Romantic Roulette 01: First Date

It took until her second to last year of working on her law degree to figure out the pattern. Some women figure out their type... their fantasy... early on, but not Jennifer - she was almost as much of a mystery to herself as the men that dropped in and out of her life. She'd fucked enough nice guys to know she didn't really care for it, but she'd shared her bed with enough bad boys, boy toys, dangerous deadbeats, and men ten years older than her. All of them had been fun, but only sometimes. It was only until after a guy she'd been banging casually and cumming hard for for a few months started being nice to her that she realized she no longer had any desire to see him.

In the time before nearly anonymous hookup apps, Jennifer would have been a pariah. She was a screwed up young woman with a diagnosable sex addiction, and had even gone to a a couple meetings once, but she had just end up fucking her sponser, so she had decided not to go back and drag other people down with her. She'd accepted that she was a nymphomaniac, and as long as her friends and colleagues never found out, she could live with it. Strange men might enjoy a slender little slut with dark hair and proud B cup breasts who had no desire for them to call her back, but everyone else, they were another story.

She had no trouble getting guys to bring her back to their place, but as soon as they started to catch feelings for her after a night or two in the bedroom, she was gone. If she couldn't find anyone with a particularly entitled pick up game on Tinder, she would just go to one of the local bars around campus and drink until someone tried to take advantage of her. Those nights were usually great, nothing made her cum like a random creep using a pussy far too drunk to consent. She'd long since lost track of her body count, but it was over a hundred. Her orgasm count was much lower at 27, and tonight she was going out in search of 28.

She knew as soon as she sat down at the restaurant that this guy wasn't going to be her next lucky number. He'd talked a good game online, but in person she could immediately tell he was a good person, if a bit edgy. She briefly considered whether it would be kinder to him for her to just leave before he bought her dinner, but a quick glance at the bar and her phone showed no other good options. It was this dick or no dick, and going home without fucking for the last two days would make tommorow just awful. So She stayed, and pretended to have a good time.

She reflected that if she wasn't so broken Dan would be a good boyfriend; He was smart, handsome, clever and attentive - if he had the dick to match he'd be the perfect guy. Halfway through the night she even stopped pretending without noticing, laughing along to his jokes as he tried to pry his way through her carefully cultivated shell with wit and humor. The worst thing a guy could do, besides being a decent human being to her of course, was to be boring. Boring guys told you how funny they were, instead of just demonstrating it by making you laugh. It was like a guy telling you handsome he was but refusing to show you a picture to settle the issue, Jennifer thought.

But then, when everything was going so well as the date was winding down, and she was actually starting to look forward to getting his clothes off, Dan killed the mood entirely. They were leaving the restaurant after he had offered to drive her home, and walking towards his car when he suddenly turned to her and asked if it would be okay to kiss her. Consent was all the rage these days, but nothing made her dryer than a man who didn't just take what he wanted. The last thing she wanted was a sweet man more concerned with consent than in fucking her like a rag doll, so her kiss back to him was mechanical, but he didn't seem to notice. On the way back he finally turned to her and asked, "So what did I do to ruin the night? You really seemed to be into it, but now... Now you're just quiet."

"Does that happen to you a lot?" Jennifer said, answering his question with a question."

"Yeah, actually it does," Dan responded, running a hand through his dirty blonde hair as they drove across the nighttime streets. "How did you know?"

"Let me guess," She opined, "The silence comes right before they tell you how nice you are, and how you're a great guy.. Maybe even an occasional 'it's not you, it's me, right?"

"So are you a mind reader, or did you just hack my tinder?" he joked, glancing at her as traffic permitted.

"This is just my way of telling you that just because women say they want men to be kind and sweet and chivalrous in every book, and on every show, maybe they don't really want that from the right guy." Jennifer said, rambling a little after three drinks. "Think about it. There's a lot of ads out there telling you how great this drug or that deoderant works, but no one needs to tell you that cocaine works great or Porsche's are fast. No one needs to convince you that true things are true."

"So you're saying women don't want romance and cuddling then?" Dan asked skeptically.

"Sure they do, I think... not me, but most of them." she hesitated, trying to think of the best way to phrase it, "just not during the part where they want to fuck. Most women want romance before and kindness after.. But in between they want a little force and danger, and well... and well, danger isn't exactly your middle name."

She wasn't trying to make him mad, and normally she would never have this conversation with a guy in real life, but the dark car and the booze made it almost seem like another incel she was arguing with online, and as a broken slut, Jennifer was perfectly comfortable with those sorts of flame wars she had in between posting pictures of her tits while she looked for her type of man. But there she couldn't see their knuckles turning white as their grip on the steering wheel tightened, and she also couldn't see the speedometer slowly rising to match the frustration of her audience as her advice clashed with a lifetime of every woman in his life just telling him to be himself.

"Maybe you should slow down," She offered helpfully "Before you get..."

"Maybe you should shut the fuck up," he countered, not even looking at her. "If you let a guy buy you dinner, then you should know that telling him to stop being a bitch isn't the sort of thank you he's looking for."

"No," she agreed, an edge of cruelty in her voice. His fragile ego wasn't her problem. "It isn't. Usually they at least want their dick sucked, but you'll never know because you asked if you could kiss me instead of telling me you were going to cum down my throat."

"So that's how easy it is?" Dan asked incredulously, coming to a stop at a red light. "I tell you to deep throat me and you just do it?"

"Well, yeah, sometimes," Jennifer answered too honestly again, before hastily adding, "but not now, because I just can't see you that way now."

"Oh yeah," he asked, "and how would I fix that, with the next girl I mean, since you were clearly a waste of my time."

"Well, stop being yourself and start being a fucking man, mostly" she answered, growing increasingly annoyed by his petulant behavior. "You just need to... Ahhhh..."Jennifer moaned as he reached over, grabbed a handful of her hair, and pulled her head back.

"Listen slut, I'm sure you're trying to be helpful, but at this point I dont want to hear another fucking word until we get back to your place. Got it?" He asked it like a question, but it was the first thing he said all evening that had the aura of command to it, and it resonated with Jennifer. She still wasn't going to fuck him, but if he had done this before she had had to explain the facts of life to him and ruin the whole thing he definitely would have gotten laid a couple times before she got tired of him.

"Yes, I..." She started to answer, but he didn't give her the chance. She hadn't noticed that while he'd been pulling her hair he'd unzipped his fly and pulled his dick out, but when she started talking again, he grabbed her hair and pulled her head forward, towards his lap, forcing his 6 inch cock in her mouth just as he started driving again.

"What part of shut the fuck up don't you get, bitch?" he asked, holding her head down while she struggled briefly to escape this sudden turning of the tables. "Did your mother ever teach you that if you don't have something nice to say then suck some fucking dick instead?"

Jennifer was conflicted now. She didn't really want to fuck him, but what he was doing was kind of hot. Maybe this evening didn't have to be a total waste afterall, she thought, as she ceased her struggles and started to bob up and down on his cock instead while her date resumed driving slightly more erratically than before. "I'll tell you what cunt," he growled while he drove, "We've got four or five minutes before we're back at your apartment. If you can make me cum down your slutty throat by then, then I won't go upstairs and rape your pussy in your own bed. That's as fair of a deal as you're ever going to get.What do you say?"

She neither agreed nor disagreed with his offer, she just kept sucking his dick, swirling her tongue around the glans in long lingering strokes before attacking the frenulum with a frenzied intensity. She didn't want to suck this guys dick or fuck him. Not really. Either would be more fun than trying to explain to him why he wasn't her type again. What she really wanted was to be so distracting he got into an accident. That's what she pictured while she bobbed her head up and down on his cock; this little bitch losing control of the car when he came down her pretty little throat and getting in a fender bender with the car in front of him, leaving her free to run off. That would be the perfect end to the perfect evening.

But she wasn't successful, whether by luck or determination he held out until they pulled up at her place and parked. He pulled her head up and kissed her forehead then. "Good girl." he said, "But not good enough."He almost sounded like he meant it, she though "Now why don't I show you what happens to sluts that don't know how to suck dick good enough to make me cum?" Jennifer considered her options then. She could just tell him no and he would probably give up like the bitch he was, she could head butt him and run off, or she could lead him back to her room and roll the dice. On any other day she would have told him to fuck off, but she was aching for some dick, and tonight even some mediocre nice guy cock would probablly scratch her itch until she could find something better in a day or two.

Finally, she shrugged mentally and kissed him hard on the mouth, enjoying the way he recoiled slightly. She knew he was the type of guy that would hate to be kissed right after she sucked his cock; she just had a sense about these things. "Lead on Romeo", she whispered after she pulled away, wondering how long he could keep up his tough guy act. They made out in the elevator on the way up to the eighth floor. As soon as the doors closed he pinned her hard to the wall, mauling her tits, biting her neck, and groping her ass while she whimpered and felt the unexpected ferocity having its expected effect on her perverse body; for the first time all night she started to get moist as her lips engorged at the idea of being used against her will.

Once they got in her studio, she put up a bit more of a fight, struggling with him and trying to fight him off as he tried to get her dress off of her. Eventually he flipped her over and pinned her arm behind her back. She thought he was giving up and taunted him, "What's the matter, tired of having to put in a little effort already? You were doing such a good job of faking it until now." That's why he grabbed her phone charging cable from the wall and started tying her wrists together behind her back.

"Done?"He laughed, "Bitch we're just getting started."

Now she was getting close to helpless; part of her regretted letting it get this far, part of her rejoiced that it had. It was the usual conflicted dance her warped psychology started to perform when she was really having a good time. Then with a sudden tear, he grabbed her thin cotton panties and ripped them off, leaving her feeling suddenly exposed.

"MMMmmm," Jennifer bit her bottom lip to stifle a moan. "Well aren't you full of surprises Danny, just remember to wear a condom before we see if your stamina in my pussy can match your stamina in my mouth."

"Oh, so you bitch about how you want to be out of control all night, and now all of the sudden you want me to listen to what you have to say?" he asked as he unzipped his pants and started to strip. "Well Jennifer, as some little cunt in my car pointed out earlier, that's not the way this works."

Jennifer felt her heart skip a beat. She might be a slut, but she was a safe slut, and as hot as raw sex could be the last thing she needed right now was another pregnancy scare. "Hey, asshole," she said with false bravado, "You want to play rough? Great, but play safe or go home and play with yourself.

His response was immediate. He took off his belt and started to wail on her ass with it. Whack, whack, whack... stroke after stroke of liquid pain suddenly assaulted her. He didn't stop until at least a dozen - not until she cried out and lost count, but the message was read loud and clear. He was putting her in her place, and it was working. After a brief pause he knelt down next to her and forced her face into the mattress, muffling the noises she was making, and then started again with the belt. Last time the blows came from above and mostly hit her ass. This time they came from the side, wrapping around from the angle and making the doubled up belt sting more at the end. Thwack! Whack! This time she couldn't hold back the cries of pleasure and pain... not just because she was sensitized to the feeling now that he was hitting some of the same places he had already hit, but because most of the blows were landing on her muscular thighs, and they were far more sensitive than her ass.

Finally, after her body was covered in a sheen of sweat from the exertions of trying in vein to get away from the pain, he let go of her head, letting her breathe properly and take great heaving lungfuls of air. "Please," she said finally, practically whispering it, "Please use a condom when you fuck me. Please. Today isn't a very safe day, and if you cum inside me I'll never finish school. "

He stopped what he was doing to her and spent a long moment doing something behind her, where she couldn't see. Finally he put a condom in each one of her hands. "I'll tell you what cunt. We'll leave it up to chance. Heads I use the condom I put in your left hand... tails I use the condom I put in your right, and we'll let the flip of a coin decide the rest of your life."

"But why should that..." she started before he interrupted her with a swift smack on the ass.

"Because I borrowed a pushpin from your wall here" he said as he tossed it on the bed where she could see it, and I poked a hole in one. The other is fine... but you won't know which one I used until you get your next period in a week or two... or until you don't get at all I suppose."

He laughed then, and she heard the sound of a coin being flipped in the air, landing tails near the pushpin. Jennifer's blood ran cold at the thought of what was about to happen. She felt him take the left condom and toss it away towards the door, then he took the one on the right, ripped it open, and started to put it on.

"Wait," she said, "This isn't what I was looking for, you can't bet my whole life on the slip of a coin."

But he ignored her, lifting her hips as he got ready to mount her vulnerable body from behind. She felt him pressing against her needy little pussy then. She might not want this, but her cunt certainly did. Between the bondage, the force, the pain, and the risk of getting knocked up, it was as wet as she could remember.

"I just wanted to take a nice girl on a nice date," Dan said as he started to slide inside her defenseless hole, "But a fucked up slut like you showed up instead... and a fucked up whore needs some fucked up games if she's going to get off, doesn't she?"

Jennifer's mind raced, trying to decide if she would get better results by begging for her lover to take pity on her or by demanding he see sense, but she didn't have the chance to do either, because the moment he slid his dick inside her tight little cunt, and bottomed out inside of her, she lost all ability to think. Instead all she could do was feel as he started to fuck her. Every thrust ended with a little gasp or moan escaping her lips, and the faster they got, the closer they got together until she was nothing but a bitch in heat issuing constant noises of pleasure as she was used for his pleasure.

"That's right cunt," Dan growled as he held her hips and pounded her pussy hard and deep, "You said you wanted safe sex, but we both know you'd rather I used you like a rag doll. Maybe I should just rip this condom off and claim your womb with my cum. How would you like that?"

Jennifer didn't respond with words, but the increased volume of her moans and the way her pussy clenched down on his dick made the idea very clear: her conscious mind might not want it, but her animal needs craved it. Dan just laughed at this response, slapping her ass for emphasis. "Maybe next time slut. I'm enjoying this game far too much right now. How does it feel? You have a 50% chance this is another meaningless fling and a 50% chance that tonight will change the course of your whole life." Jennifer gasped again, shuddering at the idea as a thrill of pleasure went down her spine and straight to her pussy. "What do you think, cunt? Do you think you'll be a good mommy? Do you think you'll be able to find weirdos online that want to fuck a prego slut when you start to show that can hurt you enough to make a twisted doll like you cum without hurting the baby? Or will those pregnancy hormones turn you into a complete nymphomaniac that's completely unable to be fulfilled by anyone, no matter how long the train is that they pull on your ass? Wouldn't that be fitting punishment for being the broken bitch you are now."

Half of what Dan said to her as he fucked her didn't even register. Jennifer's breathing was ragged and her mind was clouded by the pleasure being inflicted on her. What little ability to think that remained was devoted to imagining herself 8 months pregnant... her belly swollen, her tits leaking. She couldn't help it. It wasn't ever something she wanted, but in this moment all she wanted was for this stranger to breed her. "Please," she whimpered, "Please don't..." Neither of them knew what she was going to beg him not to do, because before she could finish, her rising orgasm detonated inside of her, making her shiver and shake like an epileptic as she writhed in pleasure to those terrible fantasies.

Dan was only ten or fifteen seconds behind her, and as he came, he bottomed out inside her, and blasted away with spurt after spurt of hot dangerous cum while he collapsed on his lover and pulled her hair so he could whisper into her ear, "Get fucking pregnant, slut." They lay there for more than a minute like that before he pulled his dick out of her. Then he sat up, removed the condom, tying it off and tossing it aside before he undid her arms, and held her close while she shivered in his arms.

"Will you tell me which condom you used now?" she said after a few minutes of enjoying the comfortable silence in Dan's arms while he casually groped her left breast. The afterglow was only now receeding enough that she could think coherently again, and she was surprised by how she felt after the experience. The fear and anticipation she expected, but how horny it made her... that was something else she hadn't known about her. She almost wished he'd fuck her again right now. Jennifer didn't even care if he wore a condom, because then at least she would know. This uncertainty was somehow worse than feeling cum dripping out of her cunt. Had some sperm been left in her womb? Were they looking for her egg even now? Was...