Stretching Derrick

 West Michigan—January, 2023

I have known Derrick for around 20 years.  I can’t say that about too many of my sex partners.  I think we met at a sex party.  (Surprise!)  This was long before Jacob was in his life.  We played there.  We played at his house a few times…and drifted apart for a bit. 

It was Derrick who reached out to me once he was partnered.  Jacob loved assplay and was wanting to explore fisting and Derrick’s hands were too big.  Could I help—with my smaller, flexible hands?  I could.  And did.  And one of the most satisfying relationships of my sex life was born. 

It was hardly surprising that we got off track with covid.  But we have started up our Sunday afternoons again, about once a month.  And we picked up like we had never paused…

All this is to say I was surprised to hear from Derrick in the middle of the month as I was pretty sure Jacob was away with work.  Indeed, he was out of the country and had told Derrick to reach out to me for some play if he got randy.  Would I be interested?

I tossed a couple of toys in my bag and was out the door…

 

There has been a little small talk, but now we are stripped and sitting on the couch in the study.  A new slide show of kinky men, doing things to each other (or to own their overstretched holes) flashes on the big screen television.

“I really want to work some more on deep throating you.  I’ve been practicing.”

I nod.  “Sure…”

Derrick grins and leans down.  I turn slightly to give him a better angle.  My cock is taken into his mouth.  He lingers on just the leaking head for a long time.  Then he begins inching down my thick shaft.  He gets to all but the final half inch.  This from the man who used to choke on me at the halfway point.  Derrick comes up for air.

I stand up in front of him.  “This will be easier.”  My cock is at eye level for him.  He leans forward and gets over half of me in the first gulp.  I let out a little moan of encouragement.  Derrick moves and suddenly his nose is in my pubes.  He holds for a moment and pulls off me, gasping.  “Hot…” he mutters.

“Do it again.”

It is easier now.  He relaxes and takes me to the root.  This time, when he pulls up, he keeps me in his mouth and his tongue makes my drooling piss slit very happy.  Then, after a breath, he deep throats me again.  My hands instinctively hold his head in place.  I let go and he comes off me, panting, his cock now rock hard.

I go to my knees and suck him for a long moment.  It’s his turn to hold me in place.  He fucks my face a little, bucking up into me, before he lets go.  I stand back up and feed him my cock one more time.  This time I make him choke.  The sound turns us both on.

“I used to fuck your face on the guest room bed. Should we?”

We go down to the guest room on the lower level.  It takes a moment to shift some boxes, filled with Christmas decorations, from the bed to the floor.  Derrick lays down, his head hanging over the edge.  He is at a great height for me to staddle his head and lower my cock down his throat.  I start with just half my length.  I do a slow in and out, before building to a more rapid pistoning of his throat. 

I pull out.  “Lick my balls.”  I lower them into his mouth with a deep knee bend.  His tongue gets busy as I stroke my wet cock.  I stand up and put my cock back into his mouth.  I go a little deeper this time.  His eyes water, but he takes it.  Proudly.  When I pull out, he is gasping for air, but self-satisfied. 

Once he’s caught his breath, I pump his mouth once more.  On only one stroke do I give him more than three quarters of my cock.  He gags a little and I pull back.

Derrick motions with his hand he needs to get up.  I pull out.  This time we are both panting—and we agree to head to the playroom…

*

Derrick is in the sling.  I am on my knees, my tongue working his ass crack and hole.  I spit and leave copious amounts of spittle behind, all while greasing up my cock.  I stand for the first fuck of this session.  I slide in easily—and to the hilt.  My pubes, once in his nose, now grind against his hairless ass.  Derrick groans and closes his eyes.  I see him relax and I begin to fuck.  Slow and easy. 

As I can never access their toys easily, so today I have traveled with two of mine.  While still fucking, I grab the egg-headed dildo and grease it up, holding it where Derrick can see it being coated with lube.  I pull out.  The toy twists into him.  He grunts as the head of it, bigger than my own flared cockhead, opens him wider.  The thin shaft goes deep into his butt.  I push it down and my cock slides back into him, gliding over the ridges of the toy.  Now I fuck him, keeping the toy in place. 

“I feel so full…”

I nod and keep going.  I pull out and go in again, now so the toy is on top of me.  It’s a totally different feeling, still full, but the stretch feels tighter.

The toy comes out and my cock goes in alone.  I add a few fingers, too, my left hand gliding over my slick shaft.  I go from two fingers, to three and finally four before the hand leaves—and I just fuck him.  Hard and fast—leaving us both breathless.

I change the pace with the speculum.  I want to stretch his hole some more before my hand goes in.

“It’s been forever since you used this on me.”

“Feeling good?”

“Yeah.  Nice and slow…”

And that is just how I am stretching him, turning the winged screw, opening his hole fractions at a time.  Soon the opening is large enough to add my cock.  I fuck him, the metal on either side of my hard flesh.

Once it is cranked shut and gone, I work my left hand into him.  And then the right, but the left feels the best.  I add my cock as well, letting my shaft fuck between my greasy finger deep inside him.  Over and over.

I pull my cock out so once again it can slide down my fore arm and work it’s way in on top of my wrist.  Derrick is lost in sensation.  He groans and only occasionally focuses on the action in his ass in the mirror above the sling.

Now it’s just my dick inside him.  I fuck him hard, but I am nowhere near shooting,

I settle down for a long fist session…

*

Derrick takes a break.  I hop into the sling for him to eat my ass.  He burrows in, rather noisily, as I jerk my cock.  But finally, food sounds more fun.  Derrick’s hole is sated—and food sounds better to me than working forever on an orgasm.

We go out to dine…both feeling that glow of good sex…