Page 2, Stories by Prettyboy

Chuck Buddies (ch. 5)

27 Aug 2024 comments

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

9.6 (4) 305 Reads 4 Min

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

9.7 (4) 315 Reads 3 Min

Keds Bitch (ch. 7)

14 Aug 2024 comments

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.

9.5 (3) 534 Reads 3 Min

Leathered Ass

6 Aug 2024 comments

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) 725 Reads 4 Min

Call Me a Fuckin Fruit

28 Jul 2024 comments

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.

8.3 (10) 1153 Reads 5 Min

I Love Fucking Femboys

26 Jul 2024 comments

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.

7.7 (19) 3863 Reads 4 Min

Boys and their tall Riding Boots

21 Jul 2024 comments

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 (28) 1282 Reads 4 Min

Keds Bitch (ch. 6)

14 Jul 2024 comments

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.

9.8 (6) 701 Reads 3 Min

My High Top Pink Chucks

6 Jul 2024 comments

Jimmy is pretty bitch boy who loves wearing his high top pink Chucks with his white denim short shorts and pink tank top. Tom is attracted to Jimmy tops him wearing new Nike high top AF1s

9.5 (7) 883 Reads 4 Min

Loving my high heels (ch. 3)

27 Jun 2024 comments

Jackie loves wearing high heels. He just received a pair of high black Chucks with 3" white heels. He meets Tom who is turned on by these Chucks and tops Jackie.

9.6 (8) 833 Reads 4 Min

Keds Club

21 Jun 2024 comments

Keds Club is for guys with a fetish for Keds. It has four members. Tom who tops, two bottoms, Jimmy and Jackie, and Dirk who does both. Jackie starts the meeting by asking to have his hot ass rimmed and fucked. Later Derek fucks Jimmy with his gender neutral blush colored Keds

9.8 (6) 477 Reads 3 Min

Keds Bitch (ch. 5)

16 Jun 2024 comments

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

9.1 (6) 552 Reads 4 Min

Crossdressing Boot Bitch

13 Jun 2024 comments

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.

8.5 (13) 878 Reads 3 Min

Hot Ass (ch. 2)

3 Jun 2024 comments

Jackie is wearing his pink Keds and white leather shorts with a zippered ass looking for a top. He meets Bob wearing gorgeous patent leather cowboy boots who is turned on by Jackie's white leather ass which he rubs and slaps while he fucks Jackie.

8.7 (9) 589 Reads 4 Min

Boys in Boots (ch. 4)

26 May 2024 comments

Jack is Carl's bottom bitch. However, he meets a beautiful boy his age, Curt, and is so turned on that he has top Curt wearing his new denim cowboy boots.

9.4 (10) 638 Reads 5 Min

What Porn Scenes Turn Me ON

20 May 2024 comments

Jack describes scenes from porn that turn him on. They serve to inspire great sex with his pretty bitch boy who loves wearing his pretty new high white Chucks while being fucked.

9.4 (15) 1046 Reads 5 Min

Boys in Boots (ch. 3)

18 May 2024 comments

Carl has bought a pair of Docs, Jadon HI polished boots. He feels do dominant in these boots that has to fuck his pretty bitch boy, Jack, who is wearing black leather jeans tucked into white cowboy boots. His jeans have zippered ass that Carl enjoys slapping the black leather while he fucks Jack

8.8 (8) 685 Reads 4 Min

Keds Bitch (ch. 4)

6 May 2024 comments

Keds has just released "gender neutral" sneaks that is perfect for queers who love Keds. Jimmy gets a pair blush can't wait to show them to his partner Dirk can't wait to fuck Jimmy in this cute new sneaks.

9.7 (5) 525 Reads 3 Min

Loving Ass of Pretty Femme Boys

30 Apr 2024 comments

Bill writes and gives talks on love and relationship. As he signs his book he likes to hit on young pretty femme boys which often leads to a hot fuck. Jimmy is turned on by Bill and his gorgeous cowboy boots.

8.3 (14) 1734 Reads 3 Min

Breeding Pretty Boys

14 Apr 2024 comments

Jerry loves a virign and breeding pretty boys. He meets Justin and connects with him so eventually he initiates Justin into gay sex. Justin is bred and becomes a gorgeous bottom bitch that loves cock up his ass.

8.3 (60) 4419 Reads 4 Min

Black Boots and White Boots

12 Apr 2024 comments

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.

8.3 (9) 574 Reads 5 Min

Realizing I'm a Bottom Bitch

11 Apr 2024 comments

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

9.2 (7) 2096 Reads 6 Min

Keds Bitch (ch. 3)

9 Apr 2024 comments

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.

9.3 (5) 588 Reads 4 Min

Boys in Boots (ch. 2)

7 Apr 2024 comments

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

8.4 (10) 849 Reads 4 Min

My Hot Interracial Marriage (ch. 2)

31 Mar 2024 comments

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

8.6 (7) 983 Reads 4 Min

My Hot Interracial Marriage

19 Mar 2024 comments

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

8.5 (12) 1529 Reads 7 Min

Hot Ass

15 Mar 2024 comments

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.

9.0 (23) 1722 Reads 4 Min

Pretty Boys in Jeans

9 Mar 2024 comments

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

8.4 (16) 1363 Reads 4 Min

Becoming a Top (ch. 2)

2 Mar 2024 comments

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.

9.4 (6) 1631 Reads 4 Min

Keds Bitch (ch. 2)

25 Feb 2024 comments

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.

9.1 (11) 868 Reads 5 Min