tagFirst TimeThe Bet

The Bet


It was Thanksgiving and Caroline was jogging in the park. She had turned eighteen the day before, her parents were throwing a big party that night, she finally had her license and she had a nice boyfriend. Though he had come on a bit strong last night, she remembered, as though eighteen was the magic number and she'd dive into bed with him. She liked him well enough, but wasn't really ready to start an active sex life. Interested in starting one, yes, but not just jumping in because she'd turned eighteen. "Let him wait while I sort my feelings out," she decided.

She heard feet approaching from behind and glanced around. Another jogger coming up from behind. She'd seen him around, actually knew him slightly. His name was Ashleigh and he was considered a bit of a brain. She'd never seen him out jogging before.

Ash pulled up beside Caroline and fell into step with her. Noted the irritated look she gave him as she increased her speed to draw apart, but only grinned and matched her pace easily. The next look had changed from irritated to a glare.

"Stupid oaf. What's he thinks he's doing?" fumed Caroline. "I do not need some guy hitting on me while I'm jogging."

"Back off, please," she requested, determined to keep civil if she could.

"You're Caroline aren't you. You turned eighteen yesterday and your boyfriend is Brad. Just wanted to wish you a happy birthday and ask if Brad has won his bet yet."

Caroline felt confused. "Bet? What bet? And why should she know if he'd won it or not. Only one way to find out," she decided.

"What bet, and why would I know or care if he's won it. He gambles too much anyway, and I wish he'd stop."

Ash seemed confused. "How could you not know?" he asked. "It has to be you so you must know the details, surely?"

"Still don't know what you're talking about. Can you give me some details?" she asked, getting irritated by this idiot.

"The fucking bet, OK? Ah, pardon my language, won't you."

"You're still not making any sense. And I don't mind the language so what fucking bet are you talking about? Do you think you can explain in plain English?"

"You turned eighteen and today is Thanksgiving. Yes?"

"Ah, yes?" Caroline was definitely puzzled, but a little squirm of anxiety was niggling at her mind.

"You know Brad bets with, Hymie? Runs a tab there?"

"So I've heard," she replied, disapproval plain in her voice.

"Well, I was just wondering if he has managed to win his bet fast enough to win the full $50,000."

"He's bet $50,000," she screamed. "What does he have to do to win that and how am I involved?"

"Off course he hasn't bet $50,000. He's got some good odds, but the payout drops a thousand a day from now to Christmas. If he doesn't win by then he loses and has to fork out another $5,000 on top of what he already owes Hymie. He arranged it as a sort of holiday bet. Hymie's a sucker for holidays. He reckons they earn him a mint."

"BUT WHAT IS THE BET?" Caroline asked, through gritted teeth. For someone reputed to be smart he could sure talk a lot without getting to the point.

"I told you. The fucking bet. He has to pop your cherry before Christmas. The faster he does it, the more he wins. He reckons he's on a sure thing."


"There are a few side bets going amongst some of his friends, I believe. They're offering odds on when he scores. That's why I was asking. I know some of the guys betting and was just wondering if there were any winners yet."

"And," asked Caroline, in a gentle voice, "just how will they know when he's won? I can't see Hymie taking his word for it."

"He's got that covered," came the cheerful reply. "He'll be taping it and he only has to show Hymie the video. Hymie says if the video is good enough, he'll buy that as well."

"Are there any other bets floating around?"

"Some tried to bet on your virginity or lack thereof, but no takers. Everyone reckons you are."

"I see. What if someone else pops my cherry, as you so delicately put it?"

"Your boyfriend loses big time, but I can't see him admitting that someone beat him to it. Some ketchup on the sheets would cover that eventuality I suspect."

"And if he doesn't get to pop me at all?"

"He will. Guaranteed. Says he will if you agree or not on Christmas eve, because he's not losing that money due to your squeamishness. You'll take it and like it, he says."

"Why are you telling me this?" Caroline asked.

"Just curious. I know he was hoping for a quick win. He needs the money."

"What for?"

"Pay Hymie what he owes of course. If you hold him off to Christmas he'll barely clear what he owes. To make money he needs to fuck you as soon as possible. If you're going to do it, you should do it quickly. He'll owe you one and he'll have cash in hand for a nice Christmas present for you. Anyway, has he won yet or not?"

"No, he hasn't, and I don't believe a word of what you say."

"Ask him. See how he reacts. I surprised he wasn't strong-arming you last night."

Mentally reviewing the hard come on from the previous night Caroline asked "Why have you told me this?"

"Truth? I like you and I think Brad is an arsehole. It's only fair that you should know. But don't get the idea that he's only trying to sleep with you for the bet. The real prize is you. I'm sure the bet is just the icing on the cake."

"If what you say is true, which I doubt, it's pretty rich icing. Go away."

Ash nodded goodbye, and increased his pace, leaving behind a rather worried Caroline. She'd watch and see how Brad acted at the party tonight.

- - - - -

The party was a hit. Brad was there, more loving than ever and Ash wasn't. It was strange how she could so easily picture him in her mind. For someone who was supposed to be a brain he looked as though he'd strip well. Caroline realised, what she was thinking and flushed. He was a creep and a liar and Brad was her boyfriend and he hadn't left her side since the party started. Now that she thought about it he seemed to be all around her, keeping her almost exclusive company and he kept trying to draw her away from the party for what he called a little loving. Maybe she should go off with him for a few moments for a few kisses. She'd just have a word with her mother and then fade out for five minutes.

Brad was satisfied. Caroline was indicating that they'd head into the house for a few minutes. Once there, a few kisses, and she'd soon be ready. Question was, take her now and leave filming until tomorrow when she'd be more pliant, or coax her over to his place tomorrow and tape the actual popping? Take her now he decided. That way I'll get laid twice.

Caroline headed into the house, her destination the front room, which was relatively private. Brad was trailing along as expected and she turned to meet him as he followed her into the room. Before she could say anything, he was kissing her, hard, using all his considerable skill.

"He's seems to have had a lot of practice," came the uncharitable thought. "Odd. I normally enjoy his kisses."

She felt his hand slip quickly down to her breast and start to squeeze. She tried to push it away, but Brad wasn't complying the way he used to. "Stop being silly," he told her. "You're eighteen and I'm your boyfriend. This is what adults do." She struggled harder, getting scared now, but found Brad was a lot stronger than she had realised and had no intention of letting her go. His mouth was grinding on hers, and his hand had now dipped down to grope at her pussy.

Caroline struggled harder, but was greatly relieved when she heard her mother calling her from the hallway. Brad backed off abruptly, wishing the woman to the devil. "What possessed her to come looking for Caroline now," he grumbled to himself, little realising that the quick word Caroline had had with her mother was a request that she do just that. That little niggle of doubt raised by Ash had caused her to take precautions.

"Sorry, Brad, I have to go," she murmured politely. "Looks like you won't win the bet today either."

Brad's face flushed, and his frustrated fury was easy to see. "I don't know what you're talking about," he snarled.

It was evident that Caroline didn't believe him. "Your holiday bet with Hymie, remember?"

"Ah, sweetheart," Brad murmured. "I don't know what you heard but the bet's not relevant to us. I love you. I just wanted to show you how much."

"By raping me? It's not happening today, sport, and not ever as far as I'm concerned."

Caroline stalked out and back to the party, pointedly ignoring Brad for the rest of the night, and wondering what the hell she should do. She suspected that Brad was fully capable of raping her to win his bet, but who would believe her? He hadn't actually done anything yet.

She tried to calmly consider her choices. Bed the bastard so he wins his bet and will leave her alone. Wasn't going to happen. Don't bed him but chance getting raped if he gets desperate. Break off publicly, but that still wouldn't stop him if he decided to rape her. Sleep with someone else, but who? A picture of that grinning buffoon Ash popped into her head. She promptly shook it. No, not even if he did have a cute bum. "Which I did not notice when he jogged away," she told herself firmly.

She decided to go jogging again next morning. Maybe she'd meet Ash and he'd have some ideas. ---------- Caroline jogged round the park, hoping to hear someone coming up from behind. She needed to talk to someone about that stupid bet and what she should do. What could she do?

She was relieved when she finally heard that extra set of footsteps, then she faltered for a moment. What if it was Brad? She was alone out here, she realised. She flicked a glance over her shoulder, to see Ash approaching with a smile on his face. She smiled and faced front as she sensed him catch up and fall into step beside her.

They ran for a while, relaxing and enjoying the exercise.

Ash was the one to finally break the silence. "Found out the truth?" he queried gently. "What are you going to do?" he continued on receiving her dumb nod.

"I'm not going to sleep with him, that's for sure. I think the bastard would have raped me last night if I hadn't taken some precautions. I don't know what I'm going to do now." The last came out with a small catch in her voice, which she hated but couldn't entirely prevent.

"I live just over there," Ash said, indicating a house on the other side of road. "That's why I find it so convenient to jog here. Listen, you need to talk and it's too awkward trying to discuss something like this while you're jogging, or even strolling in the park. Why not send a message to your parents telling them where you are going and then you can come over to my place and talk."

Caroline considered the suggestion. As long as she let someone know where she was and who she was with it should be safe enough. Ash seemed a nice enough person, intelligent and friendly. Caroline suddenly found that her trust in her own judgement was shaken. Brad had tried to sucker her. Was Ash the same? Still, the SMS to her parents was his idea, and he wouldn't have suggested it if he meant her harm, would he? "She really needed to talk," she decided, "so she'd have to trust him. And be careful."

They crossed the road and were very shortly in the front room of Ash's house. Caroline looked around curiously. "Not bad," she thought, taking a quick drink from her bottle, moistening a mouth that seemed a little dry.

"It's a nice little place," said Ash. "I inherited it from my grandfather. I moved in a year ago. Haven't got around to making any changes yet, but it's on my to do list." He reached out and took the water bottle she was holding and placed it to one side. Then he reached out, drew her over and kissed her. Not demanding. Just a gentle brush of his lips on hers, then standing back again with a smile.

"Why'd you do that," Caroline asked, touching her fingers to her lips.

"Because I wanted to," Ash replied. "As a matter of fact, I want to do it again."

Not sure exactly how it came about, Caroline found herself sitting in Ash's lap, exchanging kisses. Gentle at first, but becoming increasingly more ardent as they both familiarised themselves with their partner. After a few minutes Caroline broke off, and leaned back against Ash's arm. "How did that happen?" she wondered. "But it was nice." It slowly registered with her that one of her breasts was comfortably placed in Ash's hand. He wasn't teasing it or squeezing, just cupping it and obviously enjoying the feel and weight of it. "He shouldn't be doing that?" she thought, but it did feel nice. She left his hand there, as the hand on her back pressed her gently towards him for more kissing.

Caroline barely registered the fact that her top and been pulled free from her shorts until Ash broke of contact, then lifted the top up, Caroline to her own surprise lifting her arms to let it go. She felt his hand unclip her bra, and was again slightly shocked at her own behaviour as she shrugged forward to let the straps slip off her shoulder. She watched as his hand moved gently over her breast, enjoying the feel of his hand gently soothing it, stoking and then rubbing the nipple.

Ash started kissing her again, and Caroline forgot about the hands that were now touching both breasts, teasing them and sending little ripples of excitement through her. It seemed only right and natural to her when he bent his head and his lips followed the path that his hands had been tracing. She gasped and turned suddenly toward him, eager to have his mouth suckle on her breasts.

She felt a sudden flush of wetness over the front of her shorts, and was startled, then shocked as it spread across her front, rapidly and coldly.

She sat up abruptly with a squeal, looking down to see a large damp patch that formed after she'd bumped her water bottle and knocked it into her lap. She jumped to her feet, plucking at the damp cloth trying to hold it away from her. She glared at Ash, who was laughing, and saw his eyes travelling over her, appreciating what he was seeing. "Oh my god," she thought in slow horror, face turning scarlet, "I'm half naked and the other half is on display thanks to that damned water bottle. This is all his fault."

Ash could see that Caroline was getting upset and hastened to reassure her. "Hey, don't worry about it," he soothed. "It's only water, it will soon dry."

"But if feels horrible, and it lets you see everything," she wailed.

"That's easy to fix," he coaxed. "We'll just hang them to dry, and I'll get you something to wrap around yourself."

Too her surprise, he reached over and undid the buttons on her shorts and started to slide them down. She gasped, and clutched at them, listening while his voice gently calmed her.

"It's OK. They're effectively transparent now so it's not like I'm seeing something new," he coaxed, feeling her fingers relax and letting him slide off her shorts. "These are wet, too, remember," he said and Caroline watched in dismay and quite a bit of unwanted excitement as her panties vanished, joining her shorts spread out on the side table to drive.

"I look ridiculous," she moaned. "I'm standing hear naked except for my jogging shoes. Where's the wrap-around you offered?"

"First things first," said Ash. "Like you say, just shoes is ridiculous." He reached down and slipped them off for her. "Now you want a wrap-around. And I want to kiss you again. I'd have to go upstairs for the wrap-around, but I can kiss you right here."

Hand against her back, she was drawn firmly back to him, protesting, but not resisting. The kissing started again, first at the lips but quickly moving down to her generous and sensitive breasts. Caroline found herself pressing harder against him, wanting more. Not sure what more she was wanting but wanting it any way.

Ash continued sucking gently on Caroline's breasts and nipples, rebuilding the earlier excitement, but now a hand was drifting slowly over her tummy, releasing little curls of excitement as it gently brushed her skin before settling on her mound and cupping it. Caroline gasped at that touch and pushed upwards, wanting a firmer touch which Ash was happy to give. Caroline could now feel his fingers playing, experimenting, squeezing here, gently stoking there, pushing between her lips to the moist interior, slowly igniting her passions, goading her to want more,

Caroline's own hands were wandering now, moving instinctively over Ash's body. Tugging his shirt loose and taking it off, regretting the loss of those hands touching her for the moment it took to remove the shirt, welcoming their return while her own hands were wandering over and treasuring Ash's bare skin.

Caroline could feel Ash's erection, pressing hard against her side, and found herself divided. Part of her wanted to reach down and touch it, another part nervously backing away. Her quandary resolved, when Ash reached down and pushed his shorts and jocks down, letting his erection spring up, into her waiting hand. Feeling his cock slap against her hand Caroline automatically closed around it, touching it, squeezing it, enjoying the feel of it and wondering what was coming.

Ash lifted Caroline off the couch and onto the rug in front of it. Laid her on her back while lying next to her, hands travelling steadily over her, leaving turmoil wherever they went.

Caroline was breathing hard, still holding and stroking Ash's cock, relishing the hardness and length, knowing she wanted this inside her. Soon. Her legs had automatically parted when he laid her down, and as she felt him move to position himself between them, she also felt her knees rising, spreading her thighs further apart, eager to give him all the access he wanted.

Ash gently moved Caroline's lips apart, slipping the head of his cock between them and then letting the lips close over him. He looked at Caroline, only to see that she was looking down at that point where his cock had entered her flesh, fascinated by the intruder that was now invading her, wanting to see it disappear into her at the same time as she felt rising slowly within.

Caroline could feel his cock pressing against her hymen, and gasped as she felt a sting as it broke, giving Ash free access to her deeper being. "He's popped my cherry," came the whimsical thought, "and I don't care. I like it and I want more."

She could feel him moving slowly in, a steady pressure that parted her vagina, stretched it, slipping through the moist flesh, seeking complete accommodation, which her body was only to anxious to grant.

Only when she was satisfied that he was fully embedded did she transfer her gaze to Ash's face, to see that he was staring at her and smiling in a teasing manner. She found herself smiling back, waiting for the real fun to start.

Ash slowly withdrew, lingeringly, teasing as he pulled back, only to return, finding Caroline rising eagerly to meet him. Not taking his eyes of her face he continued, pulling back slowly, but thrusting in hard and fast. Caroline held on to him, regretting the withdrawals, relishing the returning thrusts, enjoying the way his cock slipped smoothly over her damp and heated flesh.

Together, they sought and found the rhythm they craved, moving in unison, becoming one, feeling each others joy, rising steadily towards completion.

Now Caroline found she couldn't see him anymore, her eyes closing, the external world fading from around her, her entire being fixed internally where that beloved intruder was demanding and holding her attention. She gloried in the feelings that he was engendering within her, exulting in being a woman and pleasing and being pleased by her man. Because he was her man now, what they were doing was just sealing the fact. What came after this she didn't know and didn't care, but as long as this existed within her she was satisfied.

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byAshson© 14 comments/ 87011 views/ 13 favorites

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