Page 2, Stories by Prettyboy

Fucked in my new knee high laced boots

1 Dec 2024 comments

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.

8.0 (9) 317 Reads 4 Min

I am a Hot Bitch

11 Nov 2024 comments

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

6.7 (16) 921 Reads 4 Min

Building My Own Porn Site

12 Oct 2024 comments

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.

6.7 (13) 1170 Reads 3 Min

Keds Club (ch. 2)

10 Oct 2024 comments

Jimmy has bought a new pair of pink Keds and is excited to show them off to the club. The pretty new sneaks are a real turn for the members the club as Tom fucks Jimmy in his pretty new sneaks

8.1 (4) 227 Reads 3 Min

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

9.3 (2) 404 Reads 5 Min

My Life as a Pretty Bitch (ch. 2)

24 Sep 2024 comments

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

8.8 (6) 896 Reads 3 Min

My Life as a Pretty Bitch

23 Sep 2024 comments

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

9.1 (12) 1486 Reads 5 Min

Chuck Buddies (ch. 6)

17 Sep 2024 comments

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.

9.7 (4) 273 Reads 3 Min

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) 311 Reads 4 Min

Chuck Buddies (ch. 4)

23 Aug 2024 comments

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) 321 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) 542 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) 732 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.

8.1 (11) 1182 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) 4131 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 (29) 1342 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) 714 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) 893 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) 883 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) 491 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) 558 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) 922 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) 592 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) 649 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) 1062 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) 697 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) 535 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) 1752 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) 4514 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) 583 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) 2164 Reads 6 Min