Chaining Up Jake

This summary is not available. Please click here to view the post.

The Bucket List

A group of people I was working with began talking about their bucket lists.  The group came up with lots of the usual—world travel, things to accomplish in the next 10 years, watching whales from cruise ships, etc. 

But when I came home that night, I began thinking about my sexual bucket list.  I realized I am in a very good place with that.  I have done just about anything and everything I want to do.  There is extreme stuff I have never done, but I have little desire to go there just so I can say “Well, I have branded one guy.  The sizzling flesh didn’t do much for me, but he got off on it.”

There are sexual venues I would like to visit.  321 Slammer, the infamous sex club in Fort Lauderdale, would be at the top of the list.    Likely finally ending up at Wet N Hot, the huge piss party in Palm Springs, is another.

But for sex acts, there is one thing I would love to try…

I would love to have an orgy of 6 to 8 men where we are totally covered in lube.  The porn that inspired it is a fisting video (the Fisting Underground trio from Dark Alley.)  It would be great if fisting was on the menu as well, but I’d be happy with a bunch of versatile men who are slipping and sliding as we fuck.  The practicalities of where to do it and the clean up makes it not likely to be fulfilled immediately, but you never know…

So think about it…what’s on your personal sexual bucket list…???

A Quick (But Juicy) 40 Minutes

My Playroom—March, 2025

 

Kieran, the married cocksucker, was horny.  He let me know.  Repeatedly.  The texts just kept coming.  He has only two days in the week he can sneak away.  Unfortunately, I had them booked.  But I told him I could play either of those days the next week.  He instantly set the date and time.

On the designated day, he parked in my driveway five minutes ahead of schedule.  I was ready with all the towels in place and the lube laid out.  We chatted as we walked down the steps to the playroom.  I asked if he had been to the bookstore lately.  (It is where we met.)  He hadn’t.  He wasn’t a huge fan of the new set up all in one room (which I kinda love.)  And he hated how the gay couple I often see there got to everyone he was interested in before he did (which made me sorta smile.)

He stripped down to athletic socks and sat on the bed…

 

I hang my bathrobe on the doorknob.  I have put on a jock that has not seen much service.  (It’s been handy to keep at least one fairly scent free.)  I stand before him.  Kieran twists my cock out of the pouch.   It plumps in his hand.  It grows hard and sturdy in his talented mouth.

I idly play with his hairy chest as he licks my cock head.  His tongue swirls round and round it.  My piss slit begins to drip precum.  I look down.  His short cock has hardened, pulling back the foreskin.  His left hand begins jerking and squeezing it as he sucks me.

To vary things a little, a begin a slow face fuck.  Kieran takes it willingly.  I can tell he likes it as his hand on his dick moves faster.  I build up the speed.  I stop, deep in his throat and he takes over.  He pulls me back out and his tongue is all over my head and shaft.  Finally, I pull it totally out of his mouth. 

“Balls.”

I take a step closer to him.  I hold onto my cock and give him access to my nuts.  They pull up a little as his tongue flicks over them.  He carefully sucks each in turn into his mouth—the suction gentle, the tongue caressing.  He licks the bottom of my cockring.

“Let me have that cock again.”

And he starts all over again.  He is in no hurry to get his ass pounded today.  He sucks.  He deep throats.  He goes back to my balls.  I am on the verge of asking if I can lie down on the bed so he can continue that way, when he says “I better get in the sling or I’ll shoot.”

He gets up on the sling and I get his ankles in the stirrups.  I kneel and taste his hole.  He has been busy with his toy at home, for his ass lips are very pronounced, even before I work on them.  I burrow in, loving the feel of the swollen flesh on my tongue and, eventually, in my mouth.  He moans.  I am more than ready to fuck, but I spend a few more minutes with my tongue in his ass.

I stand up and push in.  I watch his face.  As he relaxes, I begin to saw in and out.  Slowly.  Deliberately.  His eyes are on the mirror above him, watching my cock open his hole.  Kieran reaches for his own cock and then thinks better of it the moment he touches it.  He lets go and closes his eyes to concentrate on the fuck.

I pull out and go to my knees.  I hungrily take those swollen ass lips into my mouth.  He sighs and I moan.  I tongue them, loving the freshly fucked feel of them.  His asscunt is juicy—and I spend long minutes fucking him with my tongue.

I stand up.  My cock is freshly lubed.  I plunge into him.

“Fuck, you feel even bigger…”

And I think I am; the tongue fucking has gotten me really, really hard.  His hand goes to his dick.  I increase the speed of the fuck.  Kieran squeezes his oozing dick.  Repeatedly.

“Oh, hell….” And he shoots.

I slow down.  I know from experience he can’t take a fucking once he’s shot.  I swipe my hand through the puddle of his cum.  I smear it on his hole.  I go to my knees and begin eating his ass again.  I suckle on those cummy, full ass lips.  And jerk.  I surprise myself and think I might just get off this way.  I keep working and finally manage to get both of his ass lips into my mouth at the same time.

Bingo!

I stand up and slide into him easily.  In three or four strokes I am filling his ass with my seed.  Kieran is surprised—and pleased.  I marinate in his ass a bit, before reaching for a towel…

I glance at my phone.  Forty minutes from start to juicy finish…

Showing Off for an Audience

 Near Home—March, 2025

 

You would have thought I would be sated after my terrific time with Keith.  Seemingly not.  The next day I went in search of more fun…

 

I arrive after lunch.  I walk into the theatre space.  I join seven other men.  I don’t know any of them.  I pass a very handsome Latino in his early 30’s leaning on the wall by the restroom door.  He is watching the straight porn avidly and groping a mound in his trousers.  A Black man is at the corner near the Latino.  He has his dick out and is stroking it.  Two cubby men are doing the same, but nowhere near each other.  The other three are kneading mounds of cock and balls still covered by their pants. I sit in my usual spot and take out my erection.

All the men are now eyeing each other, except the Latino. He has proceeded to take out a long, thin dick and jerks to the screen where a hung guy is fucking between a woman’s massive breasts.  The rest of us are glancing at the screen and at each other.  No one is ready to make the first move.

I stroke and decide enough is enough.  I nod to the slightly shorter cubby guy.  He responds by standing up and kneeling in front of me.  He swallows me down.  It’s nothing special, but it breaks the ice for the day.  The Latino leaning on the wall can’t seem to believe sex is happening right in front of him.  He tries to keep looking at the screen, but keeps turning his head to watch us, too. My cocksucker tires fast.  He gets up and sits down in his place.  He jerks his dick furiously.

I look at the other cub.  A little younger and a little plumper.  He nods at me.  I nod back.  I beat him to the draw and get up and suck his regulation sized cock.  In moments he pleads with me to stop.  I do.  We reverse.  I sit in his seat and he sucks me until he shoots on the floor.  I get up, letting my hard, wet dick swing free, and go to the restroom to piss.  The Latino can’t take his eyes off it as I pass.

I piss and come back out, passing the jerking Latino again.  “Damn…” he whispers.  I smile at him and sit back in my regular seat.  I watch the shorter cubby guy get up and head to the restroom.  On his way back, the Latino stops him and they have a long, whispered exchange.  When they finish, the cub comes over to me.

“That guy,” he tells me, gesturing with his head, “wants to watch me suck you. That ok?”

“Sure.”

He kneels and takes me in his mouth once again.  The Latino is now watching us, not the video.  He stays at the same wall, jerking his larger than average cock.  The guy sucking me is fine, but the idea that we’re doing it to please someone else really elevates it.

The Black guy, who has never looked at anyone, suddenly stands up and shoots on the floor.  He leaves, vacating the chair nearest where the Latino is standing.  “Why don’t we give him a better show?  Let’s move closer.”

The Cub likes this idea.  We go over.  Now the Latino can stand near his wall and be right over my shoulder to watch everything.  I hear his hand on his juicy dick.  It makes hot squishy noises on each stroke.  The Cub is really getting into the blowjob.  He sucks and licks, constantly pulling off me to show the Latino the size of my cock and how deep he just took it in his throat.

A new guy comes into the room.  He is mid 30’s, white and with a pronounced receding hairline.  He sits next to me, taking out his dick and jerking.  He soon asks the Cub if he can have a turn.  I am surprised when he agrees.  He makes room for the new guy, who is a little younger and, it turns out, a better cock sucker.

The idea of a new man on my dick makes the Latino work his own dick faster.

I ruffle the hair of my new cocksucker.  I am surprised by the Latino bending down and whispering in my ear.  “I want to cum on your dick.  Yes?”

I nod.  “I’m sure one of these guys will lick it off.”

He nods repeatedly before he says “But not yet.”

The Cub wants back on my cock.  The new guy stands up and gives me his cock to suck while I’m being serviced.  Again, the Latino is beside himself that I am actually a sucking a cock right in front of him.  He beats his dick faster, if that’s possible.

I really love this scene.  It’s fun and slightly different.  And I love showing off.

The door opens.  In walks Road Worker.  He sees me and smirks.  He walks around the Cub on his knees.   RW strips off his pants.  Then his shirt.  He bends, jutting his butt out by leaning on the chair next to me.  “Put that cock where it belongs,” he rasps out.

The guy in my mouth moves aside instantly.  The Cub gets up, knowing intuitively I am going fuck. He stands next to the guy who was just in my mouth.  They jerk in unison as I stand up and smear lube on my cock.

The Latino moves away from his wall to get a better angle.  “Fuck his ass,” he whispers. 

I let Road Worker take a deep hit of poppers.  I push into him.  Just as roughly as the last time I fucked him.  He loves it.  His cock bounces as I fuck.

“Breed him,” says the Cub.

“Fuck, yeah!” says the new guy, stroking along with my thrusts.

“Fuck that whore.”  This is from a guy who has been here all this time and watched the whole scene.  The fuck has made him come over to us and take his dick out.  I look at the four men stroking to my fuck.  I pull my cock out so they can all see the length of it.  I shove it right back in, fucking Road Worker still harder.  And deeper.

“FUCK!”  Road Worker whines. 

“You want my cum?  I grate out.

He nods and fumbles for the poppers.  I slow down and let him inhale.  I speed up the moment the cap is replaced.

“Take it,” I mumble.  The thrusts speed up.  I am so close.  And I love having guys watch this so avidly.  And…I’m there.  I blast into his guts with I don’t know how many spurts.  I hold his hips as Road Worker shoots all over the floor, milking my dick with his ass, whether he wants to or not.  I close my eyes and hold him onto me until he stops shaking.

When I open my eyes, the floor is awash with cum.  I don’t know how many of my spectators shot…

But the Latino beat me into the restroom…