Stretching His Hole--Round Two

 My Playroom—November, 2025

 

I got a text from the man I met in early November, who is just beginning his anal journey. (He is the one who arrived with his homemade lube, a plethora of lube syringes and just about anything else I would need.)  He wanted to come back.  I thought he had said he wouldn’t be available until after Christmas, but here it was still before Thanksgiving. 

It took a couple of days to settle on a date, but he made it back to the playroom.  This time he arrived with nothing. After a quick check of his cleanout, we went downstairs…

 

He is totally naked today.  He has a nicely haired body—and I am pleased to see it and not the thermal underwear.  He gets into the sling.  I help secure the stirrups.  I have melted some coconut oil.  I find in my bag of tricks a lube syringe.  I suck up the oil, work the syringe into his asshole and fill it with the liquid.

He sighs.  “Do it again.”

I do.  The pearly liquid begins to drip out of him.  I finger it back into his hole.  He groans.  I make sure I play with his prostate.  His cock erects.  He tries not to touch it.  I pause to suit up.  Magnum on, I finger his hole once again, as with the other hand, I lube my latexed dick.  I stand up and slide in.  Slowly.  Opening his ass.  His eyes get big before he shuts them tight.  I hold for a good 20 seconds before I begin a slow in and out.  He takes it.  From how his dick is dripping, he likes it, too.

I pull out.  I finger him once again.  Now two fingers.  Switching to three fingers makes him moan.  I grab the egg headed dildo, one of my smaller toys.  I try to twist it into place.  Nope.  It’s a no go.  I reach for the tiniest butt plug.  This slides into him easily and he sighs in appreciation.  I tap the base with a finger, once it is locked in place.  He groans.  I hit it with the heel of my hand.  This gets an even bigger response.

I work it out.  His sphincter does not want to let go of it.  He enjoys the battle.  I get up and go for the clear dildo with the black handle.  It has a nicely shaped end that fits in most men.  I grease it up and he takes it in one steady entry.  He even tells me it feels great.  I work it in and out.  I take it all the way out and re-enter him with it.  He pants.

Soon I grab the discarded egg headed dildo.  It fits in him now.  And he loves the bigger stretch with the middle girth of the egg.  I go back and forth between the two toys.  His ass lips are filling with blood and looking hot.

It’s time for the speculum—something he knows and loves from owning the same type that I have.  I grease up the metal phalanges.  They are cool to the touch.  As I position the toy in his now slightly gaping hole, he gasps with the temperature change.  I work it in.  He sighs as it moves into place.  I begin the slow crank open.  Pausing after each turn of the thumbscrew.  He is moaning at the familiar stretch it is giving his ass.  I work his prostate with one finger after each turn.  As it gets bigger, I use two.  His moans are non-stop now.

I put on a new Magnum.  I stand up and slide into his open ass.  His cock is drooling like crazy.  I fuck him. 

“I can’t believe you fit in me with that in there…”

I smile.  I knock his hand away from playing with his cock.  He has already lasted ten minutes longer than last time.

I fuck.

I slow down and pull out.  I crank the speculum closed.

“Can I try the metal one?”  He is pointing at the Ballistic Butt Bomb.

It’s a bigger head than anything I’ve used on him, but he is open and relaxed right now.  I go get it and grease it up.  He pants as I put it against his hole.  I push, with a slight turn and it goes in.

“Fuck…” he moans. 

I stand up.  He’s shot his load.

“Can you keep going?”

He shakes his head.

I tell him that he’s increased his playtime today, from 30 minutes to 45.

He cleans up and is out the door…with a big smile on his face.

*

His first visit is here:  He Knew What He Wanted