Tuesday, October 7, 2014

A Medium Fist

My Playroom—August, 2014

He was coming a distance—from another country actually.  Business brought him to Michigan, but he was willing to travel even farther into the state for some play time.

“I am making my annual trip into Michigan to see friends,” Greg wrote.  “The sight of a sling drives me wild! I’m likely too vanilla for you…but no harm in reaching out.”

My house guests were gone.  The house was mine again.  I needed to get the playroom up and was itching to use it after the long summer hiatus.  “Sometimes vanilla is good,” I answered, “so you appreciate the other even more…”

We talked dates.  And limits.

“I do like to be fisted,” he closed with (as we’d met on Asspig) “but I have only taken a small hand.  You might not get your medium ones all the way in.”

There was only one answer to that.  “I’m a patient man.”

Greg is taller than I expect—though his height of 6’2” is right on his profile.  He is almost exactly my age, though I think he looks younger.  He has a trim waist, a very regulation sized dick and, what I really care about, a nicely rounded and firm ass.  I watch him step into his jock, with his back towards me.  He pulls it into place.  Sigh.  The straps frame the mounds of his ass perfectly.

I suggest the bench.  Grabbing his poppers, he climbs right into place.    I kneel and dive in.  He’s tight.  I pull the cheeks apart.  My tongue worms its way into his pucker.  I spit into his hole and push it in deep.  Again.  And again.  I push my right index finger into him.  It glides in smoothly with all the spit.  I add the one on my left hand.  A lateral stretch makes him groan in delight.  I hear the bottle cap open.

Fingers out.  Back to tongue.

Fingers in.  Spit.  Rim.

I condom up as I eat out his hole.  I have agreed to play covered.  I over-lube for the drag of the latex.  I stand.  He reaches back to feel if the Magnum is in place.

“If I say I will wear one, I will.” I snap, sounding a little more testily than I mean to sound.

I push in.  He’s tight.  But I get it into him on the first try…


I have to stop fucking.  I have been going for almost ten minutes, but my dick is telling me how much it hates being hermetically sealed in that Ziploc bag.  I pull out.  I use the egg headed dildo.  There is no question of my adding my cock along with it; I can barely pop the bulbous head of the toy into his hole.  But I do.  I slide it all the way in.  I add some fingers around the smaller shaft.

The cap unscrews again.  I do a few lateral stretches with the toy in place.  And work the toy all the way out and back in.  This time the over-sized head pops smoothly into his hole.

“Let’s get you off your knees.”

I help Greg off the bench.  He stands a little unsteadily. 

He grins at me and says only one word. “Wow.”

We move to me under the rimseat.  At first I’m disappointed that all I can taste is the latex from my condom.  But soon I’m back to tasting him.  My cock stands back up.  Now rampant.

I eat and spit.  Tonguing him deeply.  I hear the cap again. 

After the hit, he’s becomes verbal.  Telling me to tongue fuck him.  To eat his hole.  To push it in there deep. 

I do all those things.  And go deeper than a tongue has likely ever gone up his hole.

Greg is in the sling.

I make one more attempt at latexed fucking.  It starts fine, but my dick rebels again.  I give it up and just tuck the only slightly engorged meat away into the wet jock.

I don the black nitrile gloves.  And slather on a lot of Crisco.  One, two, three fingers to the knuckle.  Now four and five.  I’m right at bridge—the knuckles won’t quite go.  I repeat with the left.  I do a four finger stretch that makes him babble joyfully.

I spend a long time cranking him open with the speculum.  I show him the progress of his widening hole with a hand mirror.

I go back to hands.

And suddenly, when I try a second time with my left hand, I’m all the way inside him.  He can feel the snap of his hole around my wrist.  His eyes open.  He can see it in the mirror above.


I give a slight turn of my encased fist.  I hold it in place and then pull out.

In no time, with just a little pressure, he takes my greasy right hand as well.

“That’s the bigger hand,” I remind him.

He’s open now.  I don’t try for any depth.  I am glad I got him a step up in size. 

We play for almost three hours.


Greg is gone.  Back to his local motel so he can get an early start on his long drive in the morning.
I type up a few notes.  I like the guy.  I like the hole play. 

But then there is my cock deciding for me how much it now hates wearing a Magnum.  Just a few years ago, I used to play for hours suited up without any problem at all.  I know better than to say “never again.”  But I also know it will be a long time before I agree to a safer hook up.  I wonder how much Greg noticed or cared that there was not much fucking…

I needn’t have worried.

He wrote a glowing review about our long hours in the playroom. 


  1. luv your adventures, you've made me more open to more out of man sex. Thanks