Chapter 3
I check myself out in front of my standing mirror, making sure that I not only look good but feel confident.
I’ve chosen to wear black slacks and a dark green dress shirt that I’ve been told looks good with my skin tone.
I feel ridiculous for being nervous about meeting Chase at Midnight.
I sent him home a little over an hour ago to change, then told him we would meet for a drink to test out what a date would look like.
I let out a controlled breath, then spray on some cologne before heading out with my wallet and keys.
The walk is easy and helps me focus in on my intentions for tonight with Chase.
I look around, but don’t notice him outside, so I make my way in, then through their greeting process, choosing a green bracelet like always, I make my way to the bar.
The club is nice with low blue lights, a dance floor in the center, and there are two options for a bar on either side of the room.
There’s a mix of cocktail tables and booths with multiple servers and bussers roaming around.
I order a whiskey sour, then watch the club waiting for Chase’s arrival.
But I’m surprised to quickly find him sitting at a booth by himself, looking handsome and nervous.
He’s obviously showered and styled his hair differently to what he normally does for the office, so his curls are more defined.
He’s chosen to wear something similar to me, but went with a dark blue dress shirt that brings out his eyes and matches the decor of the club.
I make my way over to him, watching him flick his eyes around the room until he spots me.
His smile immediately becomes blinding, and I swear I see him bounce for a moment.
It worries me that I may get too used to his excitement when seeing me, and it would be a pity to watch that fade.
I shake that thought away. I haven’t even decided if this will move past tonight.
I open my mouth to greet him, but he blurts out, “you’re so handsome!”
I sit down beside him, and he quickly presses into me, almost on my lap. Has he always behaved this way, and I just misread him? “Thank you, you look handsome as well.”
“Thank you, daddy,” he says easily. “What are you drinking?”
“A whiskey sour,” I answer, then frown, noticing the table and his hands are empty. “Do you need a drink?”
“No, I’m a bad drunk,” he says with a wince.
“It’s good to know your limits,” I praise, and his smile splits across his face. “I think it would be nice to get to know each other.” He nods eagerly, “why don’t you tell me about why you chose to pursue law?”
He frowns, “I already told you because of that night at the Christmas party when-”
I cut him off by raising my hand, “yes, I know, but I figured that wasn’t the only reason.”
He shakes his head, “that’s the only reason.”
I hum, sweeping my eyes across the bar, “okay. What were you doing before working for me?” He shrugs, and I tsk, which causes him to freeze. “Avoid shrugging, it’s very dismissive.”
He apologizes while nodding, “I was in school for a business degree. Why are you a lawyer?”
“My father was one, and I felt becoming a lawyer myself would make us closer,” I answer more honestly than I would typically. Now that I have chosen to see Chase in another light, I’ve quickly realized how comfortable I feel around him.
“Did it work?” He asks while threading his fingers through mine.
It feels odd to be so public, so open with affection.
I’ve never really dated anyone who’s been like this.
Oliver was very PDA to me, and he only kissed my cheek in greeting, though I don’t find myself overly bothered by Chase’s touch, his desire to be near.
“No,” I sigh, “but I love it now. What would you be doing if you weren’t working for me?” He shrugs but stops midway and slowly straightens while flicking his eyes to me, then at the table. “Thank you for listening and trying,” I compliment.
He smiles, then asks, “can I get a kiss? Like a reward for trying?”
I can’t help but laugh while he climbs into my lap. I grab his hips, stopping him from getting completely settled. “Chase, no,” I try to seriously chastise, but I can’t stop my smile.
“You said you would give me a chance, and daddies give their boys rewards,” he argues, even though I’m not.
“Boys also don’t argue with their daddies,” I counter.
He frowns and runs his hands down my shoulders, making no move to leave my lap. “But I stopped myself from shrugging, like you asked.”
“You did, and I complimented you, but do you think it’s appropriate to sit in my lap like this when we’re at a bar?” I ask, tightening my grip on his hips to nudge him away.
“But it’s Midnight?” He asks, tilting his head to the side. “People are fucking in the rooms back there and-it’s a kink club for sex?” He shows me his red bracelet, then frowns when he sees mine. “Why is your bracelet green?”
I pat his hip and nudge him to sit beside me, which he does, but scoots close so our thighs are pressing together. I put my arm on the seat behind his back and explain, “when I come here, I always get green, so it was more out of habit.”
“I think you should chang-” he starts, but gets interrupted by a man similar to his age.
“Chase?” The man asks with a charming smile. He’s handsome with shoulder length brown hair and a fuller figure.
“Hey, JJ,” Chase greets with a smile.
JJ points at me, “you look familiar.”
“Shut the hell up,” Chase rushes out, alternating from glaring at JJ to giving me nervous looks.
I reach out my hand, “I’m Luke,” I’m cut off my Chase’s loud gasp.
I look at him with a frown, “why does he get to call you Luke?”
“Because he doesn’t work for me and like you said earlier, this is a kink club, so formalities aren’t as necessary,” I answer with a teasing smile.
“Not necessary? But you wouldn’t let me sit on your lap,” Chase scowls at his legs while drawing a pattern on his thigh.
“Well, maybe it’s because you’re being too needy, baby Chase,” JJ teases. He looks at me with a smirk, “maybe your sir here is more open than you are.” He flicks his eyes to my bracelet, then meets my eyes.
“He’s changing it!” Chase snaps, clearly in distress. “Stop flirting with him.”
“Baby Chase, you need to calm down, or you’ll scare away the man,” he replies. “You already got a lot working against you.”
Before Chase can comment back, I raise my hand, “it’s nice to meet you, JJ, but if you don’t mind excusing us, we’re on a date.
” JJ says goodbye with a smirk, and I catch Chase from the corner of my eye, sticking his tongue out.
Sighing, I move on and ask, “why do so many people call you baby Chase?”
He immediately looks embarrassed, “I guess, sometimes I stomp my foot when I’m angry, and I look like a toddler when I do it.”
I hum, then ask, “now where were we?”
“You were going to explain why I can’t sit on your lap while we change your bracelet to red,” he answers, going to stand.
I stop him by grabbing the back of his neck, and he settles down into his seat. I leave my hand lightly holding his neck, then correct, “no, you were going to tell me what you would be doing if you weren’t working for me.”
He shuffles closer to me, drawing a pattern on my thigh. “I don’t know. I never-I don’t have any motivation or what’s the word, ambition to have this great career. You know, like my dad, I don’t want to be a leader or a boss. I just want a job that I like, and that’s all.”
I nod, “that’s fair.”
“You’re not disappointed that I have no ambition like you?” He asks, looking briefly at me before looking at his fingers on my thigh.
“Different things are important to people. Some people want great careers, while others value family more, or want experiences to look back on. Neither is better than the other. It’s just your preference, so no, it doesn’t bother me,” I answer, then tease, “though, I would prefer that you do better at your job.”
He huffs with a smile, “I will if you give me a kiss as a reward. Some of the things are so boring and hard.”
I laugh, “okay.”
He snuggles into my side, wrapping his arms around my waist. “Do you think we know each other enough to have sex?”
“Is that all you care about?” I ask with a smile.
“Right now, yes,” he answers quickly, “my cock hurts, daddy.” He grabs my hand and puts it on his crotch, forcing me to feel his hard cock.
“What is making you hard right now?” I ask, teasingly.
“You,” he answers, “and every time I shift, I get tingles of pain from my ass. The one you spanked earlier.”
“Let’s go back to mine,” I say, standing with difficulty since he doesn’t let me go.
We leave the bar, then walk back to my house with Chase wrapped around me. It’s awkward, but also endearing. It’s nice to be bordering on suffocated by his affection and neediness. There’s no guessing with him. I’ll always know his feelings, and most importantly, how he feels specifically about me.
Letting us in, I then lead him right up to my room, where he quickly kicks off his shoes, then climbs on my bed.
Without prompting, he strips out of his clothes, then spreads out on my bed like a starfish.
I tsk as I take him in his naked glory, so unselfconscious and ready to be viewed.
Which makes sense, since his body is well defined and fit without a single blemish or even a freckle.
His cut cock is still hard with a flushed, thick mushroom tip and a long shaft with groomed pubes at his base.
Though I do appreciate his balls being shaven, and I hope his ass is as well.
“It’s your turn to be naked,” he remarks.
“Is that so?” I ask, “I thought I was the daddy, and you were the boy.”
“You are,” he says with a frown, sitting up. “You’re my daddy, and I’m your boy.” He crawls to the end of the bed and kneels, looking at me. “Please, daddy, can I see you naked?”
“Oh, the boy can say please,” I tease as I unbutton my shirt, then toss it aside. “I wasn’t sure you were capable of manners.”
He frowns deeper, “I’m good, and you still owe me a reward for stopping myself from shrugging.”
I hum, “does a boy get to choose when he gets a reward, or does the daddy?”
“Daddy,” he mumbles. I continue to hum and pull off my belt, then let my pants slip down my legs. “How do I get a reward?”
“All you care about is sex and rewards,” I tease, “I thought you loved me.”
“I do!” He shouts, “I love you, and you’re going to love me. I just want to have sex with you, too. I want to know what it’s like…and yes, I like rewards, and really want one from you because it feels nice when you give me compliments. And I think you’ll be a good kisser.”
I step closer to him, and he reaches out, threading his fingers through my chest hair. “Show me your marks from your spanking.”
“Yes, daddy,” he says.
He eagerly turns around on his hands and knees, showing me his reddened ass.
Not being able to help myself, I spread his ass cheeks to see his hole.
He’s shaven with a tight pucker that I can’t wait to stretch open.
I run my finger along his hole before circling his rim as he clenches, trying to suck my finger in.
When his attempt fails, he tries to push back on my finger when I tap against his hole.
I give his ass a slap, then step back to which he lets out a whimper while looking back at me.
“I was going to give you a reward for listening and showing me your ass,” I say, and his smile is blinding as he sits up, then turns around to face me. “But,” he frowns, “you didn’t stay still instead, you tried to force my finger inside of you.”
“You’re teasing me too much,” he complains.
“And you promised me a good boy,” I counter.
He draws a pattern on his thigh, then mumbles, “I’m trying to be good. It’s just hard because I’m so excited and happy.”
I try to stay stern, but I can’t hold back my smile at his words.
I can’t believe this boy, and how sincere he sounds.
I can’t believe this morning I had him so misread, though I still think he’s trouble.
I step forward again, cupping his cheeks to tilt his face toward mine, then give him what he’s been wanting.
I kiss him, and he immediately whimpers into my mouth as I deepen it.
His arms come around my waist, holding me tightly.
We kiss as my hands thread into his hair, and his hands rub up and around my body.
I pull back, and he follows me, but I step back, breaking contact.
“Such a good reward, daddy,” he says happily.
I walk around the bed to my side table, and he knee walks, so he’s beside me.
Pulling out lube and leaving my side table open, I turn to face him.
Only to realize he’s been tugging my briefs down without me realizing, he’s got them half off my side.
When I don’t say anything immediately, he pulls them the rest of the way off.
He freezes, and I’m hit with the realization that I assumed he knew I’m trans.
I pass easily for a cis man, which feels both amazing and a bit unnerving.
Like I’ve finally accomplished something I desired for so long, but there’s still a part of me that’s waiting for the rug to be pulled, to be accused or sneered at.
My younger years have not been kind to me, but in the last decade, my aging has complemented my masculinity. That and some surgical help.
He shuffles closer, then kisses my stomach before looking up at me. “I just need you to tell me what to do,” he says, embarrassed and a bit shy.
“What?” I ask, softly, still feeling stuck in my head about how to handle this if things have changed.
“I’ve never done anything before,” he answers. “Not nothing, like I’ve kissed before, but outside of that, nothing.”
“Really?” I ask.
He shrugs, and I let it go as he answers, “it’s always been too much pressure. Whenever I got close, I would panic, then freeze, then run away in the nicest way I could.” He shrugs again, but stops himself midway and mumbles, “I’m sorry.”
“Do you want to stop?” I ask, feeling wary.
“No!” He says quickly, “I want to have sex with you, and I feel good about it. It’s different with you,” he explains, “I feel nervous, but I know you’ll take care of me.”
“Okay,” I reply, and climb onto the bed while he wordlessly lies down, then pulls his legs to his chest. I kneel at his ass, tossing the lube beside him, then rub my hands up and down his calves. “We should go slow-”
“No!” He shouts, “I’m ready, daddy.”
“You don’t want to kiss for a bit?” I ask, and he immediately looks conflicted.