I spent a few minutes admiring the view of the river from my room’s window. Chicago looked new and even though I loved the old architecture at home in Boston, it was nice for a change. Later I’d be walking down to Boy’s Town. Before that, I had work to do.
Since we were only there for one night, I hung my garment bag in the closet and didn’t bother unpacking anything. Instead, I took off my tie and jacket and hung them over the chair at the desk, grabbed my laptop, and got busy making sure all the reports Mr. Sutherland would need for the meeting the next day were in our shared drive and clearly labeled so he could just open them on his tablet when he needed them.
Three hours later, the sun was setting and the illumination on the buildings outside the window flickered on, turning the city into a clean-lined forest of light. It was still too early for me to hit the clubs, and I knew hotel shifts well enough to know Carlos wouldn’t still be working. I thought about going to the hotel gym for a workout, but I’d spent two hours in the gym before the flight, so wasn’t really in the mood. So, I turned to my usual time killer.
I closed the curtains, blocking out the rest of Chicago and picked up the television remote. I could have just geared up some porn on my laptop, but jerking off at Mr. Sutherland’s expense made the usual masturbation sessions a little more exciting. Also, when I went down to see Frank in accounts payable every month, he got a kick out of seeing the names of the movies I ordered. The first time they showed up on the expenses, he’d had to adjust his cock twice while he asked me about them. Ever since then, we’d taken it as an opportunity to close his office door and reenact my favorite scene from the month. He had a great ass and a great mouth, so he’d be disappointed if I didn’t charge porn to the company.
Thankfully, upscale Chicago hotels had plenty of gay porn to choose from. I flicked through the menu. Doctor porn… a particular favorite of mine, but I was a little burned out on it. Lumberjacks, a swim team. I wondered if the sport of curling had any porn associated with it. Then I saw my favorite. A gang of straight guys with no other way to get their dicks wet have to start fucking each other. Jailhouse, forced fucking. My cock responded immediately. Without even having to think about it, I click ‘yes’ when the screen asked if I wanted to pay the twenty bucks to rent the movie.
Why the idea of a straight dude pushing my head down on his cock and using me like a fuck-doll got my blood pumping was something I didn’t want to think about. And, I didn’t have to. It was my fantasy and they don’t need justification.
I pressed play and reached into my pants, running my fingers over the sensitive skin of my already throbbing cock. I’d only intended to use the porn as a warm-up for my night out. But, I never had a problem getting off a couple of times in a night. I could bang one out to the porn and still go find some strange to bring back to the hotel.
I undressed, folded my clothes, and checked myself in the mirror as the opening credits rolled. I’d been right not to worry about working out. Since Mr. Sutherland didn’t care what I did during the day when we were on the road, I’d spent a lot of time in the hotel gyms. Every time I thought it, it felt a little creepy and cliched, but—fuck yeah, I’d do me.
I had to keep my curly, man-bait hair under control to look like the ultimate businessman. The rest of me from my green eyes and sharp cheekbones down to my tanned toes was fuckable.
Fuckable and travel-icky. I always felt a little off after traveling. It took a lot for me to hit pause on the movie as the poor unsuspecting fresh-meat prisoner as told to drop trou and get ready for inspection, but I wanted to be clean and relaxed.
As soon as I stuck my head under the water blasting from the shower head, the stress of the trip, my anxiety about the room arrangements, everything, melted away and ran down the drain. I sort of hoped nobody was in the room next door, but it really didn’t matter, while the water forced suds out of my hair and steam surrounded my body, I belted out songs to get myself pumped for a night out.
I was still singing as I stepped out of the bathroom, rubbing the towel vigorously over my head, trying to give my hair as much of a head start on drying as possible. My curly hair was thick, and it took a while.
At a particularly loud part of the chorus I whipped the towel off my head… and trailed off.
A bellhop stood frozen, staring at me with his mouth open and Mr. Sutherland sat next to his suitcases on my bed.
I jerked the towel in front of my still semi-hard cock and sputtered. “Wha… I mean… why…?” Then I stopped trying to talk. Surely I could be forgiven for not being my usual, articulate self under the naked, singing circumstances.
The bellboy closed his mouth and Mr. Sutherland handed him a couple of bills. “Thank you,” he said, dismissing the kid who snuck a few more glances at me as he headed for the door.
Collecting myself, I wrapped the towel around my waist and walked as calmly as I could to the closet where my garment bag hung.
“Don’t worry about the nakedness,” Mr. Sutherland said. “I do go to the gym. No need to be embarrassed about that. But, the singing… that’s another story.”
My already heated face grew even hotter. Without turning around, I rummaged through my bag for underwear and jeans. “So, what’s the story here, sir?” I asked. Okay, maybe mumbled.
“Lara got a call from her husband who decided to surprise her. He was at O’Hare and asked what hotel she was in. I had to split.”
Damn, I thought. My night was fucked.
“Since someone made a mistake and we don’t have a third room, I have to crash here.”
How he spoke of something he’d obviously done so dismissively was beyond me.
I slipped my underwear on, still not turning around.
“So, what were you watching? Is this that old prison show Oz?”
My stomach clenched, and I almost threw up as I spun around to stop him, but it was too late.
“Bend over the table,” came from the television in Dolby Digital Surround Sound.