The Bet

As if waiting for a command from a drill sergeant he simply stood there as Meana scanned him up and down, apparently appreciative of his rather plump ass, weedy arms and soft demeanour.

Her right leg bounced on top of the other, almost touching his.

"Come here."

He obeyed, walking past her long limbs and making to settle on the bed next to her, but before he could hands shot out and grasped him at the waist, and he found himself being cajoled into a seated position on her lap.

It was rough, but the playfulness in her smile, the way she giggled as he tried to resist, acted like a muscle relaxant, and he found himself easily moulded onto her lap like clay putty, staring into her face.

The blue in her eyes was flecked with grey, and they shifted subtly, clearly taking in his own, rather dull brown ones.

As the quietness descended, it became just the two of them.

His heart was beating fast, and her thighs underneath his ass were quite comfortable and pillowy, although occasionally she would shift slightly, quads bulging, exposing the strength in her legs. Even though he was now in quite a submissive position, it didn't terrify him as much as it should have.

"Do you know your eyes shift from light to dark, the close they get to the edges?"

Billy looked at her in surprise.

"Uh... no?"

"Well, they do... maybe because there's lightness in your centre."

She pressed two fingers to his heart.

"Lightness? We just met.." he murmured.

"Yeah, but I just told you I have a dick in front of a room full of strangers, and you followed me into a room in front of them all.... Men don't often have the balls to do that."

Immediately he found himself rethinking the whole thing.

'What if I made the wrong decision?'

'What if people think I'm gay... what if I'm gay?!?!'

Meana quietened his thoughts with a thumb stroked on his cheek.

"Listen, stop thinking about it. If you're nervous, just tell yourself that you're doing it for the hundred dollars."

"Huh?"

He'd forgotten about the hundred dollars.

"Oh, yeah... right..."

A look of bare-faced joy flitted across her features as she realised his confusion, and it was with anticipation that she shuffled her dress up.

"Okay, time for your first look.... Excited?"

Billy had never been more excited... or scared, or confused... His brain seemed unable to reach a verdict on his feelings, and now the think pipes were bursting, battery fluid leaking into the word generator, saliva-producer locked on high-fluid leading to him swallowing large globs of spit as he watched her hands reached underneath and pull out a long, pulsing shaft from under her dress.

It was ten inches, a solid man-shaft that completely surpassed his pathetic excuse for a cock. The thick, flared mushroom of her cock-head was twitching upwards every few seconds or so, and it wasn't difficult to work out how aroused Meana was by the way it bobbed in the air.

If it wasn't enough to see her helmet looking up at him like a hungry snake, the gaze that she had fixed him with was nothing short of starving.

"Why don't you put your hands on it... get to know it better."

Before he could protest, she had clamped her hands to his wrist, and led them obediently on her shaft.

The first touch of another person's cock was electrifying, and terrifying.

The ligaments inside were so hard they were like building foundations, pillars of taut tissue that were intimidating to say the least, not helped by the way Meana's chest was rising and falling more heavily in front of him.

Touching hers was nothing like touching his own. Not even the same ballpark.

This was... exhilarating.

It was hard not to notice that even though he was sat on her legs she was still taller than him. Now he looked up at her, hating that he also wanted to keep staring at her cock, fingers betraying him with a tiny flutter up the sides of her shaft.

The heat of it was incredible, and Meana uttered a small moan.

Then his fingers reached up to the ridge.

Billy couldn't do it. The head was just too scary to touch, and as soon as he felt the softer texture he whimpered and drew his hands away.

"Shhhhh, it's okay, it's okay," murmured Meana, rubbing her hands on his cheek. "You won't have to do anything crazy, let's just take it slow."

He looked up into her, and either she was a phenomenal actress, or her kindness was something that almost glowed.

"Now, let's just do the scary bit... and then we can relax," she said.

The way she described it together, 'let's', and 'we's', made him feel like this was a joint venture, despite Meana having led him here like a dog on a leash.

"Okay," he muttered, and she gave a little giggle, reciprocated by Billy as she reached for her handbag.

"Now, don't panic but... we're gonna be using a lot of lube."

"Right...Sure.."

"Trust me... you don't want to try this without!"

He nodded, a puppy waiting for its master to give it a treat as she uncapped a plastic bottle and began to pour clear liquid on her dick like she was applying chocolate sauce to an ice cream.

"Wow, that's a lot," muttered Billy, his eyebrows rising as he watched her dollop nearly half the bottle in a lube waterfall that spread onto her legs and ran onto the bed.

"Yeah... want to help me spread it out?"

He wasn't sure about touching it again.

"Erm... Maybe..."

"It's okay," she said, giving him a sympathetic look, "like I said, you won't be doing anything you don't want to."

The way she treated him was so gentle and un-confrontational that Billy couldn't help but feel relaxed, even though in reality he was sat on the lap of a human far stronger than him, whilst she lubed up her cock in preparation for entry into his asshole.

The squelching, sliding custard sounds were loud in the tense silence as she stroked a tight fist up and down her cock, spreading the lube nice and evenly, until the cock looked like a strange alien, something alive in its own right, hungering for his insides.

Meana looked down at her hand, drenched in lube, lost in her thoughts for a moment.

"Billy... I'm going to unzip your pants now."

Billy's hands were shaking as he nodded.

"Good," she smiled, taking her free hand and removing the front button of his trousers, slowly unzipping down to reveal a bulge in his boxers.

"Oh, such a good boy," she said, watching his blush intensify to radish-like proportions as she brought her large hand to the front of his underwear, rubbing the meagre tent.

"Are you getting excited for me?"

He didn't even have the courage to answer her, trying not to look her in the eye as she teased the fabric, making him whimper.

"I'll take that as a yes...."

The bulge throbbed in agreement.

"Take your shirt off."

The shirt was lifted and thrown aside by shaking hands, revealing a milky chest, no hair, and a smooth stomach with only a suggestion of abdominal muscles beneath it, mainly due to his lack of fat rather than any strength to speak of.

Meana nodded approvingly.

"Sit up a little."

He sat up and they manoeuvred to pull off his jeans, throwing them aside, and then she put her thumbs into the waistband of his boxers.

The tension rose in his chest, and Meana gauged the situation carefully, slowly lowering the fabric, until Billy's 3-inch erection bounced out of its comfortable prison.

Meana cooed at his beautiful little penis, which stood tall, not a fear in the world when presented with its far superior compatriot. She caressed it with her hand, making it look almost childish in comparison, lost in her large palm and fingers.

Its owner was the opposite of proud and erect, consumed with embarrassment as Meana drank in his most shameful appendage.

"It's..... sorry..." he whispered.

"It's beautiful," said Meana, and when she looked at him, it was with such passion that it was hard to tell whether she wanted to kiss him or kill him. "You're beautiful."

The words reached him at a deep level, despite the exposure that was still there, the feeling of a stranger observing something that he hated about himself, and had been taught to hate by laughing emojis and reddit forums.

Being told he was desirable pushed it all aside.

Then a hand drenched with lube grasped his package, and Billy mewled as the woman began to slather his entire undercarriage in it, stroking up and down his manhood and even fiddling with his balls a little, making him coo.

Meana looked at him and smiled.

"Oh... I almost forgot..."

She took her free hand to her dress and pulled it up and over herself, revealing a sight that made Billy swoon.

Smooth, pretty, B-cup breasts were revealed, enough to fill his hands, which is what he desperately wanted to do.

"Would you like to feel them?" she asked, prompting him in an obvious, teacher-like way.

His hands moved up and pressed her chest, and their collective heavy breathing was loud as he felt her nipples pressing insistently into his palm, demanding attention. He sated them with slow rotations of his wrist, pushing them left and right, up and down.

"Hohh yeah, that's it," she breathed, eyes closing as Billy's hands became more eager, more insistent.

Her hand, stilled coated with some lubricant, slid under his, coating her tits in a warm coating of transparent gel that made everything easier to rub, slide over, and fondle.

He began to tweak the wet nubs, which were now hardened points, screaming at him for more.

Before he could think his mouth had entered the picture, closing around one of her tits and sucking greedily, searching for milk.

"Hoohhhh good boy, you're a very good boy," she groaned, as he suckled at her breast.

A hand snaked carefully through his hair, closing there, careful not to spook the young buck as his tongue rolled over her pink areola.

Billy felt something warm and wet pressing into his midriff, and tried to ignore it, even though it was like trying to kiss around a sticky bollard, and he engaged in an awkward rolling of his stomach to try and push the thing away, which only made it bounce back and rub slime against his sternum.

He gasped, hands coming up to protect himself, enclosing them around that huge meat now wet with lube as he withdrew his lips from her teat.

Billy was sat on Meana's legs, with her huge lubed up cock in his hands.

He noticed the way she was enjoying his touches so much that it was almost painful for her, engaged in a heartfelt battle to keep her arousal in check.

The saliva that had been steadily feeding into Billy's mouth went into overdrive, trying to submerge his tongue as he came to grips with the woman who clearly wanted him, feeling the blood pump through her pleasure vessel.

"It's time," she uttered. "Would you like me to set a timer?"

Confusion spread across his features.

"What?"

"Oh, nothing."

"Uh... OH!.. the timer... yeah... yeah five minutes... sorry."

Meana couldn't keep the aggravation from her face at having accidentally reminded him of the bet, before plastering it up again with a nod as she reached for her phone.

"I'll start the timer when you're sat down, okay?"

"Sure."

There was a second where nobody moved.

"Well... go on," she prompted gently.

Billy couldn't believe he was actually raising himself onto his knees, over Meana's horsecock.

He shouldn't be doing this.

"Sit on me," she said, fervently.

Billy's heart pounded in his chest... and he lowered himself down.

The first thing he felt, was a giant, spongy baseball bat press against his entrance. The second thing he felt was that this was ridiculous, and it would never possibly fit inside him, and they might as well call it a day.

"What... Urm... am I supposed to... open up, or something?" he muttered, unsure as to how to proceed.

Meana didn't tease, taking his arms and placing them on her shoulders.

"It's fine, it just needs a bit of help, plus you need to relax."

"I..I am relaxed."

"Then why is your butthole as tight as a nun's cunt?"

This made him laugh, automatically relaxing his ring, and as it did, Meana pulled his shoulders down, just enough to squeeze her cockhead into Billy's newly open anus.

Billy squealed.

"HOOOHHHhhhh!!!! Meana, MEANA.... I-it won't fit....!!!!"

The thing was widening his entrance to a circumference that it had never experienced before, as Billy scrunched his face up to try and deal with the sensations overtaking his lower half.

A whimper escaped his lips, and Billy pushed down on Meana's shoulders to pull himself off her weapon, but Meana grabbed his head before he could think, pulling him into a tight kiss as everything in Billy just let go, his asshole relaxing as her tongue went deep inside his mouth.

Meana had to fight every single instinct in her body to slam herself up inside him, coaxing fluid into his mouth as she moaned, a hum which reverberated through his head.

It was over too soon, Billy panting as she drew back, watching him carefully.

They both stayed like that, eyeing each other, as Billy's panicked breathing slowed to less jerked, but still heavy, expansions of his chest.

The thick head sitting snuggly in his asshole hurt a lot less than it had before the make-out session, although it wasn't what he would define as 'pleasurable'.... But he was more concerned with trying to get another kiss, leaning forward to prompt another wave of making out.

A finger pressed against his lips, halting him in his tracks.

"Not until you're sat down like a good boy."

Billy sniffed, steeling himself as he realised what he must do.

'Don't think about it. Just sit.'

"OHHhhhh," Meana moaned, as the boy sank himself down a few inches further onto her shaft.

"HHNnn!"

His face became even tighter, eyelids screwed shut, and Billy found himself wondering how anyone could even achieve this, let alone think it was enjoyable.

Currently the hundred dollars was sounding quite unreasonable.

"HUMnnnnnuhhh!"

It was fortunate that Meana was incredible to look at, even if she was re-arranging his internal organs, and her little cooes and strokes of his cheek helped him swallow the difficulties of his predicament, her perfect lashes fluttering as she clearly enjoyed the feelings Billy was giving her, bright, glossy hair reflecting the glow of the bedside lamp.

"Good boy... Goooood boy..."

When she spoke to him like that, the uncomfortable feelings didn't seem so bad.

Her hands pressed on his shoulders again, and Billy whimpered as he was guided down another few inches.

"You're almost there," muttered Meana fervently, "Oh you're gonna love this, I promise."

Billy didn't believe it to be the case, and mewled as she grasped his hair and forced him down the final few inches, the heat and wetness of her cock alien to his sensitive insides, suddenly overpowered.

"H-..HUUUNNNnnn!!..."

Billy spasmed as she filled every last pocket of his insides.

"There, you're so good, well done," she hissed, marvelling at the way his anal tract hugged her cock from top to bottom, unable to contain her joy at the feeling of his body wrapped around her womanhood like the tightest pussy imaginable.

The smell of sweat was beginning to fill the room, and he whimpered as a tiny pocket of air escaped his ass in the form of an audible 'pfft' which had Meana giggling.

His feeling of total humiliation at having quietly farted whilst sat on a dream woman's cock was not reciprocated by Meana, who seemed positively delighted at his emasculation.

"Oh, that happens sometimes," she giggled, "now.. I believe you earned a reward."

She grabbed his face and Billy moaned in relief as she kissed him, savaging his face in a way that was so aggressive that he found himself sucking her tongue in the most submissive way possible.

The taste of her was indescribable. Sweeter than the sweetest nectar.

She pulled back and her teeth grazed his lip, teasing him with another potential world-class kiss.

Billy didn't know where to look, what to do..... the huge stick inside him was distracting him in a way that wasn't as painful as it was before.

Meana pressed her forehead against his, eyelids fluttering as she smiled, clearly ecstatic at having forced her way inside him.

"Sh-shouldn't we start the timer," he managed to utter.

Her face fell a little.

"Oh yeah, sure" she muttered, grabbing her phone and snapping through the lock screen quickly.

"Is this alright?"

She showed him what looked like an ordinary timer app.

"Y-yeah..."

She turned the screen back to her, tapped it once, then locked it.

"Five minutes."

They settled into a less-warm stare.

Being filled felt so weird.

He was sitting on a cock, and it was throbbing so hard against his inner walls that little stimulations were taking place all the way up his torso, emanating from that huge rod inside him like a reverse lightning conductor, infusing him with a build-up of energy.

Meana wasn't smiling any more, her lip quivering, and one of her eyes was spasming just a touch. It was so incredible to see the loss of control on her face, and Billy realised he was probably doing the same, because his jaw was clenching every time a little zip of electricity hit his spine, his cock much more open in its arousal, leaking a little bit of pre-cum onto Meana's belly.

She looked down, then back up at Billy.

Her expression was a knowing one.

"So... I guess you must not be feeling anything right?"

Billy's eyebrows rose.

"Huh?.. uh... not... uhhnnn!.. n-not particularly...."

Billy couldn't help his face reddening, feeling see-through as Meana's face lit up.

Statements of nonchalance don't work when you moan halfway through.

"Damnit... I guess you're right... no self-respecting person would enjoy having a dick in their ass," she said with a grin, as warm pre-cum dripped from Billy's dick onto her belly button, some of it catching on the lip, forming a tiny pool of cum in the crevasse.

"Y-yeah... that's right," Billy squeaked, before one particularly beautiful throb from Meana's cock set something off in his insides that he had absolutely no control over.

"HUUUNnnn."

"I'm sorry, what was that?" grinned Meana.

"Humm.... Nothing, it was nothinnnnHGGGGHHHHH!" Billy moaned into her face, as an accidental shift of his hips hit something deep inside that definitely wanted to be hit again.

"Oh, it seemed for just a second like you enjoyed it," breathed Meana, enjoying the boy spasming on top of the cock buried inside him.

"OHHHHHhhh... n-uuhhh!" he squeaked as some warm liquid leaked from her cock and into his insides.

"What?" she said innocently, "something the matter?"

Billy's knees were quivering, and he held onto Meana's shoulders as something in him gave way, searching for a sitting position which didn't stimulate anything, which only ended up stimulating more things.

"Huuhhhhhhnnn!" he groaned, a fresh wave of pre-cum dribbling down the sides of his cock, and Meana drank in the boy breaking himself on her like he was sat on the most invasive vibrator in the world.

"Look at me," she said gently, and Billy rested scared eyes on her as the heat building up in his body overpowered his brain, taking in those gorgeous features now locked on his like he was in the finale of a five-year soap opera, and every second was spellbinding.

"Ride me."

Billy squealed as something wonderful happened in his insides, tears building in his eyes as he tried to resist.

"H-how long leftttnghunn!"

She snorted, rolling her eyes as she searched for her phone, pretending not to find it as Billy spasmed on her cock.

"It's th-there!!" he gasped, pointing to right next to her.

"Oh yes, silly me," she muttered in a fake-surprised voice, picking it up and unlocking it slowly. "Oh that's not the password... what WAS it...."