Jack Squeezes the Cum Out of My Cock

 My Playroom—April, 2026

 

Jack checked in, wondering if I was up for some fun.  We set a date early in April.  I was really ready for him.  I hadn’t gotten off that Saturday night, detailed in the last post, and was feeling it.  Finally, four days later, I knew I’d get rid of that excess cum…

 

Jack is naked and sitting on the bed, jerking his ample cock to the porn orgy happening on the television.  I hang up my robe on the doorknob.  I take a sip of my tea and stand in front of him, presenting my mounded cock hidden by my discolored yellow jock.  He pulls me closer and nuzzles the fabric.  He groans and begins to lick it.  He loves the taste of sweat and cum and who knows whose ass jizz on the fabric.  He gets it very wet, reactivating the juices dried into it.

Eventually, he pulls it aside to get to my dick.  My cock springs free.  He uses his hand to guide it to his hungry mouth.  He licks the drooling head before swallowing three quarters of the shaft.  He pulls off, takes a breath and takes every inch I have to offer.  He stays there for a long moment, then comes up, gasping for air.  He gulps—and does it again.

This time, once he’s caught his breath again, I begin to fuck his face.  I hold onto his ears and jack hammer my cock into his mouth and throat.  When I sense he needs air, I let go.  He grabs some—and goes right back to pleasuring me (and himself.)

“I need to eat your ass.”  It’s the truth.  I can’t wait.

He gets up on the flattened fuck bench.  I kneel behind him, slather my cock with coconut oil and jerk it as I begin to lick his puffy hole.  I burrow deep into his pronounced pucker.

“Fuck me…”

I take the cue.  I stand up and slide into him.  He feels tremendous.  I bottom out, hold and begin a slow in and out.  I build the speed.  My hips slap his ass as the force of my fuck increases.  Abruptly, I pull out and take the few steps to his mouth.  He licks me clean, loving the taste of his ass on my cock.

I go back and fuck him again.  He cleans my cock just as thoroughly, but this time I bend down to kiss him, wanting to taste all those juices myself.  His tongue gives way to mine.

We move to the sling.  I eat his ass for a long time once he’s situated in it.  Eventually, I stand up and fuck.  His ass is more open, but he knows how to work it.  He squeezes down on me at random times—and I love it.  I pull out and he cleans my cock once more, craning over the side of the sling to get to me.

Another fuck.  Another clean.

“Let’s get you out…”

He dismounts—with no help needed from me.  He grins as I take his place.

“Now eat my ass…”

He kneels and begins a teasingly slow lick down my entire ass crack.  The moment he zeros in on my hole, I crack open the poppers I save for this moment.  Jack loves rimming me.  He’d lost his erection during the fucks, but he is rampant now.  He licks my balls, my cockring, my perineum and my hole.  He grunts out his enthusiasm.  

I readjust the stirrups, so they go from my knee to the D ring on the sling by my head.  It tilts my ass up.  It gives him a whole new angle to work.  I swear his tongue is inside me even deeper.  I take another hit—and stop thinking...

*

Jack is back in the sling and I am fucking him.  I tell him how good he made me feel.  I pull out and eat his wet, glistening hole.  I want to go deeper.  I stand up and set up the rimseat.  Jack gets out of the sling as I lay down the mat for the rimmer.  He gets on it, head under the seat.

“I got this out for me to do you,” I chuckle.

“Let me lick you first.”

I sit down.  He goes to town.  I watch the porn and idly stroke my cock as Jack’s tongue goes even deeper into my body.  He makes the hottest sounds as he penetrates me.  This time I don’t use the poppers.  I want to save them for when I go under Jack.  I sit there, enjoying his handiwork for quite a while.  I finally suggest we switch.

I stand and we change places.  I take a hit before he sits down.  His wet hole is pulled open for me by the seat.  I begin to explore.  Deeper and deeper.  Jack’s moans are just what I want to hear.  I stop jerking and concentrate on giving him as much pleasure as possible.  I can’t believe how deeply I can probe into him.  My breath quickens.

I am not down there as long as I’d like to be.  The need to breed his ass hits me hard.  I tap his thighs.  He stands up, lending me a hand to get to my feet.

“Sling or bench?”  he asks.  He knows just what I need to do,

“Sling.  I love watching your face as I shoot.”

He jumps in, feet on chains, no time for stirrups.

I push right into him.   My cock feels like every nerve is firing.  I begin to thrust.  Fast and deep.

“Give it to me!”

I quicken the stroke.

“Breed me!” he moans.

“Say it again…”

“Give me your load!”

I thrust again just as he finishes.  My cock erupts.   I fire off jet after jet of hot cum as I grab the sling frame and hand on.  The moment I finish, Jack begins to milk my dick, squeezing down on me for every last drop,,.

A Tame, but Pleasant, Saturday Night

 Near Home—April, 2026

 

When cruising, sometimes everything goes right.  Other times it feels like everything goes wrong.  This first Saturday night in April walked a middle ground.  Nothing earth shakingly good; nothing to scar my psyche either…

 

I arrive around 7:30pm.  I am the only guy here.  No, that’s wrong.  There is a man in darkest corner scrolling through his phone.  I take out my dick and stroke.  He scrolls, never looking up.

The door finally opens.  It is a straight couple who sit on the short wall, which makes them look right at me. 

“Look, honey, he has a big ole dick for you…”

She looks at me again.  “No way,” she stage-whispers—as if I can’t hear her.  They watch the straight porn.  Eventually she fellates the man who brought her.  He cums demurely in her mouth.  They leave.

I stroke.

New men come into the room.  Five of them.  One of them is a beefy Latino I have watched here many times, but I don’t think I’ve played with him.  He starts making the rounds of the room.  He sucks each man (but phone guy).  He always stops before the guy can unload, standing up and going outside for a cigarette.

When he comes back this last time, he kneels in front of me.  He edges me close to shooting—this time standing up and never returning.

I stroke.  The other men filter out.

The guy I have known longest from this place comes in with his husband.  They walk to chairs near the gay screen.  They chat a little—judging the men in the video.  I finally want them to shut up, so I sit in a chair in front of them.  In moments, the guy I know best has stripped down and has his dick in my mouth while I am being given head by his partner.

I love being serviced with a cock in my mouth.  I groan quite a bit.  My friend starts fucking my face.  He isn’t using poppers tonight and his dick is rock hard.  For the first time in my presence, his partner pulls his dick out and strokes himself as he sucks me.

We only stop when his partner’s knees tire.  He sits, down.  His dick, now semi-hard, is lolling against his jeans.  I get up.  I have never had him in my mouth before.  He’s thickish, with some extra skin, though he’s not uncut.  He moans as I suck him.  My friend sits down and strokes to the scene.

“Stop—I don’t want to cum,” he murmurs.  I let his cock go and go sit down again in my new seat.

The three of us stroke.  Phone guy has taken off sometime during our threeway. A new man comes in.  He sits near us.  He takes out a beefy dick.  He looks like the coach you had a crush on in high school.

I am ready to stand up and ask if he wants head as he is exclusively watching the gay porn.  But my friend’s partner beats me to it.  It’s not a quiet suck—and that hot.  I love to hear the slurp.  Soon, I have my friend’s cock back in my mouth.  ‘Coach’ likes the view.  My friend places my left hand on his ass.  It’s lubed now—and I can burrow a finger inside him.  I idly wonder if I can fuck him in front of the partner…

At that moment, the ‘coach’ gives up his load.  That makes my friend shoot down my throat.  They all clean up a little—and take off.

I am alone again.

I wait ten minutes.

No new arrival.

I go home, mostly content…

History: Man's Country 1991

 It’s time for another stroll down my personal sexual history.

 

1991

“I better get some fun in now as no one will want me once I hit 40!”  To think that I believed that at 35.  But it is exactly what so many gay men thought in 1991.  Little did I know how good my 40’s, 50’s and 60’s would be.

I remembered the name of Man’s Country as the bathhouse my brother loved to visit.  I didn’t really want to tell him I wanted to go.  So where was it located?   No quick internet search available. And Chicago was huge.

Somewhere along the way I had seen an ad in in one of the glossy gay mags for Bob Damron’s Address Book.  I made a special trip to Border’s Books in Ann Arbor, knowing they had a miniscule gay/lesbian section, to see if it was there.  It was.  It became my reference book for everything gay in whatever city I visited.  They listed, bars, bathhouses, men’s health services, adult entertainment, bookstores and cruisy areas.  All reported by gay men for gay men.  The book got tucked under the front seat of my car and stayed there, only moving each time I got a new vehicle.

I found Man’s Country fairly easily.  (I’d always been good with maps.)  I sat in my car, parked on a tiny, dark side street and took a deep breath.  I went in.  The guy at the window could not have been nicer.  He issued my membership card with a smile.  I knew I wanted a small room, so I could lock myself away if I felt like it.  I think it was an eight-hour time limit.  I was arriving at 10pm.  Perfect.   He told me how to find my room amongst the warren of corridors and doors.

I found it, stripped and with my towel tightly tucked in and my key on my wrist, I went to explore.  I carried a small shaving kit packed with lube, condoms and poppers.  I went back to the locker room.  I really stopped and looked at the murals by Etienne.  I had never seen anything like them.  Gorgeous.  I found the stairs and went down to the wet area.  More rooms were down there, too.  I sat in the dry sauna.  Two guys came in.  They instantly began to take turns sucking the other’s cock.  I was mesmerized.  I tented my towel.  Soon, I was openly stroking to them.  One of them looked over at me and smiled.  I suddenly felt more at ease.  One got the other off.  They left, giving me an approving nod.

Heartened, I found the huge dance floor and stage.  It seemed to be more about guys chatting and napping than dancing.  I learned there were weekly strip shows there.

I walked the endless maze of rooms.  Some with doors open.  Many closed with sex obviously happening behind them.  I quickly figured out guy’s ass up vs lying on their back and stroking their dick.  I was invited in to a number of rooms, but I wasn’t quite there yet.

There was a dark room.  I hung out near the opening, in the room but still in some light.  I ditched the towel and openly stroked as I saw countless men disappear into the pitch black.  Delicious sounds of moans and groans came from within, but I didn’t go in any farther.  Not tonight. 

Music blared from the dance hall.  I went up and watched three men strip.  They were hot, but stripping for men who were all but naked themselves made me shake my head.

I went back to my room and sat on the hard wooden box with the wafer-thin mattress they called a bed.  What was I going to do?   The jury was still out on the safety of oral sex.  I really wanted to fuck anyway.  I went down to the basement.  All the rooms were taken now.  And here, almost all the men were on all fours, asses pointed right at the door.  I made the circuit twice.  I couldn’t believe that most of these guys never looked over their shoulder to see who stepped into the room to fuck them.  At the end of the hall, was a man with very hairy ass, likely in his thirties.  His ass was perfection.  A gorgeous mound of flesh and fur.  I went in and closed the door.

“Fuck me,” he muttered.

I suited up and did just that.  It was great.  I stopped, just short of cumming.  He was moaning, egging me on.  He finally looked over his shoulder.  “That’s a lot of meat on such a skinny guy.”  I beamed as I left his room.

Even better, there was no shit on the condom.  I was thrilled.  I fucked another guy.  Same thing.  The age of cleaning out had happened and I didn’t even know.  (When I mentioned this later to my brother, he credited the porn guys of the 80’s when, in their countless interviews with In Touch, Blueboy, etc, they talked about how they cleaned for the skin flicks. And gay men everywhere took it to heart.)

I wanted more.  I made a tour of the guys upstairs, too.  Always with a new Magnum in place.  At least one guy asked me to ditch the latex.  I fled.

I napped in my room.  Not really sleeping as my head was full of the butts I’d stuffed.  Around 3:00am, I made another tour.  Many doors where now shut, but there were lots that were open—and many sported new recruits who’d checked in after the bars had closed.

I didn’t fuck any of them. 

I checked the dark room—and went in a little deeper.  A hand tried to pull the towel off me.  I had an inner freak out and left.

On the other side of a lounge near the dance hall was the lone sling room in Man’s Country.  The door was open.  I’d seen slings in videos but never used one.  A hot guy was in it.  He looked right at me and waved me in.  I got hard instantly at the shape of his ass and the obvious use of his hole which had very pronounced ass lips.  I suited up.

“Fuck me as hard as you can.”

I did.  For a long time. 

“Don’t cum in the condom.  Cum on me!” 

I was finally close.  I ripped the condom off and aimed for his ball sack.  The force of my shooting covered his abs instead.  He sighed contentedly.  He now instructed me to put a latex glove on my left hand.  I found the box on the small table next to him.  I did.  Curious. 

“Dip it in the tub of lube.”

I did.  I brought my hand close to him.

“Now use your fingers.”

I did.  One.  Two. 

“More.” 

Four went inside him.  Instinctively, my thumb went to my palm.  He reached down and pulled my hand forward.  It slid right into his ass, his sphincter snapping shut on my wrist.  I had never had a feeling like this before.  Not to mention the mind fuck that my hand was buried in his hot butt.  He instructed me to pull out and push in again.  I was tentative to do it, so he pulled me in a second time.

Then I got it.  I began to really fist him.  He shuddered, telling me to keep going.  That I was doing just what he needed.  He scooped up my load and licked his fingers—and suddenly his whole body convulsed as I witnessed my first assgasm…

*

I checked out with a new clerk.  Right on time.

“Your membership card.  Take it or leave it here?”

I opted to leave it there once he told me many men did that.  “One less thing in your wallet,” he smirked.

I went to my car elated.  I was suddenly tired and slept in the front seat until I felt I could get a late breakfast and head home…

*

Speaking of cards kept on file….

The next time I went back to Man’s Country, I told the attendant my membership was on file.

He pulled out the big recipe box they were stored in and asked my surname.

I told him.

“Here you are,” he said, lifting out a card.  He read the full name on it.

I blushed a deep red and said, no that was my brother.

His jaw dropped and then he began to laugh as he found my card and proceeded to check me in….

Stretching His Hole: Round Three

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"May I Suck that Beauty?"

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Equipment Close-up: Spades

 Equipment Close-up:  Spades

 

As I have very little time to write today, I thought, after my convoluted description of this toy in the last post, I should do an Equipment Close-up of the Spades…

 

This toy was given to me by Jack, when he and I were playing regularly a few years ago.  It sat in the box—and it got ignored in favor of my cock.  His work took him away—but I finally opened the package and got to use it with another man.

I don’t have many toys for men who are inexperienced or even at the intermediate stage.  This one really fits that bill.  It is a nice variation to balls on a string.  The spade shape goes in easily and smoothly with a nice snap shut of the sphincter around it. It is just shy of a 2-inch diameter at the large end.  All five spades are the same size.

The entire length of the toy is 12 inches, with an insertable length of 8.5 to 9.  The handle is easy to grab when my hands are greasy during fist play.  The men I have used it on all take three of the spades and a couple of guys take four.  I have yet to get the fifth into a good pig…

 

I’m glad I finally got it in use.  Now that Jack is back in town for a bit, I need to remember to get it inside him…

Here is their webpage:  Themaster-series.com

  And the page:  Spades ::: Master Series

Finding Blake's Second Hole

 My Playroom—March, 2026

I had one last meet in my busy March.  Two days after my cocksucking extravaganza detailed in the last post, I had a bud come to the playroom.  Blake, the very tall man around my age (and with a terrific beard) needed me to work his ass.  I was happy to oblige…

 

I come down the stairs to the playroom, where I’ve sent Blake to strip.  I open the door to find him sitting on the bed, watching the porn on the flat screen.  I hang my robe on the doorknob.  I cross to him, my used yellow jock now inches from his face.  He leans in, his nose rubbing the fabric.  Soon, it’s pulled aside and I hardening up his mouth.  His tongue is all over me—and it feels terrific.  Once I’m fully, achingly hard, I fuck his face for a moment.  But I am really eager to eat his ass.  I tell him to get up on the flattened fuck bench.

He does, looking hot on all fours.  I kneel and lick down his ass crack.  I zero in on his hole and begin to work it open.  I hear Blake groan.  I tongue fuck him.  Harder.  And deeper.  I stand up, lubed with coconut oil.  I push in.  And miss.  He has a tricky hole; there is another indentation I keep aiming at…but I finally get in and sink my entire cock length into him.

I begin to fuck.  His hole opens rapidly, as do so many men who take fist.  I can now pump into him harder and faster.  I grab the Ballistic Butt Bomb.  Still in his ass, I lower the toy into the lube bowl on the floor.  I bring it up and coat the end with my left hand.  I pull out and push the metal toy into him with a circular motion.  It goes in slowly, looking hot as fuck.  My hard cock follows.  I love the stainless steel under me and the solid ball my dick head is plunging against.  Blake’s eyes are on the mirror to the side, watching his ass be violated.

I pull out.  Then the toy.  I re-lube and twirl the BBB into place again.  My cock follows.  I fuck him again, this time with my hard cock battering the stainless-steel deeper into his butt.  When it’s as deep as I’m comfortable pushing it, I pull out and set the toy under the sling.  I’m sure I’ll be using it later.

Blake gets in the sling, his long legs on the chains, not the stirrups.  I kneel and eat his hole once more.  I fuck him again, before going to the shelf and grab a version of balls on a string.  Instead of balls, this toy has ‘the balls’ shaped like a spade, so it is a series of mini-butt plugs connected together.  I grease it up and insert, working each plug in and moving to the next.  He takes two, this first time.  I pull them out, watching his hole flower open to release each spade.  I re-insert.  He takes a third one this time.  I pull them out.  I watch the concentration on his face as each mini-butt plug opens his hole on it’s exit.  He sighs in satisfaction as the last one escapes. 

I fuck him.  With my dick.

Now I fuck him with the clear dildo with the handle.  The gentle curve of the toy is just a little thicker than I am.  I replace the toy with me.  Now the toy.  Back and forth.

Soon, the eggheaded dildo is lubed and inside him.  I pull it down and add my cock.  Well, just the head for a moment.  Then he relaxes and takes the rest of me along with the toy.

It’s time for the main event.  I kneel and grease up my left hand.  Then the right.  The fingers of the left slip into him easily now.  I rotate the hand with my thumb pressed to the palm and I’m suddenly inside him.  I move my hand the tiniest bit.  Blake pants, nodding at how good it feels.  I pull it out, re-grease and do it again.

Now the right.  He takes my bigger hand just as easily.  I go back and forth between them.  I try adding my cock with my left hand inside him.  I can just fit the head of it on my palm.  I don’t try for more.

I give my hands a break and use the Seahorse on him.  Blake takes it easily.  He especially loves it with the curve going down.  The small head of the toy has invaded his second hole.  I can see it in his eyes.

After the toy is out, I follow up with my left hand.  I keep it flat and open, inching deeper and deeper into him.  Now my middle finger is touching the same bend.  It makes him shudder—and he tells me to keep it up.  The slightest movement makes him squirm and moan.  I am standing to do this, to get the right angle.  My head rests on his abdomen as I worm my way deeper into his guts…

*

After a mini break I go through all the same toys with him once again.  Spades, clear, egghead, Seahorse…

Now it is back to my hands.  Once again, I am inching into his second hole, teasing the opening with now two fingers.  His body shakes, the feelings are so intense.  I pull out and then work into him once again, with my head on his abdomen, almost like I am listening to my hand’s progression through his tract.  Success.  I tease the opening as Blake takes deep breaths.

His hole is tiring.  We take a longer break.

“It’s done with hand, but not your dick,” he murmurs.

“I know just what you need to soothe your insides,” I smirk.

I grease up with coconut oil and begin to fuck Blake in earnest.  In no time at all I am soothing his guts with my cum…