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Erotic Short Stories

Coed Cheerleader recalls first struggling anal

“Raawwwww!” I screamed, primal, violent, frustrated and totally unsatisfied.

Using a dildo in my ass was nothing at all like a nice big cock. My ex was a fucking asshole, and about the only good thing he had going for him was his smooth thick dick. Kyle was a stupid fuck, but he knew how to use my body for pleasure. He knew how to give me pleasure too, even if I didn’t realize it at first.

“Fuck!” I said, climbing naked out of the bathtub. The flopping dildo lay curved in the bottom edge near the drain.

Maybe it was the toilet, or maybe it was that I didn’t have a real dick in my ass. Either way, I couldn’t cum as Kyle had trained me to.

I’d been hammering my ass with the hard plastic for a good thirty minutes and rubbing my clit until I was slick with sweat and slipping on the back of the porcelain. It didn’t work.

“Why?” I stalked out of the bathroom and moved to the bedroom, flopping on my plush cover. The mattress was comfortable, relaxing, and reminded me of the last time Kyle had reamed my ass to my exploding orgasm.

I squirmed in the covers. The softness, the sliding heat from my body, and the easy way I flowed into the seeming silk were in direct contrast to how rough he’d treated my rear end.

There was a nugget of truth in how he’d plugged my ass, a method that I was missing, or some type of slapping need that I couldn’t match. My hand traced the top of my slit, circled my clit, and wet my already pruned finger. My other hand sloped over my butt cheek, fingertips tickling my butthole. I was stretched from the dildo, which was more than Kyle ever did for me.  In moments I was two fingers in, plunging fast and rough pulling on my smooth tight sphincter while pulling my knees into my chest. The tops of my thighs compressed my nipples and balled up like the fetal position one hand reaching around behind and the other pressed between my legs I moaned.

I remembered the first time Kyle drove his thumb up my ass.

We were on my bed, this bed, and I was on all fours, my feet dangling over the edge. His dick always felt so good filling my pussy. I was pressing my palms into the mattress for leverage to rock my hips into his waist. Kyle was a jerk sometimes, but he had a great dick, thick, long enough to hit my G-spot, and best of all knew how to move it.

I had never put something in my asshole before, nothing. I hadn’t even plunged a finger in while in the shower. Not once, not even when I’d seen a porn on Kyle’s computer the first time.

His finger was an invasion I did not welcome, and the moment he rubbed in slow circles around my tightest untouched hole I jumped away.

“Ahhh! What are you doing?!” I shouted twisting to look over my shoulder. I could see his hands on my rump, his thumb disappearing above my pussy.

“Your ass is so fucking sexy, I’m going to put my thumb in your ass.”

“What? No! Don’t!”

He laughed.

“Relax, you’re going to like it.”

“No! I won’t! AHhhhhh!!!!”

Kyle didn’t listen and pushed in past the nail.

“Fuck!” I screamed, thrashing, but letting him impale both my holes. His laughter was cruel and enraging.

“I knew you’d like it. Damn, you’re a good slut. You’re my slut.”

“It hurts! Oh, my god, it feels so wrong! Ungh!”

His cock still moved inside my sweetness, and it felt good, but all I could focus on was his thumb invading my hole.  He moved inside with everything, stuffing me complete, and dominating my center. He was in command of my body no matter what I thought. Every time we had sex he manipulated my erogenous zones beyond what I expected. I felt like he had a secret map to my pleasure and only he could read how to get the climaxing treasure.

“Mmm, ooh, my god. I like it.” I said, minutes later from his thrusting. He worked my butthole almost like he worked his dick; strong, thick, pulsing. At times he yanked, stretching my butthole wider like he was working a rubberband looser for some reason.

I stopped moving and gripped the blankets to brace myself against his splitting thumb. Still, he moved his dick in slow thrusting motions providing pleasure to balance the pain and discomfort he was wreaking on my sphincter. It hurt, and I winced biting my teeth the whole time. Air sucked through what little space was between my overbite, and it sounded like my jaw was wired shut. The whistle of saliva and air billowing through my cheeks filled the room.

It wasn’t until he let my ass rest and withdrew his thumb that I discovered my jaw was sore from clenching the whole time. Kyle wasn’t one to be finished though, and with both hands holding my waist like he was bracing my body with his whole weight he pulled out of my pussy.

I missed his fullness immediately.

“What? Why did you stop?” I said. “Fucking me, I mean.”

“I’m not done,” he said.

“Want me to flip over?” I said, beginning to twist, but my butt was held firm. His hands were hard on my love handles.

“No. Just try and relax,” he said. I could feel the sick smile on his lips, the cruel intent in his eyes, and hear the joy he contained like a muffled cackle.

“Kyle, wait, no! I’m not readeeeeeeeeeeeeee!”  I screeched, a pure note of banshee madness screaming high pitched, wailing, and then cringing so hard I thought my eyes would burst from how tight I slammed lids shut.

Kyle rammed his cock up my ass.

Pain flooded out of my sphincter, lanced like a sharp poker driven through my insides. Burning awfulness quivered around his thick shaft, and impaled, I thrashed on my knees.

As much as I tried to twist, struggle, flail my legs and heave my back he had me pinned. His thick dick would not leave my butt.

“You ass feels so fucking good and tight! It’s so fucking warm! I had no idea how hot like hot your asshole would feel! God, I love it! Your butt is amazing. Haha, you’re fucking taking my fat cock up your ass.”

“Get it out! Oh my god! Kyle! It hurts so fucking much! Please!” I whimpered, each word punctuated by gasping breath and sucking air against the wincing cringing that pinched my face like an old man eating sour candy.

I tried pushing him away, attempting to leverage against his legs, but he swatted my wrists away and they fell to the bed. He had my waist pinned down and I could not escape his rod.

At least he wasn’t fucking me yet. At least it wasn’t moving.

“Kyle, please! It hurts so much. Like you shoved a fucking wrist into my ass! God!” I sucked in breath, struggling to make it less uncomfortable, to make it less painful with every movement I made. His dick was in my butt! “FUCK! KYLE! OUCH! It hurts! AHhhhhhhh!” I cried.

“Your tits look so fucking good slapping around while you squirm. Relax. I told you. You’ll get used to it.”

He rubbed my back and stroked my butt cheeks down my thighs.

“Relax, relax, let it happen.” He pet me like I was a dog, like I was a cat, like I was an animal he was trying to soothe into submission.

I hated him for it, but it worked.

My pain withdrew, slow like throbbing heartbeats pulling away stiffness, like blood cleaning sore muscles from soreness. Yet, his cock remained.  I panted, moaning every quick exhale.

“See,” Kyle said, still petting my skin with his rough hands. “it will start to feel good. You’re going to cum so fucking hard you’ll be begging me to stuff it in your butt in no time.”

“No, I won’t!” I shouted fast between panting moans. Inhale fast, moan. Inhale fast, moan. Over and over. I wanted to murder him when he laughed.

“Yes, you will.” His cock moved, and I screamed in shock, pain. “Touch your pussy.”

“Ahhh!”

“Touch it, and relax.”

I did. Why did I always let him have his way?

Wordless, not speaking, but in constant breathing moaning I fingered my slit, wet my finger with my sweetness and excitement. Every push his cock moved into my butt opened my pussy wide. When he withdrew it squished shut, and I felt it happen around my fingers.

I moved to my clit, and bit my lip, gasping from the pleasure nestled there in response to his butt reaming dick.

Kyle pumped, starting slow and then building over a period of minutes that seemed to last like a lifetime of suffering. Each push lanced pain spreading from my tightest hole around my stomach and over my pussy like a sympathetic response.

He plugged my asshole, crushed me into the bed, and used my unwelcome hole. I screamed, thrashed, wiggled, and moaned.

If I kept my finger blurring over my clit it diminished the discomfort some, but it was more like playing loud music to drown out cacophony; you were getting damaged ears either way. Worse maybe.

The pleasure I worked out on my pussy was enough to endure his butt fucking until he came.

“Yes! FUCKING YES! I’m cumming in your slutty cheerleader ass!!!” Kyle shouted.

It shot inside my hot rectum like splashing warmth flooding my insides and feeling wrong. I could feel his shaft widen with each pumping gush. Kyle let himself go flaccid inside my ass.

“Your butthole grips me so tight. I don’t think it wants me to pull out.”

“Ungh, you fucking asshole. You fucked me up the ass.”  I said, exhausted and craving a glass of water. I’d been shouting for hours it felt like and I struggled to find my breath and find some recovery. I was coated in wet sweat that now that he’d stopped had made me go cold.

“Fucking right. You’re my fucking cheerleader slut. It was fucking awesome. Your ass is so fucking nice to stuff.” He said and slapped my butt.

“Rrraawwwww!” I shouted, coming out of my memory. That had been the first time Kyle burst through my sphincter. That had been the first time I took it up the butt, well before I learned to love the way it felt. Well before my need to have stimulation in my rear and front together tandem merging to explode my body to skin shattering orgasms.

I’d become addicted to the anal pussy play. Yet, I was missing something. I flopped on my belly with my legs split and heels in the air, pinning one arm under my stomach and reaching around back with the other. Maybe I needed it from behind.

Maybe there was truth in the first time I actually came from Kyle’s dick in my ass.

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