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.

7.7
New

The Boss and His Assistant

Story by mecookie123

27 Apr 2024 307 Readers comments 10 Min Read

Johnny's life has been turned upside down. He now has a lot of free time, is working as a personal assistant the best choice? Especially when it if for a sexy millionaire?

Topics: Masturbation, Boss

9.0
New

Employee of the month

Story by Shadow123

15 Apr 2024 2438 Readers comments 9 Min Read

Jerry is caught for a fireable offense in the office. But as the new hot young guy in the office, his boss gives him one last chance to keep his job. How far will he go to avoid being fired.

Topics: First Time, Domination, Boss, Office Sex

9.8
40 Votes

The Agreement

Story by Dingo Pup

25 Mar 2024 2909 Readers comments 21 Min Read

Boss’s Boy wakes up in a cage and immediately begins to panic. His journey under his new Master is just beginning.

Topics: Piss, Humiliation, Degradation, Domination, Submission, BDSM, Boss

9.8
24 Votes

The Boardroom (ch. 4)

Story by Bill Drake

4 Mar 2024 1618 Readers comments 26 Min Read

Bill takes a little me time and adjusts to single life before getting back into the suitsex parties.

Topics: Oral & Blowjobs, Boss, Suits, Orgy, Fucking

9.6
74 Votes

A Long Ride Home (ch. 2)

Story by Hangry Holz

26 Feb 2024 5197 Readers comments 20 Min Read

In the middle of the night at a truck stop, Dennis sends 18-year-old Johnny around to five trucks to earn enough money to pay back the gambling debt racked up by Johnny's boss.

Topics: DP, Brothers, Threesome, Abduction, Creampie, Interracial, Alpha Male, Breeding, Bareback, Boypussy, Age Difference, BBC, Anonymous, Boss, Blue Collar

9.3
93 Votes

The Day I Met Boss

Story by Dingo Pup

25 Feb 2024 4368 Readers comments 19 Min Read

A cocky and mouthy little slut chose the wrong day to upset a Master. A Boss and His Boy Story.

Topics: Piss, Anal Sex, Fisting, Group Sex, Humiliation, Degradation, Domination, Submission, BDSM, Boss, Tag Team

9.4
47 Votes

The Copy Machine Incident

Story by Bear Stories

8 Feb 2024 3626 Readers comments 16 Min Read

When the boss everyone hates gets his tie stuck in the copying machine, the office workers don't seem to care, not about getting him unstuck at least.

Topics: Anal Sex, Bear, Oral & Blowjobs, Gangbang, Boss, Office Sex

9.2
62 Votes

New bull (ch. 2)

Story by Staffido

7 Feb 2024 6262 Readers comments 7 Min Read

The boss took one of his cum-producing bodybuilders as the main course. His body was no longer his.

Topics: Muscle, Bondage, Forced, Milking, Sci-Fi, Master & Slave, Rape, Boss, Bodybuilder

9.3
8 Votes

Why Him, of All People (ch. 4)

Story by I. Dusk

27 Nov 2023 1370 Readers comments 13 Min Read

“I hope you like red stockings. I’ve been hard the whole night because I wore them under the pants.” I turned to him and watched him with hunger. I took a step toward him. “A-a-a, big guy! Not here! We are still not finished.” He grinned at me flirtatiously. I growled and turned back to wipe the glasses.

Topics: Romance, Seduction, Twink, Oral & Blowjobs, Lingerie, Boss, Bartender

9.7
15 Votes

My New Personal Assistant (ch. 29)

Story by I. Dusk

20 Nov 2023 1484 Readers comments 20 Min Read

“You should go now, Matt,” Tomas’s voice was rough, nearly ominous. “Why?” like a person possessed, I stepped toward him. "I’ve been holding back for too long now. It’s getting dangerous.” I knew perfectly well he was losing control now. I saw him in his calm and stoic, and I saw him in rage when he became a beast not holding any bars! His eyes tried to warn me. Doesn’t he ...

Topics: Relationship, Seduction, Domination, BDSM, Boss

8.9
26 Votes

Tug of Whore

Story by Hangry Holz

17 Nov 2023 4419 Readers comments 13 Min Read

Point of view story about finding out what happens in the boss's private room.

Topics: Black Men, DP, Bondage, Humiliation, Interracial, Alpha Male, Bear, Age Difference, Ass to Mouth, Ass Play, BDSM, Boss

8.8
39 Votes

The Whores in the Band

Story by Holden

19 Oct 2023 3477 Readers comments 22 Min Read

In 1982, horndog casting agent Don Castellano assists a music company executive in putting together a boy band by scouting out three perfect, gorgeous boys. Besides being talented singers and dancers, the boys must also be talented cocksuckers and enjoy getting fucked up the ass by Big Dick.

Topics: Big Dick, Drugs, Cruising, Historical, Blond, Deep Throat, Rentboy, Boss, Blue Collar, Coming of Age, Orgy

8.9
17 Votes

First lick (ch. 6)

Story by lickme

14 Oct 2023 2652 Readers comments 2 Min Read

A young man falls under the spell of his boss's huge cock.

Topics: Big Dick, Forced, Boss

8.6
10 Votes

Fiance of my Ex-Boss (ch. 20)

Story by I. Dusk

14 Sep 2023 1526 Readers comments 13 Min Read

"Dude! If you fucking me now, I am fucking you in the shower when guys go to work," Kyle hissed, turning his head sideways. "Really? I was going to take you to one nice restaurant and sit on your cock in the restroom," I growled into Kyle's ear while I licked my fingers and put them in his hole, hearing him hiss and moan. "Fuck, yeah."

Topics: Public Sex, Locker Room, Relationship, Bromance, Boss

8.9
29 Votes

The Gardener (ch. 4)

Story by just imagine

9 Sep 2023 1718 Readers comments 5 Min Read

the gardeners Turkish boss has talked to his brother and calls the gardener in to discuss what went on

Topics: Hairy men, Daddy, Interracial, Boss, Turkish, Gardener, Fucking

9.4
18 Votes

Why Him, of All People (ch. 3)

Story by I. Dusk

26 Aug 2023 1336 Readers comments 15 Min Read

I heard his chuckle and looked at him. "What's so funny?" "You are, Sam. I can't figure you out." "Trust me, me neither. I am one smart person, but for some reason, when you are near, I start babbling like a moron. Like now, for example. Damn it." He was grinning like a mischievous little brat. Great.

Topics: Romance, Co-worker, Lingerie, Boss, Bartender

9.6
20 Votes

My New Personal Assistant (ch. 27)

Story by I. Dusk

15 Aug 2023 1553 Readers comments 11 Min Read

Two o’clock. I opened the door, and Matt's car was nowhere close. I imagined all the things I would do to him if he were mine for being late. I closed the door and returned to my desk, only to stand back three minutes later. I cursed for myself and went there. He is my boss, not my sub! I kept repeating that to myself until I opened the door, and my mind got blank as a canvas. Matt stood ...

Topics: Romance, BDSM, Boss

9.4
33 Votes

Why Him, of All People (ch. 2)

Story by I. Dusk

9 Aug 2023 1753 Readers comments 11 Min Read

“Do you want me to quit?” “No. Do you want to quit?” “No.” “Good. I think you looked good behind that bar.” He smirked and raised his eyebrow. Idiot! “I mean, you were good at bartending.” I don’t know why this is happening?! I can usually form two basic sentences without rambling like a fool. So why do I suddenly get so nervous when he is near?

Topics: Rimming, Romance, Feet, Sex, Lingerie, Boss, Bartender

9.7
18 Votes

My New Personal Assistant (ch. 26)

Story by I. Dusk

4 Aug 2023 1336 Readers comments 17 Min Read

I did everything I could not to grab him and kiss him when he walked past me. Thomas stared at me, and I believe he saw that and fought the same urge… My resolve was shaking, but I wanted to keep my head clear. I won’t be able to stand another refusal from him… Not after I just got myself together to be able at least somehow function.

Topics: Wrestling, Romance, Co-worker, Seduction, Boss

9.2
50 Votes

Todd's Boss

Story by flyguy91

13 Jul 2023 3892 Readers comments 14 Min Read

Todd's boss gives him clues that he's looking for some extra needs to be met.

Topics: Daddy, Sex, Boss

9.5
16 Votes

My New Personal Assistant (ch. 24)

Story by I. Dusk

29 Jun 2023 1095 Readers comments 15 Min Read

Thomas, it’s my birthday, and I really want to spend it with you. Not because we had a deal but because, you know, we both want to. I will come at ten. Please open the door.  I have only one birthday wish. Please, give me one day without the world. You can break my heart tomorrow. Matt

Topics: Romance, Boss, No Sex, Kissing

9.3
17 Votes

William (ch. 7)

Story by jeff1

21 Jun 2023 1228 Readers comments 5 Min Read

I was wrong.  I wouldn’t have been surprised if I had gotten two new deals the next day.  Markus’ workload was almost as full as his cock and balls. But by the time I got home that night I already had a work message:  Markus wanted to meet for breakfast and introduce me to a new client.

Topics: Black Men, Big Dick, Interracial, Cum, Oral & Blowjobs, Domination, Boss, Cum Swallow

9.3
21 Votes

Black Cock Warning (ch. 16)

Story by Einreise

9 Jun 2023 4278 Readers comments 11 Min Read

As I approach the office door, I realize that I need to change my attitude and get into the role of black cock bitch or things will not go well for me. I reach the door and knock, even thought it is half open.

Topics: Black Men, Anal Sex, Interracial, Co-worker, BBC, Submission, Boss

8.7
17 Votes

The Cut: Halfway Humpin (ch. 5)

Story by Phaggotry

5 May 2023 1560 Readers comments 6 Min Read

After being turned out in prison, Jessup is sent to a halfway house to get a renewed footing back into society.

Topics: Black Men, Threesome, Prison, Daddy, Boss

8.9
24 Votes

My New Personal Assistant (ch. 18)

Story by I. Dusk

26 Apr 2023 1795 Readers comments 16 Min Read

I looked at Thomas. I was about to ask him if we could go somewhere private when someone shouted. “30 seconds!!!” I looked that way and back at Thomas. He had this slight smirk. That cold, waiting stare of the feline hunter, I knew it too well by now. He was waiting on my move, and I knew there was no way to get him away from here. Fuck! I told him I wouldn’t kiss him in front of his ...

Topics: Spanking, Romance, Friends, BDSM, Boss

9.6
30 Votes

My New Personal Assistant (ch. 17)

Story by I. Dusk

17 Apr 2023 1935 Readers comments 17 Min Read

“You are coming, bro? Ashley's famous midnight dinner.” Brandon asked me as he was holding the door. I shook my head. “You go ahead. I want to make a call.” Brandon grinned widely. “Right, say hi from me.” “Just go.” He patted me on the shoulder, and I sat on Nate's bed, dialing Thomas’s number. “Isn’t it too soon to wish me Happy New Year?”

Topics: Anal Sex, Public Sex, Romance, Friends, Oral & Blowjobs, BDSM, Boss, Blue Collar

8.1
9 Votes

Office Dom and the weakling (ch. 2)

Story by Master Primus

14 Apr 2023 2664 Readers comments 17 Min Read

"Strip bitch", I ordered him. I actually had made a schedule for him and some rules he must follow. He was not allowed to wear anything except for his panties that I bought for him.

Topics: Muscle, Romance, Interracial, Top to Bottom, Submission, Boss

9.6
9 Votes

Loads and Tow

Story by Phaggotry

12 Apr 2023 3081 Readers comments 95 Min Read

An ex-con turned repo man gets entangled with his older bosses and his housemates.

Topics: Black Men, Crossdressing, Straight Men, Brothers, Hairy men, First Time, Transgender, Daddy, Top to Bottom, Age Difference, Size Difference, Married, Boss, Blue Collar