Just a gigolo. (Closed)

[Niceandbrutal]

"Oh God! Oh God! Oh, Leon! Don't stop! Oh please, harder! Faster!"

Leon aka Wayne Olsson was on the home stretch with his client. A fortysomething wealthy businesswoman (one of his regulars) had wined and dined him at an exorbitant fee, then she had taken him to her penthouse and demanded her money's worth. She was clean and good looking, but she'd confided in him once and told him that she liked to be in charge of the where and the when of her dates and copulations, which suited Leon/Wayne just fine. Theirs was a professional relationship. He pretended to hang on to her every word as she babbled on about business and whatnot, and then she took him home to her house to be fucked by him.

Wayne Olsson had been blessed with good looks. He was 6'2" with piercing yet tender blue eyes and golden hair, a ready and charming smile revealing a set of perfect white teeth. He worked out regularly at the gym and twice a week he practiced the art of self defence called Krav Maga. The last came about after a scare with a jealous husband that tried to kill him. He was toned and fit, his body the result of good genes and deliberate sculpting. And now he made this successful businesswoman squeal and moan with pleasure.

He'd chased her through a few smaller orgasms, but she was nearing what he liked to call the dealbreaker, that last huge orgasm that exhausted his clients. True enough, she let out a primal scream as he sent her over the edge. Then she collapsed, spent. Thanks to the viagra Wayne was still hard, but that would subside. He cuddled her as she regained her senses. After a while she asked if he couldn't stay the night. Wayne declined, explaining that she'd paid for dinnerdate and sex, that sleepovers cost extra, and that he had another client early tomorrow morning. That effectively killed the mood and she curtly told him that he could find his way out on his own.

Wayne went home. He lived in a small flat in downtown New York City. He could afford it with his clientele, though the last few years he'd considered moving to a cheaper place so he could send more money back home. But he had to keep up appearances with his family. They were going through the worst time ever, what with his sister being hospitalized with leukemia. The treatment hadn't come cheap and his parents had almost bankrupted themselves to pay the bills. That was two years ago.

Now, at 26, Wayne had been selling himself for the last two years. His parents thought he was a successful stockbroker on Wall Street. Wayne had tried his hands at being a stockbroker after business school, but he hadn't the instincts or aggressiveness needed to succeed and he washed out, like so many other hopefuls before him. So in desperation he turned to that most ancient of professions, selling himself to others for their sexual pleasure. He'd always been a hit with girls and he thought getting paid for sex was a neat idea, naïve as he was. So he upped his standard of grooming, dressed sharp, worked out and placed an online ad.

Wayne had almost quit as he tried breaking into the sexmarket. After a while there were quite a few caveats in his online ad. Cleanliness a must. He'd retched once when a very unclean woman had demanded he go down on her. No men. No disabled. He'd been with a woman in a wheelchair that almost broke his heart. She'd texted and phoned him for weeks after their session, convinced he had feelings for her. He demanded discretion if the women were married, asking for the deletion of text messages, phone numbers, and removal of his ad from the browser history. And so on.

He went for a shower, then poured himself a herbal tea to help him go to sleep. He stayed away from drugs and drank moderately. He had to keep sharp. Wearing a luxurious bathrobe, he plopped down in the chair by his desk to check his mails. Two mails in particular caught his attention.

 

[Violet_]

Sherry-Lee stared at herself in the mirror. The 21 year old, dark haired girl with the blue eyes that stared back at her looked forlorn. Was there something wrong with her? She turned and peered across her shoulder at her ass in the mirror, giving it a disdained look.

It wasn’t like Sherry had never kissed a guy before, but that was exactly the problem, it never went any further than that. All her friends had done the deed years ago and yet, somehow, she got left behind. She felt like she was wearing a massive sign around her neck that said ‘look at the virgin, she can’t even find a guy to do it with’.

What Sherry didn’t know, was that she resembled a Grecian goddess. She came across as being worldly, confident and serene and the majority of men her age found it daunting to speak to her. They automatically assumed they had no chance of getting anywhere with her, which Sherry wrongly perceived as being rejected and isolated, to the point where she was absolutely desperate.

Slinging her bag across her shoulder, Sherry left her little bachelor flat just off campus and went for a coffee at her local Starbucks. She was contemplating her plan of action while she sipped her caramel salted mocha, when a conversation at the table behind her, caught her attention.

“He is absolutely professional and so discreet,” the one woman was saying to the other. “He is a sterling example of the perfect man candy and oh god, can he fuck.”
Sherry was all ears, she even momentarily forgot about her coffee. She never would have thought of it as an option if she wasn’t here at this exact moment. Maybe fate was trying to tell her something? If she couldn’t find anyone that was interested, then maybe she should pay someone to do the deed. It sounded dirty, scandalous even … but plausible.

I need a name, lady, Sherry thought, as she eavesdropped shamelessly.
“Leon is the best,” she piped up, as if on queue. She then proceeded to give her companion his e-mail address, which Sherry hastily scribbled on her paper napkin.

She took her mocha and walked out of Starbucks, staring at the napkin. Was she seriously considering this? It took Sherry a good portion of the afternoon to rake together the courage to sit down and start a mail and another eon agonising over how to word it, and what exactly to say. She didn’t want to blurt it out and then feel like a complete idiot, and besides, she wanted to give herself an opportunity to run for the hills if it all went pear-shaped while still saving face.

She read over the message, one last time.

Hi Leon
I received your details from a lady who spoke very highly of your abilities and I was wondering if we could arrange to meet? Also, can you give me an indication of your fee structure?
Will appreciate greatly
Sharon

Sherry bit her bottom lip pensively, every single word in the message had been changed at least three times. Throwing caution to the wind, she closed her eyes and clicked on the ‘send’ button.

It was done, now all she had to do was wait ... she nibbled on her bottom lip again.

 

[Niceandbrutal]

There were two mails with an almost equal wording, one from a 'Tracy' and another from a 'Sharon'. Someone had spread the good word about him, it seemed. That was good. Word of mouth was one of the best ways to advertise, cheap and efficient. He sent off a mail to the both of them with the same message:

Dear Sharon.

First off, please forgive my late reply. I see you are a new potential customer. New clients I insist on meeting before setting up a session. The first meeting between us is free of charge and we can, if we click, go on to a session as decided by you right after meeting. The session is not free of charge, however. I'd like to postpone discussions of fees until we meet. If you don't object, I'd like to set up a meeting tomorrow, 12 PM or later. You'll find my cellphone number in my ad, please call or text me for details. Looking forward to meet you!

Leon

He sent the same message with variations in names and time to Tracy and Sharon. He hoped Tracy would meet him as early as 8 AM. Judging by the time she'd sent off her mail she had time to spare in the morning. Tracy texted him back almost immediately, wanting to set up a meeting at 10 AM. He acknowledged. He waited for Sharon to text or call him, when his private phone rang.

It was his sister. Trying to hide the worry in his voice he talked to her like they did when they were younger and constantly arguing: "Hey creep! How's chemo treating ya?" His sister hated it when people tried being considerate and treated her delicately, and usually she'd giggle and retort in kind when he addressed her like that. Not tonight, though.

She sounded scared and little as she replied "lousy". Then she started weeping. For the next few minutes Wayne just sat and listened to her sobs as he tried to console her. She was in strict isolation after a fierce bout of chemotherapy, rendering her immune system out of order. She'd already talked to their parents for the best part of an hour, but their mom wept more copiously than she did and their dad's effort at bonhomie had crashed and burned as she told of her day at the hospital. So now it was patient big brother's turn.

He made up a story about his day as a stockbroker and how he'd earned 20.000 in one day. 15.000 of those would be winging their way to mom and dad's bank account tomorrow. She caught him off guard when she called him a cheap bastard. He stuttered and hemmed and hawed until she started giggling. "Gotcha!" Talking with him had clearly improved her mood. He was glad. Before they hung up he finished with his usual threat: "If you croak and break mom and dad's heart, I'll kill you! Get well, you little brat!"

His workphone had lit up when he had talked to his sister Wilma, a silent herald of a new message.

 

[Violet_]

Time slowly ticked by, each second hammering away painstakingly slow on the clock against the wall. What was the worst that could possibly happen? She asked herself. Leon could say no, and that would just be that. Sherry groaned and pushed herself up from her chair to pour a glass of juice.

It was a good two hours later before her inbox announced the arrival of a new message, and Sherry just about bolted out of the bathroom, her hair dripping wet and a towel haphazardly clutched together just under her chin. She read the message and then read it again. She wasn’t too sure how to react to it. Yes, she was elated that he replied, but in the same breath it scared her nearly to death.

Sitting down at her desk, Sherry thought long and hard about it. She had good reasons for considering it, but her subconscious was warring quite heavily with the idea. What if he was a mass murderer or an unstable serial killer? Was she brave enough to trust a complete stranger, or more pointedly, was she brave enough to go through with it?

Damnit Sherry, for once in your life, live a little, her subconscious scolded eagerly.
She expelled the breath she had been holding and picked up her phone, staring at the blank screen for a moment. Where would be a good place to meet? Starbucks was probably not a great idea. The two ladies that were discussing Leon may be there and that would just be entirely too awkward. She then decided on a small diner a little further up the street that was more secluded, but still had a good smattering of people around to serve as a safety net.

Sherry sent a text to Leon, to meet her there at 12:30. She had a gap in her schedule and that would work for her. “Look out for the girl wearing a hat,” she said as a way for him to find her, or alternatively it could serve as a way for Sherry to sneak away without being found. Regardless, it was done.

She barely slept that night, images of a faceless man doing delectable things to her kept haunting her dreams. Once morning broke, Sherry nearly went through her entire cupboard, trying to find something to wear that would suit the occasion. Something serious, or something summery, or something sexy, perhaps? With a frustrated groan, she pulled on her favourite pair of denims along with a comfortable strappy shirt. She combed her hair until it shined and then plonked a cute beret on top of that, which she slanted to the side.

That would just have to do.

It was a complete waste of a morning. Sherry could not concentrate on a single thing. Her mind was abuzz with thoughts of her impending rendezvous with Leon. When the time finally arrived, Sherry forced herself to walk to the diner at a calm pace, instead of running in the opposite direction. She owed it to herself to at least have a cup of coffee with the man. It wouldn’t kill her, and besides, you never know … it might just work.

Taking a seat, Sherry smiled politely at the waitress that appeared and told her that she was waiting for someone. The waitress left two menus on the table, before disappearing. Sherry nervously smoothed her fingers across the menus, staring out the window.

This was it.

 

[Niceandbrutal]

Wayne woke up early. He went through his morning grooming routine and emerged fresh and ready to meet two new potential customers. There was always an amount of trepidation when meeting new clients. He liked to size them up before agreeing to dates with them, preferably in a public place. He met Tracy at a Starbucks near the university, a bored wealthy divorcée who hadn't had any luck in nabbing a new man. She was easily satisfied and Wayne emerged from her apartment at 11:45 AM, $2.000 richer. What the hell. She could afford it.

He had 45 minutes to kill so he sat down on a bench near the diner he was supposed to meet his new client in. It was very seldom that Wayne got together with women his own age or younger. He caught himself watching the student body going to and fro, especially the female half. Although he missed going out with girls near his own age or younger, he hadn't the energy to pursue romance for romance's sake. He had to ply his trade to help his sister. Which reminded him...

He busied himself the next few minutes, transferring a large sum of money to his parents. He then texted his dad to tell him a new transfer had been made and to tell mom he loved her. As he looked up, an absolutely stunning young woman went past him. A black haired beauty with stunning blue eyes and an elegant and confident air about her, she must have the boys on campus eating out of her hand. A wistful sigh escaped him. No chance of ever getting a girl like that as a client.

She entered the diner he was supposed to meet Sharon in. Five minutes before he was supposed to meet her, he began assuming the role of quietly confident Leon that women seemed to adore. As he got up from the bench his private phone buzzed. It was Wilma. She'd gotten one of the nurses to snap a picture of her with the bouquet of balloons he'd sent for her. Before the illness, Wilma had been a gorgeous and bubbly young woman. Now she looked tired and emaciated, despite her smile. Wayne choked up but managed to keep it under control. He had a business meeting to attend to. He texted Wilma (You're a mess, you little creep. But I still love ya!) before entering the diner.

There sat the beautiful young woman he'd just admired. Ignore her. She was not his client. Wayne felt certain about that. He scanned the guests of the diner intently. A bunch of boys discussing a game of football. Three couples, lost in each other. Three sets of girls having lunch, discussing clothing, parties and the latest reality show. No single women wearing hats. Except... but that couldn't be!

He looked at the beautiful young woman again. She was fiddling with the menus and absentmindedly looking out the window. And she wore a beret, perched at a cute angle. He approached her cautiously. Yep, her body language betrayed her nervousness. He cleared his throat and with a calm voice said: "Sharon? I'm Leon."

 

[Violet_]

Sherry didn’t respond at first, Sharon was just a name she had thought up to conceal her identity. “Leon,” she nearly spluttered, a little surprised. She didn’t quite know what to expect, but this was certainly not it.

Leon was younger than she imagined. He was extremely tall with a head of golden hair and the bluest eyes she had ever seen. She just wanted to dive into them and get lost in there. He looked to be well toned and Sherry desperately tried not to gape, mentally telling herself to keep her mouth closed.

“I’m She-Sharon,” she said hastily, not too sure whether she should shake his hand or hug him or what. She haphazardly came to her feet and offered him a hand in greeting, smiling a little star struck at him. “Nice to meet you,” she said as she sat back down again, staring at the menus and fidgeting with her hands in her lap.

“I would love a cup of coffee, would you?” Sherry asked, trying to break the ice, again not too sure what the protocol was. She groaned at herself inwardly, God, you’re such an amateur. Sherry waved at the waitress who came over and took their order, paying acute attention to every word Leon spoke.

Sherry didn’t quite know how to broach the topic, so she avoided it like the plague. “Lovely weather we are having?” she asked, looking up at him and smiling brightly. In that instant she wished she was more experienced or at least a little more comfortable around men, he must think she’s a blundering idiot.

Their drinks arrived and Sherry used the opportunity to hide behind her mug, if that was at all possible. What exactly was she going to do with the mug, throw it at him if he made a move? She smiled to herself, trying to imagine the scene. “Sorry, I’m a little nervous,” she confessed, looking straight into those glorious blue eyes. It felt as if he could see into the deepest, darkest part of her soul, which didn’t help at all.

“How does this work?” she asked curiously. “Do you come to my place?” as soon as she asked the question, she frowned. Did she want to take a complete stranger to her place? What if he turned out to be a weird stalker dude? Sherry tilted her head to the side and regarded him thoughtfully for a moment, no, he wasn’t weird and if he turned out to be a stalker, she might just like it. There was something about him…

Once he explained everything, Sherry went quiet, contemplating it. This was her last chance to back out. Leon seemed like a genuinely nice guy, he was certainly very easy on the eye. She had nothing to lose, besides the one thing that branded her a complete failure to womankind. She had not told him that she’s a virgin, she would deal with that humiliation later.

“Okay,” she said, making up her mind. Feeling braver than she was, Sherry stood and offered her hand to Leon. “Let’s do this,” she said softly, smiling at him sheepishly.

 

[Niceandbrutal]

Wayne was shocked beyond belief that a beauty like her would resort to renting him. She had a beautiful body and a face that most girls he knew would kill to have, beautiful black hair and clear blue eyes that made him break character inwardly for just a little moment. There was an uncertainty and shyness in them that made him feel tender towards her, an emotion he hadn't felt since forever. She slipped when she told him her name, confirming that she too preferred to keep an alias around him. Fair enough. She couldn't know if he was a blackmailer or serial killer or would-be stalker. She had to be used to obsessive behaviour from men. Maybe that was it? She just wanted to get laid without any hassle, and this was the first time she did this with a professional. She certainly seemed nervous enough.

Wayne put on the character of Leon again and smiled at her as she stood to shake his hand. He grasped it and shook, enjoying her soft young skin touching his. As they sat down she engaged in small talk, obviously nervous about talking about why they met. Wayne went along with the pleasantries but found it hard to maintain the character of Leon. He found he wanted to get to know her, as a person. She was cute in her awkwardness and ridiculously beautiful.

As their coffee arrived, Wayne used the time they drank to assess the situation he was in. These were dangerous waters he was fishing in. He could very easily fall for this young woman. Although they hadn't spoken for long, her body language told him volumes about her. Apart from being nervous she was downright clumsy when she talked with him. He started to have a suspicion that she wasn't used to be with men at all. Maybe she was shy? Maybe she'd been sheltered? Maybe men around her were too intimidated by her beauty to make a move?

Then she asked him: “How does this work? Do you come to my place?” He set his cup down and looked her in the eyes. "My place or yours, that is up to you, Sharon. Now, I operate with prices based on what you want from me." He'd already decided that she would get his cheapest rates. "I start at 100 dollars for one hour of sex, 150 dollars for two. If you want the date experience it'll set you back 300, and then you'll have to pay for any entertainment in addition. Date and sleepover will cost you 500. Any kinks or weird requests cost extra, I don't do any toilet games or anal. Other than that, the sky's the limit. If I may be so bold, I'd suggest a sensual massage before we, ah, get down to business." Wayne found that a massage often helped nervous clients relax before they copulated.

Wayne positively hated talking about prices with her. For the first time since he'd started in this business he'd enjoyed just talking and hanging with a client. But business was business, he supposed. She'd grown quiet, clearly contemplating her options. At last she had made up her mind. "Okay. Let's do this." she said as she stood up and reached for his hand. He stood up and took her hand in his, suddenly not wanting to let go of her. She was indeed trouble, but something about her compelled him to go through with it.

As they left the diner he asked a few questions of his own. "Should we go to my place or yours? I have a small flat near Central Park if you don't feel like bringing me home to your place. Also, I need to know for how long you want me and what you wish of me."

He also wanted to ask her what a stunning young woman like herself was doing renting a guy like him, but he kept his mouth shut. He realised that he was walking down the street and holding hands with a client. He liked the feeling.

 

[Violet_]

“Should we go to my place or yours?” He asked
Sherry thought about it for a moment and then started steering him towards her place, “my place,” she said in answer. She knew she initially didn’t want to take him there, but she would feel more comfortable and more at home there. This was a big thing for her and she didn’t want to ruin it by not knowing where the bathroom is.

“I need to know for how long you want me and what you wish of me,” he asked.
She had no idea what she wanted, well besides the obvious, and she didn’t want to sound like a blundering fool, so she just avoided answering him directly. “Let’s see how it goes,” she simply said.

Sherry enjoyed walking hand in hand with him. Somehow it felt like they ‘fit’. She carefully avoided asking him about what he does. To be honest, she didn’t want to think about it right now. So they landed up talking about what their favourite coffees were, places they had been and all sorts of odd ends.

She was quite surprised at how comfortable it felt. Sherry had initially intended their interlude to be a once-off event, but now she found herself hoping that she would see Leon again. Sherry wasn't even sure if that was possible, it was not as if they were an item, were they? She regarded him pensively from under her lashes. Her conscience was warring heavily with the idea of starting a relationship with a man who sold his body for money.

When they finally reached her apartment door, Sherry unlocked it and invited him in with a nervous smile. Just walking and talking with him was great, but this was different. She could feel the tension escalating. “I … uhm, welcome,” she said haltingly, good manners overriding her apprehension. “Would you like something to drink?” she asked quickly, before she ducked into her little open plan kitchen, leaving him standing in the door. She was wistfully wondering if it wasn’t too early for something a little stronger, this was more nerve-wrecking than she had anticipated.

That ‘oh so naughty’ feeling washed over her again. This has got to be one of the most outrageous things she’s ever done. She poured them both something to drink and then nervously stood, wringing her hands. She needed to tell him and she needed to do it now, to give him the opportunity to run for the hills… or for that matter, give her the opportunity to chicken out.

“Leon,” she started, looking everywhere but at him. “I need to tell you something,” she said. Her throat had gone all dry and she nervously lifted the glass, realising for the first time that she was trembling. She placed the glass back down and grasped her hands together, hoping he hadn’t seen that.

“I’m a virgin,” she said very quickly, her entire face went scarlet. She was holding her breath, trying to gauge his reaction. She hoped he would stay…

 

[Niceandbrutal]

Walking hand in hand with 'Sharon' and talking about day-to-day stuff was a rare treat for Wayne. She seemed a bright and cheerful girl, her nervousness notwithstanding. With the low prices he'd offered her he hoped she would be a regular. Hell, he was entertaining the notion of dating her. But that could lead to awkward situations, what with his line of work. If he stopped doing what he did it was goodbye Wilma for sure. Unless he won the lottery, but what were the chances of that? He pushed these grim thoughts out of his mind, enjoying the moment of pretend.

She lived in a dorm, confirming Wayne's suspicion of her being a student. Not that he minded, of course. He found himself growing enamoured of her, nervous mannerisms and all. As she let him in he looked around at her student apartment, finding no real surprises. Her nervousness seemed to mount as they entered the flat. She was fiddling with glasses and shaking. And then she blushed deeply as she told him her secret.

Wayne was so shocked that his mouth fell open. He quickly regained his composure. A wave of pity washed over him as he put two and two together. Unaware of her almost intimidating beauty she'd come to the conclusion that no man was interested in her because no-one had dared to ask her for a date. He couldn't help himself. He walked up to her and cupped her cheek, lifting her head to meet his eyes. "You really don't know how beautiful you are, do you? You mistake all the boys' shyness and intimidation for rejection. And so you turn to me to get it over with. It really is a shame." He hugged her, inhaling her smell as he did so. She smelled young and fresh and her body was taut and soft against his. His penis started stirring on its own as he became genuinely aroused by her.

He ignored the stirrings in his pants and looked at her, holding her at arms length. "Don't get me wrong, I'm flattered you chose me for your deflowering and I will be gentle with you if you choose to go through with this. But are you sure this is what you want? A pretty woman like you should have her pick of boyfriend, not resort to pay a professional sex-worker like myself. I will be honored if you say yes and I will not hold it against you if you say no."

This was totally unprecedented. Wayne never saw this coming. He waited anxiously for her reply.

 

[Violet_]

Sherry watched as his expression changed, softened, and the next moment he crossed what little space there was between them and tenderly took her face in his hands, forcing her to look at him. "You really don't know how beautiful you are, do you? You mistake all the boys' shyness and intimidation for rejection. And so you turn to me to get it over with. It really is a shame."

Sherry blinked at him in utter surprise. That was not the reaction she had anticipated, at worst she thought he would laugh at her, or make fun, but never this. She swallowed the lump in her throat as he hugged her to him. Gooseflesh erupted all over her skin. No man has ever done this before and once her mind caught up with what he just said, she blushed again. He thought she was beautiful?

He felt warm, almost comforting against her and Sherry tentatively wrapped her arms around him, enjoying the moment. All too soon, Leon pushed her slightly away and held her at arm’s length, those probing azure eyes staring deep into her soul again. Sherry was surprised at the sudden feeling of loss she felt, she wanted his arms around her.

"Don't get me wrong, I'm flattered you chose me for your deflowering and I will be gentle with you if you choose to go through with this. But are you sure this is what you want? A pretty woman like you should have her pick of boyfriend, not resort to pay a professional sex-worker like myself. I will be honored if you say yes and I will not hold it against you if you say no."

He was giving her a choice and Sherry dropped her gaze to the floor as she contemplated the situation. She had to remind herself why she was doing this, why she had contacted Leon in the first place. She had thought it would be allot more clinical than this, but she was pleasantly surprised. The thought of doing the deed with Leon, was not unappealing at all, the man was gorgeous, plus there was something more to him…

Sherry lifted her head, determination flickering in her eyes. “Leon, I am doing this because it is something that has been hanging over my head for a long time. I hear what you are saying, though I don’t quite believe you, you must understand that it has not been that easy for me. I want to know what it feels like to be taken by a man,” she said, tentatively lifting her hand and smoothing it across his chest, her cheeks staining slightly. “I have no idea how to touch a man, let alone please one, but I am hoping that you will show me?” she asked in a small voice.

“-and, call me Sherry,” she added, smiling sheepishly at him.

 

[Niceandbrutal]

"Okay Sherry. We do this your way. But belive me when I say you can have your pick of almost any man you set your sights on. But if you're set on this I will not deny you."

He loved her touch on his chest. Her touching him filled him with a warmth he'd never experienced with another client.

"I already like the way you touch me, Sherry. It's nice. Soft but firm, don't change that." He cupped her face and looked into her beautiful eyes. It really is a shame he thought. He was sure she'd been picked on by other girls, jealous of her natural beauty. She seemed almost painfully eager to lose her virginity, and Wayne resolved there and then to give her the best experience he could provide. She... moved him in a way that was at once disturbing and wonderful.

He hugged her again and slowly started stroking her body. His hand slid gently down her back and down her sides, then up again, lightly caressing her buttocks. Then he did something he'd never done before with a client. He grasped her neck gently and gave her a tentative kiss on the mouth. All the time he watched her carefully to gauge her reactions to what he was doing.

 

[Violet_]

As Leon took Sherry's face in his hands, she stared into his glorious blue eyes and in that instant she wished she could read his mind. His gaze was so intense, it made her feel like she was the only living, breathing person in the world.

It made her ridiculously happy that he liked the way she touched him and when he enveloped her once more in his arms, Sherry replicated her first attempt, gently running her fingers up and down his spine.

His own hands did the same and Sherry expelled a shuddering breath, god it felt so nice. She closed her eyes and nuzzled closer against his chest letting her body, her senses, feel his movements, his touch. It was intoxicating. His hands were smoothing across her derriere before she felt his hand at the back of her neck, gently holding her. The next moment his lips touched hers and Sherry could feel her body come to life.

Her eyes fluttered open and she stared into Leon's beautiful blue eyes, drowning in their depths. Sherry's eyes were almost black, dilated, something she's never felt before kindling deep in her depths.

This man would be her undoing, that Sherry knew with crystal clarity.

She moaned against his lips and slowly moved her hands up his chest, almost awkwardly wrapping them around his neck and then she kissed him back. Sherry at least knew how to do that, and in that moment it was all she wanted, Leon's lips on hers, his hands all over her body, the heat of him against her. Butterflies were fluttering around excitedly in her tummy. Sherry's senses were drugged with the electricity that seemed to crackle between them.

 

[Niceandbrutal]

As soon as she kissed him back, Wayne knew she was trouble, that this whole situation was trouble. He felt his stomach, his head, and his lips tingle as their kiss deepened. Her response was so genuine and fresh that he slipped entirely out of his armor that was Leon. After a while they broke the kiss to get some air. They were both flushed and short of breath. Wayne looked at her, lost for words. He stammered: "That was... um... wow!"

He started taking off his jacket. He did not striptease and he did not just take it off perfunctorily. He just slowly slid it off, never breaking eye contact with her. Then he slowly took off her beret and started unbuttoning her denims. He then took off his own shirt, revealing a sculpted torso. He suddenly started feeling bashful. He was battling with himself now, the professional Leon fighting with the infatuated Wayne. They were both intent on giving her pleasure, but Leon wanted to keep a professional distance while Wayne wanted to make love with and snuggle up to this young woman.

He slipped his pants off and stood before her clad only in silky boxers and socks. She was dressed in her underwear. She had a beautiful body and he felt himself growing ever harder as he took in the sight of her. He hugged her again, relishing the feel of her soft and warm skin on his. He gave her a new lingering kiss before asking her: "Could I tempt you with a massage, Sherry?"

He tried to be professional, but his voice revealed his infatuation.

 

[Violet_]

"That was... um... wow!"

Sherry simply nodded in response, unable to find her voice and unable to tear her eyes from him. He kept her gaze captive as he slid his jacket off his shoulders and then he reached up and took the beret from her head. Just that movement, brought him closer once more and Sherry breathed in the scent of him before he wordlessly dropped his hands to her waist, his fingers deftly undoing the button on her denims.

Sherry’s breath caught in her throat, Leon still holding her gaze. He proceeded to take his shirt off and she bit down on her bottom lip, stealing a glance at the glorious male torso before her. Sherry’s cheeks coloured. She wanted to run her fingers across it, but she wasn’t sure if that was okay.

She quickly realised it was a tag game, and a shy little smile touched her lips as she took her shirt and lifted her arms, pulling it from her chest and letting it fall next to her on the floor.

Leon’s pants fell to the floor and Sherry swallowed reflexively. She once again let her eyes drop very quickly, almost feeling like a naughty child, for sneaking a peak. God, he was sexy and this time Sherry blushed bright pink.

She undid her zipper and let her denims join his pants on the floor. She felt exposed and she had to fight the urge to wrap her arms around herself. Sherry was very relieved that she had dressed in some of her best underwear, black lace hugging her chest like a jealous lover, echoed in the panties she wore. Leon on the other hand looked cute in his boxers and socks. She wanted to dip her thumbs into the elastic and flick him, a naughty little smile tugging at her lips.

Wordlessly, Leon took her in his arms again and Sherry let out a deep and shuddering breath, the feel of his skin against her made her feel warm. His lips found hers again and Sherry lost herself in it. He released her lips from his onslaught on her senses and asked her in a voice that made Sherry’s heart flutter, "Could I tempt you with a massage, Sherry?"

She nodded, before the naughty little smile tugged at her lips again. She couldn’t help herself. She quickly dipped her thumbs in his boxers and flicked him. “I’ve always wanted to do that,” she confessed.

 

[Niceandbrutal]

Wayne could not help but laugh at her playful toying with his boxers. He loved the impish little smile that graced her face. She was playful and shy at the same time, something Wayne found refreshing and endearing. He had a bottle of baby oil with him, just in case. He asked for a large towel and commanded her to lie on top of it on her bed. He gave her an easy out, asking her to remove her underwear only after she was lying face down. He helped her with her panties, sliding them down her graceful legs. He undid the clasp on her bra and helped her off with that as well. He then undressed completely, not looking to see if she was watching him. She was selfconscious enough as it was, and if she wanted to look she could do so without him knowing. He didn't mind.

He turned around after undressing. He wasn't sure, but he thought he heard her move as he turned. He took the bottle of baby oil and sat beside her on his knees in her bed, his thighs in contact with her abdomen and hips as she lay face down.

"Just relax and let things unfold, Sherry. If I ever make you uncomfortable, tell me so. There is no shame in asking for what you want. If you'd like to touch me, please feel free to do so, but respect it if I say 'no', please."

As he talked, he admired her body. It was young and firm, unblemished and smooth. Wayne felt another twitch in his member. No need for Viagra or cockrings here, that was for certain. He smiled wryly. He'd never had the guts to approach a girl like her if things had been different. And here he was getting paid to take her maidenhead. Life was strange.

He poured a thin line of oil on her back, eliciting a little gasp from her as the cold oil hit her. He started kneading her shoulders firmly, making her moan with pleasure and a little pain. He eased up, gently manipulating the muscles and tendons in her neck and shoulder. "Relax" he whispered. He distributed the oil evenly over her back and set to work on the shoulder blades, manipulating them and rubbing them. He slowly worked his way down along the spine, spreading his hands outwards to cover the whole of her back. As he reached the small of her back he straddled her, making sure not to put too much weight on her. He let his fingers circle the dimples right above her buttocks before he started kneading the muscles there.

He was aware that his cock reacted very... favourably with the contact he had with her. It lay between her legs, throbbing a cadence of lust. He poured some oil in his hands and set to work on her thighs and calves. He moved down and gently massaged her feet, lifting them up and strategically placing them a bit apart in the process. He edged his knees in between her feet and started stroking upwards again. He slowly moved upwards, nudging her legs further and further apart until his knees were above hers and he had free access to her private parts.

 

[Violet_]

Leon asked for a towel and Sherry walked off to the bathroom, very aware of her current state of undress. She first debated over which towel to bring and finally brought him her beach towel. It was nice and big, fluffy and contained a multitude of colours that were sunny and happy.

Spreading the towel across the bed, she laid down on top of it as he asked and Leon wordlessly helped relieving Sherry of her underwear. Having sex, generally requires a distinct lack of clothes, her subconscious chided. Sherry acquiesced and felt the gooseflesh slowly spread across her skin as Leon’s experienced hands helped her out of the remainder of her clothes.

He disappeared and Sherry stole a glance across her shoulder, just in time to see his boxers slide to the floor. A gloriously naked derriere met her gaze and Sherry felt hot all over. This man was unreal, every inch of him was gorgeous. She stared unabashedly until he made a move to turn around and then Sherry dropped back down on the towel, looking the other way, a guilty expression lingering in her eyes. Sherry could feel the bed move as he sat down next to her, his knee touching her side … just.

"Just relax and let things unfold, Sherry. If I ever make you uncomfortable, tell me so. There is no shame in asking for what you want. If you'd like to touch me, please feel free to do so, but respect it if I say 'no', please."

“Okay, thank you,” she said softly as he put her mind at ease. It was good to know.

A gasp escaped her lips as he poured something cold on her back, without warning. The next moment Leon’s hands were on her, smoothing across her skin, working the muscles in her shoulders. It was heavenly and Sherry moaned in appreciation. He found knots she didn’t even know she had and worked his magic on them.

"Relax" he whispered in that beautiful voice of his and Sherry made a concerted effort to do so. Taking a deep breath, she tried to expel all the tension that had been building as Leon steadily worked his way across her shoulder blades and down her spine. He straddled her, which made Sherry tense for a moment, wondering if this was it … and then his practiced fingers continued their onslaught on the small of her back, which made her relax.

Sherry was however painfully aware of his arousal that was resting against her and she bit down on her bottom lip. Something small inside her, made her proud that she could do that to him and she was a little relieved that he felt it too. Even though Leon was masterfully extracting the strain from her body, her insides were ablaze with … what was that feeling? Desire? It was as if Sherry’s body was ‘in’ on some big secret that she knew nothing about, wanting something she could only imagine.

Leon’s hands drifted ever lower, smoothing across her thighs, her legs, Sherry’s calves and finally her feet. He spent a bit of time lifting and working them before he placed them back down, apart, on the towel. He languidly made his way back up her legs, leaving Sherry wrapped in a haze of comfort, her senses lulled and her body enjoying the touch of his hands.

 

[Niceandbrutal]

Wayne now slowly started working the insides of her thigh, working his way up towards her privates. He slowly inched his way up, relishing the silky softness of her tender skin approaching her crotch. As he reached her tenderest parts he made sure to massage well outside her labial lips. He wanted her to gradually get used to him touching her and, hopefully, be slowly aroused by his ministrations. He placed his hands right under her buttcheeks and used his thumbs to slowly massage the area between the inner thighs and the labial lips. He kept this up until she started squirming or moaning, preferably both.

When she did: "Turn around now, Shelly." Watching her turn around was a sensuous pleasure as she gracefully yet shyly showed her body to him. He grew even fonder of her then. She was determined to lose her virginity with him, yet she was shy about it? What wasn't there to love about that little paradox?

He placed himself by her feet and started working his way up her shins and thighs again. As he reached her sensitive parts he lingered and massaged and kneaded around her labia and clitoris without actually touching those sensitive parts. Then he leaned down and planted a slow kiss on the mons venus before sliding his hands up her tummy. He sat astride her again, his manhood now fully erect.

He had now come to her breasts and he gave them full attention. He started on her lower ribcage, slowly spreading his hands outwards before swinging back in to gently grasp and knead her breasts. He leaned down and in turn licked and sucked on both her nipples. He was getting eager now.

He repositioned himself between her legs and slowly started to stroke her vaginal lips and gently flick at her clitoris. He needed to be extra careful now. He watched her intently, willing her with his mind to accept and surrender to his caresses.