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The Bet

A short tale of gambling and cuckholding
Annie parked her car outside Pete’s house. She was not looking forward to this; she’d come to pick up Jeff from yet another one of his boozy poker nights. She stopped to gather herself before heading up Pete’s driveway, sometimes he just weirded her out. She was trying to look cool and laid back but it was just too damn hot that night.

The muffled sound of drunken banter greeted Annie as she knocked on the front door. “Come on in,” said Pete as he opened the door, “Though I gotta warn ya, he’s not going too well tonight.” She smiled and squeezed past
Pete. He seemed to make a point of brushing against her on the way through – he was always doing that. As she headed into the kitchen, she felt his eyes follow her.

Sure enough, Jeff had the smallest pile of money on the table as she entered the room. “Hey, hon,” said Jeff as he saw her. When he saw her expression, he added, ”I’m gunna get it all back – just you watch.” Across the room, through the smoke, she could see how drunk he was. They were all surrounded by empty beer bottles. Annie thought to herself that she should have got here earlier, at least then they might have kept enough money for the rent.
She wandered over and stood behind him – after 10 years of being with Jeff she knew better than to try to stop him.

It wasn’t easy to watch him dig himself into a deeper and deeper hole. She watched Jeff get one dud hand after another. She tried to look unflustered but Jeff’s losses and his drunken friends constantly checking her out was starting to get to her. She was a well-preserved forty-something who usually enjoyed the attention of men, but tonight she wished she had covered up a bit more but it was a damn hot night and she’d dressed accordingly.

Finally, Annie had had enough; it was time to get Jeff out of there. Just as she was about to speak, she saw Jeff dealt a killer hand. She felt the excitement surge through her body; they might clean up tonight after all. She checked the cards again. She felt the smile on her face - she was terrible at this poker-face thing. She knew that they’d see her expression and know about the hand - Bill had already started looking at her.

Desperate for a distraction, she muttered “God, it’s hot in here” and undid the top button of her shirt. It seemed to do the job; the guys seemed to fixate on her cleavage as Jeff gradually upped the ante. She moved around the table, the guys kept their gaze on her. It seemed to work, until Jeff started running out of money. She needed to keep this game going otherwise they were out of money until next payday.
“How about an I.O.U.?” Jeff asked, keeping his cool.

Pete just snorted. “You know the rules.“ 

Annie could see this going bad. She needed to keep Jeff in the game. “Pete, you need a fan or something in here”. She undid another button; her black bra was now visible.

“Come on, you know I’m good for it. Just a grand,” pleaded Jeff.

Pete was not even trying to hide the fact that was staring at Annie. The bulge of her breasts was pushing against a shirt two sizes too small for her. He seemed lost in thought for a while then he looked up at her eyes. “How about her?” The others looked up at Annie with sudden interest. Pete kept on talking to Jeff, never letting his eyes off Annie, “I’ll front you a grand but if you lose, she’s part of the deal.”

Annie was horrified, this was not the plan. She pulled her arms up to hide her breasts and waited for Jeff to refuse, to fold his cards and just leave.

“Yeah, I’ll be in on that,” murmured Bill as he shifted his eyes back to his cards. “Me too.” said his son, Evan.

Jeff didn’t move for what seemed to be an eternity then turned slowly to face her. Their eyes met but he didn’t say anything. The desperation on his face was plain enough. She knew the hand he had and knew how much he’d
already lost. She slowly nodded to him. Her heart was racing, she didn’t know if it from the thrill of their impending win or the danger of the situation. She moved and stood behind Jeff.

“Ok, all in to show,” said Pete.

Evan and Bill laid down their cards, each had a pair. Jeff slapped down his queens with a look of triumph on his face. Pete’s smirk was Annie’s only hint that something was wrong. He placed his royal flush on the table. Annie’s excitement was soon replaced with panic.

She looked to Jeff, but her husband just lowered his face into his hands. Pete’s smirk turned into a grin, while the others seemed to still be sizing up the situation. The silence was broken by the sound of Pete’s chair as he started to stand. ”Deal’s a deal”, he said and he started moving towards her. Annie looked back down to Jeff seeking some kind of clarity, but his face was still hidden in his hands. Panic overtook Annie. What if she just refused? They could just get up and go. Pete now stood in front of her. Part of her wanted to run from the house, but she there was something else going on in her head that she didn’t understand. The panic subsided a bit, she paused then looked at Pete. He placed his hands on Annie’s shoulders, looked back into her eyes and with a raised eyebrow gently pushed her to her knees. Even through his jeans, his bulge was clear to see. He undid his belt and dropped his jeans to the floor.

She closed her eyes, bit her lower lip and muttered to herself, “deal’s a deal”. She brought her hands up his legs until she reached his waist and pulled his underpants down. She felt his cock brush against her face. He started rubbing it across her face, against her cheeks and rested it on her trembling lips. Her eyes opened to the sight of his fully erect penis. Her mouth opened and her tongue slid out. She tried her few licks under his helmet and felt a shiver run through his dick. She opened her mouth a little more, massaging the head with her lips. Opened more and drew his cock into her mouth.

His hands were on the back of her head now, pushing her forward. She had always hating giving Jeff head, but there was something different this time. She started massaging his balls as he thrust his dick into her mouth.

It wasn’t long before she felt hands squeezing her breasts. She kept sucking Pete’s cock while Bill fumbled with the buttons of her blouse. She took Pete’s balls into her mouth as Bill peeled her blouse off her arms. This was starting to get out of control. Her bra was unclipped and fell to the ground. Annie blocked all this out; she just wanted Pete to come so she could get this over with. Grabbing the shaft of his dick in one hand she sucked as hard as she could. Bill’s hands were all over her; squeezing her breasts, sliding up her skirt and between her thighs. With Pete’s dick in her mouth and Bill fingering her pussy, she glanced at her husband. He hadn’t moved but was staring intently. When Pete did come, she wasn’t ready for the sheer volume of his juice as it forced itself into her mouth. She tried to spit it out, but his cock filled her mouth, still surging with more and more cum. She swallowed what she could, the rest dripped down her face as he finally pulled his cock out of her mouth.

Annie slid to the floor, trying to catch her breath. Her face was covered in cum but the deal was done. She tried to wipe her face clean, but that just spread the cum further. She stood up looking around for her shirt and saw Bill standing naked in front of her, his fat hairy belly sagging under its weight. His short, stumpy cock ready for action.

“We were all in that deal, Sweetcheeks.” She tried to hide her breasts, her nakedness. As he walked towards her, she took a few steps back and bumped into the kitchen table. He continued walking, pushing he back onto the table until she lay in front of her husband. Bill undid the zip of her skirt and eased it off her. Her panties were next to go, exposing her overgrown bush. With a grin from ear to ear he slid his face between her legs. His beard ticking her thighs as he worked her clit. It had been years since Annie had been with another man, and Bill certainly would
not have been her choice but she felt her wetness and knew what she wanted.

Her back arched as his tongue worked its magic. He then lowered himself onto her, into her. As he entered her heat, she saw her husband. His hands were firmly wrapped around his hard cock. “Is this what he wanted?” she thought as Bill pumped her. His fat gut bounced and rippled as he thrust harder and faster into her. With
a groan and a slight whimper, Bill shot his load. He pulled his heft from her, leaving her naked and spread eagle on the table.

As Bill’s cum starting dribbling down her legs, her eyes cross to Evan. His long and lanky figure matched his long, skinny prick. Annie closed her eyes, drew a deep breath and prepared herself to accept him into her. Evan was a few years out of school but still carrying the pimples of youth. This was certainly a night she was going to remember and she was going to make the most of it. She slid off the table and walked over to Evan. Gently grasped his dick in one hand she whispered in his ear “Fuck me up the arse. Do it slow, do it gentle but fuck me up the arse”. She then moved back to the table and bent over. She’d never had anal sex before, her fear had always made her refuse
Jeff’s pleading, but you only live once and tonight she was going to live it up.

Evan’s hands gently split her buttocks and his fingers worked her anus. His spit slid down between her buttocks, offering some lubrication. She felt his fingers exploring, massaging and finally penetrating her anus. After a couple
of minutes, she felt him fumble his cock around, trying to get the angle right until he gradually worked it into her arse. The pain stunned her but the pleasure was exquisite. He thrust his glorious dick into her and she gave herself over to
the experience. When she climaxed, it was like a revelation to her. It felt like Evan pumped her for an eternity before he moaned and slumped onto her. As he pulled himself out of her, she saw her husband with his now flaccid penis
and hand covered in his own cum.

Annie arose and stood, naked and dripping in cum as the guys gather the clothes and slinked off into other rooms. Only when they were gone did she dress. She grabbed Jeff and pushed him outside. “Interesting night,” Annie thought to herself as she drove Jeff home.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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