Jake: Deeper and Deeper

My Playroom—May, 2018

My summer workload was to start the moment I came home from IML on Memorial Day.  I knew I was packing the sling for the piss party there, but I thought I’d get a start on packing up the whole playroom before I left.  Just as I was getting out the big suitcase for the rimseat and towels, I got a message from Jake, the fisting bottom I’ve known longer than anyone else on my current list of fuckbuds.  He was traveling home from the east coast and wondered if we could arrange a meet on his way home. 

I stopped packing and set things back up.

Jake looked a little tired when he arrived, right at when I’m usually sitting down for dinner—but tonight I had a different kind of meal in mind.  He hopped in the shower and looked refreshed when he came out.  He went up to the playroom and I went to my bedroom to put on my jock and boots...

Jake has put on the wrist restraints that hang from the chains.  I make a mental note of it to use them later.  I let him suck my cock to full hardness.  It doesn’t take long.  I have been thinking about this all day—one of the reasons I love to plan ahead.  I point to the fuck bench.  I want to bury my face in his ass—the ass I am going to use in so many ways tonight.

My tongue goes inside him.  He’s still warm and damp from the shower.  I leave behind generous amounts of spit.  I want as little artificial lube as possible for the first fuck.  I stand up and insert.  Jake gasps and opens the poppers.  The vapors open his hole.  I am fucking into his now juicy ass at full strength.  I pull out and walk the length of the bench to his head.  He doesn’t need any words to convince him to taste his ass juices on my dick.  He licks me clean. Hungrily. 

I plunge back into his ass.  I fuck him hard.  Eventually, I slow and pull out, offering him my cock once again to spit polish.  When I go back to his butt, I grab the egg-headed dildo and work that in first.  My cock travels down the ribbed shaft of the toy.  It has tightened his hole right back down to the feel I had when I began.  I fuck happily as Jake huffs more poppers.

I pull out and reach for the fairly large black butt plug.  It takes a moment even for this most accommodating ass to make the final stretch before it pops shut around the core of the toy.  I stretch him a little more—working at adding a fingertip in with the toy.

I fuck him some more.  Hard enough to get a groan or two out of him.

I grab the big black toy that reminds me vaguely of a Christmas tree, with its progressively bigger ridges for his ass to close around.   It gets sucked in.  My fist taps on the end—making it shake and move deep inside Jake.  There is no way I can add any of me into him with this toy—it’s that thick.

I now beat the end of the toy sticking out of his butt.  Jake groans.  I pull it out and fuck him on the bench one last time.

We move to the sling—but I unclip the lower end of the sling and let it hang by just two chains.  At the free end of the stand, I clip the restraints on his wrists to the hanging chains above his head.  I get the spreader bar and fasten the ankle restraints on either end of it to him.  I take the leather blindfold and buckle it around his head.  He is helpless.  And loving it.

I grab his nuts and pull the sack until it is as tight as possible.  I slap it with my open hand, again and again.  I use the leather paddle on them, too.  I move to his plump nipples.  I twist one.  I bite one.  I want to make sure that he doesn’t know what is going to happen to him next.  I go back to his balls.  I even suck his plumped, but not hard, cock for a bit.

I move around behind him.  My hard dick finds his ass crack.  I reach around and twist his nipples some more.  I kneel and paddle his ass, then begin licking it—needing to pull his cheeks apart.  I paddle the wet cheeks once more.  I want to piss his ass crack, but I haven’t drunk quite enough tea to make it happen.  I settle for fucking him roughly.  It feels totally different with him standing and being made to take it…

*****

Jake is in the sling.  I have eight fingers in him.  I do a wide lateral stretch.  Hold.  Pull both hands out.  He’s ready.  My right hand glides into him.  Now the left.  Back and forth.  Sometimes with my thumb up.  Sometimes twisted so my thumb is down.

Now it goes in thumbs up and I turn it 180 degrees deep inside him.  And back again.  The right hand now does the same thing.

I repeat the toys. 

I fuck him a little more—but his ass now needs bigger things than my dick.

The speculum is lubed and inserted.  It’s cranked wide.  I play with his prostate.  I stroke it, over and over.  He tells me to pinch it.  My fingers find it again and I do as instructed.  Jake writhes in exquisite agony.

I stick my dick in him one last time.  I feel the blend of metal and flesh on my cock.  I fuck, pull out and go back to toying with his prostate, making his dick drool.

With the speculum out, my open right hand goes into him again.  Slowly.  It’s crawling deeper and deeper.  I find his second hole.  My middle finger pokes through.  I stand up.  I keep up the pressure and bend my hand so he can take another finger.  It’s as deep as I’ve ever been in him.  My cheek now rests on his belly.  I can feel my hand move inside him.  I keep moving forward.  Millimeter by millimeter.  Barely moving—but always with a slight forward push.

Jake signals he needs me to back off. 

I do.

But I go up him again.  Every bit as slowly and just as deeply.

This time he calls a halt.  His ass has taken more than I’ve ever given it.

We look at the clock:  three and a half hours of ass play.

We go off, well sated, to dinner.


Jake has also written up his version of this play session.  It is scheduled to be published in 24 hours.