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.

An hour later the bottle was lower and we were all on the couch somehow, Fiona in the middle at first, then sliding so Yvonne ended up half in my lap when she leaned in to whisper something about how warm my place felt. Her ass settled against my leg. I could feel the heat of her through the thin fabric. Fiona’s hand found my knee and squeezed. “I’ve been thinking about this all night,” Fiona said suddenly, looking straight at me, then at Yvonne. Her voice was steady, a little breathless. “Watching you fuck someone else. Not just anyone. Her. And not just regular. I want to see you bury that cock in her ass. I’ve wanted it for months. Every time she comes over in those tight jeans I picture it.”

Yvonne went still. Then she turned her face toward me, lips parted. “I’ve fantasized about you since the first time Fiona brought you around,” she admitted, no teasing now, just raw. “Caught you looking at my ass when you thought no one noticed. I used to touch myself after, imagining you holding me open and pushing in slow, then hard. My ex never got me there. I need it. Please, Sergio. Fuck my ass the way I’ve been craving. Deep. I want Fiona to watch every inch.”

My pulse was hammering in my throat. I looked between them—Fiona’s eyes dark and eager, Yvonne already shifting so she could grind lightly against my thigh, the dress riding higher. “You both sure?” I asked, voice rough. I needed to hear it clear. Fiona nodded hard, hand sliding up to cup me through my pants, feeling how stiff I’d gotten. “I want this. I want to see her take you. I want to hear the sounds she makes when you’re balls-deep in that tight little hole.” Yvonne reached back, guided my hand under the hem of her dress, let my palm settle on the bare cheek of her ass. No panties. Just warm skin and the faint damp heat higher up. She pushed back into my touch. “I’m sure. I’ve been sure since we walked in the door. Fuck me in the ass while she watches. Please.”

We were all breathing harder. I squeezed that perfect ass, felt her shiver, and Fiona leaned in to kiss Yvonne’s neck while her other hand kept stroking me. The agreement settled between us like something electric and irreversible—three people who wanted the exact same filthy thing, no hesitation left. Yvonne’s fingers worked my belt open just enough to free the head of my cock, smearing the wetness already beading there across her thumb. Fiona whispered against her ear, telling her how pretty she’d look stretched around me. I kept my hand moving, thumb brushing the cleft of Yvonne’s ass, pressing lightly against the tight furl I was about to claim, feeling it flutter under the touch. She moaned, low and needy, and ground back harder. The night was only getting started, the three of us tangled on that couch with the bourbon forgotten and every boundary already dissolving, my cock aching to push into the heat she was offering while Fiona’s eyes stayed locked on us, hungry for the show.

I didn’t waste another second. I stood, hauled Yvonne up with me, and spun her so she faced the back of the couch. Fiona was already on her knees on the cushions, yanking that black dress the rest of the way up over Yvonne’s hips until it bunched around her waist. Bare ass, perfect and round, the cleft already glistening where my thumb had been teasing. I dropped behind her, spread those cheeks with both hands, and buried my face between them.