Best Job Ever

This story is a bit silly, but it was inspired by this tweet: This just gave me an idea for a short story. I’ll have to pound one out tonight… #cucking #gaycucking #gayerotica https://t.co/BwrbSwPDV4— Hadrian Temple (@HadrianTemple) July 21, 2019

“Ross.” Kevin’s voice was just loud enough to reach the spot where we bellhops hung out next to the reception desk. 

“Man,” grumbled Alan, “why you?”

As I stood up, I turned toward him and shrugged my shoulders. “When you got it, you got it.”

“He’s just saving me for the next Gold level guest.” The Gold Levels were guaranteed special attention from check-in to check-out. I wonder if he’s ever gonna figure out that Kevin’s getting a cut of my tips?

I closed the distance to the check-in counter and smoothed out my outfit to make a good impression. I was wearing snug black chinos and a black polo with yellow detailing, including the resort’s logo, “Cuck Hold Resort” in the shape of a pair of bull’s horns. The shirts were very stretchy, so I wore a size smaller than I normally would. It showed off my definition really nicely. The owner, Mr. Garcia, wanted us showing off our bodies. He only hired guys who could pull off the look he wanted. 

At the desk, Kevin gestured to two men who had obviously just checked in. “Ross, could you take Mr Mueller and Mr. Richinski to Cabana 14?” Then, to the guests, “Ross will make sure you get settled in nicely.”

I smiled at the guests and grabbed the luggage cart. One of them was probably  in his early 40s and looked like he could have been a model: tall, muscular, strong jaw, beautiful head of brown hair. The other guy looked a bit younger, mid-30s or so. He was much shorter, about 5’8 or so, and had a jockish physique. His blond hair was cut in a short, contemporary style. He looked like the kind of guy who worked out 2-3 times a week and played in a local soccer league, while his husband (they were wearing rings) clearly spent twice that much time at the gym. He was ripped

This was gonna be a bit tricky. Which one should I play up to? Usually I went after the younger, more athletic guy, but with this couple, the older guy was clearly much more fit than his partner. They were dressed casually, so I couldn’t even get a hint about which one of them had the money and wanted the attention.

Mr Garcia was very insistent that we call the rooms “cabanas”. He said it sounded more Caribbean. But in reality, the whole resort was one large building, with three blocks of rooms arranged around a central courtyard that held a large swimming pool, a hot tub, a bar, and a couple other amenities. It was landscaped with trees and plants that did well in the Miami heat. It was clothing-optional, so a majority of the guests were somewhere between skimpily dressed and not dressed at all. During the daytime, there were a fair number of guests enjoying the pool, the lounge chairs, and each other, but it was in the later evening that the courtyard really got hoping.

As we passed through the automatic doors from reception into the courtyard, I took a moment to look at Jock. “I hope you enjoy your stay. We’ll do everything we can to make it memorable.” Then I looked at his husband and winked. When in doubt, split the flirting

Jock said, “I’m sure you will. I’ve heard good things about this place.” His partner said nothing, and that told me which one I needed to focus on. 

I looked Jock in the eye. “We aim to please.”

A few moments later, I pulled the luggage cart up to ‘Cabana 14’, and swiped my key card to get in. I grabbed their two suitcases off the luggage cart and pushed the door open. Every suite had a different theme. Number 14 was decorated in browns and greens, with scenes of shirtless farmhands and shepherd boys frolicking immodestly in some bucolic countryside. Jock and Model followed me in and let the door swing shut.

Now that I knew which guy to focus on, my second issue was how to play things. Some guys wanted us to be aggressive, while others preferred to treat us like slabs of meat. This wasn’t some abstract issue. The pay was crappy, barely above minimum wage, but if I played things right I could expect very generous tips. I’d had several $1000 weekends this summer. Good money for a guy who hadn’t graduated from college yet. In contrast, I don’t think Alan had gotten much about $500 in a weekend. That was because I was much better at figuring out exactly what the guests wanted. Well, that and my arrangement with Kevin.

I set their bags down and spent a minute pointing out all the features of the suite. I didn’t have to do that, but it gave me a chance to make a lot of eye contact with Jock. Is he Mr. Mueller or Mr. Richinski? 

There was a large window that looked out onto the courtyard, with a curtain that could be opened or closed depending on how much privacy the guests wanted. “Honey, “ said Jock, “could you open the curtains please?”

“Sure thing.” Model’s voice was a sexy baritone. But Jock seemed to be calling the shots. The room lightened up as his opened the curtains. 

“If you need anything, don’t hesitate to call and ask for me—Ross.” I was trying to sound casual, but I looked Jock straight in the eye as I said it. 

He pulled a pair of twenties out of his wallet and pushed them into one of my front pockets, taking the opportunity to run his hand over my crotch for a moment. Then he turned around and said, “Oh. Ross, before you go, could you help me off with my shirt?”

“Sure thing, sir.” I still wasn’t sure how he wanted me to play this, so I defaulted to being respectful. I slid my hands under the back of his shirt and then reached around to the front side before I started pushing the shirt up. He just raised his arms and let me run my hands over his chest as I slowly pushed the fabric up. As his shirt came over his head, I made sure that I leaned in and breathed gently on his neck. He made an appreciative noise and pressed his body into mine. So that was how he wanted it. He wanted to feel a bit ravished. 

Model was watching us, but I ignored him and acted as if it were the most normal thing in the world to help a guy undress in front of his husband. With the t-shirt out of the way, I said, “Let me help you off with your pants.” 

Making sure I was engulfing him with my arms (since I was about 5 inches taller than him), I undid the belt on his shorts and then opened them up. They fell down about his feet and as he kicked them off, along with his sandals, I started massaging his hard dick through his snug underwear. 

Were these guys hothusbands or was Model a cuck? Until I started working here, I had never heard about either idea, but it made a different. If Jock was a hothusband, Model was probably going just to have fun watching us fuck; he was a spectator more than a participant. But if Model was a cuck, he wanted humiliation more than fun. Good tips required me to figure this stuff out fast. Alan was clueless about a lot of this.

Jock started grinding his ass against my crotch, and was clearly enjoying the fact that I was hard. I’m not the best-hung guy at the resort (that’s Shawn; dude’s 9-incher was very popular), but I had six thick inches and rarely got any complaints. I grabbed his hips and ground into him aggressively. “I’ve been needing some pussy for a while now, and I think I’m gonna choose yours.”  I’d learned that the guys who wanted me to be aggressive liked feeling like this was about my pleasure, not theirs. 

I spun him around and pushed him down to his knees and then pressed his face into my groin. He gnawed at the fabric of my chinos. I groaned for effect, as if I had a long pent-up supply of lust he was releasing. (In fact, one of the guests had blown me about an hour before.) I pulled my zipper down and freed my dick. I generally went commando at work. He opened his mouth and swallowed my cock down, although it was thick enough to be a struggle. 

It was starting to become clear what I was dealing with here. I looked down at him and grinned. “You don’t get that at home, do you?”

He made a muffled noise around my cock, and then pulled off me for a moment. “Never! He’s tiny.”

I looked over at Model. His face was getting red. “Is that so? Is that why you work out so hard? To distract from what God forgot to give you?” It had taken me a while to find the boldness to speak to guests that way, but once I learned to do it, I discovered that it often got me a huge tip.

Model nodded meekly. 

“Let’s see it.” He hesitated, so I said, “Look, if you could satisfy your man, he wouldn’t be going to town on me. So don’t bother trying to hide it.”

Model unzipped his shorts and pulled out his cock. It was small, maybe two inches. It was kind of lost in the fabric of his fly. 

“Aw, man, “ I said to Jock, “now I see why you’re so desperate. Your husband doesn’t have anything worth calling a cock, does he?”

“God, no.” I could tell he didn’t want to stop sucking, so I let him keep going, all the while grinning at Model, who couldn’t stop watching. 

But after a few minutes, I pulled Jock up from his knees, spun him around and bent him over the bed. He had a nice ass, firm and round. Dude clearly had a lot of lunges in his workout routine. I yanked his underwear down and fingered his hole. He moaned. “My finger is better than your cuck’s dick, isn’t it?” He groaned in agreement and kicked his underwear off so he could spread his ass for me. 

“Hey, cuck, get over here. Your husband’s ass needs to be prepared for me to fuck it.”

Model’s mouth dropped open. This was a trick I learned from Shawn  last month, and so far it had never failed to get a rise out of a couple. After hesitating, he moved from the window, crouched down and started eating his husband’s ass. I moved over to the night table, where there was a fresh bottle of lube. I opened it and liberally slathered some on my cock. Then I moved to stand over Model, stroking my shaft. 

“That’s right, cuck. Your man needs my dick, but your tongue can still give him something he needs.” I pushed his head into his husband’s ass. It was arousing, treating this big, muscular, model-looking guy with such contempt. But this job was teaching me just how complicated people were when it came to sex. This guy clearly needed to feel humiliated. Maybe it was because his looks intimidated people. 

While he was tending to his husband, I looked up and noticed a guest standing at the window of the cabana. He was a thin Latino guy who looked to be in his mid-30s. He was wearing nothing but a speedo, which was failing to hide his hard-on. I grinned at him. This job taught me that I enjoyed having an audience. 

I was getting pretty damn horny by this point, so I pushed Model away from Jock. “Time for a real man to take over.” Model got out of my way without saying anything and then stood up. He pulled out his cellphone and started to record what I was doing to his husband.

The staff had the option of using condoms if we wanted to, but the resort paid for PrEP. Mr. Garcia said that raw fucking was more popular, and my own experience had proven it to be true. It seemed to get me better tips. So I just positioned myself behind Jock and began pushing slowly against his ass. His ass was firm and tight, and I couldn’t help but make a loud grunt as I worked my way in. He groaned and drew short ragged breaths as he adjusted to my girth. 

“You getting filled the way you need?” I asked.

“Jesus God yes! You’re so fucking…huge!”

“Well, after micro-dick here, I’m sure anything would feel big.” I glanced over at Model, who was jerking his cock with two fingers while looking through his camera at us. The guy at the window was jerking too. 

Jock wanted an aggressive fucking and that’s what I gave him. I grabbed his hips and just started pounding away. He pulled his knees up onto the bed and spread them as wide as he could, propping himself up on his forearms. He was bearing down on my dick, clenching his ass tightly, which felt wonderful. 

I looked over at Model. I couldn’t make eye contact because of the camera, so I looked straight into it. “Your man has the hungriest ass I’ve ever fucked! He needs way more than you’re giving him. Good thing I’ll be around this whole weekend. I need a lot of ass.” I grinned my best cocky college student grin for him. He made a soft, sad gasp.

I’ve learned that this job required you to know how to perform your role as a bull, and I was playing that role to the hilt. If Jock and Model saw me as an insatiable stud bull, they were gonna be requesting me all weekend, and that was good for my bank account. So I threw myself into the performance, grunting and snorting loudly.

I leaned forward, putting my arms on the bed around Jock, so I could thrust more deeply. That apparently did the trick for Jock, because the register of his voice suddenly jumped up and he began making squealing noises kinda like my first girlfriend used to. 

I’ve learned that I really get off on knowing I’m pushing a guy’s buttons. And right now I was pushing everyone’s buttons. Jock was making all kinds of noise, his husband was furiously jerking off, and the guy watching through the window had just left a white smear across it. Right now, I was a stud bull, and it was time for the money shot. I reached around and started to stroke Jock’s dick. He made a loud wordless moan and blew his load onto the coverlet over the bed. Then I focused on myself, humping his ass as violently as I could until I blew my load as well, shooting into Jock as he begged me to knock him up. 

I wrapped an arm around Jock’s chest and pulled him up to standing. He turned his head around and I frenched him. I maneuvered his body so I could look at Model with one eye while I did so. 

After another minute or so, I broke off and pulled out of Jock’s ass. A trickle of my jizz began to run down Jock’s leg. I looked over at Model. “I did my job as your stand-in. You mind taking care of the clean-up?” Model blushed. He pocketed his camera and moved behind Jock. I couldn’t tell if he had shot a load or not. He crouched down and began lapping up the mess I’d made. I watched, wiping my dick off on one of the towels stacked next to the TV set. 

Eventually Jock stood up and looked at me. “Damn! Best room service I ever had!”

“I am to please, sir,” I said proudly. 

Jock found his pants and fished out his wallet. He pulled out two $50s and handed them to me.  “Thank you, sir! I hope you enjoy your stay. Don’t forget, if you need anything, call Room Service and ask for Ross.”

I pulled the cabana door open and walked out, pocketing the tip. This was the best job ever!

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