The bet

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 warning 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 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.