The Consolation Prize

IC: Cassandra Delacourt

Cassandra was an erotica writer-correction: a best-selling erotica writer. No, it hadn't been her first job involving sex, nor had it been her second or third, but it paid for this homey little house deep in suburbia. She had moved in for about a year now. It was a renovated cape cod built all the way back in the fifties. It had all the amenities she desired plus as a bonus a fully decked out pool and deck.

She lounged back at poolside now in an appropriate swimsuit trying to regain a level of Zen to tackle that elusive scene in chapter eleven again. She hated that in all the English language there was no good synonym for the word "thrust". It was the bane of erotica writers everywhere, and the current starting point for her writer's block.

Cassandra was left frustrated and bored overall now.

Next door she heard her neighbors huge RV start and drive off. She saw the top of the head of their young son heading into the backyard.

In the few months she'd lived in this house she'd learned much about the young man. He was a highschool graduate. She remembered the graduation party last month and the kiddo's eighteenth birthday party the month before. Correction: she remembered the loud rock music interfering with her writing during those parties.

She also knew he was a bit enamored with his hot new neighbor. Cassandra had felt his gaze on him through the windows a number of times.

Her lips quirked as a very wicked but fun idea came to her mind.

The picket fence between her backyard and her neighbors had a hole in one of the boards. It would be at a perfect angle to get a look right at her lying back in her deckchair beside her pool. If he wanted to peep at her, and he certainly would want to peep at her...she may just give him something to peep at.

Her quirked lips turned into devious smirk. Boredom plus frustration always equaled mischief when it came to Cass.

She began to hum lightly to herself as if she was oblivious to the young man's eyes watching her through the hole in the fence as her fingers slipped beneath her suit to play with a nipple. The other hand lowered trace the part of the suit over her pussy.

Her smile widened. Cassandra Delacourt you're a bad bad bad girl. She moaned as thumb and index finger pinched her nipple and panted dramatically as the index finger as the other index finger circled over her clitoris through the fabric of her bathing suit.

"Congratulations on graduating," She said turning her head to look him in the eye as she continued masturbating herself for his viewing pleasure, "You know you can get a better show from that seat over there." She batted her eyes towards the deck lounger beside her.

"Don't worry. I don't mind," She continued as her finger snuck underneath her thong to really strum at her clitty, "In fact, would you like to play a game with me?"

At his question her devious smile deepened. "Why the best kind of game, but I call the shots. You have to agree that I make the rules, I decide if you win or lose, and what your reward for winning or your penalty for losing will be...can you agree to all that?"

Jason Hodges watched the RV pull away and gave a last wave as it sailed down the street with all the dignity of a beached whale. It could be useful but it sure was ugly and a pain otherwise. Still it wasn't all bad. It meant his parents could take their six week tour of the West, which they badly needed, and that he could have that same time with the house all to himself which was awesome. Outside of a few reminders that he thought his folks felt were just tradition they'd shown little hesitance at leaving him alone. He was eighteen now, only by a few months but it counted. And he wouldn't do anything bad. He was a good kid.

The worst part was they were probably right. He was a good kid and nothing probably would happen.

Jason was a geek and a nerd; he studied and got good grades, he played video games, even played a few table top role playing games. He had been a literal Boy Scout until turning 18. No one was beating down his door to host a party. He was in good shape due to being blessed with good genes that resulted in a mad metabolism and because he did like to walk and hike. He was far from popular but wasn't edgy in any way so as to attract that crowd. His friends were also all gone on their own vacations; the last big family trip before college changed everything.

He could invite a bunch of people over but they weren't and wouldn't be his friends. They'd just use it as an excuse to drink and screw and trash his parents' place. He probably wouldn't even get anything if he did.

So. He was a good kid. Nothing would happen.

But he did feel like a good kid. All kids looked at porn and smut online but he felt he did so a lot. He didn't just look at pictures or watch movies, he read stories and even did dirty chats. He read "how tos" in forums. He fantasized about dirty and deviant acts that his religious parents would find terrible. That he knew were sins but that he still wanted.

He turned away from the driveway and walked down along the fence line towards the back yard. His desires, his lusts, had all gotten worse since their new neighbor moved in. Cassandra Delacourt was beautiful and had the body of a goddess. There was a feeling about her. An open sensuality that made him feel drawn to her but also a little afraid of her. He'd spied on her in her backyard when she swam it just relaxed on the deck. It had been accidental at first. But now he would frequently check for her from his bedroom window or through the hole in the fence in the hopes if getting to admire her perfect form. He felt guilty about it. Dirty. But that also made it more taboo and even sexier. He had thought that she might have noticed him a few times...but she hadn't raised hell or told his parents so she must not have.

He got to the plank that had the hole in it and peered through. God damn, and there she was. "So fucking hot," he muttered. That bathing suit was sinfully cut and on her lush body it was a thing of scorching beauty. He felt his cock stirring in his shorts and he reached down to rub it through his clothes, just a little.

Those lips that he had imagined wrapped around his cock twisted into a smirk that sent a shiver down his spine. His eyes went wide as the most recurring star of his fantasies started touching herself. He was able to keep from speaking, thankfully, his breath quickening as he watched her toying with one breast under the suit and rubbing her pussy through it. It was a dream turned real.

It became a nightmare when she spoke and then turned her head. Their eyes met and it was as though a bolt of lightning had struck him. He flinched away from the fence, his face going pale and then blushing bright red. She knew! Shit! But she wasn't freaking out but...inviting him over? He shuddered as her finger dipped under her suit and he muffled a groan. Her question was a trap, just to get him to admit he was there but, but he could resist answering. "Wh-what kind of game?"

Her answer was even more of a trap. It was putting all the cards in her hand. And it was a trick, it had to be. She was teasing him. He should decline, apologize, and then avoid her for the next six weeks. That's what he should do. The smart thing. What a good kid would do.

Fuck being a good kid.

Jason took a few breath. "I...like games. I agree. I uh, I'm going to come over and we can get into, into specifics." Holy shit. He turned and walked back up the line of the fence. His heart was pounding in his chest so hard he thought it might crack his ribs. His palms were sweaty. His mouth was almost painfully dry.

He walked into her yard and each step felt like he was walking to his doom. This was a mistake. It'd all go wrong. She was going to call the cops or something. Jason came around the back, "Hey, Miss Delancourt." God that was lame. He was on the tall side of average at six feet in height and had a lean but strong frame. His eyes were nervous, a pale shade of green, and he nervously licked lips that were full and plush for a boy. His features were clear and defined without being either fine or hard. His hair was a tousled sandy blond that fell down past his ears but not quite to his jawline. He wore a t-shirt with the original Avengers on it and a pair of blue shorts that did little to hide the erection that had refused to subside. His feet were bare and his toes wiggled as a reflection of his nerves. "What game did you have in mind?"

IC: Cassandra Delacourt

"In fact, would you like to play a game with me?"

"Wh-what kind of game," Came his uncertain response.

At his question her devious smile deepened. "Why the best kind of game, but I call the shots. You have to agree that I make the rules, I decide if you win or lose, and what your reward for winning or your penalty for losing will be...can you agree to all that?"

It took him a moment, and Cassandra thought she might just lose him. That would be frustrating. She was getting excited about playing with this young man, and would be fairly disappointed if she didn't get to play at all now. The wicked smile on her face was starting to fade back as the seconds ticked before he finally answered.

"I...like games. I agree," He said and her devious grin surged back into existence.

"Talking through that fence will get rather annoying, don't you think," She told him, "And it would be easier to play this game if you were over here?"

"I uh, I'm going to come over and we can get into," He said the uncertainty returning to his voice, "Into specifics."

"You do that," She said and Cassandra saw the top of his wind-blown sandy blond head return above the picketed fence and start heading to the front yard. It was only a minute before he was walking into her back yard and stepped up onto the deck.

"Hey, Miss Delacourt." He told her nervously that made her chuckle. Poor kid. If her were anymore nervous he'd piss his own pants.

Maybe it would be fun to play with that? Although she was getting pretty horny for cock and making him nervous might diminish his performance in giving her the kind of fun she was looking for right now.

"Jason right," She asked before telling him to; "Just relax. You'll have more fun that way."

"What game did you have in mind?"

"A simple game for right now," She told him, "I don't think you can handle anything too complicated just yet."

She pulled her hand and gestured towards the seat beside her. "First, take a seat."

When he did she told him, "Let's get started," She held up three fingers for him. "I am thinking of a number between one and three...."

When he chose two-since it was the only number between one and three unless she wanted to make it difficult for him-which she didn't-not yet at least-Cassandra trailed those three fingers over the fabric of her swimsuit stretched over her right breast.

"Correct," She said and pushed the fabric aside freeing the breast to the air and to his gaze. Her hand roamed over the soft skin fingers playing over the nipple.

Her other hand lifted into the air all the fingers out and wiggled to get his attention. "I am thinking of a number between one and five."

He gave his guess.

She smiled to him. "Correct."

It hadn't mattered what number he chose. Cassandra hadn't even bothered to select one. No matter what number Jason chose she would have told him it was the right one.

Her other hand pulled the other breast free. Her suit now squeezed and pushed her breasts up and out, perfect to capture a young man's total attention. Smiling devilishly she arched her back off the back of the deck chair. Then both of them roamed caressing the slopes and contours of them before his eyes. Fingers circled around, pinched and pulled her breasts up until it hurt. She bit her bottom lip from the sting then let them snap back.

"Would you like to touch them, Jason," She asked as her hands lifted and raised them ever tighter together as if offering them to him, "You can, if you correctly guess this one...I am thinking of a number between one and ten?"

Jason took his seat at her instruction; his jade green eyes riveted to the swimsuit clad woman. His nerves hadn't gone away and he wasn't able to really relax but the sensuality of Cassandra and the sensuality of the situation allowed his teen mind and hormones to shunt his anxieties to the back of his mind for now. Even then a part of him still couldn't believe this was happening and was sure this was all a trick or a dream. This...this just didn't happen. Did it?

Her first question was a trick; he'd read enough books and stories with riddles to see the answer. "Two, of course." Then her fingers dipped and pulled her bathing suit further open; her plush tit freed, jiggling just a little from the motion. "Oh, hot...damn." His cock twitched and throbbed in his shorts; surging back to full hardness having softened halfway on his walk over while he could think about the potential consequences. Her breast was just...he didn't know the word. Perfect? Amazing? God, he loved seeing it.

She caught his attention with the hand wiggle and he blinked, swallowing, "Uh, right." Three, that was the magic number, right? Too easy. "Four?" Her smile rewarded him as much as her words and then she pulled the other side of the suit back and both of her magnificent breasts were free and bare. "Oh, my God, Miss Delacourt," he breathed. "They look so good, great."

It wasn't like he hadn't seen breasts before in porn or hentai pics but this was different. These were real and right in front of him; pert, plush, rounded, smooth temptation. She began to play with them and a visible shiver went through him. A soft groan escaped his lips. God, he wanted to touch himself. And her. His hands flexed but stayed on the edge of the lounger, gripping it tightly. He watched how she toyed with them; caressing and then pinching and pulling her nipples. It looked like it must hurt but the expression on her face was one of delight.

When she lifted them together, he couldn't help but lean forward to be closer to them. Her question drew half of a shaky laugh from him, "Of course, I do." Number guessing again, between one and ten. Lots of ways to go wrong. God, he wanted to touch them so bad! Jason licked his lips, trying to think clearly but unable to focus on anything except the lush temptation of his neighbor. "Seven, no. Nine. Though they're tens, wow."

IC: Cassandra Delacourt

"Would you like to touch them, Jason," She asked as her hands lifted and raised them ever tighter together as if offering them to him, "You can, if you correctly guess this one...I am thinking of a number between one and ten?"

"Of course, I do," Came his answer to her question. His eyes were glued to her bared breasts.

His reactions to seeing her breasts had been just the ego boost Cassandra had needed. They had developed early in Cassandra's life and had greatly helped when she lied about her age to become a stripper and get off the streets as a teen younger than Jason was now. They had always been one of her most devastating assets, but the fact of the matter was she was twice as old as Jason was now, and hearing a younger man's exclamations and adulation over seeing them...well it was just what a woman in the chains of middle age could ever want.

She should reward him for that perhaps.

"Seven, no. Nine," He said in an excited rush, "Though they're tens, wow."

"Nine," Cassandra repeated with that devious smirk. She then shook her head. "Incorrect, Jason."

She tsked to him, "If you had only stuck with seven...you could have had your hands on my breasts right now, instead..."

She reached out and took hold of his sleeve pulling on it. "Time for your penalty...lose the T-shirt."

"Nine," Cassandra repeated with that devious smirk. She then shook her head. "Incorrect, Jason." Damn! He flushed and grimaced. He should have gone with his gut. Would she cover up? Tell him to get lost? That expression though...that sultry smirk seemed to promise more.

And it seemed that it did. She reached out and took hold of his sleeve pulling on it. "Time for your penalty...lose the T-shirt."

He swallowed again. She wanted him to...okay, that wasn't so bad. And it was only fair. Maybe, he hoped, she'd like what she saw. "Only fair," he said with a nod. "I'm seeing yours, so..."

Jason sat up back and straight on the lounger and tugged his shirt up and off in a simple, if inelegant motion. He tossed it at the foot of seat and then...wasn't sure what he should do. She'd put on a show for him but...what could he do? He squared his shoulders and lifted his arms up to end up folding his fingers behind his head. His young body was toned by youth and his outdoor activities but he was far from being hard cut or built. There was a mole just under his right breast and he had a faint dusting of hair along the line of the junction of his collarbones and then down between his pectorals.

IC: Cassandra Delacourt

She reached out and took hold of his sleeve pulling on it. "Time for your penalty...lose the T-shirt."

Cassandra watched his reaction closely. Would he balk now that he could guess what further penalties would include? Would he decide to leave with only seeing her breasts? Was that enough of an incentive to keep him playing her game? Did he have the courage to keep playing with her?

She watched him swallow saying with a nod, "Only fair, I'm seeing yours, so..."

He moved sitting up in the chair. His hands reached down to take the hem of his shirt and began lifting it up. Cassandra watched him like a hawk watching a field mouse just before swooping down to pluck it up for its supper. He was a lean boy, but not unhealthily skinny. She noted he had good broad shoulders perfect to rake her nails down on. He also had the lightest sprinkling of chest hair reaching up to his collar bone and narrowing down towards his navel before vanishing under the waistband of his cute blue shorts.

"Nice," Cassandra stated to him. Her hands had began roaming over her breasts and down to the thin fabric of the thong covering her own sex. It was getting wetter as a dozen wicked thoughts and ideas flitted through her mind.

"Would you like to try again to win the right to touch my breasts, Jason," She continued, "I'm thinking of a number between one and twenty."

He gave his answer and she shook her head once more, "Incorrect."

She had already decided no matter what number he chose it would be the wrong one. Though once he found out what the penalty he would have to pay...she didn't think he'd complain too much.

One hand slipped beneath her thong to trace over her sex as the other hand reached out to him. "Time for your penalty, Jason. Sit up and face me."

Once he did she stretched out her arm and began tracing her fingers over his chest and the tiny delicate chest hair there. "Keep your hands where they are. You haven't won the right to touch me yet."

Fingers began to play over one of his nipples as another scratched over the mole just underneath it as the fingers under her thong began delving inside her hot moist pussy.

"Now I am thinking of a number between one and fifty, Jason."

He felt pleased and a little disquieted by the hungry eagerness on her face when she looked over his bare chest. It was incredibly hot and flattering to have someone as sexy as her looking at him like that. At the same time though, the predatory focus made slid a thread of unease into his emotional mix. It was all but lost in his roaring arousal hut it was there nonetheless.

She gave him another chance and he nodded, licking his lips. Don't blow this. God, just look at those tits! Like a dream come true. "Yeah, okay. Uh, 11." He knew wrong before she said anything, just from the gleam in her eye. "Damn." Fuck, that was frustrating! But he didn't want to show it much or risk this naughty game ending.

At her instructions he scooted closer to his on the edge of the lounger facing her. His eyes widened as one of her hands slipped under her thong. She was- And right in front of him! "Holy crap," he breathed. The youth was so intent on that he almost didn't notice her reaching towards him. When her warm, soft, so smooth hand touched his chest, the rest if that breath escaped him in a low groan. He swallowed as her hand roamed and explored him, "Oh, wow, that's...just your touch feels so nice." His hands stayed where they were by her command but gripped the frame of the long chair tighter, his knuckles whitening a bit from it.

The game kept going. Was this another chance to touch her breasts or for something else? He didn't care. Should he guess her measurements? It worked for Sherlock. Or was it something else? "18," he said. As his guess and a reminder.

IC: Cassandra Delacourt

Fingers began to play over one of his nipples as another scratched over the mole just underneath it as the fingers under her thong began delving inside her hot moist pussy.

"Now I am thinking of a number between one and fifty, Jason."

One hand continued playing with her pussy underneath the fabric of her thong the other continued running fingertips over his chest.

"Oh, wow, that's..." He stammered, "...Just your touch feels so nice."

She smiled like the cat that ate the canary at that as fingers trailed lower down his body debating whether of not to see if young Jason was ticklish yet...perhaps later.

Then he gave his answer. "Eighteen."

That seemed like an oddly specific number. Perhaps it was in reference to his age...perhaps it was a reminder to her that he was nominally at the age of being a consenting adult now...It hardly mattered to Cassandra now however. Eighteen, seventeen...no matter what his age, right now she was going to have her fun, and damn any of the consequences.

"Eighteen," She repeated before beaming a wolfish smile, "Very good, Jason, that's the correct answer."

She lifted her hand from his chest and held it flat palm up between them. "If you want your reward give me your hand...only one, Jason."

She took his hand and guided it to her breasts next exerting absolute control over it as she felt his hand caress and rub over the smooth skin of her left breast and then her right one. Her fingers spread out over the top of his insinuating themselves between his causing them to spread out over her breast. Then they moved over them and pressed down enough to get him to squeeze her breast the way she liked. Then Cassandra moved his pointer finger and thumb to circle over and close around her nipple. She spent the next few minutes teaching him how to roll and pinch her nipples the way she liked.

"Mmmm..." She moaned arching her back into the ministrations of his hand on her breasts, "I love the callouses on your fingertips, Jason. Is that from any activity in athletics or from years spent with them on the buttons of those video game controllers kids spend all their time on these days?"

"Remember," She told him as her hand left his and lowered down her body to join its sister underneath her thong, "Just my breasts, Jason."

For several minutes she allowed them to stay like that with his hand having free reign over her breasts and nipples as she used both hands to plunge two fingers inside her sex as fingers from the other ran circles over and flicked across her clit. She then spread her legs wide, placing her bare feet on the floor of her pool's patio tiles. The hand pushing her fingers inside of her began to pump in and out a little more rapidly of her steaming moist pussy-more than strictly necessary right now, but it provided an irresistible show for Jason's viewing pleasure.

Then it was over. Her hands pulled out of her thong. One had two fingers soaked with the juices of her arousal. She used the other to take him by the wrist and lift his hand off of her breasts.

"That's enough...for now, Jason," She told him, "But it should be evident to you by now where this game may take us. So why don't we skip a couple steps and get to the really fun part of this game?"

She lifted the hand with the two fingers coated with her juices between them, "Would you like a taste? Well, you can if you can guess correctly the number I'm thinking of between one and one hundred."

"Eighteen," She repeated before beaming a wolfish smile, "Very good, Jason, that's the correct answer."

He grinned right back, a feeling of triumph bursting to life in his chest. He nodded his head at her conditions as his anticipation drove any concerns or feelings about fairness out of his mind. He was going to touch his first naked breast and it was on the hottest woman he'd ever seen in the flesh.

Even with her hand guiding his making it a little strange, that first touch sent a shiver down his spine and sent a thrill that both chilled and sizzled his nerves. "God damn," he whispered in a tone of awed reverence. She drew his hand along the sumptuous curve and pressed into the plush, soft, rounded mound. His cock pulsed in his shorts and he could feel sticky pre-cum seeping onto his boxers. "Perfect." The feel of her tit swelling against his hand as she breathed made it almost a living thing.

He noted how she was moving his hand and realized she was showing him how she liked to be touched. Jason attended her lessons with a devotion he'd rarely shown, or needed to, in school. His free hand stayed where it was but he began to mirror the movements with it to train himself with physical and mental memory.

"Mmmm..." She moaned arching her back into the ministrations of his hand on her breasts, "I love the callouses on your fingertips, Jason. Is that from any activity in athletics or from years spent with them on the buttons of those video game controllers kids spend all their time on these days?"

"Both, I guess. I play a lot of video games but I do outdoor stuff too. Not really sports but camping, hiking, that kind of thing." His hands got their roughness tying knots, chopping wood, and other rustic pursuits that would seem odd for a kid from the suburbs.

"Remember," She told him as her hand left his and lowered down her body to join its sister underneath her thong, "Just my breasts, Jason."

God, he understood the warning but right now touching her breasts was plenty. He just wished she'd let him use both hands. He kept up the motions she'd used on first one luscious jug and then the other. He squeezed with the same pressure and his fingers pulled and pinched, practicing his surprise teacher's dirty lesson.

It was impossible to keep his eyes still as the squishing slurp as she fingered and worked her pussy. He'd heard other guys make jokes about the smell of a woman down there; saying it was like fish or rotten meat. To his nose it was pungent but earthy and tangy. He wondered what it would taste like. At the same time, her gorgeous tits kept dragging his gaze back.

He blinked with sudden surprise when her hand met his and pulled it back. "That's enough...for now, Jason," She told him, "But it should be evident to you by now where this game may take us. So why don't we skip a couple steps and get to the really fun part of this game?"

She lifted the hand with the two fingers coated with her juices between them, "Would you like a taste? Well, you can if you can guess correctly the number I'm thinking of between one and one hundred."

Jason licked his lips. The stakes and the odds kept going up. He knew it was his imagination but his left hand felt warm from her breast. He also began to wonder if she was really picking numbers or just jerking him around...but he did care either way. "42."

Hey, Douglas Adams wouldn't lead him wrong, right?

IC: Cassandra Delacourt

She lifted the hand with the two fingers coated with her juices between them, "Would you like a taste? Well, you can if you can guess correctly the number I'm thinking of between one and one hundred."

Cassandra watched him lick his lips uncertainly before answering, "Forty-two."

"Forty-two," She repeated looking him in the eye and deciding whether she'd give him this in that one moment.

Decision made, she smiled to him, "Correct."

"Stay still." The fingers moved forward and she traced her juices over his lips before pushing past them into his mouth so he could taste and savor the flavor of her arousal.

She allowed him to lick her finger and then the other for a few minutes before pulling away.

Her hands returned to sneaking underneath her swimsuit and playing with her nipples as she looked at Jason. "How long will your parents be gone?"

At his answer the smile deepened.

"This time we'll do something different, Jason," She told him, "I want you to decide the stakes this time."

Her hand lifted up from between her legs. Her fingers were freshly coated with more of her juices. "Take your time to think it over. What do you want to win next?"

After he gave his answer she extended her tongue and licked the juices off pointedly making it suggestive of how she'd lick up and down his cock. She paused from that asking him, "And what would be the penalty if you guess incorrectly again? What would you be willing to do if you wind up being wrong?"

She returned to suggestively licking the juices off of her fingers as he answered that question.

"Very well then," She announced, "I am thinking of a number between one and two hundred."

A foolish grin showed clean teeth. He wanted to cheer or something but that was probably a little too immature for someone classy like Cassandra. He wanted to meet her fingers with his tongue but was very aware if her rules. One misstep and he would lose the erotic experience of his young life. Jason had to be careful when and how he pushed back. If he even tried to.

That tangy musk scent grew stronger in his nose as she brought her fingers to his lips. The smell tickled but not like he had to sneeze. It was warm but quickly cooling on his lips with a thick and creamy texture that was a surprise. He wasn't sure what he expected, really, though. Finally she pushed her fingers into his mouth and he could taste her full and clear. It had an earthiness to it that almost reminded him of mushrooms but the there was that almost acidic tang. Jason gently sucked on the offered fingers for a minute before beginning to run his tongue over them, cleaning her juices. He thought he liked it but he wasn't sure. He was sure he wanted to taste more to find out. From the source, if she'd let him.

Cassandra pulled her fingers back after just a bit more. He didn't complain though he had been enjoying the dirtiness of the act as much as the fact that those digits were just in her snatch. He liked his lips then, capturing the last of the essence she'd favored him with. "I liked that," he said, more out of a need to say something than anything else.

Her hands returned to sneaking underneath her swimsuit and playing with her nipples as she looked at Jason. "How long will your parents be gone?"

The answer burst from his lips before he could stop to think if it was a good idea to tell her the truth. "Six weeks. I'm on my own until they get back, then I'm headed to college."

Her smile was all sensual anticipation and predatory satisfaction. He was hers to toy with without any risk of interference. That smile made his dick throb even as he felt a strange anxiety he couldn't define. "This time we'll do something different, Jason," She told him, "I want you to decide the stakes this time." Her hand lifted up from between her legs. Her fingers were freshly coated with more of her juices. "Take your time to think it over. What do you want to win next?"

"That's a big question.". What did he want? Everything she'd give him but he wasn't dumb enough to give her that answer. He wanted to touch her more. He wanted her to touch him. He wanted sex. He wanted her sucking his cock. He wanted to taste her sex. But that was a lot of steps along her game, if it was part of the stakes at all. He pursed his lips slightly; think about it another way. If none of that happened...what would he like to walk away with?

Right. "I want to win you taking your swimsuit off and staying naked." God, how he'd have wanted to see her nude. If thus fell apart and she sent him off blue balled, he'd have a full and perfect memory of her to finish things himself.

She teased him before speaking again. Showing him exactly how she could use those full lips of hers. Damn, she was a bad, bad woman. And he loved it. She paused from that asking him, "And what would be the penalty if you guess incorrectly again? What would you be willing to do if you wind up being wrong?"

"Penalty..." This was easier. "Fair's fair. If I lose, I, uh, I'll take off the rest of my clothes." He hoped that would be enough.

"Very well then," She announced, "I am thinking of a number between one and two hundred."

Crap. With a range like that, it was a shot in the dark. It could be a riddle, which would mean the range was actually one hundred to two hundred. Not much better. "I guess...169."

As good as any. Maybe the mild naughtiness would amuse her a little.

IC: Cassandra Delacourt

"This time we'll do something different, Jason," She told him, "I want you to decide the stakes this time."

"That's a big question." He replied cautiously.

Her hand lifted up from between her legs. Her fingers were freshly coated with more of her juices. "Take your time to think it over. What do you want to win next?"

After a moment to consider he answered, "I want to win you taking your swimsuit off and staying naked."

An eyebrow quirked and she teased, "Is that all? You could've asked for so much more Jason, and I would be obliged to give it to you. That's the rules of this game after all."

Then she shrugged. "On the other hand you are quite the peeping tom and as you may have noticed by now I'm exhibitionistic enough to get turned on by showing off my body to you."

After he gave his answer she extended her tongue and licked the juices off pointedly making it suggestive of how she'd lick up and down his cock. She paused from that asking him, "And what would be the penalty if you guess incorrectly again? What would you be willing to do if you wind up being wrong?"

"Penalty..." He repeated thoughtfully and then shrugged, "Fair's fair. If I lose, I, uh, I'll take off the rest of my clothes."

"Very well then," She announced, "I am thinking of a number between one and two hundred."

"I guess...169." Came his answer.

She wondered if he had figured out her little trick to her question. She had intentionally worded it so it could be either between one and two hundred or one hundred to two hundred. If that was the reason behind him choosing 169 then he was starting to play this game right.

"Correct," She told him sitting up and rising up from her chair. She stepped over to the edge of the pool in direct line of sight to him. She stood there facing away from him. She turned her head to look at him over her shoulder. "Are you ready for your reward, Jason?"

It would've helped if she had some music playing but she drew on her years as a stripper to begin dancing-swaying erotically really-in place as one hand lifted and slowly began pushing the strap of her bathing suit over her shoulder. Teasingly she began to push down her suit over the other shoulder and down her slender torso to her waist.

She bent over as her thumbs slid underneath the straps of her thong. She spread her legs a little so she could see his face as she asked him, "How many times have taken a peek through my windows hoping to see a sight like this?" The thong began to slide down over the cheeks of her ass revealing the last little bit of her barred from his eyes.

"How many times, Jason," She said as it slowly lowered and lowered down, "How many times did you lay in your bed and reach under the covers, and take your cock in hand, imagining me like this?"

The Swimsuit slid down to land on the deck of the pool. She turned and walked over to him and stood hands on her hips with that wicked smile. "Am I everything you imagined when you were fantasizing about me?"

She sat back down in her chair. "Well let's start the next round. What do want to win this time? And what penalty will you pay, Jason?"

Her hands resumed roaming over her body. "Well then, I am thinking of a number one and five hundred."

He felt a bit of indignation at being called 'quite a peeping tom.' He'd only ever peeped at her and it was accidental...at first. Okay, maybe it was fair. But more important was her answer. She was playing him even as he knew she was doing it, almost like a reality tv show host stretching the reveal to build tension.

"Correct," She told him sitting up and rising up from her chair. She stepped over to the edge of the pool in direct line of sight to him. She stood there facing away from him. She turned her head to look at him over her shoulder. "Are you ready for your reward, Jason?"

She stood and took a few paces to stand facing away. A sinuous, sinful motion went through her and he let out a long, appreciative breath. How was she doing that? Her body barely moved but the motions she made spoke silently of untold sexual delights that she could offer him. "Holy crap," he murmured. He felt...almost like she was stroking his dick from a distance. Seriously, how did she do it?

She bent over as her thumbs slid underneath the straps of her thong. She spread her legs a little so she could see his face as she asked him, "How many times have taken a peek through my windows hoping to see a sight like this?" The thong began to slide down over the cheeks of her ass revealing the last little bit of her barred from his eyes.

Jason could feel his cheeks heating and an impulse to look away but it couldn't overcome the siren song of her body and his surging hormones. God damn, she had a terrific ass. A terrific everything! He was leaning forward in his seat, almost but not quite lifted up off of it. He felt compelled to answer her naughty question but not knowing what to say, he remained silent.

"How many times, Jason? How many times did you lay in your bed and reach under the covers, and take your cock in hand, imagining me like this?" The thing slid down those mile long legs until the swimsuit landed on the deck.

As she approached him, he shook his head, "God, dozens. You've been my go to fantasy." The teen was staring at her as if intending to memorize the sight of her. As though she might disappear at any moment or that he'd wake and it would all turn out to be a dream. "I imagined you so many times, came thinking of you, of this."

She stood hands on her hips with that wicked smile. "Am I everything you imagined when you were fantasizing about me?"

"Fuck, yes. And more." Because this was real. That beat a thousand fantasies. His eyes roamed before locking on her pussy. They widened his expression amazed as he took in the sight of it. His expression was equal parts hungry and wondrous as he looked on the holiest part of her sinful form.

She sat back down in her chair. "Well let's start the next round. What do want to win this time? And what penalty will you pay, Jason?"

Her questions shook him from his reverie of ogling. This time he had no hesitation, "If I win, I want to touch and taste your, uh, your pussy." He flushed a little saying it out loud and immediately felt foolish for doing so. "If I lose, I'll strip all the way, same as before. And I won't touch myself until you say so."

Her hands resumed roaming over her body. "Well then, I am thinking of a number one and five hundred."

Crap. This was all up to her. No way she wasn't just choosing if he lost or won. "Okay. I choose...411." Weak joke, sure, but it was something that might amuse.

IC: Cassandra Delacourt

"How many times, Jason," She said as it slowly lowered and lowered down, "How many times did you lay in your bed and reach under the covers, and take your cock in hand, imagining me like this?"

He was blushing, and she gave him points for having the lecherous need to keep looking rather than becoming too embarrassed at seeing his first naked woman in the flesh and looking down or away.

She straightened back up and turned around. She began to strut, hips swaying with each step, back over to the deck chairs. She didn't even bother to hide her body from his gaze as she approached.

"God, dozens," He answered her question shaking his head "You've been my go to fantasy."

She came up to him placing hands on her hips giving him plenty of time to take as much of the sight of her body as he could, and damned if he wasn't too. His eyes were wide like a child on Christmas roving over every inch of her. She could feel his on her breasts, which had not yet began to sag despite her reaching middle age. Then they traveled down to her shaved pussy.

Jason was an eighteen year old kid. The truth of the matter that while Cassandra fought it ruthlessly with exercise and dieting she was still twice as old as him, but the look he was giving her did wonders for her thirty-six year old ego.

She gave him more points for that. If he kept up with racking up the points like that Cassandra might just keep him for more than just this one game. Of course the deciding factor in that decision would be how much fun for her he would be in this game.

Only time would tell.

She stood with her hands on her hips with that wicked smile. "Am I everything you imagined when you were fantasizing about me?"

"Fuck, yes. And more." Came his reply in a tone that seemed to mingle equal parts awe and hunger in four words.

She sat back down in her chair. "Well let's start the next round. What do want to win this time? And what penalty will you pay, Jason?"

His answer came immediately hot and eager, "If I win, I want to touch and taste your, uh, your pussy."

The flush to his cheeks from how enthusiastically he had announced that made Cassandra chuckle deviously. "And if you lose?"

"If I lose, I'll strip all the way, same as before," He told her and she arched an inquisitive eyebrow wondering whether he'd keep offering stripping his shorts off and only that as a safe thing to risk in her game here.

Maybe he caught on for he then added, "And I won't touch myself until you say so."

Her hands resumed roaming over her body. "Well then, I am thinking of a number between one and five hundred."

"Okay. I choose...411."

"411," Cassandra repeated then shook her head, "Incorrect."

She pointed a finger at the blue shorts he wore, "Strip."

When he got up to do just that she told him, "Not there." She pointed to the edge of the pool where she had just stripped for him. "There, and do it just like I did for you."

When he reached it she gave him a wolf-whistle, "Dance, studly, dance!"

"411," Cassandra repeated then shook her head, "Incorrect."

Jason nodded, not quite glumly. He'd expected it, really. That big a range meant it was pretty much a sure loss. Assuming she wasn't deciding arbitrarily whether he won or lost.

She pointed a finger at the blue shorts he wore, "Strip."

When he got up to do just that she told him, "Not there." She pointed to the edge of the pool where she had just stripped for him. "There, and do it just like I did for you."

Oh, boy. Him do a strip tease? How could he? He wasn't sexy. And he didn't know how to dance! But she wasn't giving him a choice. Maybe he could've given up on this game too but Cassandra was do sexy and this was all as awesome as it was terrifying.

When he reached it she gave him a wolf-whistle, "Dance, studly, dance!"

He felt his cheeks heating and knew they were probably bright red and that it would be down his neck too. Jason felt incredibly awkward but also kind of good. He just had to do what he could. Remember what she did and mimic it. The youth closed his eyes and took a few breaths. Remember that song from his parents' days, the Austin Powers one.

Jason had been standing with his legs together but he started a sinuous motion at the shoulders that traveled down his whole body. He slid his feet apart as he raised his arms and stretched them back, flexing to show the wiry musculature of his arms and back. Swaying and rolling his hips, he brought his hands forward to unbutton his shorts and then slid them down but only just enough to show the pert globes of his ass. He looked over his shoulder at her with what he hoped was a 'come hither' look and reached back to squeeze his exposed ass cheeks.

This was so weird! His dick was still hard though, so maybe he liked it?

The teenager grabbed hold of his ass and pulled his cheeks apart for a few moments before letting go. He slapped his own ass with both hands and then brought his legs back together. Jason bent forward and pushed shorts and boxers both down his legs. He took a breath and then stepped to the left out of them, his right foot kicking them away. He stayed bent over, swaying and wiggling his butt. His scrotum hung between his legs but his erect cock stood straight out and couldn't currently be seen. He did a roll of his hips, gave his ass another slap, and the spun to face her. He spread arms and legs both, hands upturned and his head looking down. His steely prick bounced and wobbled with his movement before he went still.

Where had that come from?

He also now felt nervous. How did he measure up? Jason had never actually measured his manhood but from the gym showers he knew he was bigger than a lot of guys. But what did that mean? Would it be enough for her to like? Would she laugh at him?

IC: Cassandra Delacourt

When he reached it she gave him a wolf-whistle, "Dance, studly, dance!"

The blush that was coloring Jason's cheeks and the back of his neck was adorable. Cassandra chuckled at that, but that all ended when he began to move. He managed to attempt the sinuous movements she had performed for him as he stretched his arms back to show the lovely lean muscles up and down his teenaged body.

Cassandra watched him unbutton those cute blue shorts and she hungered impatiently for him to turn around and let her see his cock at last. Jason's hand traveled to the waistband of those shorts and pushed down to expose just a little of the swell of pale asscheek. It was not a big pair of buttocks but on the other hand their was enough of them to nibble and bite or to provide a good handhold as he fucked into her or when she spread them apart to use one of her strap-ons on. Then he spread them wide and Cassandra smiled as she got a glimpse of his puckered asshole. If their game progressed she'd look forward to getting better acquainted with it.

His dance routine continued and Cassandra gave Jason more points in his favor for committing to this striptease completely. He pushed the shorts down further bending forward and she got a glimpse of his testicals hanging between his spread thighs. After a playful slap of his buttock he suddenly spun back around to face her and Cassandra finally got at good look at what he had to work with in the eventuality of her fucking him.

At seven inches it was an inch-maybe two with Cassandra's coaxing-past the average. Not the largest cock she'd fucked, but that was a one in a million cock. Also his seven-incher was the best of both worlds. It was long enough to reach all the places she'd want him to inside her, thick enough too, but not too long he could hurt or damage her when or if they engaged in some brutal fucking or go for a marathon session.

Yes, she licked her lips looking at it throb with the rapid beating of his heart imagining all the ways she'd get better acquainted with it as well. Overall she was well pleased with it. And the way her hands delved fingers inside of her now even wetter pussy or playing with her nipples unconsciously testified to just how aroused she was getting thinking of the many many games she'd play with his body as her gameboard.

"Very Impressive, Jason," She told him as he came to his deck chair, "If I had a stack of dollar bills right now I'd be making it rain. Seriously you could make a lot of money in a male revue stripping your clothes off for lonely housewives."

When he sat back down Cassandra turned to regard him again, "Tell me, what would you like to do now, Jason?"

"Shall we continue," She asked him, "I think I will decide what you will win this time and what penalty you will pay for this one."

After his answers she said, "I'm thinking of a number between one and one thousand."

His heart beat faster and he felt a sheepish grin spreading over his still blushing face. The sexual goddess that was Cassandra Delancourt was looking at him and his cock like they were good enough to eat. She was licking her lips! The normally good boy felt like he was a hundred feet tall just then.

"Very impressive, Jason," She told him as he came to his deck chair, "If I had a stack of dollar bills right now I'd be making it rain. Seriously you could make a lot of money in a male revue stripping your clothes off for lonely housewives."

He laughed a little at that, sitting back down opposite her. "You think so? I guess that could be one way to make some money when I'm at college." Could he actually? He kind of liked that idea. But how did you even get started doing that or even finding one of those revues?

Her question brought his full attention back to the here and now. When he sat back down Cassandra turned to regard him again, "Tell me, what would you like to do now, Jason?"

That was a loaded question in lots of ways. What did he want to do? Everything! But he was sure that was a pretty callow answer. "That's, I mean, seeing you naked and the way you were looking at me, I'd like to do...a lot. To touch you and feel your hands on me, on my, uh, my dick. I'd like to kiss you, feel your lips and tongue on me. I'd like to learn how to eat your pussy and please you. I'd like to feel your breasts against my chest, wrapped around my cock. I want...I mean, it's probably obvious, but I would really like to, for you to, uh, be my fi-, I mean to f-fuck you.". It was all true. He wanted even more but much of it he wasn't sure how to put into words. Nebulous desires for sexual exploration beyond what most people would consider normal.

"Shall we continue," She asked him, "I think I will decide what you will win this time and what penalty you will pay for this one."

He nodded slowly. "Okay. I did get to choose the last two times." He licked his lips, "What are the stakes now?"

After his answers she said, "I'm thinking of a number between one and one thousand."

Christ. How was he supposed to...he wasn't supposed to, that was how. He smiled a little, "Couldn't you just tell me now if I win or lose? I guess that's not the spirit of the game though." Would she punish him for that? Maybe he should have just played dumb. "So, I guess 500."

IC: Cassandra Delacourt

"Very Impressive, Jason," She told him as he came to his deck chair, "If I had a stack of dollar bills right now I'd be making it rain. Seriously you could make a lot of money in a male revue stripping your clothes off for lonely housewives."

"You think so? I guess that could be one way to make some money when I'm at college." He laughed plopping his naked ass back down into his chair.

"There's an idea," She agreed giving him a few more bonus points to his mounting tally, "You have a natural talent at it. The key to making it into a career is becoming lost in the music and letting go of your inhibitions, unless you are like me and have no inhibitions to begin with."

Cassandra turned to regard him again, "Tell me, what would you like to do now, Jason?"

"That's, I mean, seeing you naked and the way you were looking at me, I'd like to do...a lot," He said after a moment.

"What do you want to do most right now," She asked him.

"To touch you and feel your hands on me, on my, uh, my dick," He said.

She lifted her hands to her mouth and extended her tongue to lathe over it like she would use it over his cock before asking leadingly, "And what else..."

"I'd like to kiss you, feel your lips and tongue on me. I'd like to learn how to eat your pussy and please you. I'd like to feel your breasts against my chest, wrapped around my cock. I want...I mean, it's probably obvious, but I would really like to, for you to, uh, be my fi-, I mean to f-fuck you."

Well that opened the flood gates. She gave him another bonus point for knowing what he wanted and not being afraid to tell her after some coaxing.

"Shall we continue," She asked him, "I think I will decide what you will win this time and what penalty you will pay for this one."

He slowly nodded to that, "Okay. I did get to choose the last two times. What are the stakes now?"

"That would be telling," She said with a naughty shake of her head.

She smiled to him, "I'm thinking of a number between one and one thousand."

His eyes opened wide at that kind of spread. She had just given a one in one thousand chance of guessing the correct number, after all.

"Couldn't you just tell me now if I win or lose," He asked her with a wary smile on his adorable face, "I guess that's not the spirit of the game though."

"No its not," She agreed.

"So," He finally said after a second between them, "I guess 500."

"Well then..." She said rising up on her feet and walking over to him. "I think you may be a little tired of playing my game, Jason, but remember what I told you. It's my rules, and I don't remember saying that they had to be anywhere close to being fair."

She started heading for the sliding glass door to her kitchen. "If you don't like that you can pick back up your clothes and head back to your house right now, and no one will have hurt feelings between us here."

The sound of the glass door sliding open had an air of finality. She stepped inside and looked over her shoulder back at him. "Five hundred was correct by the way, and that leaves the matter of your reward."

She slid the door closed but stopped with it cracked open keeping him on the outside. "I want you to pick a number between one and five, and no I won't tell you what you're choosing until after you've made the choice."

When he gave his answer she nodded to him through the glass. "That's how many hours you will have to wait. Go home, Jason. Shower, dress nicely, stretch and limber yourself up, eat something easy and most of all rest up. You will need the energy after all."

She smiled to him, "For when your time is up this door will be unlocked and wide open for only thirty seconds. And if you decide to step inside you will get your reward...this promise." She cast a lustful look staring into his eyes as she continued, "I promise that if you step inside this house at exactly the time I specified I will make it my unholy mission in life to put all the filthy perverted fantasies you've had about me as you've masturbated to shame before sunrise tomorrow morning."

The glass door slid shut and she made a show of turning the lock. Then Cassandra turned and walked away without a second look or so much as a "See you later."

"Well then..." She said rising up on her feet and walking over to him. "I think you may be a little tired of playing my game, Jason, but remember what I told you. It's my rules, and I don't remember saying that they had to be anywhere close to being fair." She started heading for the sliding glass door to her kitchen. "If you don't like that you can pick back up your clothes and head back to your house right now, and no one will have hurt feelings between us here."

Jason grimaced. Shit, that had really pissed her off. He'd blown it. He thought she might appreciate that he'd figured out the game. Maybe even give him a little credit for being a little clever, but instead he got this. Great. Man, he was so fucking stupid!

The sound of the glass door sliding open had an air of finality. She stepped inside and looked over her shoulder back at him. "Five hundred was correct by the way, and that leaves the matter of your reward." She slid the door closed but stopped with it cracked open keeping him on the outside. "I want you to pick a number between one and five, and no I won't tell you what you're choosing until after you've made the choice."

He stood up as well. Jason wasn't sure what was happening now. It had seemed like she was going to end it but now there was this. He was horny, frustrated, and confused. But he wasn't dumb enough to do anything but answer; Cassandra Delancourt wouldn't give him another chance, he was sure. Assuming that this was a second chance and not just the set up for a mic drop moment. "Four."

When he gave his answer she nodded to him through the glass. "That's how many hours you will have to wait. Go home, Jason. Shower, dress nicely, stretch and limber yourself up, eat something easy and most of all rest up. You will need the energy after all."

She smiled to him, "For when your time is up this door will be unlocked and wide open for only thirty seconds. And if you decide to step inside you will get your reward...this promise." She cast a lustful look staring into his eyes as she continued, "I promise that if you step inside this house at exactly the time I specified I will make it my unholy mission in life to put all the filthy perverted fantasies you've had about me as you've masturbated to shame before sunrise tomorrow morning." The glass door slid shut and she made a show of turning the lock. Then Cassandra turned and walked away without a second look.

Jason stared at the closed door in shock for a full ten count before slowly sitting back down. "Okay then," he said. No one was there except for him but he still felt like saying something, even if it was to no one. "See you later."

Holy shit. This was...she would, with him! Unless he fucked up again or missed it. What time even was it? His phone, crap! Jason scampered to his discarded shorts and dug into the tight pocket. He would have been annoyed had anyone described his movement as a 'scamper' but it was what it was. He'd forgotten it was in there in his excitement. "Don't be busted," he prayed as he pulled it out. The screen lit up and he sighed. "Thank God. All right, next thing..."

He set an alarm for three hours and thirty minutes from now. Then he set another one for three hours and fifty minutes from now. "No way am I missing this." He sighed and glanced at the pool, his nude reflection looking back at him. "Hey, next time you want to say something clever, just keep your mouth shut. You almost blew it."

The teen redressed and was about to leave when he noticed her discarded swimsuit. He picked it up and breathed in the faint remnants of the scent that her wet pussy had left. Then he folded it and put it on the pool chair she'd used. He wasn't trying to curry favor, really, it just seemed like the polite thing to do. Then he walked back around out of her yard and to his house.

He felt oddly exposed on that short walk. If anyone noticed him coming out of her backyard, would they suspect him of something? That was a little paranoid. They might suspect him of yard work, maybe. He was a good kid, after all. Besides, who the hell was he that anyone would care what he was doing? He needed to check that ego, especially when he went back.

The next few hours were paradoxically the slowest of his life yet everything seemed to take too much time. First, he cooked himself a simple dinner that went in the oven to stay warm; he'd eat about an hour before going over. Then he went and pulled out the suit his parents had bought him for job interviews or other networking events at college and set out a tie, socks and shoes to go with it.

He should bring something with him. You were supposed to when you visited someone's house. And should he bring flowers? It wasn't a date. Would it send the wrong message or the right message? Or any message? ...Maybe he was over thinking this. She'd told him to rest up, not to fret. Yeah, easier said than done.

He tried, taking a quick cat nap for about an hour, a firm time thanks to another alarm on his phone. An hour and half to go. He ate his dinner with the practiced speed he'd learned on hiking trips, not dangerously fast but efficiently. Then it was time to shower. He took care to fully lather and scrub every inch of his body, even his ass crack, rinsing thoroughly. The thirty minute alarm went off as he was drying off. Jason stood nude in the steamy air of the bathroom and took severs deep breaths. "Okay. Get ready," he said to his reflection in the mirror. "It's only changing the way you see the entire world. No big deal, right?" His reflection did not look convinced.

A careful shave later, he dressed in his suit and made ready to leave. The ten minute alarm buzzed as he pondered the sparsely populated liquor cabinet his parents kept. He snatched up a bottle of brandy that had sat unopened since his uncle had given it to Dad two years ago.

The self consciousness he'd felt earlier in the day was nothing compared to what he felt walking down the sidewalk and then into her yard now. Then he'd been dressed normally. Now he was in a dark blue suit with oxblood dress shoes and a pale yellow tie over a white button down. The brandy bottle was tucked under one arm. His hair was still just a bit damp and well combed, his face freshly shaven. No nicks or cuts, thankfully. He hadn't put on any of his father's cologne or aftershave. From what he'd read, a lot of women preferred a man's normal smell, assuming he was clean, of course. He felt like he had a flashing light over his head that read "Pay attention to me" but his progress certainly wasn't arrested.

Jason made it to the patio by the pool with a few minutes to spare. His heart was racing and his palms felt sweaty. He needed to calm down. He knew that. But how? He adjusted his tie with one hand, the other turning the bottle over again and again. He stood close to the door, determined not to miss his window of opportunity. When it opened, he would be through with twenty-nine seconds to spare. That was the plan, anyway.

IC: Cassandra Delacourt

She smiled to him, "For when your time is up this door will be unlocked and wide open for only thirty seconds. And if you decide to step inside you will get your reward...this promise." She cast a lustful look staring into his eyes as she continued, "I promise that if you step inside this house at exactly the time I specified I will make it my unholy mission in life to put all the filthy perverted fantasies you've had about me as you've masturbated to shame before sunrise tomorrow morning."

The glass door slid shut and she made a show of turning the lock. Then Cassandra turned and walked away without a second look or so much as a "See you later."

She went into her fridge and microwaved a quick meal, and ate only half.

Cassandra smiled as she realized that she was going to take the virginity of a teenaged boy tonight-repeatedly. He hadn't told her he was of course but the years she'd spent as the best high-priced escort to be found anywhere gave her the instincts to size a John up at a glance, and those same instincts told her that Jason screamed "I have never fucked a woman before in my life."

At least that was until tonight.

That gave her an idea for a new story and opened her trusted notebook and for the next forty-five minutes to an hour jotted down some notes for it. Sighing she decided she should begin getting ready for Jason's deflowerment.

She went up stairs to take a thorough shower. Completing the pre-appointment routine from her call girl days in record time. She dried and brushed her hair, applied her makeup. From there she crossed over into her huge walk-in closet picking through her large collection of dresses and costumes.

"What to wear? What to wear," She murmured as her hands pushed coat hangers aside. What would give Jason the right impression? She had corsets and catsuits, but while she wanted to be in charge, she didn't want the hassle that came with femdom...perhaps of he impressed her tonight they'd hook up again so she introduce him to a flogger...perhaps. That left her costumes? She had a vast array from slutty nurse to stern teacher to shy catholic schoolgirl to bubbly cheerleader. No, again it was for another day.

She decided on a tight little black dress she could wear out to the club...well it dipped low enough it showed a good deal of cleavage and it rode high on her hips, perhaps going a centimeter or two lower than her pussy. If she bent over in it Cassandra would be advertising all of her wares to anyone looking.

Which is why it would be so much fun to wear it for Jason tonight.

She chose a black shelf bra that lifted and showcased her bare breasts to wear beneath it. Also a pair of stockings with a matching garter belt. She didn't bother with the pair of panties that went with the set. Damned thing would just get in her way when it came down to do the deflowering.

She dressed and checked the time. It was getting close to showtime. She checked herself in the mirror.

It occurred to her Jason might've gotten scared and decided to not show up as she walked back down the stairs on her tall stiletto heels. What would she do then? She was all hot and bothered to fuck Jason tonight.

She went back to the kitchen checking the time. It was fuck time.

At the specified time she unlocked the glass door and slid it open. When he stepped inside. She thanked for the brandy and set it down on the kitchen counter. Then Cassandra shoved him hard against wall and kissed him with all the fire within her.

"This is how its going to go down," She told him between soft bites of his lips. "We're going to play a new game. First I'm going to throw you onto my bed. Then I'm going to climb onto your cock and ride it until it breaks off or the sun rises tomorrow morning." To emphasize her words her hand lowered to get a good feel of the tent in his pants, "Also you should know that when you chose the number four you weren't just choosing how many hours you had to wait either. You get only four orgasms as I fuck you tonight, Jason. Any more than that and you pay a penalty for each one you have."

She set him with her most sultry gaze in conclusion. "If you have any objections to this game then turn around and walk out that door now."

Jason stepped through the sliding door as soon as there was enough space for him to fit. It was probably kind of comical, really, but he didn't care. He was not going to miss this. He breathed out with relief and smiled a bit shyly, "Thank you, I-"

Whatever he'd been going to say vanished from his mind as he got a good look st Cassandra and blood flow shifted suddenly away from his brain. She always looked good and was always sexy. She smoldered in the casual clothes he'd seen her in when his parents insisted they all go meet the new neighbor or chance sightings going in or out of her house. She was smoking in the swimsuits worn for swimming or sun bathing that he'd seen when peeping on her. Nude, she was scorching hot. But somehow right now, she looked even hotter. Jason almost felt she she'd burn him and he hoped she would! Poured into that tiny black dress, Cassandra Delancourt was sex given form. The way it clung to her, the breath taking expanse of cleavage, the delicious indecency of those mile long legs being pretty much completely bare, those heels, it all delighted and exploded the barely legal teen's mind.

He stared openly, not quite gaping. Then she rushed him and his back hit the wall as she delivered a blistering kiss. His stunned lips answered after a moment, eager and awed. Her lush body was sweet against him, even through his suit, and he moaned into her consuming lips.

"This is how its going to go down," She told him between soft bites of his lips. "We're going to play a new game. First I'm going to throw you onto my bed. Then I'm going to climb onto your cock and ride it until it breaks off or the sun rises tomorrow morning." To emphasize her words her hand lowered to get a good feel of the tent in his pants, "Also you should know that when you chose the number four you weren't just choosing how many hours you had to wait either. You get only four orgasms as I fuck you tonight, Jason. Any more than that and you pay a penalty for each one you have."

She set him with her most sultry gaze in conclusion. "If you have any objections to this game then turn around and walk out that door now."

That look would have turned feathers rock hard. He'd thought she was turning it on this afternoon but that was nothing, nothing next to this. Jason found his voice after a few moments, "Nuh-no objections. I'll take penalties if I cum mote than four times, I get it. It'll be worth it."

IC: Cassandra Delacourt

"This is how its going to go down," She told him between soft bites of his lips. "We're going to play a new game. First I'm going to throw you onto my bed. Then I'm going to climb onto your cock and ride it until it breaks off or the sun rises tomorrow morning." To emphasize her words her hand lowered to get a good feel of the tent in his pants, "Also you should know that when you chose the number four you weren't just choosing how many hours you had to wait either. You get only four orgasms as I fuck you tonight, Jason. Any more than that and you pay a penalty for each one you have."

She set him with her most sultry gaze in conclusion. "If you have any objections to this game then turn around and walk out that door now."

It took a few minutes where Cassandra worried that she had come on far too strongly, but finally Jason found his voice well enough again to answer her.

"Nuh-no objections," He stammered.

"Good," She said pulling his yellow tie out into her hand, "And you'll accept whatever penalty I decide upon for any orgasms you may have past your fourth one?"

His answer came a lot faster, "I'll take penalties if I cum mote than four times, I get it. It'll be worth it."

"You got that right," She said winding his tie around her hand, "Since you're in...let's get on with it then."

She turned using his tie as a leash pulling him after her as she strutted over to the kitchen island. From there she pulled down a coffee mug. Then freeing the bottle of brandy of its cap and pouring herself some. She put the bottle back down, and told him, "I think a little bit of foreplay is in order first though."

She pulled on his tie still in her hand pulling him in close so her lips and his were breath's distance apart, "Do me a favor, Jason. Reach between my legs and tell me if I remembered to put on some panties."

At the feel of fingers she groaned out, "Good, then they won't be a hindrance to you."

She took the coffee mug of brandy and lifted it to sip. "You have four minutes to use your fingers to get yourself acquainted with my pussy, or if I finish my brandy first."

"You got that right," She said winding his tie around her hand, "Since you're in...let's get on with it then."

Jason felt his heart start pounding again and his face was warm. Holy shit. Holy shit, this was really going to happen. God, she was so sexy it was unreal. The way she was holding his tie, leading him on it like a leash, made his dick pulse and ache for contact. He was getting an education already; who would have thought that would be such a turn-on?

His eyes were pulled down by the sway of her hips as she strode through the kitchen, pulling him along with her. Not that she really had to pull, though the position they were in did cause him to nearly stumble once. That caused a little tension in the tie but not enough to require a corrective tug. It probably didn't help that his eyes were glued to that gorgeous ass as it swung to and fro. He felt a little bad but he also knee she had dressed to show off. And was she ever! He could almost see beneath that tiny skirt.

"I think a little bit of foreplay is in order first though." Her voice jerked his mind back to the present from his ogling of her perfect rump. She pulled on his tie still in her hand and again he almost stumbled as she drew him in close. So close he could feel her breath, smell the brandy in the glass, see what was amusement and what he hoped was want in her smoldering eyes, "Do me a favor, Jason. Reach between my legs and tell me if I remembered to put on some panties."

Oh, boy. Oh, shit. Jason nodded, not trusting himself to speak. What would he even say? Sure thing? You got it? All of that just seemed stupid. But it didn't matter. He reached down and rather than go right for her sex, ran the fingers of his hands up the corresponding thigh. "So smooth," he murmured. Any second now he'd find her-

His eyes went wide. "Oh, damn. I, uh, I think you forgot." The teen had thought she was teasing but there was no doubt that the fingers of his right hand were now sliding up and down the damp lips of her bare pussy.

At the feel of fingers she groaned out, "Good, then they won't be a hindrance to you." She took the coffee mug of brandy and lifted it to sip. "You have four minutes to use your fingers to get yourself acquainted with my pussy, or if I finish my brandy first."

"Take your time," he said and then kicked himself. Say something sexy or cool, not that! But he shook the thought aside to focus on her sex under his fingers. Jason pressed his fingers against it as he moved in long strokes from the wide base to the peak, counting out to thirty in his mind. God, she felt so smooth! And so warm!

He spread her labia with his left hand and the fingers if his right began to explore. They slid over her pinkness, teased her entrance, gliding over her folds. He started to search with them, seeking out the nub of her clitoris. Jason had read and watched "How to's" about pleasing women and he knew that even a virgin like him could give her pleasure when he found that. His index finger ran over a fleshy bump under a small town fold. Was that it?

He started to rub and press on it, trying to gauge what he was doing based on her body, her reaction. He took two fingers of his left hand and probed at her entrance before sliding them inside with a gasp. "So hot inside," he marveled. He started to move them, remembering the display she'd given him earlier today and trying to mimic her movements.

IC: Cassandra Delacourt

She pulled on his tie still in her hand pulling him in close so her lips and his were breath's distance apart, "Do me a favor, Jason. Reach between my legs and tell me if I remembered to put on some panties."

He nodded like an eager little puppy. Then he bent down and Cassandra felt his fingers slide up the inside of her thigh.

"So smooth," He murmured as his fingers journeyed up up up to underneath the hem of her dress and the juncture of his legs. She kept herself from giggling aloud when Cassandra saw his eyes go wide as those fingers discovered that she had indeed forgotten to wear underwear this evening.

"Oh, damn. I, uh," He stammered out as tentative fingers traced over the shaved-bare lips of her pussy, "I think you forgot."

At the feel of his fingers she groaned out, "Good, then they won't be a hindrance to you."

She took the coffee mug of brandy and lifted it to sip. "You have four minutes to use your fingers to get yourself acquainted with my pussy, or if I finish my brandy first."

"Take your time," Came his reply with an adorable wince at how corny that had sounded to him.

She lifted the mug to her lips and sipped leisurely as he bent down to use both hands. She felt his fingers trace up and down her sex for thirty-seconds or so. He was being slow-bonus points for that.

To Assist him she lifted one foot and rested it on one of the rungs island's bar stool beside her spreading her legs and giving Jason more room to work in. She took another sip of the brandy.

One hand then spread her open. The other used fingers tentatively explored the mysteries to him of a woman's vagina. She could feel him searching, seeking. She could guide him of course. She could tell him where things were. She could show him just how to touch her pussy the way that would send her skyrocketing into the land of bliss, but instead she only continued sipping the brandy in her coffee mug. She wanted to see Jason learn on his own. She wanted to see how fast he could pick it up too.

Finally his finger stumbled across her clitoris and she gave a splutter on the brandy she was in mid-sip on. The mug hung in her hand and she murmured, "...Mmmm...Right there..."

He started to home in on it, pressing the pad of his finger over it and rubbing across the top.

Cassandra leaned back against the kitchen island and undulated her pelvis forward with the motions of his fingers, trying to press into his touch for more pleasure. Then when his other hand pushed two fingers inside of her she gasped and moaned out loud. "Ohhhh...yes...right there..."

"So hot inside," He said in a voice full of surprised awe, and then began to pump them inside.

"...Mmmm...you're a natural at this, Jason..." She moaned out putting the mug down before reaching down to take his chin and lift his face up to look her in the eye. "Two minutes left."