Gay Boss Sex Stories

GayDemon's Stories: On this page you can find erotic fiction where you can read about men forced to have gay sex with their boss listed by date.

9.4
31 Votes

Own-Me! (ch. 3)

Story by I. Dusk

11 Apr 2023 3367 Readers comments 11 Min Read

Most of the morning, I was sporting a semi under the table as I kept remembering details of that hot session in the restroom stall. . . . We came into the spacious office, and Mr. Simmons just put the phone on the table and stood up to welcome us. I, however, stood frozen in my spot, staring at him with confusion. I knew that suit. I took it off him this morning!

Topics: Cum Dump, Co-worker, Oral & Blowjobs, Domination, BDSM, Blindfold, Boss

9.6
32 Votes

My New Personal Assistant (ch. 16)

Story by I. Dusk

6 Apr 2023 2551 Readers comments 11 Min Read

But that wasn’t the worst part. I hated the fact that I couldn’t even jerk off. I thought it would be fine, and at first, it was manageable, but then, once, in the shower, I couldn’t stand it and started fingering myself, remembering him fucking me after he waxed my ass. T

Topics: Public Sex, Masturbation, Romance, Edging, BDSM, Boss, Blue Collar

9.4
37 Votes

Why Him, of All People

Story by I. Dusk

4 Apr 2023 4125 Readers comments 10 Min Read

“Hi, daddy.” “Hi… please don’t call me daddy.” I was nervous as it was. He was eyeing me shamelessly, and I felt extremely uncomfortable. Nevertheless, I let him pull me in. Checking anxiously if anyone was out there seeing us. “And how would you like me to call you?” “I am Sam. What is your name?” “You can call me boy.”

Topics: Anal Sex, Rimming, Romance, First Time, Feet, Age Difference, Lingerie, Boss, Bartender

9.3
103 Votes

Late-Night Snack

Story by Mister J

30 Mar 2023 6765 Readers comments 17 Min Read

After the last one quit, a closeted CEO hired a new personal driver. One night, while raiding the kitchen for a late-night snack, he ran into the hulking employee who offered him something to eat. Something huge with a special sauce. His wife upstairs can wake up at any time and catch them. Will he take the straight man's offer to satisfy his hunger of a different kind?

Topics: Muscle, Straight Men, Big Dick, Voyeurism, Infidelity, Face Fuck, Bear, Verbal, Bareback, Oral & Blowjobs, Married, Boss

7.0
20 Votes

Acing the Interview

Story by BiII1t

20 Mar 2023 3951 Readers comments 4 Min Read

Carmichael sets out to get his very first job at a promising corporation. He has worked extremely hard to get where he is at. However, the way he derives his confidence could also be his downfall. So maybe he should get some extra support. Nevertheless, it's only up from here...

Topics: Straight Men, Doctor, Hypnotized, Revenge, Boss

8.5
13 Votes

Full-pledged Tribute to Cock & Ass

Story by Paul François

20 Mar 2023 599 Readers comments 6 Min Read

Money makes the world go round, according to a song, but having the right guy at the right place guarantees full-blown virile fun.

Topics: Interracial, Sex, Boss, Fucking

7.6
41 Votes

Employee of the Month

Story by Blackbottomboy

15 Mar 2023 3961 Readers comments 2 Min Read

I was an freshly 18 year old senior in high school who loved doing “extra work” for the boss after hours

Topics: High School, Age Difference, Boss, Food Sex

9.1
21 Votes

William (ch. 6)

Story by jeff1

15 Mar 2023 1038 Readers comments 5 Min Read

I was still trying to get my head around the logistical dynamics here, as I sucked Anthony clean, and as Markus warmed up for the evening.

Topics: Big Dick, Group Sex, Interracial, Cum, Breeding, Gym, BBC, Boss, Cum Swallow

9.5
31 Votes

My New Personal Assistant (ch. 13)

Story by I. Dusk

7 Mar 2023 2145 Readers comments 9 Min Read

"I would buy this whole shop just to be able to rip these clothes off of you and fuck you here." he blinked, hearing that, and the vein on his neck drew me closer. "That wouldn't be a good investment." "It would be worth it to me." "I think you are now letting your dick make the decisions. That's not wise."

Topics: Romance, Co-worker, Boss, Blue Collar

9.7
41 Votes

Fiance of my Ex-Boss (ch. 6)

Story by I. Dusk

5 Mar 2023 3193 Readers comments 9 Min Read

I moved without thinking, just drawn to his lips, watching his expression as he watched me get closer. He hadn’t moved an inch, he still had his hand on my thigh, and I finally reached his lips with mine. I softly parted them as I kissed him, and my hopes were answered when his mouth opened for me, and he kissed me back.

Topics: Muscle, Straight Men, Handjob, Friends, Infidelity, Armpits, Bromance, Boss, Kissing

8.5
26 Votes

Star Employee

Story by Sky Larkin

2 Mar 2023 3239 Readers comments 6 Min Read

(SHORT STORY) Wilson is a bad employee, livestreams erotic videos of himself in the bathroom on company time and gets caught doing so by his cranky boss. Fortunately, Wilson has the chance to turn things around, but he has to submit and give up his phat bubble butt to do so.

Topics: Muscle, Straight Men, Slut, Interracial, Infidelity, Bubble Butt, Domination, Submission, Boss, Straight to Gay, Fucking

9.3
29 Votes

The Office Slut (ch. 4)

Story by Baltcumcump

26 Feb 2023 3140 Readers comments 6 Min Read

Devin, the OnlyFans porn star tries to leave that life behind while working for a new firm. The only problem is he had too many fans that are willing to keep his secret, but only if he cooperates.

Topics: Anal Sex, Interracial, Breeding, Co-worker, Oral & Blowjobs, Boss, Office Sex

9.2
23 Votes

Gypsy Passion (ch. 2)

Story by Stipa

20 Feb 2023 821 Readers comments 13 Min Read

(This is Luka and Finn story. You can meet Luka i Gypsy Passion for a brief moment.) Finn just found out his boyfriend is cheating on him, and that their relationship was a lie. He turns to his Bodyguard Luka for some comfort.

Topics: Romance, Sex, Age Difference, Boss, Love

9.3
67 Votes

I Fell For The Director

Story by GG

18 Feb 2023 3234 Readers comments 22 Min Read

A cute new employee catches the eye of the black director at work - but there are limits to how far they can go.

Topics: Interracial, Co-worker, Twink, Age Difference, BBC, Boss, Office Sex

9.6
89 Votes

Yes Sir (ch. 4)

Story by LittleBuddy

5 Feb 2023 6576 Readers comments 22 Min Read

The door opened slowly, revealing the insides of the familiar house, the foyer beyond fairly dark. As the door opened further, he came into view, Mr. Gibson, Dennis, my boss, standing in a pair of big black boots, his thick muscled legs looking downright amazing as my eyes trailed up the bare flesh to a black leather jock housing the big package I was coming to sample.

Topics: Anal Sex, Muscle, Daddy, BDSM, Boss

8.6
20 Votes

Foreman

Story by Phaggotry

1 Feb 2023 1849 Readers comments 8 Min Read

Jimmie Wright is up for the job of foreman on the loading docks. The thing that stands between him and his promotion is this whiny preppy mulatto named Gorham. Jimmie has a plan to get Gorham right in the head by making him his bitch, forcing him to use his tongue to suck his dick and to lick his boots clean.

Topics: Black Men, Feet, Verbal, Oral & Blowjobs, Boss, Blue Collar, Boots

9.6
49 Votes

Donkey Cakes (ch. 2)

Story by Charlie Walker

22 Jan 2023 6179 Readers comments 25 Min Read

Latino jock keeps messing up at work - and to make up for it he's going to have to offer his big himbo bubble to get eaten by his pervy boss.

Topics: Rimming, Daddy, Jock, Coercion, Sportsmen, Bubble Butt, Age Difference, Boss

9.8
44 Votes

My New Personal Assistant (ch. 9)

Story by I. Dusk

18 Jan 2023 3604 Readers comments 17 Min Read

I was sensitive, and my whole body was aching. The ropes were cutting my wrists, my legs were shaking from being high in one position, and my hole felt like it’d been ripped apart. Yet, the weirdest thing was that I liked it. How much I've missed this feeling. I buried this longing for thrill and pain deep, and now it surfaced more intensely than ever in my life! He leaned over me and kissed ...

Topics: Anal Sex, Rough Sex, Straight Men, Bondage, Rimming, Oral & Blowjobs, Domination, Married, Boss

9.8
54 Votes

My New Personal Assistant (ch. 8)

Story by I. Dusk

4 Jan 2023 4740 Readers comments 18 Min Read

I went to him and kissed him, trying to force him into the door frame when he yanked my hair down, and I, with a scream, knelt before him. "What the fuck?!" "Manners, baby." "You love it when I fight you." "Yes, I do. Still, I have different plans now, so turn off that hunter's attitude. You are now the prey. The sooner you accept it, the less it will hurt." "Maybe I like it to hurt."

Topics: Anal Sex, Rough Sex, Straight Men, Bondage, Verbal, Oral & Blowjobs, BDSM, Deep Throat, Boss

9.6
56 Votes

My New Personal Assistant (ch. 7)

Story by I. Dusk

26 Dec 2022 4123 Readers comments 15 Min Read

His eyes were like those of a lion's. Hunter, calm and relaxed, observing and stalking me as its prey. Now I knew. "Matt. I would destroy you. I told you I am not a gentle lover. I fuck. I fuck hard and ruthlessly. I let guys stronger than you are, leave in tears, and I don't think our professional relationship could withstand that." "What if exactly that is what I want?"

Topics: Rough Sex, Verbal, BDSM, Boss

9.4
87 Votes

Fiance of my Ex-Boss (ch. 2)

Story by I. Dusk

23 Dec 2022 6462 Readers comments 8 Min Read

The horny suit-bitch was Karl's fiance. This was just the best revenge I could think of. And no one can sue me for it! I looked at him the way I stare at my prey. His need to look at me was now stronger than his will. Check.

Topics: Muscle, Alpha Male, Armpits, Revenge, Car, Oral & Blowjobs, Boss, Blue Collar

9.1
28 Votes

First lick (ch. 4)

Story by lickme

21 Dec 2022 2627 Readers comments 2 Min Read

I was becoming his sex toy and I couldn't say no!

Topics: Big Dick, Submission, Boss

9.1
65 Votes

Fucking With My Boss

Story by Prikz

17 Dec 2022 6216 Readers comments 11 Min Read

Working late in the office with my boss turned out to be pretty exciting

Topics: Anal Sex, Rimming, Daddy, Oral & Blowjobs, Boss, Fucking

8.8
10 Votes

You're Kind of a Shitty Person (ch. 3)

Story by James

15 Dec 2022 3131 Readers comments 6 Min Read

Five minutes into his new job and Daniel already has an attitude. Ralph warns him against being disobedient during his job orientation, but perhaps his warning was too harsh. He didn't mean to upset his new employee, but he did find Daniel's crying face kinda cute.

Topics: Muscle, Crossdressing, Straight Men, Humiliation, Jock, Co-worker, Big Ass, Size Difference, Degradation, Boss, Illustrated

9.7
66 Votes

My New Personal Assistant (ch. 5)

Story by I. Dusk

15 Dec 2022 5361 Readers comments 15 Min Read

"I think you know what I am trying to do, Thomas." He reached and touched the side of my neck. "Are you sure, Matt? I am not usually a gentle lover." He squeezed harder as if to give me a taste of what I was getting myself into. Fuck, my cock just leaked the first blob of precum into my briefs, and I was never more aware of it than I was just now!

Topics: Straight Men, Rimming, Romance, Oral & Blowjobs, BDSM, Boss

9.1
66 Votes

The Manager

Story by Shadow123

8 Dec 2022 4932 Readers comments 6 Min Read

The manager and I were the only ones left late at night in the office. I was shocked by what happened next.

Topics: Hairy men, First Time, Daddy, Age Difference, Boss, Mature Men

9.0
56 Votes

First lick (ch. 2)

Story by lickme

6 Dec 2022 4222 Readers comments 3 Min Read

Encountering an enormous cock for the first time has me mesmerized and opens up a whole new world of sexually fulfillment

Topics: Big Dick, Boss, Fucking

9.4
60 Votes

My New Personal Assistant (ch. 4)

Story by I. Dusk

6 Dec 2022 5540 Readers comments 11 Min Read

"Don't play with me, Thomas." I was getting tenser under his gaze. He had this soft smirk and stoic gaze that felt like it was ripping through my soul. "Am I playing with you?" "I think you may." I tried to get him to stop without explicitly telling him that the way he was staring at me was making me hard, and that made me uncomfortable. "Would you like that?" Would I? Fuck. Stop getting ...

Topics: Muscle, Straight Men, Domination, Boss

8.6
88 Votes

First lick

Story by lickme

5 Dec 2022 7187 Readers comments 2 Min Read

A young naive guy being led towards a whole new appreciation for cock

Topics: Big Dick, First Time, Boss, Fucking