The Bet

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Hung girl wagers that Billy will love her cock in his ass.
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Billy flicked a strand of dark hair out of his face, grimacing as he tried to enjoy the bitter liquid stinging his tastebuds.

Another house party. Another beer... Another night watching other people flirt whilst he tried his best to look relaxed, which most likely meant another night going back to his apartment alone.

'At least Alecia's flat is close enough that I don't have to pay for a taxi.'

He sipped from his red cup, plump lips pressed together as he listened to the story a Chad was explaining to a bunch of guys and girls, and when they laughed Billy could only force out an awkward cluck.

"And I said hey, I'm only downing it if you do it with me! We got soooo smashed."

The group grinned and nodded.

"...and would someone stop this girl staring at me, she's got wonky eyes!"

The girl in question, a blonde with impeccable hair and the most Instagram-able face imaginable, opened her mouth in shock, laughing at the douchebag.

"Hey, stop it!"

"Why, you're still staring."

She pouted, and Billy hated how he already knew she was going to get on her knees for that guy by the way she was leaning forwards, despite her 'remonstrations'.

Billy drained his cup.

He usually liked beer, but it left a sour taste in his mouth.

'How do people who act like assholes get so much attention?... Is it because there's no other choice? Maybe smart people just don't want attention, so it's left to a douchebag to talk shit until all the girls are drunk enough to want to examine his bedroom ceiling...'

Billy looked down at his slender knees pressed together and remembered reading in a book somewhere that it was a sign of discomfort to have them closed.

Billy un-coupled his plump thighs, sitting a little wider.

'Why do I have to try and fake this to get girls!'

Billy had tried so many 'methods' to get women... Join a gym, use pickup techniques, just 'be yourself' (like every girl says).... But when you're short, thicc and sporting feminine lips and cheeks, getting a female to look twice at you is pretty much impossible.

Getting friends who are girls? No problem.

Finding a girlfriend? He might as well speed date on Mars.

"HEYY Billy!"

He looked up and saw Alecia waving him over.

Billy excused himself to no reaction, the group too busy guffawing at the way the Chad was teasing the blond girl, and he walked away thankful that he didn't have to watch the mating ritual any longer.

"Hey Alecia... what's up? Rad party."

Thin black eyebrows, tied-up hair and a thoughtful expression gazed back at him.

"Fuck you," she pouted, "I know you're having a sucky time."

He cocked his eyebrow.

"Damn... I was doing so well this time."

"Look, you're.... looking, still, right?"

"Well.. if you mean for a girl that isn't repulsed by me, then yeah, always."

She looked at him with a furrowed brow, wringing her hands.

"Well.. I may have someone..."

He crinkled his nose.

"If you mean that girl that was a born-again Christian and super homophobic, I'll pass."

She pouted.

"NO. No she.... was a wierdo."

"Agreed."

"Okay.. So.... There's this girl I met on holiday, and she's visiting for a few weeks...."

"Wait... you're actually setting me up with a nice girl?"

She bounced on the balls of her feet.

"Yeah.. kinda... well no... but... she's different."

He looked at her curiously, folding his arms.

"Different?"

"Like.. yeah. You'll see."

She didn't meet his eyes as she spoke to him.

"But, I just think it might be worth it because, you know...."

"I'm thirty seconds short of being a virgin?" he finished.

"Sure," she responded, taking his hand and rubbing it.

Alecia was pretty, and even though they had known each other for years the fact that she was cute and enjoyed his company, yet never remotely considered him as anything more than a friend still stung after being rejected as a mate by the rest of womankind (yes, he knew it was pathetic, but years of watching the various guys and girls around him fuck each other's brains out made it hard to ignore when he was always the odd one out).

He tried not to get an erection as she pulled him into a hug.

"Just.. see how it goes," she said, breaking the embrace.

"Sure," he muttered, awkwardly shifting his legs so his three-inch dicklet wouldn't press through the front of his jeans.

***

"Oh, here he is, Billy come here!"

Billy grabbed a second beer as Alecia pulled a girl by the arm to join him.

"Meana, this is Billy."

"Well, uh.. nice to meet you," he said, chin lifting up to the girl towering over him.

The first thing to say was that she was incredibly tall. She wore heels that tried not to enhance her height, but it didn't belie the fact that she was easily a foot above him, with wid-ish hips and long legs that further entrenched the sense of vertigo when looking up at her face.

Her cheeks were angular and pretty, and also quite inviting in the way she smiled. Long dirty-blond hair reached down to her lower back, and she was clad in a blue backless dress which covered the front, but not the sides, of her breasts, to the point where it was difficult not to look without staring, hoping to see more.

"Pleasure to meet you," she responded, offering a slender hand, and Billy took it and found a grip which was soft, but firm. "What do you do?"

Her lilting accent was Irish, and she didn't take her hand away immediately, lingering a touch.

"Oh uh... between jobs at the moment," he replied, thinking it was better than saying 'part time at a supermarket.'

"Ah, well, being a pornstar is a tough industry."

"I'm sorry?"

"Joke."

He let out a nervous laugh, lost in her mesmeric stare.

"Oh... right."

An awkward silence ensued, during which Alecia looked between them curiously.

"Well, I've... got to sort some of the drinking games out....."

"Sure."

"Right."

With that she sidled away, and Billy was left to talk alone with Alecia's curious Irish friend.

Was that a specific joke? Was that what was different about her... Was she a pornstar?

Looking at her once more, it almost looked like her nipples might have been showing through the fabric, but it was hard to say for sure, the gossamer curtains hiding some of the true curves of her long body.

"Do, uh.. do you want to sit down?

"Yup."

Billy led her to a couch which was unoccupied in the corner of the living room, away from the louder groups and speaker system pumping out rap songs at a low hum.

"So, what do you do?"

She smiled, proffering her beer.

"We should cheers first."

"Oh, uh.. sure!"

"Here's to new experiences."

The way she looked at him felt like there was a new undercurrent to the scenario that he had not experienced before in almost any conversations involving a pretty woman, and when they clinked glasses and drank, the beer tasted far more refreshing than it had been previously.

"To new experiences."

They both took a sip, and she brushed a long strand of hair behind her ear as she spoke.

"I'm travelling right now... completed my degree, not sure what I'll be going for next.... but I think I want to go into teaching, maybe psychology."

The lilt in her voice was quite endearing, and Billy found himself leaning in.

"Right... you like psychology?"

A warmth filled his chest as she smiled.

"Absolutely... in fact, we can try some on you, if that's alright?"

"Shoot."

"Would you say you're introverted or extrovert?"

"Oh, probably more introverted than outgoing."

"I would say one-hundred percent introverted."

"Oh...."

"Yeah... you struggle with eye contact, and your knees are turned inwards, which suggests discomfort."

Billy cursed his knees for bending in again, pulling his beer a little closer to his chest, and was surprised when Meana laughed.

"What?"

"It's not a bad thing! It's just who you are!"

"Well, I don't think that's true, extroverts seem to get a lot more appreciation."

Meana cocked an eyebrow and followed where he was glancing, to the blond girl now firmly entrenched with the Chad, talking in low voices and oblivious to the others slamming back their red cups.

"I mean... really, you want to be like those guys?"

He shrugged.

"I don't know, but it just feels like the odds are stacked against people like me, you know?"

She smiled, "Well, I think that means that when someone comes along who appreciates you for being you, they're worth holding onto."

A hand sidled to his knee and rested there, and Billy's blood felt like it was suddenly whipping around his body at the speed of light.

"Oh er...."

"What do you like to do then?"

He looked at the dimples in her cheeks, the wide lips so close to him, and thought he really just wanted to kiss her.

"Erm... what do...?"

She tapped his thigh.

"Like in your own time, silly."

"OH ha-ha, right... I like... movies.... Erm.. bowling...."

Her eyebrow, which suddenly seemed independent of the rest of her face, almost disappeared up into her head.

"Billy, that's some boring ass shite... what d'you ACTUALLY do that's different from most people? Tell me the nerdy bullshit you're into."

He didn't know how to process this, jaw bouncing before he blathered out a response.

"Ww-well uh..."

She rolled her eyes, grinning.

"Spit it out, idiot."

The way she pronounced the word idiot as 'eeejiut' was just so cute that he couldn't help a small grin crossing his lips.

"Muuhmm... okay uh... Dungeons and dragons..... comics......."

"I thought so.... nerdy stuff, right?" she smiled.

"It.... Well yeah kind of... it's...."

There wasn't anything wrong with it, but acknowledging how geeky he actually was felt somehow wrong, like he was losing the small hope of fooling her that he was a feasible sexual partner.

"...it's more interesting than it sounds," he finished lamely.

"Then tell me."

"Uh.. well... I don't know if you'd like it.."

Her hand gripped a little harder on his leg, and he loathed the whimper of excitement that escaped his lips.

Meana seemed invigorated by it, teeth showing in her smile now.

"Look, I'm into singing and horses, and I bet you've never had an interest in those right?"

"Well... I don't really know much about them...."

She scooched closer, and Billy's entire body went numb when she leant against him.

"But I bet you want me to hear about it now... Don't you?"

At that exact moment, with her body heat up against him, he would have been happy to listen to her recount state tax laws for the rest of the evening, managing a nod.

"...So tell me about dungeons and dragons, because I want to hear it."

She oozed charm, and Billy relaxed, beginning to explain the way the game was played, arms reaching out to describe the worlds and scenarios that could unfold, the incredible intricacies with which you developed your character, how sometimes you could lose yourself in it.

She listened with an attentiveness that surprised him, and even asked interesting questions every now and again.

"But.... what if you just decided to, oh I don't know, walk off the map?"

He grinned.

"You won't want to end your character without seeing the plot play out... but I guess you could probably jump off a cliff and die. Who wants to do that though?"

When he had finished they were talking right into each other's space, her leg crossed towards him, hand often squeezing his leg as she spoke, before the conversation turned to subjects that Billy was far less comfortable with.

"So... we should do a game... never have I ever....."

Billy's stomach flipped.

All the questions in this game became about sex. Not exactly a subject he was well-versed in on a practical level.

"I-I'd prefer not to....."

She smiled, stroking his thigh.

"Okay... how about, 'would you rather'!"

"Erm... sure."

He drummed up the courage to place a hand awkwardly on her knee, and was thrilled when she gently placed hers on top, anchoring it to her leg.

"Brilliant," she uttered, "I'll go first!...Would you rather have sex with a woman with a dick, or a man with a vagina and tits."

She seemed keenly interested in his answer as he pulled back anxious laughter.

"Ohh ha.. ha.. I don't know... the girl with the dick?"

"Why," she whispered.

"B-because... I don't know. I wouldn't be attracted to the man either way... but I could still find the girl beautiful...."

She seemed to glow at this summary.

"Okay great... your turn!"

"Right.. Would you rather... uh... be with a tall guy, or a short guy."

She snorted, and Billy shuddered as he thought about the stupidity of the question.

Who says short?

"Short."

Billy couldn't keep the smile from his face, turning from her so that it wasn't so obvious.

"Why you smilin'?" coaxed Meana, nudging him in the ribs, and he nudged her back, leading to them scuffling together as they teased each other back and forth.

He could almost see the entire side of her breast, the nipple tantalisingly close to being revealed as she slid up against him.

When they had finished they were firmly ensconced together on the sofa.

"Your turn."

She was so close that he could see the tiny imperfections, a minute hair on her cheek, a tiny red mark which looked like a popped spot near her jaw, which somehow just made her even more beautiful.

"Okay... if I had a dick, would you still find me attractive?" she teased.

"Oh... you? Of course, I hope it's a big one," he joked.

"Oh look at me, you know it's going to be big," she giggled, "and definitely bigger than yours."

He winced until she leaned in close and pecked him on the cheek. "Just the way I like it."

Warmth spread from the place where her lips had brushed his skin.

"Erm... would you rather...."

It was quite tough to think when she was so close, and now he was picking up hints of a jasmine perfume that was intoxicating his brain.

"I'll go again," she said firmly, Billy's heart beating so hard it felt like it was about to take a running jump and smash through his ribcage.

"Would you rather have anal sex or regular sex?"

He cocked his eyebrow.

"Do girls even like anal?"

"Depends on the girl."

"Oh come on, why don't ALL girls just do anal if it's so good!"

"Like I said, I think it depends on the girl... or boy, silly."

"That's Billy actually."

"Oh, sorry about that."

She bit her lip at his lame joke.

"...Silly."

He grinned back.

"WELL, my friend said she hated it. I'd bet you anything that girls just fake it because guys say they like it."

A curious look crossed her face.

"You know guys can enjoy anal just as much as girls."

"HA, no way!"

Her lips pursed, mulling something over.

"Well look, for a hundred dollars, I reckon you wouldn't even be able sit on my cock for five minutes without enjoying it."

Billy spat his drank out over the table, and someone nearby hiccupped as the people closest to them froze midway through their various discussions and turned to look at the young man who was staring at Meana with a stunned expression.

All of a sudden she felt incredibly close, inside his personal space.

"Sorry... what?"

He wiped his face, still looking like a ghost as he gazed into the relaxed face of Meana, smiling at him with glossy pink lips.

"I said... for a hundred dollars, you wouldn't last five minutes on my cock without enjoying it."

"Your... cock."

"Yes, I have a cock... problem?"

Billy looked at her in a new light.... This gorgeous woman had a penis.

The questions made sense now, but his brain couldn't equate what he was seeing with that fact. Those long legs were still so enticing, the way her dress gave flashes of her chest, so scandalously was it cut, and the milky skin that was open down the side, inviting him to explore further.

The boy's eyes flicked down to her mid-riff and lower, to where her legs were firmly crossed.

"Nope, if you want to see it, you'll have to do what I tell you," she whispered with a grin, squeezing her legs tighter.

If anything, he was getting even more aroused staring at her.

"Well uh.. no... no problem."

The walls still buzzed with the vibrations of the music, but some conversations near them had died away, and Billy felt the tautness in the air as others took in what was going on.

Meana didn't seem to care and leaned into him hard, pressing her cleavage against him.

"Take me to the bedroom and sit on me."

His mouth opened, not quite believing what was happening.

She had a penis.

"R...Really?"

"Yeah.... And you might get one hundred dollars as well," she added with a grin, "what's there to lose?..."

"Well uh... Yeah... right..."

He glanced around at people in various states of shock, disbelief, and sheer curiosity.

Billy didn't know whether he was excited, or scared, or aroused... it was a whirlpool in his head, crashing into the sides of his skull and fusing his lips shut.

Many people were watching, some whispering, others asking what had been said. For a moment it was almost like a restless theatre during a pivotal moment of a play as the news strange atmosphere spread around the room.

Eventually, the tension was broken by a girl at the kitchen counter who gleefully shouted "DO IT!"

Half the room exploded with laughter, and people began to join in with various cries and chants.

"YES!"

"SIT ON HERRR!"

"What?! Sit on what!"

"Billy's going gay!!!!"

The eyes of the whole room were on him, and everywhere he looked made it worse; A haughty couple murmuring things to each other whilst staring straight at him, the chad and the blond curled up with laughter, and one group of heavily made-up girls who seemed to be living their sex lives vicariously through the two of them, eagerly egging him on to seal a one-minute love story being played out in their heads, Alecia looking on weirdly with a few of her friends, a guilty expression on her face.

Billy's lip quivered.

"Urm....."

His response was pushed back into his throat by the feverish attention, but thankfully it was Meana who took control by enclosing his hand in hers.

All the sound disappeared because his mind was no longer listening to it, every neuron having been wrenched towards the feeling of being touched by a large, delicate hand.

Billy looked into the blue eyes of this Irish beauty. Her lips moved slowly.

"Follow me."

His mouth glazed open as she folded around his hand, so gently that at first he wasn't sure if she had put any pressure on at all, before grasping more firmly, and then he was being pulled to his feet.

The sound returned to his ears in a roar that crescendoed as he was led, red-faced, by Meana through the crowd of people frothing at the mouth, driven wild by the prospect of Billy touching a strange girl's dick.

"BILLY, BILLY, BILLY!!!"

"GAAAAAYYY!"

"AW THAT'S SO CUTEEE!!!"

The noise barely died down as he was led down a hallway to a bedroom, containing a queen-sized cream bed, lit by a small lamp on the table beside it.

He stumbled in and the door was slammed shut behind them by Meana, who gave a frustrated look behind them before lightening up as she let go of his hand, seating herself elegantly on the foot of the bed.

The sounds were muffled, but he could still make out the hoots and hollers of people as they processed what might be about to happen in the bedroom.

His eyes locked on with Meana's, this movie-star beauty in a gorgeous dress, sat on the edge of the bed, looking expectantly at him.

And she had a penis.

Billy didn't know what to do. He'd had sex once.. but that had been five minutes of him working out what a vagina felt like, and it hadn't exactly been the most life-changing of events. This?.. well, this was so far out of his comfort zone that even starting from zero was higher than where he felt at the moment.