Winning The Bet

Chris was 18, a typical guy for his age. He had the same problems most others had at his age. Puberty had hit him early, and hard. Ever since he was 11 his face had erupted with acne, and although his skin had since cleared, his self-confidence had been severely damaged.

While his friends had been out getting to know the many pleasures of the female form, Chris had spent hours alone in his room, frantically tugging at his cock, thinking of all the girls he should be out fucking. Although he now enjoyed going out to the pub with his mates and getting drunk, whenever the subject of girls arose, he would clam up and try to change the subject.

One afternoon, he had gone out and come back early, around 6 or 7, after an all-day drinking session on account of a friend’s 19th birthday. They were all to go home, get some food, get changed and meet back in town at 8:30 for some more drinks and a club. As Chris arrived home, he noticed the house was empty. His father was away working on the rigs, so his absence wasn’t unexpected, but he noticed his mother had left a note for him on the table:

“Gone out with the girls, back late…..don’t wait up!”

love Mum.

Chris looked at the note and tutted, he disapproved of his mother’s behaviour when she went on her “girl’s nights out.” She always came back drunk and made a noise.

Anyway, he screwed up the note and tossed it away before making himself dinner and changing. He then left the house to meet his mates at he club.

As the night went on, they inevitably got talking about girls and Chris did his usual silent routine. This time though, he was to be the focus of the conversation. They all noticed how he never seemed to have a girlfriend and how they had never even seen him chatting to any girls.

“You a virgin Chris?” they laughed, as the taunting began.

“No” muttered Chris, lying.

“Liar!!” came the response, “Then how come no-ones ever seen you with a girl?”

Fuelled by the taunting and bravado, Chris replied “I get my share, don’t you worry.”

The group laughed. “Yeah, right Chris, whatever!”

Chris was getting really angry now, and insisted he as no virgin and did OK with the ladies. “Bet you I pull tonight” he issued.

The group ignored the challenge, “It don’t matter,” one said, “We’re only kidding mate.”

However, Chris was adamant now and quite pissed, “No bullshit” he said again, “Come on, put your money where your mouth is!”

“OK then” came the instant reply, sensing easy money, “£20”.

“Fuck it”, said Chris proudly, “Make it £50”.

They shook on it, before in a sobering moment, Chris realised he didn’t have £20 let alone the £50 he had raised it to. Before Chris could consider his difficult position, he was being dragged through town towards the evening’s final destination.

“We’ll even make it easy for you” one said as they queued outside the club. They had gone to the Flamingo club, a place with a “grab-a-granny” reputation- the women there were notoriously easy, even Chris knew that. They went in and ordered some drinks, assessing the scope of the talent in the place. As they were discussing the standard of women in the club, one of Chris’s mates noticed a woman on the dancefloor.

She was about and dressed in a tight black lycra-style top and short black glittery skirt, she could barely stand on the ridiculously high heels she was wearing and she was looking over at the group waving.

“Here Chris”, he said, “Looks like you may be in luck”, gesturing over to the woman waving, she was clearly very drunk and her ample frame was miraculously squeezed into clothes which were clearly to small and too young for her to be wearing, “She ain’t too bad neither!”

Chris looked across at the woman staggering around on the dancefloor. As he looked, his face turned ashen white. The woman they were watching was Chris’s mother!

Chris was so embarrassed and walked over towards her, almost forgetting he was with the group until one shouted after him, “Go on tiger!” Chris had all but forgotten the bet, and had gone over to his mother with the intention of rebuking her. However, his mum was well-drunk and took little notice.

“Oh, lighten up baby” she giggled “Have a dance with your old mum!”

Chris just wanted to get her out of there, but before he could act, his mother was clumsily leaning against him. The interaction between them was more Chris holding her up than dancing with her, with his mates laughing and jeering as they watched.

After the song had finished, his mother stumbled off towards the toilet and Chris joined his mates at the bar, somewhat embarrassed.

“Looks like you’re well in there Chris, quids in mate!”, they laughed, reminding Chris once again of his bet.

“Yeah” muttered Chris, suddenly realising the group had no idea who the woman was, “Looks like you owe me that £50!”

“No way”, they replied, less than keen to part with their money, “We pay up when you get a snog!”

Chris was miffed at the reply, and remembered he had no way of paying a losing bet. “Oh come on”, he protested, “That wasn’t part of the bet.”

“Bullshit” one replied, “How are we to know you’ve pulled her, you could know her.” As they replied, the woman in question returned from the toilet and moved back onto the dancefloor. “Yeah” another added, “That could be you’re mum for all we know!”

Chris’s heart jumped, there was no way he could pay, then he quickly downed a double whisky and slammed his glass down on the bar.

“Think I’d do this to my mother”, he slurred drunkenly, as he strode purposefully over towards her, his heart pounding in his chest. Without stopping t think, he grabbed hold of his mother and pushed his lips hard against hers, taking her totally by surprise. As she broke away, she seemed to have a moment of sobriety and she looked at her son and barked “What the hell was that?!”

Chris suddenly realised what he had done and stuttered “Er…sorry, I’ll explain in a minute”, before leaving his mother, still somewhat shocked, and returning to his mates.

“Fucking hell!”, they gasped, before each giving him £10 (there was 5 in the group).

“We’re gonna get off Chris, try another club in town, don’t wanna cramp your style!”, they then smiled before going, leaving Chris in the uncomfortable position of explaining to his mother his previous actions, as she had now joined him at the bar.

“Er…sorry….it was a bet….I couldn’t afford to lose!” Chris’s mother looked at the bunch of crisp ten-pound notes in his hand.

“So I see” she smiled understandingly, “Looks like the drinks are on you then!”

Chris was so relieved that she had taken it OK and got in a couple of large drinks. She was so drunk, he thought, she probably wouldn’t remember anything tomorrow, and with the money he had won, he planned on being the same way. Within an hour, the 2 were both well-pissed and decided to have a proper dance together. This time, they were holding each other up.

“So what was this bet about?” she asked.

“They said I was a virgin, and I couldn’t pull a girl tonight.”

Chris’s mum laughed, “I’m not surprised kissing like that!”

Chris looked embarrassed, not wanting to bring it up again. She could see that she had embarrased him and continued, “Don’t be silly, I’m only kidding”, she beamed, “Come here.”

She grabbed hold of Chris and pulled him towards her, placing her lips gently against his to give him a purely innocent kiss.

However, as their lips met, Chris was sure he felt her apply more pressure, and responded by doing the same. Then she placed a hand behind his head, and held him there as he felt her mouth beginning to open.

Chris was unsure what was going on, did she realise what she was doing? Maybe she was just being affectionate, and he was reading it wrong. Then he found out for certain as he felt her tongue pressing against his mouth. He opened his lips and pushed his tongue against hers, hearing her sigh as they kissed with increasing passion. Chris was overcome, and put his hand on his mother’s behind, grabbing her ass firmly as he pulled her body against him, watching her close her eyes briefly as he did so.

Feeling her body against his, she realised she could feel his stiffening cock through his pants, pushing against her soft stomach, and she knew this was wrong. Breaking away from him, she stuttered,

“I think you’d better take me home.”

Chris was somewhat disappointed, and due to the swelling bulge in his pants, extremely frustrated, realising it would be some time until he was home and able to attend to his lust.

His mother grabbed her bag and the two stumbled out into the night.

“Never get a taxi at this time” said Chris, and the air staggered drunkenly through the town, each wrapped up in thoughts of what had taken place some minutes before but remaining eerily silent.

Eventually the chilly night had gotten to her, and she grabbed Chris and ducked into a quiet alleyway.

“What are you doing mum?” said enquired, first to speak for a good 10 minutes, as he watched her sliding down her knickers.

“I need a pee” she said, “Keep a look out will you.”

Chris was slightly uneasy as his mother slipped out of her knickers and put them in her handbag. She turned her back, and as she began to squat down, Chris turned away.

Soon he heard a trickle and a splash and realised she was peeing. He couldn’t help but turn round, and saw she had hitched up her skirt and he could see her bare buttocks in the dim lamplight. As he watched his mother pee, he needed to go too, and he unzipped his fly and pulled out his penis.

As he stood against the fence, he heard his mother’s voice behind him, “So are you then?”

“What?” he replied confused, trying to focus his attention to his dick.

“A virgin”, came her reply from behind him.

Again, Chris looked down at his penis. Staring at his mother’s behind had caused him to stiffen slightly, and he was having trouble peeing through his engorging member.

“I, er don’t really wanna talk about this mum”, he answered bashfully.

“It’s OK, you can tell me love”, she reassured, already believing she knew the answer was yes.

“Well, if you must know” he answered impatiently, the stream of pee finally erupting from his swollen cock head, “Yes I am.”

The sound of his peeing had disguised the fact his mother had finished and he was only made aware of her proximity to him by the closeness of her voice as she continued.

“Shame” she said softly, now right behind him, looking over his shoulder. The fact he was peeing prevented Chris from turning to confront his mother, but it became uneccessary as she moved round to his side, “You have a lovely big cock.”

“Mum!” muttered Chris, “Do you mind?!”

“Not at all”, she replied, moving her hand slowly towards his which was gripping his firm young cock as he peed against an old wooden fence. Chris juddered as her fingertips touched his hand before creeping slowly towards the exposed shaft of her son’s penis.

Her fingers brushed along the firm flesh, as she traced the veins along its length. Then as she reached the tip, she ran her fingers gently along the glans and across the tip, breaking the stream of warm pee with her palm, soaking her hand and spattering both their legs with clear yellow liquid.

She had realised how horny she was feeling and remembered her husband was away. If she was going to get the satisfaction she needed so much, it was going to be there and then, and it was clear from the bulge she had felt in Chris’s pants when she kissed him that he was obviously frustrated too.

“I need fuckered”, she uttered wantonly, as her hand wrapped around his penis (he had now finished peeing).

“But not me” he tried to reply, before her hand began stroking him nice and hard, until he was quickly fully erect. Then she moved round in front of him and pulled him ,by his cock, closer to her. Their bodies pressed firmly against each other, she took his hand and placed it at the top of her naked thigh.

“Yes baby I want you, feel how wet you mother is for your fat young cock!”

Chris could protest no longer as his trembling fingers felt the stickiness of his mother’s vaginal opening. She closed her eyes and gasped as his enquiring index finger tip pressed softly against her slit, and she pushed her face against his, their mouths meeting roughly as they continued the kiss she had prematurely broken off in the nightclub. This time however, Chris broke off the kiss and pushed his mother back against the fence. She looked deep into his eyes as he grabbed her thighs firmly in each hand.

It was a situation she had been in many times before, and she opened her legs wide. “Oh, that’s it!”, she panted “Are you gonna put it in me?”

“I’m gonna put it in you”, he hissed in reply, “I’m gonna screw your wet cunt and fuck you like the slut you are!”

Overcome with lust and animal passion, he felt his mother’s hand guide the bloated head of his cock against the entrance to her pussy, and he thrust his hips hard, sliding his dick into her so hard and fast, that it lifted her clean off the ground, forcing her back hard against the wooden panels of the fence. She screamed with delight as she felt the entire length of her son’s cock slide deep into her in under a second, and she wrapped her legs around his waist to keep him deep inside her pussy.

Then Chris slowly began to withdraw a few inches before ramming it back into her. Chris had slipped her left arm out of the strap on her top, and was lowering the top over her ample cleavage. He reached his hand inside and pulled out her bare breast, mauling it with his big clammy palm. Beneath his hand he could feel her nipple was firm and hot, and could see the stubby nipple of her right was also stiff through the tight lycra vest.

Although her son was inexperienced, she had had much worse fucks, and the sheer girth of her son’s cock more than made up for his lack of technique. She was writhing and moaning as Chris primitively hammered his mother against the fence, making it clatter noisily as he pounded her hairy cunt.

She was enjoying being so brutally banged by her own eager teenage son and was rapidly building up to an orgasm, when she was alerted by her son, who had become more erratic in his thrusting. She knew he was going to cum soon, but she was keen to climax first herself.

She was disgusted then, when just as she was on the verge of climaxing, he began to withdraw his cock slowly from her burning pussy.

“What the fuck are you doing?”, she screamed, scaring her son somewhat.

“I’m gonna cum mum”, he replied, thinking she hadn’t realised.

“I don’t fucking care, I’m on the pill!” she cried anxiously in response, “Shove your fucking big cock back in me now you bastard!”

Amazed by his mother’s frenzy, he quickly slammed his cock back roughly. Making her huge soft bosom ripple as it lay exposed against her torso.

“Make me cum baby!” she panted as her abdomen tensed with the rough re-introduction of her son’s fat penis, “Make momma cum!”

A couple of hard thrusts more was all it took to make her vagina contract hard around Chris’s engulfed cock, as she felt the climax ripple through her body. As her body shook against the fence, she dug her hands deep into Chris’s buttocks, pulling his groin hard against hers, and his knees buckled and his balls jerked.

With one last thrust, Chris grunted through gritted teeth as his cock shot his cum deep inside his mother’s trembling body.

The couple enjoyed their intense shared orgasm, as her pussy milked every drop of spunk from Chris’s softening shaft. As the pair leaned back on the fence recovering their breath, Chris reflected on his evening’s work. In the last 24 hours he had won £50, lost his virginity and fucked his own drunken mother senseless down a dirty alleyway.

Nice work if you can get it!!