A gay story: Short-Term in Chicago Ch. 02 ++++++++++++++++++++++++
Please read part 1 to have a better understanding of what’s going on. Before I get a dozen emails telling me how irresponsible I am for not including condoms…you’re right. My only defense is that this is written as a fantasy, not an instruction manual. Get tested often, and play as safely as possible at all times.
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I truly appreciated John’s efforts to give me a farewell party upon the completion of my work in the Windy City. Many of his friends had become my friends, and the company of so many professional, intelligent people made my stay more pleasant than I imagined. The guests had departed, and I was sitting in John’s living room, sipping coffee and rubbing Red’s ears while I watched him gather the remaining dishes. It occurred to me the irish setter that had it’s head in my lap might be the one soul I would miss the most. I briefly thought about getting a dog when I returned to California, but I knew my lifestyle wouldn’t be fair to the animal.
“Is there anything I can help you with? You’ve worked hard enough on dinner as it is.” I asked, noticing more dirty wine glasses in the living room.
“Of course not…the major stuff is done anyway. All that’s left is a few glasses here-and-there. Besides, I think your jogging buddy is shamelessly taking as much time with you as he can get.” John said, looking at his dog which had draped itself over my lap.
“He’s been a lot of company. Seems like an extended rub behind the ears is the least I can do for someone who helped me get so many dates.”
“If I could just get his charms to work its magic on more of the boys, then I’d be a happy man.” John said, with a broad smile.
“I’ll admit that I don’t have much of a sense for gay relationships, but it seems like Ben is more than a little interested. He seems pretty focused on you most of the time.”
“Yeah, well…we had a “thing” about a year back. We’re still good friends, but I know I don’t want to go down that road with him again. Let’s just say he has more baggage than I can handle, and leave it at that.” John said with a cool seriousness.
“Ooh…sorry…didn’t mean to intrude or pour salt on any wounds. In an effort to change the subject, is your offer to help me pack still good? I don’t have much, but would like to leave Steve’s place looking like no one had been there.”
“Absolutely…but trust me, Steve wouldn’t notice if you left a week’s worth of dishes in the sink. He has a maid that comes in a few times a week.”
“Wow…how did I manage to leave that out of my lease agreement?” I said with a chuckle, moving Red off my lap and getting up to put my cup in the dishwasher.
I helped with the last few items, offered my gratitude for a very pleasant evening, and went across the hall to my rented condo. The next morning’s packing job wouldn’t be difficult, but I knew that John could help me make sure everything was where it should be. Damn, I was going to miss that huge shower.
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I got up early the next day and started packing, leaving only enough items to get me through the next two days. At around ten o’clock, I heard the doorbell, and knew it would be John coming over to help. I opened the door to find him wearing a well-worn set of hospital scrubs.
“Are you expecting to perform impromptu surgery?” I asked, sarcastically.
“No, smartass…just didn’t want to put on a suit to help pack your shit.” John replied, punching my arm as he stepped through the doorway.
“Hey, whatever…but I promise I left all the greasy car parts in California.”
We worked the next few hours, getting things in boxes for the shipping company, shooting the shit, and basically just getting things done. Around noon, we had a local sandwich place deliver some lunch, and went over to John’s place to avoid making a mess. When he took a seat on one of the counter stools, I noticed the outline of his junk as it came to rest down his left pant leg. “Huh…he’s going commando”, I thought to myself before quickly moving my gaze in another direction. At that moment, my mind flashed with images of the unexpected experimentation I shared with John. In retrospect, the whole thing seemed almost surreal. As I shook the thoughts from my head, and focused on lunch, I realized that I had to respect John for keeping his promise. Not since the last encounter, had he made anything resembling a sexual advance.
“Hey man, where’s your head? You seem to be deep in thought.” John asked, bringing my thoughts back to the present.
“Oh…just thinking about all the shit I’ll have to take care of when I get back home. This three-month field trip has been interesting, but aspects of it have been a pain in the ass.”
“I can understand. I know everyone at the dinner last night will miss you. Any chance you’ll be back around?”
“I’m not sure. It’s likely I’ll make a follow-up visit with this vendor…but it may only be a once-a-year thing.”
“Well…don’t forget us when you’re back in town.” John said, finishing his sandwich and tossing the wrapper in the trash. “Let’s get those boxes downstairs to the storage closet, and we can relax the rest of the night. Maybe you can even squeeze-in one more date with one of the ladies you’re leaving behind.”
“I had three dates that went beyond a nice evening out. You make it sound like I’m leaving behind a trail of broken hearts. I’ve said my goodbyes on very good terms. It’s best not to muddy the waters at the last minute and risk leaving the wrong impression.”
“I know…I know…just didn’t want you to be bored, looking at an empty closet.” John said with an easy laugh.
We made a few trips in the elevator, moving my stuff to the storage closet where the shipping company could find them. John and I had both started to sweat, and I could see the back of his shirt clinging to his shoulders and down the center of his back. The thin fabric of the old scrubs was nearly translucent with sweat, and the muscles of his back were visible with every move. Once again my thoughts drifted to previous events…a mix of disbelief that I had ever done anything like that, and realization that I would likely never repeat it. My first foray into taboo sex was spurred by repressed curiosity, and the knowledge that the whole situation was temporary. I would go back home, and never face a scenario like that again.
After all the boxes were stored, and we rode the elevator back upstairs, I found myself staring at John as he leaned against the metal wall. He was attractive, physically fit, professional and intelligent…but still just a guy. John was not at all what I naively thought a gay guy would be like. He could talk about sports, was not unwilling to discuss his early attempts at going straight, and admitted that pussy wasn’t all that bad. He had no deep love of show tunes, or rainbow-colored décor. If I was meeting him again for the first time, I’d have no clue to his alternative lifestyle. John had become someone I trusted and enjoyed spending time with…a true friend. The elevator stopped, and we returned to John’s condo for a cold beer. Over the last few hours, there was something I wanted to tell him, even though I knew it didn’t need to be said. I was starting to have a sense of loss with my departure only a day away, and knew that I would miss his friendship.
“Man…I want to thank you. You’ve made this detour easier than it could have been, and I’m grateful for that.” I said, feeling slightly nervous, but not knowing why. “I…uh…shit…it’s just…I wanted you to know that I really am cool with what happened a few weeks ago. We never really talked about it afterwards…and I struggled with it a little…but…well…it is what it is, and I just wanted to make sure you weren’t still having a guilt-trip over it.”
John smiled, took a long drink from his beer, and paused a moment before replying. “Thanks, Glen…I do still feel like an ass, but I appreciate you letting me off the hook. I’m glad you found a way to put it in perspective and move on.”
“You kept you word…and that made it easier. You could have told a scandalous story to your friends…but you kept your mouth shut. I guess you could say that saved my opinion of you.” I said with a nervous chuckle.
There was a tense pause in the room. As though both of us wanted to say more, but didn’t know how. The tension was broken when John’s cell phone started ringing. Apparently, he was on call this weekend for the hospital.
“Sorry Glen…I have to go do my thing. It’s just an appendix…hasn’t burst yet, so I should be back in three or four hours.” John said, mindlessly taking his shirt off and tossing it in the laundry room.
“No problem…in fact, gives me a good excuse to take Red out for a jog. Text me when you’re done, and I’ll get some Chinese take-out for dinner. I’m not anxious to dirty anything in the kitchen.”
“Sounds good…catch ‘ya later, man.” John replied, walking to his bedroom and closing the door.
I went back across the hall, took a shower, and got ready to take Red out for his walk. When I returned to John’s condo, he was already gone, but his furry companion was eager to see me with the collar in my hand. The walk in the park was interrupted by the usual number of attractive women willing to make small-talk while rubbing Red’s ears, but my thoughts were elsewhere. I kept thinking about the experience with John, wondering if it had changed me in anyway. The answer seemed to be “no”…that kind of activity had never been part of my life before, and I couldn’t see it fitting in with my friends or lifestyle in California. In truth, it seemed to be a special event, focused on one individual, in a unique situation. Yet, I couldn’t help but think that I wanted it one last time. The thought of repeating, what to me was such a raunchy and taboo thing, caused a stirring in my groin. This would be the end of it…a life experience I could check off my list…but with someone I trusted as a friend.
About an hour later than expected, John sent me a text saying he was on his way home. I ordered the food, and was pulling out plates when he came in the door. By now, I had turned into a nervous wreck. For the past several hours, I argued with myself about what I really wanted. The idea of trying to get sex out of another dude was simultaneously intriguing and repulsing. I had no idea how to approach the subject, or if my resolve was strong enough to actually do it. By the time dinner arrived, I had convinced myself that this was just a phase that needed to end. My conviction started to erode, however, after an hour of bullshitting about baseball, work, and cars.
“Is there something bugging you, Glen? You seem…I don’t know….a little distracted.” John asked, as he grabbed two more beers and sat next to me on the sofa. “This is my fault, isn’t it? What I did to you really messed with your head.”
“No…please stop beating yourself up over that. I’m honestly cool with it.” I answered calmly, even though my throat began to tighten. This was my last opportunity to step over a line I never imagined I’d cross. “You know…I should be honest…if it weren’t for the knowledge that I was leaving soon and unlikely to return, I wouldn’t have let you do it.”
“Well…again, I’m sorry…and now that I think about it, it was probably the same for me. I confessed my “thing” for straight guys…and I allowed myself to go too far, knowing you wouldn’t be here forever.” John leaned back on the couch with a heavy sigh and closed his eyes. “I’d say that definitely makes me a fucked-up predatory jerk”
“We’re grown-ups, man. If I felt that way about it, I wouldn’t be sitting here.” I said, instinctively grabbing his leg above the knee and giving it a friendly shake. It was an innocent enough gesture…nothing two buds wouldn’t do…but I found my hand shaking, and lingering on his leg. I stared at my hand as though it were separate from my body…my thoughts begging it to move, but my muscles unable to pull it away. I chugged on my beer and sat back on the sofa, my hand still on John’s leg as it pulled upward on his thigh.
John didn’t move, and didn’t say anything. He just sat there with eyes still closed as my hand simply remained in-place. My eyes kept darting back-and-forth…glancing at my hand, his face, and finally at his crotch. I could detect movement behind the fabric of John’s pants, and felt a stirring between my own legs. I was becoming overwhelmed with the need to feel the heat and strength of another man in my grip. Never in my life had I ever wanted this before…but a bewildering sense of lustful novelty and danger began to creep over me.
“Oh man.” John said, with a yawn and standing up from the couch. “I’m going to take a quick rinse and get the hospital smell off me.” He said, stretching his arms and bending his back…highlighting the bulge in his pants. “Maybe even a cold one.”
I said nothing in return, and watched him walk toward the bedroom. John didn’t close the door, and a few moments later I could hear water running in the shower. I had to respect him for this approach. By walking away, we could both see my clumsy gesture as nothing more than innocent contact, and he could avoid seeming to pressure me. The ball was now fully in my court, and my stomach churned with nerves. “You don’t need this…you’re not fucking gay.” I said to myself. “But it was fun…in a different sort of way.” My mind reeled with contradictions. “You know you’ll never do this again. It might make John feel better.” I told myself, trying to pretend my desires were less about me, and more about easing a friend’s conscience.
I drank the last of my beer, took a deep breath, and stood up. My legs seemed wobbly as I stepped slowly into John’s bedroom. Only one lamp on a nightstand lit the room, and I could see John’s clothes in a crumpled pile at the foot of the bed. “Oh fuck…get a grip!” my voice said within my own mind. I took another deep breath and entered the bathroom. The layout was similar to the large space I enjoyed in Steve’s condo, but had a more modern feel, with lots of glass and stone. John was standing behind the clear glass walls of the shower…his hands against the wall, with the water streaming down his muscled back and toned legs. My hands were still shaking as I pulled off my shirt and stepped out of my jeans. I was half-hard as I walked into the shower and stood behind John. Reaching out with my arms, I gripped his shoulders and gave them a firm rub. I would have used a gentle touch, and traced a finger over a woman’s body…but I wanted this to be about men, interacting like men. Tenderness wasn’t going to help me get through this, and I wanted John to know that from the start.
“Feels good…but you don’t have to do this.” John mumbled as I kneaded his shoulders. “Don’t do anything you’re not interested in, just to relieve my guilt.”
“Oh…I think you caught my interest.” I replied, stepping closer and pressing my swelling cock into the crack of his ass. “I’m not sorry you showed me something different. Just be aware that I can’t ever see myself doing this kind of thing ever again…with anyone else.” I moved one arm around to his chest, taking note of how different it was to feel another male body this way. My hand rubbed across the neatly trimmed hair on John’s chest…the firm muscles of his pecs feeling so different than the silky softness of female breasts.
“Damn…this place is going to be dull when Steve gets back.” John said, reaching back between his legs, teasing the head of my cock and brushing the bottom of my balls.
I continued tracing my hand down John’s chest and rippled abs until my fingers met the base of his shaft. John stood up, pressing his back to my chest as I wrapped my fingers around his swollen tool. I could feel the heat and hardness under the silky outer skin as I slowly stroked the only other cock I had ever touched.
John grabbed a bar of soap and slowly turned around, our hard cocks bouncing against the other. “If this is truly your last time, then we’re going to make the most of it.” John said, gripping our dicks together with a soapy hand, while the other lathered my chest. “I think it’s always more fun when everything is squeaky-clean.”
I just stood there, enjoying the firm touch as John soaped my body. Once satisfied my front was sufficiently clean, he wrapped his arms around my torso, pressing his body against mine while roughly sucking and biting at my neck. His slick hands ran down my back and over my buttocks. After giving each cheek a firm squeeze, John slid his soapy fingers in my ass-crack, pressing one digit into my tight pucker.
“Oh fuck!” I grunted as a second finger pressed for entrance into my sensitive hole. My hips bucked away from the intrusion, making my cock twitch, and slide against John’s stomach.
“Sorry, man…but if you liked the way it felt when I ate your ass the last time, then it’s got to be clean for me to do it again.” John said gruffly before licking my neck and planting a firm, insistent kiss to my lips.
Once again, my immediate reaction to kissing another man was less than positive, but my apprehension soon faded as the gesture imparted a sense of rugged lust and trust…not loving intimacy. I returned John’s strangely masculine kiss more easily this time, having more confidence that he knew what I wanted and how I felt about it.
“I love how straight guys kiss…never really sure of themselves.” John said, with an evil grin. “On your knees, Glen…now.”
I was both put-off and aroused by the demanding tone, and found myself sinking toward the tile floor as John pushed down on my shoulders. His hard cock dragged over my body as I knelt down, and smacked hard against the bottom of my chin. In spite of having done this once before, the sight in front of me seemed strange and unreal. Having been in countless locker rooms and gym showers, the sight of naked men was of little interest to me at all. The only other hard cocks I’d ever seen were in porn movies. Yet here I was…willingly kneeling on a shower floor, staring at a hard prick as a ribbon of clear pre-cum trailed down to my chest. This time I kept my eyes open while I stuck out my tongue and licked my way down the throbbing shaft. Moving back toward the tip, I pressed my lips against the spongy head and collected the slick fluid on my tongue.
“Ummm…yeah…that’s it, bud…suck it for me…suck my dick.” John moaned, gently pressing a hand to the back of my head.
The taste of warm water and soap filled my mouth as I inched slowly down the white-hot pillar of flesh. I learned enough from the first encounter to know that I had to keep the spit flowing to make progress easier. I took my time, and John was patient, as I adjusted to the thick intruder without gagging. The first time, I could barely manage half the length. I amazed myself that after several persistent attempts, I felt John’s neatly trimmed hairs brush against my nose. My mouth and throat felt impossibly full, and my lips couldn’t stretch any further. The moans of pleasure I could hear through the splashing water told me that I was making another human being feel incredible…and that we trusted each other in the deepest way possible. It still wasn’t love or romance…but it was a bond between men that I had never felt before. Despite an odd of sense of pride in making John feel good, I also had a feeling of shame and degradation. It was just a nagging thought that I shouldn’t be here, doing this kind of shit.
“Oh damn, man…you are one fucking quick learner!” John said, holding my head firmly and fucking my face so deeply that his balls slapped against my chin. He wasn’t being brutal about it, but was insistent. I coughed and gagged around his cock a few times until I learned to relax my throat. Spit coated my chin and clung to his hairless sack. “Oh fuck…yeah…lick my nuts…come on, Glen…lick that hanging fruit.” John hissed, pulling his cock out of my mouth, and pushing my head further down.
Pressing my nose into John’s scrotum, I was fascinated at how soft and smooth the loose skin felt against my face. I had the same reaction the first time around, but the sensation still held a taboo aura of the unknown. His balls rolled easily beneath the silky cover, which hung low due to the warmth of the shower.
“Fuck, that feels good…that’s it man, suck on those balls.” John moaned as he pushed my back towards the floor. “Lay back man…I’m going to sit on that handsome face!”
The hard, tile floor was mildly uncomfortable, but it at least the water made it feel warm. I was laying flat on my back, with John hovering above me…his feet against my shoulders and his sack draping over my nose and mouth. My cock was painfully hard. I had started this, and still couldn’t believe the situation I was in. No one at home would ever believe I was capable of behaving this way.
“Remember how hot I made you feel when I licked your ass, straight-boy?” John said, spinning his body around, straddling my torso, and squatting on my chest. “Time to return the favor, bud…go ahead…put your hot tongue on my little pucker.”
I stared at the firm, muscled globes in front of me…not really wanting to comply, but feeling an odd sense of obligation. I had, on occasion, tried to interest a few girlfriends in ass-play…but it never held a strong fascination for me. I gasped as John leaned forward, taking my cock into his mouth, and shifting his ass even closer to my face. “He’s right…it did feel fucking incredible.” I thought to myself, while still hesitating to do the deed. This seemed like the raunchiest, dirtiest, thing I had ever been asked to do…and for some reason, heightened my arousal even more. I took a breath, and extended my tongue to the outer edge of John’s sphincter. I could feel every ridge as his ring twitched in response to my probing. I half-expected to feel sick when I started, but was surprised to find the experience incredibly erotic. John’s freshly-cleaned backdoor offered no nasty surprises, and the eagerness of his cock-sucking increased with every lick across his rosebud.
“Oh god, yes…just like that, man…lick that hole…oh fuck!” John cried out as my resolve strengthened, and I began working his ass in earnest. John used one hand to encircle my cock and balls…licking my nuts as I lapped harder and faster at his ass.
I could feel my sack tighten as John used unbelievable skill on my aching tool. “I’m close…oh shit…I’m so fucking close!” I panted, moving my face out of the crack of his ass.
“Feed it to me, man…give that load!” John grunted, before swallowing me whole and plunging a spit-soaked finger into my ass to massage my prostate.
“Oooohhhh…sssshhhiiiiitttttt!!!” I howled, as my body jerked, and four heavy streams of spunk shot into John’s hungry throat. He continued sucking me dry as my body slowly relaxed, and the convulsions faded.
“Damn, you have some tasty cum!” John said, spinning his body above once more. The head of his cock was an intensely deep red, and his nuts were drawn tight against his body. “Oh god…I need to shoot, man…take it…taste every fucking drop!” John groaned, as he lifted my head off the wet floor and pushed his hard cock into my mouth.
“Mmmpphhh…mmmppphhh” were the only muffled sounds I could make as John held the back of my head and pushed deep into my throat. It was clear that I no longer had a choice in the matter…I was going to swallow another man’s cum. As I could sense John’s body tighten, and his thrusts becoming more urgent, the familiar sense of excitement mixed with revulsion swept over me again.
“Fuck…fuck…here it comes, man!” John shouted, holding my head tightly and pushing fully into my mouth. “Fffffuuuccckkkk…ddddaaammmnnnn!” John screamed, panting heavily as load after load filled my mouth.
The first blast shot hard against the back of my throat, and I gagged around the throbbing prick that filled my mouth. John’s spunk was warm, slick, and a bit salty…maybe not the best taste I had ever encountered, but certainly not the worst. To be honest, I had tasted my own load a few times in my youth, and his was very similar. It was the delivery method that made all the difference. I had little choice other than to swallow as much as I could, as several other streams poured down my throat…the excess squeezing past my lips and running down my chin. John held my head firmly in place as my tongue worked the last drops from his deflating member.
“Oh man…shit…you took that like a champ.” John said between halting breaths, pulling his soft cock from my mouth and offering me a hand to stand-up.
“Fuck…that was…different.” I said, swallowing the last of my friend’s sticky load, and wiping the goo off my chin. “I guess I can understand why some of the girls in college wouldn’t swallow.” I continued, with an exhausted chuckle.
John pulled me close to him, and centered our bodies under the spray of the shower. He once again pressed his lips to mine, darting his tongue into my mouth and mixing the flavors of our remaining seed together. “Mmmmm…I like how my cum coated your tongue…very tasty.” John said, while biting my lower lip, grabbing the soap, and reaching down to lather my cock and balls. “Better get the boys cleaned-up for round two.”
“I don’t know about round two, John…you pretty much wore me out.” I answered, returning the favor and soaping his chest.
John smiled widely. “I don’t get to corrupt hot straight men very often. If you think I’m going to let you leave town on a “one-and-done”, you’re very much mistaken.”
“Hahaha…I’ve been known to have to some intense all-nighter’s with a smoking-hot lady or two…but I don’t think you’re going to stir the same kind of interest.” I said, smacking his ass with a soapy hand.
“Well…you may be right. But I’ve already got you half-hard again, just washing your cock.”
“I think that’s more like half-down, not half-up.” I said sarcastically.
We finished what had to be the longest shower of my life, with my fingers pruned and my body nearly exhausted. After drying-off, I looked for my clothes, but John had already gathered them in his hands. He walked into the bedroom and tossed them on chair before lying down on the bed. I followed, and started walking toward my pile of clothes.
“No need to be in such a hurry…you don’t have to be anywhere until tomorrow afternoon.” John said with yawn. “Just lay down and take a break…we can grab another beer and shoot the shit after our bodies recoup.”
I had just pulled on my briefs when I look toward John, to see him patting the other side of the bed. “Hey…it was fun…but I don’t need to be doing a sleep-over with another dude.”
“Seriously? We just ate each other’s cum, and you’re nervous about being on the same bed with me?” John said with a hearty laugh. “Just get your ass over here…I promise there are no cameras recording the event for posterity.”
I was tired, and John was right to point out the absurdity of my reasoning. “Fine…I could use a quick nap. But you’re still not getting any fucking flowers in the morning.”
I must have been more tired than I thought, since I dozed-off not long after hitting the bed. I’m not sure how long I was out before being wakened by the feel of hands massaging my back.
“Hey, sleepy-head…it seems all that hot water dried your skin. This stuff should help.” John said, squirting more lotion into his hands and spreading it over my back.
For a moment, I thought I should get up, and head back to what would soon be my former home away from home. The kneading motion of John’s fingers, however, made me willing to endure the back rub a bit longer. He took his time, really working my muscles while restoring the moisture to my skin. John slowly progressed down my spine and to my lower back, his fingers nudging just under the waistband of my briefs.
“I’m pretty sure this is going to be an all-over job.” John said, tugging at my underwear while pulling them down and off my legs.
Instinctively, I started to lift my chest from the bed, but John pressed my body back towards the mattress with one hand, while rubbing my ass with the other. I could feel that John was kneeling on the bed next to me, as his hands slid across the back of my thighs, calves, feet, and back up again. The soothing lotion and his skillful touch felt wonderfully relaxing. I guess I was still a little groggy, as it didn’t register where all this might be heading. My mind was lifted from the fog, as John spread my legs apart, knelt between them, and quickly buried his face into the crack of my ass.
“Aahh..oh…fuck!” I gasped, as the invasion sent a sudden tingling jolt through my body. I was reminded of how strong the sensation was the first time John did that to me, and the repeat was no less intense. My cock quickly swelled between my belly and the bed as John slowly licked a path from my ass, to my balls, and back again.
“Damn…that is one fine hole.” John mumbled, before plunging his tongue into my brown-eye. I gripped the sheets and moaned, writhing on the bed as he ate my sensitive ass. “I don’t know…I think someone might be up for round two after all.”
“Oh fuck…that has no reason to feel so good.” I moaned, as John pushed a finger into rosebud and lapped the back of my balls.
“Flip over, bud…let’s see if I’ve managed to pique your interest again.” John said in husky voice, helping me roll over, and keeping his body between my legs.
My cock was rock-hard, and John immediately took my tool into his mouth while still fingering my ass and rubbing my balls with his thumb. I couldn’t help but wonder why the women I dated were so vastly inferior at a task that seemed so simple. As he did before, John brought me to the edge, and back down again several times…torturing me with the reward of orgasm, only to deny it over and over again. Eventually, John slowly licked and kissed his way up my body…straddling me, and bringing his dripping cock to my lips. I grabbed both of his buttocks, and pulled John toward me, swallowing his hot pole more easily than ever before. Once an easy rhythm had started, my hands traveled up John’s torso…kneading his pecs and pinching his nipples as I vacuumed the turgid rod in my throat. After a few minutes of providing the best blowjob I could muster, John began sliding down my body, licking his way down my neck and chest. I was certain that he would impale himself again my aching cock, but John kept sliding farther down. His loose balls dragged over my dick, smearing clear precum down the shaft until John’s tongue was once again teasing my swollen helmet. John’s oral talents were so good, that I barely noticed he had placed my legs on his shoulders. Releasing my cock, he nibbled his way back up my torso until our eyes met, and his cock bumped against my slick and twitching pucker.
“Now is when you need to trust me, Glen. I want to share something with you that you can’t understand until you try it.” John said with a serious tone.
“I…uh…I…don’t know, man.” I mumbled, as my body trembled with nerves. “I do trust you, man…but…shit. Won’t it hurt?”
“I won’t lie to you…it can be painful as hell, at first…but it fades quickly, and will feel better and better the more you relax.” John said, with a calming tone as he reached for a bottle on the nightstand. “Open your hand.”
With my mind racing through a million scenarios, I hesitantly lifted an arm and opened my hand. John squeezed a large amount of very slippery lube onto my palm. I could feel the heat of his cock pressing at my rosebud.
“I think you’re being truthful when you say this will never happen for you again. You shouldn’t let this go, without having tried something fucking incredible.” John could sense my apprehension. “I won’t hurt you, man…you have my word on that.” He said, shifting his hips so his cock rested on mine. “Take that lube, and spread it on my dick.” John said with a tone that sounded more like a command than a request.
My heart pounded so hard I could feel it. I reached down, gripped John’s impossibly hard prick, and coated it thoroughly with the slick fluid. When I finished, John pushed my legs forward, lifting my hips so high that my own precum trailed to my chin. He spat on my hole, and worked the saliva into my pucker with a slick finger. Once satisfied, he gripped my calves with firm hands, spread my legs wide, and pressed his cock to my reluctant entrance.
“Take a deep breath, and push against it…like you were taking a dump.” John instructed, as he pushed harder against my ass.
I worked hard to concentrate on trying to relax and doing as he asked. John was patient, nudging my hole gently at first, and then more insistently. I closed my eyes and took a deep breath, focusing my efforts…and then it happened. The head of John’s dick slipped quickly past my tight sphincter. John stopped quickly, leaving his cock in position, knowing I would need time to adjust.
“Aargghh…oh fuck!” I screamed, as the initial pain shot through me just as John described. Just the head of his prick seemed enormous, and I couldn’t imagine taking any more of that thick pole. Tears welled in eyes as the pain slowly subsided, and my breathing normalized.
“Relax…breathe…you’re doing great, man. It only gets better from here.” John said, before leaning down to kiss me with the same masculine touch as before.
“Huge…feels so fucking huge!” I grunted through clenched teeth as John slowly inched forward, backed off, and then pushed forward again. It may have taken ten minutes before John managed even half his dick inside me, but his slow and attentive manner made the whole thing tolerable. I wasn’t so sure about taking this step, and now I had a feeling that was hard to describe…almost like I was being feminized in some way, and that wasn’t setting very well.
John seemed to sense my mixed emotions, and worked to keep my perspective in focus. “Cool, man…so damn cool…you’re one tough fucking bastard!” He grunted, slapping my chest with the back of his hand like a primal ape. “Most straight guys would have run away by now. You must be one kinky fuck with the right woman!”
Even in my state of sensory overload, I could see through John’s attempt to “butch-up” my feelings, and I couldn’t help but respect him for it. Strangely enough, the pain and discomfort were starting to fade, and my fear of being split in half dissipated. I could now begin to feel every ridge and vein of John’s impressive manhood as he passed through me with gentle strokes. I couldn’t believe I had gone this far out of horned curiosity. The level of trust I placed in a guy I’d likely never see again was huge…but I also knew the impending distance between us is what made it possible. There’s no way I could go through with this if I thought repeat performances would be expected.
“Damn…that is one hell of a learning curve.” I said, in as relaxed a tone as I could manage, trying to convey that I was going to be alright. I clenched my teeth, reached with one hand to squeeze John’s pec, and gripped his ass with the other. “Come on, fucker…make me feel it. If we’re going to do this, we’re not going to be pansies about it.” I grunted, slowly pulling him toward me until his hips were firmly pressed against my ass. “Gggggrrrr…fffuuuccckkk!” I moaned as his cock slid fully inside my bowels…the heat of his prick radiated through me.
John’s eyes locked onto mine with a lustful stare. His breathing became deep and ragged as he started to withdrawal, leaving only the head of his cock inside before pushing forward again. His first few movements were slow and even, gauging my sounds and body language for signs of discomfort. John’s pace began to quicken with every successive thrust, until he was fucking me with a steady rhythm. My cock had softened considerably…but with every deep stroke across my prostate, previously unknown sensations of pleasure pulsed through my body, and my dick hardened in response. This was strange, intense, and felt unbelievably good. I could never convince any of the guys I know at home that taking it in the ass would be a good idea, and I was more than a little amazed myself.
“Shit…you’re so fucking tight!” John said, quickening his pace as he plunged deep into my ass. “Damn, you feel so good!”
By now, my cock had never felt so hard, and it tingled with every stroke John buried inside me. I looked down to see a man’s body, athletic with rippled muscles, pressed against my ass and the back of my thighs, using me to satisfy his own sexual need. The moaning sounds above me were low, guttural, and distinctly masculine…not at all the soft feminine coos I was used to hearing. I knew this was going to be a secret pleasure for me…nothing that I could ever comfortably reveal with my circle of friends back home. Some part of me still couldn’t understand why I wanted this, but another was lost in the incredible sensation, and the illicit nature of the activity.
“Come on, man…stop playing nice…fuck me…fuck my ass!” I hissed, reaching up to pound John’s pecs and pinch his nipples.
John just grinned, moved his hips back, and then quickly plunged fully inside. His forceful thrusts slid my body up the mattress until my skull was pressed against the headboard. Sweat dripped from John’s nose and onto my chest. The ring of my once-virgin ass still burned from the intrusion, but the unusual feeling of pleasure made it seem like a minor annoyance. My cock was so incredibly hard, and the precum flowed heavily, filling my naval and sliding down the side of my belly…I couldn’t even touch it without fear of shooting immediately.
“Damn…you’re one fucking hot bastard!” John grunted, before extracting his huge member, pulling my body down on the bed, and gruffly flipping me over onto my stomach.
My ass felt like a gaping canyon without John’s cock filling the void. He reached beneath me, tugging my prick down, and forcing it to protrude between my legs. With the strength of my arousal, it was a somewhat uncomfortable position…but the discomfort lessened as John began licking the sticky helmet, my balls, and my tortured pucker.
“That is one fine straight-boy ass!” John said, slapping my hairy cheeks before laying his body on top of mine. His hard cock slid between my moons as he whispered hoarsely into my ear. “I know you want to cum, Glen…but not just yet…I want you to remember what might be the last good fuck you ever get.”
I had no response as I felt John lift his chest of my back…his hands pressed to my shoulders as though doing push-ups. Almost instinctively, I spread my legs apart, and felt his hard and warm cock pressing at my overstretched entrance. John wasted no time, and thrust forcefully into my bowels.
“Mmmmpphhh…fffuuucckkk!” I growled, with my face pressed against the mattress. John stayed deeply planted, allowing me to adjust. The sensation of his dick filling me up again, with his loose sack draping over the head of my cock and sticking to the back of my balls, was almost more than I could take. A few more seconds passed before John began fucking me in earnest. The weight of his body, and the force of his thrusts, was providing more stimulation to my sensitive tool as it rubbed against the bedding. I needed to free my steel-hard cock, and slowly began raising my hips…eventually moving into a doggy position as John continued his deep pounding. Even that didn’t ease the building climax that I couldn’t hold back any longer. “Oh fuck, man…I’m gonna cum…I’m gonna cum!” I shouted, reaching back to feel John’s cock sliding into my ass.
John wrapped one strong arm around my chest, pulling me upright and pressing me against him. With his cock still buried deep inside me, he gripped my aching cock with his other hand and began quickly stroking me with a spit-soaked fist. “Fuck, man…you’re clamping around my cock even tighter! Shoot it, bud…show me that load!”