Short-Term in Chicago

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.

"I may do that...and return the key before I forget it."

I shook the cobwebs from my head and walked to the shower as I heard the front door close. The water felt great, and I spent more time than normal enjoying just standing under the shower, not feeling the weekday rush to get to work. I dried off, wrapping the towel around my waist and walked toward the kitchen. I didn't feel comfortable sleeping in Steve's bed...so I slept in the guest room, but couldn't resist using the larger master bathroom. The daily walk from one side of the condo to the other was inconvenient, but the multi-head shower was worth it.

"Wow...you stay toned like that just running around the lake shore?" John asked, sitting at the kitchen island, now wearing a t-shirt and the same scrub pants.

I hadn't noticed him sitting there, and was startled...dropping my towel, exposing myself once again. "Oh fuck...you scared the shit out of me!" I said, quickly returning the damp towel to my waist.

"The way you came breezing in here, I suspected you hadn't seen me. I should have coughed or made some other noise." John said, stepping around the island to face me while filling his coffee cup. "But it made my morning worthwhile, anyway."

I couldn't help but notice the outline of his manhood through the thin fabric of the scrubs...and it seemed to be growing. To my surprise, I could feel my own cock twitch in response to seeing that, combined with John's leering stare over my body. I was now very uncomfortable...only wearing a towel so close to a dude who wanted to see me nude. "Uh...help yourself...I'll get dressed...be back in a minute."

"Relax...there's no hurry on my account. You seem tense. Get your nut off this morning? Maybe that would help." John said in a low tone, the tent in his pants now obvious, and a circle of moisture forming at the tip.

"Fucking hilarious, man...but not something I'm into." I said nervously...uncomfortable with his closeness, and the unexpected tingling in my groin.

"You're not into feeling good...blowing off a little steam now and then?" John was now openly squeezing the engorged flesh within his pants.

"You know what I mean...there's no need to spell it out for you." I wanted to move, but seemed frozen in place.

John stepped even closer. "Straight guys...you never know what your missing. I'm willing to show you...no strings, no anxiety of knocking someone up...just fun."

"I...oh...shit..." my words of protest were cut-off as John's hand reach behind the towel and gripped my half-hard member.

"You haven't run away...you haven't taken a swing at me...so just take a deep breath and go with it. I promise it won't turn you gay." He said with a soft chuckle.

I was wondering why I hadn't done either of the things he mentioned. I still hadn't moved as John slowly stroked my swelling tool, running his other hand over my chest, pecs, and abs. The towel fell to the floor again, and the coolness of the granite countertop touched my ass as John guided me against the cabinets.

"Nice cock, straight boy. I'm sure you've plowed plenty of pussy with this prime beef." John said gruffly before send a trail of spit down to my tool and spreading it within his grip.

I was a little surprised at salty and direct way John was speaking. It seemed somehow out of character with his normally professional and conservative demeanor. For reasons I still didn't understand, I also found it arousing. The direct, no bullshit approach to sex was so completely different than the gentle, romantic method my girlfriends preferred. The raw, animal energy was becoming intoxicating. My mind was still telling me this was wrong...it needed to stop. My body, however, seemed to be willing to indulge the intense taboo sensations.

My breathing was ragged as John bent down to lick and suck my nipples...his hand kneading my pecs. Slowly, his tongue ran down my chest, over my shaft, and teased the tip of my prick. Kneeling on the floor, John licked the precum from my piss slit, and eased the head of my cock into his mouth. Damn...I had never felt a tongue dance across my cock with such knowing skill. He knew exactly where to go, what to do, and for how long. No woman ever compared to what this man was doing to me. With his jaws stretched wide, John methodically worked all of my thick, seven inches into his throat, his nose buried in my dark blond curls. Holy shit...this felt fucking incredible!

"Mmmm...yeah...that's a hot fucking cock!" John groaned, pulling off my prick and slapping his face with it. "Fuck my face, man...bust your nut down my fucking throat!"

By now, I was simply crazed. My cock was painfully hard, and I had no problem fulfilling my neighbor's request. John opened wide as I took aim and slid into his mouth with one fluid stroke. I gripped his hair and held his head still as I thrust with a steady rhythm, my balls slapping against his chin. This was the first time I had looked down to see my cock disappearing into another man's mouth. I felt I should have been repulsed...but John's tremendous skill convinced me otherwise.

"Yeah...oh fuck yeah...eat it man...take all that meat!" I exclaimed, finally finding my voice and relinquishing my inhibitions. Not feeling bound to be tender and loving, I drove into John's face with only one goal...to get off. This was wild, intense, and guttural. My balls began to tighten, and I knew my release was imminent.

"Fuck...ssshhiiiiitttttt...dddaaammmnnnnn!" I grunted loudly as four streams of cum shot from my prick and filled John's waiting mouth.

John never backed off. He reached back, gripped my ass, and pulled me tightly against his face. His tongue expertly milked my pulsing pole as the overflow of seed seeped from his lips and ran down my balls. I was still gasping for air when John released my twitching prick, rose from the floor, and dropped his pants. His hard cock jutted straight out as he spat my cum into his hand, gripped both our rods, and jerked them together with my spunk as lube. John's impressive tool was an inch longer than mine, and just as wide. The heat of his flesh against my still-sensitive prick was intense. I watched in amazement as John's eyes closed, his jerking motion quickened, and his cock unloaded into my pubic bush. John grunted like rutting animal, his creamy spunk splashing against my abs, running down my inner-thigh and over my balls.

After our cocks began to deflate, and our breathing returned to normal, John pulled the scrubs back over his waist and took a swig of coffee. "Shit...thanks man...I needed that. Take some time...think it through...if I haven't freaked you out too much; come over for dinner tonight at seven. We'll either eat, or you can kick my ass." He then calmly walked out the door.

My mind was a complete blur. I struggled to recover from what had been one of the more intense sexual moments of my life. John's cum was matting my pubic hair and clinging to my balls, and the only thought I has was that I needed another shower. A few hours later, the full realization of what happened hit me. I had been seduced by a dude, and like some paralyzed zombie, I let it play through. I was horny, sure...but not out-of-my-mind horned. Hell, I got laid four days ago by a smoking-hot redhead with incredible tits. I don't mind saying John is good looking...for a guy...but he isn't my idea of a fantasy fuck. I'm not insecure about who I am sexually; I just honestly never thought that man-sex would ever interest me. Part of me expected to struggle with this and go on some dumbass drinking binge. Oddly, though, I wasn't feeling at all self-abusive or suffering much mental anguish. I was upset at not being more upset.

After it was clear that I wasn't going to be pissed with myself, I tried to focus on being pissed with John. I had every reason to resent being manipulated like that, but I couldn't hold onto any real resentment toward him either. My mind kept drifting to the fact that he had given me the best blowjob of my life, and I didn't have to call the next day, send flowers, or go to lunch with his mother. Shit...my cock had started twitching again.

The rest of the day stretched on forever as I debated the dinner invitation. If I stayed away, it would say that I was pissed-off and could make the remainder of my time in Chicago uncomfortably tense. If I went, it may signal an interest in doing more, which might also make things uncomfortably tense. As seven o'clock approached, I decided to grow-up, enjoy dinner, and discuss the situation like two adults.

When John opened the door, he stood there with that familiar look of regret in his eyes. "Feel free to punch me repeatedly, if you'd like."

"I would have been over before now, if that was the plan. You gave me an afternoon of tortured thoughts, but I think we can discuss this like grown-ups. I'll save the "Jerry Springer Moment" for later."

"That's a gentleman's answer, and more than I deserve. Dinner is nearly ready. I think you're obligated to giving Red a belly-rub. He's been out-of-joint over missing his long run around the park. Oh, and Steve called...I gave you glowing reviews, so you're in no danger of being kicked to the curb."

"Well, thanks...I can't blame him for checking on me, especially since we've never met face-to-face. Are you and he good buds?"

"No...we're just friendly neighbors that mainly stay out of each other's way. He's a nice guy; divorced, early fifties, has a grown daughter that visits on occasion. Steve's not around much...not sure why he bothers to own a home."

"I guess he has his reasons. It's a damn nice place."

Dinner was pleasant, we shared some mindless chit-chat, but the elephant in the room was obvious. I kept trying to find a way of clearing the air, but the words just wouldn't come to me. When dinner was finished, and we were drinking coffee in the living room, John decided to break the ice.

"Look, I'm sorry about how this morning went down. I was horned out of my mind, the chance to see you with a little less clothing was too tempting...I let things get out of hand."