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My First Time Getting Fucked In The Ass.

"It was a pain in my ass, but well worth it!!"

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It was a Saturday afternoon, sometime around three. The house was quiet in that eerie way it only gets when you know no one’s coming home for a while. My parents had left the night before on some weekend getaway. I had the whole place to myself until Sunday night. I knew exactly what I wanted to do with that time.

We’d been talking about it for a couple weeks. Just over text, never in person. I think we were both afraid to say it out loud. But I’d told him I was curious, and he told me he’d done it once before. And now that I had the chance, the privacy, and the nerve — I wanted to try it.

I was already dressed for him: my red booty shorts clinging to my ass, a loose tank top, and underneath, a matching black bra and thong. My pussy smooth and bare, and my skin had that soft, warm, almost glowing tan from spending most of the summer in my bikini.

I checked myself in the mirror — hair okay, makeup on point, lip gloss — and walked back into my room. It was made up fresh. Sheets straightened. Towels nearby, just in case. Lube in the drawer, unopened but ready. My hands were cold even though I was sweating.

The knock at the front door made me jump. I let him in and locked it behind us.

He was a couple of years older than me. We’d fooled around before — mostly blowjobs, fucked a couple of times — but nothing serious. Just fun. But this was different. We were going to cross a new and different line.

We walked into my bedroom like we were sneaking into a hotel room. I sat on the edge of the bed, and he stood near the door, looking unsure of what to say.

“You sure?” he finally asked.

I nodded. “Yeah… just nervous.”

He smiled, stepped closer. “We’ll go slow.”

He leaned down and kissed me, soft at first, then deeper. My stomach fluttered. The nerves didn’t go away, but kissing made it easier. His hands slid down my sides and under my shirt, cupping my tits through my bra. I exhaled shakily as he tugged the tank top up and over my head. He unhooked the bra next, and my nipples were hard as could be.

I reached down and unbuttoned his jeans, pulling them open. His cock was already hard under his briefs, and I felt my breath catch as I brushed my fingers over it. He pulled off his shirt, then dropped his pants and boxers in one motion.

I stood and turned around, letting him pull my shorts and thong down. He knelt behind me, hands spreading my cheeks a little, just looking.

“Goddamn,” he said. “You’ve got a perfect little ass.”

I bit my lip, too shy to answer. I climbed onto the bed and got on all fours, my chest low, knees wide. I was already trembling.

I heard the lube bottle crack open.

The cold gel made me gasp when he spread it over my asshole. His fingers rubbed it around the tight ring, gently working it in.

“You okay?” he asked.

“Yeah. Just go slow…”

His fingertip pressed in — not even the tip of his cock yet — and I flinched. It wasn’t pain exactly, but a burn, a pressure that made me instantly tense. He waited, then tried again, rubbing in small circles.

After a minute or two, he pulled his hand away, wiped it on a towel, and moved behind me. His cockhead pressed softly against my hole. I reached back, bracing myself.

“Just breathe,” he said.

I nodded. Then he pushed.

I gasped — not from pleasure. It hurt. A deep, sudden sting, like I was being split open. My eyes watered, and my hands gripped the blanket.

“Fuck,” I hissed. “Wait…”

He stopped immediately, just the tip inside. The burn was sharp, unforgiving. I breathed through it, face buried in the bed.

“You okay?”

I nodded, still panting. “Just… hurts more than I thought…”

“I’ll go slow. Promise.”

He didn’t pull out — just held still, one hand rubbing my back gently while the other steadied himself at my hip. The moment stretched out. I kept breathing, letting my muscles adjust, letting the sting dull to a pressure. After a while, I felt something give.

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“Okay,” I whispered.

He started moving again, inching deeper. Every bit stretched me more than I thought possible. I groaned low, body trembling. My ass felt impossibly tight around him, clamping down. I couldn’t believe how thick he felt. How full.

“You’re doing so fucking good,” he said under his breath. “Jesus, you’re tight.”

His cock slid in a little further, then a little more. I cried out softly, the ache deep and spreading. I could feel everything — the shape, the stretch, the slow glide inside me. I was fully, utterly opened up for him.

I didn’t say much. I couldn’t. All I could do was breathe and moan.

Eventually, I felt him bottom out — balls resting against my ass. He held still, panting.

“You okay?” he whispered again.

I nodded, shocked at myself. “Yeah… I can’t believe I’m doing this.”

He slowly pulled back and pushed in again. The movement made me shiver. It hurt, but it was starting to feel good in a way I didn’t expect. Intense. Dirty. Wrong and right at the same time.

“Fuck,” he muttered. “Your ass is unreal.”

He started fucking me — slow, steady strokes. I moaned into the sheets, clenching my fists, letting it happen. Every thrust pushed me forward. My hips ached, my thighs trembled. I could feel lube and slickness gathering around his cock, some of it leaking down my crack.

He got rougher. His hands dug into my hips, pulling me back onto him. I was panting, moaning louder, the pain dulled to a deep fullness that made me dizzy.

“I’m gonna cum,” he said suddenly, breathless.

I nodded without turning around. “Do it…”

A few more hard thrusts, then he groaned, buried himself deep, and pulsed inside me. I felt it flood in — warm, thick, unmistakable. My whole body clenched, feeling every twitch, every drop. It was filthy and perfect.

He pulled out slowly, and I whimpered. I felt it instantly — his cum leaking out of me, down my thighs, onto the bed.

He wiped me gently with a towel, not saying much, then lay beside me for a minute, breathing hard.

Neither of us moved for a while. My ass felt raw, sore, and stretched. I stayed on my stomach, letting the feeling sink in.

He got hard again surprisingly fast.

“You okay if we go again?” he asked.

I turned my head, lips parted. “Yeah… just go slower this time.”

Round two was different. Less pain. More glide. My body was looser now, wetter, more used to him. He slid in more easily, still making me wince, but I could handle it.

This time he held my hips tighter, fucked me deeper. His rhythm was more confident. I moaned louder, gripped the sheets, and let him use me.

“You’re so fucking good at this,” he whispered. “You like being filled, don’t you?”

I nodded, gasping. “Yes…”

He came again inside me, not even five minutes later. Less this time, but just as deep. I felt it all over again — the warmth, the leak, the ache.

When he pulled out, I collapsed. My body was wrecked. My asshole throbbed with every heartbeat. But I felt high, glowing, proud. I’d taken it. I’d let him use me. And I wanted to do it again sometime.

He got dressed quietly. I went to the bathroom to clean up, walking slowly, cum dripping from between my cheeks. I wiped, washed, and stared at myself in the mirror — naked, flushed, wrecked.

When I came back out, he was lacing his shoes.

“You okay?” he asked.

“Yeah,” I said, voice soft. “Just sore.”

He gave me a crooked smile. “You took it like a pro.”

I didn’t know what to say, so I just smiled back.

After he left, I lay on my stomach in bed, feeling the weight of it all settle in — the mess, the stretch, the ache. I didn’t cum. But I didn’t care.

Because that day, I gave him something no one else ever had.

And I wanted to feel that again.

Published 
Written by SinfullSydney
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