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…

Derrick Behind the Camera

Well, the post got started...

But not finished...

I am writing about a session with Derrick...so here's a picture he took of me...

The Bear In the Middle

 Near Home—January, 2023

Another day (mid-month).  Another day at the bookstore.

 

It is just after lunchtime as I park.  There are more cars than usual filling the lot.  A good sign?  Who knows?  I go in, exchange pleasantries with the clerk, go off to piss and finally walk into the straight theatre.  A few men are scattered around the room.  All attention is on the video, not each other.  I sit to the side and unbutton. 

The porn is good.  DP anal here on the straight side.  I stroke. 

The men are restless.  The five men in the room are soon replaced with others. 

I stroke.  I think I hear a blow job happening behind me.  I hear steps behind me.  I turn.  An older Black man is there, his cock filling his fist.  He is likely in his 50’s.  You can tell he once was heavy, but he’s lost a lot of weight, with layers of belly skin that has not yet re-sized.  But his cock is a beauty.  It is darker than his over all skin tone.  He’s as long and as thick as I am.  The flared cock head juts up, at a different angle from the thick column of flesh behind it.

“They said you suck cock,” he whispers, jerking his head towards the man in the cocksucker’s seat (who is busy on someone else.)  I don’t answer, I just take his dick into my mouth.  Fuck, I’m full.  I fear my teeth are in the way, as I can’t possibly cover them correctly with the stretch to take him. 

The man sighs.  Then tells me in another whisper that he loves my tongue action.  I’m glad for the feedback as I am feeling I can’t do any of my usual tricks with the amount of cock flesh in my mouth.  I pause for a second with just his drooling cock head on my tongue.  He decides to fuck my face.  I just stay still and let him pummel my mouth and throat until my eyes begin to water.

I pull off him and use all the spit he’s created on his hairy balls.  They are big and covered in kinky black hair.  He strokes his cock and groans as I lick, leaving them wet and sticky. 

“You swallow?” he whispers.

I nod. He pushes into my mouth.  His cock gets even girthier as he begins to fire.  He’s so deep I can’t taste it at all.  His load goes straight down my throat.  I get the merest hint of his tasty load on my tongue when he pulls out.  He squeezes my shoulder in thanks and disappears…

*

I watch a little porn and stroke. 

I move next door.  A white bear with a shaved head is sitting in the room alone.  His jeans are around his ankles.  He is stroking a thick cock.  I sit along the back wall.  We eye each other as I unbutton and haul out my cock.

“That’s a beauty.  Let me suck it.”

He slumps down in the chair.  I stand and feed him my dick.  He begins doing to me all the things I have just been doing to that huge dick.  Lots of tongue, deep throating and ball licking.  I sigh with pleasure.

The door opens.  Neither of us move.  A young Black man enters.  He stops, transfixed, that live sex is happening right in front of him.  He moves around so he can see better.  We both like an audience.  The Bear strokes himself as he takes me to the root, showing off.

The young man has pulled out a bigger than average cock.  He strokes as he watches me grab the Bear by the ears and fuck his face.

“Hot!” he hisses, his hand moving rapidly over his dick.

“You should try his mouth.”

The young man steps back, then takes a breath and walks towards me.  I pull out of the Bear and let the newcomer get sucked.   I watch the look of appreciation cross the kid’s face as the bear start his tongue work.  I go to my knees and begin sucking the Bear.

Things escalate fast.  The Bear is groaning—with a dick in his mouth and a mouth on his cock.  I can feel his pre-cum become a river.  The young man is now pumping into the Bear’s mouth.  Faster and faster.

“Oh, fuck!”  The kid starts to spurt.  He makes a move to pull out, but the Bear holds him in place.  The Bear groans, taking the load—and suddenly spurting one into my mouth at the same time.  I lick him clean as he does the same to the young man in his mouth.  I stand, stroking.  The young guy looks at my cock.

“Shoot that thing,” he says.

“In my mouth,” the Bear grunts out.  I stroke my cock about five times before I shove it into the Bear’s wet mouth, mixing my jizz  with the remnants of the load already on his tongue…

A Night of Wigs and Walkers

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James Gets Creamed

 My Playroom—January, 2023

I came home delightfully sated from my New Year’s Eve adventure.  I was not on the prowl for more sex anytime soon.  But I was pleased to get a text from James, the younger looking blond from that night.  He wanted more.  He really wanted my load—he was so sorry he had gone home before he got it. 

We chatted on and off for most of the day.  By the first Friday of the new year, he was stripping in my playroom…

 

James tosses his clothes in the chair.  I take off my robe and hang it on the doorknob.  He is naked but for a yellow jock.  In the light of the afternoon (and not a dark backroom) he is likely higher in his 30’s than I thought when I first met him.  Not that it matters. 

He goes right to his knees.  “Come here, Daddy.  Let me suck on that big thing again.”

He mouths the jock pouch for a bit, making my cock swell.  Then it is in his wet mouth with his ever-moving tongue.  He remembers my hotspots—my balls, and under my balls where the cock ring pushes them out.

“I want to lick your ass.  Up on the bench.”

The poppers come out for him the moment my tongue finds his tight pucker.  I can’t wait to make it gape.  I poke and prod and spit.  He has found the mirror on the side wall that lets him see me at work on his ass.  The poppers make his chatter.  He tells me how good my tongue is making his tight hole, how he wants me to destroy it, to fill it with cum…on and on.

I coat my throbbing cock with coconut oil as I tongue him.  I spit a couple of more times into him.  I stand up and my cock finds his now loose ass lips.  I push in.  He groans and takes another hit.  I hold until his hole responds—letting my cock bottom out in his tight tunnel.  I fuck him.  Slowly.  Making him mine for the day. 

“Harder, Daddy.  Make me feel it.”

I let him have it, faster than my usual slow build.  I plow him.  It’s the only word.  He is incredibly vocal, egging me on.  My foot goes up on the bench next to his knee.  It lets me get even deeper in his ass. I pummel him, over and over.

I pull out.  “Taste your ass on my dick,” I say as walk towards the head of the bench.  He hungrily takes me into his mouth.  His tongue swirls.  He gurgles, delighting in the heady blend of coconut oil and ass jizz.  “Get me good and wet—no lube for this next fuck.”  He leaves my cock dripping with spit.  And I plow back into his hungry hole…

*

We’ve moved to the sling.  I insert the small butt plug into him.  I keep his hole open as I make him suck my dick—then I stand on tiptoe and have him lick my balls again.  He loves how sweaty they have become from the exertion. 

The toy come out.  My cock goes in.  I fuck him.  His eyes are riveted to the mirror hanging above him.  He can’t get enough of watching his hole be used.  By cock.  By tongue.  By toy.  I have pulled out the egg-headded dildo.  The big head is a major stretch for him, but he takes it.  There is no way he is ready for me to add my cock along with it.

The toy stays in as he licks my cock once more, craned around, hanging out of the sling.  I move back and fuck him fast and deep.  His ass lips are curling and changing color as the blood rushes to them.  This makes me pull out and lick them, sucking their plumpness into my mouth repeatedly.

“Can I try the speculum on you?”

“Anything you want…”

I grease it up and slide it in.  I crank.  Slowly.  His eyes get wide as he feels his hole open.  I finger his prostate.  Finally, it is open wide enough I can play with his prostate by inserting my cock.  He loves this and tells me so.  Sometimes with words, more often in low moans of delight…

*

I help him out of the sling to stretch his legs.  I lay on the bed.  He crawls between my splayed legs and sucks my glistening cock.  He is in no hurry.  He sucks and licks every inch of it.  A tap on his head sends him down to include my balls, too.  First one, then the other.  He tries for both in his mouth at once, but doesn’t quite succeed. He pushes my legs apart as his tongue moves down to my perineum.  His tongue teases all the hair there, coating it with his spittle.  He flirts for a second with licking my ass, but comes up and kisses me instead. 

We stay entwined for quite some time.

“Sit on my face.”

I continue to lie there as he kneels above me.  He lowers his thoroughly fucked ass to my mouth.  My tongue is in him from the moment he settles there.  Deep and loving how wet he is.  How wet I’ve made him.  I lick and spit and he groans out his appreciation and tells me that his hole is all mine.   

He begins to rock, pushing his pronounced ass lips over my mouth and my nose and back again.  Poppers are opened.  He begins to babble all sorts of filth about my cock, my cum, about breeding.

“I really want your cum in me.”

“Let’s do it.”

We go back to the sling.  I eat his hole some more.  I can’t stop myself.  Finally, I stand up and fuck.  Long strokes.  Deep and hard.

“Fill me up!”

“Fuck…” I mutter.

“Give it to me…”

I fuck harder.  “I am so close...”

“Daddy, cum is the best…”

A couple of more strokes and I am there.  I can’t stop shooting.  It’s a five-day load.  Spurt after spurt.  I fall on his chest.  His arms go around me.  James milks my cock like crazy.  I can feel myself drool out a little more…

*

He didn’t shower.  He wanted to go home smelling as I left him.

I sent him the pictures.  He thanked me and told me he could still feel my load inside him.

I got another text after he napped—for when he awoke, his thigh was wet and creamy…

New Year's Eve Tail (conclusion)

 Lansing—December, 2022

(Part one is here.)

I go find Perry and his friends, my beard still smelling of the cum I have been felching from the young man’s well fucked hole.  Perry is back in his clothes, sitting on a bench, eyeing the gloryhole booths.   The four of us go on a tour of the facility, wondering where to fuck for round two.  We look at the sling near the big screen gay area, but the space is cold, as there is an outside door nearby.  We both agree that the other sling is the place.  It’s empty now.  I move the moveable wall semi shut—so men can still get around it easily, but it still blocks direct traffic.   When I look back, Perry is already naked and being helped into the sling by the Cub.

I go to my knees and eat out Perry’s well fucked ass.  The Cub gets busy on Perry’s nipples.  The young Bear jerks his dick to the scene.  Perry is wet.  Damn wet.  Nor is it from all the cum in my beard from the felching.  His stretched hole is making lube like crazy.  I slurp loudly, spit some back in and stand up to fuck.

Men are standing behind the half wall watching me insert my rock-hard cock.  One of them comes around the corner to get a better look.  The young Bear is soon sucking his dick.  I am plowing noisily into Perry.  He pants and tells me to fuck him harder.  Another guy enters our sling corner and sticks his cock in Perry’s mouth.  Now he can’t talk—but only gurgle his pleasure around the man’s thick dick.

I wait until I hear the new man sigh and ask:  “You want to switch holes?”

The guy considers it, but shakes his head.  “His mouth is great.”

When the other man moves on, the guy getting head from the young Bear comes over to try Perry’s mouth.

As I drop once more to my knees to eat Perry’s fuck hole, an older man appears around the low wall.  He gropes himself through his pants as he watches me rim Perry.  I stand up and fuck.  The new guy goes carefully to his knees to watch my cock split Perry open.  I fuck.  Harder, with someone watching so intently.  Finally, I pull out.

“Let me suck that,” whispers the kneeling observer.

I present my wet meat to him.  He licks me clean.  Hungrily.  Savoring the juices.

“May I rim him?”

“Sure.  Eat his ass.”

He buries his face into the hairy cleft of Perry’s butt cheeks.  The rimmer groans and stops groping himself, so intent is he on licking ass. 

I let him go until he slows a little.  “Let me fuck some more, and then you can do it again.”

“Thank you, sir.”

I fuck.

He eats.

I fuck.

He cleans my cock and eats Perry.

I fuck.

And the young Bear takes a turn cleaning my cock as the man eats out Perry.  My new cocksucker is great.  I can see why he’s had a succession of men in his mouth while I’ve been fucking.

I fuck Perry one more time.  A new man is in Perry’s mouth while I do it.  The rimmer has never left his knees.  He is either groping himself, cleaning my cock or licking Perry’s wet hole.  I idly wish he were nimble enough to get under the sling and lick my balls while I fuck…

Perry finally calls for a time out.  He gets dressed as we talk about a dinner break, but we leave it open.  I go to my car and eat dinner and check my phone.  I drive for a bit and get coffee.  I am back in the play area just before 8pm.  I don’t see Perry and company.

It’s a holiday and a Saturday night.  The establishment is now mostly gay men with a few straight swinging couples.  I watch a woman fist her husband in the sling we had been using.  She invites other men to do him, too.

I go down to the gloryhole area.  A young-looking blond man is sitting on the bench watching some trans porn.  I smile, continue past him and into a dark corner. 

In moments he is there.  “Need some help with this?” he asks, fondling the bulge in my pants.  I nod.  He unbuttons.  He goes for the jock pouch.  He inhales and lets out a sigh.  “Heaven,” he mumbles.

He spends the next 20 minutes licking the pouch, licking my nuts, once they are free and only then on sucking my drooling prick.

He pulls off it.  “Will you fuck me?  I need to feel this beauty in my ass.”

I nod and he strips right there.  He has a thin to muscular frame, not much body hair and an ass I can’t wait to eat.  Built into the walls in our corner, is a waist high platform.  He bends over on it, presenting his rounded cheeks to me.  I pull them apart—and my tongue touches his hole for the first time.  He groans and pushes back, impaling himself on me.  He wants it—and I want more.  I rim and spit, getting him ready for my cock.

“You want me raw?” I ask, standing up. 

“Only way I fuck,” he pants out.

I enter him, slowly, inch by inch.  He has skills.  He milks me expertly as I press forward.  When I bottom out, I hold and begin the fuck.  He groans.  Two other men come watch me take his ass.

“Can we go to the sling?” he asks.

“If it’s free.”

He doesn’t bother to put his clothes back on to get there.  I don’t bother to try to cover my dick.  We just go.  In the light, he’s slightly older than I first thought—maybe a very young looking 40.   He hops in the sling.  I eat his fucked hole before standing up and plowing him again.

We take a break.  He sips some of my water.  Names are exchanged.  He’s James.  Not Jim.  He promises me a phone number if I fuck him once more.

I do.  Thoroughly.  Almost to the point of blowing my load.  But not quite.

He needs to go home to be with his mom before midnight.  We go wash up and we exchange numbers.  But we can’t get enough of each other.  We dawdle and talk.  Then I lie on a bench behind the slurp ramp.  He strips and sits on my face.

“So hot,” he croons.  “Eat me…”

Without my asking he knows to ride my tongue, then my cock and bring his gaping hole back up to my face.  He does this twice.  The last time on my face, he stops jerking his dick—though I would have been fine with his load all over my sweatshirt.

He gets off me.  “Let’s finish this right when I have more time.”  I reluctantly agree.  We kiss, savoring his juices in my mouth.

And he’s gone.

Fuck, I need to breed.  And soon.

A young, cubby guy, with an incredible Grizzly Adams beard finds me.

“You have a great cock.”

“Thanks.”

“I want to be get fucked.  You can load me if you want to.”

We are walking towards the sling behind the low wall.

He continues:  “I just don’t do that very often.”

“Take the load?  You decide,” I tell him as I get his legs up on the chains.

I eat his very hairy hole—even more of a contrast after James’ hairless one.

“Oh, fuck…” Grizzly Adams groans.  “Plow me.”

I do.  Repeatedly. 

His uncut cock grows whenever I eat his hole.  It shrivels as I fuck.  He never touches it.  He is all about his hole.

I eat him one last time.

“I am really close,” I tell him as I begin to fuck.

“I want your load.”  He is panting with excitement now.  “I want…to start the new year…”  He doesn’t finish.

“With my load inside you?” I grate out.

“Yes.  Yes!”

And I’m there.  I shoot and shoot after all the incredible sex that day.  His hole is awash with my cum.  I kneel and clean up what is leaking out.  I stick my softening cock back in him to help push it deeper.  He sighs in perfect bliss…

I go to wash up. 

The clock on my car’s dashboard tells me I did indeed breed him right at midnight…