Olivia's Bad Choice

She should have let him pick her up in the bar.

Author's note: This is a shortish one-off story that isn't connected to my Theo, Kendra or Lila series and probably won't spawn any sequels. It's just a fantasy that somehow got stuck in my brain and demanded to be written down so it would leave me alone. It's pretty sadistic to start with (content warning), but don't worry, it gets less so as it goes along.

By the way, I don't intend Rob to be the slightest bit sympathetic, and if he's right in his story of the nasty way Olivia brushed him off at the bar, she's not much better. In fact, they're both pretty much assholes, but I hope you can enjoy what they do all the same.

(And no, I doubt that GHB wipes memory after the fact. That's just a plot device.)

Olivia slowly regained consciousness. She shook her head, attempting to clear it, but it didn't help much. She struggled to piece together the events of - was it the night before? She had no idea what time it was, where she was, or how she had gotten there. All she could remember was planning to go out to Rossi's, one of her favourite bars, for a few drinks with a couple of her girlfriends. Try as she might, she couldn't remember getting there or what had happened once she arrived.

She didn't feel particularly hung over - at least, not enough to account for a total blackout. And why couldn't she seem to move her arms and legs?

As her eyes finally began to focus, she looked around and saw that she was bent over a metal frame. It would have been a table if it had had a tabletop, but instead it was just an open rectangle: four bars and four metal legs. One bar came across her body at waist level and the other supported her upper body just below her neck. The bars were padded, which was good considering that wide leather cuffs around her wrists and ankles were holding her body firmly against them. She was cuffed to the four legs of the table, holding her legs in a wide spread and her arms pointing down at the floor.

And she was naked, her generous breasts dangling downward in the space where the tabletop would have been.

She tugged violently at the restraints, writhing her fingers in a vain attempt to reach the buckles holding her. All she succeeded in doing was making her dangling breasts bounce and swing as she struggled. She was in a windowless room with very little furniture - just a wooden armchair and the frame she was bound to, plus a small table that seemed to be holding a few items that she couldn't make out clearly from her angle. A single overhead light glowed softly in the ceiling.

"Hello," she screamed. "Help! Is anyone there? What have you done to me? What is this?"

Nobody appeared. She screamed again and lunged futilely at the cuffs. After a few minutes she realized that all she was doing was bruising her wrists and ankles, so she gave up and just lay limply in the frame.

Finally she heard a door open behind her, and a man walked around the frame to where she could see him. He was medium height, his shirtless condition revealing a good build, not exactly muscular but fit-looking. He had a neatly trimmed brown beard and brown hair, and wore only a pair of jeans.

He pulled the armchair over and sat, looking at her closely. "Well, Olivia. I see you've rejoined the world."

"Who the fuck are you and what's all this?" Olivia yelled. "Let me go right now!"

"What's all this? Isn't it obvious? I drugged you at the bar last night, brought you here half-unconscious, stripped you and strapped you to a simple but effective bondage frame."

"Why are you doing this?" She tugged again at her restraints.

"Now, Olivia, you're an intelligent woman. If I had just wanted to kidnap you for ransom, I wouldn't have gone to the trouble of stripping you and tying you up in a contraption like this. No, I wanted to get you back for the horrible way you treated me last night. And just plain fuck you for its own sake."

Olivia looked puzzled. "Wha - what?"

"I'm not surprised you don't remember. GHB does that to a person. It also makes them pretty incapable of resisting when someone walks them stumbling out of a bar. Your friends were busy chatting up a couple of hot-looking guys and didn't even notice until you were gone. You need friends who will take better care of you."

"So, what did I say?"

"Well, when I first saw you in in the bar wearing that skimpy black dress with your tits practically bulging out the top, it made me so horny I just had to have you. To see if those tits were actually as gorgeous in reality as they looked through your dress. To find out whether you waxed your pussy. To find out what your cunt felt like wrapped around my aching cock. So I offered to buy you a drink. I'm slick enough that I can usually talk a cunt into coming home with me as long as I can get an opening."

"Obviously, you didn't like my answer."

"No, I most certainly did not. If I recall, you said something like, 'Fuck off. I don't take drinks from assholes who hit on me in bars.' That really pissed me off. Being rejected once in a while is just the cost of doing business in the bar scene. But you didn't have to be so stuck-up and humiliating about it. So I spiked your drink."

Did she really brush him off that rudely? She was used to deflecting unwelcome advances in bars, but she was usually civil about it. Maybe he was the twelfth guy in a row who tried to hit on her, and she just snapped.

"Did you - did you -" She let her voice trail off.

"Did I fuck you? Not yet. I felt you up, of course, and yes, those tits feel as good as they look." He punctuated the remark by squeezing both her breasts, hard, pulling a squeal of shock and pain out of her throat. "But there's no fun hate-fucking an unconscious woman. I want you to feel exactly what I'm going to do to you, so you'll know what price you're paying for your attitude. So I just staked you out so you'd be ready for me when you woke up."

"Who are you?" she asked again.

"You can call me Rob if you want. But who I am doesn't really matter. I'm just some guy who had the hots for you in a bar. And when I see what I want, I get it."

Rob walked around behind her and gave her ass a squeeze, running his hand over her bald pussy. "And I see that, yes, you do wax that pretty cunt of yours. Feels good." He tried to slip his finger between her lips but she squirmed sideways in the frame, making his fingers miss their target.

"I see you've got too much range of motion in that thing. I could strap your knees to the legs as well, but I've got a better way of keeping you still." He gave her a hard swat on the ass, walked over to the table, and came back with a big dildo attached to short metal arm that in turn was attached to a metal cross-bar with screw clamps on both ends. He positioned the device between the back legs of the frame with the end of the dildo almost touching Olivia's pussy. He tightened the clamps on the crossbar to the legs of the frame, holding it firmly in place.

Once the device was attached, he unscrewed a couple of knurled knobs on the arm and moved the dildo right up against Olivia's pussy lips. She tried to squirm away but he wrapped one arm around her waist in an iron grip and pressed her against the padded bar of the frame so she couldn't move. Then he pressed the tip of the dildo firmly against her pussy lips, and kept pressing. Her lips parted and the huge dildo slowly sank into her vagina until it bottomed out against her cervix. Then he tightened the knobs firmly and stepped back.

To say that it hurt would be a huge understatement. It was fat and long, and he didn't put any lube on it, so it felt like a rod of pure fire being shoved up her. She screamed loud and long, and surged forward to try to get it out of her, but the straps at her ankles held her waist firmly against the bar, trapping her on the intruder.

"That should help you learn not to be such a bitch cunt to guys who only want to get to know you better," Rob said as he sat back down in the armchair. "And it'll make you stop squirming all over the place." He watched her for a few minutes as she fought to regain control of herself, tears of pain rolling down her face.

Rob finally stood up again and faced Olivia's tear-stained face. Moving slowly and almost casually, he unfastened his belt, unzipped his jeans, and slid them down and off. He was commando underneath, and his cock was already so hard it practically vibrated as it sprang free.

"Now your cunt's all plugged up so I can't fuck it. But that's not really what I'm interested in. I've always wanted to know what it feels like to fuck a woman in the ass but could never find one who'd let me. If you'd have let me pick you up properly, you'd have had some say in what we did together, but now you don't get to be choosy." He walked around behind her again and started to spread her cheeks even further apart than the restraints were already holding them.

Olivia burst into tears again and tried desperately to squirm away, but was held immobile by the dildo in her snatch. "Oh God, no, not in the ass! Please! I let a guy try it once and it hurt so badly I couldn't stand it. I had to make him stop before he was half-way in. I can't go back to that. No!!"

Rob stopped what he was doing and listened to her pleading more and more hysterically. Rob let her go on for a minute, then said, "Bitch, you make way too much noise." He went back to the table, his rigid cock waving in front of him as he walked.

"Oh Jesus," she thought to herself. "What the fuck is he going to come up with now?"

What he came up with was a wide leather panel gag with a big stuffer ball built into it. He positioned it with the ball in front of her mouth, and she gritted her teeth firmly to try to keep out this new intruder. Rob just reached under her body, grabbed a nipple and twisted it, really hard. She reflexively opened her mouth to scream and he stuffed in the ball, cutting off the scream and turning it into a muffled but frantic "Mmmmpphh." He buckled the gag firmly behind her head.

"Now I can't throat-fuck you either, but I don't care. I'm not crazy enough to put my cock anywhere near those teeth, not in the mood you're in." He walked back behind her again and started gently massaging all around her asshole. "But I'll make you a deal. Be a good girl and I'll use lots of lube and put it in really slow. I won't ram it in hard like I did when I plugged your cunt. Do we have a deal?"

Olivia got control of herself again and stopped her hysterical squirming and screaming behind the gag. Finally she nodded.

"OK. You be nice and I'll be as nice as I can." He squirted a generous dollop of lube into his hand and ran it around and in her tight little pucker, using his finger to force some as far inside as he could reach. Feeling her sphincter tighten firmly on his finger, he muttered, "Shit, this is going to be a tight one. I'm gonna like this." He eased his finger out and put another big squirt on the end of his cock.

Rob put his cockhead against her pucker and began to push, gently at first and then harder, until the head finally popped in past her sphincter. She let out a muffled yelp behind the gag, but resisted the urge to scream this time. She just clenched her hands into fists, screwed her eyes shut, bit down hard on the silicone ball jammed into her mouth, and tried to blank out the pain.

Rob left just the tip of his cock in her for a minute. The red-hot burning ring of pain gradually subsided and she could breathe again. He pressed his cock in another couple of centimeters and stopped again when a spasm made her yelp with pain. Again, he did as he promised, waiting until the spasm had subsided before gaining another centimeter of territory. Bit by bit, he gradually worked his cock in until it was buried balls-deep in Olivia's nearly-virgin asshole.

"Christ, I was right! This is the tightest hole I've ever had my dick in. No wonder so many guys love anal." He began thrusting, gently at first, then harder and deeper until he was pulling almost all the way out and then slamming all the way in. She grunted with pain behind the gag as each thrust pushed her body forward in the frame and made her hanging breasts rock back and forth under her body. But she didn't scream any more. It hurt almost as much as she'd feared, but the slowness of his insertion meant that she was well stretched out and the pain was bearable.

As Rob kept thrusting, Olivia began to wish he'd hurry up and blow his load so the assault would be over. But Rob seemed to have almost infinite stamina. It seemed as though he managed to keep going for at least ten minutes before his grunts of pleasure built into one final, powerful thrust that he left all the way in while his hot jizz filled her rectal cavity. It felt almost soothing as her insides were bathed in gooey cream.

As he pulled his cock out, she felt the sticky goo begin leaking out and running down her leg. Rob collapsed in the chair, holding his limpening penis and smiling weakly with pleasure as he slowly came down from his orgasm. "Baby," he said once he had gotten control of his breathing. "That was the best fuck I've ever had in my life. I'm going to have to look harder for a woman who'll do that for me so I don't need to drug them and drag them home."

Olivia lifted her head, which had been hanging down limply ever since Rob had pulled out of her. She managed to make some sounds which, although garbled by the ball holding down her tongue and muffled by the panel sealing her lips, could still be made out as approximating "Now let me go."

"Not quite yet, Babe. I didn't risk as much as I'm doing right now just for one glorious ass-fuck. Now that you're nicely tied up, plugged up and fucked up, I'm going to have a shower and a stiff drink, maybe watch a little porn, and come back for repeat business. You just make yourself comfortable until I get back." Then he walked out the door.

"The utter bastard," she thought to herself. "He's got what he wanted. He's had what he called the best fuck of his life. I'm about six different kinds of humiliated. And my asshole really hurts. Isn't that enough for him?"

As she stood bent over in the bondage frame, trying not to think about how uncomfortable she was with her ankles spread too far apart and her jaw forced open by a big silicone ball, her asshole gradually stopped hurting. Her snatch started feeling better too. She didn't care for the way the dildo pressed against her cervix, but it had only really hurt when Rob first jammed it in. Now, the feeling of being stretched and filled was starting to feel kind of erotic.

Even stranger, the restraints that had so terrified her when she woke up in them were now beginning to turn her on a little. She had played a bit with bondage with some of her other partners, but only to the extent of being handcuffed to the bed with a scarf tied over her mouth. Somehow, this much stricter, more professional bondage seemed to be a different order of sexiness. Now that she could just stand there and appreciate it, the feeling of the leather cuffs firmly holding her wrists and ankles to the frame was making her pussy tingle and even moisten a bit. Even the gag stuffed in her mouth seemed inexplicably thrilling.

There wasn't much play in the ankle cuffs, but she found that she could pull herself up on the dildo a centimeter or two and then let it sink back into its full depth, in effect slow-fucking herself on the object that had caused such pain a short while ago. It wasn't enough to get her off, but it felt strangely good. It certainly passed the time while she was waiting for Rob to come back and finish up whatever else he intended to do to her.

There was just one problem. She gradually realized that she needed to pee, quite badly. She clenched her urinary sphincter and would have clenched her knees together if the cuffs had let her. She stood there in gradually elevating discomfort for ten or fifteen minutes, then suddenly realized, "Why the fuck am I worried about making a mess on this asshole's floor after all the things he's been doing to me?"

With the big dildo jammed up her vagina, her urethra was compressed and it was hard to get her pee started. She wondered absently if this was how middle-aged men felt when their prostate started to enlarge and squeeze down on their urethra. But she persevered and managed to coax out a slow but steady dribble of urine. As it trickled onto the floor, she was glad for once that her feet were forced wide apart so she wouldn't end up standing in her own puddle.

***

It seemed like hours before Rob finally came back in the room. He frowned at the puddle on the floor, then laughed and said as he mopped it up, "I guess I have only myself to blame when I left you tied up without a pee break."

She was glad he seemed to be in a better mood. "I guess the best fuck of his life improved his outlook," she thought as he ran his hands over her naked skin, more gently than he had done earlier. He kneaded her nipples into stiff buds, but didn't pinch them or twist them. In spite of herself, Olivia felt her pussy moisten around the dildo.

"I loved fucking you in the ass, but now I want some variety. Let's find another way to keep that busy ass from squirming around." He picked up a roll of duct tape from the table and wound the end around the crossbar. Then he unrolled it across her back just above the bulge of her ass where she was bent over the bar, then wrapped the other end around the bar. He unfastened the dildo, eased it out of her vagina and removed the whole apparatus from the frame. Now she was still held firmly to the bar by the tape and couldn't move any more than she had been able to when she was impaled, but her pussy was free. She was pretty sure where Rob's cock was going to go next.

Sure enough, he went behind her and began to finger her pussy, prying her labia apart and inserting first two fingers, then three. He curled them and stroked the anterior wall of her vagina, landing right on her G-spot. She gasped with pleasure around the gag when he found it, her breathing deepening. He massaged her asshole with his thumb, but thankfully didn't dig it in - her asshole still felt sore and bruised from its earlier workout.

As Rob slowly worked his fingers in her, he began taking side-trips to rub her clit. After hours of having her vagina stretched but not properly stimulated, it felt wonderful to have things finally happening to it and to neighbouring body parts.

As Rob continued to work her vulva with his hand, Olivia felt her nipples, which had gone soft after Rob had perked them up, get hard again. She began taking long, deep breaths as the pleasure crept up from her vulva and began to spread throughout her body. She had experienced many orgasms in her life, but had never felt quite like this. The gag and the cuffs somehow intensified and multiplied her sensations. She couldn't moan with pleasure, but she began "Mmmphh-ing" rhythmically behind the gag as her body responded with more and more intensity.

Finally Rob decided that he'd had enough foreplay. He braced himself by holding the crossbar with both hands and began to press his cock between her pussy lips. Now it didn't matter that he wasn't using lube. She was so wet that his cock slid easily in, filling her vagina with warm hardness that sent little rockets of sensation through her. Again she bit down hard on the ball in her mouth, but this time it wasn't with pain but with pleasure.

As Rob thrust into her, she felt the tendrils of pleasure that had been growing through her body blossom, amalgamate, and coalesce into a full-body orgasm. It ripped through her body, originating in her vagina, clitoris and cervix and even her uterus before fanning out to embrace every part of her and breaking out into a muffled orgasmic scream.