Chuck Buddies

by Prettyboy

12 Feb 2024 2338 readers Score 8.3 (43 votes) PDF Mobi ePub Txt


Jack and Paul are friends in high school.   The both like wearing converse sneaks.  Jack likes wearing high top white Chucks while Paul is partial to high black Chucks.  Jack is 5-9, weighs, 160, has curly brown hair and likes wearing rings and beaded bracelets.  Paul is six feet, weighs 180, has black hair.  They both are good looking dudes.  They hang out together and like some boys going through puberty they are exploring their bodies and sexuality.   Once when Jack was staying overnight at Paul’s home  sleeping together in a kIng-size bed, each started playing with his own dick which had gotten hard.  They ended up jacking off and laughing about it.  When they were together, they did this few more times.  They both were dating girls and having sex which has included the girls giving them blow jobs.

They are both 18 now and staying at Paul’s place while his parents are away.  They talking about their experience with their girls. 

Paul  said. “My date, Jennifer, sucked my cock but took her mouth away at the end before I climaxed which was a downer.”

“That’s bad news.  I have been watching some gay porn and seen some great videos of guys sucking cock.   They take all the cum in their mouth.”

“Do you think you are gay, Jack”

“I am not sure but I have to say I was turned on by some gay porn. I love looking at your hard cock.   Want me to try to blow you, Paul”.

Jack reaches over and takes Paul’s dick and starts to pull on it.  Pretty soon Paul has a huger 6’ boner. 

“OK, Jack, I want you to suck me now.”

Jack immediately takes Paul’s cock in his mouth and starts to suck. 

“Oh fuck that feels good, Jack

It is not long before Paul comes in Jack’s mouth who swallows the cum.

“That was hot, Jack, Much better than how my girl did it”

“I loved sucking your dick, Paul.  Would love to do it again.  I know I can do it better next time”

They start watching some gay porn.  In some of the scenes, guys are wearing sneaks when they have sex.

“I love your high black Chucks, Paul.  I want to see you with just you Chucks on”

Paul puts on his sneaks and stands there naked.  Jack takes a photo of Paul.

“Oh fuck you look so hot.   I want to kiss your Chucks.”

Jack goes down on Paul’s black boots.  Paul gets hard seeing Jack lick his Chucks. 

“I want you to blow me again, Jack”

Jack sucks Paul’s cock while he rubs Paul’s boots. 

Paul explodes again in Jack’s mouth.  OHHHHHHHHH!

“Next time we are together, I want to try and fuck you, Jack and see how it feels.”

“I’d love that, Paul. Let’s do it with our Chucks on.  That would be so hot.  I will wear my high red ones.”

 It is several weeks before Paul’s parents are away.  Jack comes over wearing white denim shorts, a pink tank top and his high top red Chucks.   Paul is wearing a white tee and his faded jeans and his black Chucks.    They are start to kiss and rub each other’s crotches.   Jack unzips Paul’s jeans and takes out Paul’s cock, kisses it and licks it.

“Suck it, Jack and then I am going to fuck you.”

“OK, let’s take our clothes off but keep our boots on.”

Paul gets some lube to put on his dick and Jack’s hole. 

Jack is on his back with his legs and boots in the air.

Paul slowly enters Jack’s hole. 

“How does it feel, Jack?”

“It hurts a little but keep going, Paul.”

Paul goes deeper into Jack’s pussy.

“Oh your dick feels so good inside me now.   Fuck me, Paul.”

“Fuck, your tight ass  is so fuckin hot.”

Paul picks up his rhythm and Jack starts to moan.

Paul is holding onto Jack’s red boots as he fucks Jack. 

“I love these red Chucks, Jack.  They look so good on you.”

Paul kisses them as while he fucks Jack. 

“Oh yeah, we love our Chucks, don’t we.  We’re Chuck buddies.”

Paul explodes inside Jack while Jack spews his cum on Paul’s chest.  OHHHHHHHHHH

“Wow that was so good Paul.  I love being fucked.  I am what they call a bottom”

“Yeah it was great, Jack; but not sure I want to do it again and become a queer boy”

Jack and Paul did not have sex again for sometime.  Jack would fantasize about being fucked by Paul wearing his high red Chucks and jerk off.  Jack was sure he was gay and just wanted to have sex with boys.    He would wait and see what Paul wanted to do.

To be continued.