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You Bet Your Ass
My girlfriend and I have a little game – it’s called You Bet Your Ass.
It started off innocently - a gambling competition, betting on the outcome of sporting events or things like that. The winner proudly declared ‘your ass is mine!’ and then got to reap the rewards by getting the loser to do the washing up, fetch the dry cleaning or suffer some other mundane punishment.
But last week, when I was feeling especially horny, the competition took a turn to the literal. We took a bet and she asked: “Will it be washing your car? Or doing the vacuuming? What do you want if you win this round of You Bet Your Ass?”
“Exactly that,” I grinned wickedly. “Your ass.”
My girlfriend has a gorgeous, round bottom. Ever since I’d first met her, I’d had fantasies of trying anal sex with her.
Perhaps it was the glass of wine she’d had. Maybe she was just sure her team would win. Whatever the reason, she agreed.
And that’s how, that same evening, my girlfriend found herself naked on the bed, her face buried in the pillows and her big, round, beautiful bottom poking up into the air.
“You Bet Your Ass,” I gloated, “and you lost.”
“Damn the Red Sox,” she pleaded wantonly, adding: ‘Please be gentle.”
I rubbed her bare back comfortingly.
“I promise.” Secretly, I suspected she wanted this as much as I did.
As she lay there on her knees, I knelt behind my girlfriend, peering at the beauty of her brown thighs and round buttocks. Peeking from between them were the pink lips of her shaven pussy. She smelt delicious – she’d just taken a long, hot shower and powdered her thighs and privates with fruit scented Sensual Body Powder.
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Cupping one of her buttocks in each hand, I spread them apart and gave a long, languid lick up the cleft of her cunt. Her glistening pussy opened like a flower and I heard her moan into the pillows. Encouraged, I licked again.
She was clean and hairless and the mixture of her arousal and the scented powder soon had me feasting on her – my tongue lapping hungrily at her clit, while my hands dug into the soft flesh of her backside. She pushed her butt back into my face, murmuring into the pillows and gripping the sheets tightly in her fists.
I stopped licking before she came, reaching behind me for our box of sex toys and finding her little jelly Vivid Bunny. I turned the vibrator on and pressed the quivering ears against her clit, while the Bunny’s pliable body hummed deliciously between the moist folds of her pussy.
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“Here,” my fingers curled around one of her wrists. I pulled her hand between her thighs and pressed her palm over the humming Bunny. “Hold that there.”
She made an affirmative sounding groan.
While the jelly rabbit carried on what my tongue had started, I reached again into the box of goodies and produced a foil packet, which I quickly tore open. Out I pulled a slick sheet of latex – a Sheer Glyde Dental Dam.
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Although my girlfriend was clean and freshly showered, I knew she was self conscious about anybody touching the ‘dirty’ part of her body – so I spread her buttocks and gently pressed the slick latex between them – over the clenched brown button of her asshole. The latex clung perfectly to her skin.
I spread her buttocks and lowered my face between them. A moment later, I heard a muffled yelp as she felt my rough tongue slurp across her anus.
While the bunny buzzed on her clit, I licked and kissed her tight little butt. The Sheer Glyde latex was thin enough for every sensation to be transmitted to her quivering anus, while the cherry taste was sweet enough to keep me slurping hungrily.
My girlfriend groaned into the pillows. I felt her thrust her hips back, pressing her ass against my face as I licked. I could tell from her shuddering thighs and clenching buttocks that she was a hair’s breadth from orgasm.
I reached down and pressed her palm harder against her body, pinning the buzzing Bunny against her clit. At the same time, I narrowed my tongue into a point the thrust it between her buttocks. Her anus opened up obediently.
She came.
Crying into the pillow, her whole body shuddered as her orgasm washed over her.
I held the vibrating Bunny hard against her until the shuddering finally ceased. Drained, my girlfriend flopped to her side, her face sweaty and her chest heaving.
“Oh, wow…” She moaned.
Leaving her to catch her breath, I gently peeled the latex from between her buttocks and threw it aside. I gave her buttocks an affectionate smack. She giggled playfully.
“We’re not done yet,” I warned her, indicating my throbbing erection. “I still have your debt to collect on.”
My girlfriend’s eyes widened as she saw how hard I was.
“It’ll never fit!”
But her protests were uncommitted – and she didn’t object when I rolled her onto her tummy and pulled her legs off the bed. Her knees met the floor – she was bent over the edge of the bed, her pussy and ass proudly on display.
I reached once again for the box of sex toys and dug out an aerosol can.
The can hissed. My girlfriend jumped as she felt cold wetness spray between her buttocks.
“What the hell is that?” She cried. “Pam?”
“It’s lube,” I said soothingly, rubbing her broad back to calm her.
I’d used Mr Ease Anal Spray, which apparently contained herbs that helped relax the sphincter and make anal penetration easier.
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To test that theory, I parted her slick buttocks and pressed the tip of my little finger against her wrinkled, brown anus. The slick lube helped my finger pop past her tight little bum’s resistance and my finger sunk effortlessly in up to the second knuckle.
“Oooo,” she wiggled her rump. “That feels weird…”
I fucked her gently with my little finger, getting her used to the size and the sensation of being penetrated. Meanwhile, with my other hand, I scrabbled around for a bottle of Anal Lube. When it came to anal sex – especially with my girlfriend’s virgin bottom – I adhered to the principle of ‘too much lube is almost enough.’
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“Brr!” She shivered as I squirted a big dollop between her buttocks. “That’s cold!”
It didn’t stay cold for much longer. Now my fingers were slick and greasy, I gently pressed a second finger into her buttocks. She squirmed, but her slick anus opened up obediently.
“Mmmmm,” her head dropped to the covers. I saw her bite a fold of the sheets.
With my free hand, I slathered by throbbing erection with anal lube. It glistened wetly, the veins and head distended.
“Permission to come aboard, Cap’n!” I asked, raising myself up and crouching between her spread thighs.
My girlfriend groaned.
“What if I don’t give you permission to ‘come aboard?’”
“Well,” I grinned, grabbing my cock like it was the handle of a baseball bat. “I guess that would make me a ‘Butt Pirate.’”
She giggled.
“Yaaaar!” I roared, as I wrestled to press the swollen head of my cock against her delicate brown anus.
She squeaked as she felt the pressure – but the lashings of lube and my two fingers had opened and slathered her bum. With just the slightest thrust of my hips, I felt her sphincter bulge and the head of my cock ‘popped’ past the ring of resistance.
“Uuuuuuh,” she shuddered, balling up fistfuls of the sheet. “Oh my goodness!”
Inexorably, inch after inch of my erection sunk between her buttocks, until my pubic hair tickled her bottom and my balls slapped wetly against her pussy.
“Are… are you in?” Her voice was quivering.
“I’m in,” I promised.
Reaching across the bed, I recovered her Vivid Bunny and pressed it into her palm. Gently, trying not to dislodge the big intruder buried in her rump, my girlfriend slid her hand between her tummy and the bed, down between her thighs.
She pressed the bunny against her clit. I heard the vibrations start.
“Uuuuh,” she sighed. Then she whimpered, in discomfort and pleasure, as I slowly began to thrust.
The velvety caress of her tight, quivering ass was delicious. I wanted nothing more than to pound her roughly – but I knew I’d hurt her if I did that. So I took it painstakingly slowly, easing in and out, feeling the tight ring of her sphincter clutch my hardness.
“Ooooh.” Slowly, as the buzzing on her clit increased her arousal, my girlfriend thrust back. “Mmmmm.”
She controlled the depth and speed, grinding and thrusting her backside into my hips – slowly impaling herself on my erection, then backing off, feeling her insides empty.
Her thrusting got faster. The slap of her sweaty buttocks meeting my hips echoed across the room.
“Ugh, ugh, ugh,” she was grunting rhythmically. “Fuck me,” she demanded.
So I did, slamming back to meet the movements of her hips.
It felt wicked and shameful – and I loved it. My girlfriend had been transformed from a quivering, uncertain anal virgin to an enthusiastic slut who was eagerly skewering herself on my erection.
“Oh God, Baby,” she groaned. “I’m going to come.”
And she did.
The feel of her shuddering hips and the contraction of her tight little bottom tipped me over the edge as well. Buried deep inside her, I felt my cock bulge and spurt. I came inside her, exploding like a liquid cannonade.
Eventually, as we both spiraled down, back into reality, my flaccid cock popped from her backside.
She dragged herself onto the bed. I lay down beside her, spooning her sweaty, slick body.
“Mmmm,” my girlfriend nuzzled against me. “That was wild… And I can’t wait.”
“Can’t wait for what?” I asked her, stroking her tummy.
“Until the next round of You Bet Your Ass.” She rolled over and reached to clasp one of my buttocks. She squeezed, hard. “Next time, I fancy being the one who wins.”
But that’s a different story…