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Bet Your Bottom

Category: Anal Sex
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“I can’t believe you’re making me do this,” Natalie said as she stood on the hotel balcony at three a.m. with the wind blowing through her strawberry-blonde hair. Her eyes scanned the parking lot, and though she didn’t see any signs of life, someone down in the darkness would be a lot harder to see than she would be on the balcony — dimly lit as it was.

She could see the excitement in Gene’s eyes as he caressed her shoulder. “You lost the bet fair and square.”

“We are so going to get arrested,” she said as she tugged at the bottom of her t-shirt.

“Nobody’s going to see us. Or are they?”

Even though she was arguing, the truth was that she was as wet as she’d ever been in her life. The possibility of getting caught was turning her on. Reasoning that the longer she hesitated, the better the chance that someone would happen along, she pulled off her shirt to bare her breasts.

“God, you look great,” Gene said as he turned on the camera and pointed it at her.

Anxiety and arousal both surging within her, Natalie pushed down her shorts and panties before sinking to her knees in front of him. Now stark naked on a hotel balcony where anyone in the parking lot or on the beach beyond could see her, she hurried to jerk down her boyfriend’s shorts. He was hard as a rock and twitching in anticipation as he recorded the whole thing.

“Do it, baby,” he growled under his breath.

She gave his erection a few licks to wet it, but under the circumstances, she wasn’t about to waste long teasing. He groaned as she parted her lips and took him in.

Natalie let out a moan when a drop of pre-cum lit up her taste buds as she pulled back to the tip the first time. She was tingling all over.

“Let me see your eyes.”

She looked up at him — and thus directly into the camera — and teased the head of his cock with her lips and tongue.

“Oh yeah. Now suck it.”

Cupping his balls in her right hand, she took him deep and moaned again when his hand settled on the back of her head. Turned on beyond belief, she sucked him hard and fast, her hair bouncing and tits jiggling from her efforts.

Gene grunted, “You like it, don’t you?”

“Mmm hmm,” she moaned in answer without pausing.

“Fuck, you’re so good. So fucking hot.”

Some girls saw a blowjob as a necessary evil. Natalie wasn’t one of them. She loved the feeling of him throbbing against her tongue, his fingers fisting in her hair, and his hips bucking beyond his control. It was both submission and control fantasies coming to life at once. On the one hand, she was naked on her knees, fulfilling her obligation to a lost bet. On the other, she knew full well that as long as his cock was in her mouth, she owned him.

Fingers between her legs, teasing her own need, she sucked for her reward, and the satisfaction of their bet. His grunts growing louder and hips trying to push his cock into her throat let her know he was close in a surprisingly short time. Feeling incredibly sexy, she let one finger creep along the bottom of his balls, and then beyond, wondering if he’d let her do it this time.

As she more or less expected, he pushed her hand away and grunted out a quick, “Nuh uh.”

She knew that if she kept pushing, he would let her, but she didn’t want to make him uncomfortable. Besides, he was on the brink.

“Now,” he growled.

Natalie let his cock slide from between her lips and took it in hand. Opening her mouth wide and sticking out her tongue, she stroked his slick member.

It didn’t take much.

A grunt that was too loud for where they were escaped him as he erupted. The first spurt missed her mouth completely, leaving a sticky trail on her cheek and neck. The second went straight into the back of her throat, making her croak, but she kept her mouth open and her hand moving. He filled her mouth and spotted her face with his hot cream before the squirts turned to dribbles. She shook the oozes of cum from the head of his cock onto her tits, and then dived back in without warning.

“Shit,” he spit out from between clenched teeth as she took him deep in her still cum-filled mouth. A little dribbled out the corners of her mouth to drip onto her breasts as she pulled back. He immediately jerked away when she reached the head, and bumped into the privacy wall behind him.

Natalie swallowed and licked her lips as Gene lifted the camera in a trembling hand to film her cum-covered body. For a few seconds, she didn’t care where they were, or who might be watching. She smoothed his cream into her skin, smiling at the camera and shaking her tits.

The sight of headlights in her peripheral vision got them both moving quickly enough.

Back inside, with his pants still entangling his legs, Gene collapsed on the bed. Natalie tossed her own clothes to the floor as she closed the curtains. She turned back to him and said, “Oh no, you’re not leaving me like this.”

He didn’t really protest when she straddled his face.


Pulling up into the parking lot of their apartment the next morning, Gene tapped on the dash and said, “Don’t forget to put gas in before you go to work tomorrow.”

Natalie rolled her eyes and let out an exasperated sigh. “I’m not going to forget and run out of gas.”

The amused look on his face was enough, but he still said, “Oh, really? Seems I’ve heard that before.”

She stuck her tongue out at him and climbed out of the car. He followed, and anticipated her playfully shutting the door in his face, ruining that little protest with a foot in the doorjamb.

They’d both awakened horny, but with not enough time to do anything about it before check-out. Natalie was thinking about remedying that when Gene asked her. “Want to watch the video?”

“God, I don’t know,” she answered with laughter in her voice.

“Come on. You looked fucking hot.”


He hooked up the camera to the television, and then sat down on the couch next to her with the remote in hand. She didn’t even wait for him to hit play before reaching between his legs.

She had to admit that she looked incredibly sexy swallowing his cock on camera, and even more so with his cum spraying all over her. Of course, that last part of the video was a little shaky.

Having already wormed her hand beneath his shorts while she watched, she said, “You should let me… You know.”

He winced a little. “It just doesn’t do anything for me.”

“That’s because you haven’t tried it. Trust me.”

“Oh? And how many times have I asked you?” He reached down and squeezed her butt, leaving little doubt that he was talking about asking her for anal.

“That’s different. I told you that I had a bad experience.”

“Because the guy had a donkey dong and was drunk off his ass.”

“I know you wouldn’t be like that, but it still makes my stomach do flip-flops when I think about it.”

“Same here. Besides, sticking your finger there is just — eww.”

She lifted her eyebrows and gave his cock a squeeze. “And sticking this there isn’t?”


The most delicious thought popped into her head at that moment, but there was too much tension in the air to spring it on him just then.

She knew exactly how to take care of that.

Gene forgot all about the preceding conversation as she climbed on his lap and pulled off her shirt.


Face down on the sheets with her butt high in the air, Natalie shivered from the final ripple of orgasm passing through her. She could feel his cum dripping from her onto the sheets and running down her legs, but she didn’t care.

Gene lay groaning next to her, his cock still half-hard and his eyes closed. It had been one of those rare, magical occasions where he’d held out forever. She had been into her third or fourth onslaught of multiple orgasms before he buried his cock inside her and filled her full of cum.

A whimper escaped her as she moved, letting her knees slide until her butt sank down and she could roll over. She snuggled up next to him, and relaxed in the afterglow for a few minutes.

Once they had both caught their breath and shared a few kisses, she decided the time was right. This was a trick she’d used more than once, and it never failed to work. He was as tractable as a kitten held by the scruff when she’d milked every drop of cum from him into her mouth or pussy.

“Bet you I can go a month without once running out of gas. And, without you reminding me all the time.”

He chuckled. “I’d like to see that. Real bet?”

“Mmm hmm.”

That pulled him out of his post-orgasmic coma a little. “Got to be two months, then.”

“Okay, two then.”

“That was awful easy,” he suspiciously said.

“If you win, I’ll let you fuck my ass.”



“What if you win?”

“What do you think is an even wager?”

His eyes widened and he said, “Oh no.” The previous conversation left little doubt in his mind what her wager was.

She knew that he wanted anal something fierce. He hinted at it all the time. There was a way to sweeten the deal and push him over the edge, though. “What? Are you chicken? Afraid I’ll prove you wrong?”

“Hardly,” he said and then chuckled.

“Then what’s the problem? You can’t lose, right?”

“You have to take the gas can out of your trunk, too.”

“Done. It’s a bet, then?”

“Yeah, it’s a bet.” He gave her an evil grin and added, “Just put the gas can in my trunk. I’ll be needing it soon enough.”

“We’ll just see about that, won’t we?”


Six weeks into the bet, Natalie breathed a sigh of relief as she shut off the sputtering car in front of the gas pump. It was the second such close call, with the first causing her to be late for work because she had to stop on the way in.

No matter, she’d made it. If it hadn’t been for her boss sending her on the lunch run two days in a row, she wouldn’t have even needed to worry about it. Confident that she was going to win the bet, she filled up the car and headed for home. She’d talked with her boyfriend about his qualms a little more — after sex of course — and found out his objection.

Her finger creeped him out because it wasn’t likely to be the culmination of the evening, followed by showering, the way anal sex would. It was the thought of her touching him afterwards that made his skin crawl.

That had given her an idea, and with her victory in sight, she decided to follow up on it.

Back at home, she switched the browser over to private so it wouldn’t record the history. Likewise, when she reached the website, she signed in to her old account from before she and Gene had hooked up. It took a few tries to remember the password, plus a couple of minutes to enter a new credit card number and update her other information, but then she was ready to browse.

She nearly got distracted by a large ad for a rabbit vibe on sale on the front page. She only had a smooth, cheap vibrator, and had always wanted a rabbit. As it was, she and Gene fucked like rabbits, so her vibrator sat in the drawer sans batteries, where it had been for months. That was enough to make her select the category of what she was really looking for.

The most popular items at the top of the first page were all butt plugs, and way more than she was looking for. The sight of one of those would send him running for his life. Even the ‘beginner’ ones looked more intimidating than she thought he could handle.

Finally, she found what she was looking for. It was designed as a prostate massager, and had a vibrator inside with a corded remote control. It wasn’t much bigger than her finger, curved perfectly to go where it was supposed to, and had a T-handle for safety’s sake.

The only problem left was how to get it without him finding out about it.

A quick phone call took care of that snag, and she set the delivery address to her friend Marsha’s apartment. One final click to confirm the shopping cart, and her new toy — or rather, Gene’s — was on the way.

She closed the browser window down just in time, as he walked in the front door. Already wet from thinking about using the toy on him, she decided to offer him ‘desert’ before dinner.

He was happy to indulge.


Natalie couldn’t stop herself from glancing over at her purse, where the new toy waited for her to hide it at home. She’d taken it out of the package, put in the batteries, and given it a good wash at Marsha’s, not wanting to risk taking the time at home.

Tomorrow was her victory day. She’d made it through the two months — actually surprising herself a little — and in just a couple of minutes, she would be leaving the gas station with a full tank, making sure there was no way she could possibly lose.

She didn’t have a couple of minutes.

The car started to sputter and she cursed as she looked at the gas gauge. She hadn’t thought about the trip to Marsha’s, in the complete opposite direction from her path home.

“Come on. Come on,” she pleaded, to no avail. At the last second, she pulled into a parking lot and coasted to a stop no more than three blocks from salvation.

All wasn’t lost, though. Biting her bottom lip, she grabbed her purse and jumped out of the car. Praying that Gene wouldn’t come by on his way home from work, she hurried to the gas station. Thankfully, they sold gas cans.

Eyes darting everywhere like a thief escaping with ill-gotten gains, she headed back to the car with a gallon of gas. The car didn’t want to start, and it only fired up after her third attempt, causing her to let out a weepy sounding sigh of relief. She only truly relaxed when she stopped in front of the gas pump, though. Knowing she couldn’t leave it in the trunk, she put the plastic gas can she’d just purchased down next to the pump and left it there when she drove away.

Her secret safe, she only had to live with her already nagging conscience.

Gene didn’t make that any easier, because he was obviously nervous. Up until a week earlier, he’d made at least one smug remark a day about the law of averages and her track record of running out of gas. Now, he saw the consequences of his bet were coming home to roost, and it had done more than take the swagger out of him. He was truly frightened of losing the bet.

More than once that night, she almost told him the truth.



Two days after winning the bet — at least as far as her boyfriend knew — Natalie had yet to collect. She felt so guilty that she’d made him one of his favorite meals for supper each day, sat with him and watched baseball, even though it bored her to tears, and then did a sexy striptease before climbing into bed with him.

She was up to striptease number two when he said out of the blue, “Okay. You won the bet.”

“Why don’t we just forget about it, baby,” she said as she continued to sway and peel off clothing.

“I’ve never welched on a bet in my life, and I’m not starting now. Let’s just get it over with.”

Natalie sighed, stepped out of her panties, and walked over to sit down on the bed. “That’s not how I want it to be. I want you to enjoy it. I know you will.”

“Don’t see that happening.”

“Let’s just forget it, then.”

“That’s not happening either.”

He was determined, and that made her feel worse than ever. She held up a finger and opened the drawer on her nightstand, digging out the prostate massager.

His eyes went wide and his voice quavered a bit when he asked, “What’s that?”

“It’s a prostate massager. I thought maybe you’d feel better about this than my finger.”

“It looks like a medieval torture device,” he muttered under his breath.

“Just forget about it,” she said and tossed the toy back in her drawer before heading toward the bathroom to try to regain her composure.

She heard the bedsprings creaking and he caught her by the arm before she’d taken more than a step. “Wait, baby. I’m sorry.”

“You don’t want to, and it was a stupid bet.”

“I took it, though. Look, I promise I’ll try to relax.”

“You don’t have to.”

“Okay. Forget the bet. I’ll do it for you.”

The way he said it made her heart soar and her eyes even go a little misty. “You’d do that?”

He tugged her back toward the bed. “Sorry I was being such a jerk. You want to, and I’ll try. Okay?”

“You’re sure?”


Unable to hold back the grin spreading across her face, Natalie retrieved the toy and a bottle of lube. She put them near the foot of the bed, keeping them out of sight behind an artfully constructed wrinkle in the bedclothes, and cat-crawled up to him. She did everything in her power to be as sexy and distracting as possible, and the way his boxers were rising into a tent indicated that it was working.

Crawling over his body, she let her stiff nipples glide along his chest. When she dropped down for a kiss, she swiveled her hips, grinding her pussy against him, not only so he could feel it, but to give her a measure of relief as well.

Their kisses grew more ardent, and his hands roamed over her back in an ever-stronger indication of desire. Natalie pulled away from his lips, offering a sultry smile before planting a kiss on his chest.

Gene groaned as she kissed her way down his chest, letting both her breasts and her hair caress him. When she reached the spot on his tummy where her wetness glistened on his skin, she lapped up every drop while looking up into his eyes.

“Taste good?” he asked.

“Mmm hmm,” she answered, knowing how much it turned him on to see her tasting herself. While licking her lips, she slipped her fingers beneath the waistband of his boxers.

A moan escaped her when she revealed his cock, because it was rock hard and twitching up from his body. She traced a half dozen kisses down its length before pulling his boxers the rest of the way off.

Concealing the action in the process of leaning over his erection, she pulled the toy and lube closer. Again, she kissed his cock, right on the swollen tip, and then gave it a broad-tongued lap, making him groan.

She wetted every last inch of his manhood with her tongue, twice scooping up drops of pre-cum with just the tip as he moaned and groaned encouragement. He stiffened a little when she pushed up on one knee, apparently anticipating where it was going to lead, but relaxed again when the tip of her tongue flicked all over his smooth-shaven balls.

Keeping her tongue moving, she opened the bottle of lube as quietly as possible, squeezing out droplets onto the toy. She smeared it liberally over the shaft, and then held it upright by the T-handle while she moved to stronger licks that rolled his balls with just the amount of pressure she knew he loved.

Once again, he stiffened when she squeezed out a dollop of lube onto his puckered hole.

“Just relax, baby,” she cooed, and then wrapped her lips around the head of his cock.

Knowing there wasn’t much more she could do to ease his nerves, she pressed the tip of the toy against him while massaging his cockhead with her lips and tracing the ridge with her tongue. He was completely puckered up, of course.

Natalie had been practicing something with her vibrator for a while, but hadn’t yet felt brave enough to try it for real. Bracing herself, she quickly slid her lips down over his cock. A croak escaped her when the head invaded her throat, but she kept her gag reflex under control. Gene let out an explosive grunt as her eyes watered, and the surprise of her deep-throating him for the first time did the trick.

He gasped as she pushed the toy into his ass.

Trailing thick strands of saliva, she slid her lips back up his shaft and coughed. She only paused long enough to take a deep breath before swallowing him again, though.

“Fuck, baby,” Gene exclaimed, his voice a mixture of panic and wonder.

A brief coughing fit shook her when she released him this time, but she didn’t let it stop her from tickling the head of his cock with her tongue. Once she caught her breath, she started sucking him in earnest, and gave the slider on the remote a little nudge.

Gene growled as the toy came to life in his ass, and he throbbed in her mouth, pressing hard against her tongue. She sucked about half his length with a rapid bobbing of her head, her cheeks concave around him.

To her delight, he spit out, “Turn it up,” amidst surprised sounding grunts.

“Mmm hmm,” she moaned around him while turning the power of the toy up to about half. Her pussy tingled as a fresh rush of wetness flooded it, brought on by his reaction.

Gene panted, his breaths interrupted by grunts and growls. She sucked him hard and fast, her eyes widening when she saw his hands clenching the sheets and the muscles in his chest tightening. She knew him well enough to read the signs of his body. He was on the cusp of an eruption.

A quick flick of her finger turned the toy up to full blast.

The sound of his panting suddenly ceased, and he went stiff as a statue. Natalie slid her lips back up to the tip just as he lurched and roared.

It felt like someone had unleashed a super-soaker into her mouth. She had never in her life felt a man coming so hard. A staccato series of grunts burst from his lips as he squirted again and again, filling her mouth with hot cum. She sucked and swallowed, draining him dry, her skin breaking out into goose bumps from the intensity of it all.

When his grunts turned high-pitched and pained, she quickly flicked the slider on the toy to off and pulled it free of his ass. A quavering growl accompanied a final lurch from Gene before he went limp, breathing hard. She let him slip from her lips and marveled at the sight of him gasping for breath, his face bright red.

Reclining next to him, she ran her finger over his rapidly rising and falling chest. “That wasn’t so bad, was it?”

He gasped and responded with a weary, “Fuck…”

“I told you, didn’t I?”

“Never come that hard,” he mumbled.

She giggled and said, “I noticed.”

Even though she was aching to be touched, Natalie slipped out of the bed and strutted out of the room. She returned with two bottles of water, one of which he accepted with a grateful nod.

Gene caught his breath after a few minutes and brushed his fingertip through the tiny strip of hair she left unshaven on her mound. “I don’t know whether I lost that bet or not.”

Though she masked it in a whimper as his finger moved lower, what he said caused her guilt to come surging back. She knew there was only one way to make amends.

“Why don’t we pretend you didn’t lose?”

His eyes lit up and he smiled. “Yeah?”


Natalie rose up to her knees and straddled him, wiggling her ass in front of him as she bent down over his cock. She gave it a lick and asked, “Do you want to fuck my ass?”

“Fuck yes.” He gave her buttocks a squeeze before sliding two fingers into her wet heat.

Another lick and a kiss on his cock caused it to twitch. “You want to fuck my ass and come inside it?”

“Ah yeah, baby.”

“Then make it hard for me. I want it. I want your cock deep in my ass.”

Gene’s fingers stroked in and out of her, making her moan as she tongued him.

“Do it. Make it hard. I want it in my tight little ass,” she pleaded between licks, beginning to feel as excited as she was trying to sound. Despite how rough the last man to take her there had been, she remembered the fullness, like nothing she’d ever felt before. She knew Gene wouldn’t ravage her that way.

By the time he started to swell beneath her tongue, she was positively dripping between the anticipation and his fingers stroking her need.

“Baby, put it back in.”

Natalie gasped and a shiver rippled through her. “Oh, god yeah,” she breathed as she reached for the toy and lube. Breathing fast from the excitement, she dribbled a little more lube onto the toy while he bent his knees.

There was barely any resistance as she pushed it into his ass, and his cock started a rapid rise the moment it was inside him.

After a few more licks and a long, slow suck, she turned around and reached into her nightstand drawer. She put batteries into her vibrator in record time as Gene scooted over to the side of the bed and sat up, his cock rock hard and a loop of the control cord for the toy peeking out from beneath his balls. He reached for the lube and she couldn’t hold back a whimper.

Natalie lay down on her back, pulling her knees up and out as she watched him slather lube over his cock. She turned on her vibrator and rubbed it over her folds, whimpering despite an instinctual puckering of her back door. He knee-walked to her, lube in hand, and she let the vibrator drop to the bed while leaning back. Fingers gripping her buttocks, she tugged them apart, and he tipped the bottle of lube.

She gasped when the chilly liquid drizzled onto the iris of her ass. After a couple of deep breaths, she said, “I want it.”

Gene tossed the lube down to the bed and moved into position between her legs. She moaned when he reeled in the cord of the toy and turned it on, a shiver shaking him as it came to life. She picked up her vibrator and centered it over her clit as the head of his cock pressed against her back door.

He pushed, and she groaned. Her eyes shot wide open and the groan turned into a squeak when the head popped inside her ass.

“So fucking tight, baby.”

“Go easy, please.”

He rocked his hips, not really stroking his cock, but rather stirring it inside her. Heart beating a rapid tattoo in her chest, she fought to relax against the invader stretching her ass. She rubbed her vibrator up and down her nether lips and let out a squeal when another inch of his cock penetrated her.


“Uh huh,” she answered.

He gave her another inch, and the growl Natalie let out was so deep and animalistic that it shocked her. The slight burn, urge to push, and incredible feeling of fullness was building a chilly tingle beneath her mound despite barely using her vibrator.

He pulled back, and she whimpered. “More lube.”

Gene’s cock popping out of her ass made her suck in a sharp gasp. A second followed when the cool lube hit her hot ass and seeped inside. His cock stretched her again a moment later, pushing even deeper, and she peeked up over her breasts to see half of his erection buried in her back door.

He stroked his cock slowly in and out, and she groaned with every penetration. Her ass was so full, but it was matched by an aching void elsewhere. Her vibrator took care of that as she plunged it to the hilt in her pussy.

“Yeah, baby,” he grunted as he picked up the pace a little.

Natalie fucked herself with her toy at a far quicker pace than her boyfriend was taking her ass. Stuffed from both the front and back, she pinched her eyes closed while her mouth dropped open. In that moment, she surrendered to him, and his balls settled against her.

“That feels so good,” Gene growled as he pulled back to thrust again.

“Oh yes, so full.”

Though he kept the pace moderate, he was truly fucking her ass after that. She stopped paying attention to her own animalistic cries, which accompanied every thrust of his cock, focusing on keeping her vibrator pumping into her depths. Her breasts quivered as he built up to speed.

She could feel faint hints of the vibration from the toy in his ass transferring to hers when he cranked up the power to the max. Now open to him, accepting the invader plundering her forbidden canal, she soared rapidly toward a climax.

“You gonna come, baby?”

“Uh huh. Uh huh.”

“Oh yeah. Do it.”

As if she had any choice.

For a few strokes, she teetered on the cusp of oblivion. Her bottom burned. Her vision dimmed. Her clit throbbed. Once, twice, and a third time, she cried out as his cock vanished into her depths, balls slapping against her skin. On the next thrust, she jammed her vibrator in so deep that the tips of her fingers penetrated as well. With the toy knocking at the entrance of her womb, her body finally gave her release.

“You coming?” he asked over her yelps of ecstasy.


“Fuck. So close.”

“G-give it t-to meee!” she cried out, her voice rising into a scream as an even more powerful wave of orgasmic energy swept through her.

“Gonna come in your ass, baby.”


He roared again, jolting her on the bed with the power of his final thrust. The sensitive nerves in her ass let her feel every single spurt erupting from him, pooling around his cock, so hot and deep inside her. Her orgasm went on and on as her body tried to thrash and flail while pinned down by his hard cock pulsing in her ass. All the while, Gene growled, his manhood still pumping even after the well of cum was dry.

Her vision went dark when he jerked free, unable to endure the vice-like squeeze of her ass any longer. She could feel cool air rushing inside her and hot cum dribbling out. Another wave of beautiful agony squirted her toy from inside her, and it rolled under her butt as her legs fell back to the bed.

Utterly spent, neither of them could do more than gasp for breath and quiver for long, long minutes afterward.


Natalie gingerly stepped out of the shower on legs weak from coming on his tongue beneath the warm spray of water. She leaned over the sink, resting her head on the cool counter.

“Okay?” he asked, caressing her bottom.

“My butt hurts, but…” She let out a long, deep moan. “So worth it.”

He leaned over her and kissed the back of her neck, making her quiver, and then said, “I’m glad I lost this bet.”

Natalie grinned, knowing that wasn’t exactly true, but she kept it to herself. “I think we both won this one.”

She stood up straight, turned around, and sought out his lips. When they broke from the kiss, she let a coquettish grin creep across her face.

“Bet I can get you hard again tonight.”

“You’re on.”

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