Naughty November

Chapter 5

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’t reach 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. I had 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.

The next line was harder to make out in smaller font: “Tested two weeks ago, on PrEP, no fluid-bond partners. Barriers not required with recent negative tests and on meds. No allergies.”

Then, underneath, “Open to: Receiving anal from fingers, strap-on, or bio-dick; Giving oral; Being cum-filled.”

Fuck. Another one of my kinks I rarely indulged in .

Adjusting myself in my leather zip-up jock, I glance down at the two bootblacks and find Rain smirking at me. “Am I doing a good job, or was another scene piquing your interest?”

“Ah, not that it doesn’t feel great, but…” I trail off and they glance towards where my attention is fixed.

“Signed up for the glory hole?”

“Yeah, for giving.”

“That sounds so hot,” the novice commented, and Rain directed him back to my boots.

They were moving onto the aromatic yellow wax, rubbing it into the leather surface and giving me a sort of foot massage I always enjoy. I focus in on the spot where the hole is now giving me a clear view of the person’s ass and I can see something around his cock and balls. A cage and maybe something to stimulate his prostate?

My cock leaks and I decide to go ahead and point it up toward the top band of my jock at the rate I’m going. Rain doesn’t say anything while I watch the person step back up and sink into the waiting hole, stealing my view. I don’t know if she is the first or the second, but I am ready when it’s my turn.

If I have to end the book blacking lesson early, I’ll make sure to tip well. No way am I missing my chance to step up to the glory hole for myself.