The first part of this story is based on truth. It is the truth that my relationship with my boss extended outside of the office. It is true that three or four nights a week we went out after work and on some of those nights got absolutely shitfaced.
My boss is a great looking guy in his early 40’s. He’s half Mexican, half British and the combination of genes made him a beautiful man. He works out pretty regularly and attracts a lot of attention, and he likes it.
There were nights where I was his wingman, getting into conversations with women of his choosing and then I’d hand them off to him. I’d head home and he’d take the ladies back to his place.
This has been going on well over 18 months. While in the office, nobody had any idea we were so close, as we were very, very careful to keep things on the up and up in front of other people, especially the Board and my peers.
So…still speaking truth here…things got way out of hand on a work trip to another state. We arrived the weekend before the conference began for some fun in the sun. We started the day relaxing on the beach drinking margaritas. Later, we spent $450 on a cabana by the pool that came with a bottle of champagne. Not only did we drink our bottle, we had other cocktails, too.
Naturally, my boss, let’s call him Scott, began to flirt with a few women as the booze loosened him up, and even me, one of the gayest faggots on the planet, was flirting with these same women.
The afternoon tab came close to $1000 when all was said and done, charged to my room at Scott’s request. While signing the bill, the cabana next to us gifted us their bottle of champagne since they weren’t going to drink it. Scott took it back to his room.
Scott had me make a reservation for dinner at the rooftop restaurant. We went our separate ways for about an hour to freshen up. When we met at the restaurant, we were both still a bit lit from all the day drinking, but still coherent.
When we’re seated, Scott noticed two of the women we were talking to in the pool were seated next to us. We slid our tables together, ordered wine and food, and continued to flirt and talk.
The dinner bill was over $1200, three bottles of very expensive wine and fine food…it all added up. Once again billed to my room.
Now it’s way past 11pm and one of the women invite us back to their room.
Scott insists we go to my room for some reason and that he’d go get the champagne.
Well, a few minutes later only one of the women show up and Scott came up a few minutes later. We’re informed the other gal drank too much and needed to lay down.
The three of us laid on my bed drinking champagne out of coffee cups. The women’s head in Scott’s lap, Scott’s head resting on mine, my head on a pillow.
Well past two in the morning at this point, I broke away from the duo and fell asleep beside them.
I was out of it…but then I was awakened. This is all still very true. I thought I was dreaming at first, but I heard a woman moaning, and at some point I realized I was not dreaming at all. I was sleeping, facing them when my eyes opened. I saw my boss’s bare ass pounding this woman from behind. She saw me looking at her but was so drunk it didn’t seem to matter.
I quickly turned around because in the moment I didn’t want Scott to know that I saw him fucking this stranger in my bed.
After he came, the two of them fell asleep, but I could not sleep at all. I couldn’t get the image out of my mind!
A few hours later, the woman slipped out of the bed and out of my room. Scott was out cold. Close to 10am, I faked sleep as Scott left my room.
About an hour later he texted me to meet him for a cigarette and breakfast. I showered and shaved and was very hungover.
I was very quiet and Scott asked me what was wrong.
I said I was a light sleeper and saw what happened with him and that woman.
My boss was mortified and tried to act as if she initiated and that he “didn’t finish”. That’s not at all what I heard, but I didn’t say anything.
Ok…so now this is the part that is all fiction, sort of. The truth is I have a major crush on my boss, who is very straight, and still the truth is that I’ve lusted after him since the day I met him, and I was always jealous of these women he bedded and wished it was me he was taking home and banging.
Now I possessed damning information about my boss and if our Board ever found out, he’d surely get fired. It’s one thing to go out drinking with a direct report, but the level of what happened at the conference was something more extreme. Fucking a woman in the same bed as your direct report takes things way beyond professional.
Surely, I needed to use this to my advantage. I was hell bent on making some of my fantasies become reality.
Scott and I went out after work about a week after the conference as we usually would. He’d never expect what I had planned for us that night.
We started with a couple rounds of cocktails.
“That was a crazy weekend, wasn’t it boss?”
“Yeah, it was. We had fun though, didn’t we?”
“Oh yeah, for sure. I can’t say I’d ever seen any of my prior bosses fucking someone in my hotel room, let alone in my bed.”
Scott looked at me funny.
“Did it really bother you?”
“Well…no…not me so much, but you know who it would bother, Scott? It would bother Bob, our Board Chair. I’m sure if he ever found out that wouldn’t be good for you.”
“Are you saying you’re going to tell him? I thought you were cool. I thought we said what happens in Florida stays in Florida. What happened to that?”
“Look, I’ve had some time to think, and I don’t think I can keep this a secret. It’s pretty bad and you know, honestly, I can’t get the image out your bare ass out of my brain.”
“Ok, ok, I’m sorry. I really am. Can’t we just forget about it? What would it take? You want a raise? I’ll give you a raise!”
“Scott, you can’t just give me a raise without anyone noticing. That won’t work.”
“I guess not. So what is it that you want? Just tell me and stop playing games.”
“I’ll tell you, but I’m not sure if you’ll do it.”
“Try me.”
“Ok. I want you to fuck me.”
“What did you just say?”
“I said I want you to fuck me.”
“I’m not gay!”
“I know you’re not gay, but that’s what I want. One fuck and you’ll never hear me utter another word about you fucking that woman in my bed ever again.”
“When do you want this to happen?”
“Tonight.”
“But what if I can’t get hard?”
“I’ve got something for that.”
“You’re a sick fuck man, I didn’t think you were like that.”
“And I didn’t think you’d fuck a woman on my bed so I think that makes us even Scott. Don’t you think?”
“Fuck you!”
“Yes, that’s what I want.”
“So if I fuck you tonight, you won’t say anything? You promise?”
“I swear on my father’s grave. Not another word.”
“Fine! Let’s go.”
“My place?”
“You think I’m gonna fuck you in my bed? No fuckin’ way!”
Scott drove us to my place and he was very, very angry. Driving through stop signs and red lights, speeding through town.
I couldn’t believe I was actually doing this. I opened my front door and let Scott inside.
“Sit down. I’m not going to hurt you.”
“Fine.”
“Let me get you a drink”
I poured us a nightcap and brought it over to Scott on the sofa and sat next to him.
“So what do I do?”
“Well, I could suck your dick if you like to see if you get hard, or I have a pill if you need it.”
“Fuck! Fuck! I can’t believe I’m going to say this but let’s try you sucking my dick and if I don’t get hard I’ll take the pill.”
“Sounds good to me boss. Take off your shirt and pull down your pants. I want to get a good look at you.”
“Fucking pervert! I bet you planned this all along. Acting like my best friend when the whole time you wanted this! I should have known, all you faggots are alike.”
I disregarded his commentary and watched him disrobe. He was only wearing black boxer briefs when he finished ranting. Sitting on my sofa with a defiant look.
“I can’t suck your dick like that Scott. I need to see your cock.”
“Fucking pervert! I can’t believe I’m going through with this!”
Out flopped a fairly hefty piece of meat. Uncut, nice girth. It even appeared half hard.
“Well, that’s a great dick boss. I bet the ladies love it. Don’t they?”
“Can we just get this over with?”
“Oh. I see. You’re eager for me to put your dick in my mouth. Yeah, I can do that for you.”
I was enjoying this way too much. Seeing my boss, the ladies man, giving in to me, because I yielded the power over him now.
My boss growled in anger as I kneeled between his legs. I looked up at him. His head in his hands, eyes closed as I sniffed around his crotch. He manscaped his groin and even shaved his balls, quite the metrosexual.
His musk smelled amazing as my nostrils flared wider. Then I licked his balls, a good swipe across them. Once, twice..a third time. I teased him.
Scott’s face was tight, eyes still closed when I opened wide and placed one of his egg-sized nuts in my mouth, gently sucking on it. There was no protesting now.
“What are you doing?”
I didn’t answer, I just switched to the other orb.
“Nobody’s ever sucked my balls before”, he hissed.
Well, now I just had to get them both at once. I unhinged my jaw further, using my fingers to push them inside and I used my tongue to wash them.
“Ohhh fuck! Fuck!”, Scott shouted.
I could see Scott’s shaft growing above my eye line, betraying him.
I pulled mouth from Scott’s balls.
“I guess you liked that, huh?”
Scott opened his eyes and I swear if looks could kill, I’d been dead. He was not at all happy with himself or with me.
I took his thick eight inches into my hand and gave it a good squeeze.
“Yeah Scott. I always thought you were hung, what a great cock you have. Now I can see why Maria was moaning in my bed fucking her with this bad boy.”
“Fuck you!”, Scott retorted.
“Yeah, we went over that already. I’m going to get to that in a minute, but first I gotta sample the goods.”
I opened wide and deepthroated my bosses fuckstick down to its base, holding it there for a couple of seconds, my throat spasming over it.
When I dislodged it was coated in slime.
Scott’s expression was one of amazement, his lips forming a big “O”.
So I did it again. Only this time, Scott’s hands pushed my head down over his meat.
I had to tap out when I couldn’t breathe.
“Fuck! Fuck!”, Scott was fighting his impulses while I regrouped and went down on him again.
Once again his hands pushed the back of my head down on him.
We did this quite a few times. I buried my face on his cock, his hands pressing down. His crotch was wet, messy, full of goo, as was my face.
When I tasted pre-cum I knew it was time to move from oral to anal.
“How you doing over there, Scott? Looks like your cock enjoyed it, huh?”
It was raging!
Scott actually spit in my face in annoyance.
“I’m not a faggot man!”
“Nobody is saying you are, Scott. A mouth is a mouth. Your cock can’t tell the difference, but I’m guessing no woman has ever swallowed your cock like that before. I’m right, aren’t I?”
“Fuck off faggot!”
“Not quite yet, the fun part is just beginning.”
“Can’t you just suck me off? I don’t want to fuck you!”
“A deal is a deal Scott. You agreed. Now I can tell your heart’s not into it because your dick is deflating. Let me fluff you back up.”
I took his cock in my hand and bent over to suck him some more. No protesting now. Scott seemed to like my mouth on his dick,
It was once again at full mast. I savored the sweet flavor of his semen oozing out of his piss slit.
Convinced it was time, I stood and pushed my pants and briefs down to my ankles and bent over the sofa. No live was needed, I made sure if that.
Scott reluctantly stood behind me. I reached back to grab his hardon and pulled it flush against my balloon knot.
Scott didn’t hesitate to push it on right through.
“Ohhh fuck!”, I yelped. “Wait a second!”
“No! You wanted to get fucked, I’m going to fuck you good!”
Scott grabbed hold of my waist and his inner beast surfaced. He pounded my hole over and over again, grunting and growling, clearly venting his frustration, anger, and rage. I was breathless, that big dick brushing my prostrate repeatedly, causing my own cock to ooze.
“This what you wanted faggot? My dick up your ass?”
“Fuck yes!”
Scott swatted my ass with the palm of his hand.
“I should have known. Fucking faggots only want one thing!”
Scott doubled down now, upping the pace and the ferocity.
“You better take it all in now faggot because I’m never doing this again!@
Scott continued to plow into me and I couldn’t hold my nut. My hot boss was actually fucking me! It was surreal. His head of his cock scraped my love almost perfectly and lost it. I didn’t even touch my cock. My balls exploded over my leather sofa. My body tensed and released.
When my orgasm subsided, my asshole was gripping down on Scott’s cock with a viper’s grip. I felt his big dick convulsing inside of me and a sudden sticky warmth followed.
The breeding was quick.
Scott pulled his dick out of me.
“Not a fucking word faggot! You hear me!”
I nodded my head and watched Scott put his clothes back on in a hurry.
“Not one fucking word about this or Florida to anyone!”, he yelled as the door slammed behind him.
I finally pried myself up to lock the door and clean my mess. Then I stripped and went to bed, my finger exploring my wet and seeded hole, feeling the small gape Scott left.
I was so aroused, my cock was brick hard.
I closed my eyes and stroked until I coated my chest with a fresh load.
That’s when the reality of what happened hit me and I knew that there was no way I was going to keep my mouth shut. I was going to hold it over Scott’s head again and again, each time demanding more of his big beautiful dick.In
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