Tag: bet

It was such a hot plan. you’d been gunning for your friend’s wife for so long. When he suggested a wife swap for a night, you jumped on it immediately. Sadly his wife didn’t do the same when you got back to her bedroom. She looked skeptical. By the time she got it fully erect, she started laughing. It really hurt when she pulled out her phone. Was she going to take shame pictures? This was a nightmare. Wait, no, it was a nightmare when you realized she had facetimed your wife, who was in the middle of sucking off your best friend, in your marital bed. She picked up without letting his, apparently huge, cock out of her mouth. 

“Bitch! I got screwed on this deal! And not in a good way.”

Your wife took a break, jerking him in one hand. “Sorry, baby, but you see what I have to deal with there. I couldn’t let this offer pass me by after the stories you told. But, like, why don’t you just come over? I doubt your husband would mind a second, would you?”

Off to the side: “Hell no!”

“Mmm, that’s more like it. But what do we do with small wonder over here?”

“Leave him. But keep the connection open. I want him to watch.”

“Naughty! Okay, cuck, don’t cum on my phone. If you do, you never get to watch again. Got it?”

cuckolding-and-female-allure:

As soon as he came in her mouth, your wife told you, “honey, don’t say that watching him didn’t make you feel dwarfed. You just have to admit it … and offer him our marital bed.”

Why had I ever made such a bet? It was just the heat of the moment. I’d gotten in some silly argument with this stranger at a party. My wife was annoyed but I wouldn’t back down. Eventually it devolved into literally comparing dicks. His was, very big. I told him I didn’t care how big his cock was, no man could make me feel small. Love and sex are about more than size, I told him. My wife had laughed. I glared at her. 

“Oh, come on. It’s not everything but you have to admit it helps.” 

My pride was besieged from all sides! I refused to concede the point. He said he’d prove it to me. I said nothing could move me and so agreed to any terms he might have. Stupid. He said he’d prove to me that a big cock could make me feel like the smaller man in regards to sex. If he could do that, he said, I’d have to allow him to try to best me at love, too. Deal!

It was then he turned to my wife and asked her to be his assistant with his demonstrations. She was taken aback at first, but soon she got an evil smirk on her face and looked at me. “Any chance to prove this smug bastard wrong.”

I was too proud to back out as I realized what he intended. He guided my wife to a secluded side room away from others at the party. I followed awkwardly, hearing the whispers of my friends and colleagues wondering why this other man was leading my wife by the hand.

“Okay, so your wife is going to service me. If you can watch the whole things and still honestly say you feel like a superior or even equal man, then you win. I will do whatever you wish.”

“Just leave us alone.”

“Deal. But if you do feel a bit…diminished, you have to let me prove that I’m the bigger man in love, too. Cede your marital bed to me for…a month. After that month, we’ll see who she loves more.” Deal.

He instructed her to take off his clothes. My wife complied with gusto. He laid down and ordered her to start playing with his massive cock. She gasped as she got her hands around it. She continued making approving sounds as she worked it to full erection. “Oh my god, babe! I can barely fit my fingers around it! And it’s so long! You must feel so small already. Your cock is nothing like this. It’s a whole different breed!”

I felt sick. “Just finish it.”

“Mmmm, but not with your hands, with your mouth.”

My wife bit her lip. She was pretty good at blowjobs. Even so as she worked it in her mouth she could only fit it halfway in. Fuck.

As soon as he came in her mouth, my wife told me, “honey, don’t say that watching him didn’t make you feel dwarfed. You just have to admit it … and offer him our marital bed.”

When you started dating your girlfriend she had warned there would be “complications”. You were obsessed and madly in I love so you agreed to do “whatever it takes” to be with her. 

That’s when she sheepishly brought out The Contact. It said someone named Lucas Tipton owned your girlfriend’s body and was entitled to “ravage her whenever he so pleases.” What the hell?! He was her ex, she explained. She’d been into his kinks and so signing away her bodily autonomy had just seemed really hot at the time. Nothing in the contract had forbidden her from dumping the asshole when she grew wise to his womanizing. Unfortunately, according to the rules, only he could release her from her obligations. 

Surely this wasn’t legal? “No,” she replied, looking away, “but my Papa brought me up to respect men and always honor my agreements and promises. I hate it, I do, but I just can’t dishonor myself and my Papa by turning back on my word. He may not keep his promises, but I do. I can’t sink to his level. I know this is weird, but…can you still love me?” Of course you could. You had no choice but to love her. 

That’s how you ended up with a girlfriend who fucks her ex more than she does you. Oh, at first she tried to keep parity, but more and more these days she’s just too tired and sore. You hate it, but you love each other. And you respect her sense of duty and trust. Sure, sometimes you wish it was a little less… Like when she earnestly thanks every cat-caller for their compliments and complies with their demands that she “twirl for me, show me what you got.” Or how she abandons you at the drop of a hat when her ex texts her a booty call. Or worse, the appointment she has to get a clit piercing and tramp stamp tattoo reading ‘Luke’s Bitch’. But what can you do? “I’m so sorry babe, but he owns my body; I take that seriously. And it’s not like I’m not his bitch. But I’m your love, honey.”

curiositycure:

jerkoffpics:

JerkOff / Handjobs @ Jerkoffpics

The bet was a hand job. I didn’t know she was going to jerk him off all over her tits like that.

At first I was just glad I hadn’t lost to Greg. When I realized my girlfriend had to jerk off my work rival, I was perturbed but still relieved. I hated the guy and was disgusted by him. My girlfriend at least thought I was overreacting. This would be over soon. 

Then Greg insisted that a “real” hand job was either “on the bitch” or “in her mouth.” I called foul but my girlfiend just agreed. What the hell?! She said that was true. It wasn’t a proper HJ unless the giver tasted the cum or was marked. To do otherwise showed disdain, she said. I distinctly remembered her jerking me into some Kleenex but I was too confused and embarrassed to say so. Then she started removing her pants and top. Ummm? 

“He looks like he packs a punch, babe. Don’t want to walk home all stained. Remove your clothes too, okay, Greg? I don’t want to feel like the odd girl out.” He complied, sneering at me. “Very nice. Okay, now just focus on my tits and face. That’s right, ogle me. Now mark this bitch. You won; you’re the man.” She kept up this patter as she jerked him. “You beat your rival. Claim his woman. Good. Demean him. Show my boyfriend who’s boss.” When he finally came all over her, she giggled and leaned in. She kissed his cock and licked it clean. “Mm, you even taste like a winner.” She scooped up his cum off her chest and swallowed it. “I can’t get enough. Babe, get over here and taste your better’s leavings. Now! Good. Show your submission. Yes, taste it, love it.”

Winter googled around and decided to start with Chaturbate and MyFreeCams. She had no idea what she was doing but she just had to get their attention. Ever since your girlfriend had gone out drinking with you and your coworkers that one time it had been her holy mission. Winter had watched as Chuck and Ozzy strode over, called you a sissy for drinking a margarita, and commented on your girlfriend’s ‘hot tits’ without you doing anything. She’d been so humiliated and angry. Then Ozzy picked up the margarita and poured it directly into your lap. You yelped and ran for the bathroom. They laughed and mocked your bravery and manliness. Winter’s face burned, beet red, she was sure. “If you need a real man, I have an 8 inch friend I’d like to introduce you to, hot tits,” growled Ozzy, leaning down close to Winter. She suddenly realized her panties were soaked. She tried to speak but only a strangled sound came out and she glared into her lap in humiliation. The bullies guffawed harder, walking back to their table in triumph. She was just a joke to them, Winter realized in disappointment (and then shame at her disappointment). 

You returned to the table with a big, slightly reddish, spot on your pants. “Sorry about those assholes. They’re the ones who have nothing better to do at work than pick on me. So immature.”

“You…you didn’t even try to stop them,” she blurted out with meek fury.

“Ah, well, there’s no point, really,” you replied sheepishly, scratching the back of your head. “Besides, you saw them, they’d totally kick my ass if I tried to fight them.”

“They…they called me ‘hot tits.’ Right in front of you.”

“Heh, well they’re not wrong…I’m sorry. That’s just what they’re like. They’re gross dudes. Nothing I say will change them now.”

“Well someone has to try,” Winter said, standing up and walking over to their side of the bar.

“Stop, you’ll just make it worse if you chastise them,” you called after her.

Was that what she was doing? Going to yell at them? That’s probably what she would have said but Winter knew on some level she just wanted their attention again. 

She found them in a group of male work buddies, telling jokes and carrying on. They were playing pool, making silly bets. Ozzy and Chuck were clearly the center of the social group. Winter tried to break into the conversation, to get their attention. But she was shy, unsure what to do, and was totally ignored. It was like, to them, she wasn’t even there. This only stoked the flames of Winter’s shame and desire. 

She went to the bar to get a new drink and walked back over. As she stood on the edges awkwardly sipping her martini, Winter caught that they were now talking about a ‘cam girl’ website. She barely knew what that was. Like group Skype with stripping? Chuck was goading Ozzie for being too into it, saying that the girls were hot, but it was pointless. Oz doubled down, boasting that he was halfway to getting his dream cam girl to visit him and cheat on her boyfriend. Winter bit her lip at that thought. Chuck called bullshit. After some banter, Chuck had bet that he could bang a cam girl in real life before Ozzie ever could. They shook on it.

So now Winter was setting up two cam accounts. She’d spent a few hours reading up and watching some streams. She’d even made friends with a gothic lolita cam girl and gotten some tips. She needed a better webcam, but her mission was only to get Ozzie and Chuck’s attention, not to become a professional. To feed into the bet, she publicly listed where she lived and even signed up as the username ‘Detroit Cheater Slut’.

While you worked 12 hour shifts at the factory, your girlfriend put in long hours perfecting her new craft. She ran an Etsy store and was used to making YouTube craft tutorials, but this was still terrifying. She didn’t show her face. She didn’t even speak at first. Her username attracted cuckold fetishists. They role-played with her in chat, either as cucks or bulls. This made Winter so fucking wet. After the first few times she had orgasms on camera, involuntarily screaming about betraying you, Winter loosened up about not speaking. Soon she had a loyal little following. Alphas and betas alike bought her equipment off her Amazon wish list and some even sent her paypal tips to buy faster internet access.  

You asked Winter what she was doing with all the gear. She said she had a Twitch stream. You had to badger her a few days, but eventually she let you see the channel (it took her that long to scramble to set up ‘Summer Gamegrrl’ and tell her fans to stop by to make it look real). You were surprised at how rude and obscene her viewers were. She was just a girl playing Stardew Valley, but they were were really into sexually harassing her, asking ‘Summer’ to flash her boobs. And begging her to cheat on her in game boyfriend. If you wandered into the room while she was streaming, chat would fill with ‘CUCK BOY ALERT!’ and “Cage that Sissy’.

“Why are they like that? How can you stand it?” you asked her one night.

“Oh that’s just what boys on the internet are like.  Don’t take it to heart, my darling cuck boy, haha!”

“But…you don’t even try to defend yourself…or me.”

“They’re gross boys, honey. Nothing I can say will change them now. You showed me that with Chuck and Oz.”

“It’s just…do you have to show your tits off like that? I mean you have a webcam view but you don’t show your face, just your chest, and you wear such low cut tops…”

“Honey, it’s called click bait. Are you saying you’d prefer I show my pretty face to all those nasty boys?”

“No, but this seems worse. I mean…it might be better if you did.”

Later you’d tell her you meant she should show only her face and not put on a cleavage show. Instead she’d done both. Winter just shrugged and said there was no going back now, after they’d ‘already signed up for the girls’.

A couple months later Winter was on LiveJasmine too and she had a paid SnapChat feed. She even started a Tumblr. She was a very busy girl, especially after she’d done a big event to finally reveal her face to the world. She’d hoped if Chuck and Ozzie were out there the’d recognize her and reach out. No such luck. In an act of desperation, she signed up for MyFetishLIVE and added gags and piss play to her repertoire. Maybe they were real dirty boys? Still no luck. 

She was scared of being found out, but getting eager. Winter started telling a few of her supposedly local devotees on private chat about her mission. The cucks found it hot and vowed to help. The bulls were impressed that she was the real deal but wanted to know what they’d get out of it. She promised to fuck the one who found Ozzie or Chuck for her. After she’d fucked them and fulfilled her dream. Winter had realized a few weeks ago that she wouldn’t be able to stop with just those two bullies anyway. This was all way too hot. But she wanted to have them first. She owed that to herself, and to them.

In the end, one bull found Ozzie and one cuck found Chuck. Each was directed to Winter’s cam show on a different network. Oz was especially into her schtick and started trying to get her to meet IRL. He totally didn’t recognize her. Chuck totally did recognize her. Winter imagined he felt like he’d won the lottery. He began negging her and her boyfriend. He wanted to show her what a ‘real man’ was soon.

Winter determined the bet was ongoing. She wanted her wet dream duo together, so she arranged to meet up with them both in the same place at the same time. They were confused to see each other and were having a heated discussion as Winter walked up. “Oh don’t fight over me, boys. I can’t bear to think of my two biggest fans at each other’s throats. You see, I need you both to cuckold my sweet sissy boyfriend, together. Can you do that, for me?”

They weren’t excited about an MMF threesome, but Winter explained how she knew Chuck desperately wanted to deep-throat her and Ozzie was obsessed with taking her virgin ass. They could spit-roast her without even touching.

Back home, your girlfriend turned on her stream and announced the start of her real-life hotwife odyssey. Her viewers went wild. They’d never seen anyone else with their precious Detroit Cheater Slut. Chuck was a little awkward about it at first, but he grew excited when Winter took her top off and sank to her knees. Ozzie was a natural and began talking up how he would ravage her unsullied sphincter. Winter wiggled in anticipation, leaning over to present her ass. Ozzie pulled off her panties, and spit on her ass for lube. Your girlfriend shivered at the humiliation, even as Chuck forced himself into her throat. She’d never taken you like that. Soon she was truly spit-roasted as Oz slammed his big cock roughly into her virginal behind. She involuntarily cried out in pain and the contractions of her stuffed throat gave your bully’s cock great pleasure. “Pound that bitch, Oz, that felt amazing.” Ozzie eagerly complied, fucking Winter hard and spanking her ass. Chuck loosened up a bit and started talking shit against Winter and her ‘pathetic sissy boy’. He grabbed her by the hair and face fucked winter more aggressively. It was everything she’d dreamed of and so much more.

After they each came, Winter did a little Q&A with the audience. Your bullies got into it, too. Yes, this was real. Yes, cucking her boyfriend felt amazing. Yes, they’d love to do it again. While talking, Ozzie scooped some semen leaking from Winter’s ass and fed it to her. She swallowed it eagerly.

As soon as they each got hard again, Winter let them titty fuck her, slap her around a bit, and even piss on her. Turns out Chuck was into that. At one point they took her ass and pussy at the same time. They were a team now and didn’t mind being close. She told them how much better they were than her boyfriend, coaxing them to fill her holes and lay their claim to her. They both came at once then.

You still don’t understand your girlfriend’s hobby. It’s really desensitized her to the misogyny she railed against only a few months ago. Now when your coworkers organize a bar night, she’ll play pool with your two most hated bullies and get real buddy buddy. “If you can’t beat them, join them, cuck,” said Winter, giggling. It was worse next month when Chuck hosted at his home. Sure, he had a pool and a barbecue, but he also had the privacy for strip poker. You could swear Winter was losing on purpose somehow. And where did she learn to strip like that? And how did she expect to keep playing after she’d already lost all her clothes?

Callie was so angry. Angry that Jordan just got away with treating everyone like trash. Angry that you let him do it. If no one was going to stand up to a bully, then she would. 

“Please, honey, just forget about it. You know how he is. He acts real nice to everyone’s face, he lulls you into a false security, then he tricks you, and later you’re left wondering how the hell he got the better of you. I still don’t understand how he got me to bet my car against him in a game of Flipside. I don’t even think that’s a real card game! But he sure as hell drives around in my Tesla now!”

“Someone has to stop him! And since everyone else is too sissy, I guess it will have to be me”

She stormed off to another one of his stupid parties. Callie wore fancy underwear, a sexy low-cut top and a short skirt. It was an unfortunate necessity. Jordan’s parties were disgustingly popular and he let his gross friends be bouncers. They only let in their male friends and guys whose girls they thought they could fuck. For solo girls…if they didn’t like you or your outfit, they might ask you to flash them and decide if your lingerie was more worthwhile. Callie was ashamed to admit she had done so gleefully, before, when she was more naive and didn’t know what garbage they all were.

This time she showed up alone, full of fire, and Zeek let her in with an approving nod. He did slap her ass as she passed, calling out “Hot one coming through!” Pig. Callie had a few drinks for bravery. Sealed beers, just in case. Then she marched up to Jordan, who had a girl on each side of him, snuggling up. 

“Womanizer! Trickster! Immoral monster! I challenge you! I will beat you and shame you. As reward, I want you to leave this town!”

“Whoa, hello to you  too, Calliope. How’s your embarrassment of a boyfriend? Does he still have that ass tattoo – ‘Jordy’s Bitch’ – I tricked him into getting from the tattoo artist I bribed? Hmm? Well, that’s neither here nor there. You know I can’t resist a game. You got me there. What do I get if I win?”

“You won’t. I am your better.”

“Fair. But then why should I play?”

“Name your price, Jordy. It doesn’t matter.”

“Well, you want me out. Sooo, I guess…I want you in. You’ll move into my humble abode here.”

“What?” Calliope was confused. She was pretty sure Jordan and she had established they hated each other a while ago. He had called her the c-word, she had never forgiven him, and had finally seen his true evil nature. He was a user and abuser. She’d been working to discredit him ever since and he’d been none too pleased. Especially that time she nearly got him kicked out of school.

“There’s a spare room. No worries about impropriety. It’s been open for a few weeks. I need a tenant, is all. You will sign the year lease and move in.”

“That’s weird…but I guess, okay?”

“Shake on it?”

She did.

“I won’t lose,” Callie declared, “I have the perfect game.”

“Oh? But you challenged me.”

“Exactly. I want you gone.”

“You don’t understand. The challenger challenges. They state what they want, what they are willing to wager for. The challenged then picks the weapon, the game, if you will. Right?”

Everyone nodded and agreed. Even people Callie knew were on her side. She was horrified.

“But…no…so…what game did you?”

“Nothing too bad. We go out into my backyard and play Hide and Seek-”

“Ha! I was always the best at that!”

“Let me finish. Hide and Seek, with a twist. We are adults, after all. We need something to make it interesting.”

“Oh.”

“I call it Strip Hide and Seek. It’s simple. You go and hide. For every minute that my friends and I can’t find you, you remove a piece of clothing.”

“What?!”

“Shhh, my pet. Every minute you get to remove an article of clothing hiding that wonderful body of yours. And! You must take a selfie on the minute as proof, and send it to my party Slack chatroom. The hunters won’t look, scout’s honor. But everyone else here will know. If you get naked before we can find you, you win. You are free to go and I will honor my side of the deal and leave town. 

Those photos will be my last sweet reminder of you. 

But if I win, you move in tonight. And I promise you…I won’t stop trying to see more of your body. I will tell your pathetic boyfriend of my intentions and I will dedicate every day to winning your lusts and fucking you.”

Calliope blushed. Honestly, she’d had a crush on Jordan before the big fight. She had no idea he had ever been interested in her, let alone now after she’d spent so much time trying to ruin him. 

No! She shook her head. He was vile and she needed to focus on getting him gone. She could still win. The woods behind his house were vast.  

“Ughh! You are so gross! Fine. I don’t have much choice. Let’s do it.”

They all went out back. Jordan and a couple friends turned around and counted to 100. Everyone else made sure they were logged into the Slack chat. Sure enough, before they were done counting, a photo was posted of Callie. She was looking smug in the hollow of a big tree, her shirt removed. Then the hunters were released. 

Callie was in fact very good at hiding, but sadly she couldn’t have know Jordan had an elaborate security camera array. He and his buds were able to locate her quickly and take some nice video of her darting about and stripping. They made sure to make loud noises in the wrong places, and were rewarded with progressively sexier and confident posing from Calliope.  

She was a little disappointed, really, that it felt so easy. A not so distant part of Callie wanted Jordan to take her. To claim her and shame her. But she pushed those feelings down and basked in the glow of her impending victory. She wanted to make these photos good. She wanted them to be what he fapped to in some distant place, as he ruminated on how she beat him at his own game. 

Just as Callie was about to remove her panties and snap a last photo, Jordan stepped out from behind a tree and grabbed her.

“Shhh, my pet. Shh, shh. You did well, but you lost. You are mine now. And that’s what you really wanted, right? To be my loser? To be my bitchy little roommate with the fiery attitude, who I eventually break and turn into my slut. Who I make cuckold her sissy boyfriend, letting him know he lost completely to a man he hates. A man you yourself despise. Mmm, yes, I can feel you trembling. Let’s go back to the house, your new home. No, no, I don’t think you get your clothes back tonight. They’ve all seen your shameless display already anyway. Oh! But let’s take one more selfie, together, so they know where you’ll be spending your nights now.”

*snap*  

ruthless-lust:

Past is Prologue

It’s true your best friends all fucked your last girlfriend. You wouldn’t exactly say you “let them.” More like she got you drunk and then bet her body in a game of poker against them. You certainly didn’t stop them while passed out drunk. They claim you nodded when she asked if it was alright… After that, she said the barrier was already broken and so she might as well fuck them whenever. You couldn’t really argue. But you also couldn’t believe it was coming back to haunt you with your new girlfriend. Fuck!

The rules were simple. When you collected her from wherever she was, you got to bring her home and fuck her. If you could get her to cry out your name, she was “reclaimed.”

The next time you failed to make her cry out your name, she was “emancipated” and would be free to seek out other lovers. She’d send you little videos of her calling out their names while she came. Eventually she’d get bored of them and ask you to “reclaim” her. 

But this time had been ridiculous. She’s been away a whole month. It had never lasted more than a week. In the videos she’d been moaning “Daddy.” Must be a new kink. Her own father was long dead. Maybe that’s how these kinks got started? You followed the GPS coordinates she’d sent, eventually pulling up to an all too familiar address. …it couldn’t be…your own father’s house.