Page 5 of The Boss

Glancing at his profile, I tried to gauge him. “What about you? Did you always want to run a company?”

He seemed to consider that for a moment. “Not exactly. I knew I wanted to build something. To be in control of my own future. But the road to getting here wasn’t a straight line.”

I regarded him, curious. “What was it like, starting out?”

Isaac let out a breathy chuckle. “Brutal. Long hours, impossible expectations, people doubting me at every turn. They’d thought a brute-force jock could never become a sharp businessman. I took it as a challenge to defy the stereotype. When I was your age, I was a junior analyst at a consulting firm, working eighty-hour weeks, barely sleeping. My boss once told me I was too green, too soft, that I didn’t have what it took to lead. So, I worked twice as hard. Learned everything I could.” He glanced at me, giving me a knowing look. “Turns out, the best way to prove someone wrong is to outlast them.”

I tipped my chin, absorbing that. “Sounds intense.”

“It was,” he admitted. “But if you want to get ahead, you have to decide what kind of man you’re going to be. Are you the guy who waits for opportunities? Or the guy who makes them?”

I mulled that over, watching the buildings blur past the window. “I want to be the second one,” I said finally.

A small smile tugged at his lips. “Good. Then start now. Pay attention. Learn fast. Speak up when it matters. And don’t be afraid to take up space.”

I nodded, feeling the knot of tension in my stomach begin to unravel. By the time we pulled up to a small boutique nestled between a jewelry store and an art gallery downtown, any lingering awkwardness between us had faded away and I’d almost forgotten about the tear in my pants.

The shop before us was the kind of place that looked expensive before you even stepped inside. The polished brass nameplate by the door gleamed in the afternoon light, the swirling letters readingSullivan’s, and the window displays were a shrine to high-end fashion: Gucci, Louis Vuitton, Armani. Even the mannequins looked like they knew they were too good for the likes of me.

“Come on,” Isaac said, stepping out of the car with the effortless confidence of someone who belonged in places like this.

Inside, the shop was all warm wood and soft yellow lighting, with racks of pristine suits arranged like works of art. A faint scent of cedar and fabric dye lingered in the air, mixing with the polished tang of shoe leather. Two men stood behind the counter, examining the roll of fabric stretched over it: a younger, lanky man with round glasses, and a short, gray-haired man in his sixties. Both raised their heads at the sound of the bell above the door as Isaac and I entered.

“Mr. Steele!” The older man called out, coming around the counter to greet us. His tailored suit was impeccable, and his smile was a mixture of genuine warmth and the practiced charm of someone who catered to the elite.

“Edward,” Isaac said, extending a hand. “How do you do?”

“Oh, I can’t complain. But I wasn’t expecting you today—your wedding suit is still not ready.”

“I’m not here because of that.” He grabbed his jacket off my shoulders and pushed me in front of him, turning me around so that my backside faced Edward. “This is Chris. He’s new at Nova Systems, and, well, he’s had a bit of a wardrobe malfunction.”

Edward’s eyes flicked to the tear in my pants, and he let out a soft chuckle. “I see. Welcome, young man. We’ll have you sorted in no time.” He left the store in the hands of his younger associate and led us deeper into the shop, past rows of designer labels that made my wallet ache just by looking at them.

“Feel free to pick whatever catches your eye,” Isaac said, his tone casual.

“I—uh—thanks, but…” I trailed off, staring at a price tag that was easily more than a month’s rent.

“Don’t worry about the cost,” he said, brushing off my hesitation with a wave of his hand. “I’ve already said it’s my treat and I don’t like repeating myself.”

Well, the manwasmy boss, so I decided to shut up and do as he said. In the end, I settled on a deep navy Tom Ford suit, classic but not too formal. Edward nodded approvingly and gestured for me to follow him to a fitting area tucked away at the rear of the shop.

“Right this way, young man. Let’s see what we’re working with.”

Isaac stayed behind, texting on his phone and roaming around the store.

The fitting room was cozy and lined with mirrors that made it feel larger than it was. Edward gestured toward a small bench where I could set my things. “Strip down to whatever you’re comfortable with. The fit needs to be precise, so go with what you usually wear under the suit. This usually means your underwear, but some men prefer to go without.”

I considered his words, then figured my lucky jockstrap had already seen me through one disaster today. Why not double down?

As I undressed, Edward moved with the practiced efficiency of someone who had done this a thousand times. But his eyes never left me, his gaze sharp and focused as it swept across my almost-naked body. When I was finally standing only in my jocks and my socks, Edward’s mouth opened a little, like he was about to gasp. Instead, he told me to step onto the small dais in front of the largest mirror.

Measuring tape in one hand and a small notebook in the other, he danced around me humming softly to himself while he took notes. He measured my shoulders and my chest, my biceps and my waist, my thighs and my calves, all the while making comments—“broad chest, excellent posture, prominent backside”—bordering on personal. Years of wrestling had killed any trace of shyness in me so I felt at ease, almost like a model in an art class.

Edward’s touch lingered just a fraction too long as he measured my inseam, the back of his hand grazing my balls. It was the most action I had in a while, and despite myself, I felt my cock stirring to life.

“The secret of a perfect suit is customization,” Edward said, his tone almost confidential. “Anyone can come and buy a suit off the rack. But with the small, careful adjustments, you get a personally tailored fit that becomes a unique work of art.”

“How long will that take?” I asked, eyes on the mirror, trying not to get hard.

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