I assfucked my boss’ wife

May Hemm
14 min readMay 17, 2022

Ryan teaches Milena the joys of anal sex, right before she leaves for good.

“What? You mean anal sex?” Milena asked, perplexed. “I have never done that. Even with my husband.”

“Is that a no, then?”

I was desperate to fuck her asshole. That would be a feather in my cap. The chances are slim, though. Especially if she hasn’t tried it before, and I wasn’t exactly the smallest guy around.

I rubbed her thighs, slowly moving my palms over her buttocks. “It’s your choice. I’d like to try it, but I won’t press the issue. I can promise I won’t rush it.”

Milena bit her lower lip. She looked fucking cute when she did that. “Will it hurt?”

“I’m not sure. It will be a little uncomfortable.”

She thought about it for a moment, then her eyes gazed at my cock. “Okay, but can we work our way up to it?”

“Of course,” I said, smiling and trying my best to contain the joy inside me. “I have an idea.”

She looked at me, confused, but let me move her on all fours again.

“Okay, first of all, you need to learn to relax. The more self-conscious you feel, the harder it’ll be. I want you to show me your asshole.”

“What?” she said, eyes going wide.

“Trust me.”

I kept smiling at her and she thought about it before she sighed.

“Okay, but this is so embarrassing.”

I tried to look reassuring, non-judgmental even as her cheeks burned red.

Milena slowly turned, placed her head on the bed while sticking her ass up as me.

I licked my lips, grabbing her buttocks and slowly spread them. “Jesus christ,” I groaned.

“Its ugly.”

I stared, mesmerisingly, at her cute puckered hole. So small and deliciously tight. My cock throbbed to life at the thought of easing into it.

“I can feel you staring,” she whined.

“I’m sorry. It’s just… It’s so pretty. It just makes me want to worship your ass.”

“You’re a strange man, Ryan,” Milena laughed nervously.

May Hemm

Hotwife, cheating and cuckold confessions. I turn them into erotica for all to enjoy.