by Audra Black
Greg’s cock had gone limp once the major pain began but it began perking up at the thought of a fake penis being jammed up his bruised butt hole.
Soon, Mistress Emmeline returned with a long flesh-colored dildo with two fake penis attachments. Greg wondered who Mistress Lita was going to stick the other one into?
“Thank you, Emmeline. Did you remember the lube?”
Mistress Emmeline handed the humongous dildo to Mistress Lita and pulled out a small bottle of lube from her apron. She opened the bottle without being asked and ordered Greg to turn around and bend over. He did as commanded and shivered when the cool gel touched his anus. Like a pro, she began rubbing the lube all over, around, and inside his asshole. It was painful because she wasn’t gently sticking one or two fingers in but ramming in three or four and rubbing the lube in as deeply as his butt hole allowed her to.
To try and take his mind off the pain of Mistress Emmeline jamming her hand into his ass, he turned to look at Mistress Lita and saw she was fastening the dildo belt around her slender hourglass waist. The belt fit snugly over her black leather skintight suit. She looked amazing with two long penises extending out from her, she wore them with so much dignity and haughty pride that they almost looked natural.
Just as the painful fingering was starting to feel almost pleasant, Mistress Emmeline stopped and looked expectantly at Mistress Lita. “We are almost ready, just expecting one more visitor.”
Greg almost broke his vow of silence before he heard the click of the front door and the sound of footsteps on the tile entryway floor. He tensed as he realized Graham must have come home. Fuck! Graham the conservative politician had just come home and he was going to find Greg standing there naked with a lubed up ass and a backside full of scars and bruises. What was worse was that he realized Mistress Lita must have known when he was coming home because she was all ready for him.
He could have been angry at being lied to, at being set up for humiliation. But the second penis made him think this Graham was likely being set up just as much as Greg and that maybe Mistress Lita knew what she was doing. It was her job to make him uncomfortable, challenge him, push his limits and cause him pain. And from the excited, amused, and expectant look on Mistress Emmeline’s face what was coming next was bound to be pleasurable for someone.
And somehow, Greg knew that no matter what happened next, if he relaxed and obeyed his mistresses every command, never doubting, never judging, just submitting, that in the end he wouldn’t regret a single solitary second of his upcoming training.
The End
Training the Sub and Transforming the Sissy
Audra Black
2 Male Subs, Submitting Together
Greg Krail winced as Mistress Lita slid her silicon penis into his asshole. She rammed it in as far as she could before pulling out and ramming back in even harder. She appeared to be trying to stretch him using as much pain as was humanly possible. She was succeeding marvelously. So consumed was Greg by the terrible fiery pain that he almost forgot about the man whose house they had broken into until Graham’s voice suddenly bellowed out loudly.
“What the hell! Who are you and how the fuck did you get in here?”
Greg’s wails stopped mid-protest as he looked up at the short, dark haired man in the three-piece business suit, who was glaring angrily down at the three intruders. Nude Greg, with the dildo stuck up his butt, glorious, elegant, red-haired Lita in her skin-tight black leather suit with two long penises sticking out from a circular hole which surrounded her vaginal area. And blond Emmeline, mistress-in-training, who wore a white maid’s outfit and tall devastating 3-inch-heeled black boots and waist high nylon stockings.
“You know who I am, Senator Gordon Graham,” Mistress Lita brazenly called to him.
“M... Mistress Lita?” He stammered, stepping further into the room so he could her better. “What are you doing here in my house?”
“I am here giving my newest pet and newest apprentice a training session,” she said calmly, as if that were a perfectly normal explanation.
Mistress Emmeline approached him with a smile and a wave. “Pleased to meet you, Senator. I’m Mistress Emmeline. Mistress Lita has told me so much about you.”
Graham’s face burned red as he spluttered, “but how did you get in? I have an alarm?”
“And I have the key and the code, remember?” Mistress Lita said while Mistress Emmeline removed a small key from inside her apron. She held it up over the senator’s head as he tried to grab for it.
“You gave it to me when you first decided to run for office,” Mistress Lita explained after the short, red-faced senator quit trying to steal the key back from Emmeline. “You came to me, I believe, to beg me to never reveal your secrets to anyone.”
“That was four years ago,” Graham said.
“I’m a patient mistress, but now I am here. We are here. Would you like to share a dildo session with your fellow pet, Greg?’
“No!” Graham sounded as horrified as Greg currently felt. Mistress Lita had continued thrusting in and out of him while she spoke and the further in she went the more painful it became.
“I gave up that sinful lifestyle ages ago. I promised my wife. I’m not the same man I was when you knew me,” Gordon Graham pleaded.
“I have seen video proof that says otherwise,” Mistress Emmeline giggled.
“My girlfriend, Amber shared the videos with me and I, of course shared them with Mistress Lita.”
“Would you like to me to share those movies with your wife?” Mistress Lita asked as she pounded Greg so hard he almost fell over.
“No,” Graham said again. “I don’t want you here. I don’t want any of you here, please leave now, and take your toys with you.” His voice was saying one thing, but the growing bulge in his pants was saying something different.
“But I put on this dildo, especially for you,” Mistress Lita said taking the unused length and placing it between her luscious cherry-red lips. She licked it at the tip, then removed it and ordered Greg to suck on it, too. He did so without delay though the idea of sucking another man’s dick was anathema to him.
While Graham watched this display with wide, wary eyes, he didn’t notice Mistress Emmeline sneaking up on him until she grabbed hold of his growing erection through his trousers and caressed it softly.
Graham’s back stiffened and he bit his lip hard enough to draw blood, to prevent himself from crying out in pleasure. Mistress Emmeline whispered in his ear, her hot breath warming his skin. “If you really want me to stop, Graham, say the password. It’s been a few years since you submitted to Mistress Lita, but I’m sure you remember it.”
Graham did remember it indeed. Their safe word had been Cantaloupe. His lips did their best to form the word, but then Mistress Emmeline began stroking his balls, poking and prodding and squeezing them. She was so forceful, her hands so magically adept. There was no pain yet, but he knew it was coming and he wanted it. Oh gawd, how he wanted it!
Graham’s wife was as vanilla as yogurt and sex with her was just as fulfilling. In bed she’d just lie there limply, expecting him to take control. But that’s not how he was wired. Graham didn’t desire to be the man in control, he craved a strong woman to take control of him. A woman like Mistress Lita and apparently like young, twenty-something Emmeline.
Fuck! Who was he kidding? Graham couldn’t send Mistress Lita and Mistress Emmeline away any more than he could throw away his throbbing cock. Mistress Emmeline not only had him by the balls, but Mistress Lita had him by someplace even more sensitive, his passions, his kinks, and his lust. He knew it, and she knew it, too. That’s why she’d come here. She knew he wouldn’t be able to send her away. His country manor house was her country manor house now, and it would be until she decided to leave.
“I don’t hear the safe word, Graham. Does that mean I have your permission to do this?” And Mistress Emmeline twisted his balls sharply until the pain made him so lightheaded that he droppe
d to his knees.
Mistress Emmeline released his balls as he fell and Mistress Lita called out sharply, “Crawl to me, worm. Crawl over here and suck my dick.”
Greg felt Graham’s shame and humiliation as he crawled over to his mistress. It made Greg nauseous to see another man prostrate himself the way that Greg had often done himself. It reminded him how taboo this entire situation was. How any normal man would think and feel if he were to witness these two men making fools of themselves because they weren’t man enough to subjugate and conquer.
As soon as Graham was in reach, Mistress Lita grabbed hold of his neck and pressed his face toward the long, silicon dildo that wasn’t currently throbbing inside Greg’s ass hole.
“Suck my cock, my willing worm,” she ordered him.
And Graham complied, his mouth opening and closing around her thick chunky cock. She forced his head back and pushed the dildo further back into his mouth until it hit the back of his throat. Graham began sucking and licking it as she ran her long nails through his hair, etching deep scratches into his scalp.
“Slut, toy, you’ve had enough anal play, get down there beside your new friend and suck the slimy dick that was just in your butt hole,” she ordered Greg, as she roughly pulled out of him for the final time, causing him to cry out in relief and pain. She whirled him around and pressed down on his head, like she was pressing the down button in the elevator and Greg quickly sank down to his knees.
“Open your mouth and taste yourself,” Mistress Lita ordered Greg.
He opened up and she slid that wet, slimy, lubed up and sweaty fake penis down his throat. Greg choked and wanted to throw up. The taste was vile, not to mention he was sucking on a penis next to another man who was also sucking penis. Although the senator was fortunate enough to still be clothed. Greg became uncomfortably aware of his own nakedness and mortified that all this degradation was apparently incredibly hot to his natural blood-engorged penis.
Graham’s cock was also quite aroused, Greg noticed. Noticing this filled him with disgust and shame and for the first time he regretted agreeing to submit to Mistress Lita. The pain and stuff was cool, this type of humiliation was not cool at all. He hadn’t signed up for anything like this. It also ticked Greg off that Graham didn’t even seem aware of him as he was too busy stroking Mistress Lita’s fake cock with his hands while he sucked her off. It was like he’d done it all many times before and had become an expert. His eyes were locked onto Mistress Lita’s face, the entire time.
“You see, Greg. Graham and I had many, many sessions over the years. I trained him well and he knows exactly how to please me. I wanted him here to be an example of what I want you to become. Say thank you, Mistress, for this opportunity.”
Those words were the very last ones Greg felt like uttering, however, she pulled out of him, giving him room to breathe and speak, and he was grateful for that opportunity and so he repeated the required words.
“You’re welcome, slut toy,” Mistress Lita said graciously. “Now, pay attention to what Graham is doing and do the same.” She tapped his lips with the dildo and reluctantly, Greg opened his mouth and allowed her to enter into him again. He wrapped his hands around the dildo that was still outside and tried to replicate Graham’s precise rubbing, stroking motions. He obviously couldn’t see what Graham was doing with his tongue, and Greg really didn’t want to see that, so he experimented, licking the long silicon penis all around in varying motions.
Greg hadn’t paid too much attention before, so pre-occupied he’d been with Graham’s arrival and then the pain of his first pegging, but Mistress Lita’s two-headed dildo was technically four heads that entered into her vagina through the circular hole in her shiny, black leather skin suit. As he got better at mouth fucking the dildo the better the pleasure for his mistress.
She ran her long fingernails down his back and scratched him whenever he especially pleased her. This felt a lot better. The pain he felt as the price for the pleasure he gave her, he soon threw himself into a rhythm of suck, suck, stroke, pull in and out which always followed a deep scratch of pain on his back. He forced himself to focus on the pattern and the feelings, keeping his own eyes locked onto his mistress as she’d throw her head back and moan ecstatically at being mouth-dildo-fucked by two. Once Greg fully focused on his mistress he actually forgot about the man beside him, which he realized later, must be the true lesson.
Before very long, Mistress Lita was shimmying and shuddering and exploding hot cum all over her two human toys. It was beautiful, Greg thought, and very messy.
“Look what a mess you two made of me,” Mistress Lita said, yanking the dildos out of their mouths and unstrapping the belt from around her waist.
“You two need to clean up after yourselves. One of you shall follow me into the bathroom to give me a tongue and water bath, while the other shall keep Mistress Emmeline amused. The poor dear has had nothing to do while you two pleasured me.”
Greg was already naked, so he felt he was the obvious choice to help Mistress Lita shower. But he knew better than to make this suggestion out loud. As her slave toy, Greg knew his job was to obey not to have ideas.
“Graham can’t help you in the shower with that fancy suit on him,” Mistress Emmeline said, “so I think you should leave him with me. I have some fun ideas of things we can do together.” She smiled wickedly.
Mistress Lita and Greg the Ponyman
“As you wish, Emmeline, it doesn’t matter to me,” Mistress Lita said. “However, that orgasm has made me a bit weak in the knees. I don’t think I can walk to the bathroom. Slut-Greg, prepare yourself to carry me on your back.”
Greg was startled, though he probably shouldn’t have been, since pony play was on the list of activities he had originally agreed to. Greg quickly rose up on his hands and knees and Mistress Lita rummaged around in the schooner ship trunk until she came back with a harness and reins. She pulled the harness over Greg’s head and helped him squeeze his arms through the straps. This appeared to be a special harness made for human ponies. Then she settled her weight onto his back, before pulling the reins tightly over his neck and almost strangling him.
“When I pull to the left, you go left, ponyman, and when I pull to the right, you go right. When I say giddy-up, you go straight. Whinny if you understand.”
It had been a long time since Greg had tried to mimic a horse and he had a tight strap pressing on his trachea, but he gave it his best shot.
“Pathetic, but I don’t suppose you could do any better,” Mistress Lita said. “All right now ponyman, we are headed to the elevator. Giddy-up.”
Greg crawled forward, trying not to go too fast or unevenly so that he wouldn’t toss his mistress off. Her weight was heavy on his back, but not too bad, he was mostly just nervous about the hell he’d pay if he tripped over his own hands and feet and tipped her off to the floor.
“Go faster,” Mistress Lita’s black booted heel connected solidly with his balls.
Greg whinnied in pain and crawled faster. Soon he reached the indoor elevator which the extremely rich senator had installed in his manor house. For the first time, Greg wondered what had happened to Graham’s servants? Surely, a man as wealthy as this would have a whole passel of servants running around. Perhaps Mistress Lita had given them all the weekend off? She had that kind of power, Greg reasoned. Mistress Lita could make anyone do anything. And not only could she make them, but she could make them want to do it. Greg greatly admired his mistress and was suddenly proud to be of service to her as her human pony.
Mistress Lita hit the up elevator button and Greg carefully carried her inside, once the door swooshed open. The elevator looked like any commercial elevator he had seen and was large enough for three pony men and their mistresses, he estimated. The trip up one floor was quick and soon Mistress Lita was choking him on the left side of his throat, so dutifully he turned to the left and entered the first door he saw which turned out to be the master suite.
It
was huge with a forest green 4-poster bed, and a comfy sitting area with a flat screen TV in one corner. There were two walk-in closets, and a whole wall of floor-length windows with a door in the center leading out to a long enclosed balcony. Mistress Lita choked him on the right a couple of times and he managed to find the large master bathroom and carry his mistress safely inside without blacking out, although his vision was growing spotty.
There was a large old-fashioned claw foot tub and an open stone tile shower. There were two counters with mirrors and sinks and closets and shelves full of luxury bathing supplies everywhere. Greg felt as if he’d crawled into the smelliest, girliest fragrance shop in the world.
“Carry me over to the shower, ponyman,” Mistress Lita instructed.
Greg dutifully carried his mistress as close to the shower as he could get without crawling inside.
“Good, ponyman. Sit now while I dismount.”
Greg crouched down as low as he could go without upsetting Mistress Lita, then she climbed off him and into the shower. “You are no longer a pony, you are just a toy. Undress me, toy,” she commanded him and Greg gratefully stood up on shaky legs and stepped into the shower, so he could begin undressing the beautiful goddess who towered over him by at least a foot.
First, he bent down to remove her black boots from off her feet. He set those carefully on a bench, which was conveniently placed next to the shower. Then he stood back up to unzip her leather suit. It was tight and he had to almost peel it off of her. He did so slowly and carefully and then once it was removed and folded neatly on the bench, he saw that she wasn’t wearing any underwear or a bra. Her large, beautiful breasts fell free and her nipples perked out cheerfully to greet him. Her vagina was perfectly shaved and molded and he had to busy himself with unrolling the thigh-high nylons from off her legs to prevent himself from reaching out to touch it without permission.