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Story: Dirty Daddies Pride 2025 (Dirty Daddies Anthologies #7)
Chapter Two
Grant
The steak was already marinating. The wine—something young and overpriced that sweet Colby would pretend to like—was chilling. And I’d spent fifteen minutes debating whether to light candles before deciding it was too much.
I wasn’t trying to send a message.
Or if I was, I hadn’t admitted it to myself yet.
I couldn’t.
“Jesus, Ellison, get it together,” I muttered, looking over the place settings one last time.
Most of the sugar babies I’d contracted with in the past expected to be wined and dined in Boston’s finest restaurants, but I’d gotten in the habit of scheduling most of my dates with Colby here at home.
He liked the penthouse. Said it made him feel “fancy.” Which, coming from him, had been equal parts joke and genuine delight the first time he’d said it.
And nice dinners at home, where I actually got to cook for someone else and could selfishly have all of Colby’s attention on me, suited me just fine.
I liked seeing him in my home. Probably too much.
And I really liked the endearing expression he’d sometimes get on his face—glimpses of wide-eyed wonder behind his constant smile, like he couldn’t believe he was allowed here even though it was clear, to me at least, that it was right where he belonged.
And… fuck. My heart contracted painfully with the knowledge that I wasn’t going to have many more chances to see it.
The Seattle move was happening whether I liked it or not.
The new development project had been locked in for months, and between permits, construction schedules, and pre-sale timelines, I’d be west coast–based for at least a year, while I knew Colby planned on interviewing locally once he got done with school.
Of course he did. His whole family was in the area.
But that meant no possibility for an extension to our contract.
No adjustments to the terms.
No last-minute rewriting of an agreement I’d worked hard to fill with ironclad clauses so the boys I spent time with would know it wouldn’t last.
And so I’d leave no room for the kind of mistakes I’d already made with Colby.
Getting too fucking close.
Letting my heart get involved.
Wishing for more.
With the boys who came before him, it had been easier. I gave them attention, cash, and gifts. They gave me company, some sexual gratification, and let me feel needed for a while. Then we said thank you, parted ways, and everyone moved on.
It had been satisfying, but not romantic, and that had been by design.
But Colby had slipped past every boundary I thought I’d locked down, and now…
“Fuck,” I sighed, knowing damn well I’d dug this hole myself.
I glanced at the clock, hating that he wasn’t here yet. Not because he was late, but simply because I missed him.
Colby was always punctual, though. Always perfect in just about every damn way I could imagine. And right now, that meant I still had more than half an hour to wait before I could pull him into my arms again and satisfy this ever-present need to hold him, make sure he was okay, just…
Just be with him.
I wasn’t even sure why that was so satisfying.
It wasn’t just because he was beautiful, though he was—lean and bright-eyed, all nervous energy wrapped in that disciplined, “good student” polish that was like catnip for me.
It was also the way he listened. The way he tried so hard, never satisfied to meet expectations but always wanting to exceed them.
Even when I hadn’t asked.
Especially when I hadn’t asked.
He didn’t just want help with his finances, although he needed it, and he didn’t get excited about the material gifts I occasionally spoiled him with although he was always wonderfully appreciative of them.
No, my baby?—
Colby , I meant.
Shit. I’d tried to avoid pet names with him and kept failing miserably, because he felt like my baby. My boy. And that sweet boy? Once his basic needs were met—tuition and rent—the only thing he seemed to want from this arrangement was to be good for me.
It made something quiet inside me ache in a way I hadn’t felt since the early days of the marriage that had gone so wrong.
I grimaced, pushing that thought aside quickly. The divorce had been ugly, sure, but it was long over. I didn’t want to poison one of my last remaining nights with Colby by thinking about any of that.
The only memories I wanted to replay in my head while I waited for him to arrive were the ones of him.
Colby had come into our arrangement with that same wide-eyed mix of desperation and pride I’d seen a dozen times before with the boys who decided, for whatever reason, that a sugar daddy was the right choice for them.
But instead of retreating behind charm or aloofness once we’d signed the contract, Colby had leaned in.
Been sweet, open, and sincere. Enthusiastically shared his interests and asked about mine.
He even took notes—literal notes, once, when he got me talking about the real estate development business I’d spent the last couple of decades building up, just so he wouldn’t forget.
So he could be good for me.
He’d flushed when I caught him doing it, tried to play it off, but I’d been flattered.
Most boys liked the penthouse. The dinners. The gifts.
Colby liked me .
And I… fuck. I was starting to think that I more than just liked him.
That was the problem.
The more Colby opened up, the more I wanted to do the same.
The more I found myself watching his face for the smallest shift in expression.
Texting him dumb things just to make him laugh.
And the part of me that knew better—the part that remembered what it felt like to build a life with someone who ultimately betrayed me—kept warning me to pull back.
But I hadn’t.
I couldn’t.
Not with Colby.
Instead, I started letting him stay longer than the contract required after our scheduled dates. Held him, perfectly content, when he dozed off on my shoulder after stressful weeks at school a few times, and pretended to myself that I didn’t notice how natural it felt.
I’d offered various kinds of help without him asking.
Set reminders in my phone for his exams.
Picked up his favorite snacks and made sure to always have them on hand.
All things a good Daddy might do, even after I’d explicitly told him we weren’t doing that.
Even after I told myself I wasn’t doing that.
I pinched the bridge of my nose, trying—and failing—not to think about how beautifully he responded when I gave him structure, guidance, direction. How quickly his breathing calmed whenever I took control. How much he fucking blossomed whenever he realized he was pleasing me.
Goddammit. I’d sworn off trying for anything real again after my divorce. I’d told myself I was done being that emotionally invested in anyone ever again… no matter how much my heart craved caring for someone who truly needed me.
The sugar arrangements were a compromise—temporary, boundaried, safe.
And, for a while, satisfying.
Then came Colby.
With him, I’d started to want something that wasn’t temporary. That had very, very different boundaries. Something that wouldn’t keep my heart safe at all.
Worse, I’d started imagining what it would be like if the contract didn’t have an end date. If I could come home to him every night and wake up to him in the mornings. If I didn’t just have a few more weeks to take care of him, but if I could do it…
Well, for as long as he’d let me.
I sighed, long and loud, fluffing the risotto while I lost patience with myself. I wasn’t sure who I was trying to fool here.
Oh, yeah. I guess that would be me .
Still, I’d come this far. Why lie to myself now? I didn’t want to take care of him for “as long as he’d let me.” The sweet boy had me dreaming of taking care of him forever .
Jesus. I was seriously screwed.
Thankfully, the elevator pinged before I could spiral any further.
I checked the time. It could only be Colby, but he was early. Twenty minutes, at least, which wasn’t like him.
And the moment the doors slid open and I saw him, my pulse kicked hard in my chest, telling me that it, at least, didn’t care about possible. It just wanted him .
But fuck, his usual bright smile was missing. He stepped into my foyer like he wasn’t sure he was supposed to be there, his eyes darting up to meet mine like he was checking for disappointment.
“Hey,” he said, soft and breathless, but sounding unaccountably nervous too. “Sorry. I’m early. I didn’t—I didn’t want to be late, and then I got ready faster than I meant to, and?—”
“Colby,” I cut in when his voice started to become high-pitched with anxiety.
Just his name—but it was enough. His mouth snapped shut, his shoulders dropped, and I watched tension drain out of him in real time.
Because I’d stepped in. Taken control.
And there it was again—that dangerous throb in my chest. The sharp certainty that this was going to hurt like hell when it ended.
Because that was still the plan.
Wasn’t it?
Fuck.
“I’m always happy for more time with you, baby. You never have to apologize for that,” I said, forcing myself to save the bigger questions for later.
Right now, he needed reassurance. He needed me .
He flashed me a quick, hopeful look as I stepped back to let him pass, internally wincing over having slipped up— again —and dropped a “baby” in there.
“It smells really good,” he said quietly.
Sweet boy.
“Dinner’s almost ready. We’re going to eat in the kitchen.”
Not fancy, but I knew Colby wouldn’t mind. And it felt more… intimate. Comfortable. Kind of wonderful, in a way that eating out at a Michelin-star restaurant couldn’t compare to.
He nodded, quick and obedient as always, but still didn’t give me his usual smile.
I frowned as he walked ahead of me. His hands were tucked in the pockets of his jeans, shoulders drawn up just enough to tell me that something was off with him.
Table of Contents
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