Trip with Friends Ch. 01

"Okay, so I guess that answers that. Or doesn't, really." I smiled.

"Anything else?"

"What is 'the next step?'" I figured the anticipation was going to kill me if I didn't ask.

"Are you sure you want to ruin the surprise?"

"I am."

"Alright. The next step is that after this wonderful, relaxing bath, I am going to take you into the bedroom and introduce your cute little ass to my cock."

"Look, this has been fun, but I don't know whether I am ready for that. You have a really big dick."

"Thank you, Jon. I am aware of my size and I have done this many times before."

"What do you mean? Fucked guys, or fucked guys who have never fucked guys before?"

"Yes."

"How many times?

"For which one?"

"Yes."

"Touche. In the first instance, I honestly can't count how many men I have fucked, but it is in the hundreds. I am wealthy, charming, good looking and I live in a city that is known for its homosexual population. For the second question, you are my forty-first."

"Forty-first? Jesus."

"No, he was twenty-second." He laughed. "I guess you could say that since I am one of the few men that see the grey, it has become a bit of a past time for me. Not many men notice the subtle cues, so they don't see the missed opportunity. I don't like missed opportunities, in life or in business, that is why I have done so well in both. And also, I have come to enjoy it. Having a virgin in this respect is different than when you have your first encounter heterosexually. Since I am the one controlling the encounter and I have the experience, I can make it highly enjoyable for both parties, as you have already witnessed. I also like the idea of corrupting a man from what he thought he was capable of or who he thought he was, not that I believe the tripe that homosexuality is corruptive, obviously. So, with that, I think we are warm enough now to get out and get to the main event. What do you say? Do you trust me to take your ass for the first time, knowing what you know now?" He stood up and extended his hand to me.

I contemplated it for a moment. Like Isaac had said, I didn't want to miss an opportunity, especially one that was so tempting and unusual. I was afraid, but I thought that the same must be true of women who decide to let a man enter them for the first time. I extended my hand and let Isaac help me up. We got out of the bath and toweled off.

Isaac led me into the bedroom and placed me at the foot of the bed. He kneeled down and began sucking on my cock. Once again he showed his abilities far surpassed mine. He told me to lift my legs off of the floor and to lie back onto the bed. I did so and he kept stroking my cock while he began rimming me. It was very pleasant. My cock was hard as a rock.

He moved his mouth back to my cock and placed a finger at my asshole. He began stretching me out with his finger, slowly and surely, while edging me with his mouth. He added another finger. No discomfort. While his two fingers were inside me, they stroked a spot that I had heard about but never felt before, my prostate. It was like an electric shock going from my ass to my cock and brain. Strange but extremely pleasurable. A third finger. He had me on the brink of orgasm for what seemed like an eternity. Finally, he removed his mouth and let me come down from my pre-orgasmic high. I looked up to see him standing.

"I am going to remove my hand from your ass now. Just relax and we will get to the main event."

"Your hand!?!"

"Yes, while you were jerking and twitching, I got my whole fist in your ass. Didn't you notice?"

"Nope. Okay, uhhh. I guess just take it out, then." I began to feel how full my ass was with his whole hand. He twisted it and I jumped, not because it was painful, but because it once again stroked my prostate. He shifted the shape of his hand from a fist to a flat shape and began removing it. I tried to relax, but it was hard. As his hand left my ass, I felt a strange emptiness I had never felt before. Not like emptying your bowels, more like how your throttle hand feels after a long motorcycle ride, like it is supposed to have something in it.

"Good, that went well. You didn't even need any lube other than my spit. I'm still going to use some lube with my cock, as fucking you will be a lot more movement. Stay right there."

"I appreciate that." I responded. Isaac walked over to a bedside table and brought out a bottle of lube. He came back to where I was and turned my legs on my side so that I was spooning, with my knees up near my chest.

"This is the best position for this part." He applied the lube liberally to his cock, making it glisten in the reflected city lights. He then dropped a large dollop on his hand and applied that to my ass, pushing it inside. "Okay, I am going to fuck you now. I am pretty sure you are ready. Discomfort is normal, but pain shouldn't be. If you feel a sharp pain, let me know and I will stop, but that isn't likely. Tell me you want this."

"I want this."

"What do you want?"

"I want you to fuck me."

Isaac's cock approached my hole. The head of his ten-inch member touched my rosebud and then pushed past it, with all resistance gone from when his fist had been inside me. His cockhead was like a drill bit, opening up new areas of my bowels for the rest of his length to follow. He began shallow and then moved deeper and deeper. My cock twitched between my legs as his member massaged my prostate. Because of the edging he had done to me with his blowjob, I came before he was halfway inside of me. My cock spurted up and onto his black sheets, marking them for him to see.

"Good. I love it when guys cum without touching themselves. I knew you would like this." I couldn't voice my response, I simply nodded and moaned. Isaac continued his onslaught of my asshole. He eventually reached bottom and stroked it in my depths for a short time. He then grabbed one of my legs and moved it so that I was once again on my back and Isaac was now fucking me missionary. He leaned down and kissed me passionately. His hands found their way to my ass and he grabbed and massaged my cheeks as he stroked the last few inches inside of me. My cock's turgidity had not subsided during his exploration of my depths.

He slowly stroked inside of me for the next few minutes, while passionately making out with me. I was in a constant state of arousal. He then began to increase the pace, fucking me faster and faster. He stopped kissing me at one point, pulling my ass off of the bed and placing my legs on his shoulders as he pummeled my ass harder and faster. My cock began spurting load after load as his furious pace tweaked my prostate every time. I felt his member expand inside of me and then I felt it pulsate as he began shooting his ejaculate into my rectal passage. He returned my ass to the bed, leaned over me again and kissed me on the mouth, gently this time. I returned it as best I could, although his ministrations had left me temporarily cum drunk and unable to respond completely.

He stood back up and slowly began removing his cock from my ass. I felt every inch as he pulled his massive tool out of my rectum, my dick twitching as he pulled. I groaned as he popped the head out of my ass, feeling just a twinge of pain. My anal passage felt so empty and strange. Isaac moved my leg so that I was on my side again and then slapped my ass.

"Goddamn, I love fucking virgins. You have a beautiful ass, Jon. I'll be right back." He left me lying there, with his cum oozing out of my gaping asshole, shocked at what had just happened. My cock was slowly deflating, yet I was still highly aroused. I reached down and began stroking my dick with one hand as I reached back to feel my asshole with the other. I felt some liquid on my hand and I lifted it to my face to smell it. It was definitely cum, and since I was already in pretty deep, I stuck my tongue out to taste it. It was definitely Isaac's cum, with its sweet flavor, but there was something harsher there that I also enjoyed. I reached back again and started feeling my gaping ring. It was still quite wide, and I could reach my fingers inside without resistance. I stuck my fingers inside and came out with more cum, licking it off once again. I was in the middle of this when Isaac returned.

He had clearly cleaned himself off a bit, as he was shiny with wetness. He smiled at me tasting his cum mixed with my ass juices and he climbed on the bed, sitting against the pillows at the head of the bed. "So Jon, how was your first time with a man?"

I turned around and moved up to sit beside him and turned towards him so I was on my side on the pillows. "Pretty good," I said, mischievously.

"Well, that's good. I did my best not to disappoint you," he responded with a smirk.

"Seriously, Isaac, I don't know why I never tried this before. That was the best fuck I have ever had."

"Sure you do. You never met the right person." He reached down and swung his cock around like a helicopter to punctuate the statement, chuckling.

"I don't know that I would have done any of this if I had known you had something like that in your pants. Honestly though, you may be onto something. I never thought of men as attractive until I met you. I guess I was culturally conditioned out of thinking of men that way or something. All I know is that from now on, I won't discriminate. After tonight, all sexes are on the table for me."

Isaac laughed at that, and I gave him a questioning look. "Jon, I said the same thing a long time ago and it has been some time since I have had a woman. One thing you don't realize about bisexuality in men is that one sex is a lot more eager, willing, and unlikely to play games when it comes to sex. That makes it a lot easier to decide which one to go with."

"But didn't you say that you enjoy fucking virgin straight men who have never had a woman before? How does that compute?"

"Trust me, it seems like more work but it isn't. Especially for someone with my wealth. Women don't come to this apartment expecting only sex. They see it and think, whether consciously or subconsciously, about the advantages that they can get out of being with me. Most men see only sex, especially straight men who are new to this experience. That is one of the reasons I like them, because they don't want anything more than to experience something they never have. Sort of like how women who fuck on the first date have a hard time getting around the established perception in the man's mind that that is all they want."

"Well, technically, this is our second date, if you count last night's chance encounter at the club."

"Yes, and I am sure you thought you would be impaled on my cock this evening from the moment we started talking last night."

"True enough. I will admit that something about you piqued my interest, though. You aren't like any of my gay friends, not that they are indicative of the gay population. You don't come across as gay in any noticeable way."

"And what would be a noticeably gay attribute?" He didn't appear offended, simply amused.

"I don't know. I guess just the usual stereotypes and I know that is not politically correct, but I don't mean it in an offensive way, simply from my experiences."

"I'm just pulling your leg, Jon. Really the only way you can determine whether someone is gay or not is if, when there is a nice hard cock in front of their face on the body of a hot guy, they will suck it or run away."

Isaac's words were clearly intended as an incentive for me, but I wasn't letting him get what he wanted that easily. "Well, I guess that is one way to find out for sure." I smiled back at him.

Isaac jumped up from the pillows, straddled my body and began stroking his dick. It grew quickly and soon the tip was close to my face. "So? What will it be? Planning on running away?"

"No fair, you have me trapped. I guess I don't have a choice." I stuck out my tongue and licked the tip of his mammoth member. I began slowly, worshiping his dick with long slow licks on the shaft and tip, all while staring up at him. His abs and pecs framed his face from this angle and he looked really hot. I moved my hands up to stroke his shaft as I began to work on him. Due to the angle, I couldn't get very deep, so I focused my efforts on the head of his cock, while stroking him quickly.

Jon reached behind him and stroked my shaft, returning me to hardness. Then he licked his hands and lubed up my dick with his spit. I continued to suck his dick and he continued to jerk me off for the next several minutes. Then, he pulled back and positioned my cock at his asshole again. Slowly sitting back, he impaled himself on my shaft and I felt his wonderful tightness envelop my turgid member. I grabbed his hips and fucked my dick up into him. He groaned in pleasure and stroked his dick as I fucked him.

"I want you to cum inside of me, Jon. I want you to blow your load inside my asshole. Then, I am going to make you eat it out of me. I want you to taste your cum mixed with my ass juices." Isaac continued to rock back and forth on my cock, massaging me by tightening his ass muscles.

I fucked him for several minutes like this, but I wanted to change positions. I grabbed his hips again and pushed him backwards, keeping my dick inside of him as I rolled us both so that I was on top of him in the missionary position. He was now lying on his back with his cock vertical as he held it by the base. I began long, slow strokes into his ass as I watched him play with the monster between his legs.

"Do you like watching me play with my cock, Jon?" I grunted in the affirmative. "You like seeing my big, fat cock get stroked in your face?" I grunted again. It really was big enough to be pretty much in my face. I had lifted Isaac's ass off of the bed a bit to get at his asshole more easily and this caused his cock to be almost to my neck in height. It gave me an idea. I lifted him up a little more and then I craned my neck downwards to take his member into my mouth. I couldn't fit much of it in without having to pull out of his ass, but the effect on Isaac was noticeable. "Fuck yes, Jon! Suck my cock while you fuck my ass. Such a good little faggot. I can't wait to turn you out to some of my friends. They are going to fuck you ragged. You'll be so full of cum by the end of it that you won't need to eat for a week." The idea of being fucked ragged by a group of men and filled with their loads had become a huge turn on for me over the course of this evening.

Isaac began stroking faster and I tried my best to speed up as well while keeping his dick in my mouth. I was moaning around his cockhead as I fucked him, approaching the point of no return. I began cumming inside of him and clamped my mouth down on Isaac's cock so as not to lose it in the process. Isaac groaned deeply and I felt his first spurt fire off into my mouth. He spurted several more times and I tried my best to swallow as I emptied my load into him at the same time. I collapsed on top of Isaac, his dick popping out of my mouth and falling onto his chest, firing the last spurts sandwiched between us. My cock softened and came out of Isaac's ass as I lay in his arms. I reached between us and collected the remnants of his load and brought them to my mouth, savoring their flavor. I rolled off of him, exhausted. I felt movement on the bed and opened my eyes to Isaac's ass in my face, with my cum dripping out into my mouth.

"Taste your cum, Jon. Eat my ass out and clean the mess you made."

Despite my initial revulsion to the idea, I could see the eroticism in it and so I moved forward tentatively to lick his ass. I noticed the faint ass smell mixed with my cum as I licked his butthole. Not quite poo-smelling, but a sharp smell that get on your finger when you brush past that area accidentally. It wasn't good smelling, but it wasn't bad either. I started licking more vigorously and inserting my tongue into his ass. My cock had stretched it out somewhat, but not really enough to gape it.

I had long since gotten all of my cum out of him when Isaac moved off of me and lay down on his back again beside me. He kissed me sensually and then moved back up to the pillows. I joined him and lay across his chest, staring at his deflating cock. I wrapped my hands around it and played with it in a manner that was more about my fascination with it than any sexual intent.

"I'm having a party here tomorrow if you want to come. There will be a bunch of my friends from all over and I'd like you to be my date. What do you say?"

"Ummm. Well, I kind of said that I would hang out with my friends tonight at a straight club."

"Oh, right. Invite them too. I'm sure they will like the party as well."

"I'll ask them, but I'd love to come."

"Good. Do you want to sleep over here tonight? I've got some spare toothbrushes in my bathroom if you need one."

"Yeah, that would be great." I looked up at him and he smiled at me. I kissed him again and then lay back on the pillows. He got up and headed to the bathroom. On his way he stopped and looked back at me.

"Look, I know that this night has probably been a lot for you, but don't worry, it will all be clearer by tomorrow morning."

"Ok. Thanks." When he returned, I went to the bathroom and found a toothbrush in packaging waiting for me. I did my nightly ablutions and headed back to bed. Isaac was already under the covers lying on his side. I got in and lay on my side facing away from him, secretly wanting him to cuddle up behind me. Luckily, Isaac read my mind and soon I could feel his cock between my ass cheeks and his arm across my chest. I fell asleep fully contented.