Forced Bet (Poker Loser Book 1)

by Golden Angel

  “Of course,” her Dad said, smiling indulgently at her. Mom nodded her head, seconding his permission, not that she ever disagreed with him. “What time?”

  “Oh, ah… usually a little bit before dinner time,” she said, thinking quickly. “They order in food for dinner and the study session run kind of late sometimes, I’ve been told. People get very into the discussion but it’s supposed to be very helpful.”

  “That sounds wonderful,” said her Mother, in tones that sounded like she meant anything but. “I hope this won’t interfere with your dating life, dear.”

  “Nonsense,” said Daddy. “She’ll still have her Saturday nights and it’s better not to be distracted during the school year anyway. You’re setting a good example Allison, it’s appalling how many young men and women spend their Friday nights partying and getting drunk and indulging in all sorts of irresponsible and amoral behavior. We’re so proud of you.”

  Allison smiled weakly.

  *******

  As she walked into Todd’s office building her pigtails bobbed. 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 one that five year reduction made quite a difference. Why did men have this obsession with wanting girls to look younger anyway? Shave her pubic hair, wear pigtails… it shouldn’t give her an illicit thrill.

  Her pussy was already wet and leaking in anticipation and she worried that people would be able to smell it on her. Or that someone she knew would see her. For the first time in her life she’d taken public transpiration to get somewhere and her large purse carried the light sweater and underwear that she’d been wearing up until five minutes ago when she’d snuck into the bushes next to his building to take it all off. Being without a bra in this dress was particularly perilous.

  Todd smiled as she scurried into his office, her slim legs flashing, and she was clutching her purse in front of her.

  “You can put the purse there,” he said, nodding to the chair next to his door. As soon as she put it down he could see her nipples poking through the thin material of her sundress. Standing, he gestured to her. “Come here, I want to show you something.”

  Curiosity aroused, she walked around his desk as he waited for her, putting an arm around her shoulder and propelling her to the floor to ceiling window.

  “See out there?” Her nod made her pigtails bob. “My friend works in that building. I told him he should look up here at about this time today. Don’t worry, he won’t recognize you.”

  Smiling at her, he watched the embarrassment slowly creep up her face as his full meaning sunk in. No wonder he’d wanted to know about her other fantasies. And, just like the previous one, now that it was here she wasn’t sure what she’d gotten herself into.

  “He won’t tell anyone and he knows better than to take pictures. This is just for our pleasure. His. Mine. Yours.”

  She felt grateful for the reassurance, but at the same time she was nervous at knowing that someone would be watching the entirety of their interaction. Though her pussy was flooding, she was still feeling that impulse to show more reluctance, to put up a bit of a fight… otherwise what would their witness think of her? But fighting wasn’t really going to do her any good either; she needed the rest of the tapes so there was no choice. The blackmail really did make everything easier for her, opening up entirely new possibilities that she would have never considered under other circumstances. Now she had no choice but to give in and by doing so she would experience everything she’d always wondered about.

  Submissively she lowered her head as he slipped the straps of her sundress off of 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. She sighed as the familiar pleasure rose inside of her.

  Opening her eyes she looked across the way and saw a guy standing at the window Todd had pointed out. His face was too far away and obscured by binoculars for her to make out any features, but she could see that he was stroking his dick as he watched the show. Allison tensed.

  But there was nothing she could do, and slowly her body relaxed as Todd began to handle her breasts more roughly, pinching and squeezing now, pulling her nipples as far as they would go before releasing them. The top of her dress was bunched around her waist, the skirt swaying gently as she moved her hips back and forth, grinding her ass back onto 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 correctly. Slowly he used one hand to lift the skirt of the dress above her hips, exposing her bare pussy to his friend.

  Allison was now ignoring the distant 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. The exhibitionist streak that she had in her which had never been allowed out to play. The slickness of her pussy stated her definite arousal. Todd turned them both so that they were sideways to the big window as he lowered his head to her nipples, sucking them in his mouth and teasing them with his tongue. He noticed that the pale skin of her breasts still held the faint traces of the hickeys he’d given her last Friday; today he only added on to each breast on the inner curves of her cleavage.

  Lowering himself to his knees, he pushed his face between her thighs, his mouth aimed straight for her wet silkiness. Allison moaned as she tried to keep herself upright, spreading her legs a little more to allow Todd more access and give herself better balance. Clutching at 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. That was too embarrassing.

  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 with pleasure 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 upper thighs and the smell of her cream 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.

  Legs shaking, 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 her 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, displaying their deep pink and engorged state. 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 asshole, pressing lightly on the little hole. Shocked, Allison stood up, her hands coming around to cover her bottom.

  “Don’t do that!”

  “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.

  Todd didn’t say anything, he just used his hands to spin her around and push her down onto the desk, one hand splayed heavily across her lower back.

  SLAP!

  Allison squealed as his hand smacked her ass leaving a bright pink print on her creamy cheek. SLAP! SLAP! SLAP! Crying out and squirming, her ass cheeks jiggled as his hand impacted them and her body bounced, trying to escape the punishment.

  “Stop! Stop it hurts!”
r />   SMACK! CRACK! SLAP!

  It did hurt and, even worse, it made her pussy weep again. The fire in her buttocks from the sharp pain was somehow transforming itself into something that made her want to be fucked and fucked hard. Todd was rather surprised, he had only meant to give her a couple, but there was a sensual plea in her voice even as she begged him to stop. She was obviously enjoying her spanking, her bottom pushing up to meet his hand despite her pleas. In fact, the moment he did stop her butt went right back up again as if begging for more.

  Well if a little punishment and force was what she wanted he could certainly give her that.

  “You are mine to do with as I please on these dates.” His stern voice brooked no arguments. “And if want to put something in your tight little asshole, then I will damn well put something in your tight little asshole and you will spread your cheeks and let me. As far as I’m concerned, I’d be happy to see plenty of things filling that tight little hole.”

  Allison nodded. She didn’t trust her voice, it would surely give away how much he’d turned her on and then she’d lose even more control. It never occurred to her that he’d already realized how much she’d liked it.

  He pushed two fingers roughly into her pussy, making her wiggle and moan, and without ceremony he forced the soaking digits into her ass. Allison yelped as her sphincter was stretched open, a slight burning discomfort from the sensation as his fingers dug deep. He began moving them in and out of her body, making her even more uncomfortable and horny. The deliciously full feeling was back, just as forbiddingly pleasurable as before.

  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 fucking her hole, and then she wanted to slap herself for thinking of something so disgusting. She gasped and moaned as the sensations changed; he was twisting his fingers right and then left inside of her, even trying to spread them apart in her tight channel.

  Finally he pulled his fingers out and her entire body relaxed in relief. Pulling her off of the desk he pushed her face first against the glass. Nipples hardened at the cold encounter, her boobs were smashed flat against the window. When she tried 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. He held her arms at her wrists, pressed high above her head against the window. One cheek and her breasts were flattened against the cold glass as he began to thrust in and out of her quickly, her reactions quite visible to their audience.

  Just as she felt her own orgasm start to build again, Todd moaned and thrust hard into her, sending spurt after spurt of 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, covering herself. Glancing out the window, it was obvious that their audience had shot his own load all over his own window and was now cleaning up the residue.

  Todd didn’t give her a chance to grab a tissue to clean up. Taking her hand, he pulled her out the door with him as she felt his cum beginning to drip down her thigh. Well, hopefully they’d be able to get to his car without seeing anyone.

  “Quick stop,” he said, grinning at her, before coming to a halt in front of a door just next to the main entrance. He knocked 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 said as he pulled her up next to him. “This is Allison. Allison, these are our security guards.”

  Allison’s eyes flickered quickly over to the monitors in front of the man and woman sitting there and realized, to her horror, that one screen showed the office that she and Todd had just vacated.

  “Great show,” said the man grinning at her. He was a good looking black man, maybe an inch taller than her if that, with an average but muscular build. The woman sitting next to him was a stunning blonde and the first thing a person noticed about her was now nicely her chest filled out her uniform. She was also grinning at the couple in the doorway.

  “Don’t worry Princess, they aren’t going to tell anyone. And they’ve even agreed to delete that part of the tape as long as you make sure it’s worth their while.”

  “That’s right,” said the man, apparently he was the talkative one. “You’ve got my girl Laney here all riled up.”

  “Mmmm, it’s a good thing you’ve got a fantasy about being with another woman,” Todd whispered in her ear before pushing her forward. Allison opened her mouth to protest, but when Todd had pushed her she’d stumbled and Laney stood and caught her. Before Allison could do more than stutter, the woman kissed her full on the mouth. Instinctively Allison parted her lips and a soft probing tongue slipped into her mouth. It was just like kissing Chrissy, as Laney’s huge breasts pressed into her own. 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 the hem of her dress.

  “Oh my.” The blonde turned back to look at Todd. “Looks like someone else left me a treat.”

  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 Allison’s smooth thighs, cleaning Allison’s juices and Todd’s cum from her legs . Her touch was much softer, gentler, than any man’s Allison had ever experienced. Big hazel eyes watched the entire process in complete shock. Could this really be happening?

  When Laney 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 with her need. Todd’s stern eyes caught hers and she stared straight at him as the blonde made sighing noises into her sloppy pussy. Moving her hips in time to Laney’s expert licking Allison couldn’t tear her gaze away from Todd’s, even though she could see the black security guard beginning to stroke his dick out of the corner of her eye.

  It was the best and worst kind of flaunting exhibitionism as the men watched her breasts heave and her face contort with passion while another woman feasted on her pussy. All of it just turned her on more and more; she’d never realized she had such an exhibitionist streak in her but something about being watched just flat out did it for her. Seeing the men’s facial expression as they watched her moan and hump the blonde’s face, witnessing their obvious desire, made her more and more turned on.

  Then the blonde head moved lower and she began licking around Allison’s crinkled asshole, sucking on it and pushing her tongue against the sensitive entrance. 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 she had to admit to herself that the anal rimming felt amazingly good, little nerve endings hummed with pleasure as the blonde’s soft tongue teased her asshole. Biting her lip to keep from moaning with pleasure, Allison’s entire body jerked as the blonde managed to force just the tip of her tongue into Allison’s ass. It felt incredible, but so wrong and dirty… and all of it was compounded by the men watching…

  Laney unexpectedly pinched Allison’s clit and she came immediately, the shame and humiliation buoying her up on a wave of ecstasy as her tender nub was twisted and pinched. The tongue in her ass wriggled, heightening Allison’s passionate cries along with her humiliation. Finally, red with embarrassment, Allison slowly relaxed. Laney pulled her tongue from Allison’s asshole and began licking the juices that had flowed from her pussy.

  Was she going to be expected to return the favor? Allison wasn’t sure she could handle that today. There had been so much already… how many boundaries could someone push in one night?

 
; Fortunately when Laney pulled away she just winked at Todd, not seeming interested in receiving a similar favor. “You kids get on out of here and have a good night. It 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 the door as the two in the room began to kiss passionately. It occurred to Allison that now Carl would know what her pussy tasted like too.

  It was a little overwhelming.

  Thankfully, Todd didn’t want to do anything more but run by a Checkers and eat. On the way home she gave road head for the first time. It did the double duty of keeping anyone from seeing her in his car and also pleasuring him. His dick was still faintly flavored from their sex. Around the corner and two blocks away from her parents’ house, Todd pulled over and turned off the lights so that she could finish his blowjob while he played with her nipples, pinching and tugging on the sensitive buds.

  She was becoming quite adept at swallowing his cum, sucking the warm froth down and not losing a single drop. Afterwards he let her break the DVD and promised to throw away the pieces when he got home. Even broken she didn’t want it anywhere near her parents.

  Allison got out of the car incredibly worked up, her nipples sore and her pussy unfulfilled. Todd drove away with a cheerful wave.

  Fortunately her parents were out somewhere. 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 her pussy, remembering the guy who watched as Todd fucked her up against the window. Picturing their faces she came hard on her fingers, one of which had somehow slipped up her asshole, making her feel even more full as her holes clenched and shuddered.

  She lay there, completely exhausted, and pulled her fingers free. Only three more dates. Could she last three more dates without becoming completely sexually depraved? And what would she do when they were over?