The Workplace Hookup

An SPH Experience by frddygotfingered28.


I’d been working at this busy Italian restaurant for about six months, slinging plates and dodging spills, when I started noticing Cindy. She was a server too—petite, with short blonde hair, freckles across her nose, and this flirty energy that lit up the dining room. We were both in our early 20s, and after closing shifts, we’d linger, chatting over leftover breadsticks. One night, she suggested grabbing drinks at the dive bar down the street. ‘Why not?‘ I thought. My dick—usually a modest 1.5 inches soft, shaved smooth in hopes of something like this—twitched at the idea.

The bar was dim, with sticky floors and cheap beer. We knocked back a couple of rounds, her knee brushing mine under the table. Soon, her hand was on my thigh, fingers tracing higher. I leaned in, our lips crashing together right there in the corner booth. Tongues tangled, breaths hot, her nails digging into my arm. We stumbled out to the parking lot, piling into my beat-up sedan. The windows fogged quick as we made out like teenagers—her straddling my lap, grinding against the growing bulge in my jeans. I cupped her ass, pulling her closer, my small cock straining but not quite filling the space like I wished it could.

“Let’s go to your place,” she whispered, nipping my ear.

Heart pounding, I drove us back, the tension thick enough to cut.

We barely made it through my apartment door before clothes started flying. Her shirt hit the floor, revealing a lacy black bra hugging her perky tits. I yanked off my tee, then we tumbled onto the bed, mouths hungry. My hands roamed her body, sliding down to her jean shorts. I fumbled with the button, popping it open, then tugged at the waistband. But underneath? A onesie—some snap-crotch thing for easy access, I guessed. My fingers scrabbled at the weird metal clip between her legs, slick with sweat and nerves. It wouldn’t budge.

“Come on,” I muttered, cheeks burning as she started giggling.

“You’re killing me here,” she laughed, her voice light but teasing.

The sound hit like a gut punch—my confidence cracking. I could feel my dick retreating, that nervous shrink hitting hard. Finally, she reached down, popped the clip with ease, and spread her legs.

“There. Now finger me like you mean it.”

Her pussy was already wet, lips puffy and inviting. I slid a finger in, then two, curling them against her walls as she moaned softly. But the embarrassment lingered, my soft little nub tucked away, refusing to rally.

I pulled back, letting her take the lead. She grinned, pushing me onto my back, her hand grazing over my boxers. The fabric tented weakly—maybe two inches at best. She rubbed the outline, slow circles that made me throb, then leaned down, planting a few kisses through the cotton.

“Mmm, excited?” she murmured. But I could see it in her eyes—the subtle furrow of her brow, the way her lips pursed.

She hooked her fingers in the waistband and tugged down. There it was: my 1.5-inch soft dick, bald and baby-smooth from the shave, looking pathetic against my thigh, and there was no hiding it.

She gasped, sharp and genuine, her eyes widening. “Oh… wow.” Her thumb and forefinger pinched the base, rolling it gently like it was a toy. She tugged lightly, watching it flop. “It’s… cute.”

I felt heat flood my face, but the humiliation stirred something deep—my dick twitching, blood rushing in despite the shame. It stiffened slowly, inching up to about 3.5 inches erect, the head peeking out, veins straining. But that was it. Full mast, and still so damn small. She flicked it once, twice, her expression shifting from curiosity to disappointment. No words, but the silence screamed.

“Sorry,” I blurted, voice cracking. “It’s not you—it’s just nerves.”

She shrugged, naked now, her body flawless under the dim lamp—firm ass, trimmed bush—but the spark was gone. We lay there, skin on skin, for maybe 20 minutes tops. She poked at my erection a couple more times, but it felt obligatory. Then she sat up, grabbing her clothes.

“I should head out. See you at work.”

As she dressed, her eyes dropped to my crotch, now soft again, no bulge to speak of in my boxers. That smirk—pity mixed with amusement—burned into me. The door clicked shut, leaving me alone with my shriveled dick and a raging hard-on from the rejection.

Work the next few days?

Awkward as hell.

Cindy avoided eye contact during rush, her smiles polite but distant—no more after-shift invites. “Girls’ night,” she’d say when I hinted, brushing past with a tray.

I stopped pushing, the rejection sinking in.

Was it the size?

Nah, couldn’t be.

But deep down, I knew.

Weeks dragged on until Tina, another coworker, threw a pool party at her place—a sprawling backyard bash with grills and coolers. Most of the staff showed: servers, cooks, the whole crew in swimsuits. I rocked board shorts, hoping the water would hide any outlines. Cindy was there in a bikini, looking killer, chatting with everyone. We ended up alone by the pool edge, the sun beating down, the chlorine scent thick. Flirting kicked off easy—her leaning close, water droplets from an earlier dip glistening on her skin. My dick stirred, hardening fast against the fabric. It poked out, a tiny tent that I tried to angle away.

“Someone’s little guy is excited,” Cindy said, her voice dripping with mock surprise, eyes locked on the protrusion.

Before I could respond, impulse hit. I grabbed her waist, pulling her with me as I cannonballed into the deep end. Water exploded around us. Surfacing, I pressed close, hoping the underwater view would impress—maybe make it look bigger in the ripples. But she shoved me back hard, her foot connecting with my thigh.

“Get your dicklette away from me!” Cindy yelped, half-laughing, half-serious.

She splashed a wave in my face and hauled herself out, ass flexing as she climbed the ladder, leaving me treading water with a deflating erection and stinging cheeks.

Dripping and defeated, I toweled off and joined the group at a picnic table—beers in hand, stories flying. The vibe was loose until Cindy, mid-sip, turned to the crowd and fixed her gaze on me. “Hey, everyone… Sam has a small dick. That’s why we stopped hanging out after shifts.”

Deadpan, no giggles from her, just that stare.

The table went quiet.

Forks paused, eyes flicked to me—some widening, others averting.

No one laughed; it was worse, that awkward pity hanging in the air like humidity.

My face burned crimson, hands clenching under the table where my soft nub hid. I mumbled something incoherent and stared at my plate, the humiliation pooling hot in my gut, my dick betraying me with a forbidden twitch.

I stuck it out at the restaurant a couple more months, quitting for a better gig, not the whispers, but the damage was done.

The girls knew now.

I’d catch them glancing at my apron, suppressing smirks, or worse: that universal small-dick sign—thumb and forefinger pinched close—as they breezed by the kitchen.

“Small Dick Sam,” one whispered once, loud enough to echo.

It mortified me, shrinking me shorter each time.

But fuck, it turned me on, too. The constant tease, the way they’d eye my crotch like it was a joke. The guys? They picked up on it quick. “Beta Sam,” they’d rib during slow shifts, slapping my back a little too hard, comparing their own packages in the locker room while I changed, facing the wall.

One even joked about ‘measuring up’ during inventory, the whole crew chuckling.

I played it off, but inside? That mix of shame and arousal kept me jerking off to the memories—Cindy’s gasp, the pool shove, the table announcement.

Hot as hell, even if it wrecked my ego.

 

The End.

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