The Bootblack Boy (Mistress Elise Winter & morgan #1)

Elise is so over these regular play parties. She sits in the corner drinking sparkling water through a straw—no need to muss her lipstick over a drink—and surveys the dungeon. There are a handfull of young kinklings, giddy and drunk on flesh and feasts and possibility; a smattering of couples who haven’t left each others sides, their slightly widened eyes giving away their nervousness under their I’m-cool-I-got-this external demeanor; and a handful of former (and perhaps future) of her own play partners. She starts to regret that she ever let Hannah talk her in to coming. Hannah is right—of course, she always is—that it’s been too long since Elise played, but Elise just isn’t sure if what she wants is out there—or maybe more accurately, how to find it. She is starting to feel old at 35, as if everyone has found someone by now, so nobody’s left to find. Except, of course, her.

Tucked into the corner Hannah is up on the high bootblack chair, wearing her favorite blood red Agent Provocateur matching lingerie set and her stiletto thigh-high leather boots. A bootblack is buzzing around her feet, soaping the leathers, expertly massaging Shay’s feet and calves while cleaning the leather. Elise heads over to tell Hannah goodbye and hit the road. It isn’t even midnight yet, but she’s done.

“Hannah,” she starts, a few strides away, “I—”

The bootblack and Hannah both flick their attention over to Elise. The bootblack pauses, just for a moment, blinking, as if he is caught off guard, then quickly re-focuses on Hannah’s boots.

Elise tries again. “Hannah, I’m going home.”

“What? No, you can’t go yet! They haven’t even done the demo,” Hannah protests. That means, it isn’t even midnight. “Stay until then, at least. Barely anyone is here yet. You never know … ” Hannah flashes that seductive smile full of unspoken promises, and Elise gives in immediately, rationalizing it in her head. Well, someone new could show up. The demo could be really hot.

“Hannah, may I lick your boots, please?” The bootblack boy pauses his work again and waits, without expectation, for Hannah s permission. The boots are sparkling clean, oil and some high-quality polish lined up and waiting obediently on the tray for the next step. The boy stands still, focusing, not nervously fumbling but calm and collected. Even at the feet of one of the most powerful dommes in the room.

“You may,” Hannah answers. Though her tone was clear, Elise could hear underneath it that Hannah was a little bored, too. There really isn’t much notable going on tonight.

Elise’s attention drifts to the bootblack, watching as he takes his time getting into just the right position before he gently places his tongue on her finest leather. His tongue is long, thick. Like it barely fits in his closed mouth. He licks in smooth, elegant strokes, almost deicate, though the boy himself is not. He looks like he could be thrown into walls, wrestled to the ground, torn open until he bled, and he’d only say thank you and beg for more.

He licks one boot: the seam of the leather on her insole, and the line starting at her pinky toe; the textured design of abstract flowers that snakes up her calf; and even the seam at the top of the boot, past her knee, well on to her thigh. Hannah sighs, and Elise can see her hips relax and her legs fall open just a little more.

The boy kisses back down her knee and calf, and begins to lick the other boot.

Elise realizes she is staring. Almost drooling. Fuck, why hadn’t she worn her best boots? Hannah didn’t come with him, she picked him up here, so he’s probably unattached and doing anyone’s leather. How hadn’t she noticed him before? Damn he’s cute: quite a few inches shorter than Elise, probably almost the same height if she took off her towering 4″ heels. Light brown hair, light skin, fine fingers and small hands. He had a thin wisp of facial hair, the kind on teenage boys before they can grow the real thing. Elise hopes he isn’t as young as he looks.

“A little longer,” Elise tells Shay. “I’ll stay for the demo.” She heads back over to the perch on the other side of the room and tries not to keep watching Shay and the bootblack, but mostly fails. He is deft, supple, and Elise craves to be in that chair. Her hands start pulsing in her lap, twitching with ache and desire.

The demo starts at twenty after midnight, because kinksters are never on time. Elise loses sight of the boy by then. Probably off playing with somebody else, probably he’s the one making the grunting yelps from the back room, probably he’s already left the party and Elise won’t see him again. A butch daddy-type and thick-thighed curvy gorgeous femme demonstrate a rough blow job for the whooping crowd, the butch standing up high on the bench, the femme kneeling on it, her lipstick wrecked and drool down the front of her bright thrift-store vintage dress. Elise watches half-heartedly, giving up on the party for the second time. That’s what everybody really wants, right? Some sweet, submissive femme—not the towering domme Elise presented. No wonder she had no dates. Play was easy enough—usually—but that wasn’t really what Elise was looking for. She wanted romance, courtship, love, a partner. A wedding, even. And also a servant, a submissive, a boy who would do his proper worship, and obey all her orders to the best of his ability. Even more so than play, she wanted companionship, wanted someone to walk through life with. She’d played with poly and open relationships, and that’s a possibility, but it isn’t necessarily her preference. She is too possessive for that, she wants to go too deep and too all-out with ownership and vulnerability.

It is a hard thing to date when one’s needs are so specific, especially in a community that usually values different sorts of pairings.

Elise turns to make her way through the crowd and head to the coat check.

“Hey, you’re not leaving, are you?” A voice cuts through the noisy dungeon from someone close to her ear. It’s not Hannah s voice, who else—? She turns, coming face to face with the bootblack boy, the crowd so thick that they are almost touching.

“Yes, I think it’s about time,” she replies, smiling. Unless …

“I’m Morgan,” he offers his hand to shake. She takes it, palm to palm, his hand warm and smaller than hers, nesting nicely into her grip. She doesn’t let go.

“Elise,” she says.

He nods, not meeting her eyes, shyly looking down. “I saw you watching me.” Elise flushes a little—was she so obvious? She usually keeps her hand much closer to her chest. But there is something about this kid, something intriguing and so very hot.

“I was,” she says. “You made quite an impression. I liked how you treated Hannah’s boots.”

He nods slowly. “I liked it too. I love to be useful.” He shifts a little, foot to foot. Someone knocks into Elise from the back and she almost falls into Morgan, but catches herself.

“Well, I don’t want to keep you. I just wanted to make sure to introduce myself. I hope I run into you again,” Morgan says.

“I’m not sure I believe in fate,” she says, taking one of her trick cards out of her tiny pocketbook.

“Oh, I do,” says Morgan. “Absolutely.” He smiles and almost looks directly at her, for just a blink,, and Elise sees his eyes sparkle.

“You do, huh,” Elise flicks her arm back and holds the card close, tapping it against her cheek, considering some options. “Then I guess your fate is to call me tomorrow.” She hands him the card, keeping ahold of it, their fingers almost touching. “Not too early, I sleep in on Saturdays,” she adds, setting up a challenge: What would “too early” be to her? 9am? 11am? She lets go of the card.

He swallows, pulling it up to his face to read it in the dim dungeon. Mistress Elise Winter, it reads, with her email address and phone number in embossed blue text on a cream background.

“Yes, uh, Elise. I will. Thank you.”

She leans in close to his ear. “Ma’am will do just fine, Morgan. Thank you for introducing yourself. Goodnight.” Husky, low, sweet. She felt his knees tremble, saw the rumble through his body.

“You’re welcome. Goodnight, Ma’am,” he whispers back.

She kisses his cheek, and disappears into the crowd.

DJ’s Birthday Gangbang (Kai & DJ #4)

I have always wanted to throw someone a gangbang. And by someone, I mean DJ. Maybe because they’ve thrown a few for me—it’s amazing how easy it became to orchestrate one after we’d been traveling to go to kink conferences for a few years—or maybe because I’ve never seen a gang bang where the person at the center is also the top. I’m not quite sure I can wrap my head around it, even though DJ and I have talked about it a bunch.

This year, for their birthday, I decided: fuck it. Let’s just try. Worst case scenario, all the hotties we know come and it’s an awkward good time.

I’ve invited a dozen people to meet us at the dungeon at IMsL at 8pm on Friday, and DJ thinks they and I are having a scene. I asked them to strap, and I’m bringing their favorite toys to use to fuck me up.

They’ll fuck me last. I mean, they’ll do whatever they want, but I hope to be last, even better if they let me get them off after they’ve gotten their fill of everyone else. I’m packing, for sure, and wearing a crisp white tee shirt I starched just for this. On top of that, my leather shorts, suspenders, and my tall boots. I mean it is a leather event, after all.

International Ms. Leather, IMsL, is one of my—our—favorites. It happens annually in the San Francisco Bay Area. The focus is on leather women, but all kinds of genders attend, and the vast majority is queer. There are dozens of classes with amazing presenters in the day, and evening entertainment while some folks compete for the titles of International Ms. Leather and International Ms. Bootblack. We’ve been attending for the past five years, ever since 2009 when everything blew up and we almost broke up, but it ended up being a huge transformation instead. We’d always been open and slutty, but it took a reconfiguring of our relationship to put kink play in the center of our sex lives. We’ve been going to all kinds of workshops, demos, parties, and munches since then. We really reprioritized what DJ calls ‘preserving the boners,’ and have revalued sex in our partnership (and outside of it). I mean, we didn’t want to break up—but we weren’t having sex, like at all, so something had to shift. I’ve been in relationships like that before, where sex peters out and wanes, and I’d never been able to get it back—but hey, we did! It is possible, I always believed in it, I’d just never actually seen it happen before. It sounds cheesy, but I think we really loved each other enough that we wanted to stay together, so we both made commitments to change and keep growing. Plus, therapy. That was essential.

And events like these weekends are so rejuvenating for us now. It’s like we can shut out the world, dive into the power and strength of our sexual connection, and let the rest of our lives go for the whole long weekend. So blissful. It helps that we know everyone here after going for so long—but I still love meeting the new folks. You could say I have a fetish for showing the newbies the ropes. I figure it’s part of my community service.

I show up in the dungeon at 7:30 to get the perfect spot—the corner where a sling, cross, and a massage table are all nearby. Nobody else is there for the gangbang yet, but they will be soon. I told them to be a little early. My pulse is racing already and I’m nervous but excited to get this going. How will it work? What will we do? Do I really have to sit here and wait, with nothing to do, for twenty minutes?

Thankfully, Tanner walks in carrying a big HAPPY BIRTHDAY sign and starts looking around for me. “Over here,” I projct my voice to reach them. They nod and head toward me.

“Setting up?” Tanner asks, giving me a hug.

“Yeah, not much to do though really. I mean all the equipment is already here, so. I like this corner. Lots of options.”

We hear a smack and someone yelps from the next room over, the thin hotel walls barely concealing it. But mostly the dungeon spaces are empty. Everyone is probably still in the hospitality suite having drinks.

Tanner agrees with me about the corner, and we tart talking about the details—who is coming, how will it work? I’m getting excited. It’s going to be great. Where is everyone? Where is DJ? They had a playdate a few hours ago and were going to shower and nap before joining us at 8, but it must be almost time.

A few more folks arrive—Tanner’s friend Rachel; one of my occasional playdates, Lee; DJ’s regular fuckbuddy (and sometimes boy) Ayden. We all discuss what we’re going to do, and how our IMsL has been so far. Lee has already been in two other gangbangs today.

“It’s important to have that friend you can rely on to show up for your gangbang,” I grin at Lee.

“It is my pleasure, buddy, all mine,” they respond generously, clapping me on the shoulder.

Ayden and Tanner are doing that flirting dance, nervously watching each other and talking low. Rachel is pretty quiet, as usual, she’s just watching us all and playing with what’s left of her hair. I’ve never seen it this short—she must’ve cut it for IMsL. Practically a boy cut from the back, but the front comes down to her chin and frames her face. It’s very cute. Something about it makes me want to kiss her.

A few other folks arrive, and Tanner and Lee make the rounds in the dungeon to see if there are any stragglers who would want to come join our scene. They come back with a few wide-eyed new kinklings in tow, talking about negotiation skills and what we’re planning in our scene. Mostly, this gangbang will mean that DJ will have an audience for whatever play they want to do, and each of us gets to have a turn with them. I decided to set a timer: 3 minutes each. That’s not a lot of time, but I also kind of expect people to start lining up if they hear that DJ is down here flogging anyone who wants it. We’re all milling about a little, and Ayden and Tanner start making out, Tanner sitting up on the massage table and Ayden between their legs.

And then DJ comes in.

“What! Is this!” They shout, grinning ear to ear, arms held out wide as now more than a dozen queers rush over to them, grinning, offering hugs and kisses.

“Happy birthday!” We all yell. I’m still in the corner, holding a flogger in one hand and my phone in the other. DJ makes their way to me, scooping me into their arms and holding me hard for a deep kiss. I laugh and moan, melting in their arms.

“Happy birthday, Sir,” I say, quiet. “Welcome to your birthday gangbang.”

“What! Oh man, this is the best. Thank you, Kai, and thank YOU …” they raise their eyes to the group, gathered around tightly, eager to get going.

I put on my game face. “Here’s how it works: You get three minutes each, and thirty seconds to negotiate what you’re going to do. I mean, more if you need it, but most of these folks you know.”

DJ nods, eyes shining.

“Tanner is going first. From there, we’ll just keep offering ourselves to you, until you’re done. Good?”

DJ nods vigorously, eager. “Great.”

“And … can I be last?” I ask, a little quieter.

“Absolutely.”

I think their face is going to break from smiling so hard. “Ready Tanner?”

Tanner hops down from the massage table and comes over to DJ, kneeling in front of them. “Ready, Kai. Ready, sir.”

I start my timer. “Go ahead, then!”

DJ leans down and they whisper with Tanner for a moment, then Tanner gets up and pulls their leather chest harness off, and then their tank top, so they are naked from the waist up. They cover the few steps over to the St. Andrew’s cross and DJ follows. DJ selects a flogger from the variety of toys I’d laid out and starts swinging. They’ve been playing together for months now, and DJ so skillfully knows how to warm them up and take them up to the edge, but not push them too far. It’s lovely to watch. Tanner starts breathing hard, I can see their chest heaving, sometimes twisting away from the flogger and crying out when it’s a particularly rough blow. Three minutes isn’t very long, though, and Tanner’s back is just starting to pinken when my timer chimes go off.

“Time!” I declare. “Next?” Rachel is right there next to me, so I snag her by the arm. “You ready?”

Her eyes are playful, sparkling. “Fuck yeah.” DJ directs Tanner back toward me and I catch them, stroke their skin while they purr and hum, eyes open, still anticipating what’s next. Rachel goes right over to DJ and asks, “Can I suck your cock? Please?”

“I would be honored,” DJ says, and unbuckles their belt. When DJ gets it into their hands and adds a condom, Rachel works her mouth on it, kissing and sucking, using her tongue expertly, her inner lips, her fingertips. She makes little noises around it, closes her eyes, swallowing like it’s gourmet dessert. DJ is rapt. We all are.

I almost forget about the timer, so I start it for two minutes and that goes by so quickly. “Lee, want to go next?” I stage-whisper. Lee nods. “Know what you’re going to do?” Lee shakes their head.

“Time,” I call over. Rachel grins and laughs a little, sucking the spit back into her mouth and giving a couple more tugs and kisses on DJ’s dick.

DJ groans. “Fuck, thank you.”

“Lee?”

Lee shyly walks over to DJ as they help Rachel up, and Rachel joins Tanner in the post-sexy blissed out pile. “What do you want to do, DJ? Anything in particular?”

“I want to fuck you.”

“Great. Yes please.”

They navigate expertly, getting Lee up on the massage table while Ayden and I grab lube and gloves. DJ has flavored condoms in their pocket and slide a new one over their dick. Ayden pulls up their Utilikilt to reveal nothing underneath—”The way god intended!” they declare—and they start in as soon as I start the clock. They’re comfortable enough together that they just go, without much warm-up: DJ slides in slow and starts to pound. Ayden holds their legs up by the knees.

“More lube!” Someone cheers.

“Yeah, get them!” We’re all crowded around, I can’t quite tell who is talking. Voices overlap as they start cheering DJ on.

By the time it’s my turn, half of the folks have wandered away or started their own scenes nearby, but we still have a few folks still watching.

“Do I need to set a timer?” I ask.

“Not for you, baby,” DJ answers. They’ve lost their shirt by now, skin slick with sweat. I lick some of it and it tastes so good, like DJ but saltier.

“What do you want? What can I do for you?”

They think a moment and then grab my hands. “Fist me,” they say. “Did you bring the Hitachi?”

“Yes.” I go for the toy bag and find the nearest plug. It is close enough so they can be on the massage table and it still reaches.

It takes us no time to set up. DJ is swift and determined, and I am so fucking hard after watching all of that. It’s only been an hour or so, but it was a lot of people, practically every instrument of torture and pleasure that I brought, and a lot of people to wrangle. DJ takes off their boots so they can remove their pants, and leaves their dick on. Their harness is easy enough to get under, and this way they can jerk it while I am inside of them.

They’re so wet. Open. Ready to be filled already. DJ leaves their hand lazily on their dick and works the Hitachi at the base, figuring out how best to feel the intense vibration through the harness, or whether it’ll fit under. They find a good spot and settle, sighing, back into the table. It still takes me a while to work four fingers into them, but once I do, and I add even more lube, the thumb tucks easily and I start to push. They open against me, pressing back, and I slide in. A perfect fit.

They start working their dick faster, and pressing the Hitachi harder, and bucking their hips against my hand, and by the time all of that is in place they don’t last long at all, and they come in a deep grunt and a tense spasm that crunches my hand and starts to push it out, leaving only a few fingers still trailing inside. DJ is panting on the table. They pull me up on top of them, between their legs, my weight on their whole body, and they kiss me soft and sweet. Rachel brings over their water bottle, refilled again. Ayden and Tanner are doing some wrestling scene nearby, laughing and grunting at each other.

“So good, Kai,” DJ is still smiling, blissed out and high.

“I’m so glad,” I say back, hugging them hard. “I want your birthdays to be special.”

“Is there anyone left at IMsL that you haven’t fucked?” Rachel asks, holding the water bottle so DJ can sit up a bit more.

They laugh. “I think there are a few more, yeah. Hey, it’s only Friday, after all!”

I laugh, taking a swig of water. I can feel it go down my throat, cold and sweet.

Featured image from Crash Pad Series Episode #98, Micah Riot and Papi Coxxx.