Femdom Boss Pt. 05 - Training Ends

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."

He could smell the smoke as both Women lit cigarettes in the afterglow of their passionate release. As his tongue worked to clean up the mess on the bench. He cringed at the taste, not enjoying it nearly as much as he enjoyed his Boss or Miss Stacey's taste. He was noticeably taking his time as he didn't relish the puddle on the floor. That is when he felt the sharp sting of the crop against his ass. He jumped with a cry of surprise and pain bumping his head on the padding and heard Miss Stacey, "Do be faster, toy, you made the mess, now get it cleaned up!"

He was soon lapping away quickly at the puddle on the floor as Miss Stacey continued to apply the crop to his ass to the delighted cries of his Boss from the sofa watching and it seemed rubbing Herself to another very pleasant climax watching Miss Stacey crop his ass while he humiliating licked up his own ejaculate.

Soon, it was over. His Boss announced Her pleasure at his progress and then stated that he would get one day of "rest" on Sunday, then he would be off to the Office where he would take up his official duties to the rest of the staff as well as to his Boss.

Miss Stacey led him off and got him cleaned up, and hugged him tightly whispering, "I'm going to miss you, toy. I've enjoyed working with you the last couple of weeks, but we knew this day was coming, and we have all day tomorrow to play together, we will make it special.

He slept like a baby on his pallet that night, he didn't dream and woke in the same position he had fallen asleep in a puddle of drool under him and Miss Stacey nudging him with her boot.

"Rise and shine you slutty little toy! I'm horny!" With that announcement, she nudged him onto his back and straddled his face, lowering her very wet pussy to his waiting mouth. His tongue began its work of pleasuring the demanding trainer that had been his near constant companion for two full weeks. She rotated her hips and ground hard against his tongue, lips and nose, using his entire face really to pleasure herself.

He snatched breaths when he could and kept his tongue constantly out, stiffening it whenever her oozing, juice-filled hole would pass over his tongue, and wiggling it and flicking it, whenever her hard clit would pass over. Soon, she grabbed his hair tightly, and jerked him up, her thighs clenching around his head as she shuddered, gasping in orgasmic delight, his mouth flooded with her cum. He gulped it down steadily, and then a slight adjustment and her morning piss flooded his mouth. He gulped that down as well.

She sat back on his chest and lit a cigarette and calmly smoked as she came down from the high of orgasm. He just gazed up at her and realized he would miss her terribly. She was safe. He understood her, understood what he needed to do to please Her. He was quite nervous about Monday. The other women at the office. He remembered each of them.

There was Ms Janice. She was the oldest Lady in the office. Even older than the Boss. Somewhere in her early 50's he figured, She was a stern woman who had rarely spoke to him in any tone but one of an authoritarian handing out orders.

Then there was Ms Beth, by contrast the youngest Woman in the office. Not much older than he was in her mid-twenties. Beth was bright and bubbly, and would sometimes when they were alone together pinch his bottom, and grin mischievously enjoying how red his face would turn.

Ms Charlotte was in her thirties. A single Mom who seemed to not like men very much. Another one he was slightly afraid of before beginning his new job, now he was afraid of most of them, but Miss Charlotte he was truly terrified of. He was worried just how She would take advantage of his new position.

Ms Tameka was the only Black Woman in the office. A bright, energetic worker, She was who His Boss was grooming to take over when She retired. In her last 20's Tameka was well-educated, very good at Her job, and had often eyed him in his early days in the office like She was sizing him up for a barbecue. She was another one, he wasn't quite afraid of Her, certainly not terrified, but She made him nervous.

Ms Kamiko was from Japan. She was the shortest of the Women in the office and was in Her 30's as well. She handled most of the Asian clients and markets, and of all the women, who were all beautiful in their own way, but Ms Kamiko was the one he was most enamored of. She was mysterious. He wasn't sure how to feel about how She would make use of him.

The rest of the staff was the office Ladies. Secretaries and support staff. He would serve them of course, but it had been made clear that his primary duty was to the executive Ladies.

Miss Stacey then flicked his forehead rather hard and hissed, "pay attention to me, toy! Don't get lax now!"

He winced and realized that as he was thinking about the next day and the ladies in the office, Miss Stacey had been speaking to him and he blushed and whispered, "Sorry Miss, I was thinking about tomorrow."

"Ah, well, that is to be expected, but daydreaming will not be tolerated by the Ladies at the office, so, you need to learn to focus."

He nodded and she got him to his feet. Then showered together, went on a long walk, not a run thankfully. Though Miss Stacey would still smack his ass periodically just to remind him she could. They stopped again at the same spot she had stopped that first day, and once again he found himself between her firm thighs, lapping away at her juicy pussy, performing all the little tricks he had learned that she loved and soon she was shuddering through several strong orgasms, clutching his head firmly between her thighs. Then releasing him and leaning back to light a cigarette and stroke his hair laying against her thigh.

"My, you have become quite...good at that, toy, I truly am going to miss your tongue." She relaxed and smoked her cigarette, idly flicking the ashes down over him.

They ate a late lunch, and took another walk in the evening. This time, she put him on his hands and knees, and using her fingers she massaged what she called his little man-g-spot. He was soon moaning and wiggling his ass at her, which made her smile and remark, "what he little slut he was becoming."

His balls soon oozed their creamy, drippy load out of his limp, locked up cock, then he started really listening to what Miss Stacey was saying as she massaged his little balls, "You must no longer think of this as a cock anymore, toy. It's not a cock. A cock is used for fucking, for procreation, and this will never be used for any of that. It will likely remain limp and locked up for quite sometime, if it is ever truly released. No, now you must think of this as just a useless little lump of flesh. Sure some like to call it a clit once you are locked up like this. But I find that wrong. A clit is something to be worshipped, something a Woman has that brings Her pleasure. On you it is wasted, as you received no pleasure from this, just an unsatisfying release. That is all you will likely ever receive, unless you are lucky enough to experience another anal orgasm like you did yesterday. Very surprised that happened actually on your first real fuck. But perhaps running with that plug every day increased your sensitivity."

As he sat and listened to Miss Stacey, hearing what she said, trying his best to process it, to internalize it. She had frequently mentioned how it would be best to forget he even had a cock, now she was telling him not to even think of it as a cock. Just as some useless lump he pissed out of. He supposed that made sense, suddenly realizing he would never know the pleasure of entering a woman.

On that count he was wrong. For after their talk, Miss Stacey took him to bed, and unlocked his cage. She skillfully manipulated his little useless lump of flesh until it stood out hard. Not thick, not long, but a good 4-5 inches. Then pushing him down to the bed, she rose up and poised herself over him.

"Now, toy. I am going to do this for you, and though you may enjoy it, it is not something I am doing to help you. For this will soon be torture. The Boss wanted this, so I am doing it. I wanted to let you go on never knowing what this would feel like. She wants you to know. So that for the rest of your time serving in the company's employ, you will know that you will never again experience this."

With those final words, she gripped the base of his hard cock and took him inside her.

His eyes widened and his back arched at the feel of her silky smoothness, wet and warm, enveloping his useless lump of flesh. She rode him steadily, and after his early milking, he took awhile, but soon he was moaning, and thrusting up to meet her. She was rubbing her clit furiously, a look of frustration on her beautiful face, and then her eyes widened as she felt him clench and thrust up his cum bursting forth into her.

Sighing she shook her head, and whispered, "And this is why little toys like you are locked up." She moved up and plastered her now very wet pussy over his face, clutching his hair and hissing, "please me, bitch!"

He recognized the taste of his own cum as it flowed mingled with Miss Stacey's distinctive taste. She rode and ground his head hard into the bed as she extracted several intense orgasms from his tongue.

Finally, she cleaned herself up, then him, then locked his cage back into place and climbed into bed. Cuddling him to her she whispered, "Try to forget that happened, you will be happier for it, toy. Though I doubt the Boss will let you forget it. Now get some sleep, big day tomorrow."

He lay there for a while, thinking about exactly what she had told him to forget and how he would never again feel that. It saddened him, but at the same time, he had seen the look of frustration in Miss Stacey's face, and knew that he would rather see the look of joy he saw whenever she used his tongue. So perhaps it wouldn't be so bad after all.

He drifted off to sleep then, dreams of what tomorrow would hold filling his mind.