Pantsing and Stripping Forums

A/N: The third story in Jennifer's "The Smash Bet" universe. Jennifer has been dating Josh for a while now, but for some reason, he still hasn't introduced her to his friends. When Josh relents and lets her come to Halo Night, Jennifer tries to make it all about her. All Josh and his boys wanted to do was play some games and drink a few beers. When they've finally had enough of Jennifer's antics, they make a bet she's going to regret.

Much thanks to Executionus for the idea behind this story.

The Smash Bet - Story 1
My Sister's Boyfriend - Story 2
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Part 1

I make bad decisions. I know that. But sometimes, lying is the most fun a girl can have without taking her clothes off. Okay, maybe not that much fun, but it’s up there. I promised Josh I’d wear something casual and chill tonight, but I fibbed. Even though he won't admit it, I think he wants his friends to know that he’s dating someone sophisticated, fashionable, and most importantly, hot. And me personally, I want to impress his friends, too, and make them a teensy bit jealous. It’s all in good fun.

I’m standing in front of my long mirror again admiring my cute outfit. Black crop top, liquid leather leggings, and short leather boots to match. I look good. Tall, powerful, dominant. I have no doubt that this is not what Josh meant when he said casual, but he knows that’s not my style. I’m too wild and flamboyant to let myself be tamed like that.

I admit I’m coming off as a bit self-absorbed. Okay, a lot self-absorbed. I doubt most people spend this much time checking themselves out in the mirror and making sure their outfit is just right. I just care about my appearance. Is that so bad? Pride, conceit, conscientiousness, they’re all just different words to describe being awesome. And I am, without a doubt, awesome.

Yes, I think this outfit will work. It shows off just the right amount of midriff.

I need to look good tonight, because I'm headed to Josh's place to meet his friends. We’ve been dating for a few months, but for some reason, I’ve never actually met any of his gaming buddies. It’s been too long and we’re getting too serious for that. I told him I’m tired of being his little secret. Well, he finally relented. He agreed to let me join him tonight.

I don’t know why he’s so hesitant about this. I’m pretty, friendly, and fun. He’s being silly. I’d think he’d want to show his girlfriend off a bit, you know? But whatever. It’s fine. I’m happy to make his friends a little envious and curious about what is behind this little crop top. It gives me some pleasure knowing that they’ll all be wishing they were Josh.

I love being the object of attention. Especially amongst a bunch of boys that are sixes and wish they could have something like this. I admit, again, conceited, but it turns me on to know that I’m... what’s the word? Unobtainable. Out of their league.

I think maybe that’s why Josh has been a little hesitant to introduce me into his life more. That I’m still a little too, well, you know. But I don’t like that word. I prefer words like prepared, meticulous, and fastidious.

But enough about me. Let’s talk about Josh. Josh, Josh, Josh, he’s something else. I think the thing that makes me feel a certain kind of way about him is that he’s one of the first guys I’ve ever met that doesn’t give me what I want. He’s not intimidated by me. For the first time in my life, a guy isn’t trying to prove himself to me, but rather I’m proving myself to him. And tonight, I’m going to do everything I can to impress him and all his friends.

Anyways. It's time for game night. I'm dressed to the nines. Let's do this.

Always happy to plant a seed which grows into a flower of a story!

Also I love the detail that the first sentence of this story is just Jennifer admitting "I make bad decisions". Sets the tone well.

A/N: Uh-oh, Jennifer is about to make another bet. But this time, the stakes are much higher. It's not just Josh that might see her this time. I really hope she wins this bet, or she's gonna have to see if she can handle four guys at once. Jennifer, we have got to talk about this gambling problem! Yes, you do have one. Listen, I'm the author, you do not want to argue with me.

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Part 2

I can actually feel the vibrations of the music even while standing outside Josh’s front door. He has good taste. Perhaps my outfit isn’t so out of place after all; it sounds like a party in there. Well, here’s a secret that Josh doesn’t know. He might be the king of Smash, but when it comes to dancing, I’m the queen.

I knock on the door with greater force, but when it opens, I’m startled. I see not Josh, but Miss Rachel. I haven’t seen her since... well... wow! She’s dressed to the actual nines. New Year’s is over. Why does she look so stunning? My eyes widen as I gaze at her hair, her makeup, her sparkling black dress.

Elegance.

“Um, hi, Miss Rachel. How have you, uh, been?” I say awkwardly.

I had almost forgotten Josh had a sister. I mean, she’s never around, and she never texted me again after that night. Seeing her now... I’m surprised and intimidated. There are only a handful of moments in my life where I haven’t been the hottest lady in the room, but next to her, I’m ordinary. She has a way of making me feel naked regardless of how much I’ve adorned myself in beautiful clothing.

“No time for pleasantries. Little brother and his friends are waiting,” she says.

Miss Rachel nods her head towards the living room. She doesn’t even invite me in. She didn't even acknowledge me. Click, click, click. Miss Rachel is a woman of few words; when she speaks, I listen.

I try to shake myself out of my trance. Okay. Tonight’s not about her. It’s about me. Well, it's about game night and meeting Josh’s friends. But it’s a little about me.

I take a deep breath and walk inside. Immediately, I see Josh and his friends playing Halo on his massive television screen. A wave of nostalgia comes over me as I remember the last time I played a video game with Josh. I blush. Never making that mistake again.

They’re all dressed pretty casual. Perhaps my outfit was a bit much. Well, whatever. It’s time to make an impression.

“Hey, boys! Ready to get the party started?” I shout over the loud music and sounds of explosions.

Boys and their toys. They love their little shooting games. It’s cute.

Josh turns his head towards me.

“Hey, Jennifer, one sec! Rounds almost over,” he says.

Josh turns back to the game and I stare in disbelief. Okay, not that I expected Josh to drop everything the moment I walked in, but his friends don’t even acknowledge me. They’re completely focused on this silly game. The TV is split into four screens and I think Josh is winning. Or, well, I don’t really know who's winning to be honest. I hope Josh is winning. Go Josh!

I don’t play shooty games. Maybe I would if I could play a character with cute, pink armor and a rainbow gun. Halo needs more color in this girl’s humble opinion.

I stand here for what feels like an eternity as the boys finish their ‘round’. My jaw is honestly hanging in disbelief that they can ignore me wearing this incredibly sexy outfit. Do they have any idea how hard it was to pull these tight pants over my ass? And they're not even looking at me? Are you kidding? No, they must not have realized. I’m sure once they take two seconds to turn around, they’ll know. They’ll know Jennifer is here.

The game finally ends with a lot of cheering and eruption. Whoop-dee-doo. Josh walks over to the stereo to turn down the music and finally acknowledges me.

“Hey, Jennifer. Glad you came. Although...” Josh pauses, noticing my outfit for the first time. He looks me up and down. “Interesting interpretation of casual.”

“Oh, um... Just wanted to make a good impression,” I say.

I blush and give him a mischievous smile. At least he’s not mad.

“So, hi guys! I’m here for game night,” I continue.

“Oh, right. Guys, this is my girlfriend, Jennifer. She can be a little eccentric, but she’s fun. Jennifer, these are some old buddies of mine from college. That’s Kyle, Tommy, and Jason,” Josh says as he points to each of his friends one-by-one.

Just like Josh, they’re all pretty nerdy looking. They wear jeans and t-shirts with silly video game references on them. I think Kyle's shirt has a Zelda on it. It's a cute little blonde boy wearing a big blue shield. It’s honestly a bit childish. Yeah, definitely sixes. No doubt they’d cream themselves for a chance with me. I can feel their eyes all drifting right to my smooth, flat tummy. I live for attention.

“Hey, Jennifer, nice to meet you. Are you cold? You know, it’s the, uh, pretty cold today. Would you like to borrow my jacket?” Tommy asks.

Oh my God! The nerve! I’m not wearing it because it’s comfortable, Tommy. I’m wearing it because it makes me look hot. Ugh. Boys. Why even bother dressing up or putting on makeup? They wouldn’t know the difference between Estee Lauder and Maybelline if a bottle of $65 foundation hit them right on their gigantic stupid heads.

“I’m good,” I reply politely.

I try to think of something witty to say, but by the time I do, they’ve already started playing another round! The nerve. Unbelievable. How are they ignoring me? Do they seriously not appreciate these sexy leather pants? Don’t even get me started on Josh. He’s not sleeping with me tonight without a serious apology. How in the world can they find Halo more interesting than talking to me?

“Hey, Jennifer,” Josh says, interrupting my angry monologue, “would you like to get in on the next round? Only room for four, but you can have my spot. I need a break, anyway.”

“Oh, err, um... Shooters aren’t really, like, my thing,” I say.

I feel a little blindsided by the offer. It’s sweet, but again, it’s not really my type of game.

“You sure? I can teach you. It’s super fun, I promise,” Kyle says.

“I’m good, but can I get you guys anything? Don’t answer that. I’ve got you, okay,” I say.

I give Kyle a wink and head to the kitchen. The moment I enter, I can hear the booming sounds of explosions and gunfire. They love their little game. So. Fucking. Nerdy. There’s no way these guys are not secretly fantasizing about what I’m wearing underneath these leather pants. No way. They just need some encouragement.

I open Josh’s refrigerator. It’s one of those fancy ones with a camera inside. Obviously, his parents have got some money. Weird how they’re never around, though. But it makes sense. I figure his family didn’t get wealthy by sitting around the house all day. They must be very busy people. Now let’s see, the beer, bottom shelf. The usual spot.

It’s easy to find things in the fridge, because it’s pretty much always empty. It’s something that’s always come off as a bit strange to me. They have such a gorgeous, luxurious kitchen, and yet his family clearly never uses it. Meanwhile, me, I would love to have enough space to not rearrange the appliances every time I wanted to make something. Jealousy is an ugly thing to wear, but I have to admit, I do wish I had nice things like this sometimes.

The noise and excitement of the Halo match blasts my ears as I come back with the refreshments. It’s time to make an impression. Boys, say hello to the cleavage. I know you want this.

“Hey guys! Anyone want a beer?” I ask.

I walk in front of the TV and bend down a bit, showing a hint of cleavage to the boys, while holding a beer in each hand. Surely, this must get Josh’s desperate friends into me, right? I’m sure that until now, they’ve probably just been pretending to be more interested in Halo, because they’re being respectful that I’m Josh’s girlfriend. But with a gesture like this, they’ll know that I’m okay with a little flirting. That’s all I want. I’m not afraid to admit that I like attention. I like being the star of the show.

“Hey! Josh, tell your crazy girlfriend to stop blockin’ the TV!” Jason shouts.

“I just wasted a frag,” Tommy yells.

“Jennifer!” Kyle clamors.

Josh stands up. It’s a dramatic gesture. Fuck, okay, this is his I’m getting mad look. I step out of the way of the TV and mutter something that sounds like sorry, and he sits back down and they continue playing. I take a seat in one of the cushioned chairs in the corner by myself. Balls. This sucks. Instead of making them hot for me, the only thing I’ve succeeded in doing is making my boyfriend upset. Where did I go wrong?

“You know, the offer still stands. My friends would love to play with you,” Josh says.

My ears perk up, but he rolls his eyes at me. Not like that.

“You don’t have to sit by yourself. Come on over and grab a controller?” he continues.

My boyfriend, Josh, he’s sweet. When I’m not driving him bonkers, I must admit, he’s so sensitive and considerate of my feelings. And I can’t really blame him for all the times that I do drive him crazy. I mean, he’s honestly too good to me. I know I’m a little high maintenance, and I think maybe that’s why I’m so enamored with him. No matter how crazy or difficult I get, he still wants me to feel like I’m part of the group. He doesn’t want me to be lonely.

Josh is literally the perfect boyfriend. I could kiss him. Okay, I take it back. I’m definitely fucking him tonight.

But I am not playing that stupid Halo game, and I am not leaving until his geeky friends admit they think I’m hot.

“No thanks, Josh. I’m good. But sure, I’ll join you guys on the couch,” I say confidently. “Beer?”

I squeeze in right between Tommy and Kyle, and they each take a beer from my hand. I’m grateful as the stinging cold sensation fades from my hands. I’ve been holding onto those for a while. I must admit I’m still slightly mortified from my poorly received gesture in front of the TV, but I figure I’ll give it one more shot. Hot girl sitting between them in skin tight clothing, that’s got to do something, right? I bet if I just glazed my hand over their jeans, I’d feel their boners.

Click, click, click. Josh pauses the game and the cheering stops.

“Nice to see you, Rachel!” Kyle says.

“You look great, Rachel,” Tommy says.

“Rachel, that dress is amazing,” Jason says.

“Nice to see you, boys. Apologies, no time to chat. Charity auction. Have fun, little brother,” Rachel says. She pauses, and then adds, “Not in my room. Try the pool table, if you must.”

Click, click, click. Rachel opens the door, but she looks back to me and gives me a wink before the door shuts with a bang. I flush. I still haven’t told Josh about what, er, happened that night. Frankly, I was kind of hoping it would never come up again. I’ve been extra careful to not go in her room or touch her things whenever I’m over here. Speaking of her room... not my room? Try the pool table? The hell does that mean?

The guys once again return to the silly Halo game. Master Chief this, Master Chief that. I’d like to introduce you boys to Master Bait, if you know what I mean. While they’re busy focusing on the explosions, I subtly shift my body towards Tommy and put my hand on his leg.

“Are you winning, Tommy?” I whisper seductively in his ear.

Tommy pushes my hand off of his jeans and doesn’t answer me. Okay, cold shoulder. Maybe Kyle or Jason will be more receptive. I can’t stand this. How am I wearing this sexy outfit and not a single one of them will give me the time of day? Is it just that they’re afraid of offending Josh? They should know he’s totally not the jealous type. Come on, guys, I just want some attention.

Once the next round ends, Josh puts down the controller and takes a stand.

“I’ve got to take my evenings meds and use the restroom. I’ll be a few. Think you guys can keep my girlfriend entertained for a minute?” Josh asks.

The guys all give him a positive response. They assure Josh they’re up to the task. And I assure Josh that I feel safe in their capable hands. Maybe this is the time for me to finally make my move. I bet they’re just too shy while Josh is here. I wait to speak until I hear the sound of Josh's footsteps walking up the stairs.

“Come on, you guys are giving me the cold shoulder the whole night. Listen, it’s okay to flirt with me,” I say confidently.

I know they want me. They just need some convincing. They’re too polite.

“Oh, err, you know, we just came over to play Halo. It’s a monthly thing. Been doing it for years. Plus, I’d never hit on you. You’re dating Josh. He's my bro," Tommy says.

I roll my eyes. I knew it. They just don’t want to disrespect Josh. But that's okay. Josh isn't here right now.

“Listen, Josh totally isn’t the jealous type. Believe me, I could tell you some stories about just how not jealous he is. It’s okay. You can be honest with me. Admit it, you all have been thinking about me naked since the moment I got here, haven’t you?” I ask.

“Not really,” Kyle says.

“Thought hasn’t crossed my mind. I’m more concerned about Josh camping me with that damn sniper,” Tommy says.

UNBELIEVABLE!

“Yeah, right. You guys probably almost creamed yourselves after I mentioned the word naked. Come on, don't play coy. I bet you have a boner right now,” I say.

"Err, nope," Jason says.

"Takes a little bit more than that to get me going, sorry," Tommy says in a patronizing way.

NO WAY! Bullshit. I'm calling their bluff.

"I bet I could make any one of you come in less than a minute using only my hands," I say.

Their ears perk up and there’s a short pause of palpable silence.

“And if you can’t?” Jason asks.

I wrack my brain for an idea. They actually want to bet something? I can’t turn down a good wager. Now let me see... what would make this night a lot more fun?

“First, let's talk about what happens when I do. We play a game that I want to play. Like Mario Kart. I love Mario Kart,” I say.

“And if we win?” Tommy asks.

"I'll play a game Halo?" I offer.

"If I'm gonna let you touch my dick, I want something more than that," Kyle says.

The other two boys nod their heads in agreement.

Fuck. They're still acting like they don't want me to touch their dicks. As if they're somehow immune to my charm. But I know boys. Josh, maybe, can resist my feminine wiles, but these nerds? They're toast. Just like any other guy, they will soon succumb to my sweet, delicate fingers. I can't lose. This bet is a for sure win. If they need something more on the table, I'm willing to do that.

Think, Jennifer, think. Hmm... what would three horny little nerds want from a hot girl like me? Oh, that's an idea. What was that Rachel said before she left about a pool table? I bet that would bring them to the table.

“How about this? I'll strip completely naked and you can tie me down to the pool table downstairs," I say.

"That's all?" Kyle asks.

"I dunno," Tommy says.

Are you fucking kidding me?

"How about this? You can touch me anywhere until it’s time to go home,” I say suggestively. "Is that good enough for the privilege of touching your little pecker, Tommy?"

“Deal,” Tommy says with zero hesitation.

Josh's nerdy friends don't even need a moment to consider my offer. All three of them offer their hands up to shake mine as the words leave my lips.

I accept and shake their hands. Finally, they admit it. They want to see me naked. That's all I wanted. And to win this silly bet, all I've got to do is make one of them come with a hand job, and then we can play Mario Kart. This is going to be a fun night. Way more fun than watching them play Halo.

“Jennifer, seriously? I’m gone for two seconds and you’ve already gotten yourself into trouble again? We have got to talk about this gambling problem of yours!” Josh shouts.

“I DO NOT HAVE A GAMBLING PROBLEM,” I reply angrily.

“What did you bet on this time? That you could beat them in Halo? I really hope not, because you can't,” Josh says.

“Well, no, not Halo...” I say.

oh, this is a hot start very nice.

Very nice setup. Waiting to see how things progress with Jennifer and the guys from here. I wonder what Josh's reaction will be when she tells him what the bet is.

Executionus wrote: ↑Fri Jan 06, 2023 2:45 am Also I love the detail that the first sentence of this story is just Jennifer admitting "I make bad decisions". Sets the tone well.

Yep, this was totally intentional. It had nothing to do with the fact that I was listening to the song "bad decisions" when I started writing this story. I'm a literary genius, setting up the tone with such a brilliant phrase.

We'll just call this one a happy accident.

MissAriel wrote: ↑Fri Jan 06, 2023 6:14 am I don’t play shooty games. Maybe I would if I could play a character with cute, pink armor and a rainbow gun.

MissAriel wrote: ↑Fri Jan 06, 2023 6:14 am I think Kyle's shirt has a Zelda on it. It's a cute little blonde boy wearing a big blue shield.

This girl plays Smash yet still had the audacity to think these words. I'm now convinced she deserves everything she's about to get and then some.

This girl plays Smash yet still had the audacity to think these words. I'm now convinced she deserves everything she's about to get and then some.

I love that you picked up on that little detail.

P.S. MissAriel is totally a DVA main.

A/N: Well, we've finally gotten past all the build up to the big moment. Here goes nothing, it's the craziest bet Jennifer has ever made! Can she reduce Josh's friends to minute-men, or will she end up stripped and tied to a pool table for the rest of the night? Read on and find out.

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Part 3

“Let me get this straight. Just tell me if I’ve got it right, okay? Because I think it’s going to sound a little crazy when I say it out loud. You begged me to meet my friends. I’ll be cool, you said. I promise, you said. And I said okay, fine, if you promise you won’t do anything too crazy, you can meet my friends. Wear something casual, I said. Okay, you said. But here we are. We had that whole conversation where you assured me that everything would be fine, and yet for some reason, you showed up wearing a crop top in the middle of winter, which looks ridiculous, by the way, and you've been acting anything but normal. Despite my best efforts to include you in the game and introduce you to the guys, you have instead relentlessly hit on them the entire night. And when I leave the room for two seconds to take my meds, you’ve asked them to tie you up naked? To the pool table!? Please, am I getting this right? Feel free to let me know if I missed anything,” Josh says.

“Well, when you put it like that, yeah, um, it sounds a little crazy.” I offer a gentle, awkward smile. “But the pool table thing, um, that’s only if I lose, which I’m not going to, obviously.”

I expect for a moment that Josh is about to let me have it. I mean, that crazy long monologue, the dramatic gesture... Josh is so hot when he gets mad. But he’s not mad. He’s laughing. Oh my God, he’s laughing. He’s laughing at me! He thinks this is funny. Okay, to be fair, better reaction than I was expecting. I mean, how many boyfriends would laugh instead of being mad at the idea of his friends seeing his girlfriend naked? Not many. Josh is one in a million.

“Jennifer, you are something else,” Josh says. He kisses me on my forehead. “Never a dull moment with you, is there? It’s okay, have fun, but be careful. I’m not going to bail you out this time.”

This time... fair. But that’s a story for another time.

I must say, I’m rather pleased. I was so worried Josh would be mad, but again, he’s the perfect boyfriend. He puts up with all my ridiculous quirks. What can I say? I’m a lucky girl. Well, anyways, he doesn’t have to worry. I don’t need a bail out. I’ve got this. I mean, really, how hard could it be? I mean, er, okay, not the best choice of words, but you know what I mean. They’re nerds, Josh. For a girl like me to even look at their you-know-what is a dream come true. And to touch it with my dainty and feminine hands for a whole minute? And with all this built-up sexual tension? I doubt I’ll even need that long.

“So, guys,” I say coolly, “Let’s be real, here. Only one of you is going to come tonight. Which one of you is it going to be?”

“Shouldn’t we lay out the rules first?” Josh asks.

I roll my eyes. Rules, rules, rules, whatever. This contest is going to be over in less than a minute. I’m ready to play Mario Kart. Come on. Rules are boring.

“Right. Okay, so, you’ve got one minute. Josh has a digital clock in his room. Can you go grab that, buddy?” Tommy asks.

Josh nods and heads to his room, leaving me alone with his three friends once again.

“I’ll go first. The clock starts the moment your hand touches my dick. And remember, you said you could do it with only your hand,” Tommy says.

“I haven’t forgotten what I said. Not that I’ll need an entire minute. I bet your tiny pecker is already throbbing,” I taunt.

Tommy shrugs. He’s unfazed by my bravado and taunts. Well, whatever, we’ll see if he’s singing a different tune in about 30 seconds. Oh Jennifer, please, stop, oh God. And when he comes, I’ll say, is this easy mode? Delightful. I love winning.

Josh returns with his alarm clock and places it on the shelf near what I’m going to call the ‘jerking off chair’. I’ll be able to see it clearly even from a kneeling position. This is probably all unnecessary, but Josh’s gesture is appreciated, since I’m going to be too busy working with my, uh, hands, to stand up and check the clock. And to be frank, I don’t entirely trust any of them to be honest about when the time runs out, so again, it’s nice to know it’s there. The clock blinks over and over: 00:00.

“Ready to come, little Tommy?” I ask.

“Josh, the rule is, hit the clock when her hand touches my dick, all right? And seriously, before we start, are you really okay with this, dude?” Tommy asks.

“Got it. And yeah, it’s cool. Honestly, I think she needs the lesson. Don’t worry about it,” Josh says cheerfully.

Great. Not even my own boyfriend is confident in my hand job skills. That’s minus two girlfriend points, buster.

Tommy is tall and attractive, but a different kind of attractiveness than my boyfriend. Whereas Josh has a more delicate face, Tommy’s jaw is more rugged and square-shaped, and he has a short, neat beard that he clearly makes some effort to maintain.

No matter, handsome or not, you’re about to blow your load, Tommy. I seductively walk up to him with my hips swaying the way a Victoria’s Secret model would on the runway. I give him my most sultry ‘come hither’ look and kneel before him. I stare directly at him with my sexiest please-fuck-me eyes. You wish, Tommy, but too bad, it’s never going to happen.

“Need a paper towel, cutie? Don’t want to get your jeans all wet,” I say.

Tommy rolls his eyes and doesn’t dignify me with a response. Even now as I’m on the cusp of touching his penis, he’s unperturbed by my jeers. I don’t understand how he can be so calm knowing that he’s about to be humiliatingly outed as a minute man in front of all his friends, but I shrug. Your funeral, dude.

I unbutton his jeans and pull his pants and boxers down slowly, ready to make fun of his tiny little dick. I know some guys get off on that, and I enjoy the power. It’s a win-win.

Fuck. Are you serious? My eyes bulge. I have no words. And it’s still fucking flaccid? Um, Josh, did you know your friend Tommy is hung like a fucking horse? Jesus.

“What the...” I say.

“You’ve got a lot of work to do in 60 seconds. Good luck,” Tommy says with a cheerful grin.

Are you kidding me? All that sexy swaying, a full view of my cleavage-bound tits, and nothing? Hell, he could probably even see some of my nipples from this angle. How the fuck is he not hard?

No matter. I grab his dick and I hear Josh push the clock. The timer starts. It’s soft and warm in my hand and I squeeze. I begin to talk dirty to him.

“I bet you’d love to tie me up naked to that pool table, wouldn’t you, Tommy? See my beautiful tits and curvy ass? Oh, I know you want it,” I say seductively.

But Tommy’s face is nearly expressionless. He almost looks bored. I glance at the clock. 00:15, 00:16, 00:17... Focus, Jennifer! The clock is running.

I squeeze his soft, warm cock with more force and begin to lightly pump up and down. I’ve done this so many times with other guys. It should be easy. But for some reason, this asshole and his monster flaccid dick will simply not get hard. It’s unbelievable.

00:38, 00:39, 00:40, 00:41... WHAT THE FUCK?

“Are you gay or something, dude?” I yell.

“Not gay. Sorry, like I said, it takes more than a mouthy chick with small titties to get me going,” Tommy says with a shrug.

I furiously rub and squeeze in desperation. I do everything I can trying to just give this guy a boner, let alone an orgasm, but I’m getting nothing. Nothing! It’s ridiculous. He’s got to be fucking gay. Fuck. I’m running out of time. Come on, dude, get a fucking boner! Please! I glance at the clock again. Please stop, please slow down. I need more time!

I pump Tommy's cock with more desperation as each second passes.

00:58, 00:59...

"Are you fucking kidding me!?" I shout.

00:60.

I just lost? This is crazy. There has to be something wrong with him.

“Well, Jennifer, looks like your time is up,” Tommy says with a shit-eating grin. “Good luck with Kyle and Jason, though. Hopefully you can at least give them a boner, although I'm not holding my breath.”

“Fuck you, Tommy! Fuck you and your stupid horse dick. Unbelievable. This is bullshit. You must be gay,” I shout.

“Hey now, relax, Jennifer. He’s not gay. You’re just being unrealistic. You can’t expect us to just get hard with nothing but your hand. We’re men of culture. We appreciate a good visual, you know?” Jason says.

THE NERVE!

“Are you suggesting that I take off my clothes? Not happening, pal!” I spit.

“No one’s saying that, Jennifer, just that if you don’t want to be naked on the pool table, it might be wise to take something off here instead,” Kyle says.

Fuck!

I’m flush with anger. I want to scream at him, no, never happening, you’re never seeing any of this... but when I stop to really think about it, I know Kyle is right. I couldn’t even get Tommy hard. If I don’t want to lose this humiliating bet, I’m going to have to be prepared to make some concessions. I look to Josh, but he only shrugs at me, and I can read his lips: ‘you made your bed.’ He’s right. I made this bet. Now I have to do what it takes to win it.

“All right, fine. Whatever. Who’s next?” I ask.

“I’ll go,” Jason says.

“Just so you know, I’m not playing around this time. You’re fucked,” I say.

I cross my arms and grab the ends of my crop top and slide it over my head, unveiling my black Victoria’s Secret push-up bra for his eyes to feast upon. I’m not going to strip all the way, of course, but to my underwear? No guy could resist. And I’m just getting started.

I walk up to him and turn around, my ass just inches from what is no doubt the starters of a massive boner. I bend over and demurely start to strip down my skin-tight leather pants, revealing my bubble-licious ass cheeks and matching skimpy black thong. This was intended to be for Josh tonight after they went home, but well, if these guys are harder to please, it’s a sacrifice I’m willing to make. I briefly slide off my shoes so I can step out of my pants entirely, and then quickly put my leather boots back on. Always keep the shoes on. I look way sexier in my underwear like this.

I turn around to face Jason and bend down, giving him an even fuller view of my tits than Tommy had. Without a doubt, from this angle, I know he can see the edges of my pink nipples. I bet he’s so hard.

“Let’s see what’s in these jeans, shall we, Jason? Got a little present for me?” I tease.

“Nothing little about it,” Jason says confidently.

As I pull down his jeans, my eyes bulge again. Josh, do you have any friends that are regular-sized? What the fuck? At least Jason is rock hard, but fuck, this thing is huge. I’m not even sure I can wrap my whole hand around it. I might need both hands. God. I think I’m more embarrassed by the sight of this guy’s dick than I am about being in my underwear.

I shake my head. You can freak out about his dick later. Focus, Jennifer. It’s time to give this guy the hand job of his life.

I grab Jason’s dick, my hand looking even smaller than usual, and my fingers just barely wrap around the entire thing. I take my other hand to cup and fondle his balls, a trick that I know drives some guys wild. I’ve got to pull out all the stops, because the last thing I want to do is give Kyle a hand job, too. I begin stroking and pumping his dick up and down, and I think I’m making progress. I can hear Jason making tiny moans.

“I bet you like that, don’t you, Jason? It’s okay, you can open your eyes, look at my sexy titties. I bet you wish you could touch them, don’t you? Or to give my cute little bubble butt a good smack? Never gonna happen, sweetie, but what I can give you is an earth-shattering orgasm. That’s right, be a good boy and come for me.”

I continue to stroke up and down. I just know he’s almost there. His moaning intensifies.

“Come on, Jason, just let it all –”

“Time!” Jason says.

Oh my God. I was so completely focused on jerking him off that I’d completely forgotten about the clock. I stare at it in horror. It continues to tick upwards: 1:06, 1:07, 1:08. Unbelievable. I was so close. I just needed a little bit more time. Fucking damn it.

“Good try, though, Jennifer,” Jason says with a smile. “Really, if you had five more minutes, I bet you might have even gotten there.”

Five minutes? Fuck you, Jason.

“Jennifer, you know, from my perspective, it kind of looks like you’re in trouble. I mean, one more failure, and you’re going to lose, well, everything. But I’ll tell you what, if you just forfeit now, you can watch us play Halo instead of being tied down to the pool table,” Kyle says.

Tommy and Jason both nod in agreement, but I’m furious. Who the fuck does he think he is?

“Fuck you, Kyle, and your stupid Zelda shirt. I’m gonna make you cream yourself. I went easy on Tommy and Jason, but for you, I’m pulling out all the stops,” I say.

“All right, Jennifer,” Kyle says with a sigh. “Don’t say I never tried to help you.”

I don’t need your patronizing pity, Kyle. Fuck off.

Yet, I have to admit, I do consider his offer. Maybe I should. It might be better than losing this bet. Fuck. I never thought it would go this far. I’ve struck out two for two now. If I want to win this bet, I either need to forfeit or go further than I ever dreamed. And in front of FOUR fucking guys. I mean, sure, I’ve been naked before, but in front of like, ONE person. Not my boyfriend and all of his fucking nerdy gamer buddies. Can I really do this?

I have to. I wish I could avoid it, but I don’t have a choice. I just can’t risk it. If I stay in my underwear and fail again, I’m going to have to let these losers touch me anywhere. And I bet Kyle is a fucking virgin with that geeky Zelda t-shirt. Wouldn’t that just make his fucking day. Hell, they’re probably all virgins. No, I’ve got to pull out all the stops. I’ll take everything off. I’ll let them gaze on my tits and ass, I’ll bend over and give him a full view of my pussy lips. I’m going to give him a stark-naked hand job and he’s going to blow his load like he’s never blown it before. There is no way, no universe, in which Kyle can hold out against what I’m about to do.

I feel like a slut, but it’s not like that. I seriously don’t have much of a choice. It’s either strip now for a minute, or spend the rest of the night being their naked sex toy. It’s not a hard choice when I lay out the options like that.

Whatever. I can't get cold feet now. I've got this. I'm a bombshell bitch and I'm gonna turn Kyle into mush. Get ready to come like the little man slut you are.

“Ready to scream my name like a little girl, Kyle?” I ask.

Okay, actually, I’m the one that’s about to be screaming like a little girl if I can’t get Kyle off. I put on a tough show, but I’m terrified that I’m about to lose what I thought was an easy win. I can’t believe I’m about to take off my bra and thong and I haven’t even lost yet! This is so unfair. And of course, Josh is no help in this dire emergency as my dignity hangs in the balance. ‘I’m not bailing you out this time.’ What. Ever.

“So, Jennifer, ready to show me the goods?” Kyle says with a smirk.

“Not happening,” I lie.

I’m not even sure why I just said that. I’m just stalling. I have to do this. Come on, Jennifer. It’s not that bad. You’re already down to your bra and thong. It’s not like it’s that much worse.

EXCEPT IT IS THAT MUCH WORSE. Four. Count them, four. I have never been naked in front of four people before. Josh, come on! Tell them I can’t, I’m your girlfriend! Okay, I know I don’t want him to do that. I’m not going to welsh. When I make a bet, I always hold my word, no matter how dire the circumstances. But also... mercy? I don’t want to take my clothes off in front of Josh’s nerdy friends!

“If you don’t want to jerk Kyle off, we can head down to the pool table now,” Tommy suggests helpfully.

“No, no, it’s fine. I just needed a moment. Uh, okay, let’s go, Kyle. Ready for the night of your life?” I ask.

“Like you did for Tommy and Jason?” Kyle replies.

Ugh. Sometimes, I really hate boys. But it’s time. Sometimes, it’s better to go ahead and just rip the band-aid off. .

I reach back and unclasp the hooks of my black push-up bra. Thank you, Victoria Secret, you served me well. Thank you for all the cleavage and free drinks at the bar. I’ll miss you. Sigh. I’ve been in this situation enough times to know what happens when I take off my underwear off. I’m probably never seeing it again. Josh, seriously, you need to take me underwear shopping. This is like the third or fourth bra that I know I'm never getting back.

One strap down, then the other. But this is the hardest part. I can't move. They’re all staring at me. Stop staring. If you were gentlemen, you’d turn around!

“Let’s see those titties,” Kyle cheers.

“Hell yeah,” Tommy agrees.

“Can’t wait to see the nipples without that bra in the way,” Jason says.

“Look on the bright side, at least you’re the center of attention now,” Josh beams.

I hate you all.

I let the soft material that once covered my chest fall to the ground and the illusion of my busty cleavage goes with it. As much as I want to immediately fold my hands over my chest, I can’t. The whole point is I need to get Kyle hot and bothered. I have to let these losers just stare at my tits and there’s nothing I can do about it. It’s almost worse than being tied up, because at least then, I could blame the rope. But this is worse than the rope. I can’t cover because I’ve given them all power over me, because somehow, I’m not hot enough or good enough at hand jobs to get them off, and I’ve been reduced to stripping completely in a desperation move to not be their little slut toy for the rest of the night. This is, without a doubt, the most humiliating night of my entire life. It’s even worse than that time the cop pulled me over. Count them! One, two, three, FOUR! Four guys! How could I let this happen?

“Wow, she’s enjoying it, too. Look, her nipples are hardening in real time,” Tommy says.

“Whoa... Josh, your girlfriend has a great rack. Small titties, but damn, they look so firm and they’ve got that nice shape, you know?” Kyle says.

I start to yell some expletives to Kyle, because hello, I’m right here, jerk face. But, again, the whole point of this is to make him happy, so I clench my jaw shut and say nothing. Okay, look, it’s fine. I just have to pretend to enjoy this. Remember, I’m hot stuff, and I’m about to make Kyle my bitch. If I do this right, in sixty seconds, I’ll be dressed and playing Mario Kart, and in a few weeks, I’ll laugh about that time I had to strip for my boyfriend’s gamer buddies. No big deal.

But if I’m about to make Kyle my bitch, why am I the one with my legs shaking?

“Panties coming off, too? Will the carpets match the drapes? Are you a natural blonde?” Kyle asks.

“You’ll just have to use your imagination because you’re never going to find out,” I say.

I wax for a reason.

“She’s a brunette,” Josh says helpfully.

“JOSH!” I yell.

I slide my panties down my legs, revealing my smooth, beautiful pussy. Once my panties fall down to my knees, I gently let them fall to the ground and step out of them one boot at a time. God, this is so humiliating. Why me? Sigh.

I turn around and stand still for a moment to give Kyle a spectacular view of my ass. Yeah, take a good look, this is the last fucking time you’re ever seeing this, I swear to God.

I bend down to pick up my panties. I can feel the blood rushing to my face. Kyle can see literally everything right now. This is awful. I’ve never felt so acutely aware of the feeling of the cool, winter air touching my asshole. This is a nightmare. Kyle has a clear, unimpeded view of my pussy lips and asshole, and instead of covering myself, I’m encouraging him to look, because I’m that desperate to get him horny.

And what’s even worse is that I’m probably closer to getting off than he is right now. Err, I mean... no, this isn’t making me horny, damn it. I’m not some kind of exhibitionist slut. I’m not!

As if Kyle can’t see how wet you are while you’re giving him the VIP tour.

SHUT UP ALTER EGO.

Oh God, I bet he’s taking a mental photo to remember this moment forever. This isn’t happening, this isn’t happening, this isn’t happening.

“Wow, Jennifer, I’ve never met a girl that showed me her asshole and pussy within half an hour of meeting her. I guess you love showing off, huh? But you know, I can see why you’re so confident now. Your lips are so tight, they look like they belong to a porn star. Are you a porn star, by any chance?” Kyle asks.

“What do you think?” I say sarcastically.

“No, but you should try it, considering how much you love showing your privates to strangers,” Kyle teases.

“Hey, Jennifer, can you turn towards me and Jason? We want to see your asshole, too,” Tommy says.

“I bet you could’ve gotten me in two minutes if I’d seen that,” Jason says.

I roll my eyes and ignore them. I pick up my matching black bra and thong. Oh God, seriously, my panties are soaked? I’m just going to put these over here. Nothing to see here, guys. I don’t think they noticed. No, I’m not horny. I’m angry, mad, infuriated, but I am not fucking horny.

“Damn, Josh, your girlfriend is smokin’ when she’s all exposed and embarrassed like this,” Tommy says.

“I’m not embarrassed!” I argue.

I’m a pathological liar. Sue me.

“Jennifer, you’re super cute when you blush. This shy thing you’ve got going on, it’s giving me a boner. Keep doing that,” Kyle says.

“I love your little titties, Jennifer! I can’t wait to give them a good squeeze,” Jason says.

“Nobody’s touching anything!” I shout.

Okay, no more stalling. I’m ready. I’m going to make you squeal, Kyle.

I clear my mind and sway my hips, giving Kyle my sultry tried-and-true runway walk. I’m gonna rock your world, little boy.

Please be hard, please be hard, please be hard.

I sit on my knees and spread out my thighs in front of the jerk-off chair and begin to rub my tits against Kyle’s jeans. I seductively raise my chest and find myself at eye level with his manhood. I unzip Kyle’s jeans and slide them down to his ankles. I can see his boner through his boxers. Nice. Already nice and hard for me. Good boy.

I know I’m going to win. He’s already halfway there.

“Kyle, I promise I won’t judge you when you squeal like a girl, just let it all out, okay, little guy?” I tease.

“You’re the one begging to touch my dick, Jennifer,” Kyle says.

He’s smiling at me. A stupid, ridiculous patronizing smile. The fucking audacity.

I hate boys!

“Let’s see how much you’re smiling when I do this,” I say.

I swipe his boxers down and unveil his cock. Wow. I’m actually pleasantly surprised. It’s normal sized. Thank God. If I had to wrap my hand around one more oversized horse cock, I was going to flip my shit. Kyle has a perfect dick. Not that I would tell Kyle that, but I’m just saying, I would never let those other two guys anywhere near my pussy. There’s not enough lubricant on Amazon to make that a pleasant experience.

I just stare at it. He has such a pretty penis. I actually do want to touch it. Okay, okay, calm down, Jennifer. Let’s get to business. Remember, he’s the one that’s supposed to be desperate for you. It’s just a penis, an ordinary, middle-of-the-road penis attached to a nerd named Kyle. I bet he dreams every night of having a chance with a hot girl like me. Well, here’s your dream come true, I’m jerking you off, loser.

Kyle is still giving me that patronizing smile! What the hell, dude? He’s not even the tiniest bit embarrassed. No, he’s confident. Jesus, how is this guy and his mediocre dick more confident than I am? Nothing about this night makes any sense. Most of the guys I’ve met, I could make them come while they were looking at fucking linoleum. Yet tonight, I was forced to strip naked in desperation, and I had to practically beg Kyle to get hard. It wasn’t supposed to happen like this!

“You can put it in your mouth later if you ask me nicely,” Kyle offers.

“Less talking, more moaning,” I say.

I grab Kyle’s hard dick with my petite hand and Josh starts the clock for what I pray is the last time.

I rub my breasts against Kyle’s leg and start giving his dick slow, rhythmic strokes up and down. I start off a little slower, but gradually increase the speed. I can see the pleasure on his face. He likes this. His eyes are closed. It’s working. He’s going to explode long before the timer runs out. I continue to rub my tits against his body while jerking his mediocre dick with my hand. I rise up higher on my knees and shove my tits in his face while continuing to hold his manhood with a firm hand. He opens his eyes and sees the glory of my beautiful pink nipples and shapely breasts.

“You like that, Kyle?” I ask.

“Nice tits, Jennifer,” Kyle says.

“Yeah, that’s right, be a good boy and come for me,” I say.

I relax and lower my knees, letting my tits hang as I continue to stroke him. I’m almost there. Should be done in plenty of time.

“PAUSE! STOP, JENNIFER!” Tommy shouts.

Josh pauses the clock. I look around confusedly, but continue holding Kyle’s cock. What the hell? He’s about to come. This is bullshit! I’ve still got 15 seconds left!

“What the hell is this? You’re cheating. You can’t tell me to stop just because he’s about to come,” I shout.

“The rules are hands only. Your tits were touching his dick. That means you’re disqualified,” Tommy says.

“You know, as mean as it feels to say, he’s right. You did say hands only, remember, Jennifer?” Jason says.

“Yeah, there’s no way I could have missed your cute pink nipples brushing up against my cock. You broke the rules, Jennifer,” Kyle says.

“I object! Josh, tell them they’re being ridiculous,” I shout.

Josh just gives me a helpless shrug and says, “But Jen, you did say you could do it using only your hands. I'd be the first one to back you up if it wasn't true.”

“I think we’re all agreed. Ready for the pool table, cutie?” Tommy says.

“Ever since she took off her panties, I’ve been wanting to give that ass a nice squeeze,” Jason says.

“I just wanna flick her nipples with my tongue,” Kyle says.

“This is bullshit! I didn’t even get to finish the round. Come on, you know this is ridiculous. It was an accident!” I protest.

I have to convince them to give me another shot. I cannot just go down like this. It's not right. I can't just lose the bet without even getting my 60 seconds in. I know I can make him come. I just need another chance.

“Well, I guess we could consider it...” Tommy says.

“I’d be okay with giving you another chance if you do a penalty.” Jason says.

“That sounds reasonable, doesn’t it Jennifer? They’re gonna give you another shot,” Josh says.

Thanks, Josh. You’re SO helpful.

“But since it was Kyle that she violated, he should make the decision,” Tommy says.

Violated!? That was probably the best moment of his entire damn life.

“Hmm, I like the sound of that,” Kyle says optimistically.

“Um, Kyle, please? Give me another shot. You know that’s a pretty messed up way for the bet to end. Please be reasonable,” I plead.

Kyle walks around me, ogling my body. I start to feel self-conscious and start to cover my chest.

“Hands to your side. I’m thinking,” Kyle says.

I can’t believe this guy. But I do as he says. I lower my arms and close my eyes. If I can’t see him, maybe it won’t be so humiliating. Fuck. Even with my eyes closed, I can literally feel their eyes staring at my small tits. I wish I never came to this stupid party.

This whole night is ridiculous. I have to humiliate myself and take all my clothes off because all three of these nerds have some crazy erectile dysfunction, as if I was supposed to know they have some crazy rare medical disease before I made that bet. And then when I almost win anyways, and Kyle was like five fucking seconds away from blowing his load, they make me stop! It feels like the whole damn game is rigged.

And now to top it all off, I have to pay a penalty? Just because his stupid dick grazed my nipple? Oh, and of course, Josh is just loving this and going along with anything they say. Come on, Josh, you’re supposed to be on my side. Even if I did accidentally touch it with my boobs, so what? I deserve another chance. How was I supposed to know that would happen?

Kyle walks up to me and comes face to face with me. He’s just standing here looking into my eyes. What’s his deal? I feel uncomfortable and look downward.

“Tell you what, Jennifer, if you fulfill a penalty, then you can try again,” Kyle says.

Great. I’m sure the penalty will be a total cakewalk.

“Thanks, but what’s the penalty?” I ask.

“First, I need you to take off your shoes,” Kyle says.

NO, NO, NO, NO, NO, NO, NO, NO!

“Is that really necessary?” I ask.

“I think the next part will be easier without heels,” Kyle says.

“Please, Kyle, I like my shoes. I promise, whatever the penalty is, I’m fine doing it in my shoes,” I say.

“Let’s just take her down to the pool table, dude. That ass is begging to be spanked,” Tommy says.

“Fine!” I yell.

I bend over, my pussy and asshole on display for Tommy to look at as much as he wants, and I take off my shoes. I hand them over to Kyle, who now looks so much taller. I have to look up to meet his gaze and I feel more humiliated now in this moment than I did when I had to take off my underwear. I feel so powerless. Why do they always want to take my damn shoes?

“Wow, she’s so much shorter without those boots, isn’t she guys?” Kyle asks.

“Yeah, she is,” Jason says.

“Definitely, she’s really short, isn’t she?” Tommy says.

I grit my teeth and endure their teasing silently. Laugh all you want, guys. When I win this bet, I’m going to make you pay, Kyle.

“Okay, so the second part is I want you to dance for us on the table here. For music, I’m thinking Porn Star Dancing. That work for you, Jennifer?” Kyle asks.

He is seriously asking me to dance to that stupid song on the table like I’m some kind of stripper?

“Really?” I ask.

“And don’t half ass it. I know you can dance. Everyone does. We’ve all seen it on the Internet,” Kyle says.

“The Internet?” I ask.

“Yeah, remember the 90s bar? Back in college? This Youtube video has got like a million views. You’re crazy popular,” Kyle says and he pushes his phone into my face.

Wow. He’s right. There I am, dancing my heart out in the middle of the bar. This is wild. I didn’t know I had a following on Youtube. That’s kind of cool.

But hey, no fair! Shouldn’t I be getting paid royalties or something? This channel has a million views because of me! And I haven’t seen a single penny.

“So, yeah, dance like that, please,” Kyle says.

“How did you even find that?” I ask.

“Just lucky, I guess,” Kyle says.

“Can’t you pick some other song?” I ask.

“Kyle, can we PLEASE just tie her to the pool table,” Tommy asks.

“There will be no tying me to the pool table!” I yell.

I start to climb up on top of the coffee table.

I hate boys!