Femdom Boss Pt. 04 - Reality Check

After his training truly began, he was worked hard, daily. He learned proper protocols for how to kneel, how to present himself for inspection, and other very strict protocols. The second day of training also taught him a valuable lesson in just what failure would mean. Sure, he had been punished the day before for failing to hold the plug in during his run, but that had been fairly light, and while it hurt, he felt he could handle it.

The next day, after being run, and practicing positions all day long with no breaks, even though Miss Stacey would sit or lean and just watch him, occasionally using the long rod she held to correct his positions, she was relaxed. By the evening though, he was exhausted, his entire body ached when he was brought in to his Boss and She then began barking orders to test him on what he had learned that day.

His exhausted mind got confused several times throughout the test and each time his boss used a cane to "correct" him, rather harshly, until he was sobbing. Finally she announced that he had failed the test, and would be punished accordingly. Miss Stacey was called in and told the results. She nodded and grabbed his collar, leading him off when his Boss dismissed them.

Taking him down to her room, she smacked his face hard. His head jerked to the side and he teared up again as she hissed at him, "Are you simply stupid, toy? Are you? You fail the FIRST tests? Remember, this punishment is your fault for being a fuckup." She then drug him over to her dresser and shoved him up against it, noting the stripes from his Bosses cane, she selected a hard wooden hairbrush, then grabbed him and pulled him to her bed, bending him over her knee.

Then the steady smack of the brush against his upturned bottom had him sobbing in no time. His legs jerked with each hard smack, but with one of his arms pinned by Miss Stacey behind his back, he wasn't going anywhere, and She just continued to rain harsh blows down on his defenseless bottom until it burned a bright red. The pain flooded through him. Soon it ended and she shoved him off her lap.

"Kneel, toy," he heard the disappointment in her voice and it shamed him, so he looked down, not wanting to face that look on her face. Her fingers gripped his chin, not harshly, and she raised his face to meet hers. There was disappointment there, but also sympathy, which confused him even more.

"I know it was hard today, exhausting, but we will practice and practice until you get it right. That is what you are here for, to learn. Fuck ups like today will not be tolerated at the office when you are serving the Ladies there. Best that you fuck up here, because trust me, the punishments you will face for such failures there..." She trailed off and shook her head, "Best not to think about those." He trembled at her words.

"Now, I expect tomorrow you will do much better. We will get you into shape. Exhaustion will happen, but it is NO excuse not to perform as expected. A toy does not get exhausted. Believe me, those Ladies you will be serving, will not give a damn about how tired you are when they want to be pleasured. They are very selfish, very demanding, and very cruel. The spanking I just gave you hurt, I know it did, but trust me, they won't use a hair brush, like the Boss, they will use a cane, or a whip. Trust me, it will hurt far, far worse. Best to learn now, even make your mistakes now, because later, you do NOT want to fuck up."

She leaned down then, her eyes boring into his, "Do you understand, toy?" He gulped and nodded, earning him another slap and a hissed, "Answer me, bitch!"

"Y..Yes Miss Stacey," he stammered out, his cheek once again stinging with pain and shame.

"Good, now, since this is even more important, you are going to practice again what we practiced the last couple of nights. You are going to give me an orgasm. For two nights now, I have guided and instructed you, tonight, I want you to think about those practice sessions, what we did, what I had you do, and try to see if you can make me cum without my help." She lay back then, and slipped her shorts and panties off, tossing them aside and lay back, spreading her long, toned legs.

Her pussy was glistening, wet. He could smell her arousal and wondered what had turned her on so much, then with a soft voice, he asked softly, "Miss Stacey?"

She raised up and looked at him, "What?"

She sounded impatient so he quickly asked, "Did...did, um...spanking me, did that turn you on?"

She blinked, not really expecting his question and reached down rubbing her slit idly as she considered him. Feeling her wetness she smiled and then sat back up and raised her fingers to his lips, smearing her wetness across them and over his upper lip and whispered simply, "Yes, it did."

She then grabbed him by his hair, leaned back and commanded, "Now, please me toy. If I am not coming within the next 10 minutes, we will revisit that hair brush."

He gasped as his head was mashed against her, but she released his hair and he began. Remembering the guidance she had given him the past two nights, he didn't go straight for the clit, or even the opening, instead, moving to the side, he kissed, and lightly licked the outer lips. With a few moments, he felt her hips moving, and heard a low moan come from his sexy trainer.

Encouraged by this, he slipped downward and stiffing his tongue he circled the entrance to her pussy, without pushing inside, then began to lick straight up her slit, parting the delicate folds, stopping just below her clit, and circling it without touching it, then sliding back down those delicious folds. Delicious, yes, she was delicious. He found himself really enjoying her tangy taste, and as her hips began grinding with his tongue, he was encouraged and was soon lapping eagerly away at her dripping slit, then as her moans deepened, he finally arrived at her clit.

He captured it in his lips, hard and throbbing, his tongue lightly flicked it as he suckled it gently, gradually increasing the pressure until his tongue was lashing that sensitive little nub and her fingers suddenly tangled in his hair and as she pulled him into her, and begin to grind her hips hard against his face, he simply stiffened his tongue and allowed her to use him.

Within moments, her body trembled and she let out a wail, her back arching, and his face was flooded with her excitement. She continued her harsh grinding of his face, demanding more, and he licked and kissed and slurped as she moved him down and his tongue pushed deep into her, his tongue coated now in her essence, his mouth flooding with her cum. She ground on his tongue and he did his best to stretch it and force it deeper into her, and she humped against him harshly until with an even louder cry, and her thighs tightening around his head almost painfully, she shuddered in climax yet again.

Soon she calmed down, and relaxed her thighs. He was sweaty, her juices coated his face and as she raised up, she kissed him hard, passionately, and whispered breathlessly against his lips, "At least you learned something, toy..."

After that, she tousled his hair and put him to bed on his pallet, then lay down and went to sleep. He lay there, exhausted, still aching from the cane and hair brush, and actually smiled softly. He had pleased her. He had caused her to feel good. He felt proud. He was now scared of punishment, terrified of failure, terrified of just what may lie ahead, but as he fell into an exhausted sleep, he was determined to learn from Miss Stacey, and he would try very hard not to fail another test.

The next morning, Miss Stacey got him up an hour earlier than normal, and made him practice positions once again, over and over, drilling him hard before showering him, feeding him, then leading him upstairs to get their instruction for the day's training from his Boss.

As they approached her, she looked up and Miss Stacey held up a finger and began barking orders. This time he performed the positions flawlessly, and his Boss clapped and smiled.

"Excellent, toy, much better!" She exclaimed and motioned him forward. He crawled and knelt before her and she tousled his hair. "I knew you'd do well, but it is still early, lots more to learn, dear toy. I do believe you will be successful in your new position, and I want you to believe that, too."

He nodded, proud of his small success, but then as he heard her instructions he felt a bit sick to his stomach. She spoke, "For today, I want you, and every girl in this household to use the toy for relieving themselves each time they need to urinate. By day's end, I want him very accustomed to the taste, smell, and even more importantly, how to swallow it without spilling a drop. Lots of water today, do you hear that girls? Spread the word." He heard a tittering coming behind the door to the kitchens, and noticed his Boss smile, "nosy little sluts aren't they."

"Yes, Ma'am," Miss Stacey sounded amused, but continued, "I will deal with them, Ma'am."

"I am sure you will, Stacey. As for you, toy. Do not let this morning's success go to your head. You will be expected to succeed in everything, and it only gets harder from here. Go now, and learn. I will see you for your test this evening."

Stacey dragged him off and when they were out of earshot he timidly asked her, "Miss Stacey, am...am I expected to drink...um...pee?"

She stopped and turned, looking down at him. He actually felt comforted by her height, like she could protect him somehow. "Yes, you will be. The Boss has a fetish for giving her toys golden showers, and making them drink it, plus when she has a particularly amazing orgasm she squirts, and well, that is mostly pee, anyway, and as you are expected to swallow everything when a woman cums, you will need to be used to that. Besides, from what I understand, every Lady in the office has that particular fetish, so best you learn it now under controlled conditions, rather than get punished for balking at it later with one of the Ladies."

He nodded and she led him on for his morning exercise. After running, working out, and showering, Miss Stacey gave him another practice session with his tongue while she downed a second full 32 ounces of water. She had now drunk 64 ounces and he wondered at her thirst.

She had chosen to sit on his face for this practice session and as she ground down on him, nearing her orgasm, she began to tremble, grabbing his hands, she held him tight, and pressed down on his open mouth, and then without warning, he was flooded with her warm piss. It flowed into his mouth filling it quickly, seeping out onto his cheeks as he choked and tried to turn his head. Her thighs held him firmly in place and she hissed, "Swallow it, swallow!"

He gulped, but more splashed out than went down. Miss Stacey stopped the flow and let him adjust, and he was able to get down that first mouthful, then she began again, filling his mouth. Expecting it this time, he managed to swallow most of that, but still some seeped out.

She stopped again two more times to let him swallow before finally finishing. He know understood why she had been drinking all the water. She had taken him by surprise, and now, after it was over, did the nausea set in, he had just drank piss from a woman. He felt woozy, and his stomach did somersaults momentarily. Miss Stacey noticed this and sat him up, rubbing his back and whispered in his ear, "Relax toy, calm yourself down, and think about it. It really wasn't that bad was it?"

He shook his head and took deep even breaths, forcing himself to relax and the nausea subsided, "Excellent!" Miss Stacey exclaimed, "Now, let's go see if any of the other girl's need to take a piss."

He groaned as she hauled him to his feet and off through the house. The girl's were all quite eager to "relieve" themselves into his "willing" mouth, and all that day, he felt like he had swallowed gallons of the bitter, salty, hot liquid. Frequently during their practicing of positions, Miss Stacey had to let him relieve himself as well. Usually outside, in a bush, where she would make him squat down to release.

Finally, at long last, he was cleaned up and taken to his Boss. Miss Stacey left him to his testing, and he was motioned forward. She ran him through his positions, a few times, and announced she was pleased with the results.

Then she demanded pleasure. Luckily for that, Miss Stacey had given him lots of practice that day, not only on her, but on several of the other girl's as well, and though is tongue was tired, he felt he knew what to do. Indeed within 10-12 minutes of his practiced tongue working on Her wet folds, his nose buried in her, memorizing Her scent, she was arching her back, grinding away at his face and gripping his hair tightly as she took her pleasure from him.

It was no "squirting" orgasm as Miss Stacey had described, but his Boss seemed satisfied. Then came the final part of the test. Miss Stacey had warned him, that if he spilled here, he would be punished. As the day had worn on, he had gotten better, but now he was tired, almost exhausted and after swallowing her cum, and all the other girls he had swallowed that day, he suddenly felt nauseated.

Forcing himself to relax as his boss laid him back and then lowered herself to his mouth, he opened and she pressed down to seal him under her piss hole. The flow began, and he began to swallow almost as soon his mouth was less than half full. She continued for several seconds that seemed an eternity to him as she fought to swallow and concentrated hard on not letting any of her bitter nectar to escape his lips.

When she sat back on his chest and looked down at him closely, lighting a cigarette in her post orgasmic bliss, his Boss nodded her head, and whispered, "Pass." Exhaling in down over his face, she rose and moved to her divan, seating herself and summoning a maid for a glass of wine, and Miss Stacey to gather her charge for the night.

As Miss Stacey led him down to her rooms, they stopped and took a shower together, she brushed his teeth for him and kissed him, telling her how proud she was of him. Reaching down, she fondled his caged cock a bit, and he suddenly noticed that after a couple days of wearing it, and as exhausted as he had been he had forgotten about it. Her touches and kiss brought it back full force and he groaned in agony as his cock tried to harden in its tight metal shell.

Smiling, Miss Stacey kissed his ear and whispered hotly, "Ah well, too soon I think for any of that nonsense, come, let's get dried off and then you can...practice some more then, I think I will let you sleep next to me tonight. Don't get used to it. But you did pass today, and while rewards are not something you will get often, if ever again, but considering how much pain you were just in trying to get hard...it may not be a reward getting to sleep naked next to me anyway." With a smirk, she led him off to bed.

Indeed, it was not a reward, he barely slept a wink all night trying his best not to disturb her as her sleek naked body cuddled him close, her smooth firm breasts held firmly against his face.

The next day would be hard.