Green Bush Erotica Collection Volume 16

Kassie’s Service

 

Elliot Silvestri

 

Chapter One

 

WALKING INTO JOSEPH’S house was the more difficult than she had imagined. Yes, she had found his ad on the adult dating website, met him in a public place, got all his important personal information, did some basic sleuthing on him, even found his Facebook page; Kassie had taken all the right precautions. She was feeling super-responsible and adult, even if she was only eighteen. While what they were planning was strange, it wasn’t illegal—strictly speaking—and she had never once gotten a creepy or weird vibe from her. She listened to her gut and not her lust. Everything seemed normal.

Except for the fact she was going to let a man nearly twice her age use her as a sexual plaything.

When he answered the door Joseph was dressed casually. It was early evening and he was home from work. She had told her parents she was going out for a job interview.

“With whom?” her mother demanded.

Kassie reluctantly handed over Joseph’s name and business card as instructed by him.

“What kind of business interviews someone outside of normal hours?” her mother demanded.

“It’s a personal assistant job,” Kassie told her. “He’s one of those business managers running around all day. He doesn’t have time to interview during the day. Geez, Mom, it’s only six o’clock. If I was going to work at a movie theater I’d be out until midnight every day.”

The logic wasn’t quite right but it passed muster.

“Hello, Kassie,” Joseph said as he ushered her inside. “Are you ready for your interview?”

She nodded and balled her hands into fists to stop her fingers from trembling. She was half-excited and half-nervous about what she was contemplating. “Yes,” she said clearly.

“Good. This is just an interview with no guarantee of employment as a personal assistant of mine. I have several demands that you might find too stressful or be unwilling to do. We’ve discussed them already. Are you ready to begin?”

Kassie nodded her head again and wished she hadn’t worn her hair back in a stupid ponytail. That only made her look younger and more immature. But was that what Joseph wanted? It was hard to tell. She dressed neatly for the interview, not too professional, not too outrageous, nothing too sexy. “Yes. Just a little nervous.”

“That’s good,” he told her. “That’s to be expected. This is a little scary; I understand. If you want to walk out at any time, just say the word eclipse and we’ll stop everything and you’ll leave. No hard feelings. No problems. If you change your mind, even after a minute of sitting in your car, just call me and we can continue when you’re ready.”

She laughed nervously. “Why are you doing this? Being so nice.”

His smile was lopsided. He had crow’s feet in the corners of his eyes and a touch of gray in his hair at the temples but was otherwise just another man. “Because this only works if you trust and respect me. I have special needs; I can’t force you to fulfill them. I want you to fulfill them because you have a burning desire to do so. Understand?”

“I think so.”

He nodded. “You’re young. You’re a bit confused still. It’s my job not to spoil you for others in your future, but I have desires that I can’t ignore either.”

“Right,” she agreed vaguely.

He gestured to her, leading her from the entrance hall, through the kitchen that appeared to be completely unused, and into a living room where the window shades were drawn. She doubted anyone would be peeping inside the house. They were in the middle of suburbia at the top of a fairly substantial rolling hill. Anyone spying on them would have to drive up a long and winding driveway. She followed him into the room. Joseph flopped himself into the large couch while she stood nervously in the middle of the room. He didn’t offer her a seat and she didn’t know what to do as he stared at her.

Her clothes weren’t revealing but they did show off her young and trim body. She wished her breasts were bigger; being flat-chested through high school hadn’t made her popular with the boys. She considered herself to have very plain looks, not notable at all beyond her platinum blond hair, but Joseph insisted she was a classic beauty. Mostly she tried to stay out of the sun because of too many sunburns when she was very little and ate a healthy diet.

“Sorry for staring, but you have an incredible striking look. Unique. I like that. I hate the conformity of too many women in our society. I like how you are proud of your appearance.”

Kassie wouldn’t go that far, but she wasn’t ashamed of her looks. She didn’t see a monster when she looked in the mirror.

“Let me ask you a few questions first. You need to answer honestly. Don’t try to guess the answer you think I want. Some you’ve already answered and I just want you to repeat them for me. Is that okay?”

“Yes.”

“Are you a virgin?” he asked. On the couch next to him was a clipboard. She hadn’t noticed it when she first walked in. Joseph had picked it up and was now making notes.

“No.” She blushed as the admission. He already knew this, so the reaction was stupid.

“How many boys—men—have you slept with?”

“Just two.”

“Both while you were in high school?”

“Yes.”

He scribbled a comment on the paper held to the clipboard.

“Have you had oral sex? Giving or receiving?”

“Both,” she answered with a bit of pride. The first orgasm she ever had that wasn’t at her own hand was with her first real boyfriend who loved to eat her pussy.

“Have you ever had anal sex?”

She shook her head. “No.”

“Have you ever had sex with a girl—a woman?”

This was a new question. “No,” she answered honestly

“Have you ever kissed another woman? I’m not talking about your grandmother or aunt. I mean a kiss from a woman you wanted to have sex with.”

“No,” she repeated. He made another note.

“Do you think you might be bisexual?”

This question was new as well. She opened her mouth to answer but no words came out at first. “I…I don’t know. I mean, I like boys. Girls are pretty and all, but I don’t think so.”

“What would you do if an extremely attractive woman whom you found fascinating, interesting, and friendly asked you to go to bed with her?”

He was pressing her hard now. It wasn’t a question she had really ever considered. She hadn’t ever considered lesbianism to be part of her sexuality. “I don’t know. I suppose it would depend on the circumstances.”

“Would you say no because you think sex between two women is wrong, illegal, or immoral.”

That question was easy to answer. “No. I don’t have a problem with lesbians or gays.”

“Would you go to bed with her if you wanted to make her happy, to please her because you just liked her as a person?”

Kassie tilted her head to the side. It was a strange question. “Yes, I suppose I might do that. But that’s hypothetical, isn’t it?”

Joseph said nothing for a moment and made another note.

“Do you have any body piercings?”

That was an easier question. “No. Just my ears.”

“If I asked you to, would you get a body piercing of my choice?”

She swallowed. “Yes. If you told me to. It would scare me though.”

He nodded and made a note.

“Any tattoos?”

“No.”

“Same question. If I asked you to, would you get a tattoo of my choice?”

Her answer came slowly. “If you insisted, I suppose yes. But tattoos are forever, this is just supposed to last a year, right?”

Joseph glance up at her while he wrote. “I’m asking the questions. Not you.”

She nodded, remembering her place.

“How long have you had sexual fantasies about being tied up and made to perform sex acts at someone else’s order?”

This he had already asked before. “Probably around thirteen when I found my parents’ copies of The Story of O and The Joy of Sex. And other books.” She smiled confidently.”

“Have you ever been tied up during sex?”

“No.”

“Have you ever been spanked before or during sex?”

“No.”

“Has anyone asked you to be your sexual slave?”

The smile on her lips disappeared when she said softly, “Just you.”

“Do you find bondage and discipline or domination and submission morally wrong?”

“No,” her voice was very soft now. “I find them, the idea of them at least, exciting.”

“Do you consider yourself a submissive?”

That question was hard to answer. Her voice was still small and soft. “I think so. I want to please men—boys—with sex, to do what they ask. I find it…exciting…to be under someone else’s control.”

He made a few notes before finally asking, “Do you want to be my slave?” Joseph looked up from his clipboard and met her eyes. Immediately she cast her eyes downward to look at the floor. She was ashamed of her answer. “Don’t look down,” he barked at her. “Look me in the eye and give me an answer.”

It was nearly impossible to pick her eyes up off the ground, but Kassie forced herself to follow his order. This is what she wanted, wasn’t it?

“Yes. Yes, I do.”

“Take off your clothes,” he said. His voice was calmer now.

She had been expecting this. He told her it would be required. It was still strange. The only people to have seen her naked since puberty were her two short-lived boyfriends, her mother (once in the bathroom during a minor emergency), and her doctor. She had tried to prepare herself for the moment. Her mental gymnastics hadn’t done anything to make the order seem normal.

“Yes sir,” she answered. Kicking off her shoes was easy. The socks were next. Those were nothing. It was a meaningless gesture. She glanced at Joseph. He was watching her expectantly.

Her shirt was next. She unbuttoned the two top buttons with trembling fingers. Joseph waited patiently but she couldn’t bear to deal with her stupid, unresponsive body. Instead of undoing all the buttons on the front she instead yanked the blouse up over her head exposing her plain white bra for him to admire. It wasn’t much to admire. She filled it—barely.

There was another choice to be made. What to remove next? Bra or pants? Kassie chickened out; she couldn’t be bold. She slipped button on her pants and lowered the zipper. Her plain black slacks came of her hips and fell to the floor. Better that than struggling to get out of a garment that wouldn’t come free. Kassie was now in bra and panties. She wished she had been smart enough to buy a front closure bra. No regrets now.

She was limber enough to reach behind her back and slide loose the one hook the bra featured. The tension on the garment released and she was free, but not exposed. Kassie closed her eyes and shrugged her shoulders forward, letting the straps fall free. The bra was then all but off her body. She caught the scraps of white material in her hands and dropped it on top of her pants and shirt.

Oddly, once her bra was gone, it was easy to hook her thumbs into her white, lacy panties and pull them down her legs. They weren’t especially sexy, they weren’t slutty or boring either. She wanted to look good for Joseph, but it was an odd thought because he barely got to see them for a minute before the underwear was gone. She stood naked in front of Joseph and tried not to feel self-conscious.

She reminded herself she had a good body. Her breasts might be a bit small, but they stood on her chest proudly. The blond hair between her legs she had carefully shaved into a neat triangle. He hadn’t said anything about grooming so she tried to make it natural looking. Maybe he wanted her shaved bare? No hair on her pussy? She started doubting herself and brought her hands in front of her breasts, angling her hips to hide her pussy from him.

“Don’t!” he warned. “Never hide your body from me. Never.”

“Yes sir,” she said. It was easy to take the submissive route. It felt right. Her hands dropped to her sides and she looked at Joseph. She didn’t directly meet his gaze. She looked at his forehead as his eyes roamed her body. She tried not to think about what he was doing to her.

“Good. Turn around.” She did so. It was easier for him to look at her ass because she didn’t have to face him.

“Good. Turn around again.”

When she had completed the circuit she noted he was on his feet and held out his hand to her. “You have a good body,” he complimented her. “I’ll make it more perfect. Take my hand,” he said. She obeyed. “I want to have sex with you now. Shall we go to my bedroom?”

And there it was. Kassie swallowed hard and nodded her head. She reminded herself she wanted this. She followed him into the bedroom. It was odd to walk through a stranger’s house naked while he was still completely clothed. It was odd…and exciting. She liked it.

His bedroom was very nice. Kassie didn’t know that much about furniture and decorating, but she knew Joseph either had good taste or an expensive interior decorator. Joseph pulled back the cover and top sheet. “Get on the bed,” he said as if telling her to get a glass of water. “Hands and knees, face the headboard.”

It was so easy to follow his voice. Kassie wanted to obey. She knew what was coming and was excited and scared at the same time. It was the same feeling of anticipation she got when riding a roller coaster, just as the car was cresting the first hill and before it went over the other side and plunged down at breakneck speed.

Still, she didn’t know exactly how to act in front of her new dominant. When she crawled up on the bed she kept her legs too tightly together. “Open your legs a bit,” he requested. “I want to see your pussy.”

“Oh, sorry,” she apologized. “I should know better. Oh, shit. I am not supposed to talk?”

“It’s all a learning process,” Joseph said. “Yes, you may talk. If I want you silent, I’ll tell you or gag you. I prefer my slaves to be vocal. It helps them understand what I want.”

It was odd staring at the headboard waiting for something to happen. She knew what was going to happen but didn’t dare look over her shoulder at him. Then, without any warning, his hand was probing at her pussy. She tried not to flinch and move away, but the suddenness of his intimate touch startled her.

“Sorry,” she immediately apologized. “Didn’t mean to jump.”

“Don’t apologize to me,” he said. “If I need an apology I’ll get it out of you with a beating. Words of apology mean nothing to me.” While he said this his fingers stroked at her labia and then opened up her slit. She sighed with relief when he slid a finger into her cunt. “You’re wet.”

“Yes,” she agreed. “I’m excited.” His hands withdrew from her sex. One finger lingered for a second on her anus. Kassie forced herself not to shy away.

“Good.” There was the sound of some clothing being moved and Kassie definitely heard him lower his zipper. Then his body was behind hers on the bed. He pushed her legs further apart and then she felt his cock probing at her cunt.

“Do you want me to help you?” she asked.

“Yes, guide me inside you.”

Only after he said those words did she realize he was fully dressed. Or mostly dressed. His cock was out but she could feel clothing against her legs and ass. Kassie didn’t question him, she just reached between her legs, found his hard cock with its velvety head and eased it into her pussy.

At that moment she was glad she wasn’t a virgin. He wasn’t huge, but it was strange to be fucked by someone she barely knew. It wasn’t bad, just new and different. As he forced his way inside her he stretched her pussy and slipped in easily.

“I like a slave that’s ready for sex with a wet pussy,” he complimented her.

“Thank you,” she sighed. It felt good to get fucked. This is what she wanted.

Then he let more of his body fall on her. She braced her arms to accommodate his weight. His hands went around her body and cupped her tits. Only then did he start fucking her in earnest. His body slapped into hers, she grunted and arched her back to better receive his thrusts. She knew she was being used for his pleasure and she was enjoying it.

Better, she was loving it.

Kassie grinned to herself and allowed Joseph to fuck her. It was wonderful.

They were both excited by their initial coupling. She wasn’t sure how long the sex lasted, but Joseph came fairly quickly. When his hot jism was spurting into her pussy she came as well. Her body shook with the little orgasm and she moaned in pleasure.

“Very good,” Joseph said when he was done cumming. He rested on top of her body a moment and then pulled out of her cunt. “Don’t move,” he told her. He moved off the bed and busied himself at the dresser. Kassie wondered what he was doing. She could feel his spunk slowly seeping out of her pussy. She wanted to fall to the mattress and rest. She wanted to clean herself.

“You know that as my slave, your body belongs to me. The only thing that belongs to you once you walk into this house is your mind. Do you understand?”

“Yes,” she said. A thrill of fear ran down her spine.

“Good.” There was a flash and the artificial click of a digital camera. She knew what he was doing. He was taking picture of her ass and her just fucked pussy with his cum dripping out of her. She wasn’t sure how she felt about that but she wasn’t going to quit now. He took four or five more pictures of her sex. “Like your body these pictures are mine. I’ll do with them as I please. Do you understand?”

“Yes, I do.”

“Good. You may get up and clean yourself. The bathroom is that way.” She turned around and slipped off the bed. Joseph had already re-arranged his clothes. His cock was put away and he was calm. Happy and calm.

Kassie didn’t run to the bathroom, but moved quickly. She didn’t want to drip Joseph’s cum on his carpet. On the toilet she allowed his cum to drain out of her pussy and she wiped herself with a wet washcloth. Coming back out to the bedroom, Joseph was waiting for her with a folder of papers.

“I think you passed the interview,” he said with a smile. “In here is your agreement, your first week’s pay, and instructions you should memorize. Your schedule is here as well. Any questions?”

Kassie couldn’t keep a giant grin off her face. “No. I’m sure I’ll have some, but not right now.”

“Good. Tomorrow when you get here, be sure to shave your pussy. I don’t like body hair on my slaves. Besides, pubes look terrible with your uniform.”

 

 

Chapter Two

 

ARRIVING AT JOSEPH’S house the next morning Kassie found the hidden key as he had promised in a flowerpot on the front porch. She let herself in and closed the door behind her. As he had said he wasn’t home at the moment; that didn’t mean she wasn’t still his slave. In the entry hall she opened the closet and found several shelves inside. On the shelves were cardboard document boxes. They each had a number. Hers was eleven. She opened the box and found her uniform inside. It consisted of the tiniest G-string she had ever seen and a pair of ballet flats. It was bright red and seemed almost the sort of thing that would be given as a joke at a bachelorette party.

Still, she knew what she was supposed to do. Kassie stripped off her clothes, placed them carefully inside the box, put the box back in the closet, and closed the door. Only then did she pull on the G-string. Joseph knew what he was doing. It was just large enough to contain her labia, covering her shaved pussy. The string went uncomfortably between her buttocks, and she wiggled her hips to find the right fit for the garment. Then she slipped on the ballet flats.

It was going to be an odd day. Her first assignment, left on her kitchen table, was to sort receipts by vendor and date. The box left for her was huge.

“Why does he was a sex slave if all I’m going to do is filing in the nude?” Remembering she was supposed to be Joseph’s personal assistant, not just sex toy, she set to work. It wasn’t much different from an office job. The filing took most of the morning. When she was done with that task she set to job number two.

“Clean the kitchen?” Kassie read aloud as she shook her head at the note. “Weird.”

The kitchen was mostly clean. She washed a bowl and spoon that was in the sink; presumably from Joseph’s breakfast. After checking the dishwasher and finding it empty, she found some cleaning supplies under the sink and set to giving the barely used kitchen a basic cleaning.

When the phone rang she nearly jumped out of her skin. “Fuck,” she cursed and wondered if she should answer it. Padding over to the handset mounted on the kitchen wall she saw the caller ID displayed Joseph’s name. Taking a risk she picked up the received. “Hello?”

“Kassie, why weren’t you answering your cell phone?” Joseph asked abruptly.

The question threw her, but she managed to say. “I put it in the box with my clothes,” she admitted. “It’s on vibrate. I didn’t hear it in the kitchen.”

“Fine. Go and check it. I’ll be in later this afternoon.” He disconnected.

When she checked her phone there was a list of tasks in her messages. She read them and shook her head some more. “He’s a strange one.”

Following the orders she went to his bedroom, laid down on top of the covers, and took a selfie showing her tits and face, then she lowered her G-string and took a picture of her bare pussy. She saved these and closed her eyes. For the most part Kassie liked masturbating, but usually she needed some impetus to get her going. Filing and kitchen scrubbing, even in the nude, didn’t get her excited. Still, she knew she needed to perform for Joseph, even if he wasn’t in the room with her. Whipping up a quick bondage fantasy she busied her fingers in her twat, spending extra time with her hard little clit, until she came. Then, still following orders, she took another picture of her pussy.

The hard part was sending Joseph the pictures. She knew her body was his, but what was going to happen to these pictures. They were sure to live on the internet for years. Once she pressed the send button on the phone Kassie tried to forget about that fact. A minute later her phone vibrated with a message. Very good. You have a pretty pussy. Now have lunch. Eat whatever you want in the fridge. Then you can take a nap or watch TV in my bedroom. I expect you to be in my bed when I get home.

These orders Kassie was happy to follow. She made herself a sandwich, eat it, cleaned up her mess, and retired to the bedroom to watch trash television.

She must have drifted off to sleep because she woke up to a door slamming. A minute later Joseph was in the bedroom while she was still trying to push sleep from her brain. “Good, you’re in bed. That will make this easier.”

She nodded but didn’t understand. “Okay,” she agreed.

“Stand up,” he ordered.

She obeyed. Her ballet flats were on the floor but she still wore her tiny G-string. Happily it was still in place but it still felt odd to her sex; she was more of a bikini or boyshorts girl. “Very nice. You’ve still got great tits. A little small, but we can fix that I think. Take off your uniform, get on the bed, hands and knees.”

This time it was easy to take off her clothes. She was only wearing one item. Being naked the second time with Joseph was more natural. Once she was naked and back on the bed she expected him to mount her again for another vigorous fucking. Instead he was occupied at the dresser again. She wiggled her ass at him, teasing. He didn’t see. His back was turned.

“Do you know what this is?” he asked, walking around to the side of the bed. He displayed a metal object with what had to be a glass jewel. It was roughly the shape of a lava lamp with the jewel serving as the base. She studied it for a moment before realizing what it was. “Is that a butt plug?” she asked.

“Very good,” he complimented her. “So you know what it is and where it goes. Have you worn one before?”

Kassie vigorously shook her head. She was a little scared now. “No. Never. I’m only eighteen.”

“That’s right you are. It’s high time you really explored your sexuality. Get down on your elbows. That’ll force your ass up in the air a bit more. It’ll be easier to put in that way.”

She nodded and lowered herself down. Her fingers were trembling again. She grasped the sheet and tried to calm herself. Joseph went into a monologue. “It won’t hurt. It looks big, but you’ll find it goes in smoothly with just a bit of lubricant. Which will be cold, of course. Brace yourself.”

She did so and felt a cold dollop of the thick gel on her anus. Joseph’s fingers probed gently at her, pushing slightly against her tight sphincter. When he penetrated into her anus, she clenched up. “Relax,” he ordered. “You’ll enjoy this. Most women do. All of my slaves do.” He withdrew his finger. She glanced over her shoulder and saw him smearing more lube on the plug. She took deep breaths and readied herself.

“This is all about relaxation. The more you fight it, the more it hurts. Don’t fight it. Give yourself up to me like a good slave. Can you do that Kassie?”

“Yes,” she said and hoped she could.

“Okay, here we go.” The rounded tip of the butt plug pressed against her anus for a moment, then Joseph started pressing it into her. It hurt for a moment. She felt her ass opening up. It felt wrong…oh so very wrong. It hurt. He had lied to her. He kept pushing and she tried to keep herself from freaking out or pushing back. Just as the pain level reached the point where she was about to start begging for him to stop, the pain was suddenly gone and the stretching sensation stopped as well.

“Did you pull it out?” she asked.

He laughed at her. “No, of course not. It’s right in place where it should be. Don’t you feel it?”

For a moment she didn’t. The lingering pain and stretched sensation overpowered everything else. Then she concentrated and realized something was in her ass, like she needed to go to the bathroom. Her anus was being held open by the stem of the plug.

“Give me your hand,” Joseph said. He guided her fingers to explore the object in her ass. She felt the fancy green jewel covering up her asshole. She slipped a finger under the jewel to feel the stem and the way it was inside her.

“Oh,” was her reaction.

“It’s very pretty on you,” he said. “Let me get a few pictures.” Out came the camera again and a few more pictures of her intimate areas were recorded for his pleasure. “Okay, roll over and open up your legs,” he said. “I’m going to fuck you now.”

She moved carefully, not wanting to unexpectedly expel the plug, but it seemed to be firmly in place. She opened her legs and looked between her legs to see Joseph taking off his clothes. For an older man he had a nice body.

He didn’t say anything as he slipped onto the bed. She half-expected him to shove his cock to her face, but he was already erect. A warm-up blowjob wasn’t necessary. And then he was on her, and then he was in her. His cock nudged open her pussy and filled her inner sheath, stretching her nicely.

“Oh,” she moaned, not realizing she was making any noise.

“Am I hurting you?” he asked before he truly started fucking her.

“No, no,” she assured him quickly. “I’m just so…full. Your cock and the plug are so much.”

His face was only inches from her. He smiled. His teeth were white with one lower incisor being just a little bit crooked. It was charming. “Good. I’m sure you’ll find having a butt plug in while being fucked enhances every sensation.”

“Uh-huh,” she vaguely agreed as he pushed all the way inside her, bringing his pubic bone in contact with hers. He wasn’t shaved at all. That was okay, she liked the way his hair tickled her cunt.

And he was right. She was full and it intensified everything. At that moment she realized this is what it must feel like to be fucked by two men at once: one in her pussy and one in her ass. Kassie wanted to push out but she was certain that expelling the plug would be frowned on to say the least. She lay there and enjoyed his fucking. His cock going in and out of her cunt; her hands roamed his back going down far enough to clutch his ass; he unexpectedly kissed her neck and when she turned her head he kissed her lips and invaded her mouth with his tongue.

Her first orgasm was small and unexpected. Maybe it was because of the plug. She knew there was a lot more going down around her pussy and ass than normal. It was nice. Then Joseph increased the pace of his thrusts and she felt the need to clamp down on the plug to hold it in place. She didn’t want it to slip out. That in itself was almost enough to make her cum but she held off another minute until Joseph grunted and emptied his balls into her pussy. That pushed her over the edge and she shook and cried with the shivers of pleasure that nearly paralyzed her body.

“Oh, thank you,” she whispered. Kassie didn’t want Joseph to hear, but he did.

“You’re welcome.” Joseph pushed himself off her body and ordered her to turn over on all fours. She did so, presenting him with her ass. She could feel his fingers digging around her anus and once he firmly gripped the jeweled base of the plug he pulled and eased it out of her ass.

At first it didn’t want to move. She clamped down on it again, but Joseph was insistent and eventually the toy came out. She half expected it to emerge with a little pop, but that wasn’t the case. Its reemergence was silent. It hurt a bit coming out, but even in that there was a little pleasure.

“Take it,” he said to her. “Go to the bathroom and clean it and yourself.”

Kassie was a bit squeamish when she accepted the toy into her hand. To her relief it wasn’t covered in shit, but just the lube with a light amber tone. Moving quickly she did as he ordered in the bathroom. Her ass felt oddly empty and stretched. That was good she decided.

When she returned with her pussy, ass, and butt plug clean he asked her if she enjoyed the little torment he had put her through.

Kassie nodded her head. “Yes. It felt weird, but in a good way.”

“Very good. We’ll have to try anal beads on you as well. Be sure to arrive early tomorrow morning. We leave from here at eight a.m. Remember to dress professionally.”

 

The next morning Kassie presented herself at Joseph’s front door in her neatest skirt, modest heels, and button down shirt that showed absolutely no cleavage. Her mother said she was the epitome of a professional woman. Kassie let pass the reference that some prostitutes referred to themselves as professionals.

“On time,” Joseph said upon answering the door. “Good. Come inside.” She didn’t know what to expect once inside so she so started to take off her clothes but he immediately stopped her. “No time for fun, just lift up your skirt and drop your panties.” He closed the front door. No need to advertise to the distance neighbors what was happening in his house.

Kassie followed his instructions and pulled her skirt up to her waist and then lowered her pretty blue silky panties to the floor. When she looked up he was holding her cardboard box with the “11” on the side. She dropped her panties in the box and he then handed her a small bottle of lube and the same butt plug she had worn the previous day.

“Put this in,” he told her with a wicked smile. “Squat down. It’ll be easier to insert that way.”

Nervously Kassie fell to her haunches, smeared a good amount of lube on the bulbous plug and reached down between her legs. It took her a second to find the right hole and right angle, but then it slipped up easily inside her anus. She stayed squatted for a minute to make sure it was firmly in place, probing around the edge of the jewel wondering exactly what it looked like. She realized Joseph had pictures from last night, but she wasn’t bold enough to ask him to see them.

“Ready?” he asked her. She was still squatting pondering her position when she realized she wasn’t wearing any panties.

“Do I get to wear any…?” Then she noticed her tiny uniform G-string dangling off his fingers. Today it was black. Classy.

She stood up and took the scrap of cloth from Joseph and pulled the tiny panties into place. It was large enough to just cover the jewel of the butt plug and when she settled it into place and dropped her skirt Joseph handed her the bottle of lube. “Put this in your purse. You might need it.” He opened the front door. “Let’s go. Lots to do today.”

“Where are we going?” she asked. He indicated her to get in the passenger seat of his very fancy sedan. Once he put the car in gear they drove quickly from his suburban home into the city.

“Lots of meetings,” he informed her along the way. “You’ll be my personal assistant today.”

She arched an eyebrow at him and he shook his head. “Sorry. No time to play today. Serious meetings. You’ll be fetching papers, running around being a general help to whomever has a need. None of it will be sexual, sadly.”

“So why am I wearing a butt plug?” she asked, shifting uncomfortably in the seat. It was one thing to have a steel plug in her ass, it was another entirely to have it being forced deeper by sitting on it.

“Because you are my slave,” he told her.

That was reason enough apparently. Once in the city they parked in one of the many garages, walked directly to a nearby hotel—for a moment Kassie thought he had been teasing about the no sex need for her today—but they went to a meeting suite and proceeded to go through a whirlwind series of meetings that made no sense to Kassie. As far as she could determine he was some type of financial advisor. If his business was legal or not Kassie hadn’t a clue.

She was sent to get papers, coffee, other drinks, food, pens, a bottle of hand lotion for a client with dry skin, extra binders from the hotel supply closet, directions to the closest vegetarian restaurant, extra napkins, graph paper, a custodian to empty the trash, and a hundred other minor tasks. She had never been so busy in her life. The butt plug went from being an annoyance to a sexual stimulant to nothing more than a vague feeling filling her bottom. When she stopped in the middle of the day to pee after lunch it threatened to slip out, so she removed it, finished peeing, then reinserted it without a problem. Kassie took an odd bit of pride in that successful maneuver, then shook her head at her strange, twisted outlook on what she should take pride in.

The clients Joseph met with barely noticed her. She wasn’t sure if she should be offended that older men didn’t give the pretty girl waiting on them a second glance or relieved they didn’t give her more pressing problems to solve.

When it was all over and Joseph drove her home to his place he told her no further services would be needed that day. She was disappointed. She wanted to have sex again. The butt plug had worked as a mild stimulant all day and she felt randier than ever. Except for the exhaustion.

“Should I take out the plug?” she asked him when they arrived at his house. She now had a twenty minute drive home in her decrepit vehicle.

Joseph shook his head. “Wear it home. Take it out when you get there. Leave it out overnight. You’re expected back here tomorrow morning at nine a.m. Put it in before you leave your house.”

She nodded, got in her car, and drove home. It was just after she reached the halfway point did she realize her panties were still in the box in Joseph’s house.

Seeing as she was an adult Kassie’s parents gave her a bit more privacy than before. She hoped they didn’t realize she was using that privacy for the care and maintenance of sex toys. Once the plug was out Kassie couldn’t resist and put herself to sleep with a nice masturbation session.

In the morning Kassie arrived on time at Joseph’s door. The hidden key was missing so she was reduced to ringing the bell. Instead of Joseph answering the door was opened by a woman wearing nothing more than a small, semi-sheer bathrobe. Kassie gawked at her in surprise.

“You must be Kassie,” the other woman said. “I’m Joanie. Come on in.”

“Where’s Joseph?” she asked. The door remained open but Kassie didn’t move. She was in the right place, but this woman wasn’t supposed to be here.

“He’s not here today. That’s good. We can play. Come on in,” she said again, encouraging Kassie with a little come here gesture. She stepped back from the door, leaving it wide, opened the closet door where the cardboard boxes were stored. Joanie stripped off her robe and hung it on a peg inside the closet. What little the robe had been concealing was now fully on display. Joanie was older that Kassie, she figured that out right away. She had a head of beautiful flame-red hair that fell below her shoulders. While all her skin was on display Kassie’s eyes were drawn to the number of freckles over Joanie’s shoulders, arms, and chest. The freckles went very low on Joanie’s chest, just above her pink nipples.

The only clothing she wore was a tiny G-string like Kassie’s. Joanie’s was green and barely hid her slit.

Reluctantly Kassie stepped inside. Joanie shut the door and waited. “You are going to strip, aren’t you?” Joanie prompted.

“Oh. Right.” Kassie went to the closet, opened up her box, and slowly took off her clothes. She was decidedly uncomfortable getting naked in front of a woman she didn’t know, but since Joanie was already naked and expected the same of her, she saw little room to argue. When she removed her panties and plucked the pink G-string that Joseph had left for her—did he buy them in bulk? she wondered—Joanie stopped her. “Wait. I need to inspect you first,” she said.

“What?”

“Bend over so I can see your butt plug. Joseph wants confirmation you’ve followed orders.”

The appearance of the other woman in Joseph’s house had thrown her and Kassie had all but forgotten the plug was in her ass, as instructed. Still, she obeyed the older woman, turning slightly and bending forward