Late Night on Lake Shore Drive

Chicago--December, 2011

This picks up instantly after yesterday’s installment about the piss party. After that rather dry event, I’d been invited to spend the night with a couple on Lake Shore Drive. I had known the sub boy for a couple of years. He was one of those boys to who I could do absolutely anything :

Whore him out at a bathhouse for my felching pleasure.

Have him naked, ready and panting, to relax me after a long drive to the city.

Make him suck me off in a crowded bar.

Or give me his ass in the back corridor of that same bar.

Or his favorite--having him lick cum off the floor of the bathhouse when he’d dripped some.

But lately one of his string of tops had become a boyfriend. Marvin, the top, is ten years younger than I, with a shaved head and pronounced features. The boy is good looking enough, dark hair and mid 40’s. I’d played with them together once. It had been fine--though it had ended with them arguing. But not wanting to drive home, I had taken them up on the offer to play a little and spend the night....


 He opens the door naked, save for his collar and boots. I’m shown in. Marvin is sitting in the living room with a vodka and something. “Make him comfortable,” he says to the boy. My jacket disappears, as does my sweater. Suddenly the boy is crawling around my chair. He begins to inhale the soles of my boots, then proceeds to lick the tops. His tongue presses hard enough I can feel it through the thick leather. Slowly he undoes them and lovingly does my feet. He’s impatient though, and the socks come off very fast. He sucks my toes, but soon we are all in the bedroom.

I eat his hole, kneeling on the floor by the bed. The boy is on all fours so he can suck Marvin’s cock. I eat, and rise and fuck. It pushes the boy forward onto Marvin’s cock. His average sized dick never quite gets hard. He leaves us soon to go find another bottom on line. I fuck. I eat. I fuck. I make the boy clean my cock. Soon we hear the front door open and a chattering blond walks in. He’s our age, in decent shape and will not shut up. Marvin tries to silence him by sticking his cock in the guy’s mouth. I stand next to Marvin and let the boy suck mine. That works for while, but soon the blond is trying to stuff Marvin’s softening cock in his ass. When that doesn’t work, the blond takes Marvin to the far side of the bed to orally work him over to hardness. But sucking Marvin’s cock does not shut him up. Marvin just has more vodka.

I dig in my bag and pull out a speculum. I warm it in my hands, grease it, then slowly insert it in the boy’s ass. He’s on all fours and is thrilled as he feels the metal glide into his hole. I give the key a slight turn. Inside him it opens. I crank again. Another crank. And another. Soon his hole is being stretched, side to side. My finger goes in and strokes his prostate. This sends him into a whimpering ball. It piques the blond’s interest. He comes around the bed, looks, shudders theatrically and beats a hasty retreat back to Marvin. I give it one more crank, finger his prostate and lean over to spit into his hole. Slowly I crank it closed, careful to not pinch any of the delicate pink flesh.

I’m back in my bag. I slip on two black latex gloves. I dip into the Elbow Grease and smear it on both hands. The boy looks over his shoulder.

“I want it all this time, Sir.”

I have two fingers in him easily, with the stretching I’d given him with the speculum. I add another. Then three fingers of the other hand alternate in a circular motion to continue opening him. Before I know it, I have four fingers. A little pressure and my right hand is fully up him. This sends the blond for his clothes, saying he’s come to the wrong party. Marvin lets him out the door as I begin alternating full fists up the boy.

Marvin returns with a fresh drink, watches us, then disappears.

I pull out, stroke myself to hardness and fuck the freshly fisted hole.

“Please, Sir, give me your cum.”

I am so close. I want to shoot. I really need to get off. Suddenly, I’m there. I explode. I collapse on his back.
　
*******************

We get ready for bed.

Marvin comes in and says he’s going out.

The argument starts. I screw my earplugs in as tightly as I can and strap my blindfold over my eyes. Amazingly they cut out almost all the noise. I sleep. Aware of movement around me. Mostly the boy on the bed.

Early in the morning I wake up. I remove the plugs and the blindfold. The boy is talking in his sleep. I touch him with a careful caress. He stirs. Then fully wakes. He looks around blinking.

“He’s gone, Sir. Forever.”

“It was a fight. He’ll be back.”

“No, Sir. He’s gone for good.”

“You think so?”

The boy looks at me. There is a hint of moisture around the eyes. “Yes, Sir. I know he‘s gone. I hit him.”