The Bet

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Can he last long enough to win or will she prove too good?
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yesMadame
yesMadame
13 Followers

It's when he's standing on the doorstep behind her that the nerves set in, but he shakes them off a moment later. He watches her turn the key and look back at him as she steps into her house. He reminds himself he can back up the big game he was talking as she takes his jacket. He clears his throat.

"So, you seem pretty confident in our bet," he says.

"Trying to get right to it I see," she answers, "so eager! Doesn't bode well for you."

"Maybe I'm just confident too."

"I'm going to do you a favor get a glass of wine so you can cool off and relax," she raises her dark eyebrows teasingly and smiles, "come on in, have a seat"

"Suit yourself", he answered.

"Take of your shoes, get comfortable," she invited.

He takes of his shoes, but he's too flustered to relax. He follows her into the living room, and sits in a chair next to the couch. She disappears into the kitchen and comes back with two glasses of red and offers him one.

She sits on the couch, crossing her legs, letting her dress hug her thick thighs, and dangles one of her heels from her toes.

He tries to think of something to say, but he can't stop thinking about what's about to happen. He drinks deeply.

"Thanks for the wine," he said, increasingly aware that he's hard for her and has been for some time. He shifts in his chair trying not to give too much away. He notices she's grinning.

"What?", he inquires.

"Nothing," she says.

"Sure," he says. He's trying to play it off, but her legs and dangling heel are quickening his heartbeat and the idea that she's on to him puts him off balance. He is surprised to find himself even more aroused at this. His breathing speeds up.

"It's not working is it?", she asks, running her fingers along the pearl necklace that stands out charmingly against her warmly tan skin.

"What isn't working?" he answers.

"The wait. It's just getting you more excited, huh?". She sips her wine.

"I can handle it," he says, full of fake bravado. Another sip, a little too big for someone who's supposedly calm.

She looks at him knowingly and sips again, placing her glass on the coffee table between them.

"Alright then - let's go," she says.

"Really? What happened to my cooldown?", he shoots back.

"It's only making things worse, and I want to give you a fighting chance," she said with a confident smile.

"Whatever you say," he said, failing to sound sure of himself.

She pushes her dark hair off the side of her face and lets her dangling heel fall to the carpet as she looks into his eyes. He glances towards it on the ground and then back to her. She pushes the other off with her bare toes and kicks them to the side before standing up and walking slowly towards him. He flushes at the realization that this is really happening. He swallows nervously as he's undoing his belt, and again as she pulls his pants off. He hopes she doesn't notice. She does. She kneels. He swallows again. She notices again.

"We can still renegotiate you know - to the easier bet," she says.

"No need," he replies.

She'd been talking up her skills for some time before they'd gotten together. She claimed to have an irresistibly talented mouth and that she'd have him melting before he knew it. He said he'd met some pretty talented lips in his day so he'd was sure he could handle it. She'd surprised him by offering a bet - that she'd have him finishing hard in less than five minutes, tops. Caught off guard, he agreed. He'd gone so far as to double down, saying even ten minutes would be no problem for a seasoned player like him. Now, feeling the air on his cock as she slid his boxers down his legs, he was wondering if he'd gotten ahead of himself.

"You sure?", she teased, "Five minutes is a pretty long time - longer than you think. Guys tend to overestimate themselves."

She runs her tongue along the inside of her bottom lip before biting it playfully and grinning.

"I'm sure - do your worst. We'll see how confident you are in ten minutes."

"Okay then. I tried to warn you - beg all you want, I'm not cutting you any slack from here on out."

"There won't be any begging."

"We'll see. Did you bring it?"

He pauses a moment. He'd secretly been hoping she'd forget.

"In my left pocket."

He smiles sheepishly as she pulls a stopwatch out of the pocket of his jeans on the floor. She looks at him confidently and tests it out with a few clicks of the buttons.

"Looks like we're ready."

"Looks like."

She smiles and she starts the stopwatch with a beep, lets it dangle around her wrists, then looks him in the eye as her mouth opens slightly and the tip of her tongue starts to slide towards her lips.

He manages to stifle his first gasp when she wraps her lips and tongue around him, but just barely - the sudden warmth, the first pull of her tongue along the bottom, the first twist of her lips and she pulls her face away before plunging it back down. Confident, expert, irresistible. The pleasure is overwhelming and he's already begun to tingle. Her lips up and down him. A flick of her tongue. His already wavering confidence slips a little further away.

"No," he tells himself, "I'll settle into it soon, hit my stride."

She does it again, a drag of her tongue, a gentle rotation of her head as she moves up and down him. Over and over, the cool of the room then the heat and wet of her mouth. The smooth of her lips and the push and flick of her tongue. He notices he's breathing faster, tries to slow down. In, flick, twist, out. The muscles in his legs tighten. Her fingers squeeze back at them. His cock pulls back against the roof of her mouth. He exhales, more loudly then he means to.

His little moans flow against his will.

She pulls her mouth slowly along his length and pauses with his tip in her lips. She holds up the stopwatch where she can read it, laughs a little low in her throat without letting him slip out of her mouth, and turns it around so he can see. It's been twenty-nine seconds. His eyes dart nervously as he meets her gaze. He leans his head back and breathes deeply.

That's when he feels her fingers wrap around his balls and gently squeeze. He shudders - he hadn't even noticed she had put him into such a state without even using her hands. In, flick, twist, out. Her hand pushes up into the skin around his shaft and then pulls firmly back down on his balls. In, flick, twist, out.

"Ah - oh, God!", he blurts accidentally, "Your hands..."

He hears a self-satisfied moan that gently vibrates the lips around him. She slides all the way down him and finally lets him out of her mouth for the first time with a soft pop.

"Oh darling, I'm only just starting!", she says and she dangles the timer. Forty-six seconds. "You're not struggling already, are you?"

He lets his breath out slowly. He opens his mouth to answer when she suddenly squeezes him - he only groans.

"It's a long way yet to ten minutes hotshot," she says softly.

She smiles when he doesn't answer, and pulls him back down onto her tongue. The cool of the air on him fades into the warmth of her mouth - it feels devastatingly good - and any stamina gained during the pause from her mouth melts away on her circling tongue. In, flick, twist, out. The tingling in his cock keeps growing.

"I can do this," he tells himself, "I'll just think of something else."

Suddenly he's gasping again. He's not even sure what she's doing to him but there is a new, perfect pleasure, a pressure on the bottom of his cock that's overwhelming him, pushing the tingle further from his control. He realized she's wrapped her thumb and finger around him and is punctuating the drags of her lips down his cock with a brief, perfect squeeze around the middle. He's especially sensitive there, instead of where most guys are, at the tip. He'd thought this would be an advantage against her but his grunts and moans gave him away and she expertly felt her way around him, noting every gasp and twitch, learning to make him helpless. He's losing control of the muscles behind his balls and realizes his toes are curling inward. He tries to relax - tries to keep himself from bobbing back to the top of her mouth, from making himself throb even harder.

Her hand slides further down him and lets go for a moment.

"Good." he thinks, "I needed a little break - I'm still in control of course, but she is good."

He remembers the timer. How long has it been since forty-six seconds? He's trying to convince himself it's been at least another forty-six seconds when her hand reappears - ever so lightly, fingernails dragging lightly on his balls.

He says her name before he realizes what he was doing.

"Oh God, keep it together," he thinks, then says her name again.

The soft pop of her letting him out of her mouth again.

"I like the sound of that," she says.

He says it again before he can stop himself.

"Too easy," she says smiling.

The break from her mouth is ruined by her hands again - one pulling hard on his balls and the other switching between tight, twisting, up-and-down jerks and slow, delicious squeezes.

"Fuck.", he says, "How much longer?"

She glances down, smiles, and says, "I'm not going to tell you."

"Please?"

"Begging already? Delicious! It wasn't long ago you said you wouldn't be doing any."

"How much more?", he asks tensely.

"Let's just say you wouldn't have even won the easier bet yet."

"Fuck."

"Are you gonna make it?"

"I..." he stammers.

"Are you going to cum too soon?"

"I..." he stammers again.

"Hmm?"

"I...", the muscles behind his balls clench and steal his words.

She waits a moment before pushing him, "Answer me, hotshot."

She raises her brow expectantly. It's a small but somehow viciously hot gesture to him - she's in control, waiting in calm expectation - signaling subtly for him to speak as if he hadn't heard her - confident, even condescending.

"One more time..." she says slowly, softly: "Are. You. Going. To. Last?"

"Yes!" he stammers, as she pulls down on his balls and twists his shaft, dizzying him.

"Ok, hotshot."

Again the cool of the room fades to the hot, wet, twisting, lips and tongue. In, flick, twist, out. Her nails on his balls, the squeeze in the middle. Again, again.

Then her rhythm changes. The long, slow, deeply pleasurable strokes that had been melting him change into short, fast ones, right on the center of his cock. She'd gotten him dangerously aroused; now she was trying to finish him. He yells in pleasure and surprise. It doesn't feel fair. It was hard enough to resist the languid pleasure of her skilled mouth making its way all over him, harder still with the confident and precise squeezes of her fingers joining in concert. It felt like cheating to use them both on a weak spot at the same time, one he'd never even told her about. Now he knows: he isn't going to last. He moans her name.

"Okay!" he gasps.

The soft pop. The pleasure, hot and full, switches from the ruthless tongue to her hands, harder now, in tight, fast, up and down jerks, the same finishing rhythm. She's looking him in the eyes. He loses control. He surrenders. He feels his cock pulse and tighten, then open wide with pleasure, and he loses his breath. The tingle rips through his cock as he pushes the first shot of his load into the air. Her eyes and mouth widen in excitement that he knows isn't surprise as his cum flies by her face.

She drags out the words as she teases: "Really? It hasn't even been two minutes!"

He hears the beep of a stopwatch as pleasure surges through him and the second shot is pushed from his helpless cock. Two minutes? He'd try to tell himself she's lying but he can't focus, and he doesn't care anymore. Her smile as she plunges her mouth over him. That tongue. Those lips. Those fingers. The tingle, the burn of pleasure. Another pulse, another shot, into her mouth. A rush of heat and dizziness to his head. Another pulse, another shot, on her tongue. Squeezes, drags, more squeezes.

He's looking at the ceiling as she slides her mouth off of him. The soft pop. The cool of the room. His breathing. The lingering tingle and pulsing of pleasure. "Oh God!" he hears himself say. Her giggle. Some moments pass.

"Well?" he says.

"Well what, hotshot?"

"You know."

"I don't," She wants to hear him say it, to ask.

He sighs, more than aware of what she's doing, then gives up and indulges her, "How long?"

Her giggle, her expectant, condescending face. She wants to maximize her power over him.

"How long what?" she teases.

His ears burn.

"How long did I last?"

She holds up the timer and he looks down at his lap. Humiliated, but unable to keep from smiling somehow. "Wow - well, I have to admit - you are something."

She's not letting him off that easily.

"Why don't you read it out loud?"

He pauses, then blurts, "One minute and fifty-five seconds."

"And you were supposed to last..."

"Ten minutes."

"Wow, hotshot. Looks like you've got a ways to go!"

He looks away shyly a while before meeting her gaze.

"Maybe if you practice real hard you'll be able to handle me a full two minutes!", she says winking. "Now remember our arrangement - what are you going to say whenever I ask if you cum too quick for me?"

"Yes Madame," he says quietly.

"Good. Now get on your knees."

yesMadame
yesMadame
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AnonymousAnonymous2 months ago

Good premise.

Needed to slow down.

Needed dialog during blowjob.

Needed her asking him how he liked what she was doing?

Needed more playing with his balls, and details about his reaction/s.

Four stars.

MidnightHour_MidnightHour_about 1 year ago

More please! This was great!

AnonymousAnonymousabout 1 year ago

Love stories about premature guys. Especially love the detail given to his pathetic cock’s reactions to her ministrations. Keep up the good work!

yesMadameyesMadameabout 1 year agoAuthor

Thanks for pointing those out. I did reach out to a proofreader or two but never heard back. Maybe I'm just asking the wrong people.

I'll submit and edit at some point and take another stab at finding a proofreader.

MigbirdMigbirdabout 1 year ago

Clever, fun short piece; like the anonymity, her sassy demeanor and tumescent pace — builds nicely while retaining whimsical quality. Couple of places long sentences, while wonderfully descriptive, momentarily deflating. Loved last line — can only imagine. Hope you continue to share your vivid imagination. 5 🌟

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