Jane Bets Her Ass

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Haz 1, 2021 // By:analsex // No Comment

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Jane Bets Her Ass

This story is a smorgasbord of sex. It is an Erotic Coupling that starts at a poker game and then includes oral, anal, a MFM ending as well as hot sex between two “fuck buddies.” If you are seeking more focused fare, please enjoy another story from the many talented authors on here.

I would like to thank Eva_Adams and Red Haired Wonder Woman for the notes and proofing. As always, their help is invaluable.

Thank you for taking the time to read my story, I hope you enjoy it. Let’s play poker!

Jane:

Sitting upon the back of her shapely, naked thighs I looked down at Jane’s porcelain

skin with light freckles dancing across her shoulders, down her back and the top of her tight buns ’til finally teasingly up her inner thigh.

I smiled again at the tribal tramp stamp with the word “seeker” rolling across the dimple of the lower back right above the crack of her butt. She was certainly that.

Her red hair, in a cute, young-looking sorority girl cut, was pulled into a ponytail.

I pried her firm ass open spreading the cheeks revealing her rosebud winking at me. Hairless — like the rest of her sex — with the tender, light brown ring encircling it until squeezing down into her smallest opening.

I stuck my index finger in it to tease.

“Shit! Really, for the love of God. Please stop doing that.”

I popped open the large sized tube of KY I had been hiding and squeezed out a dollop on my finger, bringing it down and rubbing it around her backdoor before inserting my finger in slowly, feeling resistance as her ass opened up begrudgingly. I moved steadily through her rectum until I was all the way up to the second sphincter and stopped there.

“Cocksucker I don’t believe you’re going to make me do this.”

“I don’t care.”

“What if I said I was joking.”

“I don’t care.”

“Your cock is too big. I mean you know it’s bigger than most guys. It will never fit.”

“I don’t care.

“But stop! I have told you no every time you asked for it. You know I’ve never been fucked up the ass before.”

“I don’t care.”

“You fucker!”

“Jane, you made the bet.”

“You motherfucker!”

“You lost.”

Chapter 1:

Jane looked from the cards in her hand to the end of the table and my three jacks, then back down to the aces and 10s she was showing.

She looked quickly at the other five players shaking her redhead in disbelief that she had bet me her actual ass on this hand. “I call,” she said. I flipped over my fourth Jack beating her aces high full house.

“Looks like I’m fucking your ass tonight!”

“Fuck you!” she said as she stood up and heaved the deck with all her strength hitting me right between the eyes.

“Hey! I like the attitude!” I said.

The rest of the table chimed in with trash talk and banter: “Yeah feisty!” “Way to go girl,” “The motherfucker deserved it,” “Hey if you play you lay,” “Don’t be a pussy,” and more.

Most of it was good-natured, jocular, and teasing. A lot plunged into the details of how later in the night I was going to lube up Jane’s asshole and put my big, thick cock way up it and fuck her until I came deep inside her.

Best bet of my life.

She got up from the table, walked to the buffet and poured another stiff gin and tonic, guzzled a bunch down and sat back at the table, and look right at me.

“You willing to go double-or-nothing?”

“Sure. What do you have that tops fucking your redheaded, freckled ass?”

“I’ll blow you and swallow all of it first and let” — she looked around the table — “and let Jim sit in the corner and watch me do. He can even play with himself if he wants to.”

Jim was practically spitting all over himself as I said, “Seriously, you’re going to let Chapman,” nodding over to Jim, “watch and jerk off as you do it?!”

“Yep! But just you and me and I call the game.”

“OK, you’re on. Double-or-nothing! What’s the game?”

“Balls to the wall. Five card stud. Any of you guys willing to front me to a stake?”

“Does that mean I get to fuck your ass too?” joked Mitch.

“No, fuckwad! I wouldn’t have bet my ass the last time if I had any dough left.”

“I’ll stake you, Jane,” said Chapman pushing some chips towards her, knowing where his bread was buttered.

One of the guys said, “Side bets allowed?”

“Yeah. What the fuck.”

The guys started whispering to themselves pulling out $20s and $100s.

Jane nodded to the left, “Kenny, you shuffle and deal.”

He did, we cut, he dealt both of us hole cards, and threw Jane a jack of clubs and a 3 of diamonds for me.

Kenny, as the dealer, said, “Jack is high. Jane’s bet.”

I looked at her and said, “Seems only right since it’s your double-or-nothing. Bet.”

She pushed four blue chips, a hundred. I called.

Jane got an 8 of hearts and I got the 7 of clubs.

More betting.

Her third up card was the 8 of spades canlı bahis and I got the 4 of diamonds.

“Looks like you’ve got a pair over there,” announced Kenny. The table started howling. “Will you all shut up! What’s your bet?”

“I’ll check to the straight,” and Jane smiled.

“$500.” And I pushed about half of my stack forward. “And if I lose, I’ll eat you until you cum in front of Chapman and he can still jerk off!”

“You’re not expecting some kind of matching bet on that are you?”

“Not if you show me your pair right now and I’m not talking cards,” and I smiled my most devilish grin.

She pulled up her T-shirt, flashed the entire table both perky, alabaster Cs, gave me a special shake, and threw $500 into the middle of the table.

“You’re on and I can’t wait to see him give you a facial while you’re between my legs!”

“Hey! That wasn’t in the bet!”

“It is now!”

Chapman was smart enough to let it play out. He was getting off no matter who won.

“You know I fucked Jim once. Yeah, after the department’s Christmas party. He’s insatiable, never gets soft, and came three times. What do you think of that?”

“I think after you lose this hand to me he’s only going to cum once!” and I looked at Chapman, stuck my tongue out and buzzed him a raspberry.

“You are a dickhead,” Jane said as she pulled the 8 of clubs giving her three 8s. I hit a 6 of hearts. The table buzzed.

Kenny said, “Bet goes to the 8s.”

“You got that inside straight?” asked Jane searching for my tell.

“There’s only one way to find out. Got the balls, Red?”

Jane counted her remaining chips then pushed them into the pile.

“OK, that’s everything I’ve got. $245.”

“You can have more Jane if you’re willing to throw another assfucking my way,” laughed Mitch.

She flipped him the finger.

“OK, I’ll call,” I said putting my $245 into the pot. “Show.”

The room became still as Jane peeked at her hole card, looked up towards the sky as if in prayer, and flipped over the ace of hearts.

“Three 8s,” announced Kenny.

Jane looked hard at me. “Well?”

Everyone looked at me in nervous anticipation. I paused for dramatic effect, took a peek at my hole card, peeked at it again, did the same look up to the sky as Jane.

“Are you going to show it motherfucker or what?!”

“Read ’em and weep,” and I turned over a 5 of spades.

Jane looked crestfallen as she dropped her head shaking no slightly.

“Fuck! He hit the inside straight,” I heard Chapman shout.

“Your lucky night, Jim,” I said shaking his hand.

“No shit!”

I looked at Jane. “I’ll tell you what. To be nice, rather than tonight I’ll see you at my place next Saturday night. Shall we say around 8 o’clock? I’ll get some drinks and a few snacks. It’s gin for you, right?” I grinned.

I looked at Chapman, “Jim, guess I’ll see you there too. Maybe a bit earlier to have a beer and settle in?”

Chapter 2:

We heard the knock on my door around ten after eight. I gave a quick look at Chapman, “Got your cock ready?”

“You bet your ass!”

“Nope, that’s what Jane did already,” I laughed.

I opened the door and Jane was standing there acting as if she was ready for anything we could throw at her. She sashayed into the room with aplomb and style.

“Good evening, gents.” She looked down at the bulges in our pants. “I see the two of you eager young lads are fervently awaiting to have your fun.”

She was standing there wearing a Brunello Cucinelli pailette open-knit sweater, and a short, pleated wool skirt, tight around the waist with three large buttons on the side holding it closed.

Jane had the amazing ability to bring grace and elegance into any room she entered.

She kicked off her flats with a flash of nylon stockings on her feet.

She glanced over at Chapman who was wearing his typical uniform of T-shirt, loose jeans, and boots. “Evening Jim, I see you’re dressed for the occasion.”

Jane turned back to me, “At least you know how to dress.”

It’s not like I was in a tux, but I was wearing a styling silk shirt from Ted Baker, the London designer, and a tight fitting pair of black Levi 501s. You know, the kind with the button fly, and a pair of Pinch Weekend Cole Haan loafers.

“Got that gin you promised?”

“Back here in the kitchen. Want to join?”

“No thanks. There will be more than enough ‘joining’ here later. On the rocks and don’t forget the splash of tonic.”

Fixing the drinks in the kitchen I was marveling at Jane’s composure and unabashed sexiness. Granted the red hair, my most serious kink, and shorter height, the fit figure with the great tits and tight, slender ass. She also had great legs with — and this is an antiquated term — well-turned calves. But it was her brain that I always found the most attractive.

I’ve always been a sapiosexual, sexually attracted to intelligence. I’m much more turned on by big brains than big boobs. (Though don’t bahis siteleri get me wrong. Big boobs are nice too.)

But give me someone who is super smart, who knows how to use their intelligence for something more than inventing super batteries, and enclose it in a pretty face and I am like a dog chasing a bone. Or should I say, I’m a dog with a boner?

It’s fun to play with a vacant girlie-girl for a night or two and I have many times. They can be great lays with amazing sexual appetites, but at some point you have to talk. I mean you can’t have your cock in their mouth all of the time you are together. Can you?

I need a sparkling conversation and someone who can challenge me in a discussion. By the way, talented and accomplished help too.

Yep, big brains make my cock big too .

I sensed Jane walk into the kitchen behind me, lean up against me pressing her breasts into my back, wrapping her arms around me.

“Are you really going to make me go through with this stupid bet?” she said as she tiptoed up and nuzzled on my ears while she brought her hand down to what she knew was my hard cock.

Jane also knew where to find it since I dress left and she was left-handed.

“Actually yes, I am.”

“You asshole,” and she pushed me spilling the gin.

“There you go wasting perfectly good booze over something as minor as a serious assfucking,” and I smiled.

She smacked my butt hard. “Give me my drink dickhead.”

I did, turning to her.

“I thought you’d cut me a break since we are friends.”

‘Well, it was a friendly game of cards.”

“Yeah sure, but we are also friends who occasionally fuck, in case you forgot.”

That I couldn’t forget. Laying on top of her, looking down on Jane’s classically beautiful face framed by her red hair, those perfect C-cup tits and the flaming red landing strip leading down to the shaved vagina that was so tight it had to stretch every time that my cock ventured into its sweet, wet depths.

“Can’t say I forgot that,” I said chuckling.

“You are a dickhead,” and she smacked my butt again.

“Hey, that hurt!”

“So what’s your plan? I’m going to strip off my clothes, get on my hands and knees on your bed, and you’re just going to fuck me up the ass as Jim jerks off?”

“No. Actually my plan was a little dinner and drinks, and watching some of the game first. I bought mid-Eastern, some hummus, tabouleh, Dolma — you know, stuffed grape leaves, my fav, baba ghanoush, and baklava for dessert. Plus pita bread ’til your heart’s content.”

“The Dodgers are playing the Giants, and I’ve got a jug of Bombay for you, a fresh six pack for Chapman, and Maker’s for me. Then I thought you’d strip off your clothes, get on your hands and knees on my bed and I’d fuck you up the ass as Chapman jerks off!”

“You insufferable asshole! Have you a least set the table?”

“I was hoping you’d help with that and putting out dinner,” and she smacked me again.

“Ouch! Seriously, that hurt.”

“Good!”

A number of drinks each, a few runs for the Dodgers, and a lot of mid-Eastern chow later our conversation had drifted into conquests and rejections. Mostly Chapman and I bragging about our conquests, and Jane bluntly describing who she had rejected and why.

“Yet, you didn’t say no to Chapman over here,” I said pointing his way.

“Hey, wait a minute,” he protested. “When did I become the subject of conversation? I’m just an interested observer here as I recall,” he said with a wink.

“You became a subject when you fucked her three times.”

“Who said it was only three?” That wink. “Anyway, I don’t think I’m the only one here. The word is you two have some kind of a friends-with-benefits deal going, and, may I remind you, you’re the son-of-a-bitch who’s going to fuck Jane’s ass tonight.”

“Well, maybe. We’ll see.” I nodded in agreement and looked at Jane. “Time to come clean. Did you really fuck him or were you mocking the guys around the table?”

“Oh yeah. We fucked,” and now she gave Chapman a wink.

“I had a little too much to drink at last year’s Christmas party — you know me and parties — Jim was kind enough to drive me home and somehow my hand landed in his crotch.”

She looked over to Chapman, “He’s got a great package! And before I knew it my head was also in his crotch and his impressive cock had somehow been freed from those damn jeans he always wears. And you know, there is just something so hot about giving a blowjob in a car when the guy’s driving, particularly when his cock happens to be out there swinging in the breeze,” Jane smiled.

“You know, it’s taboo, dangerous, arousing as hell, and challenging because you’ve got to bob enough to get to the finish line while avoiding the damn steering wheel, center console, and stick shift. And then, you’ve got to swallow it all without making a mess in case the cops pull you over.”

“Anyway, this guy’s cock never goes down, and we hit it two more times that night at my place,” she gave bahis şirketleri Chapman a lascivious look.

Jealousy kicked up in me, “Well, the good luck for me tonight is Chapman didn’t make the bet.” I pointed at the easy chair, “Dude, get your butt over there and get yourself ready.”

“Alexa, play something romantic.”

“Here’s something you might like, ‘Music For Lovers’ from your playlists.”

I handed Jane her Bombay and tonic, grabbed my Maker’s Mark, clinked our glasses and said, “Time for you to pay your bet.”

“Are you really going to make me do this?” she whispered.

“After your Chapman tale,” and I shrugged.

We chugged our drinks and I led her over to the bed and I started to kiss her as my hand moved from Jane’s back to her breast, then the small of her back, and down to her tight ass. Along the way, I unbuttoned her sweater, got the bra hooks undone while under the sweater, and unzipped her skirt.

My hand moved to the buttons in the front of the skirt as my tongue moved deeper into her mouth and Jane’s skirt hit the floor.

“That was pretty deft. Do you have other tricks up your sleeve?”

I lifted off her sweater and bra in one move.

“Impressive. You’ve become a regular David Copperfield!”

She was standing there exquisitely naked except for white nylon, thigh-highs and a matching white thong accentuating her lithe body.

I glanced over at Chapman whose jeans and underwear were off. It looked like Jane was right about his always being ready. His cock was standing at attention, and even though I’d see him plenty in the locker room, I had never seen him hard. Jane was right again, he had an impressive package.

I laid down across the bed, patted it, and said, “I think you should join me.” She nodded slightly and started to roll down the thigh highs. “Keep those on, please, but the thong can go.” It did.

Jane stretched next to me with her auburn tresses flowing above her head. So provocative. Her lightly freckled natural breasts were perfection, firm, high on her chest with perky nipple pointing upward. Jane’s tummy was flat with a small diamond dangling on a platinum chain down into her pierced belly button. (She was even tasteful when it came to her belly button ring.) Her firm ass looked as if it had taken thousands of steps on a Stairmaster.

“Anything you finding especially pleasing?” her voice dripping with sarcasm.

As if that was a question. She knew I found it all pleasing.

“Yeah! I’m lovin’ the fact that you wore that butt plug for me tonight. It’s hot especially with that red jewel sticking out between your cheeks.”

That got Chapman’s attention! “Anything getting you off yet, Jim?” I asked.

“God, you really are a dickhead,” and she pulled her knees up to her shoulders to demonstrate that there was no butt plug. And I dove down to her fully exposed rosebud, spreading her cheeks wider, and gave it a few long, slow, loving licks.

“For later,” and I moved up to her pussy.

I lot of guys don’t seem to like eating pussy. I don’t understand that. I love pussy. The mystery of how it unfolds. The clitoral hood hiding the gold mine. The soft vulva that gets so red when aroused, and how the lips emerge. Every woman’s is different like every guy has a different dick. Some are small, short with almost no lips, some are long and alluring, some are asymmetrical, some are fleshy and robust.

My hands slid down her thighs caressing the slick sexiness of the nylons. I took a long lick up her slit to her nub and rolled my tongue around it, feeling it become fuller and more present, then shoving my face into her sex drinking her in while inhaling the richness of that pungent odor unlike no other.

I love the smell of women’s pussies. Sweet yet acidic. Repellent and yet, the most intoxicating, arousing scent known to all mankind. Its power to bring on your most primal and animalistic urges.

I read somewhere that an aroused pussy “smelled like a butterscotch river cutting through a field of wildflowers, along with the soft powdery muskiness that was the scent of her skin.” I love to dive my face into a woman’s cunt and inhale deeply taking her scent into my nose as it shoots straight into my brain and right down to my cock in an electric shock.

I put my left index finger on Jane’s clit to a low groan and gently spread its hood taking her button into my mouth. I licked around making her more and more aroused while slowly putting my finger into her very wet snatch all the way to the bottom, and started to finger fuck her as I got back to licking her delicious clit in long strokes.

It became more excited growing in width and length. I took her into my mouth, squeezed my lips tightly around it, and started giving Jane’s clit a blow job moving up and down as if it was a small cock.

Her hips started to buck in and out and move in a circle reminiscent of the dancer she once was before she became a playwright. The sensual circles worked in perfect harmony with the circles my tongue was making around her clit, and she started to moan in rhythm with her hips.

I moved my mouth tighter down onto her cunt flattening my tongue against her clit licking it very, very hard and fast.

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