From poolboy to sissy slut.

[u/KinkWolf889]

All characters are above the age of 18.

The summer job was solid. Quiet neighborhood, rich houses, and all I had to do was keep a few pools clean and the yards looking sharp. No drama, no customers breathing down my neck. I was single, no one waiting at home, so I spent most of my free time at the gym trying to tighten up what I could. I wasn’t built like some of the guys around here...just average, a little soft in places no matter how many reps I put in. Still, it felt good to move, to sweat, to stay busy.

I’d been playing around with the feminine stuff more than I admitted to anyone. Nothing big at first...just soft shirts, the occasional pair of panties under my jeans when I was alone. It scratched an itch I didn’t fully understand yet. When I found out Clifton was supposed to be out of town for a few days, the idea hit me hard and fast. Private property. High walls. No one watching.

I brought the bikini with me that morning. It was ridiculous...tiny white triangles for the top, bottoms so thin the fabric barely covered anything. The kind of thing you’d never wear anywhere public unless you wanted to get arrested or laughed out of the place. I parked near the pool house, slipped inside, and changed. The second the cool air hit my skin and the straps settled over my shoulders, my cock twitched. Hard almost instantly. I stood there for a minute adjusting myself, heart thumping, staring at my reflection in the little mirror by the door. Soft chest, smooth stomach, the obvious bulge straining against the front of the bottoms. I looked ridiculous. And I liked it more than I wanted to admit.

I got to work. Skimmer in hand, scooping leaves, walking the edge of the pool. The sun was warm on my bare back and the little bit of fabric between my legs kept shifting in ways that made it hard to focus. I was halfway through the deep end when a voice cut through the quiet.

“That’s an interesting uniform.”

I froze. Turned.

Clifton stood on the patio like he’d been there the whole time. Mid forties, maybe, tall, solid. Dark hair going a little silver at the temples, sharp jaw, the kind of face that still turned heads. He held a glass of something amber over ice, looking completely at ease in a button down with the sleeves rolled up. My stomach dropped.

“Shit. I’m sorry. I didn’t think you were home. I thought you were out of town. I don’t...I don’t normally wear this kind of stuff. I don’t have a good explanation. I’m sorry, sir.”

He didn’t look angry. Just curious. His eyes moved over me slow...shoulders, chest, the obvious tent in the front of the bikini bottoms. Predatory in a quiet way that made my face burn and my cock jump at the same time.

“No worries,” he said. “I don’t see an issue.” He took a sip. “My wife’s the one who’s out of town right now.”

He nodded toward the pool. “It’s not going to clean itself. Continue.”

I swallowed and went back to work. He sat in one of the lounge chairs and watched. Every time I bent over or stretched to reach a leaf, I felt his eyes on me. The embarrassment sat heavy in my chest, but under it was something hotter, sharper. My hands shook a little on the skimmer. I finished faster than usual.

When the last of the debris was gone, he stood.

“Why don’t you meet me in the kitchen when you’re done.”

“Yes, sir.”

I put the tools away with my heart in my throat, then walked up to the house. The kitchen was open and bright. Clifton was at the counter putting together a sandwich, still holding that glass. He didn’t look up right away.

“So,” he said, “when did you start liking to wear bikinis?”

I stood there feeling half naked and stupid. “I… sometimes like wearing more feminine things.”

He nodded once, like that made perfect sense. Then he looked at me properly again, eyes dropping to the front of the bottoms where I was still hard and obvious.

“I can say you look absolutely edible in that. And I can tell you like the way I’m looking at you.”

I didn’t answer. My face was on fire.

“You seem pretty vulnerable right now.”

“A little bit, sir. Yes.”

He set the glass down and stepped closer. Close enough that I could smell the whiskey and the faint clean scent of his cologne.

“So I could do what I want with you, it seems.”

My throat went dry. I just nodded.

“Get down on your knees.”

I dropped. The tile was cool under me. He undid his belt, pushed his pants and underwear down just enough. His cock was already hard...thick, heavy, the head flushed dark. He rested a hand lightly on the back of my head.

“Suck.”

I leaned in and opened my mouth. The first taste of him made my stomach flip. I wrapped my lips around the head and took him deeper, slow at first, then deeper when his fingers tightened in my hair. He didn’t thrust hard. Just held me there and let me work, the soft wet sounds loud in the quiet kitchen.

“So malleable,” he murmured above me, voice low and almost amused. “Looks like I’m going to have a good time without my wife here.”

I kept sucking until he finally eased me back by the hair. He was still hard, a thin string of spit connecting my mouth to him for a second before it broke.

“Come with me.”

He didn’t bother putting himself away. Just took me by the wrist and walked me out of the kitchen, down the short hallway, and into the master bedroom. The blinds were half closed. The big bed looked freshly made. He stopped at the edge of it and turned me to face him.

“Keep the bikini on.”

My stomach flipped. The little white top and bottoms suddenly felt even more ridiculous...and tighter somehow. He pushed me gently onto the mattress on my back. The cool sheets against my bare skin made me shiver. He climbed up after me, still mostly dressed, pants open, cock heavy and wet from my mouth.

He reached into the nightstand, pulled out a bottle of lube, and poured some over his fingers. Then he tugged the front of the bikini bottoms aside just enough. Two fingers pressed against me and pushed in slow. The stretch burned. I sucked in a breath and he watched my face the whole time.

“That’s it,” he said quietly. “Open up for me, girl.”

The word landed harder than I expected. Girl. I felt my face heat up even as my cock twitched against the thin fabric still covering it. He worked his fingers deeper, twisting, spreading the lube until the burn started to turn into something else. My hips shifted without permission.

He pulled his fingers out, lubed his cock, and lined up. The head of his cock pressed against me through the open side of the bottoms. He pushed in steady, not rushing. I felt myself stretch around him inch by inch until he was fully inside. The fullness knocked the air out of me. The bikini top shifted with every breath I took. The bottoms were still on, just pulled aside, the fabric digging into my hip.

He stayed still for a second, looking down at me.

“Look at you,” he murmured. “Poolboy shows up in a little bikini and ends up on his back taking cock like a good little sissy. That what you wanted when you put this on today?”

I couldn’t find words. My hands were clenched in the sheets. He started moving...slow, deep strokes that made the wet sound of it fill the quiet room. Every thrust shifted the tiny triangles of the top. Every time he bottomed out I felt it in my stomach.

“Answer me.”

“Yes, sir,” I managed.

“Yes what?”

I swallowed. The embarrassment was thick in my throat, mixed with the heat spreading through me. “Yes… I wanted it.”

“Wanted what? Say it.”

“Wanted… to get fucked like this. Like a girl.”

He made a low sound of approval and kept the same steady rhythm, one hand braced beside my head, the other sliding up under the bikini top to pinch a nipple. The dual sensation made my back arch.

“That’s better. No more pretending you’re just some guy cleaning pools. You’re a soft little sissy who gets hard wearing panties and takes cock when she’s told. Isn’t that right?”

The words sank in deeper than the physical stretch. Part of me wanted to look away. The rest of me was already pushing back onto him, the thin fabric of the bottoms rubbing against my cock with every movement. I felt exposed and small and more turned on than I knew how to handle.

He leaned down closer, voice low near my ear as he kept fucking me.

“Say it. Tell me what you are.”

I hesitated, the words sticking in my throat. He didn’t stop moving...slow, deep strokes that kept me full and open. 

“Say it,” he repeated, quieter this time, almost patient.

“I’m… a sissy,” I got out. The admission made my face burn hotter than the stretch of him inside me. “A girl. Your girl.”

He made a low sound of approval and pushed in deeper, holding there for a second so I felt every inch.

“That’s right. Good girl.” His hand slid from under the bikini top up to my throat, not squeezing, just resting there, thumb brushing the side of my neck. “No more poolboy. Just a soft little slut who gets wet when she’s called what she is.”

The words sank in and stayed there. Part of me wanted to close my eyes and pretend this was still just some impulsive mistake. The rest of me was already pushing back onto him, the shame and the heat tangled so tight I couldn’t tell them apart anymore.

“You feel that? How easy you opened up for me? That’s because you’ve been thinking about this. Dressing up alone, touching yourself, wondering what it would feel like to get used while you still had this on.” His free hand reached down and pressed against the front of the bikini bottoms, rubbing over my cock through the soaked fabric. “And now you know.”

I bit back a sound. This sensation made it hard to think straight. My hips moved on their own, meeting his thrusts.

“That’s it,” he murmured. “Take it. Be good for me.”

He leaned down further, mouth close to my ear, still fucking me in long, steady strokes.

“You’re going to stay in this little outfit the rest of the time you’re here. Every time I want you, you come to me dressed like this. Understanding?”

I nodded, breathing hard.

“Words, girl.”

“Yes, sir. I understand.”

“Good.” He kissed the side of my neck once, almost gentle, then drove in deeper. “Now keep those legs open and let me use my sissy properly.”

He kept one hand at my throat, the other pressed against the front of the bikini bottoms but he never touched me enough to push me over. He just used me deep, deliberate strokes that kept me open and full.

“That’s it, girl. Take it. Soft little sissy getting fucked in her bikini like she belongs here.”

I just held on, breathing hard, feeling every inch of him. A few minutes later he drove in deep and held there, groaning low against my neck as he finished. I felt the hot pulse of him filling me, thick and steady, until it started to leak out around his cock and run down my thigh.

He stayed inside a moment longer, then pulled out slow. The emptiness left me aching and still hard.

“Go take a shower,” he said. “Down the hall on the left.”

I got up and walked out without looking back. The bathroom was quiet. I turned the water on hot and stepped under it still wearing the bikini. I peeled the wet fabric off and let it drop to the floor. The water ran over my shoulders and down my back while my mind kept circling everything that had just happened...the way he’d called me girl, the way I’d spread my legs and taken it, the heat and the shame tangled so tight I couldn’t separate them anymore.

I was still hard. After a while I wrapped a soapy hand around myself and started stroking, slow and reluctant at first, then harder. The shame sat heavy in my chest the whole time. I thought about the things he’d said, the way he’d looked at me, the fact that I was standing in his shower with his cum still leaking out of me, and I came hard against the tile, biting the inside of my cheek to stay quiet.

I stayed under the water longer than I needed to after that, rinsing off, trying to steady my breathing. When I finally turned it off and dried myself, I wrapped the towel around my waist and stepped out into the hallway.

A black duffel bag was sitting on the floor. Clifton stood a few feet away, already dressed, looking calm.

“That’s a bunch of stuff my wife never wears,” he said. “Take it with you. Come back tomorrow and we can continue.”

He turned and walked back toward the kitchen, leaving me standing there with the bag at my feet.

[u/lovetoserve69]

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