Chapter 561 – Josh Helps Tyler Understand
It seemed pretty damned obvious that Tyler was adamant about me having sex with him. In a situation where relationships were not at stake or endangered by having sex with him, I probably wouldn’t have been able to stop myself, after secretly lusting after him for some time. But Tyler and Tink were very dear to me now, and I just couldn’t do anything to alienate their trust, friendship, and in Tink’s case, love. I was racking my brain to find a way out of this situation with Tyler. Being straight, I would have thought action of a sexual matter between the two of us might make him squeamish, with him begging me to stop or even getting sick at his stomach. I kept thinking, I could possibly talk my way out of this situation, or try something that would possibly make him sick at his stomach and even puke, as he mentioned earlier, touching another dude or having one touch him, would make him do. I felt cornered at the moment, a situation I rarely found myself in. Trying to explain to him that he really couldn’t understand intimacy between two males, not having experienced it himself, kind of painted myself into a corner, when he reversed psychology on me, telling me to show him so he could understand it, if that was possible. I decided I would try to hold out at all cost, thinking he’d give up rather quickly in the process, as sickening as he thought male to male sex really was, a crime against nature, as he described it.
We were both naked beside one another on the bed, at this point, me with a raging boner and him with his flaccid cock laying on his large balls. He showed no indication of being sexually stimulated. I was beginning to enjoy his passionate kisses, something he did seem to enjoy doing. “You do kiss as good as a girl, Josh. You’re pretty good at making out, actually. I like that,” Tyler told me, when we broke for air.
“I guess I should take that as a compliment, coming from a straight boy, but I’d rather think I could kiss like a hot guy. Think what you want to think, it’s your show at this point,” I replied, making him smile at me, then resume kissing me. I started running my hand across his chest, feeling the nice abs he had, and his semi-muscular shoulders. I couldn’t tell if that did anything for him or not. I was still enjoying his tongue in my mouth battling my tongue. I didn’t know what he got out of that, but he seemed really into it and committed to it. Hell, I was all for it. We finally broke for air again.
“Damn, Josh, you’ve got a hell of a boner there,” he remarked, looking down at my rock hard cock sticking straight up in the air. “I like the way it reaches up like it does. Mine sticks straight out when it’s hard,” he added. I smiled at him.
“I wouldn’t know. I haven’t seen you hard yet. This kissing doesn’t seem to be doing much to get your dick excited at all,” I replied. He smiled.
“Well, maybe there’s some things you can do to get its attention,” he suggested, smiling.
“You probably wouldn’t like it, as it would involve a dude touching your junk,” I warned. He gasped quickly, then settled down some.
“It’s part of what I need to experience, so I guess I just have to suck it up and try to enjoy it,” Tyler replied.
“Tyler, you don’t have to do anything. This isn’t going to do anything for either of us, if we’re both not into it. Passion is passion. Without it, there’s no meaningful sharing of intimacy. It can’t be one sided. I can make you cum and cum rather quickly, but it’s not going to be the mind-blowing orgasm I told you would be there. You have to participate in all of this also, otherwise, we’re wasting our time and jeopardizing our friendship. I don’t want to be responsible for losing you as a friend,” I told him. Tyler smiled and brought me into a hug.
“I promise to try my best. We might have to back up a few times, let me collect my thoughts, wrap my head around what we’re doing, and then go on,” he replied.
“Or, better yet, not do this at all,” I heartily suggested. He looked at me and shook his head, then he smiled.
“Oh, I need to feel the Josh magic that blew my brother off his feet,” Tyler replied, not giving me any indication, he was ever going to give up.
“Are you prepared to take my dick in your mouth and suck it, lick my balls and even lick and tease my asshole with your tongue?” I asked, very seriously. He almost choked at the thought, somewhat shocked, looking like he might get sick at his stomach. I thought sure I had him now.
“Uh, do I need to, or can you just do that to me?” he asked nervously, turning pale. I smiled.
“I thought you wanted the full experience, which requires anything I do to you, you have to do to me. It’s a melding of the souls, not just a cheap fuck, remember?” I asked. I think he was speechless for a few moments. “See, I told you, you aren’t prepared for what’s required to have a full meaningful experience you call the Josh magic. Tink understands and enjoys that. Tyler, as interested as you are in experiencing all that, you’re just not wired for it, buddy. It’s not you. You are straight, and Tink and I are gay. We understand intimacy between two guys. It’s not something you can handle or even want to handle. And, I don’t blame you at all, Tyler. It’s not going to help anything. If anything, it might traumatize you, and I don’t want to ever do anything to cause anything like that. I think too much of you. I care about you, like I care about Tink. Let’s please not do this,” I practically begged, my boner now deflating to an almost flaccid state, similar to Tyler’s. Tyler thought about it for a few moments.
“If Tink could handle it, not knowing anything about it during his first time, then I can handle it also. I’m sure he was just as skeptical about all of this, and turned off by it also during his first time. Like I said, if he can handle it, I can too,” Tyler professed. I shook my head, not gaining any ground to end this nightmare, but somewhat sexy nightmare. I mean the dude actually did touch my dick and I touched his, albeit just a few short seconds. “Josh, tell me what I have to do and I’ll do it. Don’t hold back. If my brother can do it, then I can too. I’ve always been able to do anything he’s ever done, and usually do it better,” Tyler somewhat bragged. I rolled my eyes. Was this some sort of sibling rivalry? Did he think he had to compete against is brother for sex with me? My thoughts were about to blow up my head at this point. Craziness was bouncing around inside my skull driving me half batty. Tyler grabbed my head and started kissing me again. I ran my hand over his chest and tweaked one of his nipples some, getting a reaction out of him. “What was that? What’d you do?” he asked, not able to understand what he just felt.
“Just a little nipple stimulation. Did it feel good?” I asked. He gave me a quick smirky smile.
“Uh, it was kind of interesting. Guys don’t have sensitive nipples like women,” he informed me. I smiled, then kissed him on one of his nipples, then gently raked it with my teeth, making him squirm some. “Okay, that was a little intense, I have to say. Who’d have thought?” he remarked. I looked down and saw some growth in his penis. It seems I struck a nerve. That somewhat encouraged me to go on and try more things. I thought I might end up hating myself, but he asked for it. I kicked my shorts off the ends of my feet, and climbed further up on the bed, pulling Tyler up with me. We laid facing one another our bodies not touching. I leaned in and kissed him passionately again, this time running my hand over his shoulders, then down his torso, and over his buttocks, getting a small moan out of him. I scootched myself closer to him, letting our chests touch one another, but not our junk. Suddenly, he broke off the kiss. “Is that your dick touching mine?” he asked, concerned. I looked down, and sure enough, my cock was fully erect and met up with his in my erect state. He scooted his loins back a little to give me more space.
“You have a problem with our dicks touching one another?” I asked. He looked a little squeamish. I smiled.
“Uh, just caught me by surprise, Josh. I guess it’s okay,” he replied, nervously. I smiled again. “It’s just I’ve never touched another dude’s dick before and no dude has ever touched mine. I know that’s going to happen, but you just surprised me when it happened as quickly as it did. I’ll try to be more tolerant and less inhibited, but this is all so new to me, so help me through it,” he asked. I kissed him tenderly then, trying to relax his nervousness.
“Tyler, you’re nervous as hell. You’re uptight, which is to be expected for your first time. Why don’t I give you a massage to relax you some, and let you get used to our bodies being together,” I suggested. He said that was okay with him if I thought it would help. I rolled him over on his stomach, then straddled his ass, making him gasp as my naked ass sat on his. I immediately started massaging his shoulders, feeling the tension he had locked up in his body. He was being so brave in a way, but I still thought he was crazy for even thinking he could go through with any of this. It just wasn’t him at all. I worked his arms, shoulders, neck, then down his back, making him Oooo and Ahhh, as I did, feeling him start to relax. I moved further down on his thighs, almost to the backs of his knees to work his glutes. He seemed to like that, actually, which surprised me. He said I had magic hands that made him feel wonderful all over. I jokingly told him that was part of the Josh magic he was going to experience. He chuckled saying, so far so good, as he was kind of into this. I figured he might not object to what I did to relax him, since he couldn’t look at me, but only feel my motions. I moved further down over his calves and began to work his semi-hairy thighs, then back up his buttocks squeezing his glutes, giving me a glimpse of his virgin love portal. The thought of my dick in that sweet hole of his made me rock hard and my cock start to ooze precum. I had to swipe if off my piss slit occasionally to keep it from oozing down on his thighs, possibly causing him to freak out with my bodily fluids touching his body, something straight men would generally freak out about. Still, I was enjoying the hell out of the feel of his body as my fingers and hands explored his backside and gave me a glimpse of his asshole. I got off the end of the bed and massaged his hairy calves which really made him moan. I finished at his feet, but since I had already massaged his feet earlier, I just tickled the bottom of them, making him giggle. Tyler was dramatically starting to relax now.
“Okay, your turn,” I told him, as I flopped down on my stomach beside him on the bed. Slowly, he got up and straddled my ass, sitting his bare ass on mine. I could feel his balls laying against my ass cheeks, making my cock feel like a steel rod beneath me, almost causing an orgasm. I tried to concentrate on relaxing myself.
“Am I doing it right?” Tyler asked me, as I felt his strong fingers knead my shoulders and then down my arms. “I’ve never done this before to another dude,” he seemed the need to inform me. I chuckled.
“Oh, you’re doing everything right, Tyler,” I chided. He playfully slapped my ass, telling me to behave. Damn, this boy might have some possibilities after all, I thought to myself. He gave my back muscles a thorough kneading, actually doing a semi-great job. “Seems I’m finding out about Tyler’s magic also,” I chided. He chuckled. While he did a thorough job on my shoulders, neck, arms and back, he was very brief on my buttocks. I was sure he didn’t bother checking out my asshole during that process at all. He was even very brief with my thighs, but then did a more thorough job on my calves, better than expected, I could say. He did try to massage my feet, but it turned into more of a ticklish thing for me, which we all know I couldn’t handle, hastily telling him to forget about the feet, if he didn’t want me to unintentionally kick his balls off. That was all it took to get him to stop.
“Okay, now what?” he asked, when he was finally finished, somewhat concerned about what came next. I told him to lay on his back next. He apprehensively did as I asked. His cock was still flaccid. I told him to forgive me for my boner at the moment, but his massage got me all excited, and I couldn’t help it. He admitted he got a little excited when I massaged him also, but it soon disappeared when he massaged me. That surprised me, and disappointed me at the same time. Tyler laying on his back, I straddled his pelvis and our junk met, mainly my balls were up against his, as his cock was still flaccid and mine was pointing to the ceiling at full mast, with precum still oozing. I didn’t have much of a way to hide my precum condition, situated the way were currently were. Tyler shook nervously for a few moments, then I leaned down and kissed him passionately, which caused him to calm down. I raised back up, then proceeded to knead his arm muscles from the front, then his neck, shoulders, then his pecs, getting a nice look at his pit hair, which almost triggered an orgasm, as he was nice and hairy there. I did a gentle nipple play, getting some stiffness out of his cock. Finishing up his torso I moved further down his thighs, almost to his knees, then massaged his thighs from the front. His cock was starting to get somewhat excited, leaving me to look at a semi he teased me with.
“Nice treasure trail,” I told him, running a finger down from his naval to his pubes.
“What the fuck is a treasure trail?” he asked, curiously.
“This little trail of hair between your naval and your pubic hair, Tyler,” I explained. He asked me why it was called a treasure trail. I smiled. “Because it maps out the trail from your naval to the treasure here,” I said, gently shaking his cock just a little, and only for a few seconds, making him gasp again and shake some. He wasn’t quite sure how to react.
“O k a y,” he replied slowly and apprehensively. I chuckled, telling him he learned something new about himself already. He wasn’t quite sure it was something he really needed to know. As I massaged his thighs, I moved them apart some, then lifted his balls with one hand, making Tyler gasp again, nervous as to what might happen. His cock was still flaccid. As I held his balls up to give me access to this taint, I massaged his taint for him. “Wow, that’s kind of interesting,” he managed to say, somewhat apprehensively. “I swear no one has ever touched my balls before, Josh, and certainly not what you’re massaging now.” I explained to him how I could feel the tenseness in his body by the tightness of his taint, hoping we could relax him even more massaging his taint. He was still guarded as to how to react to what I was doing. I leaned in again and kissed him, an act I learned distracted him from other things I was doing. I gave his calves a quick massage, having done most of the work on his calves from behind. Then I flipped over on my back and told him to do me. It took some time for him to work up enough nerve to straddle my pelvis, his loose balls and cock definitely laying on my junk. He cringed when he felt his junk come in contact with mine. I pulled him to me to kiss him again and again, hoping that would distract from his nervousness of our junk up against one another, although we weren’t doing anything with it at the moment. I was still rock hard. He was still flaccid, which somewhat disappointed me, hoping to see him with a rigid boner, excited he was naked with me as we engaged in some sensuous foreplay. He probably only considered it as a buddy helping out a buddy with a massage.
“Are you okay?” I asked, noticing how nervous he was. He gave me a forced smile. “Tyler, we don’t have to do this. If you’re uncomfortable with any of this, let’s stop and forget it ever happened. I’m okay with that,” I told him. He looked down at my hard cock, as if to say, my dick wasn’t okay with stopping. I kind of smiled, noticing what he was observing. “Hey, I can bury that in Jake’s ass tonight, so no harm done. I won’t be sexually frustrated if that’s what you’re worried about. I’ve really enjoyed the closeness we’ve shared tonight. You were very brave, but don’t traumatize yourself over something you’re not comfortable doing. I won’t think any less of you at all. Trust me,” I exclaimed.
“I’m okay, Josh. I just have to get used to it. The touching has helped. I can’t believe our junk is up against one another, but I’m getting used to it. We haven’t exploded or anything because our stuff is shoved up against each other. I’ll be okay in a minute or two. I’ve never been this close to another dude’s boner before. It’s a little intimidating,” he replied, cautiously. I told him he was a brave straight guy. He rolled his eyes. He became even more nervous when he had to massage my taint, but seemed delighted not to have to raise my balls to access my taint, my balls tight up against the base of my cock due to my raging boner he gave me. Still, he was very apprehensive about sticking his fingers close to my asshole to massage my taint. The action was causing him some distress, I could tell. He held his breath and hurried up the process. I forced a fake moan or two, as if to say, it really felt good.
“Move up to my loins and jack our cocks together,” I told him, seeing a look of shock cross his face.
“Seriously?” he asked, somewhat in a state of panic. I smiled. He shook his head.
“We need to feel the closeness of each other, Tyler. Jacking our cocks together will give us that feeling,” I explained.
“Maybe for you, but it’ll give me the creeps. This is so wrong,” He replied. I shook my head.
“Let’s stop. This isn’t for you, Tyler. Let’s quit before things really get weird. Just know it’s a deeply caring act two guys can share with one another. It’s meaningful and fulfilling. But, not if you’re not into it. You’re straight, plain and simple. I can’t replace what you need in a woman, and even though you turn me on like crazy, I can’t make you feel that special to me,” I explained. He looked disappointed. I ran my hands up and down his thighs to his groin. His cock was still flaccid.
“How did you dick get so hard?” he asked, not acknowledging my request to quit what we were doing? I chuckled.
“You, and the closeness we’re sharing. That’s how,” I replied.
“Mine’s not hard,” he replied. I told him that was rather obvious, because I wasn’t turning him on. “Josh, why don’t you just fuck me and get it over with. Your dick is hard so you can do it. Doesn’t matter if mine isn’t,” he suggested. I rolled my eyes.
“It’s not the case of just sticking my dick in your ass, Tyler. It’s the intimacy shared between the two of us. If I just fucked you right now, you’d miss all that,” I explained.
“Something tells me I need to miss all that,” Tyler replied. I pulled him down and kissed him passionately once again. In doing so, our cocks were pressed together. I could tell he was really nervous, but held him there to get used to us being together, sharing the feel of one another’s cocks up against each other. I felt a little stir in him, giving me a small sliver or hope he might actually be able to go through with this.
We finally broke the passionate kissing. “Had enough?” I asked, hoping he’d say he did. He frowned.
“Not until you give me that toe-curling, mind-bending orgasm you say comes with what we’re doing,” he replied, rather emphatically. I shook my head.
“Why put yourself through what seems to be torturous for you? Give it up, and go on with your straight life. This isn’t for you, Tyler,” I told him rather emphatically.
“It seems to be my brother’s world. I don’t want to lose him to something I don’t understand, Josh. I need to understand this for myself. Is it real or just some sort of craziness he’ll get over,” Tyler replied. I grabbed his shoulders and rolled him over on his back, then knelt between his legs and spread them apart some. I picked up his limp cock, taking his breath away, then started to massage it to try to bring it to life. “Oh shit, this is so weird,” Tyler said, but went with it. His cock was nice, even in its flaccid state. He was turning me on even more, playing with that straight limp cock of his. I fondled his balls also, getting him to moan some, but the look on his face appeared to be shear fear. I leaned in and started sucking on his balls. His whole body shook with that action. “Fuck, that’s just totally weird. How can you do that, stick another dude’s balls in your mouth?” he asked. I looked up over his cock and balls and smiled. I ran my tongue up his limp shaft and around the head of his penis. That really got him going. I was starting to feel his penis growing in my hand. This time, I went for broke and swallowed that flaccid cock of his easily taking it all the way down to the base in its flaccid state. His loins bucked and heaved some, trying to wrap his head around the fact he was getting a blowjob from a dude. “Oh fuck, this is weird,” was all he could say over and over, but his dick said he liked it, as it stiffened up with all the attention my mouth was giving him. There was no doubt about it, Tyler had one hell of a nice cock, and it was mine to play with and love at the moment.
“You okay?” I asked, as I came off his now erect cock and looked up at him.
“Hanging in there,” he replied, giving me no indication that he liked it or didn’t like it, not committing to the fact it felt damn good to him regardless of the fact, I was a dude. His dick told me the truth, which was all I needed. I began jacking his hard cock as I sucked it. His whole body was shaking. I moved my other hand over to stimulate his taint and fondle his balls, as I stroked and sucked on his dick. “Josh, you better stop or I’m not going to be responsible for what’s going to happen soon,” he warned with a sense of urgency. I stopped rather quickly, then gently stroked his penis, as if to edge him some. “Whew, that was close. Damn, that was some BJ. Okay, you do a great job there, I have to admit. Never had one that intense before. Guys do give better BJ’s than girls do. Tink said guys were way better, and I have to believe him now,” Tyler admitted, making me smile.
“Okay, you’re turn. You get to give me one,” I told him, getting a look of horror on his face.
“What the fuck, Josh? You want me to stick your cock I my mouth and do that?” he asked, almost in total shock. I smiled.
“For this to work, you have to do to me what I do to you, Tyler,” I said to his look of horror. I swear, I saw him sweat. “Or, we can quit now, and be done with this madness,” I offered. For a few seconds there, I thought he was going to throw in the towel. Then he brought me to him to kiss me passionately again, this time our hard cocks pressed together. I had to believe we were making a little bit of progress. Then he rolled me over on my back, and got between my legs, running his hands up and down my thighs, driving me half crazy in the process, my cock drooling precum. He thought I had cum. I told him that was just precum, a preview of what was to cum. He didn’t seem to understand, but I wiped it off the end of my cock with my fingers then put it in my mouth. I thought he was going to puke with that action. He shook his head in disgust. “It’s precum and it tastes good. I’d rather taste yours though. It’s more fun tasting your partner’s precum and cum,” I told him. He gave me a contorted look.
“I hate cum,” Tyler replied. “I hate having to clean it up off my dick when I take a condom off. It’s sticky and smelly. Yuk,” he said. I smiled, telling him he might learn to love it in time, if he gave it a chance. “No fucking way, Josh. Not that, ever,” he replied. I just smiled, then pointed to my raging boner, as if to say ‘get with it’.
Tyler grabbed my cock with one hand very nervously, as if it was a piece of shit and he didn’t want to touch it. “Lick my balls with your tongue first, Tyler. Run your tongue all over my balls, then work your way up my shaft and tease the glands on the underside of the head of my cock with the tip of your tongue, before you swallow it. Oh, and watch the teeth when you swallow my cock,” I told him. Tyler had a look of horror on his face. He shook his head, as if to shake off the willies. He leaned down and stuck out his tongue. He made the most contorted face I’d ever seen. “We can stop here if you like. I can finish you off with a blowjob, and we don’t have to do anything else,” I suggested. He thought very seriously about that for a few seconds. I had given him several opportunities to quit, but he was bound and determined to go ahead with all of this. Nervously, he jacked my cock a few times.
“It’s so weird feeling another dude’s cock and balls. I don’t know how you guys do this,” he said, as he jacked my cock up and down a few times. “How you can stick a dick in your mouth is beyond my comprehension,” he said, as he reluctantly bent over to try to lick my balls. “Wow, your balls are smooth and warm,” he said, as I felt the very tip of his tongue quickly swipe across them. I reminded him, it was just skin he was licking. Kissing my balls was about the same as kissing my lips. If he could kiss me on the lips and stick his tongue in my mouth, he could lick my balls and dick also. “Somehow, I sense a major difference there, but if you say so,” he replied. I felt his tongue go up my shaft. Tyler was trembling when his tongue reached the glands. His stimulation of the glands on the underside of my cock head, only made my precum flow even stronger, his tongue getting a taste of a dollop of precum that oozed from my piss slit. I thought he was going to throw up, he coughed and gagged. “I got that precum shit in my mouth, Josh. YUK!” he said shaking his head. I told him it was full of protein. That didn’t seem to impress him any. I asked him how it tasted. He honestly couldn’t tell me. I just shook my head, telling him I thought mine was sweet. I got an ES&D (Eat Shit and Die) look in response from him. I told him to take a deep breath, then wrap his lips around the head of my penis, and run them down my shaft, as I had done to him. His whole body was shaking. I pulled him back to me and kissed him passionately again, hoping to calm him down some. Then I let him go to do as I asked. I was hoping he could make this happen without him passing out or something crazy like that.
“We can stop this anytime, Tyler. We don’t have to do this,” I reminded him, giving him another out. He shook his head then put his lips on the head of my cock, making one hell of a contorted face, then put his lips on the head of my penis. “That’s it. Run your tongue around the head while it’s in your mouth. That a boy. You’re doing good. Now slide your lips down the shaft as far as you can and jack my cock at the same time. Tyler tried to do as I asked, but came off my dick gagging like crazy, and spitting. I almost laughed, but didn’t want to embarrass him. “It’s okay, Tyler. That’s a normal reaction for the first time. You did good,” I said, trying to compliment him for his efforts.
“This is so wrong,” he said shaking his head. I told him to try one more time, then I’d show him something else. Although there was more gagging and coughing, he managed to suck my cock with a minimal amount of pleasure to me, but with great mental discomfort to him.
“Congratulations, you’re now a cocksucker,” I told him, as I grabbed him to kiss him, signaling he could stop. A great relief came over his face. He was back to doing something he enjoyed, kissing.
“This is so wrong,” he said, over and over. I told him he could stop anytime. He just shook his head. “Now can you fuck me and we get this over with?” he asked. I smiled.
“We still have a little more foreplay to get to the main event,” I jested. He rolled his eyes. “I have to do most of the work on this one for you, so hopefully you won’t freak out on me,” I informed him. He looked nervous. Tyler was totally flaccid again. I reached down and stroked that beautiful dick of his, but didn’t get much response from him in doing so. He did seem more comfortable with me touching him now, than when we started, but it was still terribly strange to him to have me touch him there. I told him to get on all fours. He did as I asked, with great reservations as to what was about to happen. I got behind him, and spread his ass cheeks apart with my thumbs. Damn, if he didn’t have a beautiful hair lined virgin asshole. I played with the fine hairs that adorned his hole. “Tyler, you have a beautiful asshole, buddy. Damn, it’s sweet,” I said, as I played with his fine hairs with my fingers and thumbs.
“I wouldn’t know. I’ve never seen it, and don’t really think I want to. How can you tell me I have a beautiful asshole? I mean, who does that?” he asked, as if that was the creepiest thing he’d ever heard. I shook my head smiling, although he couldn’t see me behind him.
“Don’t go crazy on me, but I’m going to lick your asshole and stimulate it for you,” I told him.
“You’re fucking going to lick my asshole, Josh?” he asked, almost in a panic, as if that was the dirtiest most stupid thing he’d ever heard of in his life. I chuckled, then told him it was really going to feel good to him. “You’ve got to be fucking crazy, dude. Good grief, this shit you guys do is so fucked up. You guys are all fucking crazy. Licking assholes? Fuck that shit,” he said, totally creeped out. I told him to relax and enjoy it.
I started off by sucking his balls from behind, then pulled his flaccid cock back between his legs and sucked on that until I got him good and hard again. He kept telling me I was crazy, but his dick said he liked it, and liked it a lot. I even got a little precum out of him, which told me everything I needed to know, as far as whether he was enjoying this or not. I ran my tongue up over his hairy taint to his asshole, taking his breath away when I reached that virgin love portal. Tyler gasped, and his body shook from the sensation of my tongue on his hole. I tenderly licked and teased that orifice, running my tongue around the edges then over the center, getting it slicked up. Tyler’s whole body shook at the feel of my tongue on his hole. After getting it good and slick, I told him he would feel a little pressure, as I inserted a finger in his hole. He told me to be gentle. I licked my middle finger, and slowly penetrated him with it, down to my second knuckle. I even gave his prostate a little thrill, which made him jump, telling me he wasn’t sure what happened, but he felt like he wanted to cum. I told him it was all part of our ass play, and I’d hit his ‘G’ spot. He told me guys didn’t have a ‘G’ spot. I stimulated his prostate again until he acknowledged he had one alright. I chuckled, telling him he had so much to learn. I moved my finger all around trying to stretch his hole some to get ready for the main event. Normally, I preferred to train a newbie for a few days with graduated butt plugs to stretch their hole to take a dick, but this boy was determined to do it all at one time. I just hoped he could take it. I pulled out my middle finger and inserted my thumb, pushing down on the edge of his hole to stretch it some. Tyler gasped a few times, but held in there. I stopped occasionally to suck his cock and suck on his balls to keep him interested. I took my thumb out of his ass and rimmed him strongly with my tongue. Oddly enough, he was starting to enjoy the ass play I was giving him. I stretched his hole, as best I could with my thumb, then tried two fingers. I could tell Tyler was experiencing some significant discomfort with that action, but I told him to hang in there as this was prep for the main event. He held in there, anxious to get this done. I finally stopped, and let him relax some.
“Fuck, that was intense,” Tyler told me, when I let him lay back down and relax some.
“Anal intercourse is very intense, Tyler. You’re going to feel pain at first, the first time we do this, then you’ll relax some, then the pain transitions into pure pleasure. I’m not going to lie to you. It is going to hurt at the beginning, but if you can manage to get through that, the following feeling is euphoric. It’s awesome. It will blow your mind,” I assured him. Tyler hugged me and kissed me.
“Tink told me the same thing. He said it hurt like a bitch the first time, but then it was fantastic, and he can’t get enough of it after that. He said there was nothing like it ever. I can only hope it feels that good,” Tyler replied. I kissed him again, telling him he’d be fine, but I could stop at any time. He said he was ready for this.
I grabbed a bottle of lube from the drawer in the nightstand, knowing each room had a bottle of lube in it, like hotel rooms had bottles of shampoo, conditioner and body wash in them. Hey, we were a first-class resort, with free lube. You had to love it. First, I laid on top of Tyler, letting our cocks rub together again. He was becoming more comfortable with us that way, getting more used to light intimacy between the two of us. I rose up some and jacked my steel hard cock against his flaccid dick. While he still wasn’t stimulated with intimate touching of male genitalia, he wasn’t freaked out by it at least. We kissed passionately.
“We don’t have to do this, you know,” I again reminded him.
“Josh, you sucked my dick, made me suck yours, licked my asshole, then finger fucked me, thumb fucked me, shit, you might as well fuck me with that hard dick of yours. We’ve come too far to stop now,” he replied, making me smile. I kissed him again, but warned him, I hoped he wasn’t freaked out with male intercourse. He said he hoped he wouldn’t be either.
I told Tyler, I was going to lay on my back, and let him control the level of penetration for the first time, until he got comfortable with the penetration, then we might try some different positions. He looked concerned. I had him bend over, so I could play with his ass again and lube it up good. Once I lubed him up, I laid on my back and had Tyler lube up my cock. He was hesitant, but did it. I handed him a towel to wipe the lube off his hand. I positioned his ass over my cock and guided it to his hole.
“Wait, don’t we need a condom for this?” he asked, not sure he was ready to go through this.
“Have you ever fucked a girl without a condom?” I asked. He gave me a strange look.
“Hell no. I don’t take any chances with girls, not that I’ve had that many experiences with girls lately. Don’t need any pregnancies in my life for sure,” he replied.
“Well, we know you haven’t been fucked before and haven’t fucked any guys, so I’d say we’re safe. I can’t get you pregnant for sure,” I chided, Tyler giving me a weird look.
“You wouldn’t cum in my ass, would you?” he asked concerned. I smiled.
“You mean like you promise not to cum in some girl’s mouth when getting a blowjob?” I teased. He smiled, telling me I knew what he meant. “I sincerely promise not to cum in your ass, if that makes you feel better, Tyler.” He gave me a half smile, as if he wasn’t so sure.
He said it felt so weird, my dick up against his asshole. I told him to take a deep breath, try to relax and then lower himself to let my penis slide inside him. He took a deep breath then slowly lowered his ass. I could feel my cock head slide just inside him. He had a very contorted look on his face, grimacing at the pain he was sure to be feeling, even though I had loosened him up some. He slid down a fraction of an inch at a time, still grimacing at the pain. I ran my hands up and down his thighs as he continued to slid down my cock.
“Fuck, this hurts like a bitch. What the fuck is the matter with you guys, doing shit like this? You guys are fucking nuts,” he said, grimacing with pain. I told him to relax and to push, like he was taking a shit. He said he didn’t want to get shit on my dick doing that. I told him, that action would help slide me inside him. He grunted, and I slipped further inside. “Fuck, this hurts. Are you sure this is going to get better?” his contorted face asked. I told him to be patient. Suddenly, he slipped all the way down, and held his breath, holding still, not moving and not breathing. I slapped his thighs.
“Tyler, breathe.” He took a few short breaths, his eyes closed and his face contorted. Then suddenly he opened his eyes and looked down at me.
“Damn, this does feel kind of cool,” he said. “Doesn’t make any sense, and I can’t begin to explain it, but fuck, it’s not bad,” he commented, getting used to me inside him. I jacked his flaccid cock some, fondled his balls, then pulled him to me for some passionate kissing. Then I rolled him over on his back, still connected, raising his legs some to give me better access.
“You okay?” I asked. He looked up and smiled at me.
“Hell yes. Actually, I’m great,” he replied, pulling me to him to kiss me again and again. After that bit of passionate kissing, I started a shallow rhythm going. He seemed to be getting into it, as his dick came back to life below me. Adjusting to it well, I stepped up the pace. Tyler was really starting to get into it. “Fuck, this feels good, Josh. Damn, this is crazy,” he sighed, as I thrust a little harder, hearing no complaints but pleasurable moans and groans. “Oh, Josh,” he said, getting louder as his pleasure seemed to escalate. I too, was really getting into this, having a guy I crushed on, deep on my dick, sharing our bodies together. It wasn’t supposed to be like this, never supposed to happen, but here we were my cock deep in Tyler’s ass, and he seemed to be moved by our closeness. He wrapped his legs and feet around my ass, pulling me deeper inside him as he if wanted every bit of my dick he could get. This boy was horny and passionate. “Not that I ever want this to end, Josh, but I’m going to cum,” he warned, as he stiffened up. I jacked his now rigid cock, only to feel his heels dig into my ass as Tyler stiffened up, screamed out a guttural sound, as his cock exploded sending his precious cum flying over his head, then to his chin, breast and abs. I stopped thrusting, knowing I was about there, but not wanting to cum inside him and totally freak him out. Tyler was breathing heavily, still stiff as a board. “Fuck, that was awesome,” he finally managed to say as he started to relax some. I started to pull out of his ass, but he stopped me. “No, don’t leave me. Stay inside me, Josh. I need you there,” he pleaded, much to my surprise. He pulled me to him and kissed me like crazy. I could feel his warm ball jizz pressed between us. When he finally let me up again, I scooped some of his jizz up and tasted it. He made a face, as if I just ate some of his shit.
“It tastes good, Tyler. You should try it. Now I have some of you inside of me. Now, we’re really brothers,” I told him. He gave me a confused look. Since I was still rock hard inside his ass, he couldn’t move much with me still there, so I force fed him some of his own cum, as he slightly protested, but finally relented.
“Hummm, it isn’t that bad. Still, it’s the thought,” he replied. I asked him if I could back out and lay beside him. He relented, but moaned disappointedly when my hard cock slipped out of his ass. “Josh, would you fuck me again a little later?” he asked.
“That good, huh?” I teased. He smiled, then kissed me. “Was it toe-curling and mind-warping?” I had to ask.
“OMG, it was just like Tink described it. It was fantastic. I’ve never cum so hard in all my life. Please, we have to do it again,” he almost begged. I smiled, as I laid beside him with my arm around him. “I think you drained my balls for sure, but it doesn’t take me long to recover,” he informed me. “I’m good for several rounds,” he bragged, wagging his semi limp cock at me. I reached down and fondled his balls. “Fuck, even that feels good. Who’d ever think this stuff could be so fantastic?” he said rather excitedly. I told him he was quite hot in bed, telling him it was too bad he was straight. He told me not to remind him about all the crazy stuff he said about how gross he thought everything we did was, making me laugh.
“If I’m going to fuck you again, you need to fuck me first. Remember, what I do for you, you have to do for me,” I reminded him. He frowned again.
“I have to stick my cock in your ass?” he asked, skittishly. I smiled. He rolled his eyes.
I swung around, and sucked the last remnants of his semen from his cock, getting him hard in the process. Then I lubed up his cock nice and slick. I rolled over on my back, then raised my legs. “This is so fucking weird, Josh. But, since it’s you, I guess I can handle it,” he said, as he got into position. “Here goes nothing,” he said, as he lined up his rigid cock with my asshole. He was amazed at how easy I took his cock. “Fuck, you’re tight,” he exclaimed, feeling my body grip his penis and welcome him inside me. He and I both sighed as we connected together, once again. He looked deep into my eyes, as he started a rhythm going. “You’re so tight. Wow, this is actually fantastic. I never dreamed it could be like this,” he said, then leaned in and kissed me again and again. My little homophobe was starting to melt, I thought to myself. He liked this. He liked it almost too well, I began to think. Damn, if he didn’t feel great in my ass. I stepped up the passion somewhat, squeezing his ass cheeks, then rolling him over, putting me on top and in control, as I thrust my ass hard against his strong boner, intent on breeding me with a passion. I pinched his nipples, kissed him all over his face and neck, reached around and pulled on his ball sack. I squeezed his cock with my ass muscles, half driving him insane. I rolled him over on top again. We were both sweating like crazy, him desperately trying to breed me and me desperately wanting that cock of his as deep in me as possible. He warned me he was about to cum again. I told him I was right there with him. He wanted to know where he should shoot it. I told him just let loose inside me. Although I’m sure his brain couldn’t comprehend the logic in that, there was no time to rationalize anything as we both intensely stiffened up as our cocks exploded together. He fell down on top of me, his cock still in my ass. I wrapped my arms around him and held him tight. He sighed, as he rested his head on my chest and I caressed his back.
“I can’t believe I came inside you. I’ve never fucked any girl raw and let loose inside her. Wow, that was one hell of an orgasm, just letting my cock explode at will and not having to worry about it. I hope that wasn’t bad for you,” Tyler remarked. I smiled, then kissed him again, telling him I loved having him inside me. It was a little disappointing when I felt his deflating cock slide out of my ass. I actually missed him. I guess that’s what Tyler was feeling when he asked me to stay inside him. Tyler shocked me when he scooped up some of my jizz and tasted it. “Damn, Josh, you taste a lot like me,” he said sampling my sperm. I smiled, shaking my head.
We laid there together for a few moments, not saying a word. I ran my fingers through his thick wavy hair, as we looked deep into each other’s eyes. He kissed me on the tip of my nose, making me smile. Then a little tear ran down from one of his eyes. “You okay, Tyler?” I asked, as I wiped the tear from his cheek. He half smiled.
“This is too beautiful to be true, Josh. It can’t be like that. It’s just wrong,” he told me. “It’s not meant to be this wonderful,” he added.
“But it is, Tyler. I’m telling you, this is what Tink feels, only on a regular basis. Is it wrong for him to be happy this way?” I asked.
“I understand now. I think I really do. You helped me understand. If Tink feels this way, then more power to him. I can’t fault him for wanting to feel this way,” Tyler replied. “I’ll give him my blessing. I have to anyway, as I love my brother. I guess I can understand him more now than I ever did before. I’ll defend him to my death,” Tyler pledged to me. I kissed him again.
“How about a quick shower so we don’t smell like cum when we join the others?” I asked.
“Wait, I need you to fuck me again,” he pleaded, not wanting to end his opportunity. I smiled.
“Your dick has been up my ass and mine has been up yours. I don’t think you want to suck my cock after it just came out of your ass,” I reminded him. He looked disappointed somewhat. Then he told me I had a point. We got up and headed to the shower. The shower was good sized, with enough room for a foursome, if needed. To my surprise, Tyler soaped up my balls and cock for me, as I did his. We had our hands all over each other’s bodies, tugging and probing, heating ourselves up to a sexual fervor, kissing passionately and running our hands all over each other. He sunk to his knees finally, and started sucking my cock, his cock at full mast now, doing his darndest to get me rigid hard. He was definitely doing that in a big way. I finally brought him up to his feet, as my balls were starting to churn. I pressed him face first up against the shower wall, spread his feet apart, then slipped my steel hard boner up his ass. He gasped as I penetrated him, then pushed his ass back against my pelvis, wanting all the cock I could give him. I fucked him hard this time, with him telling me to fuck him harder. Tyler was slamming the wall with the palm of his hand, begging me to fuck him harder. I reached around and jerked him off, as I slammed my cock deep in his ass. I felt his body stiffen up, as my hand filled with his warm jizz, Tyler almost pinching off my cock as his exploded for the third time. That caused me to explode my second load of the night, deep in his bowels. I wrapped my arms around hm and held him tight, as I kissed him on the neck, until he turned his head so we could suck face again. My cock soon slid out of his hot ass, along with a minimal amount of my seed. Tyler turned to me and hugged me tightly, then we kissed again and again. He started to cry then, his head pressed up against mine, as he hugged me tightly, weeping like a baby.
“Are you okay?” I asked. He didn’t say a word at first, just held me tightly. I ran a hand up and down his back, over his tight ass, trying to console him. Then he finally looked me in the eyes. I wiped the tears from his face, the shower water still spraying us.
“I think I love you, Josh,” he said. I hugged him tightly.
“We love each other as brothers, Tyler. You’re fine. All of this was a dramatic new experience for you. It’ll take some time, but it will make sense in the end. I’m always here for you. You’ll be fine,” I assured him.
“Josh, what if’ I’m gay too? Is that possible?” he asked, somewhat concerned.
“Would it kill you if you were?” I asked. By the look he gave me, he wasn’t so sure. “Look, this was a totally new mind-blowing experience, you’ll probably forget in the near future. You’re straight and you like women. But that doesn’t mean you can’t love your friends also. You’re going to be fine, Tyler. You know and understand your brother better than you ever have in your life. That’s important and reassuring. You’re going to be fine. I’ll always be here for you also, and any of the rest of us you need. We’re going to be close for life,” I assured him. He hugged me tightly again. We finally finished cleaning each other up. I shampooed his hair, which made him happy. He shampooed mine in return. I turned off the water. We got out and dried each other off, taking great liberties with one another drying our man parts. He chuckled in the end. We only had our shorts to get dressed in, thinking why bother, as we were going back to naked friends anyway.
“Thanks for helping me understand, Josh. I can’t begin to tell you how much I appreciate what you did for me. I am definitely good with Tink’s decision now, and I’ll try to smooth things over with the parents when Tink wants them to know. I’m not going to tell Rod or Lonnie about Tink for awhile anyway. I’ll let him do that. It’s not my place, unless he wants me to. But, that’s up to him. Can we not tell anyone about what you and I did tonight?” he asked, kind of concerned. I smiled.
“It will always be our little secret, Tyler. Once and done, but never to be forgotten,” I chided. I got another big hug for that one.
“I do love you, you know. I could not love you after what happened here tonight. It’s impossible not to,” he replied. I gave him another hug, telling him, I guessed I’d have to love him also. He said I definitely proved that to him tonight for sure. I patted him on his tight ass, telling him we better get back or someone was going to come looking for us. He chuckled, then joked, he might want to disappear with me forever. I squeezed one of his ass cheeks for that, my finger touching his hole in the process. He told me I was about to get him hard again, and that might start things all over again. With that, I pushed him out the door, locking it behind us, making a note to have housekeeping visit it first thing in the morning, although we left it mostly clean.
We decided not to show back up with the group together, but separately. Tyler said he’d go talk to Tink anyway, telling him that I made him understand how happy Tink was, and he’d give him his blessing. I told him, I thought that would be nice. I got a little pat on my ass as we parted, giving me a little thrill. When I got back to where I left the group, Blake, and Wes were still there, drinking beer. Jake and Terry were playing water volleyball in the pool with several of the other guys. Rod had gone to the pisser. I was able to tell Wes and Blake about my discussion only with Tyler about Tink. I didn’t say anything about the sex, keeping that a secret between Tyler and me only. At some point in time, I would tell Jake, but I needed a little distance on that for a while, in case we all got drunk and our loose lips let out secrets. Blake and Wes were relieved that Tyler finally knew, and had accepted the fact Tink was gay. They asked how he took it. I laughed and joked, he took it like perfectly, right up the ass. That made them laugh, although they didn’t believe a word I said, other than Tyler was fine with everything, after he had my assurance, we would always look out for him.
It seemed everyone was pretty well oiled up tonight for some reason. I grabbed another beer myself, then we headed over to the pool to watch the guys play water volleyball. We had Auggie, Dave, Caleb, Chase, Dustin, Ethan, Trevor, Andy, with Allen, OBB, Lonnie, Dylan and Garth rotating in and out, and fetching beer for the players between sets. Wes, Blake, Rod and I were sitting by the side of the pool watching the craziness going on, as these guys attempted to play the game in a semi-drunken state. It was quite hilarious with all those naked guys in the pool together, accusing each other of molesting the other as they went for the ball, or balls, in this case. Rod was laughing his ass off. Someone actually pulled him into the pool and made him play. I noticed Tyler was back and jumped in the pool with the others. Tink came by and sat on my lap, kissed me, then told me he loved me. He thanked me profusely for helping out with Tyler.
“Josh, I’ve never felt closer to my brother than I have tonight, after you talked to him. Don’t know what you said or did, to help him understand me, but I love you for it. You were my first, and I’ll never forget that,” he told me, giving me a quick kiss. I flipped his cock around a little as he did, causing him to give me another kiss.
“Tink, Tyler loves you, buddy. You’re his brother, and you always will be. Nothing has changed in your relationship, other than this may have brought you closer together. That remains to be seen, but I think it will. You two are good now,” I assured him. Tink couldn’t have been happier.
There was a lot of screaming and commotion going on in the pool. Apparently, one side finally won the championship that had been raging on most of the evening, if there ever was an official score. Who knew? Luke, Dylan, Garth and Lonnie were lining up Solo cups of beer on the side of the pool for the guys to get another drink. The guys were still in the pool but using the apron of the pool as the bar counter. It was kind of crazy, but they were thirsty and didn’t want to get out of the water. Blake, Wes and I decided to join them in the pool. I came up from behind Jake and stuck a finger up his asshole, making him jump. He laughed, then turned around and kissed me.
“Hey, just for that, you have to kiss my asshole to apologize,” Jake joked. He hoisted himself up then laid on the apron of the pool, giving me a perfect shot at his asshole. I was still in the pool. I spread his ass cheeks, then gave his hole a swipe with my tongue. “Do it again, I didn’t feel it that much,” Jake urged, with the other guys laughing. Terry hiked himself up beside Jake, telling me, his asshole needed a kiss also. I spread his tight buns and nibbled on his asshole, giving him a boner, making him laugh. Auggie then hiked his ass up so I could lick his hole. I got a boner kissing that hot hole of his, with all the nice dark hair around it and in his ass crack. I gave him a boner also. Next was Dave, then Caleb, then Chase, like a receiving line of assholes that needed to be kissed. Hell, I had fun kissing and licking all of those chlorine smelling assholes. I finally made my way to the end of the line, not even realizing who was who anymore. The last guy moaned and groaned like crazy. When he finally stood up, it was Rod, shocking me.
Damn, you give nice rim jobs, Josh,” he said rubbing his ass. “I always wanted to know what that felt like, and now I do. Thank you. You’re a true friend,” he said smiling.
“Rod, you crazy ass. I can’t believe you just did that,” I said, shaking my head. He laughed, as did the rest of the guys. “So, you coming over to our team now that your ass has been violated with a dude’s tongue?” I chided. He rolled his eyes.
“Nah, you’re going to have to fuck me first. If we stay much longer, I’m not sure that might not happen,” he chided. Dave and Caleb picked Rod up and threw him in the pool. Rod scrambled furiously to try to get out, as I told him I was going to catch him and fuck him good. It was one crazy night for sure, but with so many wonderful, loving friends. We only had one day left before returning to the real world.
I think leaving the Pink Flamingo after Spring Break will be the hardest thing to do both for them and for us. 
) But then Josh fucking him was a major revelation, an act he'll never forget. I really don't know what to think about Tyler now. 
and 
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