Page 3, Stories by Prettyboy

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) 950 Reads 4 Min

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 (7) 561 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) 581 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.

8.3 (15) 1088 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) 607 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.

9.5 (11) 673 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) 1100 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) 727 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) 551 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) 1798 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) 4734 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.

8.2 (10) 609 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) 2298 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) 625 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) 923 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) 1036 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) 1630 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) 1760 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

7.8 (19) 1501 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) 1716 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) 906 Reads 5 Min

Daddy and his Ballet Boy (ch. 2)

23 Feb 2024 comments

Ricky hooks up with another ballet boy who is Black, Sam. These beautiful ballet boys enjoy a great fuck

9.7 (12) 2136 Reads 4 Min

Chuck Buddies (ch. 3)

15 Feb 2024 comments

Paul has finally left his wife so he can be with Jack. Paul knew he had to leave when he was thinking of Jack's ass when he was having sex with his wife. Paul and Jack have wonderful fuck together.

8.2 (20) 1322 Reads 3 Min

Chuck Buddies (ch. 2)

13 Feb 2024 comments

Jack has come out and is meeting up with guys online. His friend from high school, Paul contacts Jack and wants to explore gay sex while still living with his girl friend

8.5 (31) 1838 Reads 3 Min

Chuck Buddies

12 Feb 2024 comments

Paul and Jack are good friends in high school. They both love wearing high top Converse sneaks. They start to experiment with sex and Paul fucks Jack for the first time.

8.2 (50) 4334 Reads 3 Min

Pretty in Pink (ch. 2)

9 Feb 2024 comments

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

9.1 (9) 703 Reads 5 Min

Boys in Boots

5 Feb 2024 comments

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.

8.8 (23) 1598 Reads 5 Min

I Love Ass (ch. 2)

3 Feb 2024 comments

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

8.3 (6) 635 Reads 3 Min

Loving my high heels (ch. 2)

25 Jan 2024 comments

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.

9.0 (12) 443 Reads 4 Min

Keds Bitch

15 Jan 2024 comments

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.

8.4 (20) 2258 Reads 4 Min