
My online hookup ended up being my boss
All characters are above the age of 18.
Another boring Saturday night. Tinder was dead, matches that never went anywhere, messages left on read. I was horny, frustrated, and tired of the same old nothing. So I switched over to Doublelist, scrolling through the local ads. Plenty of guys looking for tops, vague profiles, dick pics with no personality. Most of them I’d swipe past without a second thought.
One stood out.
Male, 44, bi curious, top. Looking for someone willing to deal with someone new. Body pics attached.
The photos showed a solid, masculine frame broad chest, thick arm. He looked like he could handle himself. I usually avoided new guys because they often got in their heads and went soft, but something about this one felt different. I remembered how nervous I’d been the first time I put myself out there as a bottom and how an experienced guy had made it easy. Plus, he was upfront about what he wanted.
I messaged him.
We went back and forth pretty quickly. I told him I was a 26 year old bi bottom, open to seeing if there was chemistry. He said he was mostly into being dominant and had a specific kink for seeing guys in panties. That made me smile. I had a small collection for nights when I wanted to feel sexy and feminine lace, satin, things that hugged my ass and made my cock look smaller and cuter tucked away.
I told him I was game. He seemed down for pretty much anything else, but the panties and dominance were non negotiable for him. Fair enough. I liked the idea of submitting like that.
He asked if I wanted to come over to his place. I hesitated for a second meeting at someone’s house always carried a little risk but I didn’t want to get fucked in a gas station bathroom or some cheap motel. His place sounded better. We set a time for an hour from now. I got ready.
Showered, made sure I was smooth, and picked out the right pair, soft blue lace bikini panties. They sat low on my hips, the front pouch keeping everything neat and feminine, the back riding up between my cheeks. I pulled my jeans on over them, threw on a t shirt, and headed out. The whole drive over my stomach was tight with nerves and excitement. I almost turned around twice, but I didn’t.
I pulled up to a nice house in a quiet neighborhood, walked up, and knocked.
The door opened.
My brain short circuited.
It was Bryan.
My boss. 44 years old, the same solid build from the photos, salt and pepper hair, that calm, authoritative presence I saw every day at work. We both just stared at each other for a long second.
“Milo,” he said, voice tight.
“Bryan,” I managed.
The silence was heavy.
“This is… awkward as hell,” I said finally. “It’s cold out here. Can I come in at least?”
He stepped aside without a word. I walked in and he closed the door behind me. We stood there in his living room like two idiots who had no idea what to do next.
“So… we don’t have to do this,” I said. “I can just go. We can pretend it never happened.”
He nodded slowly. “Yeah. Probably smart.”
Another pause. His eyes dragged down my body and back up. Something in his face changed the professional mask slipped and something darker, hungrier took its place. His voice dropped, lower and rougher than I’d ever heard it at work.
“Did you wear the panties?”
My heart slammed against my ribs. I could still leave. I could laugh it off. But the way he asked the shift in his tone sent heat straight through me.
I swallowed. “Yes.”
“Show me.”
My hands shook a little as I unbuttoned my jeans and pushed them down just far enough. The blue lace peeked out, delicate against my skin, the front pouch already starting to strain as my cock stirred from the tension and the way he was looking at me.
Bryan stared. His tongue wet his bottom lip. When he spoke again, there was no trace of the guy from the office.
“I’m okay with this if you are.”
I looked at him really looked. The risk was insane. But my body had already decided. The kink match was too perfect, the pull too strong.
“Yes,” I said. “I am.”
He stepped in close, one hand settling on my shoulder, heavy and possessive.
“Good. Take off your pants…..”
I kicked off my shoes and stepped out of the jeans, standing there in just the t shirt and those blue lace panties. My cock was visibly half hard now, outlined obscenely in the delicate fabric.
Bryan watched with open approval. “Now take off mine.”
I moved forward on slightly unsteady legs, unbuckled his belt, popped the button, and dragged his pants and underwear down. His cock sprang out thick, heavy, already hardening, a nice flushed head and a solid shaft that made my mouth water. I wrapped my hand around it once, stroking slowly.
“On your knees,” he ordered.
I dropped. The floor was cool under my bare knees. I leaned in and took the head into my mouth, tasting salt and skin and the faint musk of him. I sucked gently at first, swirling my tongue, working him deeper as he thickened against my tongue. His hand settled on the back of my head, not forcing yet, just guiding.
“Fuck, that’s it,” he growled. “Suck it like you came here to do exactly that.”
I moaned around him and took more. He started rocking his hips, fucking my mouth in slow, controlled thrusts. Spit slicked his shaft. The lace of my panties felt tight and sinful around my own cock, every shift of my body making the fabric rub. Jesus Christ why was this so fucking hotm
“Look at you,” he said, voice low and filthy. “On your knees in those pretty little panties, choking on my cock. Such a good little panty slut. You wore those for me, didn’t you?”
I moaned again, the words hitting me hard. Yes. God, yes.
He pulled me off after a few minutes, gripping my hair. “Up. Bedroom. Now.”
I followed him down the hall on shaky legs, cock straining against the lace. He pushed me into a dimly lit room with a big bed and turned me to face it.
“Shirt off.”
I pulled the t shirt over my head. He shoved me forward onto the bed on my stomach, then yanked my hips up so I was ass up, face down. The position made me feel exposed and vulnerable in the best way.
He grabbed lube from the nightstand. Cool slick fingers circled my hole, then one pushed inside. I gasped into the mattress.
“Tight,” he murmured, almost to himself. “Gonna open you up nice and slow for my cock. You want that, pretty thing? Want me to fuck you while you’re wearing these slutty little panties?”
“Yes,” I breathed. “Please.”
He slowly started to finger my holemy. I pushed back against his hand, moaning, wanting more. He worked me open patiently but thoroughly, adding more lube until I was slick and ready and desperate.
He pulled his fingers out. I heard the wet sound of him stroking lube over his cock. Then the blunt head pressed against my entrance.
“Beg for it.”
“Please,” I said, voice already wrecked. “Please fuck me. I need your cock.”
He pushed in slowly, letting me feel every thick inch as he stretched me open. The burn was perfect. When he bottomed out, hips flush against my ass, he stayed there for a moment, hands gripping my waist over the lace waistband of the panties.
“Fuck,” he groaned. “You feel good. So fucking tight around me.”
He started moving long, deep strokes at first, letting me adjust. The panties were still on, bunched and twisted around my thighs now, the lace framing everything. Every thrust made the fabric shift against my skin.
He picked up speed gradually, hips snapping harder, the wet sound of his cock driving into me filling the room. One hand slid up my back and pressed between my shoulder blades, pinning me down while he fucked me deeper.
“Take it,” he snarled. “Take every fucking inch. This is what you came here for, isn’t it? Dressed up in your panties like a little whore, begging to get your hole wrecked.”
“Yes....fuck....yes!” I cried out, pushing back to meet every thrust.
He was relentless now, pounding into me with steady, powerful strokes that nailed my prostate every time. The pressure built fast and intense. I didn’t even need a hand on my cock the way he was fucking me was enough. My moans turned higher, more desperate.
He pulled out suddenly, flipped me onto my back, and hooked my legs over his shoulders. The panties were still tangled around one thigh. He pushed back inside in one smooth thrust and started fucking me even harder, eyes locked on mine.
“Watch me while I use you,” he demanded. “Look at me while I fuck this tight little hole.”
I did. I couldn’t look away. His face was flushed, jaw tight, pure dominant hunger as he pounded into me. The bed creaked. My cock bounced against my stomach with every thrust, leaking steadily onto my skin and the lace still caught around my thigh.
He leaned down, biting at my neck, sucking hard enough to leave marks. One hand gripped my thigh, holding me open while he drove into me with brutal, perfect rhythm.
“Gonna fill you up,” he growled against my ear. “Gonna breed this pretty little panty slut. You want that? Want my cum deep in your ass?”
“Yes....please....fuck, Bryan....”
The orgasm hit me without warning. My hole clenched hard around him as I came untouched, cum spurting across my stomach and soaking into the blue lace still wrapped around my thigh. The intensity of it made me shake.
Bryan groaned at the feeling of me tightening around him. He slammed in deep, hips stuttering, and came with a low, rough sound pulsing hot and thick inside me, filling me up exactly like he promised. He kept thrusting through it, grinding deep, making sure I took every drop.
When he finally slowed and stilled, we were both breathing hard. He stayed buried in me for a long moment, forehead resting against mine. Then he pulled out slowly. I felt his cum leak out of my used hole, warm and slick, further messing the already ruined panties.
He collapsed beside me and pulled me against his chest without a word. I lay there in the afterglow, body still trembling, lace sticky against my skin, ass sore in the best way.
For a while, neither of us said anything about what had just happened or who we were to each other outside this room. The only sounds were our breathing and the faint hum of the house.
Eventually he spoke, voice rough but quieter.
“Stay a little longer if you want.”
I nodded against his shoulder, not ready to move yet.
After we caught our breath, Bryan got up and asked if I wanted a drink. I said sure.
He came back a minute later with two glasses and handed me one. We sat on the edge of the bed, still half dressed, the air between us thick with everything we’d just done.
He took a sip and said, “Let’s just have this be a one time thing. Otherwise it’s gonna get real awkward at work.”
I nodded, swirling the drink in my glass. “Yeah. Just getting some sexual frustration out. No big deal.”
I glanced over at him. “You’re pretty good, though. Are you sure you’ve never been with a guy before?”
Bryan laughed, low and a little sheepish. “No. You’re my first. I’ve been wanting to for a while, I just… kind of chickened out every time. To be honest with you, I almost chickened out tonight too.” He paused, then added, “I was always the dominant one with my ex wife. When she wore red panties, it meant she wanted to be dominated. It was fun while it lasted.”
I smiled into my glass. “Sounds hot.”
“I almost chickened out too,” I admitted.
We finished our drinks in a comfortable silence. Eventually we said our goodbyes at the door. No kiss, no promises. Just a quiet “See you at work” before I headed home.
The next morning I stood in front of my dresser in just a towel, staring at my usual black boxer briefs. My mind kept drifting back to last night the way Bryan had looked at me in those blue panties, the filthy things he’d said, the way he’d fucked me like he owned me. The forbidden thrill of it all made my cock twitch.
Before I could talk myself out of it, I opened the drawer where I kept my collection and pulled out a pair of red lace panties. I stepped into them, pulled them up, and adjusted myself. The lace hugged my ass and sat low on my hips. Under my work uniform, no one would know…. yeah totally I knew what I was trying to do. Maybe it was a bad decision but I'm committed.
I got dressed, the red lace hidden beneath my pants, and headed in.
The restaurant was already buzzing when I arrived. Breakfast rush in full swing. I was on seating duty today, plus helping wherever they needed me basically a utilitarian tool running between the host stand, the floor, and the back. I saw Bryan a couple of times. We exchanged normal pleasantries, the same way we always did. No lingering looks. No mention of last night. Just two coworkers.
The rush stayed busy. One of the waitresses caught me between tables and asked if I could help Bryan in the walk in cooler. He was portioning out food for the next wave.
I said okay and headed back.
When I stepped into the cooler, the cold air hit me immediately. Bryan was already in there, sleeves rolled up, working at the prep table. The second I saw him, that same low thrum from last night rolled through me. I kept my face neutral and tried to ignore the way my cock was starting to harden in the red lace. The cold helped… a little.
“Hey,” he said, not looking up.
“Hey.”
We got to work portioning food together. For a few minutes it was normal just boss and employee moving product. Then he asked me to grab a container off the lower shelf in the back.
I crouched down and started looking. After a second I realized I couldn’t find it.
“It’s not here,” I called over my shoulder.
Bryan didn’t answer right away.
I glanced back at him.
He was staring.
My uniform pants had ridden down a little when I bent over. The bright red lace waistband was clearly visible above them. I stayed exactly where I was for a moment, heart pounding, letting him look. I didn’t want to move. I wanted him to stare.
Slowly, I reached back and tugged my pants up, taking my time. The lace disappeared inch by inch.
Bryan blinked hard, like he’d been caught. He cleared his throat and pointed toward the other side of the cooler.
“It’s over there.”
I got up, found the container, and brought it over. We went back to portioning like nothing had happened. But the air in the cooler felt different now.
The rest of the shift stayed hectic. A while later the busboy came up to me and said Bryan wanted to see me in his office.
I wiped my hands on a towel and headed down the short hallway. When I stepped inside, Bryan was sitting behind his desk.
“Close the door,” he said. “Lock it.”
I did.
He leaned back in his chair and looked at me for a long moment.
“I thought we were keeping last night a one time thing.”
I tilted my head, playing innocent. “Whatever do you mean, sir?”
He just stared.
I hooked my thumbs into the waistband of my pants and slowly pulled it down just enough to show the bright red lace underneath.
“Oh. This?” I asked softly. “I just like to wear them sometimes. Is that a problem, sir?”
Bryan’s jaw tightened. His eyes stayed on the red lace.
“It can be,” he said, voice low, “if you keep teasing me like that.”
I let the waistband snap back into place and met his eyes.
“What’s the punishment then?”
He didn’t hesitate.
“On your knees.”
I dropped without another word.
Bryan stood up, came around the desk, and unbuckled his belt. He pulled his cock out already hard and stepped in close. One hand gripped the back of my head as he fed it into my mouth.
He didn’t start slow this time.
He fucked my throat in steady, controlled thrusts, using my mouth like he had every right to. I relaxed as best I could, taking him deep, eyes watering while he held me in place. The risk of it locked office door or not made my cock throb inside the red lace.
He didn’t say much. Just low, rough sounds and the occasional “Fuck” under his breath as he used me. When he got close he pushed in deep and held me there, cumming hard down my throat. I swallowed every pulse, throat working around him until he finally let go.
Bryan pulled out slowly, breathing heavy. He tucked himself away and looked down at me still on my knees.
“Stay after work.”
I wiped my mouth with the back of my hand and nodded.
“Yes, sir.”
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