A Friendly Bet

bydamonX©

"Tell me."

"No."

I was getting closer.

"Tell me!"

"In my ass! Alright?! Cum in my fucking ass!"

On cue, I unleashed a torrent of hot cum into Jen's asshole. I continued fucking her as I spurted stream after stream into her body. Jen through her head back and moaned loudly as my balls slapped violently into her pussy lips. After I had shot my last drop I continued sliding my dick in and out of her now slippery ass, causing my cum to ooze out from around my shaft and drip down onto my bed. As my dick became too sensitive I pulled it out of Jen's well-fucked asshole with a lewd slurping sound.

Immediately, Jen collapsed to the bad and rolled over on her side, reaching back with a hand to touch her recently abused hole.

"Owww! Fuck that hurt!" She exclaimed, softly rubbing herself.

"You liked it," I said snidely.

"I did not! It was awful!"

"Yeah? Is that why you were telling me how good my cock felt in your ass?"

"Shut up. That was the heat of the moment."

I just laughed.

Jen began to shift uncomfortably, pursing her lips up in a makeshift snear.

"What's wrong?" I asked.

"It feels weird."

"What's that?"

"The cum in my ass. It feels weird."

"Hey! Don't let it drip out all over my bed!" I ordered, half jokingly. "It's your jizz ya know?" she countered before reaching back to stroke her asshole again.

"Fuck it hurts." she complained.

"Aww, poor baby," I teased. "Do you want me to kiss it better?"

"Yes!" she responded, although I could tell she was joking.

"Okay," I said. "Bend over."

"Uh, that's okay," Jen stated deliberately.

"Nope. Bend over. Come on." I said giving her a playful slap on the side of her ass.

"Noooo," she whined, reaching for her panties.

With a lightning quick movement, I snatched her underwear from her grasp, holding them out of her grasp.

"Hey, give those back!"

Jen rose up to her knees and reached out, but I dropped the panties behind my head and grabbed her around the waist, pulling her down to the bed.

Jen giggled and tried to squirm free, but I was too strong for her. Rolling her over, I pinned her face down on the bed. She was laughing, but her voice was muffled by my cum soaked bed sheets. I grabbed one of her arms and pinned it behind her back, completely immobilizing her prone, tanned body underneath me. I took a moment to gaze at her body before dropping my head to her ass. "Hey! What are you doing?" she asked, half giggling.

"I told you." I replied. "I'm going to kiss it better."

With my free hand I pulled one of Jen's ass cheeks to the side, exposing to my view, the tiny asshole that I had just violated. It looked a little red and swollen with a tiny rivulet of cum running from it.

"No!" she squealed. "You can't do that! You can't...Oh....Mmmm."

Jen's voice trailed off as the tip of my tongue flickered across her puckered little pink ring. She stopped resisting but I remained holding on to her arm as I lapped at her asshole.

Jen's cries of protest turned to moans of pleasure as I planted a deep kiss on her butthole, surrounding it with my lips. I let her arm go free and she immediately reached back to grab her ass with both hands, spreading her cheeks wide.

I smiled to myself as I resumed licking. My best friend was fast becoming my own personal anal plaything!

"Oh my god that feels good," she moaned.

I moved up, planting soft kisses up to her tailbone as I gently grazed a finger over her wet little hole, which was slippery with two of my bodily fluids. I pushed the tip of my finger inside her ass as she reached under to slide a finger into her pussy. When she didn't protest, I slipped my finger in farther as her slippery little asshole swallowed me up to the knuckle. I could feel Jen's own fingers through the thin wall separating her pussy and ass.

"I want it again." she moaned. "I want you to fuck my ass again."

"Really," I asked, sliding my finger in and out of her butt on a river of warm cum. "I thought you didn't like it?"

"Just do it. Please! "Fuck my ass! Fuck my dirty little cum filled asshole!"

How could I resist.

Withdrawing my finger, I positioned myself behind Jen once again as she assisted by spreading her ass cheeks wide. I swiped a finger down her crack, collecting as much of my own cum as I could before slathering it all over my cock to use as lubricant. As the tip of my dick touched her sensitive ring, she grabbed me by the shaft and pushed her hips backwards, forcing my dick back inside the tight confines of her delicious asshole.

I was surprised, but pleased with Jen's newfound aggression and scolded myself for not trying anything with her before.

She wiggled her hips as the remainder of my cock slipped easily into her slick little butt hole.

"Mmmm," she moaned. "It feels way better with a little lube."

"Good thing I didn't cum on your face then huh?"

"Yes. I love the feeling of your cum in my ass. I feel so dirty! I feel like a... Like a whore!"

Jen was slowly grinding her ass backwards into me, urging me to fuck her. "Come on! Fuck me. Fuck me hard this time."

"Okay," I said. "You asked for it."

With that I grabbed Jen's hips and slammed myself into her, driving my cock deep into her tight little cum filled asshole.

"Oh fuck!" she squealed.

I smiled to myself as I withdrew only to drive back into her. Each thrust emitted a lewd squelching sound due to the liberal amount of jism I had recently injected into Jen's hole. I looked down and marveled at the sight of my glistening cock sliding in and out of my friend's impossibly tight butt hole. The movement of my dick was forcing some of my cum out of her ass, which squeezed out from around my shaft, dribbled down the back of her thighs and dripped down onto my bed sheets.

"Fuck. Fuck. Fuck." Jen muttered as each thrust of my hips repeatedly buried the length of my cock into her well-fucked asshole.

Driving my hips down hard, I pinned her petite body against the bed, with my cock firmly embedded inside her. Reaching out, I took hold of her arms and held them in place as I slowly gyrated my hips, grinding my dick into her ass. The entire length of my body was pressed against the entire length of her body, the sweat from out skin forming a cohesive seal between us.

As I gyrated my hips, I kissed her ear before whispering to her.

"Do you like it?" I asked. "Do you like my dick in your tight little asshole?"

"Yessss," she gasped. "I love it!"

I smiled to myself as I peeled my body off hers and propped myself up with my arms. Then, withdrawing my hips, I pulled my cock free of the confines of Jen's impossibly tight hole.

"What are you doing?" Jen asked, looking back over her shoulder with a disappointed but confused look on her face.

Without a word I grabbed Jen's petite body and flipped her onto her back. Then, hooking my hands under her legs I pushed her knees up to her head, exposing her ravaged asshole to my view. I smiled as I gazed down at her glistening hole, which was also becoming quite red and swollen.

"Quite looking at it and fuck it!" Jen ordered, grabbing her own ankles.

I snickered and dropped my head down between her legs.

"What the hell are you....ohhhhhhh."

Jen's voice trailed off in a low sexy moan as my tongue touched her abused and stretched asshole. I circled her anus, running my tongue around her rim before sliding it inside.

"Oh my God!" she exclaimed. "That feels so fucking good!"

I pulled my tongue from her ass and quickly replaced it with my dick, which slid easily inside. Jen was holding her own legs by her head, splaying herself wide open for me as I resumed fucking her wonderful little hole.

"You know, I've never done it this way before," I stated, sinking my cock up to my balls in her ass.

"Well, don't I feel special!" Jen blurted back.

I smiled at her sarcasm and started fucking harder than ever before. I soon lost track of time as I concentrated on the feeling of my friend's tight asshole swallowing my cock. Our new position gave Jen the perfect opportunity to play with her clit, and she released her legs to work at a second orgasm.

"Oh fuck I'm going to cum!" she gasped. "Oh fuck! Oh fuck! Oh fuck!"

I could feel myself getting close as well.

"Where do you want me to cum?" I asked, now frantically plowing her poor little asshole.

"Fuck, I don't care!" she yelled. "On my face! Cum all over my fucking face! Cover me in cum! Ass fuck me and then cover me in cum!

Jen's words must have had the same effect on her as they did on me, because soon she was screaming her way through her second anal induced orgasm of the night, as her asshole clenched around my cock.

While she was in the throws of her climax, I yanked my dick from her butt hole and lurched forward in an attempt to get closer to her face.

"Yes! Yes! Yes! Yes!" she howled as the hot cum fired from my dick onto her pretty face, splattering her lips and chin, and dripping into her mouth.

I collapsed back onto the bed as Jen lay there panting. It took a few moments for both of us to regain our composure, and a few more for either of us to speak.

"Well?" she asked. "Was that dirty enough for you?"

I laughed.

"How about double or nothing?"

Jen scoffed and reached down to gently stroke her severely abused asshole.

"I think I need a few days to recover," she answered.

I just laid back and smiled. I knew that things would never be the same.

And I liked it.

The End

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by Anonymous

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by Anonymous10/19/14

reminds me of my older neighbor

she introduced me to anal sex. she couldn't get enuf. loved it more than vaginal. she was 46 i was 18. wanted me to fuck her every day. i did, for a while, then went away to school. fucked her every timemore...

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