Happy Anniversary, Sir

A submissive man has a special play session with his leatherman buddy.

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I knocked on his door at precisely 2 pm, as he’d asked me to do. He and his husband lived in a classic midcentury home, with tangerine orange entry doors. Palm Springs was full of houses just like that, so I had to check the house number a few times, just to be sure. I knocked twice before I heard the door unlock. 

A text arrived: Make yourself comfortable, see you in the bedroom in your usual spot when you’re done. It was Sir's respectful way of allowing me to undress without an audience. 

I’d craved a hookup buddy for years, but thought that was out of my reach. Sir had photos on his social media profiles of handsome, burly men kneeling before him, looking up at him with wonder and gratitude and lust in their eyes. 

I had the big burly part down, but my body was a bit battered. I couldn’t kneel on my damaged knees. The scar tissue from my accident and surgery reduced my range of motion on one side. My anti-inflammatory medication fucked with my dick’s ability to get hard sometimes. 

I kinda figured I was out of the game, until I met Gregg - Sir - at a bar. 

At Sir’s house, I was ready, stripped to my jock, sitting on the bench at the end of Sir’s bed.  Sir knew I couldn’t kneel in front of him, so I sat on the bench, eyes on the floor, not looking up until I was given permission to do so. 

I heard his footsteps as he confidently strode into the room. Sir had my favorite pair of calf-high black boots on today. I let out a little moan, wishing I could kneel to lick those boots. 

I didn’t know I had a submissive side before meeting Sir. I’d dealt enough with bullies and assholes over the years that the idea of a dom having power over me scared me. Relinquishing control horrified me. 

And then I learned what a “soft dom” was, learned that there were as many ways to be dominant and submissive and sexual as there were ways to be alive. Sir’s probably somewhere between “soft” and “alpha,” and it works for us. 

Sir is wearing my favorite jockstrap, an old red jock. The smell of his crotch, his sweaty uncut dick, wafted up as he rested his hands on my shoulders, his belly and jock pouch nearing my face. I couldn't stop inhaling the amazing scent. 

“Scotty,” he sighed. 

“Thank you, sir.” 

I’m sure Sir and his husband were different in their day to day lives - my brain initially tried to calculate where, why, how. Maybe they went to vintage stores and farmers markets? Made handcrafted soap on the weekends?

I was new to the scene and had my own snarky asshole judgments about it all at first. It all felt like it was play acting, all pretend.

Until a wise friend told me something that changed my perspective completely: in roleplay and fetish play, it’s not a game of pretend. It’s distilling one small part - a very real, authentic part - of that person’s essence into a beautiful, focused experience. 

Sir walked to his dresser, where I’d left a gift I’d brought for him. I doubted he was going to remember, but today is the anniversary of our first meeting. 

I heard Sir make a small surprised noise. He seemed pleased by the present. 

“A fine Maduro. Excellent choice.” 

He pauses.

“We should go out to the patio, so I can enjoy this….and you can, too.” 

I can feel his eyes on me. I still haven’t looked directly at him. 

“Do you need a hand, Scotty?” 

I’m embarrassed, but I nod. His hand helps steady me as I get out of bed, and I look at Gregg - Sir - as we stand face to face. 

Fuck, Gregg’s a beautiful specimen of man. Close cropped hair, peppered with gray spots,, a wild bushy beard, and a handsome face, with piercing brown eyes. Barrel chested, every bit a leatherman. Central casting couldn’t have done any better. 

He might even be a few years younger than me, but he exudes power, masculinity, maturity. 

Sir smiles at me, and it sends a spark of electricity through me. 

I was so surprised the first time he invited me to play, when we discussed our limits, the rules of play. 

The first time I told him about my limitations, and all he said was, “Okay. We can make adjustments.” 

I sat with his response for a long time. Being invited into a room you’ve been denied entry to for a long time is a powerful, if overwhelming, thing to process. 

Sir’s patio is the perfect place for him to relax, sipping a beer made by Austrian monks, puffing away on the Maduro. I breathe in the cloud of cigar smoke, an aphrodisiac for me from day one, and I am instantly rock hard. 

He knows the cigar’s effect on me and he takes his time enjoying it, surrounding me with a cloud of smoke several times. 

After Sir’s had plenty of time to enjoy his cigar and beer, he smirks and tells me I should head to the en suite bathroom. 

I smile as I walk to the shower, there, stripping out of my jockstrap. 

He steps inside and I look up at him. He nods. 

I wrap my mouth around his impossibly thick cock, waiting, waiting, and then it starts, Sir’s thick stream of piss. 

I never thought I would enjoy piss play, or drinking piss, but it’s one of my favorite things to do with Sir. His hands holding onto my head as his heavy stream fills my mouth - or drenches me, soaking me - is always amazing. 

We’ve done it here at his house several times. My fantasy, someday, is for him to take me to the leather bar and feed me right there, or drench me as other men, other leathermen, other daddies watch, stroke, get all excited at a hungry sub like me being marked by his Sir. 

I shake the last few drops from Sir’s cock, and I know what’s next. I love getting fucked when we’re in the shower, standing up, leaning over, taking Sir’s cock. 

Sir squirts a generous dollop of water based lube on his fingers, and starts working a finger into my hole. He whispers in my ear, licking my neck as his finger explores my hole. 

“You’re gonna be a good boy and take this cock, Scott.” 

“Yes, sir.”

A second finger opens me more, than a third, and I endure Sir’s teasing fingers until I can’t wait any more.

“Please fuck me, sir. Breed me.” 

“Fuck yeah, Scotty. I love breeding your ass. Your hungry, willing ass, all open and slicked up for me.” 

It sounds dumb and sappy to say it, but Sir and I kinda do become one organism when he’s fucking me. We move together so perfectly, his cock and balls bouncing against my beefy ass, me backing up with every thrust so he can go deeper and deeper. 

I don’t just want Sir’s cum in me, I need it. I need to know his load is inside of me. 

Need it. 

I start saying it aloud, begging for it. “Need your cum, sir, need it inside of me.” 

After an easy, slow ride on my ass, Sir picks up the pace, mutters some horny nonsense, calls out my name, and then his fat tight dick spurts in my ass. I feel every bit of it. 

“Can I cum, sir?” 

“Cum for me,” Sir growls, and it sends me over the edge, making me cum all over the bench in Sir’s shower. 

Sir’s arms wrap tightly around me. The feeling of his soft cock inside me is so tender. He rubs my shoulders as he pulls out of me. 

He steps out of the shower and I know what he’s coming back with - a small buttplug. I can’t stop smiling. 

Sir gently pushes the plug inside me. It’s not very big, but it will do its job nicely - keeping Sir’s load inside of me for as long as I want. 

He turns the warm water back on, soaping me up elsewhere, planting kisses on my meaty chest, neck and shoulders. 

After we’re dressed, Sir has a big smile on his face as we say goodbye. 

“Happy anniversary, Scotty,” he says as he hands me a present. “Open it when you’re home.” 

I’m speechless. He did remember, after all. 

“Thank you, sir.” 

He embraces me tightly.

“Thank you, Gregg," I say, my voice breaking a little. "For everything.” 

I’m lucky to have a play buddy I can trust. It just makes me want to explore deeper with him. 

“We’re gone for a few weeks, Scott. But I’d really like to see you when we return. I’m looking forward to it.” 

At home, I open the present. It’s a guide to shibari, a Japanese rope tying art. I smile as it hits me: Sir wants to tie me up. 

The idea of Sir manhandling me while I’m tied up, the feel of his load (and that buttplug) in my hole, the scent of his dick on my face, the taste of his piss is all too much and I yank down my shorts, hard, grabbing my dick, fisting it furiously, yelling out “Sir!” as I cum a second time. 

I fall asleep that night thinking of Sir’s hands on me, the scent of his cigar and the feeling of his load inside me.


NOTE: This is my first foray into writing about some of the fetishes and roleplays listed here. I hope I've done them justice, but if I haven't, please feel free to share some constructive criticism with me! 

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