The League S1E5: The Usual Bet

This, and all my other stories, are planned to be standalone stories set during episodes of TV shows. Any events or situations from other stories do not roll over unless stated.

The set up for these stories may be ridiculous, so if super realism is your thing, I apologize.

If you have any story ideas based on this show or others, that you can explain don't be afraid to post a comment/shoot me an email and I'll see if I can add it to my list of ideas.

This is set in the TV show The League on FX. It will focus on the character Jenny.

I would like to thank Pyrofanity for editing.

*

"I thought I had it this year," Kevin muttered dejectedly, lamenting on not making it to another one of his fantasy football playoffs. "And now it's just... it's over, so-" he tried to continue.

"Well, it's not officially over, actually," Pete interrupted with a smirk on his face "There's still the small matter of the bet."

"You didn't make that same bet again?" Jenny asked to her husband while shaking her head at him.

"It's weird though, the usual bet may have to take an unusual turn this year due to the fact that I technically did not really run my team." Kevin answered, a devilish smirk coming across his face.

"That's an excellent point." Pete said, catching on to what Kevin was doing.

"Jenny, you have made it emphatically clear that you set the lineups," Pete explained, "You do the trades. You do most of the work, so..."

"You're really gonna make me do this?" Jenny asked incredulously.

"Yeah." Kevin said shrugging his shoulders innocently.

"You always say you wanna be one of the boys, Jenny." Pete chimed in.

Jenny, however, was not one of the boys. Her brown, lightly-curled hair snaked down her very pretty face to rest just below each of her shoulders. Her breasts were on the smallish size, but still quite perky. Her ass was probably her best asset, big enough to jiggle but tight enough to bounce a quarter off of.

"And boys do stupid things like get naked in alleyways," Kevin explained. "For a minimum of two minutes," Pete finished his thought, a grin on both of their faces.

"Don't worry though, I'm gonna hold your purse and your lip gloss," Kevin added in reference to her emasculating remarks earlier in the night.

"Fine." Jenny said. She was determined to be one of the boys. She pulled her scarf and hat off and threw them at Kevin.

"No...?" Kevin asked in disbelief. He couldn't believe that she was going along with this. "A bet's a bet." Pete answered for her, as Jenny took off her coat and dropped it into Kevin's hands.

"You ready?" Jenny asked, untying her dress from the front, making it easy to take off. "You sure?" she continued to Kevin, and before he could answer took her dress off and threw it at him.

"Two minutes," she finished, pulling her bra off, and dropping it in Kevin's hand who now had a completely baffled look on his face. He thought there was no way she would go through with this, but here she was practically naked walking down an alley.

"Wow, she's actually doing it." Pete exclaimed watching Jenny walk away wearing only boots and her panties. "A bet's a bet." Kevin simply answered, echoing Pete's words from earlier.

As she walked, there was confidence in each step along with a jiggle of her ass. She wasn't looking forward to this, but she also was willing to do whatever it took to be taken seriously by the fantasy league of which she desperately wanted to be a part of.

It was a cold night and her nipples were already as hard as diamonds and sticking straight out. She could feel her ass shake with each step, and was for the most part feeling pretty good about how she was looking at the moment.

She walked a bit farther then she thought she would and turned to head back, where she noticed that Pete and Kevin were gone, almost certainly inside watching the game. She saw her clothes on the ground beside the bar and started to move towards them. Shaking her head in anger about Kevin leaving her out here like this.

As she neared the bar, two men walked out the back joking about something or other until they turned and saw a naked Jenny walking towards them. Both were tall, a bit over 6 feet, and musclebound. One was black and the other was white, but both had the same reaction when they saw Jenny.

They stopped in their tracks and stopped speaking, their mouths hanging open a bit at the sight in front of them. Jenny gave them a little smile and shrug as if to say, "what are you gonna do?" She then moved to walk past them shaking her ass a bit more to give the boys a little show.

The white guy grabbed her arm, turning her towards him, and said, "Hold on a second pretty lady, I'm Randy and this is my friend John," he gestured at his buddy. "You need any help, or maybe a little company?" He asked, a smirk on his face.

"No, I'll just go get my-" Jenny started to say while backing up, until she bumped into John who had moved behind her. His right hand slid up her side and grabbed her tit, immediately feeling how hard her nipple was. "I think she does want something Randy, and I think we got just the thing." John commented with a broad smile and he rubbed the bulge in his pants against Jenny's panty-clad ass.

Jenny was a bit scared, but most of all she pissed. Pissed at Kevin for making her do this, for putting her in this situation, and then leaving her, but as John rubbed against her ass she felt a new sensation, arousal. She could feel just from the bulge that it was a bigger dick then any she had ever seen or felt. Words failed her as John continued to grind against her and slowly started playing with her tits.

"I can't, ohhhhhh...," Jenny started to say, before Randy had placed his hand over her crotch and started to rub her pussy through her panties. "I shouldn't...." Jenny tried again, this time with much less resolve, her pleasure increasing along with her anger at Kevin.

"Your pussy is telling me you should." Randy says, in reference to the wetness he could feel through her panties. With his free hand, he cupped her face and brought it to his, giving her a passionate kiss. This broke the last of Jenny's resolve and she fell into the kiss.

She felt John's hands move up to her shoulders and gently push her downwards. She broke the kiss and moved downwards with the hand's momentum. She finished in a crouched positon and looked up to see the boys had flanked her on each side.

They both proceeded to start unbuckling and unzipping their pants, letting them fall to their ankles. They took their underwear down around the same time too, unleashing to Jenny the two biggest cocks she had ever seen. John's was around eleven inches, but only a bit thicker than Kevin's, while Randy was twice as thick as John's, but only slightly larger than Kevin at around 8 inches.

They each grabbed the hand of Jenny nearest to them and placed it on their cocks and even started stroking them for her. "I got it boy's don't worry," Jenny said, giving each of them a wink as they let their hands fall away.

She tugged slowly on each and marveled at their uniqueness. Her hand couldn't remotely wrap around Randy's and the time it took her to do a full stroke on John seemed like it took forever. She slowly sped up her strokes while licking her lips in anticipation of what was next.

She slowly bent forward and ever so gently licked just the tip of each, just teasing them. It earned a groan from each and a smile from her. She then licked down the shafts of each ending with the balls which she gave a little kiss to.

John reached down, probably to encourage her to speed up, but Jenny slapped his hand and chided him, "If we do this, we do it my way." She took the head of Randy's cock in her mouth and momentarily stopped stroking John to punish him.

"Ok, ok pretty lady, you're in charge I'll just sit back and enjoy." John pleaded, a smile on his face when Jenny took his head in her mouth.

She kept pushing forward on John though, getting about halfway through before feeling a need to breathe. She turned her attention back to Randy making sure to get back to fully stroking off John throughout. As she pushed past Randy's head she could already feel how much it was stretching out her mouth.

At the halfway point she knew she wouldn't have a problem with the length but already she could feel this monster cock had stretched her lips to their limit. She slid her tongue out under it and tried to push her drool out onto the rest of it to ease its passage. She pushed herself further and further onto it, feeling her hand had less and less room to jerk him off. This continued until her mouth hit her hand.

She gingerly pulled her hand off his cock and placed it on his leg to steady herself. As she pushed herself further and further Randy commented, "That's it slut just a little bit more." She moaned into the cock to confirm what he said. The comment did motivate her to push herself the little bit extra and she felt herself reach the end. She could feel her cheeks were impossibly pushed out.

She bobbed her head on the end of it for a bit before John piped in, "Alright slut, you took him, now it's my turn." He gently took her head and pulled her off of it with a loud plop and a long string of spittle was hanging from her wet mouth. This time she led him using her head without complaint.

She placed her lips around his head and mentally prepared herself for what she was about to do. She engorged herself on his cock, initially with great gusto. After stretching and managing to take Randy's dick, the first six or seven inches were quite easy, but then she could feel it starting to get near her throat and she got worried.

She focused on jerking Randy off for a moment and breathed in her through her nose, getting ready to try and take all of John into her mouth and throat. As she got back to John's cock she noticed she had slid out about two inches of it and quickly recovered that distance, slobbering all over the cock.

John was moaning in pleasure as she forced the cock down her throat. Inch by inch she pushed it into her. She snaked her hand around and grabbed the back of his leg to push herself with more pressure. She felt it hit the back of her throat with very little left to go and she repositioned slightly so it could go down further.

She pushed and pushed, feeling John's hand helping her get the last little bit in. When she finally managed to get the last couple inches in, she heard a loud moan from John.

As she finally managed to take all of John's cock in her mouth, she could feel his pubes tickling her nose and his balls slap against her chin. As a happily married woman, she should have felt humiliated, distraught, or like she was betraying Kevin, but all she felt was pride.

John commended and commanded her saying, "That's a good slut, now look up at me." She immediately obeyed looking straight into his eyes as she slowly started to bob on his cock.

Randy was getting impatient though and pulled Jenny off of John, leaving his cock hanging obscenely dripping with her saliva. She grabbed it with her hand and went back to stroking as Randy shoved his cock in her mouth and she quickly was able to take it all.

She planted her hand on him for balance as he took her by the side of her head and slowly started to fuck her face. He picked up his pace as he noticed her ease at taking his cock now that she had fully taken both of them.

His pace quickened as saliva and her hair flew everywhere. He was now full-on fucking her face and could feel his orgasm approaching. Before he could finish though, John started to pull her away.

As her head moved away, Jenny's hand flew back onto Randy's cock and slowly jerked him off keeping him just on the edge of an orgasm. John repeated what Randy had just done, pushing her all the way down on his cock, much quicker than last time. Unlike Randy, it was taking him a while to train her mouth to quickly be able to take his cock.

He could hear her gagging and saliva dripping down her chin onto her chest, but he paid no mind. He was determined to fuck her face and he kept at it. Slowly increasing the speed at which he pulled it in and out of her throat. She did all she could to accommodate him but at this point the control was in his hands.

His pace quickened and he bent his body slightly over for better leverage. He grabbed her head by the top of it with one hand and right under the chin with the other. She pulled her hand off of Randy's cock knowing she needed both on John to keep her steady.

All of this allowed John to start fucking her face as fast as he could and he was happy to oblige. He rammed his cock down her throat without mercy letting out a guttural roar in the process. Jenny, for her part, simply kneeled there and took it.

As John neared an orgasm, he considered depositing it all in her mouth but had a better idea instead. He pummeled her face for a little while to get himself right on the edge. He motioned for Randy to do the same to himself. Then, without warning, he roughly pulled his cock out of Jenny's mouth in one tug.

The dick popping out of her mouth startled and relieved her. She gasped for breath as her hands automatically went to each of their cocks as if it was her second nature now. She jerked them off for a little while before they pushed her hands off and started to do it themselves while positioning themselves directly in front of her. Whether it was out of exhaustion or not understanding the situation, Jenny did nothing to stop what happened next.

Her mouth was still agape from the pummeling it had just endured and as both their cocks exploded around the same time, spurt after spurt landed on her face, chest, and some even managing to make it in her mouth. It seemed to go on forever, she could feel it dripping down her face and chest down to the rest of her body. By the end, she felt drenched in it.

The boys looked down at their work and smiled. Jenny gingerly took her hands and wiped a bit of the cum away from her eyes and opened them slowly. She noticed both their cocks were still leaking a bit of cum, and without thinking she moved her mouth forward and cleaned them both, giving their heads a little kiss as she finished.

She smiled weakly up at them and made a show of swallowing all the cum that had gone into her mouth. She used her hands to wipe and clean off most of her body and face and gave the boys a treat by eating each handful she brought up. She sat kneeling catching her breath and resting up while planning to get up when she was ready and go get her clothes to get dressed.

As she moved to get up and started walking towards her clothes, she felt both of them place a hand on her to stop her. They each grabbed a side of panties nearest to them and slowly pulled it down, both noting how soaked they already were. Jenny was mad enough at herself for sucking them off and didn't want this to go further.

She tried to push their hands away or say something, but she found she didn't have the strength to do either and she could feel how sore her throat was. She tried to simply walk away, but only ended up stepping out of her panties leaving her wearing nothing but her boots.

They held her back from walking any real amount away and Randy said, "Whoa girl, we ain't done with you yet." He turned her to face him and gave her an evil grin.

Randy moved behind her and grabbed both of her hands. He held them on the small of her back with one hand. The other he used to gently push her to be bending over until she was at almost a perfect right angle. Jenny knew what was coming, but feeling how horny she was, did nothing to stop or discourage him.

He teased his cock up and down her pussy, pulling a moan out of her with each pass. He could feel how wet she already was and as he put his cock's head in positon to go in, she backed into it. It slid into her pussy and she shivered a bit feeling the monster enter her. Despite how tight she was, he kept pushing forward without a problem due to how incredibly horny she was.

Inch after inch pushed forward and she moaned in disbelief at how quickly he hit uncharted territory inside her. She had never had anything more than eight inches in her cunt and now had nearly ten of his hot rod deep inside of her. She looked back at John in amazement as the last inch or so entered her.

As soon as that happened Randy pushed Jenny's face down to his crotch and Jenny eagerly engulfed his still wet dick. She could feel John slowly start to fuck her and she did the same with her mouth. She tried to keep up her pace with John who was finding her pussy was much quicker at accommodating him then her mouth was.

He reached around and roughly grabbed one her of tits while Randy grabbed the other. Randy's other hand roamed to Jenny's head where he started dictating the pace of her sucking and she noticed that it quickly increased.

She was now being roughly spit-roasted and was loving every second of it. She could feel an orgasm quickly approaching and slammed her body forwards and backwards to meet the cocks impaling her. Her smooth ass cheeks were now bouncing wildly each time John fully entered her and her hair was doing the same for Randy.

She came suddenly, shaking and shouting into the cock in her mouth and the boys never slowed down to heighten the experience for her. She slowly came down from it and went numb in the boy's grasp. John came up with a little plan of his own and communicated it with Randy, who roughly pulled his cock out of her mouth. John pulled out of her too and turned her to be facing him.

John lifted her entire body up with ease, one hand grabbing her ass cheek the other on her shoulder. She threw her arms around his head, startled by the sudden shift in her position. She also managed to throw her legs around his waist. He roughly slid his cock into her used pussy and started hammering away at it.

She was holding on for dear life, but was immensely enjoying the pounding she was getting until she felt another hand on her other cheek and both slowly pulled them apart. She felt Randy's cock slide up and down her ass, teasing her asshole.

"It won't fit," she moaned in fear. She hadn't taken anything up her ass since college and certainly nothing as large as Randy's cock.

Randy answered by placing the tip of the cock on her asshole and slowly sliding the head in. She yelped in pain, but Randy paid her no mind. She could still feel his cock was covered in her salvia which she was very happy about at this specific moment.

He dutifully pushed forward ever so slowly, amazed at how tight she was. In no time at all, Jenny felt the entire head had pushed into her ass, along with a bit of the shaft. His girth felt like it was tearing her asshole apart already, but she knew nothing she could say would stop him at this point, plus she felt after the events earlier in the night she could handle just about anything.

Randy crudely spit down onto his cock adding a bit of extra lube as he moved further into her asshole. She cried out with each shove of his cock into her, but Randy simply ignored them because he was greatly enjoying her tight, little asshole.

He was now well over halfway inside of her and she was biting her lip to stop herself from screaming too loudly. Inch after inch brought her immense pain and pleasure. He kept at it though and she could feel the heat radiating off his body getting closer and closer as the cock got more and more into her. He reached around and grabbed her tits as the final inch entered her and gave her nipple a flick and let out a loud moan as he fully entered her asshole.

He quickly pulled it all out of her, getting a loud moan of response from her. He repeated his earlier process and slowly shoved it in. This time Jenny noted that the pain was far less prevalent than the pleasure.