet there dangled a key. One marked with red tape and the other with black tape.

Alexis walked to the regular changing room door and opened it to find John kneeling on the X wearing only a black leather hood and his chastity cage.

She said, “Slave black, crawl to my throne.”

As he crawled Alexis closed the changing room door. When he reached the throne she said, “Kneel proper in front of the throne.”

When he was in position she walked to the other entrance door to the dungeon. She opened it and Robert was kneeling next to Pixie wearing only a red leather hood and his chastity cage.

Alexis said, “Slave red, crawl to my throne.”

As he crossed the threshold Alexis said, “Thank you Pixie.” She closed the door. Slave red crawled over and took his place next to slave black.

Alexis walked between her two obedient chastity slaves and stood in front of them, facing her throne. She bent over at the waist and said, “Kiss.”

Each slave leaned forward and kissed an ass cheek. After several kisses she said, “That’s it slaves. Kiss my perfect ass. I own both of you and you will do exactly as I say.”

She put her palms on the seat of her throne as she enjoyed her position of power. After a few minutes of obedient kissing she said, “Enough.” They stopped kissing and she turned to face them. She seated herself on her throne.

She smiled as she looked into their eyes. She sensed their fear and uncertainty as she spoke to both of them, “Welcome slaves. You have both been denied orgasm for two weeks. You have also both made the same choice. By refusing to taste your semen you have elected to play my humiliation game. I call it orgasm roulette.”

She reached out and cupped both men’s balls in her hands. Both men’s cocks swelled in their cruel cages.

She said, “As you know the safe word is mercy. However if you choose to use it, you forfeit your orgasm until your next session. Tonight I am raising the stakes. Tonight, not only will you forfeit your orgasm, you will receive ten lashes from my favorite cane.”

She wrapped her fingers around each man’s balls as she felt her own arousal growing. She truly enjoyed her control. She began to squeeze each man’s testicles and smiled as they winced in pain. She held their balls tight as she continued, “When you leave here tonight one of you will be a winner and the other will be a loser. The loser will have consumed a full load of cum. Further, he will be denied orgasm for a full month. The winner will get to choose one of two prizes.”

Mistress X released their balls and said, “It’s time to free those cocks.”

She raised her right foot to slave black. The red key was dangling from it. She said, “Slave black, remove the red key.”

Slave black’s hands were trembling as he removed the anklet. Once he had the key she said, “Take off slave red’s chastity cage.”

He hesitated. She leaned down and slapped his balls and said, “Do it!” He dropped the key as he doubled over and groaned.

Alexis sneered, “Take off his cage or he will watch me cane your ass.”

Slave black found the key. He retrieved it and put it in the lock. It popped open with a twist and he removed the lock. Slave red’s penis began growing the moment it was freed from its prison.

She said, “Now pull off the base ring.” Slave black grasped the ring and began to pull.

Slave red said, “Ow!” The ring was squeezing his balls.

Alexis cautioned, “Slave black be Tipobet Giriş gentle. You are next.”

Alexis was getting aroused as she watched with delight. Slave black had to manipulate slave red’s balls to get the ring off. Alexis was enjoying watching him play with his counterpart’s genitals. She knew these men were heterosexual and this was not exciting for them. She felt her pussy getting wet and, the best part was, she was just getting started.

Once slave red’s cage was off she put it together with the lock and key on the floor, under her throne.

She repeated the process and forced slave red to remove slave black’s chastity cage. She placed it together with its lock and key under her throne.

Alexis had a box next to her. She reached in the box and pulled out leather restraints. First was a wide leather collar. It had D rings on the front and sides. She slid to the front of her throne and spread her legs wide apart. She said, “Slave black. Place your nose here.” She was pointing to her silk covered pussy.

Slave black complied. As he enjoyed her female scent she buckled the collar around his neck. When she was done she said, “Kneel proper.” He moved back into his proper kneeling position. His penis was rock hard and bobbing up and down.

She said, “Slave red, your turn. Place your nose here.” She pulled an identical collar from the box and placed around his neck just as she had on slave black.

She remained seated as she continued, “Both of you stand.”

She picked up a thick leather belt and wrapped it around slave red’s waist and buckled it in front. She did the same for slave black. She was thoroughly enjoying the scene. She took the time to stroke each man’s erection to keep them at peak arousal.

As she gently stoked she began getting inside their heads. She said, “After this evening you will both be changed. As you pass other men on the street you will wonder.”

She looked up into slave black’s eyes and continued, “You will wonder, was that slave red? Did I share those intimate moments with him?”

She looked down at each man’s rock hard erection and smiled as she toyed with them. Then she looked into slave red’s eyes and said, “Slave red, the same will hold true for you. You may be in an important business meeting and look across the table. Could the man seated there be slave black? Is he the man with whom you shared this humiliating contest? Did he enjoy it? Worse, did you enjoy it?”

Holding both men’s cocks she commanded. “Face each other.”

They complied and she pulled them toward each other until their erections were side by. She began gently rubbing their cocks together. She felt her panties getting wet as she reveled in her command over these two hopelessly horny men.

She looked up at them and they were both staring at their cocks. She said quietly, “I know this feels good slaves. It’s okay if you enjoy it but do not cum. The one who cums today is the loser. Did you ever think you would enjoy rubbing another man’s penis with yours?”

She was not expecting an answer. She released their cocks and said, “Face me.”

She moved back to the restraints. She dropped two wrist restraints and two ankle restraints on the floor. She said, “Slave black, put these on slave red. Make sure they are tight.

When he was done she had slave red put four restraints on slave black.

She said, “Turn your backs to me and put your hands behind your backs.” After they both complied she used padlocks to attach their wrists to the D ring on the backs of their belts.

She continued, “Face me again and then get on your knees.”

They both struggled to their knees. She reached in the box and took out the most devious item yet. It was a spray can of hospital grade topical anesthetic.

She sprayed each man’s penis until they were wet with the numbing liquid. She put away the spray can. Both men groaned at the powerful anesthetic. Initially it felt cold then produced a burning sensation on their genitals.

She chuckled and said, “It burns doesn’t it slaves? Don’t worry, it won’t burn for long.”

She pulled off her heels and said “Slaves, worship my feet. I want to see which one of you is better.”

The foot worship had nothing to do with her orgasm roulette game. She was simply giving the topical anesthetic time to take full effect. She was amused as she watched each man lick and suck her toes. Their arms were behind their backs so they couldn’t hold themselves up. Their faces were on the floor. They were trying to outperform each other.

Alexis teased herself through her underwear. She toyed with her nipples through her bra. Then she slid a fingertip gently up and down her panties, toying with her labia. She felt her wetness on the crotch of her panties.

After fifteen minutes she said, “Enough! Kneel proper.” Both men stopped and struggled to their knees in front of her. They were both rock hard, despite the fact that their cocks were numb.

She pulled two new, un-lubricated condoms Tipobet Güncel Giriş out of the storage box. She opened them and rolled a condom on each of them.

Alexis stood up and said, “Slave red. Lay on the floor, on your side facing my throne, your feet to the right.

He struggled to the floor and got on his side and into position.

Alexis said, “Good. Now slave black. Lay on the floor, on your side facing red, your feet to the left. The men were instantly uncomfortable both physically and mentally. Each man’s face was only inches from the other’s numbed penis.”

She pulled two double sided clips from the box and stepped over the men. She reached down and fastened the front of each man’s collar to the other man’s belt. Now their mouths were almost touching each other’s erections.

She sat back on her throne and said, “Okay slaves it’s time for orgasm roulette. Your goal is to make your opponent shoot first. The loser eats the cum from his own condom.”

She waited but neither man moved. She realized they had no motivation to start. She stood up and walked over to the storage cabinet. She returned with her favorite cane. It was a long thin stainless steel rod. She said, “I’ll give you to the count of ten to start sucking or I’ll start whipping your asses right on the floor.”

She moved beside them and said, “One… two… three…”

Slave black moved forward, put his mouth on slave red’s penis and started sucking. She held the cold metal cane against slave red’s ass and continued counting, “four… five…”

Slave red moved forward and started sucking as well. Alexis smiled and said, “That’s it slaves. Suck those cocks.”

She put down the cane and sat back down on her throne to enjoy the game. The only sound was urgent slurping. Alexis slipped her hand inside the front of her panties. She spread her wetness on her clit as she admired her work. These young men were desperately horny. They were beginning to understand the power Alexis had over them. The idea of sucking cock had never entered their minds but here they were sucking feverishly.

Just as Alexis had planned the men’s numb cocks were going to need a lot of effort to reach orgasm. Soon Alexis was nearing orgasm herself. She slowed her hand and kept herself on the edge.

She taunted the men, “That’s it slaves. Keep slurping those cocks but don’t cum. If you shoot first I’m going to feed you your entire load.”

She stood up and began slowly walking around the two men as they struggled. Slave red tried to pull his cock away from slave black’s mouth. Every time he moved, slave black’s head moved with it. That was the beauty of binding their collars to each other’s belts.

A few minutes turned into ten. Their numb cocks and their heterosexuality were preventing orgasm. Another ten minutes ticked by. Finally slave red was getting restless and starting to moan. Alexis didn’t want her game to end too soon. She reached down near slave red’s penis. She put her hand on slave black’s nose and pinched it shut. In order to breath he had to stop sucking. He could only suck between gasps.

The break in slave black’s sucking allowed slave red to focus on sucking. Soon slave black was moaning. He was not far from orgasm. Alexis did the same favor for him. She pinched slave red’s nose. After a few minutes she let go. Both men were nearing orgasm and sucking feverishly.

A few minutes later slave red lost his focus. His pleasure was mounting. He stopped sucking slave black’s cock and turned his face to the ceiling. He whimpered, “No… stop I can’t… I’m going to.”

Slave black began to pump his face in and out. He was stroking slave red’s cock with his lips. Slave red cried out, “Please no I… oh god!”

His orgasm hit like a freight train. His hot cum began spurting into his condom. He had just a few seconds of incredible bliss. He was thinking of nothing but pleasure.

Moments later reality collapsed on him. He had lost. He knew the consequences.

Alexis was clapping her hands. She said, “Very impressive slave black. I’m not going to ask if that was the first cock you have sucked.”

She moved to the men and removed the clips that were holding them together. She freed slave black’s hands so he could help. She said, “Slave black. Stand up.”

Slave red was the loser. Alexis rolled him onto his back and said, “Slave black. Help me get him on the bondage bench.”

Alexis and slave black put slave red on the bondage bench on his back. Alexis attached his ankle restraints to the corners of the bench. She chained the sides of his collar to the sides of the bench. His arms were still bound behind his back and were pinned under him.

Slave red’s penis was deflating as Alexis pulled off the full condom. She was careful to not spill any cum.

She tied a knot in the middle of the condom. She laid the full condom across slave red’s forehead and said, “Don’t move. If you drop this I’ll paddle your balls.”

Alexis turned to slave black and said, “You survived orgasm roulette. I’ll let you choose your prize. Do you want to masturbate to orgasm or… do you want to eat my pussy for ten minutes?”

Slave black was quiet as he though about it. Alexis said, “You have ten seconds to decide or you get neither.”

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