The Ivy League

by Parker, Ruby

  His pride swelled slightly when he saw the blush rise on her cheeks at the mere sight of his naked torso. She paused, not comfortable with the thought of removing his only remaining article of clothing. Somewhere, in the back of his lust-hazed mind, curiosity began to set in. Could this be the girl’s first experience with a man? He had ordered this same fantasy many times, and most of the girls were able to satisfy his desires quite effectively. But none of them were as good as this girl at staying entirely in character. His hand reached for hers, and before she had time to react he placed her hand on the steadily growing lump in his groin.

  The breath stuck in her throat, and she yanked her hand back as if the touch of him burned her. She couldn’t look anywhere but a single spot on the floor. She knew she had already slipped up a lot, but she still wanted to look professional, and not let on that this was her first time. She swallowed the stalled breath and forced herself to reach for him.

  He allowed a sigh of pleasure to play on his lips while he showed her how to touch him through the front of his still buttoned pants. He was swelling to a point of aching, and he needed some friction to satisfy him, at least momentarily. Her fingers felt around the length of him, exploring his shape and size through the fabric. The heat on her cheeks grew with his size as she touched him tentatively. Her fingers played up and down his shaft as he leaned into her touch.

  “Remove my pants,” he whispered into her hair. “I want you to feel my bare flesh.”

  Sara complied, her fingers shaking as she pulled down the zipper. The woven silk pants dropped to his ankles with a gentle push over his hips. The large bulge in his black boxer briefs held her attention as she tried to make out in her mind what was beneath the cotton fabric. She had seen a man naked before, but it somehow looked different in person.

  He watched her, as she trembled while obeying him. He knew already that he would be ordering her again. She was taking her time, hesitant with every action, but still compliant. So gentle, delicate, unsure.

  Her fingers hooked around the band of his underwear, her eyes glancing up at him, unsure, as she slowly pulled them down. It was the first time she had ever seen a man so close, so raw, and so hard. It looked so strange, sticking straight out at her with a contoured tip. As she continued to gawk at the stiffened appendage it twitched, as if winking at her. She jerked back slightly, looking up to notice the smirk on his face as he watched her staring at him.

  “Touch me,” he said with a silent chuckle in his words. He could see the heavy blush on her cheeks, the shocked curiosity in her eyes. She was absolutely perfect.

  It took everything Sara had to keep her hands from shaking as she reached out for him. Her fingers ghosted over the hard flesh. It felt like nothing she would have ever expected. The skin was so soft, but beneath it was pure muscle, tensed and hard. Sara could feel the heat travelling up her arm, into her body, settling like a hot coal in her belly. Her knees threatened to give out and send her crumpling to the floor. She nearly jumped out of her own skin as his hand wrapped around hers, pulling her back and forth against his engorged flesh.

  “Like that,” he said, his voice coming out in ragged huffs as he guided her to touch him. She found it oddly empowering that she could affect him in such a way, especially when he had such a stranglehold on her. Her movements became bolder as she stroked him with a mix of rough and gentle, fast and slow. She explored every sense of him that floated around her as she did, trying to come to terms with the feelings he had awoken in her.

  Chapter Five

  “Taste me,” he said, his voice low. His hooded eyes were locked onto her, but they threatened to roll to the back of his skull by the pleasure that racked him with her simple touching. He had never had a girl this good before. He could see her hesitation. The uncertainty that shone in her eyes fueled his passions. This girl was very good.

  His fingers curled into her soft hair, gently pulling her closer to him. He didn’t want to force her into anything, rather just guide her to what it was he wanted from her.

  “You might like it,” he mumbled.

  The smirk that curled the sides of his lips didn’t do anything to calm Sara’s nerves. She could barely bring herself to look at it, much less put it in her mouth. And even if she did, she wouldn’t know what to do with it after that. She knew she could say no, put her dress back on and walk out of the office. But he had paid her a hefty sum for her services. Services that she had thought long and hard about, and decided it was something she was sure about. It was just this one night, and she had to deliver.

  “Just the tip,” he said, seeing her persistent hesitation. He found he liked it more than he would expect. Her hand was still on his shaft, as if she had forgotten it was there, while her eyes looked up at him, round with a hint of fear behind them. His hand on the back of her head coaxed her forward.

  Sara licked her lips unconsciously as the request rolled around in her head. She allowed him to pull her closer while she closed her eyes. If she actually saw it, she thought she might pass out. Her lips puckered around the head. The flesh was so soft and hard at the same time. Her eyes opened to look up and into his.

  “That’s good,” he said, the words coming out almost as a moan. “More.”

  Sara wasn’t exactly sure what he meant by more, but she found that she was oddly pleased by his reaction, so she again kissed him. His hand held her closer to him, and she opened her mouth to accommodate the gentle thrust of his hips. His flesh filled her mouth. His hands guided her in a rhythmic back and forth motion.

  Her touch was unsure. He found that vastly more pleasurable than the usual skill that these girls had. It wasn’t as physically stimulating, but it was inherently pleasurable for him to teach her. Even if it was just pretend.

  “Use your tongue more,” he said, continuing to guide her. Sara pulled back, running the tip of her tongue along the upper part of his shaft and swirling around the curves of the tip. Heat pooled in her stomach as the taste of his skin filled her senses.

  “That’s…very good,” he panted, reluctantly pulling her away. If she continued to service him in such a way, their evening would be over far sooner than he would like.

  Chapter Six

  “Do you ever touch yourself here, Sara?” he asked as he swirled lazy little circles around her bundle of nerves. The very edge of his lip pulled up on one side, his grey eyes watching her half lidded with desire. “You may speak to answer me.”

  “I…” Sarah started to say no, of course she hadn’t. She had heard about her friends doing that, but had never really gotten up enough nerve to actually do it herself. But she didn’t want to let on to him exactly how prude she was.

  “Yes,” she said, her eyes shifting away from his as her cheeks warmed even further. It was such an obvious lie, and she knew he didn’t believe her, but at the moment she couldn’t muster anything better. The way his fingertips rubbed her in all the right places had her ready to climb the wall.

  “Really?” he said, his brow twitching upward. He knew she was bluffing and he intended to call her on it. “Show me.”

  Sara was snapped harshly back to reality, both by his command and the sudden cessation of his incredibly seasoned touch. She started to panic as he pulled away from her, his eyes roaming her body as he waited for her to comply. She hadn’t counted on him wanting something like that, and she really had no idea what to do.

  “I’m waiting,” he said, a little tilt in his neck as his eyes locked onto hers in a challenge.

  Her resolve hardened. She had come this far, she couldn’t turn back now. Besides, it was no big deal. It was her own body. Her hand trailed down her stomach, past the groomed mound of curls, searching for the spot that he had been massaging moments earlier. It didn’t take her long, and she soon found her nerve with the flood of pleasure that hit her when she did.

  He could see her struggling to keep herself standing as she began to pleasure herself for his watching enjoyment. She acted like a girl who had just dis
covered herself for the first time. She was perfect, and he hardened to a new level of desire for her. He lazily stroked himself while he watched her.

  The sight of him, touching himself while he watched her was more than she could handle. Her body felt so hot she was sure she would burst into flames at any moment. He was the most utterly masculine thing she had ever seen. The bulky, sinewy muscles of his arm shifted rhythmically as he pleasured himself, watching her do the same. The tingle that filled her body became stronger, and Sara had to stop. She just couldn’t take it anymore, her knees buckled, sending her toward the floor. Just before she hit, she felt strong arms wrapping around her. Her pleasure hazed eyes focused on his. There was a flash of concern for her in them, before the cocky smirk spread on his face once again.

  “Are you alright, Sara?” he said, as he helped lift her back up. She got her footing back and tried to step away from him, but his arms remained wrapped tightly around her. She could feel his manhood pressing insistently against her abdomen and it brought the blood rushing straight back into her cheeks.

  “I think you were enjoying yourself a bit too much,” he said, his eye twinkling with enjoyment. Sarah had never been more embarrassed in all her life. Here she was, trying to be professional, and trying to please this man that made her knees knock, and she had completely lost herself in her own pleasure, while he watched.

  “Sit,” he said, gesturing to the couch, “I think you will find it easier to pursue such pleasures.”

  If he wasn’t paying her as much as he was, Sara would have stormed out of the room a long time ago. If his presence wasn’t crushing enough just by being himself, he had to trick and tease her. She felt like a mouse being toyed with by a cat who was about to devour her. Sara bit back her urge to fume at him and sat back on the couch.

  He settled himself on the floor, kneeling before her. His hands came to rest on her knees, gently guiding them apart. She tried to resist, uncomfortable with such a vulnerable act, but he persisted. The sight of her, splayed so perfectly before him made him twitch with need. He rubbed absently at his ever-tensing crotch while he kissed a trail up her inner thigh.

  Sara was about to hyperventilate. The sound of her rapid pulse filled her ears, and she could do nothing but clamp her eyes and try to cope with the sudden onslaught of sensations that coursed through her. When his tongue snaked out, licking her ever so gently in that bundle of nerves she had to bite her lip to stop from crying out. A whimper escaped as he did it again and her hands tangled in his meticulously styled hair to keep herself planted on the couch. Her body tensed and blackness took over her. She rocked her hips as his lips kissed her, suckling skillfully in all the right places. His hands crawled up her body and grasped onto her breasts. He flicked lazily at one already perky nipple and smiled when he was rewarded with a little gasp.

  Her thighs shook around him, her eyes were clenched tight, and he knew she was close. His tongue swirled around most sensitive spot, ruthlessly breaking her down. It didn’t take long for him to push her over the edge. Her body trembled as she tried to contain the moan that bubbled up in her throat.

  “Sara,” he said, using his finger to continue rubbing her, bringing her gently down from her high. She continued to tremble, her breaths coming in gasps. “I believe you are enjoying this. Immensely.”

  Chapter Seven

  He gave Sara a moment to recover from her orgasm, pleased with himself at how quickly he brought her to completion. Her cheeks were stained red, her hair was disheveled and there was a light sheen of sweat covering her. He rose from between her legs, hovering over her as he appraised his work.

  “Come,” he said, gesturing for her to follow him as he made his way over to a door on the far side of the room. It took Sara a moment to catch her breath and make herself get up. Her legs were shaky and unstable, her whole body still tingling and pulsing. He opened the door and showed her into a small room with a single bed and not much else. It was windowless, only dimly lit with a single sconce on the far wall.

  He had never taken a girl into this room, but something about Sara was special. She was so good at this little fantasy of his that he found it easy to play right along with it.

  “Lay down,” he said as he clicked the door shut behind her.

  Sara sank into the feather-topped twin mattress, the soft cotton of the high thread count sheets cold against her naked and over stimulated flesh. The glow of a single candle flickered off the sheen of sweat that covered her. She tried to relax on the bed, waiting for him to come to her, fear but with a hint of excitement filling her. She felt oddly ready for this, though she was nervous she wouldn’t be pleasing to him.

  He could feel the tension that gripped her, but he knew there was nothing more he could do to relax her. He wedged a knee between her legs, positioning himself over her.

  He made her feel so small. He brushed her hair out of the way as he suckled and nipped at her neck, renewing the burn that had subsided. He caressed her cheek with one hand as he pulled back to look her in the eyes. His lips locked with hers for a brief moment before pain shot through her and he partially collapsed over her, his heavy breathing coordinating with every new rush of pain that went through her. She clenched her eyes shut, gritting her teeth and trying to make the ache go away. She felt so full, so stretched. She tried to move her hips into a more comfortable position, but the movement did nothing to stop the discomfort of being stretched so completely.

  He was struggling to hold on. He would hate to end things prematurely, but he couldn’t last much longer. He had never been brought to pleasure so quickly. She was so tight, so wet. Her walls quivered around him. He pulled back to see if she was enjoying it as much as he, but when he saw her face realization hit him. Her face was contorted in pain, and she was trying to hide it, trying to pretend she was enjoying it. This was her first time. He pulled away from her, but he couldn’t stop his body from releasing his pent up pleasure. His seed spilled across her lightly heaving stomach. He could see the small amount of blood on the sheets beneath her.

  “You are really a virgin?” he asked with a strained voice through heavy pants. He realized the harshness with which his words came out when she flinched and recoiled from him. The lust had cleared from his mind with the shock, but it only seemed to inflame the desire his body felt.

  “So,” Sara said defensively as she tried to collect herself. Her job was over and she didn’t need to play by his rules any more. “What does it matter to you? You got what you wanted, and so did I.”

  “What I wanted?” he said, his brows pulled together. “This is not…”

  “Look,” Sara said, her demeanor shifting so suddenly it surprised him. She pushed out from beneath him. “This is just business, O.K. I have my reasons for doing this.”

  “I just wish you would have told me,” he said.

  “Why?” Sara said, with a shrug. “Would it really have made such a difference? Besides, you told me not to talk, remember?”

  “It would have made a difference,” he said with a sigh. It would have made a big difference. He would never defile such innocence with such little care. He tried to reach out to her but she pulled away

  “Whatever,” Sara said, scooting off the bed. This situation was only getting more awkward. Now that her job was over, she found herself a lot more at ease. His presence was still overbearing, and she just wanted to get away from him. “Don’t feel all guilty or whatever. I knew exactly what this was. Just pay me.”

  “You can see your Madame for payment,” he said, his voice turning suddenly cold like a winter snap. He rose from the bed and stalked out of the small room, leaving the door open for Sara.

  “I trust you can see yourself out,” he said when she followed him out of the room, his back turned to her as he fixed himself another glass of whiskey. Sara was taken back by his sudden shift in demeanor, but she shrugged it off. The temperature in the room had dropped noticeably and she got the distinct impression that she had suddenly become of l
ittle concern to him. She redressed herself as quickly as possible and slipped out of the top floor office without another word to the man who had just made her into a woman.

  Chapter Eight

  “Why didn’t you tell me?” the client demanded as he narrowed his dark grey eyes down at the Madame.

  “I thought you would be pleased,” she said, taking a leisurely drawl from her hand rolled cigarette. She dealt with powerful, egotistical men all day, every day, and none of them threatened her. This one was no exception.

  “I pay your girls for a reason,” he spat, still trying unsuccessfully to intimidate the woman. “For a fantasy, and nothing more.”

  “Relax,” Madame Gwen said, waving him off with a perfectly manicured hand. “The girl came to me. I tried to talk her out of it, but she insisted. If it hadn’t been you it would have been someone else. I thought, given your preferences, that you would enjoy being her first.”

  “But why didn’t you tell me?” he said. His tone softened, but he still wasn’t ready to back down.

  “Because I figured you would act something like this,” she said with a smirk, “and you had the highest bid for the evening.”

  There was a reason Madame Gwen had such illustrious clientele, besides the fact that her girls were very talented at the services they provide. She offered more than just the typical calling service. She created an atmosphere, an allure, a secret society of sorts, were the male clientele competed with each other for the attentions of the girls. Everyone was bound to certain rules. Those with more power, had different rules. It created a hierarchy of the power hungry alpha males that filled her little pink book, all of them more than happy to pay her mind numbingly large amounts of cash for a night in the secret world she built for them.