Femdom Boss Pt. 06 - First Day

John awoke early. Having spent the last two weeks in intensive training to serve his Female Boss and Her employees. He had finally passed his final tests and was ready to take up his duties at the office. Miss Stacey had cared for him and been his principal instructor throughout his training ordeal, and he was so grateful to her. She had pushed him, and had been unyielding in demanding the best from him. She had punished him when necessary, but had been kind to him.

His Boss by contrast had simply demanded he perform, and perform well. Otherwise, She always looked at him as an object rather than a person, and he imagined that is exactly how She saw him. More as a piece of office equipment that She was testing out to see if it would be a good fit for the office.

As he bathed and got ready, he thought about that. His stomach was in knots as he was to be soon presented to the office. Each one of them would know exactly what he was to be used for, and he rather imagined the looks on their faces. Would they be lust-filled? Derisive? His stomach was knotted and he was barely able to eat his breakfast. Miss Stacey seemed to understand and didn't force the issue. Just let him stew in his own thoughts.

Soon, he was at his Boss's feet in Her car. Miss Stacey was driving them to the office. They were arriving about an hour after opening and his Boss had informed him that a special day was planned. He would be taken to the conference room and presented to the executive staff. They would have first dibs on him, and he would spend some time with each lady during the first couple of days. He would be fully moved into the apartment above his Boss's office, and would live there, alone. His food and amenities would be provided. He would need no clothing, as he would not be permitted to leave the apartment except to come visit one of the ladies in their office, or to report to the break room during certain times of the day when the office staff ladies would be permitted to use him.

In addition to that schedule, Ladies, both executive staff and office staff could sign up on a schedule sheet to come spend the night in his apartment to use him as they saw fit. His rooms would be equipped with everything the Ladies would need to enjoy themselves to the fullest with the new office toy.

There was a Queen sized bed in the one room, which he would not be allowed to sleep in, unless a Lady had signed up and invited him into the bed. Otherwise, he would sleep in the main room on a pallet much as he had slept in Miss Stacey's room on most of the nights of his training. There was a kitchen, and he had learned Miss Stacey would come by once a week and make sure it stayed stocked with everything that he would need. Water and his food kept in the lower cabinets. The refrigerator and higher cabinets would keep food and drink for the Ladies.

There was two bathrooms in the apartment. One with a luxurious clawfoot, old-fashioned tub, for the Ladies to enjoy, and all the amenities of a spa. And one, simple bathroom for him. A stand up, bare bones shower, that didn't even have hot water connected to it, a simply toilet with no seat, and a sink. His toothbrush, soap, and the appropriate paraphernalia for keeping himself well cleansed both inside and out were already there.

As he was shown these things by his Boss, he only trembled once when he saw the room that housed the toys. Whips, canes, a bench he could be bent over and bound. A large X adorned one wall. Another wall held an assortment of floggers and other sinister looking items hanging from hooks. A cabinet in one corner held clamps, cuffs, and other small play items. And there was a couple of shelves devoted to butt plugs and strap ons of varying shapes, sizes, colors and designs. He noted that not all of them were shaped like the traditional over-sized male penis. Some were shaped like dog penises, complete with the knot. Some like horse penises, those truly frightened him. There was a small section with a table that had stirrups, and his Boss clinically informed him that is where he could be fully examined to make sure he was healthy.

The last room held exercise equipment. He would be expected to spend two hours a day prior to work in there to maintain his shape. He was currently, thanks to Miss Stacey in the best shape of his life. It seemed his Boss intended him to stay that way.

She led him down the stairs and into the conference room, through a back entryway. He would not be presented to the office staff until the executive staff and finished their time with the new toy. The Ladies were seated around the large table and he was led in, and made to crawl up on the table, remaining on his hands and knees and crawl around so each Lady could fondle, grope, squeeze, pinch, and otherwise savor his humiliation.

He had studied brief bios of each Lady, and would be expected to fully learn their habits, what they most enjoyed, what turned them on. And it had been mentioned that at some point after a short period of time, he would be forced to endure a taste-testing session, where he would have to correctly identify each Woman of the executive staff by the taste of their Pussies.

He wasn't sure that that would be overly hard. He knew the difference between his Boss and Miss Stacey easily enough, and felt he could tell them apart even blindfolded. This was going to be much harder. Not least because he had no idea when the test would be. For all he knew, it could be that afternoon.

Miss Janice was the first to reach out and grab him by the chin. She pulled him close and forced his mouth open, peering inside, her thumb stroke his tongue, her fingers dug into his chin almost painfully. Nodding, She then released him.

Ms. Beth giggled as she fondled his caged cock, shaking his balls and grinning with delight when he gave a low moan of frustration. She gave his bottom a firm smack and whispered, "get used to it, toy."

Ms. Charlotte played with his nipples for a bit. She had tired eyes. Surprisingly she kissed him and then placed her lips to his ear and whispered, in a surprisingly sultry voice, "I can't wait to feel your tongue, toy, I am so wet just thinking about it."

Ms. Tameka, turned him around and spread his ass cheeks, Her fingers danced over his hole until with a firm push, one digit slipped fully up inside him. He lowered his head and shoulders to the table and moaned softly as She felt around inside him, finding his prostate and teasing it with her nail. She arched a brow and whispered, "Messy, toy," as she noted the drips from his caged cock." She made him lick up his mess, and smeared the rest over the head of his cock, making him jerk a bit in response. Her dark, chocolate covered fingers gripped his chin and pulled him close, and slipped the finger that had been in his ass and had smeared his drippings into his mouth and whispered, "I won the drawing to the be first in the office to plow your sweet boy cunt, its going to be a long, hard ride." Her eyes glinted as She spoke and he shivered remembering the shelves of various dildos he had seen.

Ms. Kamiko didn't crack a smile. Her fingers were nimble as they deftly examined every inch of him. Her voice was stern and unyielding when She spoke, "He should be thoroughly cleaned out before any intense anal play, Tameka, I will happily take care of that." Tameka nodded as did the other Ladies.

He heard his Boss chime and say to him, "Ms. Kamiko will keep track of your health and general well-being, toy. She is quite good with enemas, acupuncture, and various other treatments and such that you will undergo. She will also monitor your exercise most mornings, though most of us will also participate in that activity, when our schedules allow.

He gulped as his Boss led him off the table and to a spot on the floor where he knelt beside her. "OK, we have the sign up sheet, and it seems the first two weeks are already booked solid, even overnight stays! Very good. I want us to get our money's worth out of this toy. He is to help keep us relaxed and focused on our jobs. I really do feel that he will a great benefit to our company"

"Also, Ladies, remember, Monday afternoons and Friday afternoons are reserved for the office staff to sign up for 1 hour slot increments to visit toy in his apartment. After all, they work hard to keep us organized and deserve to have some fun as well. Agreed?" Murmurs of assent followed, and his boss led him out and up the stairs, followed by Ms. Kamiko, who it seemed was to examine him and prepare him for his first evening, which he learned would be with Ms. Tameka and her strap on.

Ms. Kamiko led him into the area with the weird table, and had him climb up and lay back on it. He was in a reclined position and She had him lift his legs into the stirrups. Binding them securely, She then spread them as far as She could. She strapped him down to the table and smiled at him. Her smile was quite sinister to his mind, and he was almost certain that this would not be a pleasant experience for him anyway. He was equally certain that Ms. Kamiko would enjoy Herself very much.

His Boss stood there watching the operation. Ms. Kamiko gathered the supplies She would need and placed a basin underneath where his bottom sat right on the tables edge. She then got a large enema bag and began filling it with hot water. Adding various other agents to the water. He had no clue what, but assumed things needed to cleanse him. She hung the bag and laid the tube over his thigh while She slipped on a pair of latex gloves and dipped Her fingers into a tub of some weird gel substance. She then began to smear that on his hole, opening him up and sliding her fingers in deep, twisting and turning them as She pumped them in and out.

He was quite thankful now for the plug he had worn so often, and the times Ms. Stacey or his Boss had seen fit to fuck him, because Her fingers were a breeze compared to those. Withdrawing Her fingers after a few moments, She removed the glove and dropped it in a bin, then slipped the tube from the enema bag up inside him. She then released the catch and his bowels were flooded with the water flow. It was very hot, and caused him to tremble, a low agonized moan escaping his lips. Ms. Kamiko made sure it was flowing nicely, then leaned down and examined his cock cage.

"Can you remove this please?" She asked. His Boss walked over taking out the key, and removed the cage. He couldn't remember the last time it had been removed. His cock didn't respond as he feared it might, but with the action of the heated water, he remained limp. Then the burning really started. Inside his ass, he felt it, not just the heated water, something more.

As he cried out, Ms. Kamiko smiled, "Ah, my special herbal cleansing remedy is having its effect. A few additions of certain herbs will make him nice and fresh, but I am afraid it does burn. She smiled as She leaned forward, Her fingers closing around his balls and grinned evilly at him, "I don't mind the burn, do you?"

He shuddered at the look She gave him and knew that She would make his cleansing times painful for Her enjoyment. He had accepted this. He knew it was coming. That just didn't make it easier to take. Ms. Kamiko then twisted his balls, bearing down on them, and hissed, "I do expect an answer, toy."

"N...no...Ms...Ms. Kamiko...t...toy...d...doesn't mind..." He managed to stammer out.

"Excellent, you should be getting nice and full now," She rubbed his tummy, and indeed there was a noticeable swell now as the foul, cleansing concoction filled him up. Ms. Kamiko set a timer for ten minutes. Then climbed up on the table and lifted Her skirt.

"Now, toy, while we wait for the enema to do its work. How about a little pleasure? For me anyway, She laughed and lowered her dark, hairy mass of pubes to his mouth, grasping a bar on the wall above him, She nestled Her pussy over his lips and he went to work immediately, tasting Her wetness, increased thanks to the activities She had thus far put him through.

She began grinding away on his tongue, his nose, his entire face really, savoring his low moans of agony against Her slit, savoring the feel of his practiced tongue working Her sensitive flower into a frothy, heated mess. He could hear Her excited moans as the pleasure built within Her. He did his best to fight through the pain he felt and try to memorized Her taste, the feel of Her against his tongue. She tasted very different from Miss Stacey and his Boss, a bit tangier, hardly any sweetness at all, spicy. He wondered if it was different because She was Asian. He wasn't sure, he had only experienced a few pussies up to this point, and they had all been white Women.

What he did know was that She was enthusiastic in Her use of his face, and just before the timer went off, She shuddered in an intense orgasm, grinding down hard on his tongue as Her cum gushed into his waiting mouth, swallowed down making him feel even more full than he already was.

Relaxing for a few moments, even after the time went off, Ms. Kamiko eventually climbed down and smiled at his glistening face. "Not bad, toy, not bad at all." She then pulled the tube out of him, and not being prepared, the liquid gushed from his ass, brown and murky, into the waiting basin.

While he emptied, Ms. Kamiko prepared a second enema to rinse him out. She would give him a total of four enemas that day. The third was to make sure he was clean, and when it gushed out clear, Ms. Kamiko gave him one more. This one more relaxing, calming, warm water mixed with olive oil and some other relaxing herbs.

He calmed down as She went back to playing with his still flaccid cock, which stirred to life under Her attentions. "When was the last time he was drained?" She asked.

His Boss replied, "He has not been. He was locked up and that's been that."

Nodding, Ms. Kamiko got some lube on her gloved hand and began stroking him. Firm, steady strokes, She very soon had him squirming in his bonds, wanting this denied pleasure. She kept squeezing the base though, denying him release, and soon stopped altogether, then emptied the basin beneath him down a drain, rinsing and flushing the waste. She wiped him up and then went back to his cock with a fresh glove, and kept him on edge for nearly an hour.

He was frantic for release, and finally, She began stroking him really hard, fast. He was moaning, writhing, Her hand felt so good. Then it happened, he was close, he was going to cum, it was building to a mind-blowing experience, when suddenly, just at the point he felt he could not stop it, Ms. Kamiko pulled Her hand away, and instead of a massive explosion, his cock sort of leaned over and began pulsing his cum over his belly. "So lovely to deny a toy the pleasure of an orgasm it doesn't deserve," Ms Kamiko said as She idly ran a finger in circles through the mess he had made on his tummy. "So lovely just to watch the cum sort of leak out of the head, rather than make those messy spurts of ropey filth normally associated with these things." Soon that finger was in his mouth, and he was sucking up his own cum. She continued until he had swallowed it all, then wiped him up with a wet wipe.

"He is ready for Ms Tameka now I think," Ms. Kamiko announced. She put his cage back in place over his now limp cock and released his bonds. He was led by Her and His Boss into the bedroom where he was told to wait for Ms. Tameka.

The two Women then left him there. He watched as they closed the door, and realized that there was a keypad there that read thumb prints. He was certain each Woman would be able to enter or exit the suite, but he would not unless for a specific reason.

So he settled down on his knees beside the bed to wait for Ms. Tameka, wondering which strap on She would select to use him with that evening. He was nervous, but this was something he was more accustomed to, and he hoped would be able to it.

He waited for nearly 2 hours, then She arrived. Miss Tameka was buxom, with the sort of milk chocolate complexion that was absolutely beautiful. Her eyes were dark pools of femininity. Her hair was shoulder length, and Her legs, long, toned, and in the heels She wore, made her seem much taller than She was.

She had stopped by the toy room first and had selected the dildo She wanted to use. 9" in length, black, with a mushroom head, and faux balls at the base. She was wearing it, causing Her skirt to tent out obscenely. She walked right up to him, and lifted the skirt, the tip of the dildo touching his lips, his eyes looking up at Her.

He opened his mouth and She pushed it in with a smirk. Her hands gripped his head and She thrust, choking him. He forced himself to relax as Miss Stacey had taught him to do, and She seemed satisfied when almost all the dildo disappeared down his throat. His eyes watered, and his vision blurred as he gazed up at Her.

She thrust a bit back and forth in and out, Her fingers tangling in his hair, Her nails digging into his scalp. He kept his hands out of the way, he wasn't allowed to touch without explicit permission, and on his first day, he wasn't going to dare break a rule. She enjoyed face fucking him for several long moments, before pulling out and smacking his face back and forth with the large, now very wet phallus.

"On the bed, bitch!" Her voice was deep, sultry, commanding, and he obeyed instantly, crawling up on the bed. She stepped closer, and smacked each cheek, the sudden loud slaps causing him to whimper. He lowered his head to the bed and reached his arms back to lay alongside him. She squirted some lube from the bedside table on his hole, and used the head of the dildo to massage it in. Stroking the cock to smear lube up and down the phallus. Then he felt it, the slight pressure as She pushed it against his hole. The thick head spreading his anal opening and then She thrust forward. He grunted as She grabbed his hips and pulled him back toward Her as She thrust forward. Hard and deep. She stopped when it was fully inserted and just savored his trembling body, his whimpers.

Taking a deep breath, She dug her nails into his hips and pulled back. Then began a thrusting, plundering fuck. She was ruthless with the dildo. She plundered his ass. Her toned hips smacked his ass with each thrust. His moans grew louder as She increased Her tempo. Deeper, harder, Thrust, pull back, thrust back harder. A steady, pounding rhythm into his hole.

She had amazing reserves of energy, and She kept up the steady, pounding rhythm for much longer than he imaged anyone could. He felt Her shudder against him several times in orgasmic bliss as She took him. Until finally She pushed him flat and lay atop him. She had removed Her blouse and bra and some point during the fucking of his bottom, and Her breasts mashed into his back. She tangled Her fingers again in his hair and lifted his head, he was so pale against the chocolate of Her skin, her hot breath in his ear made him shiver as she hissed, "Damn, you are a fine fuck, bitch. A fine fuck." She nibbled his ear a bit, then slowly raised up and withdrew the dildo from his bottom.

"Clean this up and then take care of me," She watched him as he removed the dildo and cleaned it off with his mouth as Miss Stacey had taught him. Laying it on the bedside table. She then lay down on the bed, and spread Her legs so he could nestle down between them. He then leaned down, still feeling a bit weak from the hard pounding he had received, he buried his face and tongue into Her pussy, parting those chocolate lips to reveal the pink creamy center. She was very wet from Her orgasms, and he spent several moments licking all around Her thighs, cleaning Her up before diving into Her sweet center, and lapping away, almost hungrily.

To him, Ms Tameka had the sweetest pussy he had experienced so far. Miss Stacey he still regarded as the best, but Ms Tameka, rivaled Hers equally in his mind. The taste, the texture. The contrast of his pale white flesh against Her darker chocolate was intoxicating to him.