Double Date Detour: Her Best Friend’s Ass

I still get hard just thinking about that night, the way everything shifted from a half-assed double date into something I’d jerked off to for months afterward. I’m Sergio, twenty-eight, and I’d been with Fiona for almost two years by then. She was the kind of girlfriend who laughed loud, drank neat whiskey, and never once pretended she was shy about sex. Her best friend Yvonne had tagged along because her boyfriend flaked last minute—some work emergency that sounded like bullshit even over the phone. Yvonne was twenty-six, all hips and that sharp little smirk, wearing a tight black dress that clung to her like it was painted on. We’d finished dinner at the Italian place downtown, the three of us crammed into one side of the booth, knees brushing, and somehow ended up back at my apartment with a bottle of bourbon and the lights low.

Fiona kicked off her heels and curled up on the couch while I poured. Yvonne stayed standing a minute longer, turning slow in front of the mirror by the door like she wanted us both to look. “God, this dress makes my ass look so fucking tight,” she said, glancing over her shoulder, hands smoothing the fabric down over the curve. “I caught three different guys staring at dinner. Ex never appreciated it. He’d just slap it once and expect me to ride him missionary like that was enough.” She laughed, but there was heat under it. She dropped onto the couch beside Fiona, thighs pressed together, and took the glass I handed her. Our fingers touched. I felt it all the way up my arm.

I sat in the armchair across from them, trying not to adjust myself too obvious. Fiona caught me looking and grinned, that wicked little flash of teeth. “She’s not wrong,” Fiona said, reaching over to pinch Yvonne’s hip through the dress. “Turn around again. Show him.” Yvonne rolled her eyes but stood, spun, and bent just enough that the hem rode up. The lower curve of her ass peeked out, smooth and round, the kind of ass that made you want to spread it open just to see how pink and small the hole looked. She straightened and sat back down, closer to me this time, one knee angled toward mine.

We drank. Conversation got looser. Yvonne kept circling back to it—how her ex had tried anal once, panicked after thirty seconds, and never touched her there again. “I swear I was so wet just from the idea,” she said, voice dropping, fingers tracing the rim of her glass. “I wanted it deep. Like, bent over and taken until I couldn’t think. He treated it like a chore. Waste.” Fiona was watching me the whole time, her foot sliding up my calf under the coffee table. She didn’t say stop. She said, soft, “You should hear how she talks about it when it’s just us girls. Filthy.” Yvonne flushed but didn’t deny it. The air in the room felt thicker. My cock was already half-hard against my thigh, and every time Yvonne shifted and that dress pulled tighter across her ass, it throbbed.