I was vacationing in Chicago in the summer of 1975. A hot older man had taken me home from the Gold Coast, the Windy City's hottest leather bar. He and his friend Tom had kept me in different forms of bondage and abused me in adorable ways from Friday night through Saturday evening.
On the way back to my hotel, Tom had used the opportunity of a massive lake storm blowing by, to fuck me one last time in the cab of his truck. Once we arrived, he'd kissed me and given me a dollar bill with his phone number written on it. As I got out of the truck I noticed a big bear of a guy was watching Tom and I. When I walked up to the reception desk, I was surprised to find the same guy standing next to me.
While one clerk dealt with him, Juan, the other night clerk, bustled over to assist me. Earlier that week, when I 'd been checking in, he'd seen me staring lustfully at him and had cruised me right back, grinning knowingly at me in a way that no straight man would ever do. When I blushed like a schoolgirl in response that had only confirmed his suspicions; I was yet another vacationing fag hoping for sex in the big city!
I had good reason for staring since he was seriously hot; about ten years older than me, with dark hair and dark features and a chunky, muscular body. I'd fluttered my eyes shamelessly at him over the next few nights, fantasising about what I imagined must be a long, uncut Latin dick. But it was all to no avail; Juan was sensible enough not to mix it up with the paying guests.
He was just as cool and sexy now; he was one of those guys who looks good in any kind of uniform and this one fit him perfectly. So perfectly that I felt severely underdressed by comparison in my skin-tight jeans and t-shirt ensemble. I was flustered and he knew it, grinning conspiratorially at me while speaking politely in front of his colleague.
"Sorry, Mr. Davis, but while you were away, water leaked overnight from the bathroom above your room. Since we had workmen going in and out, we moved your things to a new room. We'd like you to check that nothing is missing, so do you mind if I go up with you now?"
He picked up my new room key, told the other clerk he'd be away for a few minutes, and led me over to the elevator bank. As he pressed the button for my new floor, the big guy from the sidewalk jumped aboard, and pressed the same button.
As the ancient and awfully slow elevator made its creaky way upwards, Juan spoke to the guy, who he called Mr. Steenburgen, remarking how unusually quiet the hotel bar had been so far that evening. As the guy muttered something in reply, I became uncomfortably aware that the guy was staring remorselessly at me.
"Well, young man, you're getting first-class treatment tonight. A Chauffeur to the front entrance and a personal escort to your room. What do we have to do to deserve that, eh Juan?"
By the time Juan had finished explaining to him that I was being moved to a new room since my old one had been damaged, the elevator he reached our floor. The big guy walked down the hallway alongside us and went into the room directly opposite mine. Once we were safely inside my room, Juan immediately turned to me.
"I don't trust that old bastard. He's a married, retired cop from Milwaukee. He comes here every couple of months and hangs around the hotel bar buying drinks for young guys. The hotel's got a special rate for the military, which means there's always a few boys here on R and R. He gets a not-quite-straight one to go upstairs with him, and if not, he calls a service and rents one.
"Later on, the hustlers have been paid and the others are either too drunk to remember or too ashamed to admit it. Either way no one complains, and I'm the only one who notices. The bar was quiet tonight, but it stays open till two; I just hope he doesn't go back down later on and pick up some other naïve kid."
With that off his chest, Juan asked me to look around and see if the housekeeper had missed anything. I'd arrived with just a small suitcase, so it only took a moment or so to check that my few shirts, jeans, socks and underwear were all there. But some embarrassing purchases I'd made at a sex shop earlier that week were missing; a bottle of lube and some poppers along with two gay mags that featured pix of naked boys in bondage! Noticing my confusion, Juan smiled and pulled open a drawer in the bedside table.
"Looking for these, Benny? The lube and the poppers were no surprise, but those magazines under your socks were a bit of a shock. Thankfully, it was me and not the poor chambermaid who found them. If I'd known you were kinky, we might have had some fun."
Still horny from my fuck session with Tom less than half an hour before, I asked Juan if he wanted to stay and indulge. But he declined, saying he was sorry, but that his co-worker would get suspicious if he stayed away too long. He moved to the door and as he was pulling it open, I repeated my offer, adding that it wouldn't take a minute, since my ass was lubed up and ready to go.
All that earnt me was a grin and a shake of the head. Laughing and calling me a horny slut, he turned away and marched smartly down the hallway. As I closed the door behind him, I noticed that the door across the hallway was slightly ajar, making me wonder if the big guy opposite had heard what we'd said.
I put it out of my mind while I shucked off my clothes and took a quick shower. As I towelled myself dry, I thought about how thirsty I was; not surprising, since I'd had nothing to drink since going to bed twelve hours before. Wanting something more flavourful than tap water from the sink, I remembered the soft drinks machine at the end of the hall.
I didn't bother putting my clothes back on, just wrapped the soggy towel around my waist, opened the door and peeked down the empty corridor. Seeing it was all quiet, I hurried along to pick up a couple of Cokes.
I put the coins in the slot and leant down to pick up the bottle from the tray at the bottom. But when I stood up, I was shocked to find the big guy from across the hall standing behind me, with an empty ice bucket in his hand. I was already embarrassed to be caught wearing just a towel, and he proceeded to make things worse.
"So, first you beg that nosy desk jockey to fuck your faggot ass and now you're parading it down the hallway."
Realising how stupid I'd been, I didn't reply, just pushed past him, and ran back to my room, slamming the door shut, hoping to never see him again.
I plonked myself down on the bed and sucked down one of the Cokes, trying to forget about him and think about the good times with Henry and Tom and fantasize about Juan instead. Since I'd had no chance to cum after Tom had fucked me, I was horny as hell and just as needy, I threw off the towel and took matters into my own hands. But just as I began work on my aching, needy cock, I heard a quiet tap on my door. Since I'd just been obsessing about Juan, I assumed he'd changed his mind and was back, maybe on a break, to take me up on my offer.
I sprang up and pulled open the door, without bothering to wrap the towel around me, only to be faced with Steenburgen, the last person I wanted to see, after the way he'd insulted me. But when I tried to slam the door in his face, he shoved me back into the room and closed the door behind him.
