Short-Term in Chicago

"That may be the understatement of the century. I like you man, but I wasn't looking to pick up a gay lover in the windy city. What bugs me most is my own behavior...I should have stopped you. For whatever reason, I was just paralyzed. I don't know if it was shock, bewilderment...I just don't know why I let it happen."

John just smiled and drank his coffee. "Trust me, I wasn't looking to lure you into my world of debauchery and turn you into a gay sex slave. I'm just really into you, and thought I could show you something new. Part of my twisted psyche loves going after straight guys. It's probably some perverse association with the time in my life when I tried to convince myself I was straight."

"You're not on some crusade to convert the hetero world, are you?"

"Hell no...there were a few ladies that I truly loved. But, in the end, I knew I was lying to them and to myself. I think men in general are too uptight about sexuality. Most have no problem with two women going at it in some sleazy porn video...but think their skin would ignite if they touched another dick. There's a difference between sex and love-making. I just think there's room for both."

"Interesting philosophy...and I suppose it would make sense to a lot of people. At least I can report that my skin hasn't erupted in boils from self-loathing. I'm not such an uptight prude that I won't survive the experience."

"Good...I guess I'm happy I didn't make you suicidal." John said, before refilling our coffee and sitting in the chair across from me. "So...was it good?"

"Uh...what?" I answered, nearly choking on my coffee.

"Aside from the mental turmoil afterwards...did you like it...did I make you feel good?"

"Nothing like a direct question."

"You might have noticed that I can tend to get right to the point. Do you have a direct answer?"

"Honestly, yes...I would have to say I never had a blowjob that good...ever."

"Cool...I think there is a lot of truth in the notion that owning the equipment provides insight that the opposite sex could never know." John said coolly, sitting back in his chair with his legs splayed apart and staring at me intently.

"Um...yes...that would seem reasonable." I answered softly, sensing a change in atmosphere.

I looked back toward John, his left hand placed lazily over his crotch and his right undoing the buttons of his shirt...his gaze never moving away from me.

"What are you doing, dude?"

"Getting comfortable...I like to do that in the evenings."

John pulled his shirt open, revealing a nicely toned upper body covered in neatly-trimmed dark brown hair. I had seen this much of him at the door this morning, but paid little attention. I had no doubt most women, and apparently men, would find him attractive. Watching him produced a slight stirring in my groin, and I was wishing I hadn't worn such tight jeans. It seemed like it was time to go.

"Well, I thank you for dinner, and will give you time to relax and enjoy what's left of your weekend." I said, intending to get up, but not quite making it happen.

"Sure...but you're welcome to hang around a while longer. It's safe to say that I enjoy your company...for however long you're willing to share it with me." John said, running his hand over his chest and squeezing his crotch with the other.

I sat speechless for a few moments, not believing he was trying this again with me. "I'm flattered...but it would seem you need a private moment." I still hadn't fucking moved.

"Have you ever touched another man's dick before?" John asked, staring at my shock-stricken face. "Yes...I know...another direct question."

"Uh...no...no I haven't"

"Really...not even a junior-high circle jerk?"

"No...can't say the occasion ever came up." My throat was getting tight, my cock swelling a little more, and I still couldn't seem to get out of my chair.

"Would you like to? You might be surprised how different it is than feeling your own. I'd be honored to share that with you." John said, rising from his chair and standing a few feet in front of me...his khakis stretched with an obvious tent pole. "I understand if you're not interested, and would rather call it a night. You're just too damn hot to look at and talk to. I can't help but get turned on by you right now."

My face flushed a bright red at the thought of being quite that appealing to another guy. At last, I found the momentum to stand up from the chair. "Good night, John. A cold shower might do some good." I replied with a shake in my voice.

I was ready to leave when John gripped my wrist and shoved my hand into his pants. My fingers brushed past his pubic hairs and rested against the warm, silky flesh of his cock. I made a half-hearted effort to pull away, but John held my arm firmly.

"Grip it, Glen...take a hold of it. That's raw desire, Glen...pure sexual lust...and directed toward you. I want to share a physically intense, good time with you, my friend. That's a lot of trust between two men."

"Man...this...this is fucking weird." I stammered, with my hand still resting limply inside his boxers.

"Then teach me a lesson." John said, pushing my hand further down his pants. "Squeeze me by the balls and leave me here alone to accept my punishment. Or you could broaden your horizons...fondle my balls...feel how heavy they are...how soft my sack is."

"Man...I've got no interest in hurting you..." I started to say, before John cut me off.

"Good...then let's spend the next hour or so not hurting each other. Feel my cock, Glen...I really want you to feel another cock. I'm so fucking hard for you."

My heart was pounding so hard, I could hear it. John kept his eyes locked on mine as I slowly relented, wrapping my fingers around his pulsing rod. Why the fuck was I doing this? It did feel remarkably different. The heat emanating from the blood-engorged pole was scalding, the skin was soft and silky, while the flesh beneath was rigid and unyielding. I knew my own prick had to be similar, but it never felt quite like this when stroking my own morning wood.

"Oh, yes...fuck, yes...that feels so damn good." John moaned, as I slowly stroked my first foreign cock. He allowed only a few minutes of my feeble manipulation before stepping back and taking off his shirt. "Undress for me Glenn. Show me you're willing to explore further without me pushing you. I want you to enjoy yourself...not hate both of us later."

I stood there, dumbstruck, the paralysis flooding over me again as I watched John kick off his shoes.

"I know you're nervous...you have every reason to be...this can stop any time." John said calmly and reassuringly. "Take off your shirt, Glen...let me see that ripped torso of yours."

"Uh...shit, dude...this...well it just isn't me."

"That's cool. But I think you might be a little curious. Nobody's keeping you from the door. You might miss-out on some mind blowing shit. It's not like I'm going to tell anybody. Your secret will go to my grave."

I hesitated, my breathing becoming ragged as I moved my arms a little at a time before finally grabbing my t-shirt and pulling it over my head. This was it...I had done it...I made the move to take this further. I felt like I was fifteen again, nervous as hell, like I was getting laid for the first time.

"Nice...really, really nice...you have a terrific body. Now lose the shoes."

Again, I silently and nervously did as instructed.

"Look at me Glen."

I stared straight into his eyes.

"Let's do this part together...when I unzip, you do the same. When I lose my pants, you lose yours. But keep your eyes on me when you're doing it."

It seemed simple enough. I watched with new appreciation as John lowered his zipper, allowing the khakis to fall off his trim waist and well-developed legs. I was looking at another man very differently for the first time. He was attractive...he had the physique I thought a healthy man should have...and his boxers were tented with the only other erect cock I had ever seen in person. I never had a problem acknowledging another guy as good-looking. I surprised myself by seeing John in a sexual context...and being intrigued by it. I could hardly believe I was standing in my briefs with a raging hard-on in front of another man.

John stepped closer toward me, his cock bouncing within the confines of his boxers. He ran the back of his hands over my chest, pinched my nipples, and lightly brushed over the bulge in my jockeys. "Nice isn't it...to just be with another person...to share what you know feels good with someone you can trust."

"Um...yeah...I...I suppose so." I said; my throat still tight with nerves.

"Do you trust me, John? Do you know that you can say "no" at any time?"

"Yes...I trust you'll honor my limits." I answered, timidly running my hands over John's pecs and biceps.

John gave no response; he just started running his tongue over my chest like he had done earlier this morning. My stomach trembled with butterflies as he licked past my navel, and gently chewed at my hard cock through the cotton fabric.

"Oh fuck...oh fuck..." I mumbled over and over as John teased my prick, running a finger inside the leg opening and under my balls. I expected him to start sucking me again, but instead worked his way slowly back up my body.

Standing in front of me, John placed his hands on my shoulders and gently urged me toward the floor. I clumsily knelt in front of him, unsure of my resolve.

"Take them off, Glen. Pull my shorts down and take a good look at what your girlfriends have been faced with...figuratively speaking."

I paused, knowing I was going to do this, but hardly believing it. I gripped the waistband of his boxers, tugging them over his muscled ass and off his legs. John's cock smacked my face, covering my chin in pre-cum as it sprang from the fabric prison. From this perspective, it seemed huge...though barely longer, but just as thick as my admittedly above-average tool. His sack hung low, was shaved smooth, and held two egg-sized orbs. I keep things trimmed, but never wanted to get a blade near the family jewels.

"Go ahead...touch it...feel my balls...do whatever you want." John urged, bobbing his cock in front of my face.

A taboo sense of discovery came over me as I placed one hand around John's ample prick and felt the soft skin of his scrotum with the other. In the back of my mind, I thought there was no way in hell I should be doing this...but I was now overcome with the sensations of my illicit groping.

"Oh yeah, man...that feels good. Put your tongue on it. Think of the women who enjoyed doing this for you...it will be no different for you, than it was for them."

I certainly couldn't argue with the logic, but now I had some hesitation as to how far I could go. I stared at the end of John's leaking cock...a ribbon of clear fluid trailing toward the floor. My own cock was painfully hard, and I wished the roles were reversed. I took a deep breath, closed my eyes, and tentatively placed my tongue on the spongy helmet. The taste was a little salty, but not near as bad as I feared. John moaned in appreciation, gently thrusting his hips and urging me to take more.

"Oh fuck, man...that's it...do what you know would feel good or you. Come on, man...suck my big dick!"

John put his thumb in my mouth, forcing my lower jaw down, and pushed the head of his cock in my mouth. I wasn't expecting that, and started to cough and choke on the new intruder.

"Just relax...let it sit there...get used to it...coat it in lots of spit." John said, holding my head in place with on hand in my hair. "It gets better...your girlfriends went through the same thing."

John wasn't really forcing me to do this, but he wasn't going to let me retreat without trying either. I followed his suggestions, and found that my gag reflex quickly subsided, and the ample spit made things more comfortable. John let go of my hair, allowing me take as much of him as I felt I could handle, and at the pace best for me. I got four, maybe five inches of his hot man-meat in my mouth, but could do no more. I had newfound respect for the women who could take me down to the root.

"Oh shit...that's good, man...awesome for your first time. Yeah, that's it...right there. See...you know exactly what you're doing." John groaned as I relaxed and began running my tongue around his cock.

I felt oddly proud to be making him feel that good. I could feel my inhibitions slowly fading as I worked into a steady rhythm, eventually allowing John to gently face-fuck me...his heavy balls swaying with every thrust.

"Lick my balls, man...put your tongue on those nuts." John said, pulling out of my mouth and pressing my face into his crotch.

The feeling was both strange and incredible as I gently suckled the hanging fruit and the soft folds of his sack draped over my nose. I could hardly believe how comfortable I was getting with this as the minutes passed by. I was ready to tackle more of John's cock, when he abruptly lifted me to my feet and held my face firmly in his hands.

"Shit...you are fucking hot!" John said, looking me in the eye. "Tell me...say what you want...talk dirty to me, man."

Damn, I was horned...I was ready to do most anything just to get off. "On your knees, cocksucker...take my dick straight down your throat." I replied, in a gruff tone.

"Fuckin' A." John grunted, beating my chest with a loose fist like some sex-crazed primate. He then pushed me back onto the chair, knelt between my legs, and pulled my ass to the edge of the cushion. Grabbing my briefs, he roughly tugged them down my legs and tossed them across the room.

"Uuunnggg...aahh ssshhhiiiitttt!" I groaned as John ran his tongue along my inner thigh, over my balls, and along the bottom of my steel-hard cock.

John's touch was rough and masculine...so completely different than the soft strokes I experienced with so many women. He devoured my cock as though he starved for it. Sensing my heightened arousal, he brought me to the edge and back again...over and over...knowing exactly how to prolong the sexual tease.

"Damn...you're one hot fucker." John mumbled while licking my balls. "This should blow your fucking mind."

Before I knew what was happening, John thrust my legs into the air and buried his tongue into the crack of my ass.

"Oh god...fuck...oh fuck..!" I shouted as the new sensation shot through my body like bolts of lightening. No one had ever been anywhere near my ass, and the feel of his tongue around my sensitive pucker was explosive. While I was lost in the new feeling, my mind also flashed with mild panic over what else John had in mind.

"Shit...oh god...that's fucking intense." I panted, pushing John's head back. "I'm not crossing that line, man...busting my cherry isn't happening."

John just smiled and stood up between my legs...his cock throbbing and dripping pre-cum. "Don't worry, bud...wasn't my plan...that's some very advanced shit. But I may slip you a small surprise later. Trust me, you'll love it."

"Thanks...I...I almost panicked." I answered, still trying to catch my breath.

"Let's get you out of that uncomfortable chair. I'll be in the bedroom if you're ready for more."

I couldn't say John wasn't giving me plenty of opportunities to chicken-out, and I weighed the options as I watched his naked form walk toward the bedroom. I sat there for a few moments, my cock slick and shiny from John's spit, and my sphincter still twitching from the unexpected stimulation. "Who's going to know?" I asked myself. "Even if it goes badly...I won't be any worse for wear because of it." I rationalized in my own mind, trying to make the whole thing acceptable to my conscience. "Fuck it...I need to get off."

I walked cautiously to the bedroom, my inner-voice repeating that I didn't need to do this...pussy wasn't that hard to get. The other side of my brain however, craved the taboo nature of the whole thing. Messing with a dude seemed dangerous, over-the-top, and exciting. I found John lying on the bed, his head hanging off the edge of the mattress, stroking his impressive tool.

"Afraid you might have left. Feed it to me, straight man...give me that breeder cock." John said, allowing his head to tilt down further and opening his mouth wide.

Shit...I'd gone this far...if he was willing to blow me off again, I was willing to let him. Bending my knees for a better angle, I aligned my swollen pole with his mouth and slid fully inside. My cock was already soaked with spit and went easily down his throat. John hummed with contentment, vibrating my prick as I worked into a rhythm. I tried to keep a standing position, but the angle was too hard to maintain. I eventually bent over, my arms stretched out to support my upper body with my hands pressed to the mattress at each side of John's waist. I could feel my sack drag across John's forehead with every push into his wet mouth. It was impossible to ignore the body below me, the cock jutting up in the air, the muscled frame writhing on the mattress. I could see the loose sack pooled between John's legs and the copious amount of pre-cum oozing down his shaft. Damn, he was doing incredible work on my cock...it only seemed fair to do the same. I stared at the swollen man-meat for several seconds before deciding to take my second taste. The heat filled my mouth and radiated through my cheeks as I worked more of him into my mouth. My jaw stretched wide to accept his girth, but at least this time I wasn't gagging.

John ran his hands across my back and over my ass, slapping my buns to encourage a faster pace. His body shifted slightly, allowing him to lift his head and rim my ass. The same shock-wave coursed through me again. I couldn't believe that act could possibly feel so good. I was still sucking his cock, when John pressed a moist finger inside my ass and probed for my prostate. The intrusion made me gasp for air...my arms went weak, and my body fell onto his. John's hard cock pressed against my chest as he bent my cock downward to suck on it, while still fingering my virgin ass. I could only grunt and moan through the overwhelming sensation.

"I said you'd love this surprise." John said, relentlessly bringing me near the brink and back down again. I needed to unload so badly that my balls were aching.

"Better calm you down before you explode." John said, flipping me aside so that I was lying on my back. John then spun around and stretched his body on top of mine...our cocks pressed together between us as he held my arms over my head. I wriggled my hips, rubbing my aching member against his body, hoping for a much needed release.

"This might be the most difficult part for you, Glen...but I promise it will be ok." John said, before pressing his lips to mine and shoving his tongue deep into my mouth.

I resisted immediately...as though kissing him was far more caustic than sucking his dick. In retrospect, it made no sense. I can only imagine that it added an element of intimacy that I held separate from just fucking. The stubble on his chin rustled against my own as he insistently bit at my lip and sucked on my tongue. This was no romantic kiss...it was powerful, and I soon understood the meaning. This lip-lock wasn't conveying love and tenderness. It was about sharing raw energy, sealing the bond of trust that nothing would leave this room. After the initial shock wore off, I began to return the gesture in just as rough and powerful way. John released my arms and I gripped his hair tightly, pressing my mouth to his firmly...running my tongue along his chin and neck.

"Yeah...fuck, yeah." John grunted, pulling away and straddling my waist. He kneaded my pecs and shoved a pillow under my head. "Suck on it, man." John snorted, pointing his cock at my mouth.

I no longer hesitated...I was more than will to give him what he wanted...knowing it was just between us. I was able to take much more this time, and while still very much an amateur, managed to reach the base of his cock. John pistoned into my mouth slowly, as his heavy balls glided over my chest. I could feel his body twist to the side and hear a drawer open in the nearby nightstand. I heard the snap of a flip-top bottle, and then felt John spread a silky liquid over my straining cock.