Gay Boots Stories

GayDemon's Stories: On this page you can find erotic fiction where you can read about men wearing or worshiping men in leather boots listed by date.

8.9
New

Black Boots and White Boots

Story by Prettyboy

12 Apr 2024 416 Readers comments 5 Min Read

I am Terry. I like to top and bottom depending on how I feel. When I top I wear knee high black riding boots that shine and when I bottom I wear beautiful white cowboy boots.

Topics: Anal Sex, Oral & Blowjobs, Boots

8.9
New

Realizing I'm a Bottom Bitch

Story by Prettyboy

11 Apr 2024 1037 Readers comments 6 Min Read

It took several years before I knew I was gay and realized my true identity. Some guys know when they are a boy they are gay. Mine was journey from a fetish for boots till I wanted to have sex with boys. Now I can't get fucked enough as a bottom bitch

Topics: Anal Sex, Leather, Coming Out, Age Difference, Boots

8.8
New

Keds Bitch (ch. 3)

Story by Prettyboy

9 Apr 2024 301 Readers comments 4 Min Read

Jimmy is so excited. He just received a pair of pink Keds what he ordered. Dirk, his Daddy, can't wait to fuck Jimmy in his sneaks while he wears his calf high black harness boots.

Topics: Anal Sex, Age Difference, Boots, Sneakers

8.1
New

Boys in Boots (ch. 2)

Story by Prettyboy

7 Apr 2024 439 Readers comments 4 Min Read

Carl takes Jack shopping for a new pair of boots. A new pair of gorgeous cowboy boots leads to a hot fuck

Topics: Anal Sex, Leather, Age Difference, Boots

9.9
New

A carpenter's commission releases the bully & beta-pig (ch. 3)

Story by Humiliation junky

6 Apr 2024 1231 Readers comments 17 Min Read

Chapter 3 sets the scene to more extreme humiliation and degradation in Chapter 4. We learn how Jon lures Paul back for more. They learn a bit more about each other, and Paul learns how to properly clean a man's boots and what it means go be a dirty little piss-pig...

Topics: Piss, Humiliation, Small Cock, Smoking, Boots

9.5
New

A carpenter's commission releases the bully & beta-pig (ch. 2)

Story by Humiliation junky

5 Apr 2024 1856 Readers comments 13 Min Read

There will be nine chapters charting the journey of two men, alpha-male and beta-boi, as they discover how mean and dirty they really are. This story involves, humiliation, scat, piss, boot worship and pipe smoking. If these things are not for you please do move on. This is the first story that I have published. It covers my own personal interest in humiliation, submission and an obsession with ...

Topics: Piss, Humiliation, Scat, Farting, Submission, Smoking, Diapers, Boots, Fucking

9.3
New

A carpenter's commission releases the bully & beta-pig

Story by Humiliation junky

4 Apr 2024 2963 Readers comments 12 Min Read

There will be nine chapters charting the journey of two men, alpha-male and beta-boi, as they discover how mean and dirty they really are. This story involves, humiliation, scat, piss, boot worship and pipe smoking. If these things are not for you please do move on. This is the first story that I have published. It covers my own personal interest in humiliation, submission and an obsession ...

Topics: Piss, Humiliation, Scat, Farting, Submission, Smoking, Diapers, Boots, Fucking

8.4
New

My Hot Interracial Marriage (ch. 2)

Story by Prettyboy

31 Mar 2024 587 Readers comments 4 Min Read

Jack bought Bill a pair of high top platform black Chucks so Billy puts them for a hard fuck and to initiate them into their sex life

Topics: Anal Sex, Interracial, Oral & Blowjobs, Age Difference, Boots

9.0
10 Votes

My Hot Interracial Marriage

Story by Prettyboy

19 Mar 2024 1010 Readers comments 6 Min Read

I am Jack married to my husband, Billy who is black. I am also Billy's Daddy since there is almost a 20 year age difference. I like to top Billy in knee high black boots and be boss to my pretty bitch

Topics: Anal Sex, Interracial, Oral & Blowjobs, Age Difference, Married, Boots

9.2
21 Votes

Hot Ass

Story by Prettyboy

15 Mar 2024 1300 Readers comments 4 Min Read

Jackie is a 23 years old with a hot, hungry ass. He goes to a park at night for quick fuck but is not satisfied. He meets Jeff at gay bar who spends the night fucking Jackie.

Topics: Anal Sex, Leather, Boots

7.4
10 Votes

Pretty Boys in Jeans

Story by Prettyboy

9 Mar 2024 998 Readers comments 4 Min Read

Frank is turned on by seeing pretty boys in tight faded jeans or shorts. He is able to hook up with Eddy who serves as an eager bottom for Frank

Topics: Anal Sex, Oral & Blowjobs, Age Difference, Boots, Jeans

9.4
6 Votes

Becoming a Top (ch. 2)

Story by Prettyboy

2 Mar 2024 1177 Readers comments 4 Min Read

Ricky is Carl's bitch boy. Ricky is wearing a pink bra, skirt, and high top pink Chucks waiting for Carl to come home and fuck him. Carl enjoys topping Ricky wearing knee high black laced boots.

Topics: Crossdressing, Age Difference, Boots, Sneakers

8.9
9 Votes

Keds Bitch (ch. 2)

Story by Prettyboy

25 Feb 2024 485 Readers comments 4 Min Read

Jimmy is a Keds bitch and is now living with Dirk. Dirk and Jimmy have great sex which includes fucking Jimmy with one of his cute sneaks.

Topics: Anal Sex, Oral & Blowjobs, Boots, Sneakers

9.2
7 Votes

Pretty in Pink (ch. 2)

Story by Prettyboy

9 Feb 2024 416 Readers comments 5 Min Read

Pinky is now living with Rick and enjoys a morning fuck with him to start the day.

Topics: Anal Sex, Boots, Sneakers

8.9
15 Votes

Boys in Boots

Story by Prettyboy

5 Feb 2024 968 Readers comments 4 Min Read

Carl is turned on my boys wearing high boots tucked into tight jeans. He finds Jack at a leather bar wearing jeans tucked into beautiful cowboy boots. Carl tells Jack about his collection of boots so they head to his place for hot booted sex.

Topics: Anal Sex, Rimming, Age Difference, Boots

8.3
6 Votes

I Love Ass (ch. 2)

Story by Prettyboy

3 Feb 2024 497 Readers comments 3 Min Read

Jimmy has been Joel's bitch for several months now. Joel is wearing knee high black laced boots ready dominate Jimmy.

Topics: Anal Sex, Rimming, Boots

8.5
8 Votes

Loving my high heels (ch. 2)

Story by Prettyboy

25 Jan 2024 213 Readers comments 4 Min Read

Jackie has just gotten a new pair of boots with 3" heels. Wearing them he puts on leather jeans with zippered as and heads for a leather bar where he meets Jake. Their boots and leather stimulate some hot sex.

Topics: Anal Sex, Rimming, Boots

8.2
18 Votes

Keds Bitch

Story by Prettyboy

15 Jan 2024 764 Readers comments 4 Min Read

Jimmy feels so hot wearing his Keds with faded denim shorts. He works in a shoe store that caters to gay men and meets Dirk who buys a pair of high top pink Converse which leads to some fun sex.

Topics: Anal Sex, Rimming, Boots

9.6
5 Votes

Jacque Meets Booted Andre

Story by Rowan

10 Jan 2024 371 Readers comments 5 Min Read

Riding Boot fetishism when a young French stud meets a member of the garde republicane.

Topics: Boots, Uniforms

8.8
15 Votes

Becoming a boot bitch

Story by Prettyboy

8 Jan 2024 695 Readers comments 5 Min Read

Since Jack was boy he had a thing for boots. He first sex is with Mark in college who wear beautiful cowboy boots that leads to Jackie becoming a botton boot bitch.

Topics: Anal Sex, Oral & Blowjobs, Boots

8.7
22 Votes

Daddy and his Ballet Boy

Story by Prettyboy

5 Jan 2024 3211 Readers comments 5 Min Read

Joe is 40 years old and love fucking pretty boys. He is living with Ricky who goes to dancing school. They have sex three different times in one day.

Topics: Anal Sex, Daddy, Twink, Age Difference, Boots

8.0
15 Votes

I Love Ass

Story by Prettyboy

4 Jan 2024 1908 Readers comments 4 Min Read

I love ass, particularly the smooth ass of a Twink. I find a Twink with a beautiful ass that I enjoy with my mouth and cock

Topics: Anal Sex, Rimming, Twink, Boots

7.8
22 Votes

Bottom Boy Services Blond

Story by Prettyboy

30 Dec 2023 1230 Readers comments 4 Min Read

Kenny, a bottom femboy, seeking a leather man to top him connects with Jeff, a gorgeous blond guy.

Topics: Anal Sex, Rimming, Leather, Femboy, Boots

9.2
39 Votes

The Drunk Colonel (ch. 4)

Story by Marine Rope Stud

30 Dec 2023 2516 Readers comments 25 Min Read

In this chapter, Air Force Major Fielding is locked down and used as fuck meat. His trainning begins with a severe whipping on the Cross to remove his stubborn streak. Straight Corporal Sean O'Connor is kidnapped and we learn of his incestous relationship with his Dad a former Marine. The Lieutenant is learning what it's like to be a Marine slave and Corporal Ryan Dickinson is falling love with ...

Topics: Anal Sex, Straight Men, Bondage, Rimming, Abduction, Incest, Military, Dad & Son, Drunk, BDSM, Boots

7.3
19 Votes

Boots and Leather

Story by Prettyboy

26 Dec 2023 1205 Readers comments 6 Min Read

Since Ben was kid, he has been turned on by boots and leather. He finds a Jake, a leather man, who can top Ben and enjoy great sex with boots and leather.

Topics: Anal Sex, Rimming, Leather, Boots

8.1
49 Votes

Becoming a Top

Story by Prettyboy

24 Dec 2023 2990 Readers comments 5 Min Read

Carl is has turned 40 and knows that he is totally gay and wants to top. He meets Ricky, age 22, and they connect so Carl can top this beautiful bottom boy.

Topics: Anal Sex, Daddy, Age Difference, Boots, Sneakers

7.9
20 Votes

Femme Boy enjoys BBC

Story by Prettyboy

23 Dec 2023 2962 Readers comments 5 Min Read

Jimmy is a femme boy with a fetish for boots and sneaks. He meets a gorgeous black guy, Joel, and they hook up for some hot sex.

Topics: Big Dick, Leather, Interracial, BBC, Femboy, Boots, Fucking