Trip with Friends Ch. 01

"Crazy, I'd like to see it some time."

"Yeah?"

"Yeah."

"Let's go, then. I'll settle up the tab, you get our coats. Cool?" I was confused.

"What? Now?"

"Sure, why not? I have the show at home, it's not far."

"Uhhh, but what about my friends?"

"Didn't you say that you told them you wouldn't come home with them tonight until after they were done their orgy? I am offering you my place to hang out at and watch TV with me. No strings. Just hang out."

"I suppose that is what I said." I mulled it over, but I knew I was going to accept, because I didn't really have anything else to do and watching a weird cartoon sounded like as good an idea as anything. "Ok, sure. I'll get the coats."

"Excellent." He passed me his coat check stub and got out of the booth to head to the bar and pay the tab.

I went and got our coats and waited. Isaac returned after paying the bill and I thanked him to which he replied "Not to worry, I make too much money anyways."

As we left, Isaac said goodbye to the bouncer, who he called Ray. Ray saw the two of us together, smiled and said "Have an illuminating evening."

* * *

Isaac's apartment building was only a five minute walk away. We stayed pretty silent on the walk over, but I felt some tension, mostly from me. I guess it was weird going alone to the apartment of a guy who I knew was gay and hadn't been my friend since High School. But I chalked my nervousness up to that and nothing else. His building looked pretty new from the outside and once we got inside, I knew it couldn't have been more than a couple of years old, everything was really nice inside.

"This place has offices on some floors and residences on others. Different elevators for each so we don't cross paths. It's pretty exclusive, though."

We got in one of the elevators that Isaac had to use a key to open. It was really nice. He chose a pretty large number, in the twenties, so I knew we would be in there for a while. Isaac was staying a good distance from me, maybe a foot or two, but we were pretty quiet.

Isaac's apartment was beautiful. Glass windows all around, which he said were glazed on the outside so that you couldn't see in but he could see out. Entering the apartment, you were greeted with a great view of the inner Bay area. He had a large sectional couch with his TV in front of it. It was large for the time, but no one had LCD TVs at that point, so it probably weighed a ton.

"Nice TV, I don't think I've seen anyone owning one that size."

"Yeah, it was a hassle to bring up to the apartment, they had to remove the door. You want a bourbon? I have some nice Jim Beam."

"Sure, why not. On the rocks."

"Of course." Isaac walked off and I saw that attached to the living area was a nice sized kitchen and on one side he had a large liquor cabinet set up with a cocktail making station above it and a bar fridge set inside. I walked over to the windows and admired the view. I saw him approaching me in the reflection and so I turned around. He handed me my drink.

"To new friends and all the new experiences they bring," we toasted to that and each had a sip. "So, shall we? Why don't you have a seat and I will find the tape."

"Sure, thanks." I sat on the large sectional and waited as Isaac rummaged around in the cabinet underneath the TV. He found the tape he wanted and put it in the VCR and then came over to sit beside me. He sat as close as one could possibly get without our legs actually touching. I could feel the heat coming off of him and it was making me feel really nice. I glanced over at him and saw that there was a sizeable bulge in his suit pants, but I quickly looked away, embarrassed at what I had just done. He started up the TV and we started watching the first episode of Ren and Stimpy.

"I recorded them all after I watched the first one, I was so impressed with it. I can't believe this is a kids show. You'll see what I mean." He was right. It really was a weird show, with lots of sexual innuendos. Pretty soon, with my buzz and the tension in the room, we were laughing our asses off. Isaac's hand once again found itself on my thigh and my cock once again rose to the occasion. After laughing again, I ended up sitting back, with my arms on the back of the couch and Isaac sat back into them. I didn't want to move, for fear that he would notice, so we ended up just sitting there, with my left arm basically around his shoulders and his hand on my thigh. Like some kind of couple at home, watching a movie together.

The final episode ended and the screen went black. Isaac turned to me and looked me deep in the eyes. "What did you think, Jon?"

My throat caught for a moment. "Uhhh, yeah. Really funny, you were right."

"I'm always right. It's something you will learn about me."

"Uhhhh. I will?"

"Mmmmhmmm." Isaac moved closer to me, took my face in his hands and kissed me on the mouth. All of the tension that had been building up in the hours previous broke like a dam, and I melted into his kiss. I sat there, being kissed by a man for the first time in my life and I was hard as a rock. He removed his hands from my face and his hands went to my pants. This was going pretty fast but I was happy to tag along for the ride. He unbuckled my belt and removed it and then went for my zipper. He pulled away for a moment as he felt how hard my cock was.

"Nice, is that for me?" Isaac smiled at me. I nodded, almost imperceptibly. "Good, we are going to have fun tonight, you can trust me on that."

He fished my cock out of my pants and moved off of the couch to kneel in front of me. He pulled off my shoes and my pants so that I was bare ass naked on his leather couch. My cock has never been described as big, but it is average. I measured it as around 5 inches and of medium thickness. I've never heard any complaints, at least. But Isaac didn't seem to care, as he held onto the base and began stroking my cock. He spat on his hands and then dribbled onto my cock to get it really nice and wet. He put his face to my cock and then licked the tip. Then, he did something none of my girlfriends had ever been able to do. He deepthroated my cock in one stroke. He stayed there for what must have been twenty seconds, massaging my balls with his hand and tickling my asshole with a finger. I was in heaven.

He sucked my cock like that for a while, interspersing his deepthroating with short fast strokes that had me on the brink of orgasm multiple times. But, it seemed like he was able to sense it and he would stop just short. It was maddening in the sexiest way you can imagine. He eventually stopped, leaving me gasping for more as he stood up and disrobed in front of me. He was out of his clothes in almost record time, but I stopped noticing once his underwear came off. What he released was one of the biggest, thickest cocks I had ever seen in my life. It was thicker than Peter's and longer, too. It must have been ten inches and raring to go. I was mesmerized. It took me a moment to snap out of it, but the rest of Isaac's body was also very sexy. He was very fit, but not overly muscular. It looked like he had immense stamina. I was about to find out.

After undressing, he undid my shirt until we were both naked. Then, he climbed on top of me and straddled me. He began making out with me while his hands massaged our dicks together between us. It was a very erotic feeling, having my cock against his large member. He moved away from my face and dribbled some spit onto our cocks to lubricate them and very soon had me on the brink again. He knew what he was doing, though because he stopped and raised up onto his knees. He placed my glans against his asshole and I knew that this was the moment when I should say something. If I didn't want to go through with this, now was the time to make a point about it. I said nothing, I simply closed my eyes and tilted my head back as the head of my cock penetrated Isaac's asshole. My penis entered another man for the first time in my life. It felt as good as I thought it would.

I had had anal sex with women before, but always at my insistence and it never went on for very long, because they always ended up complaining about the pain. I guessed for gay guys, it was the only viable hole, so they were prepared to use it whenever. There was little to no resistance entering Isaac. He controlled the pace of my entrance, but he did not look uncomfortable at any point. As he slid down, I noticed that his cock was midway up my stomach and pulsing. I reached out to feel another man's penis for the first time. It would be hard to describe the feeling I had touching that magnificent member since I was also fucking a man for the first time, but it was an epic monster.

"Yes, Jon. Stroke my cock while you fuck my ass. Such an eager virgin. Uhhhh." I felt my cock bottom out in Isaac's ass and he moaned in pleasure. Isaac began bouncing up and down. His ass was really tight and I could feel that he was massaging my dick with his ass muscles as he rode me. He had me close to orgasm pretty quickly once again. All thoughts of condoms or any other kind of protection had long been forgotten as I succumbed to the pleasurable sensations flooding my brain.

"I can feel you are close. Fucking cum in my ass. I want you to feel what it is like to cum in a man's ass for the first time. You are my dirty little faggot tonight, Jon. Cum in me, faggot. Cum in me!" I erupted inside of Isaac's ass, spurting numerous times as my body shook from the intensity of the orgasm. As I came down from my high, Isaac stood up slowly, allowing my softening member to pop out of his ass, followed by a dribble of my newly deposited load. I sat there, on his couch, exhausted, even though I hadn't even done anything yet. Isaac moved to sit beside me, and began fingering his ass and tasting what came out of it. He stuck one finger into his ass and then moved it towards me, placing it at my mouth. I opened my mouth and he placed his cum-covered finger inside and I closed my lips around it. I tasted my own cum for the first time and I had to admit, it wasn't bad. It was odd, for sure, but not in a bad way. The whole situation had me at a level where anything could be sexy, and this was definitely one of those things.

I rested for a moment, watching Isaac tasting my cum from his ass and stroking his dick with his other hand. I realized that he hadn't come yet and I felt bad. I didn't really know how to return the favor, since anything involving his pleasure would involve activity on my part and I was as inexperienced as a virgin in that arena.

"Jon?"

"Yeah?"

"I want you to suck my dick. Don't worry, I will teach you how to do it if you can't figure it out. But I need your hot little mouth wrapped around my cock so I can give you a taste of my cum. Would you like that?"

"I think so."

"Good."

I got off the couch and knelt in front of Isaac. I stared at his monstrous member, wondering how to approach it. I decided to start slowly and grasped it at the base. I had a much better ability to appreciate its size than I had stroking it while I was fucking him. It started thicker at the base and tapered off at the end to a bit of a point. I always like a blowjob to be wet, so I spat in my hand and applied it to the head of his dick. I began stroking and moved my head forward. Up close I was in awe. Veiny, thick and powerful, I opened my mouth and accepted the head into it. I don't know what I expected in terms of taste, but I noticed a faint fragrance of urine with some sweat. Otherwise, it wasn't bad, just like the taste of anyone's skin. I moved my tongue around on the head for a bit, as I had always liked that and then tried to take more of it in my mouth. I could only take a few inches at first, it was like trying to take a sub into my mouth. I spent some time just adjusting my jaw to his size. I stroked his shaft as I tried to fit him into my mouth.

"I can tell you are starting to like this. You are getting used to my size. I want you to suck me until I cum in your mouth. Suck hard and fast. I am already turned on, so it won't take long. I want you to taste my cum straight from the source."

I started sucking Isaac's dick like he had asked. Hard and fast with my mouth focusing on the head, while I stroked the shaft in sync. Isaac's moans came fast and I could feel his dick twitching. His hand came down on my head and grabbed my hair, forcing me farther down on his shaft, almost to the point of gagging. His twitching changed to the bucking of his hips and I knew he was about to cum.

"Don't fucking stop, Jon. I'm gonna come in your faggot mouth."

I kept stroking as I felt the first spurt but kept my mouth wrapped tight around his cock head so I could catch it all. When it hit my tongue, I was struck by how different his cum tasted from mine. It was pleasant, almost sweet, whereas mine had been bitter and bleachy. Suffice it to say, I had enjoyed giving my first blowjob. I swallowed as much of his cum as I could, but it kept spurting, maybe ten or fifteen times, all heavy, thick loads. Due to this, some of it ended up dribbling out of my mouth. Eventually, the spurts stopped and I sat back on my feet, leaving Isaac in the afterglow. I licked my lips and grabbed the remaining driblets of cum, licking my fingers clean.

"So, how did you enjoy that?" Isaac asked rhetorically, as he could clearly see the grin on my face.

"Fucking amazing. I'm going to have to try again later to get more of that thing in my mouth, but right now my jaw hurts. You have a really big dick." I responded.

"Why, thank you, Jon. And thank you for the blowjob. For an amateur, you sure learn quickly. Now wait here for a moment, while I go and start us a bath. Have to get the smell of booze and cigarettes off of us for the next step." Isaac got up and walked out of what I would be inclined to call the atrium, leaving me to contemplate "the next step" in silence.

I had definitely enjoyed what we had done so far, but I wasn't sure how much I wanted things to progress. I got up and stood at the window, looking out at the city. I wasn't gay, or at least, I hadn't been until earlier in the evening. I had always liked women. But Isaac was the sexiest person I had ever met. He was commanding in ways that no woman ever could be, or at least none I had met. His body was amazing, taut muscle with incredible strength behind it. His ass was fantastic, something I had never considered before. And then of course, there was his dick. I guess I had always had a thing for dicks. I never liked girl/girl porn because I needed there to be dick in the mix for me to associate myself with. Invariably, the pornstars that I liked ended up having bigger dicks. I really loved it when a man with a large penis overpowered a small woman, making her cum over and over because of its size.

So, here I was, in a man's apartment who, having just fucked and sucked him to orgasm, had the biggest dick I had ever seen. Thinking about his dick again was making mine twitch in anticipation. I stood there, looking out at the city from full length windows, with a growing cock as Isaac returned. I didn't notice him until he touched me, and so I jerked in response but relaxed as he wrapped his arms around me from behind. One of his hands massaged my back and neck while the other moved down to my dick.

"Well, hello. To what do I owe the pleasure of this hardening cock? Are you getting hard thinking about little old me?" I moaned and nodded in response as his hand masterfully stroked me to full hardness. "Good, I want you dripping in anticipation for after the bath. Come on, let's get clean."

Isaac turned me around and gave me a long, sensuous kiss and then pulled me by my cock up the stairs, into his bedroom and then into the ensuite bathroom. The bath was a large and deep bath, something that I had always wanted, but never had. It was still filling, but was close enough that Isaac stopped it, saying that with two people, it would be pretty full. The bath was situated in the room such that it was against the window, looking out on the city, just like the atrium and the bedroom.

"I like my baths hot, so get in gingerly if you'd prefer." Isaac stepped into the bath, big dick swinging softly. He lowered himself and gestured for me to enter. "Come on in, the water's perfect."

I touched the water with my hand and found that it was quite hot, but I also liked hot baths and I didn't want to disappoint Isaac. I stepped in with my feet, cringing at the increased heat. I waited a moment for the burn to subside and then slowly lowered myself. The bath was big enough that we could sit across from each other with our legs straight, but intertwined. As I reached bottom, Isaac's foot moved so that it was sitting on my thigh, lightly touching my prick with the toes.

"So, I am sure that you are wondering a lot of things right now. Enlighten me." Isaac said, smiling as he teased my prick.

"Well, I was just wondering whether I was gay or not. I didn't think I was, but now I'm not so sure."

"You've heard of Kinsey, right?"

"Sure, that movie with Liam Neeson?"

"Exactly. Alfred Kinsey, the seminal sex researcher-slash-statistician. Kinsey said that sexuality is rarely an all or one proposition. It isn't black or white. Almost everyone is shades of grey. Up until now, you have had all white. This evening, you had your first taste of black. Obviously, in this analogy, white is women and black is men. Maybe you aren't very gay, maybe you are way over on the hetero side of the scale. But I touched on the only part of you that is gay and got you here, in my apartment, naked, in my bath, with my foot playing with your cock."

"I guess that makes sense. I never found any of my gay friends attractive, although I wonder whether that will be the case after this. So, does that mean that you have had women, too?"

"I have had them, but it was a long time ago, back when gay wasn't even a word we used. I was married once and had kids, but that has been over for many years now. Not the kids part, obviously, but the married part. Now I am exclusively men. I have long since lost my preference for women. Even amongst the men, I am very particular."

"Really? Then what made you pick me tonight? How and why did you think that I would be amenable to this?"

"Honestly, Jon? I could see it in your eyes. I don't fuck with flamboyantly gay men. I like my men to be men, not men with feminine traits. I am excluding submissiveness in this instance because it is neither feminine nor masculine. So, the men that I often look for are ones that are not stereotypically gay. Often, I end up 'converting' men to gayness, although I find the terminology in that sentence problematic. I would be more inclined to calling it 'expanding the mind' than 'conversion'. This is because I see that spark, or that hint of grey in men that others would call fully white or fully hetero. You remember Ray, right?"

"The bouncer, sure."

"Did Ray say anything to you the first time you headed into the Diamond Club?"

"Yeah, he told me that the club was pretty hardcore and that I should watch myself because they didn't like having judgemental straight people in there gawking at the gays."

"Exactly. See, Ray can't see the grey. Ray only sees black and white. A lot of gay men are like that. They think that bisexuals are liars and that you are either gay or not. Naturally, this comes with the territory of being in a society where you can only marry one partner at a time. Whoever you choose to marry becomes your sexual identity and then everything you did up until that point becomes 'being curious' or 'experimenting'. You see how that is problematic?"

"Sure, I get that. Makes sense."

"Right. So, I see the grey where others can't or don't want to. It's like politics. They think that if you choose one party, you stick to it. But if you are on the fence, a swing voter if you'll pardon the pun, then you are just undecided. I honestly don't know what you are, if you are bisexual, gay or straight. All I know is that right here, tonight, with me, you are as queer as a three dollar bill." Isaac laughed at his own joke and I joined him, genuinely amused at the whole situation.