Part 5 - Training comes to an end
After his sleepless night next to Miss Stacey, he was exhausted the next day. Miss Stacey had to run behind him during his morning routine and slash his ass with her crop each time he flagged. He somehow made it through, though he wasn't sure how. It was a testament to Miss Stacey's exhaustive training throughout that he was able to make it at all.
Following his breakfast and clean up, he was run through his paces for his Boss, positions, oral service, then She picked up a strap on. He had grown accustomed to wearing a plug over the past two weeks, but this would be something different, and he shuddered as he watched Her put on the fake phallus. It was about 7-8" in length, and moderately thick, it looked about the same as the plugs he was forced to wear.
Miss Stacey guided him over to a bench, and pushed him face down over it, adjusting him so his ass would be at just the right height. She then bound him securely to the bench. Soon he felt her slip the plug from his ass, then apply a cold gel that quickly warmed up as her fingers massaged it into his bottom. She stopped at three fingers working in and out of his tight hole, preparing him for the Boss, who walked around in front, grasping a fistful of his hair and forcing Her phallus into his mouth. She pushed until he gagged, then choked, withdrawing slightly, She just began a steady thrusting rhythm into his mouth, every three or four strokes would go a bit further in. She seemed quite determine to get the whole thing into his mouth.
Miss Stacey had had him practice this with bananas and he had somewhat become accustomed to it, but the harder dildo was different, and he choked more often than not. Forcing himself to relax, his Boss eventually battered at his defenses enough that soon she had the hole thing in him. He fought off a wave of nausea that hit him, and relax and heard Her announce her approval.
She then withdrew the dildo from his throat and walked around behind him. Miss Stacey had moved to the side, and added lube to the dildo for his Boss who then placed the tip at the entrance to his exposed and vulnerable hole.
As it slid inside him, propelled by the force of Her hips thrusting he heard Her comment to Miss Stacey, "See how easy it slides in? He is tight, but that training has been good, hardly any resistance."
He felt full, even more full than the plugs had made him feel once he got used to them. The dildo was longer, and he groaned from the stretching of parts of him that had yet to be touched. His Boss took that as encouragement and smacked his ass firmly, stating with glee, "What a little slut you've become, toy! So proud of Your progress."
With that, She began thrusting. Her fingers dug into his hips, her nails felt like tiny knives in his flesh as Her hips thrust, getting faster with each movement back and forth. Sawing in and out of his tight hole. Soon, all he could hear was the steady pounding of Her hips against his ass, the increased breathing as excitement rose in his Boss, and then he realized he could hear his own moans coming out of his mouth, louder and louder with each thrust.
His Boss would occasionally smack his ass hard on the inward thrust, pulling back to thrust back in even harder. Soon both his cheeks were reddened. He felt strange all over, his cock wasn't hurting in its confined cage, he wasn't trying to get hard, but he was feeling a sort of pleasure just the same. It confused him as the relentless pounding of his ass continued.
It took him by complete surprise when Miss Stacey stepped in front of him and lifted his head up. He saw then she was now wearing a similar dildo strapped to her waist. His mouth opened and before he could do much more than grab a quick breath, Miss Stacey buried it in his throat.
The two Women then begin to steady thrusting motion, one would thrust in, while the other pulled out, then reverse. Back and forth it went for him it seemed an eternity. He heard them speaking and moaning as their own pleasure increased. He thought he made out a buzzing noise whenever Miss Stacey would thrust into his throat fully, and even felt a weird buzzing sensation around his lips. Realizing that the strap ons must have something to increase the pleasure for his two tormenters.
As their pleasure increased, so to did the force of their thrusts. Until soon the two Women were battering his holes without mercy. He could barely catch a breath now, and his eyes were starting to blur, seeing spots. He couldn't get enough oxygen, and began to panic. He jerked as much as he could in his bonds, which only seemed to drive their passions to increased heights. Until finally, with a loud cry from each Woman they thrust in at the same time, shuddering with their own pleasure. It was at that moment that strange euphoria settled over him and caused his own body to shudder in a weird form of orgasmic pleasure he had never before experienced.
Once they finally slid their faux cocks out of him and he could breath he heard his Boss note, "My, the boy has leaked quite a bit out of his cage, it is simply streaming down the bench. Do have him clean that up Stacey."
"Of course, Mistress," he heard Miss Stacey reply and soon he was unbound. His Boss had taken a seat where She could watch as Miss Stacey guided him to his knees in front of the bench where he saw slick slimy trails of his own cum sliding slowly down the padding to drip to the floor. "Now, toy, clean every drop, from the floor, too."