Lifeguard on Duty

I’m very excited to say that at least the first part of this story is completely based on a real experience that I had, and I’ll let you guess where it transitions into fantasy…

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New to the company, I had almost steadfastly decided to skip the spring gala that was held every year, but my new coworkers told me that I couldn’t. There would be free booze, a chance to schmooze with drunk higher-ups, and most importantly, the office shut down at noon to let everyone get home before the Friday traffic to get ready. Not really a huge drinker, that last point sold me, and I agreed.

My reluctance to go was just based on nerves that came with starting any new job- I actually truly was really happy with my new position. Everyone on my floor had been so welcoming, and the workload seemed lighter than expected for my salary. Once I’d finally bit the bullet, I began to get excited as I went into my closet to grab my navy suit. It fit me just right, a little too right in some places. A bit too tight around my ass for the office, it would be perfect here to see if anyone was interested in getting to know me better. Ditching the tie, I kept the first button undone before flicking open one more. My tanned skin contrasted the crisp white shirt, and I felt a bit too daring, but I went with it anyway.

Grabbing my car, I drove over to the event center and found an almost empty parking lot. I was a bit nervous that I’d gotten there too early, but as I stepped out, I heard the cacophony of voices and music spilling out of the building next to me. Walking inside, I realized that the lot was empty because most of the people here expected to be too drunk to drive home. I’d planned to keep my wits about me, and I grabbed a drink at the bar that I’d nurse for the whole night.

This venue had been listed on the invitation as a run of the mill event center, but it was actually a converted club that hadn’t converted too much. The dance floor was full of people in business suits doing the Cha Cha Slide, and in booths around them, some coworkers were already sliding into their first or second bad decisions of the night. Out back, a fake-candlelit hallway led to the tables overflowing with food, and behind that, there was a door to a courtyard with high walls blocking it from neighboring buildings.

Out here, only a few small groups milled about, and right in the back, there was an honest to goodness pool. It was long and narrow, and I’m sure in the club’s heyday that it had been full of bikini-clad women tossing beach balls and enticing the guests. Now, it was empty except for one man standing next to the lifeguard chair. He was wearing a pair of floral swim trunks that exposed his thick, tanned thighs. Up top, he was wearing a white blazer with what appeared to be no shirt underneath. A thick crop of trimmed chest hair was all I could see between the lapels. He had on aviator sunglasses, a sunhat, and on his feet, sheer socks high on his calves with a pair of wing tipped loafers. He was devilishly handsome, and he was one of my bosses- Robert Owens.

Smiling at me as I walked up, we shook hands, and I felt his firm grip send shivers down my spine.

Glad you make it, Russ. Great party, isn’t it?

You guys have blown my last company out of the water. Taking another sip of my drink, we stood there and watched an accountant stumble outside, make eye contact with someone, and run back in without a word.

They used to fuck, but it ended badly.

Hearing Rob chat so cavalierly shouldn’t have fazed me, but this conversation seemed more relaxed, more personal than one we’d ever had before. At least in real life- inside my head, I’d fantasized about much naughtier conversations…

So, how did you get stuck being a chaperone out here?

I had to change the subject if I was going to keep myself from fantasizing again.

Every year, the exec team pulls straws, and two people are chosen to be babysitters. Darlene is inside watching everyone, and I got outdoor duties.

And the outfit?

That’s all me, baby.

Grabbing onto his blazer, he flashed me that smile again, and I was sure now that there was no shirt on under there. I knew that he was my boss and could bend the rules, but this seemed a bit too far… guess it was good to be the son of the company’s founder. I’ll use my privilege too and see if being new allows me to be more daring.

The blazer looks nice, but I’m sure it’s too expensive for me. What about the shirt though? Maybe I could afford that.

Rob either knew what I was doing and playing along, or maybe he was as dumb as everyone said. Smirking again, he just unbuttoned his blazer and pulled it open to show that I could easily afford the shirt. His toned chest had the faintest hint of those abs that had earned him a baseball scholarship back in college, and the chest hair extended all the way to those swim trunks that seemed to rest a little lower than appropriate.

You know- it is getting a bit hot out here, don’t you think?

Turning around to see who else was getting a free show, I saw that the courtyard was actually empty now- this was Darlene’s problem inside now. As I spun back around, I saw that Rob had ditched his blazer and was standing half-naked in front of me. This was crazy- anyone could walk outside right now and see him, but he didn’t seem to mind. He also seemed ready to go swimming too as he bent down to begin taking off his shoes, but he got into the water earlier than he expected. Slipping a bit as he reached for his laces, he went tumbling backwards into the pool.

It was definitely not deep enough for diving, and as I threw off my blazer to go in after him, I luckily saw him surface, laughing as he wiped water out of his eyes. Pushing his hair back, he looked even sexier as he splashed me with water, plastering my already tight shirt against my chest. The cool water had my nipples hard instantly, and I imagined his mouth around them before I shook myself out of that fantasy.

I know you’re my boss, but can I also call you an asshole?

Only if I’m being really bad. Everything he said was dripping with sex, and as he got out, he stood there just looking like sex as well. C’mon, there’s a little bathroom tucked away in the corner.

Walking behind him, I stared at the thin material practically glued to his beefy ass as he walked over to a gated area in the corner. Behind it, there was an outdoor shower and a cabinet filled with towels. Grabbing one for each of us, he began toweling off as I tried to dry off as much as I could.

That shirt is a lost cause- you should just hang it up and let it dry for a bit.

He pointed to the air conditioning unit tucked away in the corner that was pumping out warm air, and I just stood beside it, hoping that that could work.

Oh, no need to be shy now. You’re not the one who just embarrassed themselves and fell in the pool.

Walking over, he began reaching for the buttons on my shirt, and I was too stunned to even stop him. This was going further than some of the dreams that I’d conjured up, and I just focused on keeping my breathing under control as he pulled open the last button on my shirt. Hanging it on a spare hook on the wall, he just kept drying off as if he wasn’t turning me on within an inch of my life. Holding the towel in front of me, I wasn’t sure if I was hiding my chest or the bulge in my pants. Turns out, I wasn’t effectively doing either.

Oh drop the act, Russ- those suit pants aren’t dark enough to hide the hard-on you have for me.

I was rooted to the spot as I tried to process what he’d just said, but my brain wouldn’t even work as I stared forward as he reached under his towel to pull his wet shorts down. Standing there in nothing but a towel and a smirk, he stepped forward but was interrupted by a surge of crowd noise coming outside. In a high pitch voice, I heard Darlene complaining about where Rob was. With his voice against my neck, he whispered that I had to go out there.

Reaching down, he began slipping my pants down, but not for the reason that I wanted. My briefs joined them next, and my breath caught in my throat as I wondered whether he’d seen my cock or if he was too focused on pulling his discarded swim trunks up my legs.

The cold fabric chilled me to the bone, but the goosebumps popping up on my arms again were because I was realizing that his cock had just rested where mine was now.

Go get ‘em, tiger.

With a slap on my ass from him, I stepped towards the gate in nothing but borrow swim trunks.

Where the hell is, Robert?

He had an urgent phone call to take so he conned me into being a lifeguard.

And why are you wet?

Couldn’t resist, I guess…

They had no idea that I wasn’t talking about the pool, but they were too drunk to notice. For the next hour, I stood shirtless in front of my coworkers as they got a little handsy, but all I could think about was disappearing back behind that gate once the party was over. I wouldn’t mind getting the seats in my car wet if that meant that Robert was sitting in it…