I never imagined in a million years my boss’s cock would end up buried and pumping jizz up my ass, but the improbable happened one drunken night, but let’s go back to how it all started.
Joe, my boss and new CEO, started working with me a little more than a year ago. The first time I ever had a boss younger than me. Joe is married to a woman, and has had two failed marriages previously. In our industry, it is common for CEO’s to move around the country, and Joe’s previous wives didn’t seem to care for that. This new job meant Joe would be moving to another new state yet again, and wife number three hasn’t joined him, essentially leaving him a bachelor.
Joe is in his early 40’s, in great shape as he is a bit of a gym rat. Most people describe him as very good looking. Six feet tall. Dark hair, short cropped beard, endearing brown eyes. The man is a catch, makes lots of money, and quite successful professionally.
Joe and I started off slow in terms of our professional relationship. Meetings were always high level, professional and cordial for the first three or four months.
One day Joe asked me if I’d be interested in going for a drink after work. I said yes. That night, one drink lead to another and then one more and it was great to see Joe let his guard down. We immediately hit it off and our after work drinking nights became more frequent and there were many nights where three or four different bars were patronized and our nights ended after 2am.
All the while, Joe hadn’t stopped frequenting the gym and his muscle gains were more noticeable. Joe’s suits were becoming tighter as his muscles strained to stay contained in them.
It was nearly midnight one night and we ended up back at his luxury apartment for a last drink before calling it a night.
Over all these months, I tried very hard to control my attraction to Joe, never once showing any sexual interest, as he was my boss at the end of the day, and I never wanted to cross that line. That particular night, I lost control and I guess my seductive glances gave me away.
“Are you checking me out?”
“Ahhh, no. No, I’m not.”, I said rather unconvincingly.
“Yeah, you are. It’s ok, you don’t have to hide it. Have you noticed I’m getting so big? I can’t even fit in my clothes anymore.”
“Yeah, I have definitely seen a difference.”
Joe walked over to where I was standing by the kitchen counter and flexed his biceps right in front of me, wearing only a deep cut black v-neck.
“Feel my muscles if you want. I don’t mind.”
I didn’t know how to respond to this offer. Of course I wanted to, but this hot guy was still my boss.
“Come on, feel ‘em”, he insisted.
I took a swig of the vodka & tonic and gently squeezed the grapefruit sized muscle of his right bicep.
“You see? It’s huge, right?”
“Yeah”, I gulped, thankful I wear a chastity cage to contain my little wiener.
“Feel my other one.”
I did the same, impressed with its size and firmness.
Joe took a swig of his drink and was slightly stammering.
“You wanna feel my pecs?”
“Huh?”
Joe was definitely out drinking me, and had been all night. I was still sober enough to know that what was happening wasn’t exactly appropriate, but I don’t think Joe was sober at all.
Joe pulled off his shirt and threw it across the room.
His chest was beautiful. His tanned chest had a sprinkle of hair on the breastbone and a smattering that trailed down to the waistband of his pants. Those pecs were huge and his nipples were the size of nickels with both fully hard and erect fully on display.
Joe took my hand in his and placed it right on his chest, rubbing it over each pectoral muscle.
“You see, working out has really paid off. Don’t you think?”
“Ahhh yeah”, was all I could think of to say as I was still in disbelief that my hand was touching my boss’s naked chest.
Finally he let go, and I looked at my watch. It was nearing one in the morning in a work night.
“Hey Joe, I think I should go. It’s getting late and I have to drive home.”
“Yeah, ok”, he said.
I only lived 10 minutes away, but I didn’t want to get pulled over by the cops.
I had a difficult time sleeping that night as I laid in bed in my briefs replaying how awesome my boss’s muscles were and how I got to touch them. I wondered if he’d remember or say anything the next morning.
Sure enough, our paths crossed in the late hours of the morning by the coffee station.
“That was fun last night”, he said.
“Yeah, it was”, I said.
“I’m glad you got to come see my place.”
“It’s very nice.”
“We could hang out there tonight and take in some dinner, stay over if you like, this way you don’t have to worry about driving. I have two spare bedrooms.”
“Are you sure? I mean, I don’t live that far.”
“No, but I felt bad you had to drive. It would make me feel better if you didn’t drive and I like hanging out with you.”
“Ok, I’m down.”, I said.
I happened to have my gym bag in my car with some shorts and toiletries, so I was all set, figuring I’d go home in the morning to change for work.
That night over dinner and drinks, both of us in gym shirts and tank tops, as it was late summer, Joe told me he hadn’t been laid in almost four months and how much he missed having sex.
Joe asked me about my love life. I was not too sure how much to share as my sex life was full…my keyholder Jace, my Sir, William, and other regulars that fucked and fisted me.
“I get my fair share”, I said.
“You gay guys have it easy. Sex is part of your culture”, Joe said.
“I don’t know about that. I guess I just have different guys for different needs.”
I found myself opening up more with each sip of alcohol.
“Can I ask you a question?”, Joe asked. “Why won’t you go to the gym with me?”
It was because of my cage, I wasn’t prepared to tell him that.
“Because look at you and look at me. I can’t compete with you.”
“No…I don’t think that’s it. I can tell you’re hiding something. Just tell me. I’ve told you so much now it’s your turn.”
Oh Lord. Wait, I think I need another big sip of this drink before I tell you.”
I took a huge swig and put down the glass.
“It’s because one of the men I see has the key to the cage I wear over my junk, and the last thing I wanted was for you to see it.”
“Wait! Wait!! Seriously! That’s why? Are you wearing it right now?”
“Yes”
“No way! No fucking way!”
“Yes way. I’ve been wearing it almost every day for an entire year.”
“I don’t believe this! You mean, you haven’t jerked off once all year?”
“Well, I have maybe once or twice when Jace lets me.”
“Jace?”
“Yeah, my keyholder.”
“That’s crazy! Here I am telling you I haven’t fucked a girl in four months and this whole time your dick has been locked up. Does this mean you’re always the bottom?”
Oh my…this was getting deeply personal now.
“Yeah, I guess.”
“I can see that. You are very submissive at work. Don’t get me wrong. You’re amazing at what you do, but sometimes you let your peers walk all over you. Now I can see why.”
I didn’t say anything. Neither did Joe.
He cleared our plates and brought us two more drinks. He turned on some music and we retreated to his living room.
“I’m getting hot”, Joe said as he pulled off his tank top. There he was, a second night in a row, shirtless, right in front of me.
“You think I look hot?”
“Yeah”
“You think if I end my marriage another girl will love me?”
“Yes, of course, look at you.”
“I’m a good catch. I’m smart, I’m rich, I am sexy. You’re probably right, I could probably go get laid tonight if I wanted to.”
“For sure.”
“When’s the last time you got laid?”
Joe wasn’t shy. His hand covered his crotch in his tight gym shorts.
“Last Sunday.”
“Was it Jace?”
“Yeah.”
Tell me about him.”
“He’s Black, 48 years old, construction worker, built hairy man, bald, beard, and a really nice package.”
“I guess he sounds hot if you’re a gay guy.”
“He’s very hot.”
“How long you know him?”
“About ten years.”
“That’s nice. I miss my wife, Richie.”
“I know, Joe. I’m sorry. I wish I could make it better for you.”
“You have. You’re here keeping me company.”
“I’m glad I could help.”
“Remember last night?”
“Yeah”
“Did you like feeling my muscles?”
“Yeah, of course.”
“You wanna do it again?”
“Do you want me to?”
“Yeah. I need to be touched.”
“Ok.”
This time I walked over to where Joe was, only he stood up and hugged me tightly. His hands caressed my butt and then he let go, took my hand and placed it back on his chest.
Even after he let go, I didn’t stop admiring his muscles, and even took my other hand and slowly rubbed his chest. Joe then flexed his arms for me and each hand had the pleasure of muscle worship.
Joe surprised me when his hand took my right wrist and placed it right on the hard brick between his legs.
“Joe, what are you doing?”, I asked.
“Do you mind? I mean, I’m so fucking horny, Richie. This is more action than I’ve had in months and I’m tired of using my own hand.”
“No…I guess not. It’s just, you’re my boss, and I don’t want it to get weird between us.”
“Don’t you think we’ve already crossed that line? At this point it makes no difference if you touched my chest or sucked my dick .”
I pulled away from Joe.
“Sucked your dick?”
“Yeah. Isn’t that what you’re into?”
“Yeah, I am, but not with my boss.”
“Forget about that. Just stay here for a minute.”
Joe walked back in the room completely clothe-less. His uncut cock was nearly seven inches and hard as fuck. It was nice and thick, too.
“You like to party, Richie?”
“Yeah, I guess.”
“I thought so.”
Joe laid out a couple of lines from a small vial on his glass coffee table and he took two and took one.
Then he carefully laid out another one for me across the length of his cock.
“Yeah, you know you want it, do it.”
I kneeled and snorted that line and looked up at my boss. The drugs were quick to act.
“You can suck my dick now”, he said.
I was flying high, opened my mouth and gave Joe one hell of a blowjob, showing off my deepthroating skills.
It didn’t take long for Joe to feed me a mouthful of cum which I swallowed eagerly.
“Oh fuck, Richie, you have no idea how much I needed that. I can see why Jace keeps you around. You suck dick like a Hoover. Probably the best blowjob I’ve had in my life.”
“I’m glad you liked it”, still glowing from the chemicals, alcohol, and cum, and bewildered by it all.
Now that we were both wired, Joe and I drank another round, and we were dancing and singing like two idiots. I was stripped down to my briefs and Joe had slipped his shorts back on.
“Hey, can I see it?”
“See what?”
“You know, your cage. I can see it bouncing around in your underwear, but I want to see it for real.”
I pulled down my briefs and there it was in all its glory, my black Cobra cage.
“Can I touch it?”
“Yeah, I guess.”
Joe timidly reached his hand out and tugged on the cage a little bit.
“I’ve never touched another man’s junk before. I guess this is the closest I’ll ever get.”
“Oh”, I said foolishly.
“Your cock is pretty small, is that why you keep it locked?”
“No, I just like the way I feel when I’m locked.”
“Keep your underwear off, ok? I wanna see it.”
“Ok”
Joe played another song and we both danced again, my covered dick cage flailing about.
When the music stopped, it was late, and the coke had warn off, and we were both pretty tired.
So we went to bed, in separate beds that night.
Over the next weeks, more sleepovers, more muscle worship, more blowjobs. It was all good fun and as strange as it seemed, we were all business at work and I don’t think anyone suspected I was blowing the boss.
One detail I left out is that by week three, I was no longer sleeping in a spare bedroom, I was sleeping in the same king bed as my naked boss. I’d also been being work clothes to his place so I didn’t have to wake up super early to change.
This was by no means a nightly arrangement, but definitely two to three nights a week.
Now we can forward this story to last night. We had eaten out, bar hopped, and took things back to his place. More drinks, a bump or two of coke, and the awkwardness between us, if there was any left, was completely gone.
There I was in mid blowjob, on my knees in his bedroom, when Joe pulled me off his cock.
“Hey Richie, stand up, ok?”
I did
“Everything ok?”
“Yeah, hey, you know I’ve really been thinking about fucking you.”, Joe blurted.
“What? Seriously Joe?”
“Yeah, I gotta tell you, I’d been thinking about this guy Jace you go on and on about, and thinking you must have a great ass if he keeps wanting to fuck it for ten years.”
“Is that right?”
“Yeah, so I thought, why should he be the only one fucking your ass? I need to get some of that, too.”
“So you wanna fuck me tonight, like right now?”
“Yeah.”
“But I didn’t plan on it, I mean I’m not sure if things are ready back there for this?”
“Funny you should mention that. I googled how gay gays get ready for fucking and I bought you a couple of Fleet enemas. They’re in the bathroom under the sink.”
“So you e really been thinking about this then?”
“Yeah, for a couple of weeks.”
“Really?”
“Yeah, now go clean out because I wanna fuck you while I’m still buzzed.”
“Yeah ok.”
Now I was in my boss’s bathroom, douching for his dick. This was insane! I wasn’t in my right mind myself as I was doing this, and when I felt I was fully ready, I returned to the bedroom.
Joe was lying back, stroking his hard dick.
“You ready?”
“Yeah”
“Come here.”
Joe laid out another bump across his chest and after I snorted it, I sucked his dick again. Now my ass was hungry.
I positioned myself on all 4’s.
Joe prepped a bump right over my ass. First he costed his cock with lube, then he took the bump, next he impaled me with his cock. With the assistance of the chemicals, my hole showed no resistance, and Joe was balls-deep up my ass.
“Fuuuckkk, Richie! Ohhhh man! Fuck, this ass is fucking great!”
Joe was pretty high and ready to fuck my brains out.
His hands grabbed me by the waist and he just started pounding away. My small caged dick was once again swinging about as I gave up my ass to my manager, the man who would be responsible for my performance reviews at work.
“I’m not gonna last too long, man. I haven’t fucked anyone in six fucking months! Ohhhh damn! This ass is fucking awesome!”
Joe slammed into me for another minute or two, declaring my ass was better than his wife’s pussy, better than any pussy he’d ever fucked.
It all came to a quick and sudden crescendo.
“I’m fucking cumming, Richie. I’m blowing my nut up your ass!” Ohhh holy fuck! Ohhh fuuucck!”
Without dislodging his cock from my asshole, Joe maneuvered us so that he was spooning me. I felt his warm breath on my back as he found slumber.
I was wide awake, still in shock that I’d been fucked by my boss!
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