My wife always giggled when I showed her my latest assistant. I had a penchant for young, eager boys looking for the first rung of that corporate ladder. Simple eye candy to toy with my homoerotic side, and never anyone that could threaten what I had with her, and she knew it. A little fantasy. These boys would stay on for a bit, maybe initiate or engage in some casual flirting, but the job was always first: I wasn't about to jeopardize the career I made just for a physical fling with some twink in a suit (although some of them tempted me to do so). But during their tenure I'd give them guidance in the biz, make some connections for them, and then they would move on. I stayed in touch with several, and always celebrated their successes.
Of course, once the job was open I got to interview a new batch of promising business upstarts with hopeful resumes listing top-notch credentials.
"Uh-huh," my wife would say, as I conferred with her about my final few candidates. "And which is the cutest?"
Alec had come from a solid school with top marks, and in his interview was grounded, relaxed, and had that air of someone ready to learn and ready to hustle.
He came in just at the right time: quarterly reports, budgeting meetings, traveling to branches...it was all a lot to handle and Alec slipped into the overload of dates and times and emails like a champ.
I needed to take a weeklong trip out to Arizona for a set of pretentiously boring, seemingly needless meetings. On weeklong trips, I usually brought my assistant, and maybe Amy, my secretary.
As fate would have it, a snafu with booking meant we had two rooms to split between the three of us at the hotel. Alec apologized and tried to sort it out while Amy and I had martinis at the bar.
Amy, discreet and indispensable, was my age and off-limits. If anything were to happen between us, it would've happened long ago, and it didn't.
"I'm so sorry," Alec said as he came into the bar from the front desk. "I've made a big blunder. I'm so sorry."
"Oh, don't you worry about it," Amy said to the boy. "Your boss doesn't mind, do you boss?"
"Of course not, it's okay," I said, playfully. "You can bunk with Amy. She'll keep you up watching old episodes of The Golden Girls."
"Are you kidding? These trips are the few opportunities to be away from two teenagers who think they're adults and a husband who thinks he's a teenager. I'm keeping my room for myself, thank you very much."
"Would you like me to try and book you a room somewhere else?" Alec asked.
"No, we're going to have a few late nights with these meetings. Late nights will be paid for, both in hourly wages and in room service, before you even ask, Amy. I just want
you
to be comfortable, Alec. Okay with you?"
The young man blushed. "Sure. If it's no trouble."
Amy said, "It's no trouble."
Our first few days of marathon meetings and appointments kept us on the run. By the third day, I was ready for a break, and called for a halt. I told Alec to reschedule the anything we had after 3pm, so we could all take a breather. I sent Amy away with the company credit card to go "entertain clients," meaning she could go order for two at whatever restaurant she wanted to, plus have a spa night.
"I thought I'd hit the pool," Alec said.
"There's a pool?" I said in mock-surprise. "There's life outside this schedule?"
He laughed.
"Okay, you hit the pool and let me know what you want for dinner. Since Amy's got the card, I'll give you one of mine."
"You should hit the pool with me," he blurted out.
"I don't have a bathing suit," I said.
An hour later, I was standing in our hotel room across from Alec, holding up the "bathing suit" he had rushed out and bought for me.
"Where's the rest of it?" I asked.
"It's a
Speedo
." He avoided eye contact as he put tanning oil and a towel into a shoulder bag. "I've seen enough of you to know you can make it work." He caught my eye. "Uh. Sir." He then pulled out the one he bought for himself without looking at me again, and went into the bathroom. After a few minutes, he came back.
Alec was hot. Incredibly hot. Tall, skinny, toned. Hairless. An androgynous look that was tough not to drool over. And he was wearing a pair of bright yellow bikini bottoms showcasing a disproportionately large, coiled cock that proved his own bathing suit was perhaps a size too small.
He tried to act casual, finally putting a water bottle into the shoulder bag.
"You think I'll look like that?" I asked with my hand out to indicate all of him.
"Probably better," he said. His suit seemed to be getting smaller, and he blushed as he covered it with his shoulder bag and said quickly, "I'll be out at the pool, charging margaritas to the room."
I'd been keeping in shape, so I wasn't worried about stepping into this tiny outfit, and in my experience with any pool in America, you're never gonna be the worst-looking one there. I was actually delighted. I showered quickly, slipped it on, positioned my bulge, laughed. I checked in with my wife, who laughed at the pictures I sent. We had a quick conversation about Alec, and she gave assent to anything that might happen. "If he doesn't fuck you," she quipped, "I'll book a flight out there myself."
The pool area was empty, the desert beyond, except for Alec, laid out on a beach chair like a movie starlet, one leg extended, one knee drawn up, sunglasses, his giant bulge straining from his tight suit, and he was already slick with tanning oil.
"How do I look?" I asked.
He pulled his sunglasses down and looked at me.
"Good to know I can do your shopping for any occasion," he said.
I laid out. A waiter came with a pair of margaritas. And then another pair. And then some tapas. The sun baked us, and we were having a good time, mostly talking about the people we were meeting on the trip, business quickly turning to gossip, gossip quickly turning to flirting, and all the while I couldn't help but realize I was going to fuck my assistant.
