This story was originally posted at https://www.gaycupidstories.com/story/show/10002323 on 2021-08-27.
Nick hires a lawn boy called Oliver. A short story I wrote in the Homotextual Gaming Guild Discord community.
Author note: This story was originally written on the Homotextual Gaming Guild Discord community. Each section break offered readers two choices, and the votes determined the course of the plot. Images accompanied some sections of the story; links to these have been added here and there.
“Hey,” I called to the hot guy on his bike. For some reason, even in the heat of summer, he was wearing a grey beanie, matching his cycling shorts. “You looking to earn some money?”
“Um, maybe,” the hot guy replied. “What do you need?”
“Oh, just a few things here and there. Front yard needs mowing, there’s a patch of brush to put in the garbage, and some birds are building a nest on my back porch. You mind helping me out for a bit?”
“You want me to be your lawn boy, Mr…” He squinted at my mailbox. “Turner?”
“Nick. Mr. Turner sounds so formal. And, well… I guess. But I’ll make it worth your time.”
“Nick.” He smiled and held out his hand, which I took. “Sure. I’m Oliver.” He walked his bike over to my shed. I showed him to my equipment.
He spent the next hour or so in the 87°F heat, stripped to the waist, working on my yard. Never once took off that beanie, though.
“You must be boiling in that hat,” I said, when he’d finished mowing around the flowerbeds. “Do you want to come in for a shower?”
He grinned. “I’d like that.” I showed him to the bathroom, watched him start the water running. “Oh, by the way, Nick,” and there was something predatory in the way he gazed at me, “we never discussed how much you’d be willing to part with to get your yard done.”
“No, we didn’t, did we…”
Then we were in the shower, kissing furiously, my hands clutching his ass, his back, and his working my dick until I came all over my stomach. He pushed me to my knees and I took his dick into my mouth, while the warm water cascaded all around me. “Fuck yeah…” he hissed, as he came in my mouth and I swallowed his load.
That shower was the best part. Although getting my yard sorted out came a close second.
Afterwards, I offered him $30 for his time. “This from your lawn boy fund? It’s fine, you keep it,” he winked.
We swapped numbers.
I meant to leave it a day or so before messaging him, but then I noticed he’d left his beanie behind…
So a week went by where either I was busy, or Oliver was unavailable. Perhaps he just wasn’t that interested in me. Or maybe he’d met someone else, or he was keeping his options open. Either way, we’d stopped messaging.
Then on Saturday, I popped into town to pick up a few supplies from one of the home stores. There was an astroturfed area outside where some shirtless male models in jeans were demonstrating some gardening equipment from one of the nearby stores. As I was passing by I heard a familiar voice.
“Then I got him in the shower and he sucked me off. Couldn’t get enough of my hot bod. I think he wants to see me again, but I…”
“Oliver?” I said. He turned around, nonchalant. “Oh, hey… Nick! How are you? I was just telling my buddy Jackson about you.” Jackson smirked as he looked at me. I offered a handshake, and after a second he took it.
“Been busy?” I asked Oliver, a little pointedly.
He picked up on my tone. “Nick, I’m sorry. Come on, let’s talk, one on one,” he said as he grabbed my hand and led me to a display model of a garden shed.
As soon as the door closed behind me, Oliver pinned me against the back wall of the shed, holding me against the wall with his body. I was instantly hard as he trailed his hand down my chest and cupped my groin.
“This is what you wanted, isn’t it?” he whispered. “Getting fucked in this shed in the middle of town. People walking by outside, no idea what’s going on in here? Maybe after we’re done here, I’ll let Jackson have sloppy seconds. Then we’ll get the other guys in here. You’d like that, wouldn’t you?”
“…yes,” I said quietly.
“Thought so,” Oliver said. “Go on then. Clothes off, then bend over that workbench.”
Why I am doing this? I asked myself as I undid my shirt buttons and slipped it off, then started removing my pants. I mean, he’s hot, but this isn’t what I really want, is it…?
I leaned over the bench and let Oliver, still in his jeans, push me down on my front. I could feel the warmth of his hand on my back and the cold polished steel surface of the bench against my chest. My dick was rock-hard, but trapped against the side of the workbench, I couldn’t quite reach it. I heard Oliver unzip his jeans. I turned around and saw him take out a tiny bottle of lube. He coated his dick in it, seven solid inches of meat, then squirted a little more onto his fingers and pushed them into my hole.
I gritted my teeth as Oliver followed up with his dick. He entered me gently at first. “You okay?” he asked. I nodded. “Good.” With that, he began to thrust inside me in earnest. I held on to the bench as he fucked me, feeling the rough fabric of his jeans caressing my ass with each thrust. There was a window facing me, a little dust blurring the view, but I could see people outside walking past the shed.
“Shit, guess I owe you twenty dollars.” I tried to push myself off the workbench, but Oliver was still holding me down. Jackson was standing at the entrance to the shed.
“Guess so,” said Oliver. Then to me, “You don’t mind if Jackson gets in on the action, do you?” He wrapped his fingers around my dick, giving it a good long stroke, and I moaned. “Thought so.”
Jackson smirked at me, before stepping round to the front of the workbench. His cock was already out of his jeans, the thick, cut head a deep purple against the dark skin of his shaft. I kept my lips shut as Jackson rubbed his dick against my face. “Oh, he’s being a stubborn bitch,” said Jackson.
I opened my mouth and let Jackson slide his thick tool past my lips. I could feel his trimmed treasure trail against my nose and smell his musk as I explored his shaft with my tongue. “Oh, yeah, just like that,” Jackson growled, his hand resting on the back of my neck.
Oliver had started fucking me again. His cock was really working me over hard, and I was building up to an intense climax. I sensed he was close, too, his breaths coming short and fast. He grabbed my hips and pulled me close as he sank his cock into my hole and blasted his load deep inside, while I sucked hard on Jackson’s tool. I felt Oliver pull out, disappointed that I didn’t manage to cum at the same time. Jackson withdrew his dick. “My turn.” I lay on the bench as Jackson filled my hole with his dick, using Oliver’s load as lube. “I’ll get the others,” Oliver said, leaving me speared on Jackson’s dick. “Hey! Where are you going?” I said, but Oliver had already slipped out of the shed. As I stood up, Jackson wrapped his muscular arms around my body, one hand grasping my hard cock.
“Relax, Nick,” said Jackson. “Don’t worry, it’s all just a bit of fun for Ollie and the guys.” He pulled me close and kissed the back of my neck, before turning us both to face the side wall of the shed. I put out my hands against the wall to steady myself as Jackson started to fuck me. “Thought you two had something special, did you?” He began to speed up, and I could feel myself approaching orgasm again. To my embarrassment, I saw that Oliver was leading the other shirtless hunks over to the shed. “Oh well, time to put on a show for the guys. You want to cum?” I moaned and reached for my dick, but Jackson slapped my hand away. “Uh-uh. I want you to beg me for it.” I felt six pairs of eyes on me, as the other hunks crowded around the entrance, watching Jackson fuck me. Oliver was eyeing me as well. I thought I saw his lips move. Nick, don’t cum. He winked.
I tried to hold back my orgasm as Jackson pounded my ass in front of the other guys. My attention was on Oliver, though. Even if this was all just a game to him, if he wanted me to be a good boy and not shoot my load, I was going to do my best to please him.
“Yeah, fuck him hard, Jackson!” “Take that big cock, slut!” “Man, what a bitch!” The guys were taunting me, egging Jackson on. Except Oliver, who simply stood there, arms crossed, watching me intently. A couple of guys, the tall, pale, dark-haired one and the jocky blond guy, approached us and let their hands wander over my chest and legs. Tall guy pinched my exposed nipple and I nearly lost it right there…
“WHAT IS GOING ON HERE?”
The guys scattered, Jackson’s dick pulling out of my hole as he scrambled to get away. Oliver rushed forwards into the shed and grabbed my arm. I saw a buff bearded man in a shirt and tie was standing at the entrance to the shed.
“Oliver! Should have guessed you’d be behind this.” The man looked me up and down as I covered my still hard dick with my hands. “You all right? I’m sorry if the boys were a bit rough on you, although it looks like you had fun. But I do need them to do their jobs, so get your clothes on and get the fuck out, got it?” He turned to Oliver. “As for you, Mr. Dormand, we need to discuss your continued employment here…”
I got my pants back on. Oliver’s boss was waiting for me to leave, so I quickly slipped my arms into my now dust-covered shirt and made for the door. Oliver’s face was impassive as I left him with his boss. The door closed. “Ohhh, man, Ollie’s in serious shit now,” Jackson said. “Come on, let’s see what the big man has planned for him this time.” He put an arm around my shoulder (are we friends now?) and ushered me to the shed window with the other guys. Inside, Oliver was naked in the same spot I’d been, and the boss was slipping on a condom…”
I couldn’t let Oliver take the fall for this! After all, I’d agreed to let him fuck me in the shed earlier…
“I’m going to speak to your boss,” I said.
Jackson shrugged. “Won’t do any good, if you ask me, but sure, go ahead.”
I went round to the entrance and pulled the door open. Oliver’s boss was fucking him forcefully, one hand on Oliver’s hip. I tried not to stare at the hairy man’s nipple rings. They bounced hypnotically on his defined pecs each time the man rocked his hips against Oliver’s ass. Oliver, for his part, was moaning in time with the fuck, his eyes closed as he held onto the wall to avoid being crushed against it.
Oliver’s boss glanced at me as I stepped into the shed, not even breaking the rhythm of his fucking. “What is it now, for fuck’s sake?” he barked.
“I just… it was my fault,” I said. Oliver opened his eyes and looked at me in surprise. “Please don’t fire Oliver! He doesn’t deserve it.”
“You hear that?” Oliver’s boss said. To me, “In that case, you want to take his punishment instead?” He laughed when I hesitated to answer. “Didn’t think so.” He slapped Oliver’s ass hard, making Oliver yelp. “Besides, I reckon he does this just to piss me off and get me to punish him. Oh fuck- I’m getting close.” He pulled out of Oliver’s ass. To Oliver, he said, “Get on your knees.” He pointed at me. “You too.” I froze. “I won’t ask again. You want me to fire him?” I shook my head, then knelt on the floor at the spot where Oliver’s boss was pointing, next to Oliver. Oliver’s cock was stiff and wet with precum, and the shed was starting to smell strongly of sweat.
Oliver’s boss whipped the condom off his dick and began to stroke it hard and fast. Up close, it was an imposing nine inches of thick, veiny meat with a large, pronounced head that was slick with precum. “Aaaargh… urrghh…. fuuuck!”
Cum sprayed out of the man’s cock, the first volley of cum drenching Oliver’s face and clinging to his hair. Then it was my turn as hot, wet ropes of jizz hit me in the face and neck. Oliver darted forwards and sucked his boss’s cock into his mouth, swallowing the last of the man’s nut. He was working over his own dick as he sucked his boss’s cockhead clean, and after a few seconds I saw him buck his hips and shoot his own load onto the floor of the shed. Oliver’s boss ruffled his hair, almost like a dog owner rewarding a puppy. Then he looked at me, and sighed. “Honestly, man, Oliver is probably more trouble than he’s worth. But I can see you like him.” He picked up Oliver’s discarded boxer shorts and tossed them at my feet. “You can clean yourself up and then get on out of here.”
“You, you won’t fire Oliver, then?”
“I won’t. Now go before I change my mind.”
I quickly swabbed most of the sticky jizz from my face, then turned to Oliver, but he was avoiding my gaze. I decided it was best not to stick around much longer.
I stepped outside and let the shed door close behind me. Jackson and the others were waiting for me. “Dude, you’re the first guy who’s ever stood up to Mr. Hernandez like that!” Jackson said, as the others nodded and patted me on the back.
“Thanks, I guess,” I said. “What now? Will Oliver be all right?”
“Oh, he’ll be fine. Really. Hey, why don’t you come back at six after his shift?”
I considered my options. “I don’t know. Maybe I should give him some space? Shit, I don’t even know if he wants to- I mean, if I’m the kind of guy he…” I paused. “I heard you guys talking about me earlier. Like I’m some, some idiot who’s totally out of his league…”
Jackson nodded. “I get it. For what it’s worth… I’m sorry. Ollie can be a massive dick. Correction. He is a massive dick. I think you guys need to talk, properly. Anyway… we ought to get back to work. Come back at six, yeah?”
I really wanted to head home, shower, and process the day’s events, but I wasn’t sure I could make it back in time for six, so I found a café nearby to kill some time. The cute blond barista’s eyes darted up to my hair and he grimaced as he took my order. Oh fuck… I blushed, paid for my coffee, and then headed to the bathroom to clean up.
At least I got a table outside in the sun. I watched Oliver, Jackson and the other guys advertising their products for a while, then got bored and spent the rest of the time catching up on Facebook and email.
As six approached it was beginning to get a little colder. I saw the guys were wearing green polo shirts now, except Oliver, who was still shirtless. He’d lost his jeans and was just wearing a tight pair of green shorts and sneakers. More punishment from his boss? Judging by the size of his bulge, though, he didn’t seem to mind – and neither did the passers-by who stopped to ogle him while pretending to look at the display of gardening tools behind him. I got my check and settled it, then wandered over. Oliver saw me approaching, and waved.
“How’re you doing?” I asked.
“I’m fine, Nick. So, what now?”
“How about getting some food somewhere that we can talk?”
Oliver smiled. “Sure. Let me just get changed.”
“You don’t have to if you don’t want to,” I said, feeling particularly bold. “I mean, you look great, and it’s not that cold I guess…”
He laughed. “So you can feast your eyes on my hot bod all day like you did last week? Ha, it’s fine. I’ll just grab my bag, then.” He disappeared behind the shed. In the distance I saw Jackson wave to me, then give me a thumbs-up before he headed off towards the subway.
We got a table at Frankie’s, a local bar and grill that does great burgers.
“So,” Oliver began. “Guess I should thank you for standing up for me to Mr. Hernandez. But let me get one thing clear, okay? I can take care of myself. I don’t need your lawn boy money, and I don’t need you to ‘save’ me or anything like that. Got it?”
“Dude, he was going to fire you! I had to do something,” I retorted.
“Come on, Nick,” he sighed. “Obviously he was just saying that so I’d take his punishment like a good little employee. It was just…”
“Part of the scene… I get it.” There was a pause as we both took bites out of our food.
“Why’d you stop messaging?” I asked. “I thought you enjoyed yourself last week.”
Oliver shrugged. “Dunno. I get bored of chatting, I guess. Look, I’m not exactly boyfriend material…” He trailed off, and I let the silence linger. “It just… seemed like that was where you wanted to take things, in your messages. But I’m not… looking for that right now.”
“You’re more into spitroasting a guy inside a garden shed and then getting dicked down by your boss?”
“Yes! Well, not exactly, but… well, you had fun too, right? After all, you could have said no, but you didn’t.”
I blushed. “I just, I like you a lot.”
He grinned. “I can tell. You even held yourself back when Jackson was fucking you, just because I told you to. I like that you’re up for it. But, I don’t know, I kind of have this effect on a lot of guys. I don’t want you to… get hurt.”
I nodded. We finished our burgers, and went halves on the check.
“What now? I asked, as we stood outside Frankie’s, Oliver still just in his green shorts.
“Don’t mind. The night is young! Getting a bit chilly though.”
“Oh, I still have your… never mind.”
“My what?”
“Your hat…”
Oliver looked puzzled for a moment. “Oh! From last week. That beanie was an old family heirloom, you know. I can’t believe you’ve been keeping it all this time, you monster, Nick.”
“You want it back?” I said, leaning into the joke.
“Of course I do. Hand it over now, you fiend!”
“Not until you pay the ransom! We can discuss exactly how much you’d be willing to part with to get your beanie back.” I took his hand as we started walking towards the subway. I was glad he didn’t pull back.
“Oh, I dunno about that,” he laughed. “Maybe you’ll be the one begging for mercy as I pound your ass.”
“We’ll see, lawn boy… we’ll see.”