Chapter Six
I ’ve been holding off on texting Leo.
A part of me hesitates, not wanting to fall into the same predictable patterns: endless conversations that lead to an awkward first date and then fizzle into nothing. From experience, that’s exactly how it goes...
A connection on a dating app.
Bland, repetitive conversations.
An awkward first dinner date.
Flirtation that quickly turns physical.
Hot lip action which becomes a sweaty naked dance.
Followed by uncomfortable post-sex small talk.
No second date or ghosting.
It’s a frustrating cycle, one I’ve been stuck in for too long.
“That’s gay dating,” Trey always says, “why do you expect anything different?”
For a while, I believed him. I even considered giving up on the idea of meaningful connections altogether, thinking maybe casual flings were the only way forward. One particularly lonely night, I nearly convinced myself to start. That self-talk was the toughest, most brutally honest conversation I’ve ever had. Some I wished I’d recorded it; it might’ve helped someone else
With Leo, it’s day and night difference.
We didn’t meet on a dating app. We haven’t had conversations in text form and none of it was forced. And while, yes, we kissed—and he gave me the best fucking blowjob of my life—there’s something more there.
Just thinking about it again is getting me hard.
Let’s not forget the avalanche of flirtation between us.
He has shaken up my world.
Now I’m at work, completely unproductive, staring at a picture he sent me the other night and wondering whether I should text him.
Throwing myself back into my office chair, I let out a deep groan. Why does liking someone have to be so damn complicated?
Then there’s the playroom.
A part of me wants to call it off before it even begins. Maybe I’m not the right guy for Leo. Learning about dom/sub dynamics has been intriguing, but what if I’m just not cut out for that world? I don’t want to waste his time or mine.
“Are you okay?”
I swivel toward Emily, who’s standing in my office doorway, her expression curious and concerned.
“Could you close the door behind you, please?” I told her before she sat down across from me.
“I’ve never seen you like this,” Emily remarks, quickly closing the door.
“That’s because I normally don’t have guy problems,” I reply, trying to keep my tone light.
Her eyes light up with intrigue, “A guy?! Who is he? Tell me everything!”
Here’s the tricky part. I can’t share too much without breaking my promise to Leo. Emily knows her way around the BDSM community—she’s even mentioned Wonderland before—which makes this even more complicated.
“Yes, a guy,” I say, carefully crafting a half-truth, “we met a few weeks ago during...a client lunch. He was sitting at the next table. Long story short, we bumped into each other, started talking, and hit it off. We met again at a bar with live music. One thing led to another—making out, best blowie of my life. It’s been a few days since then. I haven’t texted him back and were supposed to have dinner tomorrow. I’m not sure if I want to pursue it.”
“Wow, anything you might want to add?” Emily sassily said, “and why not, This guy sounds amazing.”
“He is. I’m not sure we’re on the same page when it comes to certain...interests.”
“What kind of interests?” she presses.
Why can’t Emily just let it go? I can’t tell her about Master Leo or his playroom. Even though I trust her, this isn’t my secret to share. I won’t betray that, not even for someone as perceptive and trustworthy as Emily. I trust her, it's a boundary I need to respect.
“Let’s just say this guy has...alternative tastes,” I hedge, hoping she’ll drop the subject.
But Emily narrows her eyes, giving me her signature “I’m not buying this” look. She usually serves this to people in the office who try to pull a fast one.
“I know that look,” I say, avoiding her gaze, “It’s not going to work.”
I can feel Emily’s gaze burning into me making the tension between us very unpleasant.
“I just want you to remember how you asked me about my involvement with Wonderland,” she counters, “and now you can’t even tell me about this guy and his ‘alternative interests’?”
Damn it.
She got me.
It’s different though. Complicated. Leo had specially asked me not to divulge anything, and I still don’t understand why, but this man is trusting me.
“I can’t tell you,” I say firmly, “it’s not mine to share.”
Her expression shifts, and I can see the wheels turning in her mind.
“Alternative interests? Are we talking about the same interests involving dominance and submissive nature?”
My heart pounds in my chest as I realize she knows. Fuck, she’s always been too perceptive for her own good.
“I plead the fifth,” I stammer, trying to deflect.
Emily is relentless, shaking her finger in front of me with vigorous intent, “No, you can’t plead the fifth when you haven’t provided information. Now, tell me everything.”
I hang my head in defeat, knowing there’s no way out of this now, “I can’t,” I mutter, “You know I would if I could.”
Thinking about Leo, he didn’t say anything about not mentioning us being together, just not to mention names or him as owner—technically, I wouldn’t be breaking my word.
“Okay, okay. Yes, you are right. It’s someone who enjoys the dom/sub lifestyle.”
“Was that so hard?” Emily quips, leaning back with satisfaction.
“Actually, yes Emily, it is,” I retort, “this individual specifically asked not to reveal anything identifying.”
“That’s a little odd if I say so myself.”
“Is it though? Do you tell people you like to dominate men?” I said, revisiting our past conversation.
“Point taken,” she says, leaning back in the chair, crossing her legs.
The atmosphere in my closed office shifted to a much more relaxed demeanor. A little reminder to myself, don’t piss off Emily and invoke her dominatrix interrogation side—the bitch is scary.
“So what’s the issue?”
“I’m afraid of getting involved with this guy only to find out I’m not into the same interest and wasting both of our time.”
“Why are you holding yourself back? If you already know what this guy is into, then why even bother going through with those Friday plans?”
Hate it when Emily is right.
Leo’s different. The idea of being his submissive...intrigues me. When he dominated me that night, even just during the blowjob, I felt desired. Owned. It was thrilling in a way I’ve never experienced.
“Are you comfortable talking about this here?” I ask, glancing toward the office windows, checking to see if anybody was looking in our direction.
“The door’s shut, and I doubt anybody is listening to us. Half the office thinks our lives are full anyway.”
“Really?”
“Yeah, I have my informant keep tabs on floor conversation for me,” Emily told me with such a devilish smile.
I only shook my head smirking at her confession.
“Did you have any doubts about your first time? I’m not talking about your novice round with that ex-boyfriend, but with someone who was more mature and experienced?”
Emily uncrossed her legs and recrossed them, adjusting herself in the chair. She looked away from me and I could tell she was recollecting the first major experience she encountered.
“At first, sure. I was a little scared. Mainly because of the unknown and wondering if something horrible was going to happen to me. I went in with a complete stranger. Luckily, Wonderland made up for my stupidity by making it a safe space,” she stated, “From the sounds of it, you’ve been talking to this guy for a little while now?”
“I wouldn’t say a while, Em, but oddly I trust him—just by the way he talks to me.”
She gave such an odd look herself probably wondering how I can place trust into someone with little time we’ve shared. If only she knew everything, then Emily probably would fully understand.
And from her first experience, mine would be nothing like hers. Leo isn’t exactly a stranger and he wants to go on a proper date before anything else which to me sounds like he’s genuinely interested in me and making an honest connection, may that be between person to person and dom to sub.
There’s a lot to process before tomorrow.
“Thank Em for listening, and for your advice.”
“If you don’t want to do it, then you don’t have to,” she said, standing up from the chair, “BDSM is not for everyone and someone shouldn’t force you into it.”
I shook my head in agreement.
“But, if it does happen, I expect a full report over a bottle of wine. You hear me?”
My jaw dropped with a smile at her request.
“Yes, Mistress,” I grin.
“One last thing, if you do find yourself bound and loving it...get yourself a name.”
A name?
Why would I need a name? Couldn’t I just be Drew? I know if things move towards sessions, Leo becomes Master. Is having a name part of the rules?
That girl from that book didn’t have to pick a different name before getting chained, spanked, and fucked in that billionaire’s playroom, why do I have to?
So much to think about with so little time.
The evening arrived faster than I expected and now I’m sprawled out on my couch wearing only shoes and a bro tank. The glow from my phone screen reflects off the walls, and Apply Music hums softly in the background.
No matter how much I try to distract myself, I can’t stop thinking about Leo and his playroom.
Sinking deeper into the plush cushions, I unlock my phone and pull up the photo Leo took of me earlier. My eyes trace every detail—I’ve already looked at it more times than I’d like to admit–and an odd mix of curiosity and admiration stirs within me.
“He’s so fucking cute,” I mutter, the words slipping out unbidden. My voice, tinged with need, startles me.
My thoughts started to drift away from my worries to remembering how Leo’s mouth felt around my cock and the way he tugged on my balls that made my knees week.
I didn’t even know I liked that.
Next time, I’ll stay in the moment. No more tossing my head back or staring at the ceiling like some novice. I’ll focus on him—on those piercing blue eyes, the way they lock with min; on the sensation of his lips around me; on the softness of his thick blonde hair as I thread my finger through it.
If I’m even allowed to touch him like that.
Sliding the photo away, I go to Google and search for gay BDSM videos. My fingers hesitate before pressing enter. Porn probably isn’t the most accurate crash course, but it might at least provide a starting point—a window into the dynamics and possibilities of what I might encounter with Leo. It’s not the same as real experience, but for now, it’s the only way to satisfy my curiosity and prepare myself for the known.
The first video that pops up opens with a start, dimly lit room. Two men sit naked in sturdy wooden chairs, their bodies adorned with intricate rope patterns that constrict and frame their muscles. The rope winds around their torsos and limbs, binding their hands tightly behind their backs, the design precise. Even their cocks are encased, the tension in the bindings drawing a sharp contrast between vulnerability and control. A shirtless man strides into the frame, his leather harness gleaming under the harsh overhead light. Black gloves creak as he adjusts them, and his boots click sharply against the floor.
With practiced ease, he snaps sleep black collars around the men’s necks, the metallic clink of the leashes echoing in the silence. His commands are sharp and authoritative, his voice slicing through the air with such calculated dominance, bending them to his will like obedient pets.
“Next!” I said, swiping left on the screen.
The next video shifts to an industrial room bathed in shadows and streaks of cold metallic light. Suspended face down by an intricate web of ropes, a man’s body arcs into a graceful yet strained posture. His arms, like the first video, are drawn tightly behind him, causing his muscles to accentuate in sharp lines. His legs dangle parted widely, leaving him completely open to the scene unfolding around him.
The silence breaks in this one by the faint creak of the suspension ropes and the measured footsteps of two men entering the frame. Both wear leather harnesses that glint under the light, their movements in sync, exuding an aura of control. One holds a thin wooden switch, its polished surface reflects as he taps it against his gloved palm—a promise of what’s to come.
With a sudden flick of his wrist, the dom strikes the suspended man’s exposed flesh. The sharp crack of wood against him pierces the air, followed instantly by the sub’s cry—a raw visceral sound that echoes off the unforgiving walls.
“C’mon, I barely hit you,” the dom says, his voice tinged with a taunting edge that makes the power dynamic unmistakably clear. The companion smirks, stepping closer, his gaze fixed on their bound subject.
“If he’s going to be a little bitch, let’s fuck him,” he declares, tone casual yet charged, as if this was the most natural next step in their orchestrated display.
“Not for me,” I mutter under my breath, swiping again.
The next clip begins with the camera zooming in on a sleek, black-latex gloved hand moving with relentless behavior. The glove fingers thrust in and out of the sub’s rectum leaving nothing but an amplified squelching noise.
The sub’s body writhes between agony and ecstasy as his cries fill the space. Every motion of the dom’s hand thrust deeper , faster, growing the sub’s voice from high pitched moans to crescendoed guttural screams of raw desire.
The intensity of the scene grabs hold my sense, leaving me frozen, breath caught in my throat, unsure whether to look away or keep watching.
“Nope! Nope! Nope!”
My fingers scramble to find the X button, frantically flipping my phone over and placing it on the coffee table. My eyes widen trying to process what I just saw.
I pray that Leo isn’t into anything too extreme. Spanking? Maybe. Restraints? Sure, I could imagine the thrill of behind held in place, the ropes pressing against my skin, adding a sharp edge to it all. But the idea of a latex fist stretching and pushing behind anything I’ve ever considered. There’s simply no way, I’m tighter than a nun’s cunt.
What kind of trust would it take to surrender to something so overwhelming? The very thought makes me pull back. Is it fear? A quiet, unfamiliar curiosity? Maybe both, tangled together like a puzzle I’m not sure I want to solve.
A low, uncertain grunt escapes my lips. There’s no point in overthinking it—not yet, anyway. I’ll figure out what Leo’s into soon enough, whether I’m ready for it or not.
I picked up my phone again and opened the camera app. What I can give to Leo is a picture back since he requested and is expecting one since the other. After snapping a few shots, I chose the best one and sent it over to Leo. In seconds, a ding with his reply comes through.
“Handsome as ever. Thanks for the photo. Wasn’t sure if you were going to send one back.”
I smiled.
“Not good at taking selfies. Guess it’s one of my weaknesses. :)”
“Well, I think you’ve mastered the art of selfies. Heading to bed. See you tomorrow. Goodnight.”
“Goodnight.”