You Cum You Lose

Author note : For that scene I used Tigger_Lily's story "Melting My Cougar in the Miami Heat" on Literotica. https://www.literotica.com/s/melting-my-cougar-in-the-miami-heat. I only took the extract of the cunilingus and modified it a bit.

A fat red haired man in purple tuxedo, clearly too tight for him, comes to you. His beige trousers marked with brown stripes, too tight despite his chicken legs, his flower pinned to his tuxedo and his ridiculously long hat make him look like a a magician who failed his career. Or a clown who failed his career. Anyway he looks like a man who could never have gotten a job elsewhere. Actually, he does not even look like he works here.

"Hello sir, hello milady" Ok, cliché and cheesy. Who hired this guy ? "I believe you're here to experience pleasures and sensations beyond imagination. Am I correct ?"

"Yes we are" you answer harshly.

"I know because I'm mentalist." Or because nobody comes to a sex dungeon to play monopoly but hey, what do you know ? You're not a mentalist. "Let me propose you a game that is very popular among young couples."

You're about to interrupt him to say you're not a couple but Juliette stops you. She says "my boyfriend and I would like a challenge. A game where we play against each other." While saying that she grabs and squeezes your hand, leaning towards you her boobs compress against your arm but what made waked up your dick is the simple feeling of her head resting on your shoulder and the smell of he hair coming to your nose.

"I see then, please follow me hohoho." Did I mention he has the same voice as Brook in One Piece ?

You follow the man to a room. When you both enter, he closes the door behind you. It is lit with ambient pink lights and the pink carpet is made of fur. It is empty. There is nothing except a chair.

"Young and cute couples like you should be able to enjoy the delicacies of the flesh for long periods of time to satisfy each other and strengthen your bond. Which is why you will defy each other in a battle of endurance through oral sex. I will measure how long you resist climax while your partner gives you oral pleasure. The one who lasts the longest span of time will last the longest. This the TIPS 2 LIPS BATTLE !!!!!!!!!!"

You are at a loss for words before the situation that is unfolding and the catastrophic name this clown came up with.

Your sister however giggles and goes right past you to sit on the chair. She unbuttons her jeans, then take off her panties like it was the most casual thing. She opens her legs to reveal her vagina.

"I go first. Ladies first, right ?"

"Exact ma'am."

"Okay, let's see if my little brother can make me cum."

The old guy stiffens when he hears this you quickly lie to avoid a more complicated development "It's just role-play. We have a shota kink haha."

This woman is too casual about it, she's so playful and confident. Your sister has no boundaries but right now, that is what makes stronger than you. You have to let go of your boundaries too and put everything you have into bringing your sister to climax.

You get to your knees and slowly get your face closer to the pussy. As you put your arms on her naked legs you look at the pussy, smell the pussy, study the pussy. Being so close to it feels different from your previous sexual adventures. You didn't even think about getting that close and how to please a woman with your mouth. Yet you're going to do it. This is your first cunnilingus but you're going to pull it off.

You look up to your Juliette's face to see her lustful gaze expecting a great performance from you. She's fondling her breasts as she's waiting and licking her lips. She's enjoying this. You have to win. You look at the pussy again and focus all your attention on it.

Believe in yourself !

Clumsily, you just shove your mouth and your nose inside her. Without a clue you try to push your tongue in, you try to eat her vagina with your lips without using your teeth but as we should have expected, there is close to no reaction from Juliette. While you continue your attempt at whatever it is you are doing, you look back up to her to see a disappointed face resting on her hand. She's bored. Like she's just waiting for you to realise you're lame at this and stop.

Ok, don't believe in yourself. Believe in ME and I'll believe in YOU ! You just do what I tell you kiddo and we're going to get through this.

You remember American Pie ? You remember the tornado technique for cunnilingus ? Well do it now. Swirl that tongue kid ! Swirl it.

See ? You just heard a *hic* of surprise coming out of her. Now she's looking surprised. That's still not what we want but it's better than bored.

Now, slowly lick from bottom to top, swirling your tongue before you circle back and start again. You know her lovely clit is calling for your attention but you will purposely stay away from it. You need more time teasing her and stroking her sweet folds enjoying the pleasure.

Now she's horny again. Her pussy is reacting by splashing you with her juices and you see her lewd expression conquer her face in lust. She's rubbing her nipples and sticking out her tongue with the ragged breath of a bitch.

She's totally unhibited thanks to you. She wrapped her legs around your neck. I know it's surprising but stay focused as her hips are rising and falling while she moans and whimpers.

"God I love you this way. If only you did that sooner."

You are in total control of her pleasure. Her legs open even more to allow you access. Let your tongue darts here and there, in and out of the folds and openings.

Writhing in ecstasy her orgasm accelerates and her body shivers in convulsive waves. "John, John" she cries. "Yes, yes, yes."

Now slow your motions and she reaches for your head pressing you into her. Sucking softly and steadily you let her control the pressure.

When the orgasmic waves finally slow and dissolve, you pull back, pick up her thong and untangle yourself from her legs.

She looks at you with eyes hungry for more of her brother's body while she recovers from her orgasm.

Once she pulls her mind together, she puts her jeans back on the grab her thong and shove it in your pocket while leaning in to give you a peck on the cheek.

"Now your turn."

She pushes you on the chair and jumps to her knees. In a second, your dick is out and firmly squeezed in Juliette's hands.

"I didn't think you'd managed to make me cum little brother. You're more naughty than I thought." she says while she's stroking your horny cock before licking from the balls to the head all of the shaft with her humid pink tongue. Then she spits on your cock and jerks it again. "And you have a bigger dick than I thought. No wonder mom likes it so much."

You look at the man with the long hat to see if her comment disturbed him but it looks like the role-play thing convinced him. You look at your sister who has her eyes fixated in yours.

"I'm still going to win this. I learned how to pleasure a man in many, many ways."

Little did she know. You modified your body to be able to choose the moment of your climax. The only challenge was to make her cum but since that is done you only have to hold it for as long as needed.

Suddenly, your sister gags when she tries to put your whole dick in her mouth. Only able to put half she still bobs her head up and down to fuck your cock with the bottom of her throat. Thick drops of saliva drip from her mouth. Your sister is really dedicated to give you an orgasm. But it's useless. You ask the guy "How long did it take me to give her an orgasm ?"

"One hour sir."

One hour ?! You thought it lasted five or ten minutes or so. If you hold it in for that long and she doesn't stop before that you're going to have the sorest dick and the bluest balls you ever had.

After some time she finally manages to push all the shaft in. She looks her jaw is about to break while you throat fuck her.

Unable to continue for too long she lets go of the deep throat and prefers to spit on your cock to jerk it thoroughly instead. Now that your penis is all sloppy she's using both hands to stroke you vertically and swirl her fingers around it in the same time too. She was smiling until now but after half an hour she's looking tired and frustrated.

Now she's using her hands and her mouth in unison. She's swirling her tongue like she's vacuuming your dick. Obscene and loud slurping sounds fill the room as a proof of her mastered skills.

She did everything she could , massaged your balls, licked the head, slapped your penis on her face to excite you, she defiled herself to make you more horny as she knew a slut-big-sister would turn you on even the more. But you had an unfair advantage and worked your through to cover her face and hair in loads and loads and ropes of sperm after one hour and three minutes of sloppy incestuous blowjob.

"Congratulations sir you win." You put your jeans back on while your defiled sister is struggling to accept her defeat still coated with your jizz.

"What did I win ?"

"Since you won, you get to have intercourse with.. ME!!!!"

That obese guy flexed his fat and his tight closes literally exploded revealing his naked body and an erect cock pointing at you.

"WHAT THE FUCK ?! WHAT IS THIS PLACE ? I'M NOT GAY !" you screamed then went to the guy to punch him. Then security staff came in before you could hurt him.

"Wha's happening ? You again ? You fucktard that's it we're going to throw you in jail so you never come back here again."

They beat him up then two guys lifted him out of the room.

After that you asked one of the guys "So he didn't work here ?"

"You saw that guy's hat ? Who would hire a guy with a hat longer than himself ? Yet every customer who encountered him got tricked."

"Did they ?"

Your sister joined after washing herself. You're surprised to see absolutely no clot of cum in her hair. She must be used to this you guess.

She sighs "ok you win. I didn't think you'd be that good but that's my mistake. As the elder I'll show example and honour my promise. I'll answer any question you have with honesty."

"Come on, don't look so sad about it." You say while warping your arm around her neck to bring her closer to you. "At least you got to enjoy yourself too."

"Yes I really did."

"Let's go home and I'll ask you my question there."

"Alright."