Working Late Ch. 02

"So that's what this is all about? A fucking audition to be your slave?" She had a hard time choking those works out. This was totally unbelievable, she thought.

"I wish you wouldn't think of it that way, my sweet. I can tell you are looking for someone who can relieve you of the burden of control you bear in your ordinary life. You are looking for someone you can trust completely, who will care for your every desire and allow you the pleasure of having one focus and one focus only - serving him."

She mulled his words over. Yes, it was true. She was, she supposed, wanting someone else to take care of her, to place herself in another's hands, trusting that her needs would be met. But this wasn't exactly what she'd had in mind. Or was it? She was engaged, for pete's sake. This conversation shouldn't even be happening.

"I think you and Kim should spend some time talking, so you can ask her some of the questions I know are running through your mind. I'd like the two of you to go into the living room and sit by the fire. I'll prepare some drinks for you and leave you alone to talk. Jamie, dear, you will, of course, need to set aside your personal feelings for Kim in order for you to get the answers to your questions. I can assure you she feels no ill will toward you. On the contrary, she is pleased that you are here and truly wants you to willingly give yourself to me. Remember, my pleasure has been her only concern for the past two years, and she believes you will please me."

After a nod from Ian, Kim slid off the bed and walked into the living room. Jamie wasn't sure she wanted to follow.

"I know your desire for information outweighs your need to act independently, sweet one. Go on. She won't bite." He grinned, and she could hear him silently completing that last sentence with "unless you want her to." However, he was right. She DID want answers. She wanted to know what made Kim so obviously content with this lifestyle. She wanted to know what was expected of her, what she did that pleased him, and what didn't please him. She wanted to know if she was satisfied - in more ways than one.

She and Kim sat on the floor in front of the fire. Kim immediately indicated that they were not allowed to sit on the furniture unless invited to do so. Normally, she spent her time kneeling for Ian, but tonight was an exception. They would sit however was comfortable, although they would remain on the floor. Jamie drew the sheet tightly around her, feeling awkward and embarrassed for Kim's nakedness.

Ian brought them a pitcher of margaritas and two glasses and retired to the den, leaving them alone.

"If you'd like," Kim began, "I can tell you why gave myself to him. Why don't you pour for us while I explain how I ended up here."

She nodded. Yes, perhaps that would be a good place to start, she thought, as she reached for the pitcher. She was sure she'd need plenty of alcohol to get through this evening.

Kim had been raised in a strict home, although both her parents were absent much of the time. She found it hard to take care of herself, hard to make her own decisions, because someone had always made them for her. Ian offered her a place to live, freeing her from her parents' rules, and the knowledge that she would be completely cared for. In return, he expected complete submission. She existed solely to please and pleasure him. She also cared for the house, doing cleaning, laundry, and cooking, always to his specifications and always to please him, her Master. He would take her as he pleased, share her with whomever he wished, and deny her pleasure as he saw fit. While having to discipline her was not his biggest turn-on, it was necessary to ensure she understood when she had displeased him. She was happy, having nothing to worry about except pleasing and pleasuring her master. It was an offer she could not have refused. An hour and a pitcher of margaritas later, Kim was finished with her story.

"So why, then, is he giving you to someone else?" Jamie asked, her tongue feeling fuzzy.

"Because I need more training and more severe discipline than he can provide. It's an amicable separation."

Jamie was having a hard time comprehending all this. She wasn't sure if it was the alcohol or the utter strangeness of this conversation. But either way, she wasn't entirely sure she wanted to stick around to find out more.

"Jamie, why don't you tell me about what it is you're looking for."

Jamie was silent. She had no idea what she was looking for. She was attracted to Ian, had been since the day they met, but she had no idea that lifestyles like this existed outside of X-rated movies and books.

"Ok, I can tell you aren't sure how to answer that, and that's alright. Why don't you tell me about your past relationships, what you liked and what you didn't like. Maybe that will help you realize why his offer tempts you."

Jamie thought for a moment, then began to talk. She described always wanting the "bad boys", the ones who would treat her badly but provide her hot, steamy sex occasionally. She felt like a whore, most of the time, unable to get a boyfriend, but the first one her male acquaintances would call when they were horny and alone with no other prospects. She liked that feeling of being wanted, of being desired, but without the responsibility of a relationship. She also liked the rush she got from doing something forbidden. Most of her friends had no idea how many men she'd slept with, or who any of those men were.

In college, there had been many, many men. Most lasted one or two encounters. Sometimes, if they were very good in bed, she might allow three. But that was the limit. There was also a string of one-nighters, men she met at frat parties, friends of friends, strangers in bars. The less she knew about them, the better. They simply helped pass an otherwise empty weekend.

But there were some who were memorable, for their own unique reasons. There was Marco, the football star of their small liberal arts college, who was a genuine asshole, but had such an incredible body that she simply couldn't resist offering herself to him. Lance the Cop had been a risk she took one night at a frat party, letting him take her home with him to the room he had in his parents' basement. It had been the first time she had been able to express her desire to be taken from behind. He bent her over the bed, fondling her breasts as he pushed into her.

Ian was a French Canadian. One of his parents was French, the other from the West Indies. He was a Casanova, and although not particularly handsome, there was something about him women found irresistible. She knew of at least two of her sorority sisters he had slept with, before they ended up on a mattress in a frat house basement after one very wild party. The next day was graduation, and although they had only finished their second year, he was leaving to go home to Quebec. He was only one of many "goodbye fucks" she had over the years.

Rob Photo was the boy from a neighboring state university who worked for the Party Pic company her sorority used. She ran into him numerous times before ending up at his apartment one winter evening. She liked him. He was one of the few who talked to her, about himself, about his dreams, about his life outside of the bedroom. And he seemed genuinely interested in her. He would call her sometimes, just to talk, which was nice. She had continued that relationship into June, before he moved back to Chicago after graduation.

There was Mitch, back home, an enemy-turned-friend when they both felt as though the whole world had deserted them. She would see him during the summer and on breaks. She would sneak out of the house after midnight, and he would pick her up and drive her to his apartment downtown, where they would share a beer, fuck, and then talk about life until it was time to get her back home before her mom woke up for work. But for them, the sex was separate from their friendship. He, too, was an ass, but she understood why. Everyone he had ever cared about had left him, dying, most of them. First his dad died, then two brothers, a classmate, and finally his mom. He protected his heart as though it were the world's most precious gem. She was the only one, as far as she knew, he had let past his carefully constructed barriers. He understood her need to have rough sex, to be taken as though she had no choice. But he refused to kiss her, a peculiarity she never did understand. Perhaps he, too, avoided a certain level of intimacy, even with her.

She talked at length about Jason, the one she thought she might marry someday. She had met him at a frat party at a state university an hour away. He had come late, from work, and joined the game of "I Never" she was playing with his friends. It soon became clear that the two of them were the most adventuresome ones at the table, and before long, they excused themselves to get some air. He kissed her against a tree in the backyard, gently but demanding her participation. They became lovers that night, in a borrowed apartment, and in the following months she spent weekends at the house he shared with his mother. Jason, she thought, was different. Over time, she knew she loved him. He was more than just a conquest, more than just a sometimes bedmate. Although he had yet to satisfy her, he tried. And he made her feel like the most beautiful woman in the world. But he couldn't quite let go of his ex-girlfriend, and eventually she had to tell him goodbye. She had given him her heart, and he hurt her, beyond forgiveness.

Ever since then, she had returned to her old ways, keeping her heart out of the bedroom, preferring semi-anonymous encounters with men she knew she would not see again. The strange thing was, as much as she enjoyed sex, and the pursuit leading up to the sex, she was never satisfied. None of them had tried to satisfy her. Few asked if she even came, and those who did, believed her when she lied. Jason was the only one who truly enjoyed the foreplay, even more than the sex sometimes, she thought. And it was with him that she felt at least some satisfaction, although it was more from the knowledge that she was pleasing him, rather than being pleased herself. But now, she was engaged to Steven, the one she rebounded with after Jason. He loved her, had moved across the country to be with her, and yet he had no idea that she didn't love him in return. She was engaged because she didn't know how to tell him no, didn't want to hurt him the way she had been hurt.

Without even realizing it, she began to cry. She felt so alone, she sobbed. She was so tired of feeling like nothing more than a cheap whore, so tired of giving herself to men and getting nothing in return. What was wrong with her, she wondered. What was it about her that made men want to sleep with her, but wouldn't make them date her? And why couldn't she get out of a relationship she didn't want to be in? But if she ended it, she'd never be able to face herself, knowing she had caused someone the kind of pain she so desperately tried to avoid.

There were soft hands stroking her hair, whispering to just let it all go, to cry it out, that it was ok, she wasn't alone. As her sobs began to slow, there were soft kisses on her eyelids, down her cheeks, and then soft lips found her mouth. She returned the kisses like one who was starved for affection, letting her mouth open to receive the tongue that wanted to explore.

Sshh... lie back and let me love you, she heard. Don't think, just feel, the voice urged her. She slid down, lying on her back. She was dimly aware of the sheet being opened, of hands massaging her breasts, of warm wet soft lips gently sucking her nipples. Her hands reached for the source of her pleasure, only to be pushed back to the floor above her head. She was wet, and soon warm fingers found their way inside her, thrusting first, then applying pressure to that secret spot inside that made her moan. Her clit was being rubbed, firmly and gently, while the thrusting continued. She began to writhe, feeling the tension building and the familiar heaviness inside that preceded her climax. The lips returned to her nipples, alternating between slowly circling them with the tongue, exhaling lightly to increase their erectness, and gently biting them while flicking the tongue over the tip.

She lost all sense of time as the fingers brought her so close, then slowed for a few moments before building her back up again. She wanted to come so badly, yet she didn't want the pleasure to end.

The mouth on her nipples disappeared, and she was aware of someone kneeling over her face. She could smell a salty, muskiness that was strangely familiar.

"Do you want to come, Jamie?" Ian's voice was some distance away.

"Oh yes, please, yes," she moaned.

"Make her come, and then you will be rewarded with your own."

She hesitated for the briefest of seconds, then arched her head up to find the warm, wet flesh that was her ticket to release. She swirled her tongue around, quickly finding a large ridge, and she was rewarded with a moan. She spread her legs farther, hoping to entice Kim to find her clit again.

"Use your hands on her too, not just your mouth," Ian commanded. "The quicker she comes, the greater your reward."

Her hands found the girl's slick, tight opening, and she eased two fingers in, slightly twisting them as she slowly withdrew. She paused a second, then plunged them back in, eliciting a yelp from Kim. This was how she liked to be fucked, and she was pretty sure Kim was the same. The long, slow withdrawal, a pause, and a swift re-entry was the surest way to get her off. Her tongue continued to flick her clit, but she knew as Kim's orgasm approached, she would need a different kind of pressure to bring maximum relief. As Kim's cunt tightened around her fingers, she could feel more contractions deep inside that signaled the beginning of her orgasm. Jamie sucked Kim's clit into her mouth, holding it in place with her teeth, flicking it back and forth with her tongue. As she did so, she slid a third finger from her other hand into Kim's dripping hole.

Within minutes, she felt the strong contractions start. She withdrew the third finger and, as Kim began a high-pitched whine, she slid it quickly into her ass, wiggling her fingertip in the process.

That was enough to send Kim over the edge, and she began to shake, grinding her dripping cunt into Jamie's face. When her orgasm subsided, Jamie gave her clit a lingering lick and withdrew her fingers, and Kim rolled to the side.

"Good girl," Ian said. "That was well done, my dear."

Jamie was so aroused she couldn't speak. She had no idea that servicing a woman could be such a turn-on, but she was keenly aware of the emptiness of her own body and wanted desperately to find relief. As her eyes adjusted to the darkness, she was aware that Ian was sitting in his club chair, sipping Scotch as he watched them. She wondered how long he had been there.

"Kneel over her the way she just did to you," Ian commanded. "Open yourself to her tongue, Jamie. Kim, you will provide her with an orgasm she won't forget, or you will pay the consequences."

Kneeling over Kim's face, she closed her eyes and tried to imagine the tongue she felt was a man's, that the fingers rubbing her G-spot were those of her fiancé. She willed herself to imagine his face, but instead the image of Kim, lying on Ian's bed, filled her mind.

As Kim's fingers expertly aroused her again, she began to moan, thrusting her hips toward her mouth, wanting her to increase the pressure on her clit. She was getting so close. Her juices began to flow, and Kim lapped at her open cunt like a kitten. Kim thrust two fingers in and out of her sopping pussy, gently biting her clit as she sucked it.

All at once she felt the wave of pleasure she knew would take her to her climax.

"Oh god that's it don't stop please don't stop oh god now I want to come now now please..." She was incapable of thinking. Her whole universe centered on her pussy, where the pleasure was so intense she almost couldn't stand it.

She leaned forward, her head near Kim's pubic mound, spreading her knees wide, wanting to give Kim total access to her flesh.

As she began to come, she felt hands on her hips and Kim's fingers left her pussy. They were replaced by the unmistakable hardness of a cock, which stretched her and filled her, pushing her over the edge. She let out a low, deep moan and let the waves of orgasm overtake her. She could feel him thrusting once, twice, three times before he pulled her firmly against him and shot jets of hot sperm inside her spasming pussy.

Some time later, after they had been lying quietly on the floor recovering from their respective orgasms, she looked over to find Ian studying her face.

"What is it?" she asked.

"You please me," he responded.

"I'm glad," she said.

"I am also surprised at your skills with Kim," he said. "I was not aware that you had had previous experience with pleasuring a woman."

"I don't," she whispered. "I just did what I knew I liked, and hoped it would work."

"Kim," he said as he turned to the silent form on his other side. "Did she please you?"

"Oh, yes, Master, very much so."

"I'm glad to hear that. I am also pleased with you, Kim. You may go wash up now. I'd like to talk with Jamie alone. You will wait for me in the bedroom."

Jamie lay still as Kim slipped out of the room, unsure of what would happen now.

"I must admit at first I was unhappy with your reticence earlier. However, after having had a chance to listen to your conversation with Kim, I better understand why. I am glad to see that you were able to let go and participate when Kim initiated lovemaking with you. I know that giving up that control must have been difficult for you. You did well. I am offering you the same arrangement Kim had, with a two month trial period. For two months, you will be here every evening from six until ten for training, at which time you will return home. We will continue our working relationship as though this arrangement does not exist, of course. By day we will be co-workers, but at night you exist only to please me. I will expect your total commitment and cooperation. No exceptions will be tolerated, and punishment for disobedience will be swift and memorable. If, after two months, I am still satisfied with your progress, you will move in with me, and will be my slave. I have also come to the conclusion that you will marry Steven as planned."

She was silent for a moment.

"May I speak?"

"Of course."

"This is a very big decision, and I don't like to make big decisions without my clothes on. May I have some time to think about it?"

"I'm prepared to give you until Monday to decide."

"And if I don't accept?"

"No hard feelings. Nothing at the office will change."

She gave this some thought before responding. This had been the most bizarre night of her life, and she knew this decision would be a life-changing one. She just wasn't entirely sure she could commit to surrendering to someone else entirely. On the other hand, it was becoming increasingly clear that he was capable of tuning into what excited her, anticipating her desires even before she did. But how could she do that to Steven? Hell, she already had.

"I'll think it over, and I'll let you know on Monday."

"If you decide the answer is yes, then be here at 6 to begin your training. If you don't show up, I'll know the answer is no."

"Fair enough."

"You'd better go now. I have unfinished business awaiting me in the bedroom."

Jamie gathered up her clothes and quickly dressed.

"Goodbye, Red. I'll see you Monday. Lock the door when you go."

"'Bye," she whispered, searching his face; for what, she wasn't sure.

He walked past her, down the short hall into the bedroom, and shut the door without looking back.