Terry Is Full of Surprises

 My Playroom—September, 2026

I had given my number to a very talented cocksucker at the bookstore.  We had played a few of times over the years.  He’d hinted that he wanted to try anal with me, but not in public.  Once my dick was back to normal, we set up a time for him to come to the playroom.  I really didn’t know if he was a novice or whether he regularly took dick up his ass…

 

Terry shows up right on time.  He’s tall and rangy.  His snow-white hair is pulled back into a tiny ponytail.  I can only guess that he is my age—or a couple of years older.  I learn that he is married—and his wife knows he plays but hates the idea.  As we walk down the stairs, I ask about condoms and he makes a point to tell me he’s on PrEP as well as fully vaccinated for M Pox. 

His eyes light up as he walks into the playroom.  “Wonderful,” he sighs and begins to strip.  Once naked he sits on the bed.  I pull my cock out of my yellow jock as I stand in front of him.  He leans in and begins to suck.  He’s great.  His tongue is active—and everywhere.  He holds me by the balls, as if he thinks I’ll run away from him. 

He finally pulls off me.  “That’s the cock I remember,” he sighs.  Then he goes for my balls and, eventually, back to deep throating me.  He pulls off me again and sighs once more.  “Get this thing inside of me.”

I have him kneel on the flattened fuck bench.  I eat his hole for a long time.  It opens slightly, allowing me to go deeper yet.  I grease my dick with coconut oil as I eat him out.  He has found the mirror on the side wall and he is eagerly watching me rim him.  I stand up.  My cock pushes against his pucker and I slide in.  I don’t stop until my balls slap his ass.  He sighs as I hold a moment and then begin to fuck.  He feels great.  And in moments, his hole has really opened.  He has the feel of guy who likes big toys and fist.  I keep fucking, but I reach over and grab the Ballistic Butt Bomb.  I pull out as I twirl it in the oil—and then into his ass.  I slide my cock back in along the metal shaft.  I fuck it deeper into his hole.  “I love that,” he groans.  I pull out and work the toy out of him.

Damn.  We take a break while he does another round of cleaning.  I lie on the bed and watch the porn.  He’s back fairly fast and nimbly gets in the sling.  This guy has way more experience than I thought.  I kneel and lick his freshly rinsed hole.  He’s now spotless.

And eager.

He takes my dick.  I can really pound him in the sling.  And I do.  He grunts out his pleasure.  I add the eggheaded dildo.  He likes the feel of it going in—and even more so when I add my cock for a double fuck.  It’s a great stretch.

I go back to the cleaned up Ballistic Butt Bomb and add my cock with that.  I pound the oval head deeper into him—and he stays wonderfully clean and juicy.

For a change of pace, I grab the Spades.  It is almost too small a toy for him now, but he sighs as each mini-butt plug pops in.  He takes three spades the first time.  Four on the second.  All five of them on the third.  He loves the pull out—making his hole expand and contract over each plug.

I get the Seahorse.  He takes all of it the first time, curve going down.  I reverse it and he takes all of it with the curve going up.  He’s a talker as I work his hole.  He tells me he had a recent weekend at a MAFA event, the Chicago fist group.  Part of me wishes I’d known this from the top—but it is actually a fun surprise—and a confirmation of what I was feeling when I fucked.  I keep reversing the Seahorse—and he can’t decide which way the curve feels better.  “Just love those bumps,” Terry murmurs.

To give his hole a break I move to the clear dildo with the black handle.  It’s a steady glide into him.  All the way, of course.  In and all the way out.  And all the way in again.

“I didn’t bring down the heavier duty lube,” I tell him, “As I didn’t know we’d be doing this.”

“You can likely get your fist in me with what you have.”

I am low on coconut oil at this point, but I have three bottles of Fuck Water, a silicone-based lube, from when they were sponsoring Fornication events.  I don’t use a lot of silicone lube, but today it comes in handy.  Literally.  I coat my left hand with it.  Two fingers.  Three. Four and I’m in.  His hole welcomes me easily—with little effort from either of us. 

I hold still.

I turn it slightly.

I pull out.

“YES!” he groans as his ass lips shut almost tight.

 I do it all again.

In and out. 

Terry sigh of relief and pleasure fill the room.

The next time I go into him, I do it standing.  I pull my hand out slightly and my erect cock slides down my wrist and rests on my palm inside his hole.  Terry groans.  He watched it all on the mirror above him.  I begin a slow fuck, my cock going across my palm and through my open fingers inside him.

“So hot…” he mumbles.

I pull out.  Cock first then hand.

“Do that again.  Please!”

I add some Fuck Water and work my hand inside him.  Then the cock.  I fuck him.

“That must make you shoot, doesn’t it?”

“I have never shot this way.  Though I’ve tried.”

He groans.  “I should tell you.  I really want your cum inside me.  I love the stretch.  But I want the load.”

Another surprise.  But a good one.

I go back to the clear dildo to give his hole a rest.

Soon, I re-grease my hand and cock. 

The left goes inside him smoothly.  I add my cock.  He groans.  He plays a little with his limp dick as I fuck once more across my palm and through my fingers.  It always feels good, but right now it feels terrific.  I feel my breath change.

So does Terry.  “Give it to me.”

I pick up the speed of my fuck.  I tighten down my fingers making me rub more on my invading dick.  It works.  I’m panting now.  I’m going to blow my load on my hand deep inside his hole.

“FUCK!”

I’m there.  I stop thrusting and just let my cock spurt and spurt.

Terry moans.

I slowly pull my spent dick out.  “I’m going to push my load deeper,” I tell him.  And my fist pushes my fresh cum into his second hole…

*

We were done as soon as I pulled my fist out.  He loved it.  And I couldn’t believe that I’d finally shot using my hand so deep in his hole.  Almost 50 years of having sex—and I just did something new…