I was thirty-five, my girlfriend of five years dumped me for some loser that worked at a grocery store, and my job wanted me to take an assignment in the windy and cold Midwest to evaluate some key suppliers. Leaving California for Chicago wasn't my dream scenario, but it was only for three or four months, and right now I felt I could use an adventure and a change of pace. Through a search agency, I found a loft condo that was available for a short-term lease (and one my employer would pay for), and headed for Middle-America. Apparently, the owner of the condo had similar obligations for work, and was willing to rent it out while away instead of paying someone to maintain it. The place was therefore fully furnished. All I had to do was show-up. After trading a few phone calls, and satisfying the owner that I was a professional who wouldn't rob him blind or trash the place, the deal was finally set.
The place was much nicer than the pictures indicated, and I felt like I had really lucked-out. The condo was on the third floor of an old four-story warehouse, and located in a well-maintained area not far from downtown. It couldn't have been more convenient. It didn't take long to realize, however, that being a few blocks from Halstead Street had me in a gay neighborhood. There was still a lot of diversity, a few families, older couples...but the rainbow colors on the lampposts left little doubt about the key demographic. It was cool...I'm not at all homophobic, and I enjoyed the lively vibe of the neighborhood.
I met my only neighbor on the floor, John, when he helped me lug a large box out of the elevator from my countless trips to the basement storage room. He was about forty, a well-spoken professional, obviously very fit, and probably gay. He also had an Irish Setter as a constant companion and completely ineffective guard dog.
"Thanks for the help, man. This should be the last of my stuff...glad I didn't have to bring much more than my clothes."
"No problem. I'm happy Steve found a good match for someone to look over his place. We're not supposed to sub-let, but everybody in the building was willing to look the other way for a temporary thing."
"This is way better than the usual short-stay apartment. I promise not to make you or the other neighbors regret the decision. My name's Glen, by the way." I said, extending my hand to shake his.
"I'm John. Our not-too-helpful assistant is Red."
"I see you spent endless hours choosing a name for you dog." I said with a broad smile.
"Yeah...I'll never get an award for originality." John said with an easy laugh. "He seems to like it, though."
In many ways, Red was the one who made the transition enjoyable. John was an anesthiologist at a local hospital, and would sometimes have odd hours. While John had any number of friends who were willing to check-in on Red, I became a convenient and willing dog-sitter. Red enjoyed jogging with me to the park along Lake Michigan, and was an unparalleled babe-magnet. A few nice dates came out of those trips with Red, but nothing serious, as I made it clear that my time in Chicago was short. John had a variety of friends, both male and female, who would come to his home for dinner or the occasional party. After about six weeks, my neighbor often invited me to join his guests, and I found the camaraderie to be an unexpected surprise. One evening, when his friends had left, and I was helping put dishes away; John's usually casual conversation took a different tone. He'd been drinking a lot of wine, and was a bit uninhibited...but a long way from being truly drunk.
"I think Darla is smitten with you, my friend. Hope you're ready for that wild ride. She's a straight, single gal with a lot of gay friends...one look at your available bod, and she was probably ready to marry you on the spot!"
"Yeah...I got a really heavy vibe from her tonight. I filled her in on my situation. I suggested that a few dates, evenings out, whatever...is about as far as I'm willing to go. I'm not the kind of guy that likes to promise what I can't deliver...or leave trails of broken hearts." I replied with a grin.
"Wow...you've been hanging around my friends too long. That almost sounded like gay drama."
I laughed. "Not sure where I'm learning it. You're just about the most non gay-acting homosexual I've ever met. By the way, thanks for allowing me to buy some of your Cubs season tickets. I've really enjoyed going to the games."
"My pleasure...the day-time games aren't always convenient for me. I'm glad you're schedule is flexible enough to use them. You should hit the clubs downtown tonight. I'm sure that buff, blond, grown-up surfer look of yours could land a few ladies who wouldn't mind a short fling."
"Yeah...well...I'm sure I could find some company if I put my mind to it. Thing is, I had a long-time relationship that ended badly. I'm kind of enjoying this side-trip, and trying to take things easy. I can worry about the ladies when I'm back in California."
"As usual, sounds like you're being completely rational. I like looking at you. It seems a shame to deny the women of Chicago the same dose of eye-candy." John looked immediately uncomfortable as he took another drink of wine. "I just said that out-loud, didn't I? I'm sorry...that was uncalled for...I feel like a complete ass."
"It's ok, man. I know I'm not the ugliest guy on the planet." I said, trying not to sound like a conceited jerk. "You're not the first guy to give me a compliment, and I've learned to accept it as just that. Maybe you're the one who should hit the clubs tonight."
"Yeah, well...perhaps like you, I'm taking a break from the hard work of finding a solid relationship. My career isn't exactly conducive to paying attention to the needy-type guys I seem to attract. Besides, I'm just not a bar-fly kind of guy."
"Well, I'm sure we'll both be able to find a way to entertain ourselves when we want to." I answered, putting away the last plate and rubbing Red behind his ears.
"I could entertain you...with no strings at all...if you'd ever want to." John said dryly, drinking more wine and mindlessly brushing his hand over his crotch. "I wouldn't require anything from you."
I paused for a moment...a little stunned at being so bluntly hit-on by another dude. Oh, it had happened a time or two when I was younger...but usually involved a nervous greeting that I would quickly, but politely decline. After the initial shock wore-off, I smiled and reached for John's wine glass. "I think maybe somebody's had a bit more than normal and is saying things they might regret later."
"I know you're a straight-arrow." John said, sounding more inebriated than I originally thought. "But if there was a contest for who could rip your clothes off...I'd be kicking Darla's ass right now." He said, with his hand nervously cupping my crotch.
I gently pushed his hand away. "Uh-huh...I'm sure you'd triumph. I'll let you rip your own clothes off and get to bed. I'll see you and Red in the morning. You're welcome to join in our run, if you're off work tomorrow."
John's face was deeply flushed, and a look of deep regret was once again obvious. "Thanks, Glen. You're way too kind. I'm just...just a fucking dumbass."
++++++++++++++++++++
I knew John well enough, that he would be kicking himself the next morning, and I did everything I could to act as though nothing happened. I made no changes to the arrangements for days I watched Red, invited him out to dinner from time-to-time, and tried to make him feel like it was water under the bridge. It took about a week, but he eventually relaxed and stopped apologizing every time our paths crossed.
To be honest, his actions had unexpected consequences for me. The next few nights, I had dreams of John in various sexual scenarios. Mostly they were laughable, and easily dismissed...but a few left me with serious morning wood that had me imagining his grip on my shaft while I jerked-off in my landlord's oversized shower. I had never really imagined sex with other men before...at least on purpose...and it unnerved me. I realized, however, it was the result of John's advances...and a phase that would soon pass.
Another week had passed, and I was awakened at 7:00am on a Saturday with repeated knocking at the front door. I stumbled out of bed, wearing a t-shirt and boxers, and opened the door in a half-awake daze. John was standing in the hall, shirtless, and wearing only a pair of hospital scrub pants.
"I'm sorry to wake you up, man. I was going to slip to the box for the morning paper...Red managed to close the door and locked me out. I need your key."
"Oh...uh...yeah...come in." I mumbled, scratching my head as I turned to find the key John gave me when I took Red for walks. For a brief moment, it occurred to me that my neighbor was much better built than I thought. I wondered when he found time to work out. "Here it is...sorry...I haven't had my morning coffee yet."
I returned to find John standing just inside the door, with an obvious bulge at the front of his scrubs. He moved one arm down in an attempt to hide it while reaching for the key with the other. "Thanks...again...really sorry to bother you...especially on a Saturday morning." He stammered, while seemingly looking me over from head to toe.
I glanced quickly at the mirror across the hall, noticing my dick was peeking out from the fly of my boxers. I had been so groggy, and focused on finding the key, that I hadn't noticed. Embarrassed, I turned away from John, adjusted myself, and went to the kitchen to make coffee. "Feel free to stay for coffee. I'm going to grab a shower and try to look more human." I offered, knowing he probably wouldn't stay. The offer was also an attempt to avoid apologizing for exposing myself.
