Femdom Boss Pt. 02

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He is taken home to begin his training.
2.9k words
4.5
23.3k
12

Part 2 of the 6 part series

Updated 06/10/2023
Created 04/16/2021
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After stripping his clothes off, having agreed to be obedient, he stood perfectly still while she went to the door and opened it, announcing to the office, "Ladies? He's signed, come on in."

As he stood there, naked, face red with humiliation, every woman he had worked with for the past six months paraded into the office, touching him, fondling his most intimate parts, each one kissing him softly on the lips and telling him what fun they were going to have with him now.

He trembled with each one. The pretty brunette in accounting who was just a few years older than him to the older ladies. All ranging in ages from 25 to 50. Some even older than his own mother.

Finally, it was just him and his boss, and she walked up to him and kissed him softly and said, "Don't be afraid, boy. We aren't going to hurt you, much. We are going to use you hard. Now, for tonight, we will be going to my home where you will begin your training. Gather your clothes and put them in that bin over there, you won't be needing those."

"Um...do..do I need to get anything from my apartment?"

"Hmm? Oh, no, I will provide all you need from this moment on. Come, Monday my attorney will take care of your apartment and things. I will have them put into storage, since you will no longer be living there. I did mention that we will providing for your accommodations now that you are the office toy. Well, the office bitch is a more accurate title for your new position. We will get into all that once your training begins. For now, quickly, put those clothes in that bin, and come here."

He did as she instructed and once again stood before her. She placed a narrow, black leather collar around his neck. From the D-Ring on the front hung a small pendant with the company logo on it. She then attached a leash, grabbed her purse, taking out her keys and whispered in his ear hotly, "Come on, baby boy, time to get you home."

She led him quickly down the stairs and into the private parking garage. Other ladies leaving for the night waved to him and made lewd catcalls at him as he was led by them to the boss's car. He blushed even more at some of the comments they made, and wondered if this is what girl's meant when they talked about men catcalling them.

Her driver, a tall, buxom redhead grinned at him as they came up to the car and she opened the rear door. His boss climbed in, then tugged hard on the leash. The driver leaned in and said, "don't dawdle there, toy, she hates being kept waiting."

He climbed in shuddering at the woman's tone, but as he was bent over climbing in, he felt a very firm pinch right on his bottom, he yelped banging his head on the frame and fell head first into the floorboard at his boss's feet. She glanced down at him with a smirk and just said simply, "Good, you are already learning your place. Stay there." The door was closed and the driver climbed in and started the car.

His boss lit a long, brown cigarette and soon the car was filled with the aromatic smoke. She soon lifted her feet and placed them on his hips where they were curled up beneath her. She barely spoke to him during the car ride, and he was suddenly wondering just what he had gotten himself into. I mean, yes, all those beautiful women kissing him, touching him, he had been hard as a rock the whole time, yet other than just a quick touch, none of them had commented on his manhood. Most of them just touched and seemed almost amused. And now, in the close confines of the car, smelling her perfume, her smoke, it was all so overwhelming.

His hand strayed down and touched his hardened member. Only about 5" in length, not that he knew anything about cock sizes or how he compared, but no sooner had he touched his cock than a sharp smack on the back of his head jerked him out of his reverie.

"You will NEVER touch that useless little flap of flesh again, bitch, do I make myself clear!" Her voice was harsh, almost cruel, so very different from what he had heard up to this point and he cringed in fear and pain. "That lump of flesh is company property now, as is the rest of you, and you will NOT touch it again without permission. We will deal further with this matter at home. Place your hands behind your back for the remainder of the trip."

He put his hands behind his back and just laid there, suddenly terrified of what awaited him. She could feel him trembling beneath her feet and smiled. Yes, the boy would do nicely, she thought. He has the proper amount of fear, as he should, and soon, she would fully break him and mold him into a proper little sex toy for her and the other ladies.

Soon the car came to a stop and the driver opened the door. His boss climbed out of the car and he heard her speak to the driver for a moment, "put the car away then take the boy to the maids. Have him bathed, and properly groomed. He doesn't have much body hair, but I want him smooth as a baby's bottom."

"Yes, Ma'am," The driver replied closing the door and starting the car back up. It stopped shortly thereafter in a garage, and the door opened again, and the driver looked in on him, grabbing his leash and grinning, "Come on, you cute little bitch, things to do."

She laughed as he climbed out and grabbed his shoulders pulling her back against him causing him to finally realize just how tall she must be, well over six foot tall. He then felt her tongue flick out and lick his earlobe wetly and whispered, "How much fun She is going to have with you, and perhaps, allow me to have some fun with what's left." She laughed again as he blanched and then tugged the leash and walked off with a curt, "come on, bitch."

He stumbled following along after her. Almost jogging to keep up with her quick, long strides. They entered a servants door in the rear of the house and she led him down to a kitchen where two women stood waiting. She handed them the leash and said simply, "She wants him bathed and groomed."

"Yes, Miss." One of the girl's took his leash and he was led out of the kitchen and down a hall. These two girls were dressed as kitchen maids, much like you'd see in Downton Abbey.

He thought he heard another woman speaking, and if he heard correctly he was even more worried...what he thought he heard was, "She is going to eat that boy alive."

For the next hour or so he was scrubbed until his skin was pink, shaved and rubbed down with a sweet, smelling body lotion until he shined in the lights of the bathroom he was in. The two girls taking care of him were quite thorough in his bathing, even pushing a small bulb up his butt and squirting warm water in until it came out completely clean.

They even brushed his hair AND his teeth, when he tried to protest and take the toothbrush saying he could do that himself, they just smacked his hand away and told him to just be quiet and do as he was told.

Soon, he was ready and the red-haired driver appeared again, he would later learn her name was Stacy and she also managed the household for his boss. She nodded her satisfaction carefully inspecting every inch of him. He yelped like a stuck pig when she stuck a finger up his bum and yanked it back out, nodding her head in satisfaction.

She then led him out of that room, and up to another room, where two other girls waited. These two wearing skimpy French Maid outfits. They begin measuring every part of him. His height, his arm length, leg length, feet, his neck, his chest, his waist, hips. They even measured his cock and balls. Soon, they produced a simple frock, in a drab grey color and put it on him.

He was not given shoes, and the dress was snug on him, hugging him like a second skin, barely coming below his bottom. They styled his hair a bit, though that caused them to cluck disapprovingly at how unruly his hair was, Soon just leaving it be declaring it would likely get messed up anyway.

The tall redhead waiting at the door just laughed as she smoked a cigarette and waited for them to finish. When done, she took the leash once again, and pulled him right up close, finishing her cigarette and exhaling the smoke directly in his face as she reached down and crushed it out then looked into his eyes.

"Listen closely, bitch. You are now going to be presented to your new owner. She is not one for being patient with boys who do not obey instantly. It would serve you very well to remember that." As she said those last words her eyes drilled into his and she continued in a voice that made the color drain from his face, her nose practically touching his as she loomed over him, "Not that I mind when they fuck up, because then I get to punish them." The grin on her face as she said that last made his heart skip a beat in fear.

Without another word, she turned, yanking the leash and dragging him behind her and up a couple flights of stairs. They soon entered an elegant room, softly lit by a few lamps scattered about. Dominating the room was his boss. She stood by a fireplace flicking ash from her cigarette into the flames then turned to look him over. The driver unclipped the leash and gave him a slight push. He stumbled toward her and awkwardly bowed.

She just eyed him cooly, then said, "You will kneel at the door, touch your forehead to the floor and then crawl to me, dog. Go back, try again. This is how you will enter ANY room with a Lady present"

He blinked but somehow knew not to utter a word as he turned and walked back to the door, where the tall redhead waited, then turned and got down on his knees, and bent forward until his forehead touched the floor, then he crawled across the room to her.

"Now you may kiss my feet, bitch. Always show proper respect to those above you."

He planted a kiss on the toes of each of her black heels and then raised up on his knees to glance up at Her. She looked back at him.

"That will do for now. You will learn many protocols over the next couple of weeks. You will be tested on them frequently. Failure to pass these tests or to learn quickly will be dealt with. I do not train on a reward basis. I do not believe in rewarding a slave. I find it best to punish them. Negative reinforcement is so much more effective when training."

She then turned and walked over to a sofa and sat primly, her back straight, and motioned him over to her. He crawled over and knelt again in front of Her. "Now, for tonight, we won't do much, but I do want to test certain skills. So here is what is going to happen. I am going to lean back and raise my skirt. You will remove my panties and then provide me with oral sex."

She spoke almost clinically about what she expected. He had never "gone down" on a girl in his life. Heck before today, he had only ever kissed a couple of other girls ever. And most of those were his mother and grandmother. Then there he was staring into the dark muff nestled between her firm thighs as she spread them and curtly commanded, "Begin."

He tentatively pushed his head between her thighs, feeling the heat from her flesh warming his cheeks as he inhaled the scent of her. Nervously his tongue flicked out and licked along her slit. She tasted tangy, it wasn't an unpleasant taste, just new, different, and he pressed his tongue a bit deeper. His nose was filled with her scent, and his vision was only of her.

Her pubic hair tickled his face, and every now and sometimes he felt a little hair on his tongue choking it down, not really knowing what to do.

Soon he felt her hand on his head, gripping a handful of his hair and hissing, "useless bitch, useless." Then she began to grind on his face, commanding, "keep that tongue out, bitch, keep it stiff." Her tone frightened him and he did just as she said as she grind hard against his face. It actually became painful, but soon he noticed her breathing was changing, she was getting more excited.

Her legs came down over his shoulders, and he felt her heels dig into his back as she began to moan, "Yes, yes, that is better, much better...oh god yes, harder...harder..." His tongue was aching now, his face felt like it was on fire. Then suddenly he felt it, a sudden gushing, a loud wailing cry from his boss that scared him, was this what an orgasm was like? He had heard about them, but never really experienced on with a female. The times he jacked off were very different, he had always been very quiet.

She was abandoned, as she came, her cum gushing out onto his tongue, her thighs tightened hard around his head, crushing him, the heat was overwhelming. She stiffened up momentarily, then finally relaxed, breathing heavily.

He saw her wave her hand dismissively and soon he was being dragged off by the tall redhead. She led his trembling body to her room, and took him inside. Sitting down on the edge of the bed, she gripped his chin, then leaned down and began licking his slick face, licking his lips, forcing her tongue into his mouth. Her eyes were closed and she seemed lost for a few moments.

"Mmmmm...She does taste so very good doesn't she, bitch?"

Lighting a cigarette, exhaling into his face she looked at him almost warmly, and smiled softly, "I know tonight and this whole day has been strange for you. You are so new to all this, but you will adjust. Remember, listen and learn. Do everything she commands, you'll be fine. You are primarily going to be used as a sex toy, so honestly, it isn't going to be that bad. Most men would give their left nut to be in your position."

He blinked, and then softly spoke, one of the handful of sentences he had spoken since he was first called into the boss's office, "i...i am scared, i am not sure why i agreed to this..."

She laughed and ruffled his hair, then pulled him close and hugged him, stroking his back she said softly, "It's OK to be scared. You should be. Fear will make you alert and make you pay attention to the training. You will need to learn how to please women. I will help you as I can, but you have to perform for her, and she expects and demands perfection. Work hard, obey, you'll be fine. Now..." Her voice dropped an octave and got very breathy, "would you like a little more ...practice between a woman's thighs?"

He gulped and nodded. She smiled and stood stripping off her clothes. She was indeed very tall, with large round firm breasts, her body was toned, strong, and when he inhaled her scent as she pulled his head toward her pussy, she smelled of sweat and that distinct womanly odor he would come to know well. She was far more patient, and took her time, giving him instructions, guiding his head and telling him what to do.

It took longer, but soon she came just as his boss had before, the taste was different, but still not unpleasant, and he found he was coming to like it as he licked it up from her dripping slit.

She smiled down and ruffled his hair, then stood and led him over to a pallet on the floor. "This is where you will sleep while you are in training. I will look after you when you are not being instructed. Covering him up she leaned down and whispered, "You are not to leave this pallet for any reason once I place you here. I can chain you down if I need to, but I would prefer you just stay here on your own. You did fine today, and I will make sure you get lots of practice."

He was somehow comforted by her words and by the time she climbed into bed and turned out the light, he was drifting off and soon was lost in his dreams where the spread legs of females haunted his dreams all night long.

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AnonymousAnonymousover 1 year ago

Nice to see John will have some support :)

JohnHerr48JohnHerr48almost 3 years agoAuthor

Anon, I understand, so that would be a limit for you - understandable why. For me and others, it is quite erotic.

AnonymousAnonymousalmost 3 years ago
Smoking - disgusting

If anyone was to smoke in my presence and blow it into my face I would slap them for endangering my health. I can't stand the smell of tobacco smoke of any kind as it triggers massive nasal bleeds very rapidly - not a mere trickle either - that are very difficult to stop - life threatening.

TomSpeedyTomSpeedyabout 3 years ago

Wow, this second chapter is way more interesting than the first one. The whole house tour, and the explanations of his new life is intriguing. I’m a fan of how he is treated and especially his new services that he has to provide. However, I think his sleeping arrangements could be more intimate in the future. Anyway, great chapter and I can’t wait for the next one!

AnonymousAnonymousabout 3 years ago

Femdom Boss pt. 2

As the story continues to build, and this part ending with a session between Driver Stacy (whom I expected be a T-Girl) and the slave. With some extra cunnilingus tutoring from Stacy, the slave will do better next time he services Mistress. 4 stars

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