Tiffany and Mike

Story Info
Cheerleader and baseball player make a bet.
1.8k words
4.6
17.6k
27

Part 1 of the 2 part series

Updated 01/11/2024
Created 01/03/2024
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"There's no way you're going to do that," Tiffany coos as a sexy smile crosses her lips.

Since we met in the fall, we've had a close friendship with a hint of sexual tension.

"Wanna bet?" I smugly reply.

"I will bet anything," she giggles twirling her blonde hair.

"Name your wager," I calmly answer.

"You really think you're gonna win this bet?"

"Yep."

"Ok fine," she says sitting back in her chair. "If you hit three home runs on Friday, then I will pay for your car for six months."

"Ok," I nod my head, imagining not needing to pay for my car for six months.

"But," she says with a snap of her fingers "if you don't," she says with a wild look in her baby blue eyes "then you have to be my sex slave for spring break."

"W- what," I stammer.

"Since you're so confident then let's have some high stakes," she says extending her hand.

"That was just a bit unexpected," I giggle.

"You said 'anything,'" she grins. "Put your money where your mouth is."

"I know I did, but I didn't think you were going to go there," I say as she crosses her arms to press her breasts together.

"Oh please, I've seen you checking me out in my cheerleading outfit," she smirks. "You can't honestly tell me that you don't want this," she grins.

For a few minutes I stay silent.

"We both know you want to fuck the hot cheer captain, here's your chance to show me you deserve it," she grins. "Unless of course," she cocks her eyebrow. "Your scared," she extends her hand.

"Deal," I shake her hand.

--

My first at bat is in the bottom half of the first inning. The cheerleaders are doing their routine next to the dugout and I glance over to Tiffany. She flashes three fingers and winks as I walk to the plate.

First pitch, fouled behind home plate.

Second pitch, backspin. Fastball down and in. Turn on it and hit it over the left field wall.

When I enter the dugout, I flash two fingers to Tiffany.

-

Second at bat, bottom of the third inning. Two outs, runner of second.

First pitch, line drive to center field caught on the run.

Tiffany sticks her tongue out and flashes two fingers as I go back to the dugout.

-

Third at bat, bottom of the sixth inning. One out, runners on the corners.

First pitch, in the dirt.

Second pitch, high and outside.

Third pitch, slider not breaking. A towering flyball to center field. Track... wall... gone.

I flash one finger at Tiffany in the dugout.

-

Fourth at bat, two outs in the bottom of the eighth inning with the bases empty. Last chance to win my bet.

First pitch, breaking ball low and away.

Second pitch, fastball fouled down the right field line.

Third pitch, cutter low away.

Fourth pitch, fastball high and away.

Fifth pitch, slider belt height. Line drive to right field, well hit but not carrying.

Right fielder calls "Got it," and closes his glove around the ball as it drops.

I walk back to the dugout and make eye contact with Tiffany. She licks her lips and holds up one finger.

--

A couple hours later I'm sitting in my car outside the school. I'm browsing social media and listening to music when there's a knock at my window passenger window. I look to see Tiffany and unlock the car.

"How'd the game go?" she smirks. "Did you hit three home runs?"

"No," I sheepishly reply.

"Oh," she giggles. "Looks like you're going to be my sex slave."

"Yeah?" I whisper. "A deal's a deal," I nervously say.

"Are you sure you want to do this?" she asks.

I don't speak as I look down, not sure how to answer that question.

"You don't have to do this if you're uncomfortable," she softly says putting a hand on my shoulder.

"No, I loudly say. "A deal's a deal."

"Good boy," she grins. "Come by my place tomorrow morning," she leans in and kisses my cheek.

"But break-," I begin saying before she gets out of the car. "Doesn't start for two weeks," I quietly say to myself.

--

The next morning I make the drive to the address Tiffany sent me the night before. I know her parents rented out a house for her so she doesn't have to live on campus but I haven't been here before.

I walk up the porch and knock on the door.

"It's open," I hear Tiffany call.

I hesitantly open the door and see her sitting on the couch. She's silently staring at me in a red shirt and sweatpants.

"Hi," I nervously say.

"Sit down," she pats the couch next to her as I shut and lock the door.

I sit down and look at her, unsure of what to say.

"Look, I'm not going to bullshit you," she confidently says. "We both know you have to be my sex slave for spring break because of our bet," she pauses and looks at me.

I nod.

"But I saw the way your eyes lit up when I made that the bet," she smirks. "You want to be my slave," I feel my breathing pick up. "And you don't want to wait until break," I begin fidgeting on the couch.

I've never heard the authority in her voice she's speaking with right now.

"Umm...I...well," she puts a finger over my lips and brings her face closer to mine.

"I don't want to wait until break either," she says in a much softer tone. "If I'm wrong and you do want to wait, please tell me now."

"You're not wrong," I nervously say breaking eye contact.

"Don't be embarrassed," she says cupping my chin. "You're here because I want the same thing you do."

"You do?" I ask.

She nods. "That's why I made it the bet, I didn't think you would ask me out." She puts a hand on my shoulder. "Mike just relax, I'm not doing anything to you right now. Just breathe. Stop stressing yourself out."

Without thinking I run my hand through her hair and lean in, kissing her deeply. I feel her run a hand up and down my back as we kiss. When we break apart, she has a sexy smile on her face.

"I've wanted to do that for so long," I whisper.

Me too," she says caressing my cheek. "Now that you're a bit less stressed," she grins and leans back into the couch. "We have to go over some rules."

"Rules?"

"For both of us," she answers. "Have you ever done something like this before?"

"No."

"Me either, so we'll learn together.."

"Learn?"

"What we both like," she says taking out her phone.

--

We spend about an hour on the couch eating breakfast and talking about what we're both open to trying.

"Anything we missed?" she asked sipping her coffee.

"Not that I can think of," I answer.

"So," she says " since neither of us want to wait to start this," she stands up "come with me," she extends a hand.

I almost jump off the couch to take her hand. She leads me to her bedroom, opening the door and gestures for me to enter.

I walk in and she wraps an arm around my waist, turning me around and kissing me again while pushing the door shut.

"Ooh baby," she moans running a hand over the bulge in my pants "is that for me?"

"Yes," I moan into her mouth.

"Good boy," she moans undoing my belt. "Turn around," she says yanking the belt off of me.

I turn around and she pushes my against the wall, yanking my arms behind me and tying my belt around my wrists.

She turns me around and kisses me, again running a hand over my bulge.

"Where did you learn that?" I groan into her mouth tugging on my belt.

"Pinterest," she snickers and unbuttons my jeans. "You ok?" she asks breaking apart. I nod and she slowly unzips my jeans, letting them fall to the floor.

I step out of them and she continues to tease my throbbing cock through my underwear.

"Baby, please don't tease me," I whimper as my cock begins to leak. She wraps her arms around my waist and guides my to her bed and shoves me down on onto her bed.

"Oh I'm going to tease the shit out of you," she smirks sitting on the edge of the bed next to me.

After a few more minutes of teasing, she pulls my underwear down and allows my cock to spring free.

She lightly strokes my cock with two fingers for a moment before leaving it to throb in the air.

"Please fuck me baby," I beg as she leans down and kisses the top of my cock.

"I can't do that just yet," she chuckles. "Then you lose your incentive for pleasing me," she says as she gets off the bed and opens her closet.

She takes a small box out of the closet and puts it next to me on the bed, sliding her pants off and sitting next to me.

"So," she says taking her top off. "We both know what's in this," she says tapping the box. "Do you want to do this?"

"Yes," I choke out.

She leans down and kisses me, running a hand across my chest.

"Pick a word," she softly says.

"Fastball," I say looking into her eyes.

"Good boy," she says. "Unless you say that word now, I own you and your pleasure." She gently pinches my nipple. "Is that clear?"

"Yes," I choke out.

"Yes what?"

"Yes it's clear," I yell.

"Who are you saying 'yes' to?"

"Yes Mistress," I choke as she finally releases my nipple.

"Good boy," she says opening the box.

She take the three rings out of the box and slides the smallest one of my cock, gently forcing my balls through it.

"Do you want to wait until you go soft or can I ice you?"

"You can ice me," I say squirming as she walks into the bathroom.

She struts back into the room and ices my cock for a few minutes before sliding the cage up my cock.

She takes out a heart shaped padlock and lets out a slight moan as it clicks it into place.

Nothing happens for a few moments, as I lie there and feel my cock twitch in its new confinement.

After a minute she turns me on my side and frees my arms from my belt, massaging my wrists.

I lean in for a kiss, sliding one hand up her naked back. She gently guides my other hand to her breasts.

"Feel 'em babe," she chuckles as she reaches back and undoes her bra.

I massage her breasts for a few minutes before we break apart and I look down at them.

But my attention is drawn away from her breasts.

I see a small silver key in her cleavage.

I look up and see a smirk on her face as she stands up.

"Get dressed," she says sliding her pants back on.

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AnonymousAnonymous4 months ago

Interesting premise.

But what sex there is nothing more than an outline. Totally lacking in details.

Two stars.

rentturtlerentturtle4 months ago

oohh good start. excited to see where this goes.

spinpole2001spinpole20014 months ago

I can't wait for more chapters!

chrono_h3chrono_h34 months ago

I agree with the comment od Norway_1705. Don't let this drop into the typical and cliche story. Great start so far, maybe could have added a bit more of the background of how they found themselves kinky. Better than many out there already.

AnonymousAnonymous4 months ago

Boy I sure hope this isn't a one and done story, because it such a good start to a good story..

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