#EroticJournalChallenge First Time…

Richard’s Anal Story Part 2

I reached down, sliding my hands under her ass and squeezing it. “Need any lube first?”

She shook her head, “With how wet I am, it’s sure to be coated, and your cock is soaked. Just bend me over and make me your bitch.”

I slid a finger between her cheeks and pressed it against her hole. Sure enough, it slid in fairly easily, drawing a moan and some more wriggling from her. I finger fucked it for a bit, timing my thrusts at both ends. If I got the angle just right, I could feel the pressure from my finger on my cock.

Finally, I pulled out and rolled her over. She immediately looked over her shoulder, wriggled her ass, and mouthed, “Fuck me.”

Not wanting to be too easy, I spanked her a few times. After each strike, she pressed her ass back, presenting it to me, along with the growing collection of pink and red marks on her pale skin. Once I’d had enough, I pulled her cheeks open and looked at her hole. It was totally coated in her juices, and with the ones dripping off my cock, I felt pretty sure I’d be able to make it fit. I took my cock in one hand, put the other on the back of her neck, and pushed forward, moaning as she swallowed my cock with ease. I’d never felt such a tight, warm, hole before. Often, anal can be pretty rough going at first, or need extra lube, but her ass took me as easily as any pussy I’d ever been in.

She moaned out and shifted her hips, trying to find the right angle. I pulled back out, shifting my hips a little before driving back in. After a few strokes she had my full length deep in her bowels, and I leaned down to whisper in her ear. “How’s it feel, slut?”

“Hurts,” she moaned.

“Want me to stop?” It was my first time with her after all, I wouldn’t want to be too cruel.

“It’s fine. Fuck me how you want to.”

I pulled back again and shoved into her, pressing her body down. She cried out, gripping the sheets hard as I started to find a rhythm. With every thrust, her body dipped lower, and for longer. After a half dozen or so, she was pinned down on the bed, head whipping back and forth. “Oh fuck! It hurts, fuck fuck fuck!”

I grabbed onto her hips, holding her steady as she squirmed, and took a deep thrust to bottom out in her as far as I could.

“So how do you like anal now?” I asked her, holding myself deep for a few seconds.

“I fucking love it,” she moaned. “Most guys ease off if you tell them it hurts, but not you. You know how to use me.”

I laughed and slid all but the head out of her ass, then rammed back down on her. “Like that?” I growled.

“Yes!” she screamed. “Just like that. Use me, hurt me, rape my fucking ass hole!”

I started building a rhythm, hammering in and out of her as fast as I could as she wailed underneath me. “Anyone ever fuck you like this before?” I asked.

“Oh my god, oh fuck! Once at a party. He came way too fast though. Like he was just trying to tease me. Are you close?” she asked.

“I can keep it up,” I said, swirling my hips a little to stretch her even wider.

“Fuck! You’re so fucking big! Too big for my ass. It hurts so bad, I fucking love it!”

I put one hand in her hair, and squeezed the back of her throat with the other, getting the leverage to really punish her hole.

Every one of my moans was met by a scream from her, punctuated with an occasional whimper. Every once in a while she’d work up enough air for a “Fuck me! Fuck me! Harder! Hurt me!” before a particularly rough thrust would drive it all out with a scream.

“Where do you want my cum, slut?” I asked.

“As deep in my ass as you can. I want to feel it dripping out the whole way home.”

I crushed her down as hard as I could, her moans swallowed up by the mattress for a moment as waves of pleasure crashed over me, pulse after pulse of hot cum flooding into her hole.

Eventually, I let up enough for her to lift her head up, gasping for air. I slowly slid out. “Going to clean me up too, slut?” I asked.

She grimaced, but rolled over, sliding her tongue over my cock again. “Sorry, Sir. That might be too disgusting, even for me.”

I grabbed a fistful of her hair. She yelped, but grinned when she saw me pull my hand towards my cock, wiping myself off with her. “So fucking nasty. I love it,” she said.

And that’s the story of the first time I really enjoyed anal. Nothing like a sub begging you to hurt them while you fuck them, or telling you that you’re the only one who knows how to do it properly.


We’ll see you on Monday, with the next set in our 30 Days of Dominance and submission challenge.

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