Page 180 of Naughty November
“Do you want to see inside?” A large, older man asks. He’s wearing a fluorescent orange armband which identifies him as a Dungeon Monitor.
“Yes.” I point to my info, though it only lists me asB. “I’m up first.”
“Perfect.” He smiles and reaches out to unhook the barrier so I can step in. “Let’s get you set up so you can stay anonymous. Are you two coming as well?”
“Depends on what he wants.” Charlie doesn’t follow and looks at me. “Need me to stick around?”
Considering my options, I look at the hole and think out loud, “Maybe you could stand outside of the hole for a minute so I can see what it will be like?”
Charlie nods and comes into the play space, waiting in front of the wall with her pet while I’m led around to the narrow entrance in the back. There is a short spanking bench in the triangular room, which will make bending over easier. I set my bag with water and lube down in the front corner next to the cleaning materials the man points out before he leaves. The bench is not heavy, and I push it back to kneel, front and center on the padded floor, with my face near the opening. The top of the hole stops around my nose, but leaning forward puts me at just the right height.
Charlie has her dildo out and she sticks it into the hole, allowing me to take the tip in my mouth. My vibrator chooses that moment to send a series of strong pulses straight to my prostate, and I moan on the silicone material, letting myself sink onto it as the wave of pleasure rushes through me.
“I think he likes it,” Charlie chuckles, though I can barely hear her over the music and muffled sounds of talking and impact play. She pulls her pink strap-on out of my mouth and I can make out her shadow in the dim club lighting as Charlie leans over to make sure I hear her as the vibrations die down and allow me to think straight. “Do you need anything or for me to stick around inside with you?”
“No, I’m good.” I shake my head, though she probably can’t see me. “I’ll get the DM if I need something. Thank you,” I add.
Charlie reaches in to pat me on the cheek and I see her legs walking away, followed by the wagging tail under her pet’s skirt. That’s hot too, and now I have another new kink to try…
Moving the bench back, I lower it so that when I crawl up and scoot down, my ass is in place in the middle of the hole. I know it will be some time, so I pull myself forward and regret it when a pinch to my cockhead has me wincing.
The thought of presenting my hole to passersby while the vibrator teases me has my cock straining against the confines again. Not orgasmingfor a week, with daily edging, has me used to the pain. It’s still uncomfortable for my caged cock and sensitive balls to rub against the bench.
Settling further back, I know I’m on display. I’m an exhibitionist, and the extra layer of only my most vulnerable bits being visible has a hot sense of humiliation to the position. Reaching back, I tap the button on my vibrator until it is at a continuous, low hum.
All I can do is try not to hump the edge of the bench while I wait.
FIVE
DADDY SHELDON
“Work went late,” I explain to Q over the thumping bass in the hall where I’m switching from street clothes to my leathers. “Sorry I couldn’t help set up like I planned.”
“Busy doing data scientist things, I understand,” Q claps me on the shoulder and smirks. Only ten years older than my forty-one years, he isn’t tech savvy, so I know he has no clue what I do beyond my job title. “We only opened the doors about twenty or thirty minutes ago. You’re in time to enjoy yourself, and that’s what matters.”
“Thanks.”
Tucking my bag into a cubby, I follow Q into the darker dungeon space. The lower area has big play setups, while the raised stage has the crosses, rope, and impact play. Before I can ask where to find a certain spot, Q gets drawn into answering some questions about whips and canes up on the LED-lit platform.
Telling myself that I’m simply observing what all the Naughty November stations are, I make my way through the crowd until I find the Glory Holes. There’s a man thrusting into a large black box, and a femme person doing the same against a wooden wall that doesn’treach the ceiling. I can see the bottom is secured to hooks in the floor, but the wall does have some wobble at the top when she pushes against it. After watching for a minute, it’s clear the wall isn’t going anywhere.
“Need your boots blacked, Sir?”
Turning, I find a bootblack sitting on a stool in front of a black bench against the outer wall where the Kink Pride flag hangs. They’re wearing a leather vest with an International Mr. Bootblack patch alongside others including a they/them pronouns button, plus shorts and boots in good condition. I remember meeting them before in the community, but can’t recall a name confidently enough to use it. There is a young man standing behind them with his arms behind his back and all the materials laid out to do the blacking between them.
“Rain.” They speak again to remind me of their name when I don’t reply right away. “I’m teaching my friend here and need volunteers.”
The bench faces the glory hole setup, and I could use a shine. Plus, anyone who won IMBB knows their shit. “Sure. I volunteer as tribute.”
Taking a seat, I let Rain and the novice boot blacker know what I used last time and how long it’s been. Rain explains the product they are using, “Huberds is great for a more mouth-based boot-worship. It’s edible, tasty, and makes for good lube, too. For this one, though, we won’t be getting so up close and personal.”
Chuckling, I agree with their plan, then tune out their conversation while I watch the femme person at the glory hole step back. The lighting is low, but one purple-colored overhead light shines right on the hole. I can make out full lips, drool dripping from a thoroughly fucked mouth. I can’t tell who it is, but I think a man is in there now.
After contacting Charlie the week before, I found out the boy she had with her wasn’t her partner. Beckett is curious about being fucked by a cock attached to a cis-man, with the possibility of being cum-filled. Charlie wouldn't tell me anything else, because she thought it would be more fun if I didn’t know if it was Beckett or someone else. She also teased me about asking, but I didn’t mind.
Relaxing into the feeling of them cleaning off my boots before moving on to the conditioner, I could just make out the sign from my place about twenty feet away. I read over it along with the list below. Ihad filled out a form and saw I was third on the list to take my turn. I had to hope Beckett was there when I got to try it out.
‘B, 29, cis-male’sounded like him.