Posted on literotica at Randall Pt. 01 - Gay Male - Literotica.com. Let me know if you want me to continue to the next parts.
Let me tell you the story of how I completely lost my manhood to my best friend.
I'll set the scene a little. Randall was my best friend for over 7 years. We met in college, and bonded quickly. We've shared a lot of adventures and good times over the years, and even though we live in different cities, we do a good job keeping in touch. I'm not gonna lie, we are both pretty attractive guys. Randall's taller than me, at 5'11 (I'm only 5'8), but I make up for it with a pretty chiseled body. He's not out of shape by any means, but he leans a bit more towards the dad-bod side of things. I'm gay, and Randall's straight, but that never really came between us. We both have had our fair share of partners over the years, and even though I objectively think he's attractive, I was never really into him, thankfully, so that didn't come in between our relationship.
The problems started, really, because of the fact that I'm sort of a size queen when it comes to dick. I go crazy for it. I love a big, floppy cock, the bigger the better. I feel like I always have - I'm mesmerized by big dicks in porn, and I seek it out in my sexual partners. My obsession began to veer towards insecurity, and combined with a kink for humiliation, I found myself more and more in the online world of small penis humiliation. I couldn't get enough of it - I loved guys being made fun of for being underhung, especially when the owner of that humiliation was a man with a much bigger dick. I can't tell you the hours I've spent looking up porn of this kind, and I started wading into it in my personal life as well, getting guys to brag about their cock size, and maybe teasing me for being smaller than them.
Now we get into the anatomical details. My dick measures at right around 6 inches when I'm hard. That's not necessarily "small" by any means -- of course, it's not really huge either, nothing to really brag about or tell your friends after a hookup, but a pretty respectable, average size. For most of my life, I've been pretty proud of my dick. It's pretty aesthetically pleasing, it gets the job done, and it's obviously brought me a lot of pleasure. But as I sought out small penis humiliation, I realized I needed a really big dick to put me in my place, and make the size difference meaningful. I needed to be with guys at least 7 inches, but preferably 7.5, 8 inches, and up would really get me going. Seeing how their dicks dwarfed mine absolutely drove me crazy. I would want to take pictures to compare, measure them with rulers, fantasize about all sorts of ways in which we could play up the difference between our cocks.
Now let's get back to Randall. Probably a few years went by in our friendship before I even thought one time about Randall's dick, or anything sexual about him. The problem came when we went to the pool at our college together, and I found out that we would have to shower together, in a big open locker room, after class ended. I didn't really know how to feel about that - I was both excited, and nervous. A part of me did want to see my friend naked, both because of natural curiosity, but also because I'm just attracted to men, and like a locker room setting like a lot of other guys do. I tried to play it cool, but I think the occasion became too much for me. We went in the locker room, and stripped off our suits. I couldn't help but glance straight at it. Randall's cock was fully soft, but it was really nice, thick, hanging down with a pretty sizable head. It must have been 4 or 5 inches soft, and all-in-all just a gorgeous cock. I tried to look away and put my mind elsewhere, but as I got under the shower, I could feel the blood rushing to my own member. Within a minute, I was fully hard, as I tried to angle my body away so nobody would see. I quickly grabbed a towel to cover myself up, dried myself off quickly ran out of the locker room. I'm not sure if Randall saw me, but I felt I had avoided any sort of awkward interaction, at least for now.
Ever since that moment, the thought of Randall's cock visited my mind every once in a while. It wasn't constant, but I realized maybe he liked showing it off to me, and had a little bit of an exhibitionist side to him. I began to notice little comments he made about nudity or dick size. He would make bro-y comments like, let's go to the bathroom together and cross streams. He would make dick size jokes when somebody brought up a measurement in inches. One time I told him what a Prince Albert piercing was and showed him the Wikipedia article (which had a sample picture). His one comment was, wow, isn't that kinda small? (That one stuck with me for a while). One time, years later, when I was staying at his house, he came out with just a towel around his waist, and lounged around for a while. It felt like he was winking at me a little, like, "wouldn't you like to see what's under here? I remember you liked it last time..."
With all these subliminal messages, I became more and more curious about how big his dick really was, as the flaccid image I had in my head gradually faded away. I'm not proud of it, but I played out scenarios in my head of how I could get him to reveal himself for me. One day, I was really horny after not relieving myself in a few days, and I came up with a plan. During one of our phone calls, I planted the seed. We have a pretty open line of communication, and I was telling him about a guy I had just hooked up with. I said something which I hoped would trigger him, along the lines of, yeah he had a pretty big cock, around 6.5 inches. As I had fantasized, that piqued his interest a little. "Oh?" He said. "I guess I don't really have a good frame of reference for what's considered big or not. What would you say?" I knew this was my chance. Vulnerability leads to reciprocation, so I just blurted it out - "oh, well to be fully honest with you, my dick's right around 6 inches. It's pretty average. I kinda just like to be guys that are a little bigger with me, if possible." He took the bait, and we launched into a full discussion about cock size. I think he was just curious as a straight guy, having not seen many in his life. I told him that most cocks were in the range of 5-7 inches anyways, that I didn't think there was that much correlation with height, that it maybe doesn't matter for some people, but I kinda like a bit of size, makes it more fun to play with. After a bit of silence, he finally said, "OK, I mean out of fairness, I can tell you my size, mine's 7.5 inches". A ton of emotions ran through my head - first of all, pure horniness, as I discovered my best friend was packing some real meat. But I was so deeply satisfied. I loved the fact that he was bigger than the range of what I told him was more-or-less normal. I loved that he had measured it prior to our conversation and sounded a little proud of it. But maybe most of all, it turned me on so much to know that he was a nice amount bigger than me, and we both knew it.
I swallowed a little bit before I managed to get out some words: "yeah, man, damn that's pretty big, good for you." In my horniness, I tried to keep going for the gold: "you know, I almost don't believe you... that's like a pretty big dick... have you ever by chance taken any pictures you'd be willing to share?" He laughed a little, but said he probably wouldn't be comfortable sharing pictures like that. I understood, and felt a little embarrassed from bringing it up. We shot the shit a little bit more, but eventually hung up. I furiously jerked off after the end of the conversation, imagining my friend's big dick in my mind for the first time.
I thought maybe the story would have ended there. But it was in fact just getting started. The next stage of the story picks up months later. I had cooled off from our phone call, and Randall came to visit me at my apartment. We had gone out to a bar, and had a couple drinks. When we got back home, he said he had a bit of a headache, and asked if I had any Advil. I led him into my bedroom, where I have all my medical stuff in my bedside drawer. I opened it up and started rummaging. I didn't realize he was standing right behind me, and had a full view of the whole drawer, which had all my sex materials too - condoms, lube, and... a big 8-inch dildo. "Woah," he said, "what's this? Damn man I see what you spend your time doing now..." I blushed a little but didn't say much. "Yeah, I don't use it much, but bought it on an impulse haha." "OK OK," he said, "I mean, no shame at all, I'm sex positive, you know that." "Honestly, I'm just impressed... isn't this thing pretty big? Like is this a representative dick that you would... you know... be fucked by? Sorry for the crudeness," he blushed. "Oh," I said, "I mean not really, it's a bit of a fantasy... just to train myself, you know?" He paused a little. "Yeah, you know, I've been thinking about it since we had that phone conversation a few months ago... I know I didn't want to show you a picture, but if we're in person, I honestly have no problem with it". I froze. "You mean... "I gestured towards his crotch vaguely, "just show me?" "Sure," he said, "I mean I'm kinda curious how I compare to this thing, ya know? I think it has me beat by a little." I was a little shell-shocked. Was my best friend really about to voluntarily show me his cock? What was going on?
I somehow blurted out some words about how that would be cool with me, and I wouldn't tell anybody if he didn't want. I honestly couldn't remember what he said next. All I remember is that he started undoing his belt, and sliding his jeans off. He started playing with his member through his boxers. I could already see a pretty sizable bulge, and he swung it back and forth with some serious force. He put his hand in there and started tugging, still covered by the boxers, but low enough that I could see the top of his pubes and the base of his shaft. It looked even thicker than I remember. Finally, he stopped tugging, and snapped the elastic back so his boxers were fully on, albeit a ridiculous tent formed at the front. "So whattya say, you ready?" He said with a grin, as his fingers were positioned at the sides of his hips, ready for big reveal. I couldn't do much but nod, and very quietly admit, "yeah, I'm ready". He then confidently grinned even wider, swiftly brought his boxers down in one big motion, and allowed his massive cock to spring up at full mast, pointing out at me and my dropped jaw. It was even better than I could imagine. Cut with an enormous head, beautiful smooth shaft with just one vein running along the side to add a bit of character. It felt like I paused for a long time before I said or did anything. It's pretty embarrassing, but I honestly followed my instincts. I got off the bed and moved slowly closer, looking at him for confirmation. He just continued to smile and look down, so I got closer and closer, and got on my knees. I looked up at him, and he smiled back. So I put his cock in my mouth, and felt like I was in absolute bliss. The next 30 minutes are an absolute blur. I sucked his dick with more passion than I ever have before. I kissed and licked him all over, always returning to the cock-head and trying to please him like there was no tomorrow. Finally, I let him cum all over my face as I jerked my cock, and let out one of the biggest loads of my life.
"Wow," he finally said, "you came a lot. I'm surprised!" "Why are you surprised?" I shot back. Oh, I don't know, I guess that's my first time, I thought maybe the amount of cum would be proportional to the size of the dick? I guess that's a pretty unfounded thought, so maybe not haha" The way he said it was very innocent, and I don't think he meant to offend, but that comment brought my dick to life again. It really turned me on that he was implying my cock was smaller or lesser than his, and I had to seize the moment. "Oh..." I said. "Yeah I guess your dick is a bit bigger than mine, huh?" Randall looked a little taken aback, and clearly didn't want to say the wrong thing: "oh, I mean, yeah, it's a bit bigger, but yours looks really solid man, I think I'm just blessed, but you have nothing to worry about." "No no," I shot back. I paused a moment, and whispered, "I kinda like that." You can say more things like that, it kinda turns me on." He looked a bit surprised. "Like what? You want me to tell you that my dick is bigger than yours? Why?" "Yeah, I mean, you can tell me that my dick is small if you want... I mean, trust me, it turns me on. I just like hearing a big guy like you brag about it, and tease me for being smaller, ya know?"
He paused, but seemed to understand at least a little bit better. "So... you like hearing that your dick is small?" "Yesss," I panted, as I started to stroke myself again. "Tell me how small I am, tell me how big you are..." "Hmm OK... I guess my cock is pretty big, you like that huh? This massive thing? Much bigger than yours huh?" "YESS," I said, "soo much bigger, I honestly feel like a little kid next to you." "Woah," he said, and looked like he might stop for a bit, but then he grinned and dove right back in, "I guess it is a little bit of a boycock... I think my dick was bigger when I was 15 honestly." I started jerking off furiously and breathing so hard, "FUCK," I burst out, "yes keep going". "Wow dude, are you sure this is OK? I don't wanna go past any limit" "No no no, keep going, be as brutal as you want!" "Wow," he said, "I guess I know why you really liked this big cock huh? You wish you had one this big yourself instead of your little boycock?" At that, he reached down and smacked my dick around. I instantly came, shooting a huge burst of cum at just him touching my cock-head. "JESUS!" He exclaimed, "wow that was fast... you're really into that, huh"
I nodded in complete pleasure. I knew a great adventure was about to begin.
Let me tell you the story of how I completely lost my manhood to my best friend.
I'll set the scene a little. Randall was my best friend for over 7 years. We met in college, and bonded quickly. We've shared a lot of adventures and good times over the years, and even though we live in different cities, we do a good job keeping in touch. I'm not gonna lie, we are both pretty attractive guys. Randall's taller than me, at 5'11 (I'm only 5'8), but I make up for it with a pretty chiseled body. He's not out of shape by any means, but he leans a bit more towards the dad-bod side of things. I'm gay, and Randall's straight, but that never really came between us. We both have had our fair share of partners over the years, and even though I objectively think he's attractive, I was never really into him, thankfully, so that didn't come in between our relationship.
The problems started, really, because of the fact that I'm sort of a size queen when it comes to dick. I go crazy for it. I love a big, floppy cock, the bigger the better. I feel like I always have - I'm mesmerized by big dicks in porn, and I seek it out in my sexual partners. My obsession began to veer towards insecurity, and combined with a kink for humiliation, I found myself more and more in the online world of small penis humiliation. I couldn't get enough of it - I loved guys being made fun of for being underhung, especially when the owner of that humiliation was a man with a much bigger dick. I can't tell you the hours I've spent looking up porn of this kind, and I started wading into it in my personal life as well, getting guys to brag about their cock size, and maybe teasing me for being smaller than them.
Now we get into the anatomical details. My dick measures at right around 6 inches when I'm hard. That's not necessarily "small" by any means -- of course, it's not really huge either, nothing to really brag about or tell your friends after a hookup, but a pretty respectable, average size. For most of my life, I've been pretty proud of my dick. It's pretty aesthetically pleasing, it gets the job done, and it's obviously brought me a lot of pleasure. But as I sought out small penis humiliation, I realized I needed a really big dick to put me in my place, and make the size difference meaningful. I needed to be with guys at least 7 inches, but preferably 7.5, 8 inches, and up would really get me going. Seeing how their dicks dwarfed mine absolutely drove me crazy. I would want to take pictures to compare, measure them with rulers, fantasize about all sorts of ways in which we could play up the difference between our cocks.
Now let's get back to Randall. Probably a few years went by in our friendship before I even thought one time about Randall's dick, or anything sexual about him. The problem came when we went to the pool at our college together, and I found out that we would have to shower together, in a big open locker room, after class ended. I didn't really know how to feel about that - I was both excited, and nervous. A part of me did want to see my friend naked, both because of natural curiosity, but also because I'm just attracted to men, and like a locker room setting like a lot of other guys do. I tried to play it cool, but I think the occasion became too much for me. We went in the locker room, and stripped off our suits. I couldn't help but glance straight at it. Randall's cock was fully soft, but it was really nice, thick, hanging down with a pretty sizable head. It must have been 4 or 5 inches soft, and all-in-all just a gorgeous cock. I tried to look away and put my mind elsewhere, but as I got under the shower, I could feel the blood rushing to my own member. Within a minute, I was fully hard, as I tried to angle my body away so nobody would see. I quickly grabbed a towel to cover myself up, dried myself off quickly ran out of the locker room. I'm not sure if Randall saw me, but I felt I had avoided any sort of awkward interaction, at least for now.
Ever since that moment, the thought of Randall's cock visited my mind every once in a while. It wasn't constant, but I realized maybe he liked showing it off to me, and had a little bit of an exhibitionist side to him. I began to notice little comments he made about nudity or dick size. He would make bro-y comments like, let's go to the bathroom together and cross streams. He would make dick size jokes when somebody brought up a measurement in inches. One time I told him what a Prince Albert piercing was and showed him the Wikipedia article (which had a sample picture). His one comment was, wow, isn't that kinda small? (That one stuck with me for a while). One time, years later, when I was staying at his house, he came out with just a towel around his waist, and lounged around for a while. It felt like he was winking at me a little, like, "wouldn't you like to see what's under here? I remember you liked it last time..."
With all these subliminal messages, I became more and more curious about how big his dick really was, as the flaccid image I had in my head gradually faded away. I'm not proud of it, but I played out scenarios in my head of how I could get him to reveal himself for me. One day, I was really horny after not relieving myself in a few days, and I came up with a plan. During one of our phone calls, I planted the seed. We have a pretty open line of communication, and I was telling him about a guy I had just hooked up with. I said something which I hoped would trigger him, along the lines of, yeah he had a pretty big cock, around 6.5 inches. As I had fantasized, that piqued his interest a little. "Oh?" He said. "I guess I don't really have a good frame of reference for what's considered big or not. What would you say?" I knew this was my chance. Vulnerability leads to reciprocation, so I just blurted it out - "oh, well to be fully honest with you, my dick's right around 6 inches. It's pretty average. I kinda just like to be guys that are a little bigger with me, if possible." He took the bait, and we launched into a full discussion about cock size. I think he was just curious as a straight guy, having not seen many in his life. I told him that most cocks were in the range of 5-7 inches anyways, that I didn't think there was that much correlation with height, that it maybe doesn't matter for some people, but I kinda like a bit of size, makes it more fun to play with. After a bit of silence, he finally said, "OK, I mean out of fairness, I can tell you my size, mine's 7.5 inches". A ton of emotions ran through my head - first of all, pure horniness, as I discovered my best friend was packing some real meat. But I was so deeply satisfied. I loved the fact that he was bigger than the range of what I told him was more-or-less normal. I loved that he had measured it prior to our conversation and sounded a little proud of it. But maybe most of all, it turned me on so much to know that he was a nice amount bigger than me, and we both knew it.
I swallowed a little bit before I managed to get out some words: "yeah, man, damn that's pretty big, good for you." In my horniness, I tried to keep going for the gold: "you know, I almost don't believe you... that's like a pretty big dick... have you ever by chance taken any pictures you'd be willing to share?" He laughed a little, but said he probably wouldn't be comfortable sharing pictures like that. I understood, and felt a little embarrassed from bringing it up. We shot the shit a little bit more, but eventually hung up. I furiously jerked off after the end of the conversation, imagining my friend's big dick in my mind for the first time.
I thought maybe the story would have ended there. But it was in fact just getting started. The next stage of the story picks up months later. I had cooled off from our phone call, and Randall came to visit me at my apartment. We had gone out to a bar, and had a couple drinks. When we got back home, he said he had a bit of a headache, and asked if I had any Advil. I led him into my bedroom, where I have all my medical stuff in my bedside drawer. I opened it up and started rummaging. I didn't realize he was standing right behind me, and had a full view of the whole drawer, which had all my sex materials too - condoms, lube, and... a big 8-inch dildo. "Woah," he said, "what's this? Damn man I see what you spend your time doing now..." I blushed a little but didn't say much. "Yeah, I don't use it much, but bought it on an impulse haha." "OK OK," he said, "I mean, no shame at all, I'm sex positive, you know that." "Honestly, I'm just impressed... isn't this thing pretty big? Like is this a representative dick that you would... you know... be fucked by? Sorry for the crudeness," he blushed. "Oh," I said, "I mean not really, it's a bit of a fantasy... just to train myself, you know?" He paused a little. "Yeah, you know, I've been thinking about it since we had that phone conversation a few months ago... I know I didn't want to show you a picture, but if we're in person, I honestly have no problem with it". I froze. "You mean... "I gestured towards his crotch vaguely, "just show me?" "Sure," he said, "I mean I'm kinda curious how I compare to this thing, ya know? I think it has me beat by a little." I was a little shell-shocked. Was my best friend really about to voluntarily show me his cock? What was going on?
I somehow blurted out some words about how that would be cool with me, and I wouldn't tell anybody if he didn't want. I honestly couldn't remember what he said next. All I remember is that he started undoing his belt, and sliding his jeans off. He started playing with his member through his boxers. I could already see a pretty sizable bulge, and he swung it back and forth with some serious force. He put his hand in there and started tugging, still covered by the boxers, but low enough that I could see the top of his pubes and the base of his shaft. It looked even thicker than I remember. Finally, he stopped tugging, and snapped the elastic back so his boxers were fully on, albeit a ridiculous tent formed at the front. "So whattya say, you ready?" He said with a grin, as his fingers were positioned at the sides of his hips, ready for big reveal. I couldn't do much but nod, and very quietly admit, "yeah, I'm ready". He then confidently grinned even wider, swiftly brought his boxers down in one big motion, and allowed his massive cock to spring up at full mast, pointing out at me and my dropped jaw. It was even better than I could imagine. Cut with an enormous head, beautiful smooth shaft with just one vein running along the side to add a bit of character. It felt like I paused for a long time before I said or did anything. It's pretty embarrassing, but I honestly followed my instincts. I got off the bed and moved slowly closer, looking at him for confirmation. He just continued to smile and look down, so I got closer and closer, and got on my knees. I looked up at him, and he smiled back. So I put his cock in my mouth, and felt like I was in absolute bliss. The next 30 minutes are an absolute blur. I sucked his dick with more passion than I ever have before. I kissed and licked him all over, always returning to the cock-head and trying to please him like there was no tomorrow. Finally, I let him cum all over my face as I jerked my cock, and let out one of the biggest loads of my life.
"Wow," he finally said, "you came a lot. I'm surprised!" "Why are you surprised?" I shot back. Oh, I don't know, I guess that's my first time, I thought maybe the amount of cum would be proportional to the size of the dick? I guess that's a pretty unfounded thought, so maybe not haha" The way he said it was very innocent, and I don't think he meant to offend, but that comment brought my dick to life again. It really turned me on that he was implying my cock was smaller or lesser than his, and I had to seize the moment. "Oh..." I said. "Yeah I guess your dick is a bit bigger than mine, huh?" Randall looked a little taken aback, and clearly didn't want to say the wrong thing: "oh, I mean, yeah, it's a bit bigger, but yours looks really solid man, I think I'm just blessed, but you have nothing to worry about." "No no," I shot back. I paused a moment, and whispered, "I kinda like that." You can say more things like that, it kinda turns me on." He looked a bit surprised. "Like what? You want me to tell you that my dick is bigger than yours? Why?" "Yeah, I mean, you can tell me that my dick is small if you want... I mean, trust me, it turns me on. I just like hearing a big guy like you brag about it, and tease me for being smaller, ya know?"
He paused, but seemed to understand at least a little bit better. "So... you like hearing that your dick is small?" "Yesss," I panted, as I started to stroke myself again. "Tell me how small I am, tell me how big you are..." "Hmm OK... I guess my cock is pretty big, you like that huh? This massive thing? Much bigger than yours huh?" "YESS," I said, "soo much bigger, I honestly feel like a little kid next to you." "Woah," he said, and looked like he might stop for a bit, but then he grinned and dove right back in, "I guess it is a little bit of a boycock... I think my dick was bigger when I was 15 honestly." I started jerking off furiously and breathing so hard, "FUCK," I burst out, "yes keep going". "Wow dude, are you sure this is OK? I don't wanna go past any limit" "No no no, keep going, be as brutal as you want!" "Wow," he said, "I guess I know why you really liked this big cock huh? You wish you had one this big yourself instead of your little boycock?" At that, he reached down and smacked my dick around. I instantly came, shooting a huge burst of cum at just him touching my cock-head. "JESUS!" He exclaimed, "wow that was fast... you're really into that, huh"
I nodded in complete pleasure. I knew a great adventure was about to begin.