The next morning the door opened and Greg blinked at the bright light that flooded in. The silhouette of Miss Emily standing over him reminded him of where he was and what he was doing. He wanted, needed, this woman to become his mistress. Her perfect form stood over him and as he took a position of subservience before her he felt an erection growing. She was so beautiful and so cruel.
"Use your toilet box before coming out," she snapped as she unlocked his chains. "Did you masturbate last night?"
Squatting over the toilet box, he swallowed loudly, stomach cramping from sudden nerves as he slowly decided he had to tell the truth. "Yes, Miss Emily. I couldn't help it."
"What a pathetic loser you are," Miss Emily didn't sound that upset, though her voice had an undercurrent of annoyance. "Absolutely no control over yourself. And you want to be my sub... well. We shall see. First, a little punishment for your disobedience."
Miss Emily took a leash and attached it to Greg's collar. He crawled after her as she pulled the leash, urging him to keep up with her. The collar bit into his neck and he gagged slightly, all the while watching Miss Emily's muscular legs walking before him. He wanted her to touch him with those legs, to touch him with anything. So far, his main rewards had been brief touches of her fingers as she manipulated his bindings. He yearned for her to rub against him, slide her hand over his most sensitive parts even if the purpose was to deliver pain.
They went down the hall and into the darkened torture room that had nearly broken his resolve earlier. There, Miss Siobhan was waiting. She was naked except for an elaborate harness, including headgear with a ballgag and an armbinder which was tied to a post that rose out of a hole in the concrete floor. Apparently, Miss Siobhan was still very much the submissive to Miss Emily.
What Greg noticed most as he was led to a stool in the middle of the room, was the huge strapon cock attached to Miss Siobhan. The straps were fastened very tightly around her thin hips and legs, and the 9 inch phallus stood out and bounced slightly as she wriggled a little to get a more comfortable position.
Greg was quickly bent over and secured to the stool, hands and feet. His legs were spread slightly, his ass presented to both the women. He still had a raging erection which pointed straight down between his legs now that he was bent over.
"Very well, Siobhan, you know how to do this. Don't spare any mercy. I want to hear him cry. I want to see tears."
Greg shuddered a moment as he waited. Miss Siobhan was still restrained and had to work herself over to a good position before pushing the false cock between his buttocks. He cringed at the hardness which pressed between his cheeks and sought his anus, anticipating the increasing pressure and painful penetration.
It happened suddenly. Once positioned properly, Miss Siobhan shoved forward with her hips with all the force she could muster and the dildo ripped open his anus and sank deep inside. The sudden tearing pain made Greg scream and writhe against his bonds, which did not give way. Miss Siobhan pulled back until the phallus was almost completely withdrawn and then shoved again, hard. Greg screamed again, howling in pain. He was sure he was bleeding and torn, and the full nine inches could be felt pressing deep inside him. There was no time to prepare, no lubrication, no relaxation, just vicious thrusting.
Miss Emily walked around to Greg's front and put her hand on his cheek tenderly. She felt the wetness of his tears and sighed with a deep smile of satisfaction as his head and body bounced with each thrust from the woman behind him. Her hands slowly stroked his head, his neck, his arms, and then his back, as if trying to feel his humiliation and pain. As Miss Siobhan continued her rape from behind, Miss Emily leaned over and kissed her mouth passionately. Miss Siobhan did not slow a moment though she kissed back as well as she could with the ball gag in her mouth.
Miss Emily moved her attentions back to Greg, and felt the hard false cock just where it entered his body. She touched his distended anus and then slid her hand down to his balls, and finally his still hard erection. She stroked gently, invoking a sob from Greg as his wildest dreams were realized; the combined pain of being raped by Miss Siobhan, with the touch and stimulation of Miss Emily. The pleasure / pain was quickly building to a climax when Miss Emily called a halt and demanded that Miss Siobhan withdraw. Greg was both relieved that the rape was over, but his cock strained for Miss Emily's hand, the pain itself would have been welcome if he had been allowed release.
Alcohol was produced to disinfect Greg's torn and wounded anus. The stinging shock made him writhe and cry out once again as Miss Emily poured a liberal amount of the liquid between his buttocks. Greg's ass felt like it was on fire, and he could not help but pull and buck against the ropes which held him firmly tied to the stool. When the alcohol dried and the pain subsided, he collapsed on the stool, weak from his struggles. Miss Emily untied him and pushed him down to the ground, where he lay motionless, breathing heavily as he recovered from this punishment.
"Up, you lazy dog!!" Miss Emily's clear voice cut through his foggy brain and jerked Greg back to reality. He stood, spreading his legs slightly apart to help sooth his stinging anus. Miss Siobhan, who had her armbinder removed by this time, attached a tight ball harness with leash and led him out of the dark room and into the living room.
"On your knees! Miss Emily wants the carpet cleaned, and you are to do it! Pick every scrap of dust, every fleck of foreign material up from this carpet until it is completely clean. If you don't do a thorough job, you will be punished. Get to it!" Miss Siobhan seemed delighted with Greg's predicament, and kicked him in the ass, pushing him onto his stomach with an "OOOppphhh".
Greg spent the entire afternoon combing through the carpet, inch by inch, square foot by square foot, making sure it was spotless. He had begun to forget he was naked, and didn't think about his job or life outside of Miss Emily's at all. Mostly, he just wanted to please her, and hoped that if he did well she would touch him. He wouldn't even mind being punished, if that is what was required to feel her touch and relish her attention.
The sun was down and the evening was well advanced when Greg finished acting as a human vacuum. His knees hurt and eyes were strained from crawling around the floor, but he felt he had done a good job. He sat up and saw Miss Siobhan staring at him with a look of disgust. He bowed his head and knelt before her.
"Mistress Emily, what shall we do with this pathetic creature tonight? You promised that I could please you tonight, can I cause him pain? I would delight in making him writhe and suffer for you, my mistress." Miss Siobhan was Miss Emily's confirmed submissive, and addressed her as Mistress, something that Greg deeply wished. He was prepared to do anything to be honored in this way.
"Siobhan, I have my own plans tonight." Miss Emily slid up behind the gorgeous woman and wrapped arms around her supple body. Miss Siobhan turned and reciprocated in the embrace, and before long Greg was observing the two women in a deep kiss, with Miss Emily's hands roaming the naked body of Miss Siobhan. His cock became hard almost immediately, straining and longing for a touch to relieve his pent up desire from seeing the two woman fondling and kissing in front of him.
When they finally broke their embrace, Miss Emily came over to Greg and pushed him down on the ground. She took a plastic zip lock and fastened his hands behind his back tightly. She then grabbed him and lifted him to his feet and guided him to her bedroom. He had never seen this sanctuary, and felt excited, nervous and aroused to be there.
Miss Emily led him to the foot of her bed where a strange post had been inserted and bolted to a hole in the floor. It was a very simple (though sturdy) device that puzzled Greg at first. Miss Emily positioned Greg so that the post was immediately in front of his naked legs. She adjusted its height until the top was positioned at his waist.
With a quick click, Greg's ankles were clamped in place at the bottom of the post with small metal cuffs. He was unable to move his legs at all. Next, Miss Emily grabbed Greg's scrotum flesh, pulling hard on it until his testicles were distended painfully. She pulled his sack of balls up and placed them into a small, curved metal bar at the top of the post. A hinged top piece pivoted over on top of his distended flesh sack and clamped down hard, securing him in place with his scrotum and testicles pulled painfully up. He stood on his toes as well as he could to reduce the pressure and pain, but it still hurt and he moaned, crying quietly as the pain began to slowly increase and spread.
"Ah.... I do love malesong... " Miss Emily commented as Greg made quiet moans of pain in his new position. She then turned to Miss Siobhan and removed the few straps and harnesses that remained on that gorgeous body before pushing her down onto the bed playfully. Miss Emily fell on top of Miss Siobhan and the two kissed deeply, their bodies pressing against each other, arms and legs intertwining and hooking, always in motion. Miss Siobhan groped Miss Emily, hands sliding under her clothes and pulling them apart until slowly, Miss Emily's slim, muscular form was revealed.
Greg stood on his toes, watching has the dominatrix he was coming to desire more than anything in the world made out with a woman, just a few feet in front of him. He couldn't move more than an inch, fastened in the testicle pillory as he was. It hurt, his stretched balls throbbing with pain that was slowly spreading across his hips. The pain he felt seemed somehow a symbol of Miss Emily's desire and passion for her female submissive, used to taunt and cause him mental anguish.
Miss Siobhan was servicing Miss Emily with passion, her head buried deep between the domme's legs. She was making muffled moaning noises as she worked and followed Miss Emily's bucking hips. Miss Emily was making her own, somewhat louder moans of pleasure that were building. Greg watched and yearned to be part of the sensual play before him, his cock hard and eager, but his balls remained clamped in the pillory and all he could do is watch the two female bodies give each other pleasure.
The lesbian love making went on for almost two hours, using every position possible. Greg watched as their hips ground against each other, faces were smothered underneath soft female breasts and pussies, hands and fingers explored orifices just before him. Miss Emily climaxed at least three times, and Miss Siobhan twice. Through all of this, Greg was made to simply watch, and suffer as his balls stretched and his penis ached with desire. Tears dried on his face and his legs felt like they were ready to give out from attempting to lift himself on his toes to relieve the pressure on his testicles.
When the two women had finally reached their final climax and fell asleep in each others arms, Greg remained standing at the foot of their bed, watching them snuggle and sleep. He had almost come to accept the pain in his groin, but his legs were giving out and he began to panic. What would happen if he could no longer stand? He might slide, or fall down with his scrotum still locked in this infernal device. The result would not be pretty. He imagined the damage that could occur were he to suddenly find himself hanging with his full weight from his pinioned scrotum.
He waited. He knew he could not wake or interrupt the sleeping women without being punished. He desperately wanted to meet Miss Emily's expectations and gain her approval, but he was losing control. He needed to pee as well. He began sweating from pain and exertion, his skin slick with moisture.
Finally, Miss Siobhan stirred, and Greg took the opportunity to speak.
"Miss? Miss Siobhan? May I be released? I need to pee, and I don't want to have an accident and soil Miss Emily's bed or carpet. Please, Miss?"
Miss Siobhan looked at him with a sleepily annoyed look. She hated him, he could tell. If it was up to her, she would probably let him fall and be suspended by his genitals, and then laugh at his agony. But, she was also Miss Emily's submissive and had to look out for her mistresses interests.
"Mistress Emily? The male filth is speaking. Shall I take care of it?" Miss Siobhan asked in a low tone.
Miss Emily rolled over and looked at Greg. "You foul, disgusting piece of crap. What do you mean interrupting our sleep?"
Greg was crying again, the pain had torn him down to the point he was going to beg. "Please, Miss Emily. The pain is terrible, and I don't think I can stand much longer. If I slip and fall, unable to hold myself up... I may lose bladder control and soil your bedroom."
Miss Emily sighed deeply, and rolled over to the edge of the bed. Standing, Greg could see her full length naked body, impressive in every way. His erection continued to be as hard as a rock. She walked over to him and unlocked the clamp that held his testicles stretched up high. Greg almost collapsed, weary from standing for so long, but his ankles were still secured to the bottom of the pillory. Miss Emily left the room for a moment and then returned with a bucket, which she placed beneath him.
"There. Use it or lose it. You know, you go home tomorrow, and I have not made up my mind about you. I like the way you suffer, but you are just such a fucking wimp." She shook her head in disgust and disappointment that made Greg wince as he squatted and let his urine flow into the bucket.
When he was done, Miss Emily had Miss Siobhan remove the bucket and then she unlocked his ankle restraints. Her touch sent a thrill through his body, and the presence of her naked body so close to his was almost enough to make him climax, such was his desire for her. She attached the leash to his collar and led him from the room and placed him back in his closet, in the dark, his collar chained to the floor with about a foot of chain that prevented much movement.
That night he masturbated repeatedly, thinking of the two women, especially Miss Emily, as they made love. He squeezed his balls to create the same pain he experienced as he had watched them. His sperm spurted onto his stomach and the floor as he dreamed of Miss Emily's touch. He knew he would be unable to hide his activity from Miss Emily tomorrow, but he couldn't help it. His cock had become raw from rubbing and his semen no longer flowed when his final dry orgasm was painfully done and he fell asleep.
The next morning he was awakened by a hard kick with a boot. He yelped and scrambled to the side, jerked to a halt by the short chain that held is neck a foot away from the floor. Looking up he saw Miss Emily standing over him, wearing black jeans, a tight knit gray shirt and heavy boots. The look on her face was unmistakable disgust as she saw his limp, raw penis and the dried semen spread all over his body and the floor.
Without a word, she unchained him and dragged him into the torture room, where she tied his wrists together and then pulled them up on a pulley until he was suspended above the floor. He swung there, hanging from his arms, as she walked in front of him, lifted his reddened cock and then dropped it in disgust. Obtaining a whip that hung from a nail on the wall she began to flog him without any delay.
Each stroke was like a knife slicing into his body. He screamed and wriggled as he hung from the pulley but he was totally exposed to her vicious punishment. Stroke after stroke cut across his body, his back, his front, hips, and even legs. He jerked, screamed, begged, pleaded and apologized. There was no response or letup in the punishment.
When it finally stopped Greg hung with his head down sobbing with pain and humiliation. Miss Emily looked satisfied and left the room for a while. Greg wondered how long she might leave him there and he felt blood trickling down a few places of his back and chest from there the whip had torn his flesh.
She returned after a few minutes and stood before him. Wiping alcohol on his wounds once again made Greg scream, jerking uncontrollably as the dominatrix treated his damaged flesh in the most painful manner. When she was done she stepped in front of Greg and lifted his limp head to face her.
"Do you still wish to be my slave?"
Greg gathered all his willpower and answered. "Yes, please, Miss."
She nodded. "You are not ready. You have promise but not control. I will take you again next weekend, but only if you observe my wishes during this next week."
"Yes, Miss. I shall do as you say."
Miss Emily took out a strong but clear plastic device. She took his limp cock in hand and slid it into the device, clicked it in place and then added another device to it which clicked in place tightly around the base of his scrotum. The final click was a tiny padlock which locked the device in place. The key went around Miss Emily's neck on a chain, hanging between two perfect breasts.
"I have placed you in a chastity device. It will not allow you to have an erection, and covers your penis so that you can not stimulate yourself. You shall wear this for the coming week. In fact, you will wear it until I decide to remove it. Is that clear?"
Greg nodded his head.
"Very well, when I let you down you will go to the front door and put on your clothes. You will leave and resume your normal life. Return here at 6 PM next Friday. Remove all your clothes before you ring the doorbell for admittance. Is this clear?"
Greg nodded his head, "Yes, Miss."
"Very well. During the next week you are not permitted to touch any woman in any way. Any command that any woman gives you is to be obeyed completely and without question. Is this clear?"
Greg nodded his head slowly, wondering what that might lead to.
Miss Emily slapped him, hard. "Answer me!"
"Yes, Miss Emily. I understand and will obey!"
Miss Emily slowly lowered his body and unfastened all his restraints. When he was free, he mumbled "Thank you Miss Emily," and looked at her beautiful face and form before he walked to the front door, found his folded clothes and put them on is sore body, and then left the house. He felt elated that he was to be able to return, frustrated that he was in chastity, and afraid of what the week might bring.
All in all, he had made progress in becoming the official submissive to the most beautiful dominatrix he had ever seen, but he knew he had work to do.