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.

Two Bitches and Their Boss

By Prettyboy 2 Dec 2024

Jackie is living with Jess now. Jackie has a femboy friend, Jimmy, and invites him over so he can enjoy Jess's 7". Jimmy is spit roasted as he sucks Jackie's cock while being fucked

8.3 (10) 2233 5 Min Comments

A sock-sub's journey to slavery

By Lowlifesocksub 28 Nov 2024

A sock-kink crush unexpectedly resurfaces after years, taking Tom on a journey from sub to fag to sissy slave, proving that a true sock-kink will do anything to get his hit, and that fantasy and reality don’t always match up.

9.6 (26) 6927 29 Min Comments

Laid By the Boss (ch. 3)

By Jackov Hardwick 2 Nov 2024

In the final chapter, Ethan loses his anal cherry to his boss, Jason. It is a ride he thoroughly ends up enjoying.

9.6 (78) 5464 9 Min Comments

Laid By the Boss (ch. 2)

By Jackov Hardwick 31 Oct 2024

Ethan continues down his path of man to man sex with Jason, his gay boss. Ethan sucks his first cock and Jason rewards him handsomely.

9.4 (60) 4268 7 Min Comments

Laid By the Boss

By Jackov Hardwick 29 Oct 2024

Ethan finds himself newly divorced and experiences his first man to man sex with Jason, his gay boss.

9.1 (121) 7475 5 Min Comments

The Job Interview: A Jake's Story (ch. 5)

By 138b 27 Sep 2024

Jake's stay in the Big City has gone from bad to worse.

8.5 (32) 2543 22 Min Comments

The Job Interview: A Jake's Story (ch. 4)

By 138b 22 Sep 2024

Jake's job interview in the "Big City has become a bit more complicated.

9.3 (32) 2335 16 Min Comments

The Big Boss Man

By Bigmac 10 Sep 2024

After moving away from home to start my freshman year of college, I take a job working at a restaurant and find myself taking on some overtime with my new manager.

8.9 (101) 7449 8 Min Comments

The Job Interview: A Jake's Story (ch. 3)

By 138b 31 Aug 2024

A job interview to a major "Big City" that has gone very wrong.

9.5 (38) 2825 18 Min Comments

One the Job

By voidcollection 8 Jul 2024

Elliot's new job has been boring and tedious, but today things take a turn for the interesting when he finally meets the boss

8.7 (25) 2632 15 Min Comments

The Byte (ch. 4)

By Swallow Your Lightsaber 13 Jun 2024

Dr. Michael Fischer gets Billy Webb to admit himself to the Carl Bell Psychiatric Center. They try desperately to keep him from slipping further away. Horace Taylor continues to collect, adding a student who had a crush on him. He believes himself to be a God. Who is to stop him?

8.4 (2) 535 17 Min Comments

The Byte (ch. 3)

By Swallow Your Lightsaber 11 Jun 2024

Horace finally lets Billy Webb out so he can return to the lab. He is going to a conference in another part of town. The psychiatrist, Michael Fischer, visits him. He can see the young man is upset, so they talk. IT security engineer gets involved and becomes Horace's second victim.

9.4 (2) 503 18 Min Comments

Nineteenth Hole

By Hangry Holz 10 Jun 2024

After taking care of his husband for months, Eric takes a job at a golf course in a retirement community. The job quickly becomes more fulfilling than any work he’s done before.

9.2 (78) 8710 19 Min Comments

The Byte (ch. 2)

By Swallow Your Lightsaber 10 Jun 2024

A week has passed, so Horace has let Billy return to the lab. Horace is in a different part of the city at a conference. The psychiatrist stops to visit Billy, who is very disturbed over something. Fischer offers free sessions, and Billy has a breakdown. There is no escape.

9.6 (3) 760 18 Min Comments

The Byte

By Swallow Your Lightsaber 7 Jun 2024

Some believe the entirety of our world is a simulation. What if everyone you knew and loved was but an AI construct? One man has figured out how to hack the source code. What if this man has issues and is bent on domination and control of others? Would you want to be the object of that person's attention?

8.8 (4) 1835 18 Min Comments

The Boss and His Assistant

By mecookie123 27 Apr 2024

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?

7.9 (11) 2854 10 Min Comments

The Agreement

By Dingo Pup 25 Mar 2024

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

9.3 (57) 6148 22 Min Comments

The Boardroom (ch. 4)

By Bill Drake 4 Mar 2024

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

9.9 (30) 3774 28 Min Comments

A Long Ride Home (ch. 2)

By Hangry Holz 26 Feb 2024

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.

9.4 (107) 9242 21 Min Comments

The Day I Met Boss

By Dingo Pup 25 Feb 2024

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

9.3 (104) 7102 20 Min Comments

The Copy Machine Incident

By Bear Stories 8 Feb 2024

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.

9.3 (66) 6241 16 Min Comments

New bull (ch. 2)

By Staffido 7 Feb 2024

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

9.4 (97) 13628 8 Min Comments

Why Him, of All People (ch. 4)

By I. Dusk 27 Nov 2023

“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.

9.5 (11) 2028 13 Min Comments

My New Personal Assistant (ch. 29)

By I. Dusk 20 Nov 2023

“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 already know well enough that it makes me even more ...

9.6 (17) 1925 21 Min Comments

Tug of Whore

By Hangry Holz 17 Nov 2023

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

9.1 (33) 6148 14 Min Comments

The Whores in the Band

By Holden 19 Oct 2023

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.

8.7 (45) 5040 23 Min Comments

First lick (ch. 6)

By lickme 14 Oct 2023

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

9.1 (26) 3419 6 Min Comments

Fiance of my Ex-Boss (ch. 20)

By I. Dusk 14 Sep 2023

"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."

8.9 (12) 1972 13 Min Comments

First lick (ch. 5)

By lickme 11 Sep 2023

my boss and I have more sexual encounters

9.2 (26) 1835 3 Min Comments

The Gardener (ch. 4)

By just imagine 9 Sep 2023

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

8.9 (29) 2542 5 Min Comments

Why Him, of All People (ch. 3)

By I. Dusk 26 Aug 2023

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.

9.4 (19) 1692 15 Min Comments

My New Personal Assistant (ch. 27)

By I. Dusk 15 Aug 2023

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 there in gym clothes, and he was sweating.

9.5 (22) 1853 12 Min Comments

Why Him, of All People (ch. 2)

By I. Dusk 9 Aug 2023

“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?

9.4 (34) 2129 12 Min Comments

My New Personal Assistant (ch. 26)

By I. Dusk 4 Aug 2023

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.

9.7 (22) 1664 18 Min Comments

Training at the Skyland Club

By Habu 1 Aug 2023

Sex training to meet the boss’s need.

9.3 (32) 3392 24 Min Comments