Stories by Prettyboy

Pretty in Pink (ch. 5)

7 Jun 2025 comments

Jackie loves her Keds and hi top pink Chucks. She lives with Jim and wears pink leather shorts that are a turn on for Jim. They enjoy some hot sex together enjoying the pink shorts and boots

8.9 (3) 126 Reads 4 Min

First Time

31 May 2025 comments

Jack has always been turned on my boots and leather and is attracted to men wearing them. He goes. to leather bar where he meets Jim who initiates Jack into gay sex.

7.9 (12) 937 Reads 4 Min

Jimmy begins each day using his pretty boots to get off by sucking them and fucking himself with his boot. John loves to watch Jimmy having fun and get hard watching him so he needs fuck Jimmy in his pretty boots.

9.6 (3) 108 Reads 4 Min

Loving my high heels (ch. 5)

25 May 2025 comments

Jack likes to top and bottom. Today he looks to bottom in his Alexsandro Vasini red boots with 60mm heels. He meets leather man, Joe who tops Jack in his motorcycle boots

8.2 (4) 138 Reads 3 Min

My high Black Leather Docs

21 May 2025 comments

Jack likes to top and bottom. When he tops he wears his high black laced Docs. Jimmy is a submissive twink that likes being fucked by a man in high black boots.

8.6 (4) 228 Reads 4 Min

White Leather Bitch

18 May 2025 comments

Jimmy is turned on by white leather. He loves wearing white leather jeans and boots. His partner John loves fucking Jimmy who is wearing white leather shorts with zippered ass.

8.7 (7) 305 Reads 4 Min

Pretty Boots (ch. 2)

16 May 2025 comments

After a hot fuck in his pretty white Nike boots with pink swoosh, Jimmy hooks up with John wearing his gorgeous brown cowboy boots for some more fucking.

8.5 (5) 153 Reads 3 Min

Pretty Boots

14 May 2025 comments

Jimmy loves his pair of hi top white Nikes with the pink swoosh. They are perfect for a bottom bitch. John like fucking a femboys and is turned on by Jimmy in his pretty boots.

8.1 (9) 444 Reads 4 Min

Loving my high heels (ch. 4)

28 Apr 2025 comments

Jackie loves wearing boots with high heels. He meets Jeff who is looking to fuck a femboy and and gets hard seeing Jackie in his knee high white patent leather boots with 3" heels. They have some hot booted sex.

9.3 (2) 266 Reads 4 Min

I'm a boot licking bitch

17 Apr 2025 comments

Jackie gets off licking a leather boot before his top fucks him. He meets Jess who is wearing gorgeous black boots and is turned on by Jackie's shiny pink cowboy boots. They have hot sex in their boots.

8.9 (3) 315 Reads 4 Min

Pretty in Pink (ch. 4)

4 Apr 2025 comments

Jackie is a cute twink who loves wearing pink. He is wearing new pair of pink leather Nike hi tops with white laces, girly white socks and silver anklets. He goes on line to find a top who will enjoy fucking a bitch wearing pink leather boots

8.3 (8) 710 Reads 5 Min

Daddy and his blond boy

23 Mar 2025 comments

Justin a mature man lives with a pretty blond. boy Jason. The story describe how they spend their day and their hot sex life.

7.7 (13) 2733 Reads 7 Min

Keds Bitch (ch. 16)

20 Mar 2025 comments

Jackie is wearing her pink Keds is looking for an older man to fuck him. He meets Justin, a gorgeous man in his late 30's wearing white leather jeans and hi top AF!s

9.6 (5) 407 Reads 5 Min

Pretty in Pink (ch. 3)

13 Mar 2025 comments

Pink has just bought a pair of pink leather hi top Nikes and feels so hot on them. She can't wait for Rick to get home so he can fuck his femboy in her pretty pink boots

8.9 (5) 501 Reads 4 Min

Keds Bitch (ch. 15)

10 Mar 2025 comments

After having hot sex, Tom and Jackie spend weekends together. In the morning they start with Tom licking the soles of Jackie Keds while Jackie blows him. Later in shower Tom pees on Jackie's pretty ass who loves the taste of Tom's urine when she sucks his dick

9.3 (2) 400 Reads 3 Min

Keds Bitch (ch. 14)

8 Mar 2025 comments

A few months ago Tom saw a pretty boy wearing white Keds. Ever since he dreams of fucking a femboy wearing Keds. He meets Jackie wearing her Keds and he realizes his dream.

9.7 (5) 245 Reads 5 Min

Fuck me in my Mary Janes

1 Mar 2025 comments

Jackie, a crossdressing bitch, has a new pair of Mary Janes and is looking for a guy wearing high black boots to fuck her. Jeff is turned on my Jackie wearing Mary Janes so they hook up for a hot fuck.

8.8 (8) 622 Reads 4 Min

Leather Boys Club

16 Feb 2025 comments

Jake and Jim love wearing tight leather jeans. The feel of tight leather around their crotch and ass makes them hard as well as looking a boy's ass wrapped in tight black leather. The leather stimulates some hot sex for these twinks

7.3 (11) 724 Reads 4 Min

I love pretty boys in white boots

14 Feb 2025 comments

Jeff has a fetish for boots, particularly white boots on femboys. Jackie is turned on by Jeff and his denim cowboy boots so they satisfy the their fetish with some booted fucking.

9.1 (10) 495 Reads 4 Min

Crossdressing Boot Bitch (ch. 2)

4 Feb 2025 comments

Jackie likes Only Maker website which features guys in women's boots with high heels. He is wearing a pair of knee high white patent leather laced boots which attracts Jim. Jim enjoys fucking Jackie in his knee high black Docs

9.8 (6) 306 Reads 4 Min

Fuck me in my high red boots

28 Jan 2025 comments

Jackie, wearing new knee high red platform boots with 5" heels, is looking for a top. He meets Jimmy wearing knee black Docs who is turned on my Jackie's gorgeous red boots. They have great fuck in their wearing their boots

8.9 (5) 503 Reads 3 Min

Keds Bitch (ch. 13)

20 Jan 2025 comments

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.

9.5 (3) 204 Reads 3 Min

Keds Bitch (ch. 12)

12 Jan 2025 comments

Jackie and Tommy are Keds bitches and are living together. They just got a pair of Keds with silver glitter for Jackie to wear so Tommy can fuck her in these gorgeous new sneaks

9.5 (3) 194 Reads 3 Min

Keds Bitch (ch. 11)

4 Jan 2025 comments

Jackie is a Keds bitch who usually bottoms for a guy wearing leather and high boots. He want to hook up with another Keds bitch so he can really enjoy his fetish.

9.2 (3) 327 Reads 3 Min

My Boot Shop

28 Dec 2024 comments

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.

7.5 (21) 1178 Reads 4 Min

Keds Bitch (ch. 10)

21 Dec 2024 comments

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.

8.9 (3) 361 Reads 4 Min

Keds Bitch (ch. 9)

19 Dec 2024 comments

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.

9.5 (3) 238 Reads 3 Min

My Boot is like a Cunt

17 Dec 2024 comments

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

9.5 (7) 435 Reads 3 Min

Being a Boot Bitch

10 Dec 2024 comments

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

8.8 (11) 650 Reads 3 Min

Two Bitches and Their Boss

2 Dec 2024 comments

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

9.0 (9) 1866 Reads 5 Min