Romantic Roulette 02: Second Date

Jennifer seriously considered blocking his number the next morning. Despite the wonderful job he'd done in bed, she was sure it was all just an act, and that if she let him get her naked again, his inevitable failure would only retroactively ruin the memory of their first night together. After a day of classes and a night without any promising new suitors on any of her dating apps, she reconsidered Dan again, despite her misgivings. After another day she was honestly surprised she hadn't heard from him, and decided to text him.

'What if I'm not free next weekend?' she sent.

An hour later she got her response, 'Then I guess you'll never know.'

She found his distance both surprising and annoying. Why didn't he want to see her more? He'd been awfully into her the other night, but now he seemed almost bored of her.

'I can do tomorrow or Thursday night,' she responded finally after deleting a couple messages that came across as too needy. There was no way she could last until Friday night without fucking someone; she'd be a wreck.

'What's the rush? I can do you anytime I want.' Came the response a few minutes later. Jennifer looked at in annoyance before closing her messenger and opening up her browser to watch some porn instead. She didn't need to put up with this shit. She could find someone else to fill and fulfill her. But after playing with her clit to a couple videos showing some professionals doing a bad job of pretending to be amateurs being violated against their will that were still totally and unrealistically into it, she put her phone down. It wasn't doing anything for her.

Instead she tried to remember the other night with Dan. Not the first half where he was useless. No, just the part after he'd tied her up and played that awful game with the condom. She called it awful, but she'd thought about it every day since then. Even now thinking about the fact that he might have cum inside her made her needy pussy tingle as she fingered it. So she went with it. In her version of the night though, he was rougher. He tied her up tighter, he used her harder, and at the end, when he came, the shredded and useless condom he was wearing didn't stop even a little bit of his dangerous cum as he painted her insides white while she begged him to pull out. That image made her cum hard in her bed, but as the orgasm faded, she realized for the thousandth time that all it did was make her craving for dick even worse.

Jennifer decided to change tactics, and after removing her clothes and artfully staging her panties and a vibrator on her bed, she took a few nude selfies. The way she twisted her body at the waist, showed very little but promised the world to a horny guy. Then after she spent a few minutes picking out the best one and cropping out her face, she sent it to Dan with the message 'Sure you can. You and everyone else.'

A few minutes later she finally got the response she was looking for. 'I have to work, but if you're craving dick that badly you can come over tomorrow night at 7. I'll make you dinner and then devour you for dessert.' The text came along with a pin for where he lived, and Jennifer smiled despite herself, not bothering to answer. Instead she switched gears to her homework, trying not to get her hopes up about her second date.

Wednesday dragged, but eventually school ended, and as Jennifer got out of her Lyft, she admired the row of modern townhomes. Clearly Dan made a decent living; that explained a lot to her. Guys that made that much at his age were usually tech geeks that were beta as fuck. She usually couldn't stand that type, but she'd make an exception for him. He was worth at least another date or two. She walked up to the door and knocked, wearing her sluttiest pair of heels and a little black dress with nothing on underneath. Jennifer wanted to do everything in her power to make her date skip dinner and go straight for dessert.

When he opened the door, looked her up and down like she was a piece of meat, and then walked back to the kitchen, she realized she probably wasn't going to get her wish. Whatever he was cooking smelled amazing and he quickly ignored her as he returned whatever crucial step he'd left to answer the door.

"Make yourself comfortable," he remarked disinterestedly as he added shrimp to his alfredo sauce, "There's a bottle of chardonnay on the table if you'd like a glass."

Jennifer ignored the wine for the moment, taking in the space. It was new and high end, with a loft, cathedralesque ceilings, exposed beams, granite countertops, and tasteful fixtures. It was a beautiful place that was only partially ruined by his taste in severe modernist furniture with it's dark fabrics and faux walnut everything. But except for the nerd art on the walls, it was fine. She looked from one picture to the next but couldn't decide if it was from Star Trek or Star Wars; she always got those confused.

"Nice place," she said finally, sitting down at the dinner table facing him in the kitchen so that he'd be able to see she hadn't bothered to wear panties when he looked over.

"Thanks," He said, emulating her flat tone, mocking her. "Maybe next time you give me a compliment, you'll actually mean it."

A frown flickered across Jennifer's face briefly when he didn't look up. "Oh, I meant it. The building is great, it's the tastes of it's occupant that could use a little work."

"There's the Jennifer I remember from the other night," Dan smiled as he started to plate their meal. "So did you decide you liked me enough to give me another chance, or were all your other booty calls busy?"

"I figured that after you were such an asshole the other night, I would let you try to make it up to me," she turned to hide her smile and poured herself a glass of white wine. "Not that I expect you to succeed of course."

"Of course not," He said, carrying over plates of shrimp alfredo, steamed vegetables, and garlic bread over to the table. "How could I possibly succeed against a forest of hidden tripwires and unknowable land mines that is your psyche."

She glared at him for a moment before she smiled to hide her annoyance and then changed the topic, "Wow, this actually looks pretty good. I didn't think any guys knew how to cook in the era of Doordash and Ubereats."

"What can I say?" Dan asked, "I knew how much you loved hot creamy sauces, and I just had to make sure you got your fill."

This time Jennifer actually smiled. This was the reason she'd decided to see him again. Because his dick aside, he could infuriate her in all the right ways. "So tell me," she asked after a few bites, "Which condom did you end up using to fuck me the other night? The good one or the ruined one?"

"Say please," Dan admonished her, before taking a sip to watch her squirm.

Jennifer thought up and discarded several jabs she would have enjoyed making if they wouldn't have been so counterproductive. "Please tell me which condom you used." she mumbled at last, allowing her annoyance to show, but not too much.

"The only thing I ruined the other night was your pussy," Dan said finally, taking pity on her. "It was just a game to spice things up. You've got nothing to worry about." Jennifer smiled at that answer, feeling more relief than she expected. She wasn't at risk anymore. They enjoyed their meal together, trading witty barbs and retorts for the next hour while they drained their bottle and started another. It was certainly better than their last dinner together, and long before she'd cleared her plate she was mostly focused on how badly she wanted to fuck him.

Finally as he started to clear the plates he asked, "So, would you like to help me with the dishes, or would you prefer..."

Jennifer interrupted him as she stood up, "I was hoping we skip all the bullshit and you could just fuck me." As she talked, she let her dress's spaghetti straps slide off her shoulders, letting her dress slide off her body, fall to the ground, and pool around her fuck me heels. Dan watched her little show, took a moment to appreciate her perky breasts, shaved pussy, lustful expression, and then walked over to her and kissed her hard, groping her tight ass as he pressed his body hungrily against hers. She responded by reaching down to try to pull Dan's t-shirt over his head. When he stepped back and wrestled it over his head before tossing it aside, she began to unbutton his jeans, but as soon as Dan's hands were free he stopped her by grabbing a handful of hair and pulling her away from the dick she was aching for.

"Sorry to disappoint you cunt, but we aren't quite ready for dessert yet. There's one more course I want to serve first," Dan taunted before letting her go and picking up a coil of black silk rope from the couch.

"And what's that," she purred, obviously enjoying where this was going. Dan didn't respond right away. Instead he tied her wrists together tightly before he tossed the coil of rope over the beam in the living room, and then slowly pulled out the slack until she was forced to stand on her toes to keep the weight off of her wrists. Once the whole thing was taut he secured the loose end to the base of the couch with a quick release knot and then started to strip down to his boxer briefs.

"Next we're going to try a dish I think you're really going to enjoy," he said, walking out of her line of sight. "I call it pain and shame." A chill ran down Jennifer's spine at the idea. "Before I get started though," he said, rummaging through a bag of toys for just this sort of play, "Do you have any limits I should be aware of?"

"Mmmmm..." She sighed, "You can do anything to me you want as long as you wear a condom without holes in it this time, asshole."

"That's a fair compromise," he agreed walking up to her from behind so his voice was suddenly so close that it startled her. Jennifer opened her mouth for another biting comment, but as soon as she did, he reached around and put a ball gag in her mouth. He tightened the strap just as she got the idea that maybe she should try to prevent this before it was too late.

"That's for the neighbors," he said, mollifying her somewhat, "The sound insulation in these units isn't as good as I'd like it to be to hurt sluts like you properly.

Then he pulled a wooden implement out of his bag of tricks and walked back over to her, lightly tapping her ass with it as she tried to guess what it was, it seemed too small for a paddle, maybe it was... Jennifer's train of thought suddenly stopped when he suddenly pulled his arm back preparing for the first swing. But the blow never landed. "Silly me," he teased, "I remembered the pain, but I forgot the shame." He set his implement back down and then walked back over to her with his cellphone in hand. "We're definitely going to want some before pictures so we can properly appreciate how you look after."

Jennifer struggled against her bonds while she groaned and gurgled against her ball gag. She'd meant he could fuck her however he wanted, not this. She hated the idea that he was taking pictures of her in such a vulnerable pose. Well, most of her did. Her nipples hardened, and it suddenly felt warm in the cool living room. Besides the small part of her traitorous body that enjoyed the idea that someone else might see her like this though, the rest of her was outraged. That didn't stop him from taking his filthy pictures though. "Oooo, I love the fire in your eyes slut - that's great smolder." he mocked her, treating her like a model that might enjoy this sort of thing as he circled her, taking snaps. "Now show me vulnerability. Come on baby. I know you can do it."

After perhaps a minute, it was finally over and he put his camera away. Jennifer stared daggers at him as he smirked at her, obviously enjoying her anger; she was pissed, but she tried not to let it interfere with her enjoyment for what was coming next. She could always make him delete the snaps after he was done fucking her, so it didn't matter. But with his next words her certainty fell away. "We'll get started in just a second slut, I almost forgot to turn on the live stream." Jennifer practically choked on her ball gag in indignation. He wouldn't, would he?

Dan took no notice of her torment though, and walked over to a laptop on top of his entertainment center. He flipped it open, and with a couple keystrokes, he mirrored his screen to the large flat screen, letting Jennifer see exactly what he was doing. First he enabled a webcam, pointing it so that it had an excellent view of the front of her body from the neck down. Next he logged into some shady cam girl website and opened a chatroom titled 'PAINSLUT Gets What She Deserves.' Lastly he started the session, then he walked away leaving her to watch the empty chatroom, wondering if people would show up to watch her be tormented publicly like this. Jennifer lost it then, and started to struggle like a woman possessed. She tried to shout through her muffling gag, but even simple words like NO came out as garbled guttural sounds.

She quickly realized that she could do nothing to stop what was about to happen, which wasn't the worst feeling in the world. It was only when she saw the chat list starting to populate with random usernames that her heart sank. Strangers were going to see what a masochist she was, and she couldn't do anything about it. She didn't have time for self-pity though, because Dan chose that moment to announce his plan to his audience. "Thank you all for turning out on such short notice tonight, I've got a real firecracker for all of you today."

"Tonight's toy is a serious pain slut currently pursuing a law degree. That's right, she wants to be a servant of the court by day but she's happy to be the servant of any cock that's interested by night. Her turn ons include: pain, unprotected sex, and any man that's willing to hold her down and force her legs open. I give you..." Dan paused for dramatic effect, and at that moment Jennifer wanted nothing more than to curl up and die. Last time this man fucked her he almost ruined her life with a baby, and this time he was going to tell everyone exactly who she was and ruin her career before it even started. It was monstrous. "... Marci the Masochist!"

Jennifer's internal sigh of relief that she was being given at least a fig leaf of anonymity, was short lived. As soon as Dan finished talking, he brought the wooden spoon he was holding down on her ass hard. Once. Twice. Three times. Each blow landed in a slightly different spot on her ass and made her thrust and gyrate away from it to try to escape it. "Now for regulars to my streams, you know the rules: before we can get to any of the real fun I've got to break this cheap wooden spoon on a bitches behind, so let's get to it."

Wait, he'd done this before? He did this often? With other girls? If this guy was such a freak then why had he come across as a nice guy on their first date? She didn't have time to ponder any of these questions though, because the blows started again. They came faster this time, and each one was a little harder than the last. Due to the speed of his blows, her tormentor only called out every fifth stroke.

"Five!" her ass was just starting to ache.

"Ten!" Her butt felt like it was on fire now.

"Fifteen!" She'd stopped trying to avoid each stroke now, there was no point.

"Twenty!" Jennifer was panting now. She wished she could say it was because of how much it hurt, but she was getting turned on more than she'd admit to anyone, let alone the asshole that was showing her agony to the world.

"Twenty Five!" She was sure that if she had a cock inside her, or even a toy she'd be able to cum right now. When she got this turned on, the wires started to cross somewhere deep inside of her, and all the pain she felt became a different flavor of pleasure.

"Thirty!" She was grateful for the ball gag now, because she was mewling and moaning constantly. If she had to be shamed publicly, at least she could hide this part of it from them.

"Thirty five!" Jennifer was a mess. Her pussy was soaked, and she was sweating. Though it felt like he'd been doing this forever the count assured her it hadn't even been a minute yet.

Dan never got to 40. The spoon finally broke on stroke 38, and he walked up to the camera holding both pieces. "Well folks," he chuckled, "that's what you get for 48 cents when you buy something made in China. I'd say that maybe we'll go for a better brand, but really, these cheap sluts don't deserve anything better, do they?"

He walked back to Jennifer, and met her glaring with a smile before he turned her around so she was facing away from the TV. "This next one though - I know you're going to want to see her." Now that she was turned around she could no longer see the constant scrawl of messages scrolling along the screen, but she could see Dan picking up a long thin cane which he brandished menacingly. Jennifer hadn't been struck by one of those in a long time, and she shrank from it, recalling how much they hurt, or tried to at least. As he walked behind her she tried to spin to avoid him, but he whispered, "careful slut, if you move and I hit one of your sharp hips instead of your padded ass, you'll regret it."

Jennifer did the only thing she could do, she froze. As her tormentor walked back in front of the camera and asked his audience, "So, how many strokes shall we give her with this." He waited for answers to scroll by before adding? "Ten? That's far too many. I want to fuck her after this, not bandage her. Four? Four sounds good. Do you like the sound of that Marci?" Jennifer shook her head violently as he walked back to her ass. "Perfect," he said. "On three then. One! Two!" He brought the cane down hard on her upper thighs without ever uttering the word three. For a moment it felt like there was no pain at all, but then just as he was bringing it down for the second time across her ass, the first blow suddenly burst into flames.

The dull pain of the spoon had been enough to prime her body and arouse her, but no amount of arousal could hide the burning lines of pain he was drawing on her. The third blow crossed the second, creating an X across her ass, and she steeled herself for the fourth blow, but it never came. Instead, he turned her around to face the camera and removed the ball gag. "Go on slut, beg your fans for mercy, and maybe they'll take pity on you."

Jennifer gasped. Her breathing was tremulous and uneven - she was practically hyperventilating. "Please. Please, no more," She croaked "Please just fuck me, I'll..." She never had a chance to finish though, because while she stared at the screen, Dan brought the cane down one final time across her pert tits. Jennifer's mouth opened wide in a silent scream as that vicious and unexpected blow landed just above her nipples on both breasts. She gasped like a fish out of water, as she watched a welt form almost instantly as an angry red line.

For a few seconds all she could think about was pain, but as it faded from flames to embers she looked around from her tormentor, and realized she'd lost track of him again. She wondered what terrible pain he would inflict on her next. What could be worse than the cane? She didn't have to wait long to find out as she felt something hard pressing against her tight little rosebud. "No!" she cried out, jerking away from the invader. "That's not something I'm into. Please just fuck me already." Jennifer was exhausted, exasperated, and more than anything else, sexually frustrated. She'd been horny before he'd ever tied her up or landed a single blow on her, but now she ached to get fucked. It wasn't a craving; it was a need.

"Take it easy slut," Dan said soothingly as he continued to apply pressure to her asshole. "I'm going to fuck your pretty little pussy in just a second so everyone can watch you cum like the whore you are. This is just the cherry on the sundae. That's all." With a final push, the butt plug popped into her ass, firmly lodging itself there making her feel stretched and full. It wasn't an unpleasant sensation exactly, but it was hardly sexy. That was until he flipped the switch and it started to vibrate. Buzzing away in her rectum it instantly became very distracting.