It’s not always all work no play

I stepped out of the conference center in downtown Chicago, the weight of a long day of meetings lifting as the cool evening air hit my face. At 51, business trips like this were routine, but tonight felt different—charged with possibility.

I decided to grab a drink at the hotel bar across the street, a sleek spot buzzing with energy. That’s when I spotted them: a boisterous group of women spilling out of a limo, laughing and cheering like they’d just won the lottery.

There had to be at least a dozen of them, ages spanning from fresh-faced 21-year-olds in tight mini-dresses to elegant grandmothers in their 70s with silver hair and mischievous smiles. It was a multi-generational girls’ night out—mothers, daughters, grandmothers, aunts, and a few friends thrown in for good measure. I overheard snippets: “Grandma, you’re wilder than me!” from a bubbly 25-year-old to her 68-year-old matriarch, who winked and adjusted her pearl necklace. I couldn’t resist. As they crowded the bar, ordering rounds of cosmos and tequila shots, I sidled up and offered to buy the next one. “Ladies, you look like you’re celebrating something big. Mind if a weary traveler joins the fun?” They turned as one, sizing me up with appraising eyes.

The leader, a curvaceous 45-year-old mom named Lisa with fiery red hair, grinned. “Only if you can keep up, handsome.” Her daughter, Emily, a 22-year-old blonde with perky tits straining against her top, giggled and nudged her grandma, Margaret, who at 70 still had a killer figure and a twinkle in her eye that promised trouble. We chatted effortlessly—me sharing war stories from the road, them spilling about their annual family getaway turned wild night. Bonds formed quickly over laughter and liquor. There was Sarah, 30, Lisa’s sister, with her own daughter Mia at 21, all hips and attitude.

Then the unrelated friends: Tanya, a 35-year-old divorcee with a penchant for dirty jokes; Vanessa, 50, voluptuous and confident; and a few more scattered across the age spectrum, each adding their flavor to the mix. As the bar closed, Lisa leaned in close, her breath hot on my ear. “Our suite’s upstairs. Why don’t you come up for a nightcap? The girls and I could use some… male perspective.” The group erupted in cheers, pulling me along in a whirlwind of perfume and soft touches.

My heart raced— this was every fantasy rolled into one. We piled into the elevator, hands already wandering. Emily pressed against me, her young ass grinding subtly as Margaret whispered, “I’ve got tricks these young ones haven’t learned yet.” The suite was massive: king beds, a jacuzzi, and a minibar stocked for sin. Clothes started shedding before the door clicked shut. Lisa stripped first, revealing lacy black lingerie that hugged her MILF curves. “Girls, let’s show our guest some hospitality.” It escalated fast. They surrounded me on the bed, a sea of naked bodies—firm young breasts, soft mature bellies, shaved pussies and bushy ones alike. I was their plaything, and they mine.

Emily straddled my face, her sweet 22-year-old cunt dripping as I tongued her deeply, lapping at her folds while she moaned, “Oh fuck, yes, lick me like that.” Her mom, Lisa, watched with pride, fingering herself before joining in, her tongue rimming Emily’s tight asshole as I ate her out. “Taste my daughter, stranger. She’s so wet for you.” The grandmas weren’t shy. Margaret, at 70, knelt behind me, her experienced tongue tracing my balls before diving into my ass, rimming me with slow, deliberate circles that made my cock throb. “Mmm, such a tasty man,” she purred, her wrinkled hands spreading my cheeks. Her granddaughter, Sarah’s girl Mia, 21 and eager, grabbed a hotel shampoo bottle from the nightstand. “You like objects, huh? Let’s play.” She lubed it up with spit and eased it into Margaret’s pussy as the older woman licked me, the bottle sliding in and out while Margaret gasped, “Deeper, baby girl, fuck Grandma good.” Anal was next on the menu. Tanya, the 35-year-old firecracker, bent over the bed, her round ass up. “Fuck my ass, big boy. Make it hurt so good.” I slid into her tight hole, pounding as Vanessa, 50 and full-figured, tongued my shaft from below, licking where I entered Tanya. The group cheered, passing around more improvised toys—a hairbrush handle for Sarah’s ass, a cucumber from the room service fruit basket that Emily inserted into her own mom’s pussy while rimming her. Incestuous vibes thickened the air.

Lisa and Emily made out passionately, daughter tonguing mother’s clit as I fucked Lisa from behind. “Eat Mommy’s pussy, sweetie,” Lisa groaned. Grandma Margaret joined, her tongue rimming Emily’s ass while the young one devoured her mom. Sarah and Mia mirrored them—Mia on all fours, Sarah inserting a wine bottle neck into her daughter’s ass, twisting it slowly as Mia cried out in ecstasy. “Yes, Mom, stretch me!” I moved through them like a king in his harem. Rimming Vanessa’s mature asshole while she licked Tanya’s; inserting fingers, then a remote control into young Mia’s pussy as her grandma watched approvingly. The oldest, a 70-year-old friend named Evelyn, surprised everyone by taking my cock up her ass, her loose but eager hole gripping me as the group tongued her clit and nipples.

Hours blurred into a frenzy of licking, rimming, and insertions. Cum splashed across faces—mine on Emily’s tongue, hers on her grandma’s tits. Objects everywhere: bottles, brushes, even a rolled-up magazine that Sarah used to fuck her sister’s ass while I rimmed them both.

As dawn broke, we collapsed in a sweaty, satisfied pile. “Best business trip ever,” I murmured. Lisa smiled, “Come back anytime, stranger. Family nights just got dirtier.”