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.

The Drunk Colonel (ch. 13)

By Marine Rope Stud 22 Jan 2025

Air Force Major Fielding and his big horse cock become the sole property of Sgt. Collins and begins his new life as Collins personal property. Sgt. Scott O'Connor is replaced as number one at the Dairy Farm and is danger of becoming just another a milk stud. Anything can happen now.

9.1 (19) 1561 11 Min Comments

Keds Bitch (ch. 13)

By Prettyboy 20 Jan 2025

Jackie and Tommy wearing their Keds meet Johnny who is turned on by these cute bitches and their Keds. They hook for some hot sex with their sneaks.

7.7 (4) 245 3 Min Comments

Risk and Restraint (ch. 3)

By Topofthehill 6 Jan 2025

Adam discovers intense pleasure in a dominant-submissive encounter with James, embracing a journey of raw passion and deep surrender, ultimately finding himself enthralled and transformed by the experience.

9.7 (85) 3903 23 Min Comments

My Boot Shop

By Prettyboy 28 Dec 2024

Jacques owns a boot shop that caters to gays. He blows a new customer, Freddy, in the change room and hooks up later to fuck this virgin twink.

7.3 (23) 1301 4 Min Comments

Keds Bitch (ch. 10)

By Prettyboy 21 Dec 2024

Frank is Tommy's Daddy. He was once bisexual but now turned on by pretty femboys, like Tommy. Tommy is a Keds bitch with several pairs in different colours that match his nails.

7.2 (4) 401 4 Min Comments

Keds Bitch (ch. 9)

By Prettyboy 19 Dec 2024

Tommy has become true Keds bitch with a closet full of Keds in different colours. He meets Frank who is turned on by seeing Tommy in his cute sneaks which leads to some hot sex.

7.7 (4) 283 3 Min Comments

My Boot is like a Cunt

By Prettyboy 17 Dec 2024

Jack has a pair of boots with soft tan leather interior. After wearing them his foot sweats and so the interior leather is warm and wet like a cunt. Smelling his boots he comes inside them. He gets his bitch boy, Jimmy to lick the cum inside of boots while Jack fucks Jimmy

8.6 (8) 584 3 Min Comments

Being a Boot Bitch

By Prettyboy 10 Dec 2024

Jimmy, a beautiful black femme boy, is Jack's bitch. Jack is wearing a pair of St. Laurent Jonny boots with red leather interior. Jack orders Jimmy to sniff and lick the red leather while he fucks Jimmy who is totally Jack's boot bitch

8.2 (12) 885 3 Min Comments

Dressing up to seduce him

By Paul François 8 Dec 2024

Two high school students will soon graduate. They are secretly attracted to each other, until one of them enters a horseback competition. From the stables to the picnic table, the tone is set for a hot encounter.

8.2 (45) 2868 5 Min Comments

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) 2165 5 Min Comments

Fucked in my new knee high laced boots

By Prettyboy 1 Dec 2024

Jackie has fetish for boots and leather. He just got a new pair of knee high black laced boots and can't wait to have sex with them. He meets Jess who obliges.

7.4 (10) 383 4 Min Comments

I am a Hot Bitch

By Prettyboy 11 Nov 2024

Jackie is beautiful 23 year old boy with a fetish for leather and high heeled boots. He meets Guy who enjoys fucking Jackie in his boots and leather

6.4 (17) 990 4 Min Comments

Building My Own Porn Site

By Prettyboy 12 Oct 2024

I have collected pics that turn me on. I describe these pics of beautiful boys, their cock and asses and how I would like to service them.

6.3 (14) 1255 3 Min Comments

Keds Bitch (ch. 8)

By Prettyboy 1 Oct 2024

I am Jackie. This is day a in my life as a Keds bitch. I work at the men's clothing store and meet Neil who buys a pair of Nike high top white mid Blazers with the black swoosh and that evening fucks me in them while I am wearing my Keds

6.9 (3) 438 5 Min Comments

The Drunk Colonel (ch. 12)

By Marine Rope Stud 27 Sep 2024

Sheriff Preacher Caulfield becomes Sergeants Collins slave. Corporal Sean O'Connor, is purchased by an Arab Prince and Sergeant O'Connor and Collins go on another shopping trip for Marines.

9.8 (28) 2925 16 Min Comments

My Life as a Pretty Bitch (ch. 2)

By Prettyboy 24 Sep 2024

Jess is thinking about the sex he had with Jimmy. He can't wait to fuck Jimmy again and asks him over. Jimmy arrives in his white leather shorts and pink Keds and they have great sex together

7.8 (7) 974 3 Min Comments

My Life as a Pretty Bitch

By Prettyboy 23 Sep 2024

Jimmy is a gorgeous bitch that loves to bottom wearing knee high boots with high heels. He hooks up with leather man, Jess for some hot sex

8.5 (13) 1595 5 Min Comments

The Drunk Colonel (ch. 11)

By Marine Rope Stud 22 Sep 2024

Sergeant Collins and Sergeant O'Connor go hunting for new Marine meat and capture two hot Marines. Sheriff Preacher Caulfield comes calling at the farm. Business is booming and an Arab Sheik makes inquires.

9.5 (22) 2449 19 Min Comments

The Drunk Colonel (ch. 10)

By Marine Rope Stud 18 Sep 2024

Sergeant Collins and Sergeant O'Connor take Corporal O'Connor prisoner and make him part of the cum herd. The two Sergeants travel to Camp Lejeune and capture two new Marines for the farm. Sperm samples go out to prospective customers and the farm is in full production mode.

9.4 (22) 2376 16 Min Comments

Chuck Buddies (ch. 6)

By Prettyboy 17 Sep 2024

Paul is turned by seeing a Twink wearing white Keds so he buys a pair for Jackie who loves them. This leads to some hot sucking and fucking in her new sneaks.

8.1 (5) 308 3 Min Comments

The Drunk Colonel (ch. 9)

By Marine Rope Stud 13 Sep 2024

All four military captives are transported to the Dairy Farm, and the milking process begins. Corporal O'Connor becomes a problem. Sergeant O'Connor is the favorite of Sergeant Collins and a romance begins.

9.3 (25) 2530 16 Min Comments

Rubber Pleasures on the Horizon

By Paul François 29 Aug 2024

Boots send a message about being more grounded, about taking steps to actualize your aspirations. Terrence discovers very soon the power and the fucking fun of rubber boots.

8.6 (11) 984 6 Min Comments

Chuck Buddies (ch. 5)

By Prettyboy 27 Aug 2024

Jack likes to be called Jackie now and has a new pair of hi top black Chucks with 3" white heels. Her Daddy got hard when he saw his gurl in high heels which led to some hot sex

8.1 (5) 347 4 Min Comments

The Drunk Colonel (ch. 7)

By Marine Rope Stud 27 Aug 2024

Former Marine Corps Sergeant O'Connor is now a slave to his son Sean and housed in the dungeon for the time being. Sergeant Collins starts to build his Marine sperm farm after purchasing a small defunt dairy farm in the Carolina mountains. He already has three or maybe four Marines to bring to the farm and is planning on adding to that number very soon.

9.4 (23) 2632 15 Min Comments

Chuck Buddies (ch. 4)

By Prettyboy 23 Aug 2024

Paul has come out and is living with Jack. They love having sex in their Chucks and decide to buy new white hit tops. Paul gets a pair of hi top white platform Chucks and Jack gets the regular white hit tops. They can't wait to get back to have some sex in their new white boots

8.1 (5) 363 3 Min Comments

The Drunk Colonel (ch. 6)

By Marine Rope Stud 22 Aug 2024

Former Marine Sgt. O'Connor is captured by Sgt. Collins and is given to his son Corporal Sean O'Connor as a present to be made into his slave. And back at the dungeon, the Air Force Major is locked in a jail cell with Air Force Colonel Conroy who is working over the Major's studly body, taking whatever he wants from his bound victim, as plans are being made to create a Marine sperm farm.

9.4 (39) 3239 14 Min Comments

Keds Bitch (ch. 7)

By Prettyboy 14 Aug 2024

Jerry loves topping pretty blond boys. He hooks up with Jimmy online who looks so cute in his Keds. Jimmy wears his Keds while Jerry tops him in his patent leather shorty cowboy boots.

7.6 (4) 577 3 Min Comments

The Drunk Colonel (ch. 5)

By Marine Rope Stud 10 Aug 2024

The Air Force Major is turned into a Daddy slave by the young Marine Corporal Sean O'Connor, and Sgt. Collins continues to collect military prey for his dungeon.

9.5 (38) 3864 9 Min Comments

Leathered Ass

By Prettyboy 6 Aug 2024

Jackie is turned on my wearing tight leather jeans and shorts. He meets Dave who is turned on seeing Jackie in his pink leather shorts. They hook up with Dave riding Jackie in his black patent leather cowboy boots.

8.1 (11) 961 4 Min Comments

Call Me a Fuckin Fruit

By Prettyboy 28 Jul 2024

Jackie is wearing a new pair of pink leather shorts with the hopes of attracting a horny top. Jim is a turned on by Jackie's shorts and enjoys her ass both in the gorgeous pink leather and also in the flesh.

8.1 (11) 1259 5 Min Comments

I Love Fucking Femboys

By Prettyboy 26 Jul 2024

Jerry is bisexual but in the end he prefers a femboy's pussy. He meets Tommy who looks so cute in his white leather shorts and Nike Cortez and they hook up for some hot sex.

7.6 (21) 5592 4 Min Comments

Boys and their tall Riding Boots

By Prettyboy 21 Jul 2024

Jack and Justin are part of riding club. They are turned on by seeing guys in their tight breeches tucked into knee high black riding boots. They hook up for some hot sex in their tall boots.

8.8 (36) 1767 4 Min Comments

Keds Bitch (ch. 6)

By Prettyboy 14 Jul 2024

Ben is a top who likes fucking twinks. He meets Ricky who is wearing white Keds that turn him on and leads to some fun sex together.

8.8 (8) 766 3 Min Comments

Keds Bitch (ch. 5)

By Prettyboy 16 Jun 2024

Tom likes to top pretty femboys. He meets Jackie who just bought a pair of red Keds. Tom goes to Jackie's shoe store and buys a new pair of purple cowboy boots. Tom wears his new boots as fucks Jackie in his red Keds

8.3 (8) 607 4 Min Comments

Crossdressing Boot Bitch

By Prettyboy 13 Jun 2024

Jackie is a crossdresser and has new pair of women's knee high white patent leather laced boots and is looking for a top. Jackie hooks up with a leather boy, Jeff.

7.9 (16) 1210 3 Min Comments