Poker Loser Ch. 04

Hey Princess,

Friday again, I think I'll just make that our night together. For the next five Friday's you're mine, beautiful. You certainly seemed to enjoy yourself on our last date, so I'm sure you're looking forward to this one. I'd like you to meet me at work at 4, my office building is 555 Trump Street, Suite 38A. I'll be the only on there, I'm in the back office on the right, and I'll be expecting you.

I think I'd like to see you in a sundress, keep it lowcut and short. No underwear of any kind of course. Let's put your hair in pigtails for variety. I'll be waiting gorgeous.

Your Knight in Shining Armor

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Allison walked into Todd's office building, pony tails bobbing as she walked. The short pink sundress rode up her shapely legs, and she had to constantly pull the straps back onto her shoulders as they slipped down. She looked gorgeous, even if the pigtails did make her look five years younger, at twenty years old that five years made quite a difference. Why did men have this obsession with wanting girls to look younger anyway? Shave her pubic hair, wear pigtails... she felt like a 9 year old with her hair like this. Part of what was pissing her off so much was that feeling younger also made her feel more vulnerable. Mostly what was pissing her off was that her pussy was already wet and leaking, and had been ever since she'd started getting ready to meet Todd for their second date. All week she hadn't been able to think about anything but their last three encounters, and her feelings about them were getting disturbing; her dislike and disgust of him was fading and she found herself almost looking forward to Friday at times, wondering what this date was going to be like. And every time, her pussy would get excited. It made her more disgusted with herself than anything else, although that didn't kill any of her suppressed desire.

Walking into Todd's office she looked almost angry, but with the pink sundress and pigtails it came off as more a tantrum in a pouty sort of way. Todd thought she looked adorable, all angry with her twin tails, and the pouty lower lip. Mostly what he noticed was her nipples poking through the thin material of her sundress.

He smiled graciously at her, "Allison, good to see you."

"Hi Todd." her reply was in an almost civilized tone of voice.

"Come here, I want to show you something." Curiosity aroused, she walked around his desk as he stood, and he put an arm around her shoulder, propelling her to the floor to ceiling window. "See out there?" Nodding made the pigtails bob. "My friend works in that building. I told him he should look up here at about this time today." Smiling at her, he watched the despair and embarrassment slowly creep up her face as his full meaning sunk in. Bad enough that she had a date with him tonight, but to have him display her to other people... "Don't worry, he won't tell anyone, and I told him not to take pictures." Allison looked at him, grateful and relieved (dammit!), she hadn't even thought of that until he'd said it.

Submissively she lowered her head as he slipped the straps of her sundress off her shoulders, gently he turned her so that her front was facing the building across the way. Standing behind her, he cupped the undersides of her breasts, stroking her nipples with his thumbs. She sighed as the familiar pleasure took over her. No matter what he did, she couldn't deny that he was skillful at playing her body like an instrument, and he knew just how to build her up to the most amazing orgasms... would it be so bad just to sit back and enjoy it? Opening her eyes, she looked across the way and saw a guy standing there, his face was too far away for her to tell if she knew him or not, but he obviously had binoculars and was stroking his dick, watching the show. Allison tensed, and mentally cursed Todd. Every time she started thinking that she might just be able to submit and enjoy herself while she was with him he had to push her boundaries!

Watching the guy across the way jack off as Todd exposed her body to him was just obscene. She bit her lip as Todd began to handle her breasts more roughly, pinching and squeezing now, pulling her nipples as far as they could go before releasing them. Her hips were grinding back into his hard dick, although he was fairly sure that she wasn't aware of the fact, one of the great things about playing with her breasts first was that she tended to lose control of her body if he did things right. Slowly the dress was lifted above her hips, exposing her pussy to the guy with the binoculars. Allison was now ignoring their silent watcher as Todd's fingers slipped through her wetness, enticing more heat between her thighs. Spreading her legs to allow him better access, she wondered a little at her wantonness, especially considering that she knew that had a watcher. Maybe she had a little bit of an exhibitionist streak in her. The slickness in her pussy stated her definite arousal, Todd turned them both so that they were sideways to the big window, and he lowered his head to her nipples, teasing them with his tongue. He noted that the pale skin of her tits still held the faint traces of the hickeys he'd given her the last Friday, this Friday he only added one to each breast, on the inner curves of her cleavage.

Lowering himself to his knees, he pushed his face between her thighs, burying his face in her wet silkiness. Allison moaned as she tried to keep herself upright, spreading her legs a little more to give Todd more access and herself better balance. Clutching his head with her hands, she let her own head fall back as she whimpered, he gave her pussy a tongue-lashing, using his hands on her ass to push her onto his mouth. Once Allison was balanced, she let one hand drift up to her own nipples, pinching them and twisting them... until she remembered their watcher and quickly pulled her hand away, like her fingers had been burnt. Panting, she tried to keep control of herself as Todd pushed his tongue into her hole and wiggled it, she had to bite her lip to keep from screaming when he sucked her clit into his mouth, rolling the little bud with his tongue. When he bit down gently as he sucked, she came, moaning and shaking, her pussy juices slicked her thighs and the smell of her filled the room. Her boobs jiggled as she came, bouncing around while she struggled to stay standing. It wasn't until her grip on his hair loosened that Todd finally released her clit from his mouth.

Exhausted, Allison allowed him to bend her over his desk, with her ass facing the window, her inner thighs were glistening with her juices. Todd ran his finger up one thigh and then stuck it in his mouth, sucking it clean. He waved merrily to his friend across the way, and then used his fingers to spread her pussy lips for him, they were pink and engorged. Carefully, he inserted one finger into her hole, swirling it around. She moaned and moved her hips slightly. Pulling the finger out, he positioned it at her ass, shockingly Allison stood up, shaken.

"Don't do that!"

Todd stared at her, she couldn't be reneging on their agreement! "You liked it well enough when I stuck my dick up there."

"It's dirty," her voice shook a little as she tried to forget the pleasure of the night when she came while he was in her ass, "It's dirty and it's wrong. Things aren't supposed to go in there."

Slightly angered, Todd didn't say anything, he just turned her and pushed her down onto the desk.

SLAP! Allison squealed as his hand smacked her ass, leaving a bright print. SLAP! SLAP! SLAP! Squealing and squirming, her ass cheeks were jiggling as his hand impacted them and her body bounced, trying to escape the punishment.

"Please stop! It hurts!"

SLAP! SLAP! SLAP! SLAP!

Finally he stopped, pink hand prints were all over her butt, and she had tears in her eyes from the sharp pains.

"You are mine to do with as I please on these dates," his voice brooked no argument, "And if I want to put something in your ass, I will damn well put something in your ass. As far as I'm concerned, plenty of things can go in there."

Allison nodded, she didn't trust her voice to hide her pain and discomfort. It satisfied Todd though, he pushed two fingers roughly into her pussy, making her wince, and without ceremony he forced the soaking digits into her ass. She choked on a sob as her asshole was stretched again, his fingers began moving in and out of it, making her even more uncomfortable. There seemed to be no lower debasement for her to go, with her ass impaled on his fingers while she was bent over his desk, his friend watching through binoculars across the street. Incongruently, she wondered what it looked like to see his fingers in her butthole, and then she wanted to slap herself for thinking something so disgusting. Gritting her teeth, she just bore it as he wiggled his fingers, twisted them right and left, and even tried to spread them apart.

Finally he pulled his fingers out and her entire body relaxed in relief. Pulling her off the desk, he pushed her face first against the glass. Nipples hardening at the cold encounter, her boobs were smashed flat against the window, and trying to move back she encountered his unyielding body. The sound of a zipper, a few adjustments, and then he was pushing his dick into her pussy from behind, making her realize that she had stayed wet the entire time he'd been playing with her ass. He held her hands at her wrists, pressed above her head against the window. One cheek and her breasts were flattened against the cold glass, and as he began to move in and out of her quickly, she realized that the guy across the way was still watching. Nothing was hidden from him as Todd pounded her from behind.

Just as she could feel arousal stirring in her pussy, despite the discomfort of the position and her acute humiliation, Todd moaned and thrust hard into her, sending spurt after spurt of his cum into her unfulfilled pussy. He pulled out quickly, leaving her gasping and wanting, braced against the glass. Slowly she straightened up and pulled her dress down and the straps back over her shoulders. Glancing out the window, it was obvious that the guy had cum all over his own window, and was now cleaning up the residue.

Todd didn't give her a chance to grab a tissue, and as he grabbed her hand and pulled her out the door with him she could feel his cum beginning to drip down her thigh. Well, hopefully they'd be able to get to the car without anyone seeing.

"Quick stop," he said, grinning at her, before coming to a halt in front of a door just next to the front doors, knocking on it. Allison grimaced and squeezed her legs together, trying to halt the flow of his cum down her leg. The door opened and Todd leaned in, "Hey guys," he pulled her up next to him, "This is Allison, Allison, these are our security guards."

Allison's eyes flicked quickly over to the monitors in front of the man and woman sitting there, and realized to her horror that one of them showed the office that she and Todd had just come out of.

"Great show!" said the man, grinning at her. He was black, maybe an inch taller than her if that, average build. The woman sitting next to him was a stunning blonde, the first thing a person noticed about her was how nicely her chest filled out her uniform. She was also grinning at the couple in the doorway.

Allison looked at Todd in horror, and he laughed at her expression, "Don't worry Princess, they aren't going to tell anyone, and they've even agreed to delete that part of the tape! You just gotta make sure it's worth their while."

"That's right," said that man, apparently he was the talkative one, "I need me some relief. Come 'ere slut." The woman just looked on, an avid and excited expression on her face.

Looking entreatingly at Todd, she realized that there would be no help from him. His face was just as excited as the woman's. Swallowing, she slowly dropped to her knees in front of the black man. Before she'd even gotten in position, he'd pulled out his dick and had it ready. Not as thick as Todd's (was anyone's?) it was about 9" long and black as night. Allison opened her mouth and lowered her head onto it. As she began sliding her mouth up and down, the man's hands grabbed hold of her ponytails,

"Gotta love a girl with handlebars!" He sighed in happiness as her mouth slid wetly over his shaft. The blonde was leaning forward and watching eagerly, Todd was behind her, with his hands down his shirt. Well, if there was any part of her that was an exhibitionist, it was probably getting worked out of her today. She was a little jealous of the woman, knowing just how skillful Todd was with his hands. Her own nipples were hard and aching still, as unfulfilled as her pussy after that quick fuck against the window. The dick in her mouth twitched a little as she sighed around it.

What would her father think if he could see her now? His perfect WASP daughter with a black dick sliding easily down her throat. Probably he'd disown her, if he hadn't already for all of the perverted acts Todd had put her through. Moving as quickly as she could, she used every trick she'd ever learned to get the black man to cum, just wanting to get it all over with. It was effective, about a minute later he was shouting loudly as his salty cum slid down her throat. Allison felt like the worst kind of whore, this was the second time she'd had to swallow a man's cum, and this time it was black cum filling her belly, from a guy whose name she didn't even know. Finally his dick stopped leaking fluid into her mouth and she pulled away, getting to her feet with alacrity.

"My turn," the sweet, soft southern drawl stopped Allison in her tracks, as the blonde woman got up from her seat, her breasts were hanging free of her uniform; larger than Allison's, they were like two huge balloons on the woman's chest, with large prominent nipples. Allison stood frozen as the woman stepped forward and kissed her full on the mouth, a soft probing tongue slipped between her lips, sharing the taste of the cum that she had just swallowed. Numbly, Allison just stood there as the blonde pulled away and sighed her satisfaction, "You always taste so good Carl." a wink to the black man and then she pulled Allison over to the chair she had been sitting in and pushed the frozen brunette into it.

Allison slumped in the chair, unresisting and unbelieving as the blonde's strong hands pulled her hips to the edge of the seat and lifted up them hem of her dress.

"Oh my," The blonde turned back to look at Todd, "Looks like someone else left me a treat too!" Todd grinned at her as she turned back to Allison and began licking her open thighs. Slowly, the blonde head worked her way farther and farther up the smooth thighs, cleaning Allison's juices and Todd's cum. Big hazel eyes watched the entire process in complete shock. When the blonde reached her pussy, Allison gasped and her head flew up. Now she could see the men staring at the lesbian act being performed on her, and her face turned bright red with humiliation even as she whimpered her arousal. Todd's stern eyes caught hers, and she stared straight at him as the blonde made sighing noises into her pussy. Moving her hips in time to the blonde's expert licking, Allison couldn't tear her gaze away from Todd's, even though she could see the black man beginning to stroke his slowly hardening dick again.

It was the worst kind of flaunting exhibitionism as the men watched her breasts heave and her face contort with passion while another woman tasted her juices. All of it just turned her on more and more, she'd never realized she had such an exhibitionist streak in her! But just seeing the men's facial expressions as they watched her moan and hump the blonde's face, seeing their obvious desire, it made her more and more turned on. Then the blonde's mouth moved lower, and she began licking around Allison's crinkled ass hole, sucking on it and pushing her tongue against the hole. Allison almost screeched and jumped up, but there was an obvious warning in Todd's gaze, and she slowly forced herself to relax. Once she did, the anal rimming started to feel amazingly good, little nerve endings hummed with pleasure as the blonde's soft tongue teased her ass. Biting her lip to keep from screaming pleasure, Allison's entire body jerked as the blonde managed to force just the tip of her tongue into her ass. It felt amazing, but so so dirty... and all of it compounded by the men watching...

The blonde pinched her clit and Allison came immediately, the feelings of shame and humiliation of having another woman licking her and sticking her tongue in her ass was amplified by the surprising pleasure she got out of having an audience. Her clit was twisted and pinched as the blonde wiggled her tongue in Allison's tight ass, heightening Allison's passionate cries. Finally, red with embarrassment, Allison's body slowly relaxed, and the blonde pulled her tongue from her ass and began licking the juices that had flowed out of her pussy. Whimpering as the blonde hit very sensitive flesh, she could see that the black man had another massive hard on, and she was afraid that Todd was going to make her do something about that too... or even worse, make her return the favor to the blonde. She wasn't sure which was more wrong, anal sex or lesbian sex, but she knew she didn't want to do either. No matter how good it had felt to be eaten out by another woman.

Fortunately, when the blonde pulled away, she looked over at the men too. Winking at Todd, she told him, "You guys get on out of here and have a good date, looks like me and Carl have some business to take care of." Big boobs bouncing, the blonde got to her feet as Carl moved towards her. Todd said goodbye to both of them, and pulled Allison out of the door as the two in the room began to kiss passionately.

When they got to the car, Allison realized that almost three hours had passed since she'd first showed up at Todd's office building. Three hours of almost non-stop sexual activity. She was exhausted.

Thankfully, Todd didn't want anything more but to run by a Checkers and eat. On the way home, he made her give him a blowjob in the car, her ass high in the air so that passer-by's could see her pussy peeking out from under the short skirt of the sundress. Since her parents weren't home when they got there, he pulled into the driveway and had her finish his blowjob while he played with her nipples, pinching and tugging on them. Allison got out of the car incredibly worked up, her nipples sore but unfulfilled. Todd drove away, waving her to her cheerfully.

As was becoming habit, as soon as Allison got inside and was in the privacy of her own room, she masturbated. Closing her eyes she could see the two men watching her as the blonde licked at her pussy, and the guy watching as Todd fucked her up against the window. Picturing their faces she came hard on her fingers, one of which seemed to have somehow slipped up her ass.

She lay there, completely exhausted, and pulled her fingers from her pussy and the one out of her ass. Only three more dates... could she last three more dates without becoming as sexually depraved as she was?? Uncertainty and shame filled her, but then the front door open and closed and she could hear her parents voices and she ran to the bathroom to shower off the smell of rampant sex from her body.