My buddy Colin is one of those guys who parties too hard, drinks too much, and is always up for a dare. We met at College when we were freshmen. He was on the Football team, and I played baseball. The one thing everyone knew about Colin was that Colin had a big dick. Everyone knew this because Colin couldn’t keep his dick in his pants in almost any situation. The 1st time ever meeting Colin, I had an unplanned and unexpected close encounter with his big fat dick.
Some of the guys from the Football and Baseball teams were partying and affirming their place in society as big dumb jocks. This included doing ridiculous things to see who could be the most ridiculous at a stupid frat party. I don’t remember exactly how I ended up participating, but my buddies from the baseball team recruited me and insisted I participate. I’m usually up for some shenanigans, so I didn’t protest too much.
Somehow, I ended up being partnered with Colin, whom I knew by reputation but had never actually met. Once we were together, we had less than a minute to get acquainted, and I still had no idea what I was in for. It was too late to escape, and I found myself face down on the ground. Wheelbarrow racing was what I had gotten myself into. Suddenly, I was off the ground, supporting myself with my hands. Colin was behind me, between my legs, and lifting me from my thighs. Usually, the other person holds your ankles, but to make it as awkward as possible, It had been decided that you had to hold the other person up by their thighs.
There were eight teams, all lined up, me on the ground, and Colin behind me. Once I heard the starting gun go off, the competitor in me took over, and I was determined to win. The distance we had to travel was absurd, but Colin looked strong, and he was doing most of the work. I just needed to keep moving forward. Winning is what I'm all about, and I was determined to win. That was all I could focus on. I couldn’t have known that Colin's cock and balls were out for all to see and basically bouncing off my glutes. Everyone watching was laughing hysterically, and I was none the wiser. Colin and I won the race, and when he dropped my legs, I turned to congratulate him on the win, only to see Colin standing above me with his cock and balls. That’s when I realized why everyone was laughing. Colin's cock and balls bouncing off my ass as we raced must have looked hysterical.
Anyone else might have been angry or embarrassed. Not me, though. I was more upset that I was oblivious to Colin's massive schlong bouncing off my ass. Topping it off, Colin seemed annoyed that I wasn’t remotely upset by it. Obviously, he was doing it to get some kind of reaction from me and a response from the other partygoers. Mine just wasn’t the reaction he was hoping for. I think my nonreaction made him curious about me.
I spent the rest of that evening partying with Colin, getting to know him. He came across like a super-friendly guy, but it was plainly evident that he really craved attention. He must have had his cock out at least 10 more times that evening. I certainly didn’t mind, but I found it a peculiar way to get people's attention. Colin's big schlong was already legendary all over campus, and no one seemed bothered by it. It was almost expected of him.
I’m not sure what connected us, but Colin and I started hanging out regularly. I was drawn to him, and not only because his cock was large and legendary. We had a lot more in common than I first thought, and we became fast friends. Sports were essential to both of us, and we spent a great deal of time watching games or participating in various non-team athletic events on or off campus. We would hit the bars and play beach volleyball whenever we could. We both sucked at it, but we had a lot of fun, and it was nice to have a friend to be silly with.
Colin is slightly taller than I am at 6'3 "and has about 25 pounds on me. His light brown hair complemented his green eyes, and it was always meticulous. I, on the other hand, kept my blond hair cropped close. Hair is something I just don’t care about. I was pretty fit at about 185, and I would joke with him and say the 25lb weight difference between us was mostly all cock, but he was in excellent shape for Football. He couldn’t say anything back to me about my cock, because mine wasn’t readily available for immediate display. He did try to get me to partake in his foolishness, but I preferred getting a long, hard look at his cock, which was out of his pants, probably far too much for anyone else, just not for me.
We’d been friends for a couple of months, and I was enjoying our time together and our new friendship. Colin and I were out for Pizza and Beer, and I felt we were good enough friends that I could ask him some personal questions. “Why are you always showing off your cock, Colin?”. He looked a little bit surprised, but didn’t hesitate to answer. “It’s just something I’ve always done. Back in High school, the guys on the Football team were not shy about talking about my cock. I didn’t think it was anything special, but that’s when I noticed mine was much bigger than almost everyone's on the team. You know how it is in High School. Someone spilled the beans, and pretty soon, everyone in school knew I had a big one. At some stupid party, I was dared to pull it out and show everyone. I didn’t want to disappoint my friends, so I dropped my shorts and let everyone there get a good look. There was a lot of cheering and applause. I wasn’t embarrassed at all, and it seemed like everyone approved. I guess I saw it as a way to fit in.”
Don’t you get tired of showing it off? I mean, you’ve got a big cock, but do you think everyone needs to have a look at it? I asked. Colin thought about his answer, then said. “I’m not a gifted athlete; I’m a decent player, but I won’t be playing football after college. My GPA is 3.5, so I’m not the most academically accomplished student on campus. The one thing that is special about me is my Big Cock. It gets me invited to parties, and people are generally friendly towards me. I don’t think I would have half the friends I have now if it weren’t for my cock.
“I have to disagree with you, Colin. We’ve gotten to know one another pretty well over the last 2 semesters, and you’ve got a lot more going for you than just your cock. You’re actually quite an interesting guy, and smart too,” I said. I wanted to be supportive of his other attributes, but I did enjoy seeing his cock, and I was a bit fascinated by it as well. I’m not gonna lie. I was attracted to Colin and wanted to see his cock in a much different way than I’d seen it before, but I could never tell him that. I think in a way, I wanted others to see his cock less, and for me to see it more. The thing is, Colin and I rarely talked about sexual things, and I had no clue how he would react if I confessed to being attracted to him. I’ve had countless raunchy and vulgar conversations with all my baseball buddies, but never with Colin. Tonight I wanted that to change.
“Let's head to my place and catch the Nuggets game,” I said. “Hell yeah” was Colin's response. We had watched a lot of sports over at my place so this wasn’t something new or odd. I wanted to know more personal things about Colin, and if things go my way, maybe I’ll get to do more with that cock of his than just stare at it with longing and desire. My mouth was watering just thinking about it.
After a few more beers, the liquid courage I needed was kicking in. It was time to be brave. “Colin, do you want to see my cock? I’ve seen your cock countless times, but you’ve never asked to see mine”. The look on Colin's face was priceless, and I waited for him to respond. “Now that’s a 1st. Everyone asks to see my cock, but never once has anyone ever offered to show me theirs. I figure it was an 'I can’t compete' thing. Ok, Dave. You can show me your cock. I would definitely like to see it.”
I couldn’t believe this was happening, and I was even more shocked when he said yes. I had prepared myself for a “No” answer, but Colin is always full of surprises. I stood up, took off my jeans, and then hesitated for a bit. The excitement of this moment had blood rushing to my cock, and I was almost fully hard. My cock couldn’t compete with Colin’s, but it was above average, and I liked it. Fuck it, I thought, and I let my boxer briefs fall to the floor.
I presented my hard cock to Colin like it was the next item up for bid on the PRICE IS RIGHT. “You’ve got a fucking hard-on, dude,” was all I heard. But it wasn’t said in disgust. It took another moment before Colin said anything else. I was just standing there like an idiot with my hard cock pointed at him. “Not as big as me, but you’ve got some length and girth,” Colin said. A part of me was embarrassed entirely, yet encouraged by his comments. I’d gotten this far and was not going to stop here. “Glad you approve,” I said, as I stood there with my hard cock out, feeling exposed but not uncomfortable.
This is going well, I thought. Let's see how far we can take this. “I’ve seen your cock quite a bit, but I’ve never seen your cock hard, Colin. Can you even get that thing hard”? I asked. Without missing a beat, Colin stood up and released the cock from his pants. “You think it's big like this? Just wait. “Colin stood before me and started to stroke his cock. I had fantasized about this far too many times, and there he was, only a few feet away from me, stroking his cock to get hard.
Colin took his massive cock with both hands, stroking very deliberately. Within a few moments, I couldn’t believe my eyes. His cock had extended to at least three more inches in length, and the girth was fucking unreal. I’d honestly never seen a cock so big. I was like a moth drawn to a flame, and I walked to within inches of Colin's cock. Colin didn’t back away; he just stood there holding his cock at the base. I looked down at his cock as it stared up at me, then looked Colin right in the eye. I wanted to hold it, and I think Colin knew it. “It's ok, Dave. You can hold it if you'd like. I get the same reaction a lot.” I couldn’t believe my ears. Did he just say I could hold it?
I reached out slowly, then took his cock into my hand. I didn’t know what to expect, but it was a lot heavier than I could have imagined. I’ve seen and handled a lot of cocks in my day, and this was by far the largest and the most attractive. Despite its size, both length and girth, it was smooth, very stiff, and hefty. Oh, the things that were running through my head. I held it with both my hands, then ran the length of it with my palm. It was a thing of beauty. “Ok, Dave. you can stop now,” Colin said. I had to quickly snap out of the hypnotic state I’d put myself in. “God Damn, Colin. Sorry. I didn’t mean to get carried away like that. It’s just so fucking BIG!”
We were still standing very close to one another, and it suddenly felt really awkward. I did the first thing that came to mind. I grabbed Colin's hand and placed it on my cock. “I held yours, so you’ve got to hold mine,” I said. Colin didn’t resist. Colin doesn’t shy away from anything. He didn’t even seem bothered that I held his cock with both my hands and rubbed it up and down like I was polishing the silver. “Nice cock, Dave. Are we done? He asked. Oh my gosh, talk about embarrassing.
We put our pants back on and resumed watching the game as if nothing had happened. For Colin, it was exactly like nothing happened, but for me, it was mind-blowing. I just held the super hard, super fat, and super long cock of my good buddy, and I was the only one feeling awkward. Colin didn’t seem phased at all.
The game was incredible, and when it ended, we were hyped. The Nuggets had won convincingly, and the mood was energetic. We were both feeling good about the game, but my mind was still focused on Colin’s cock. I was obsessed and had to know more about Colin and Colin’s sex life. I grabbed two more beers from the fridge, desperately seeking an additional infusion of liquid courage. I handed the beer to Colin, and we toasted the Nuggets' win. After consuming half my beer in one gulp, I once again found my liquid courage.
“Colin, you’re like my only buddy I don’t talk about sex with. Why do you think that is? Colin was quiet for a moment, then finally spoke. “To be completely honest, I really don’t have much to say on the matter. My sex life is almost nonexistent. My cock has been a blessing and a curse. Once a girl really sees it like you did tonight, it's game over. I’m not a virgin, but no girl wants to go a 2nd round with me after they’ve experienced my cock. I know I have to be gentle, and I think I always am, but they always complain about my size and say it's uncomfortable. That’s just no fun. I don’t want to be gentle and slip the tip of my cock in and out. I want to fuck like everyone else. My cock is built for fucking. A woman can push a baby out of their cooch, but my cock is too big?. I just don’t get it.
I paused to take in what he’d just confessed and suddenly felt really bad “I had no idea, buddy. That must be frustrating. I don’t have problems like that. I’m above average, but have nowhere near what you have to offer”. What about blow jobs? I asked. Colin just shook his head. Girls just can’t seem to handle it. It’s almost comical. The last time I had sex, I jerked myself off while I ate the girl out. She wasn’t gonna let me fuck her, and she couldn’t get her mouth around my cock, I got her off, and I got myself off, so it was still a win, but it doesn’t take the place of fucking.
At that point, all I could think about was Colin’s cock in my mouth. I had to find a way. Maybe if I presented it as a dare, he would let me suck him off. I’ve sucked some pretty large cocks in my day, none as big as his, but I have skills, and I just know I can get him off. “Colin, you’re always up for a dare, much more than I am, but think about this. You can’t get a girl to suck you off, but what about a dude?. I’ve had a few experiences with guys since I started college. I’m all about new things and experiences. I want to try to suck your cock. I’m throwing down the gauntlet and daring you to let me suck your cock. If I can’t make you cum, I’ll live with the shame of defeat. If I can make you cum, you have to stop showing your cock to the whole fucking world. What do you say?
Colin looked intrigued but also confused. “Dave, are you gay and just trying to suck my cock?. “No, Colin,” That’s not it at all. I just feel bad for you, and I’m not “anything” really. I like to think of myself as an opportunist, but I won’t adhere to any label. I’m all about solutions to people's problems. After listening to your story, I’m confident I can give you a better blow job than any female who barely tried and failed.”
Colin looked like he had an answer, then excused himself to pee. I was in a nervous panic. I just offered to suck off my friend, and over the past 2 semesters, we’d barely ever talked about sex. Now we’ve held each other's cocks. I just propositioned my good buddy because I am horny, gay, and shameless, and want to suck his cock. This shouldn’t be a big deal. I’m not sure if my argument was convincing enough. What straight guy offers to suck his buddy's cock?. I don’t think I’m fooling anyone at this point, especially Colin.
Colin came back into the room after peeing and sat next to me. “When would this 'dare' take place” ? he asked. Oh shit! I was about to lose my mind. He’s actually considering it. “There is no time like the present,” I said. Colin stood up. ‘Then I dare you to give me a blow job and make me cum”. I almost fainted. I couldn’t believe this was happening.
Colin removed his pants and sat down on the couch, all man-spread out for me. I kneeled before him, and like an idiot, I said. “No homo. Just a dare,” Colin nodded in agreement. “No Homo”. I realized at that moment that there was probably very little I wouldn’t do to get a cock I wanted, and I wanted Colin’s cock.
I took Colin's cock into my hand slowly. My touch was not going to be unfamiliar, but beyond that, what I planned to do to his cock would hopefully be unlike anything he’s experienced. The ladies just don’t have the skills or the appreciation to suck a cock like a gay man. I planned to worship Colin’s cock as if it were a god I was praying to. I would treat it with the utmost care and provide pleasure beyond his imagining. Colin would learn right away that I have no gag reflex and intended to take this cock as deep as my throat would allow. Colin will now know that only a gay man would propose the challenge to suck such a large cock.
The weight of Colin’s cock was once again surprising. It obviously looked heavy, but it was deceiving as to how heavy it actually was. I thought it might take some work to get it as hard as it was when he let me touch it, but a few strokes up and down the length of it, and Colin’s cock was at full attention and longing for some attention.
Colin’s eyes were closed, and I could sense a bit of discomfort, but I was confident I could make that all go away. I positioned myself against his legs and took a long look of admiration at the monster cock I was about to pleasure. I grabbed Colin’s cock firmly, lowered my head, and took him into my mouth. I could taste the saltiness of his precum, and I was lost in my good luck. I opened wider to take him deeper and then felt Colin shaking. I’d experienced this kind of shaking before. It typically occurs when someone is extremely aroused. I knew if Colin just allowed this to happen, the shaking would eventually stop. I took him in just a little bit deeper, swirling my tongue all around the head of his cock, and felt Colin shake even more.
SHIT!! It suddenly dawned on me that I’d just made a colossal error. Before I could pull away, cum was gushing from Colin’s cock into my mouth. The shaking, damn it. I should have stopped when he started shaking. We’d barely gotten started, and it was over.
Though I knew it was over, I instinctively swallowed as much of Colin’s cum as I could, knowing that this was most likely my only opportunity. I greedily licked up anything overflowing from my mouth and onto Colin’s cock. It felt never-ending. Colin must have released a gallon of cum into my mouth. I licked up as much as I could, then pulled my mouth from his cock. Once free, Colin angrily pushed me away and ran to the bathroom. Fuck! I yelled at him to wait, but he wasn’t going to stop. What the fuck?
I waited in my living room for almost 30 minutes before Colin finally came out. “Dude! What the fuck? Are you ok?” I asked. Colin looked defeated, embarrassed, and confused. “I don’t know, man,” he said. “Whatever you were doing, fuck! It felt too good, and it fucking messed with my head. All I could think about was what the hell are we doing, and why does this feel so good? Then I started fucking shaking out of nowhere, and I couldn’t control it.. Holy hell. Then to just bust like that? Fuck!! I literally lost control over any of my bodily functions. Dude, you know me. I never get embarrassed, and I’m super fucking embarrassed right now. To top it all off, I fucking blew my load in your mouth. Oh Fuck man, I’m so fucking sorry.”
For the last half hour, I was thinking the worst. I thought I pushed him over the line, and he’s gonna hate me for it, and this friendship is over just because I’m fucking greedy for cock all the fucking time. He’s apologizing to me because he was turned on so much that he couldn’t help but bust his nut in my mouth. Holy hell. I need to clarify this and rectify the issue.
“Dude. There is nothing to be embarrassed about. You got excited and maybe a little turned on. That will definitely bring on the shakes. I dared you to let me blow you and make you cum. Where did you think your cum was going to go if not into my mouth? I see this as a purely personal win for me. Dare completed. It's definitely not what I imagined, but it was absolutely perfect nonetheless. Please, don’t feel embarrassed, not with me.
Colin wasn’t going to be able to process all that had happened tonight within the next few minutes. “I need to get out of here,” he said. The entire time we were talking, he was still half naked, and I was trying hard not to stare at his cock, but I couldn’t help myself. It was like I was admiring it as if it were some kind of prize. Colin got dressed and left in a hurry. Perhaps I have just ruined a friendship. I hope not, but the taste of his salty cum was omnipresent in my mouth, and I wanted to savor it. I’ll call him in the morning and see if he still wants to be friends.
The next morning, I called Colin, but it went straight to voicemail. I sent a text, but after an hour, there was no response. I wasn’t surprised. Colin was not okay with what happened last night, and I have to live with the consequences of my actions. Was it worth losing a friendship over just to get my mouth around that fucking monster of a cock? I have no regrets about what I did, but I’ll be sad if I lose a friend over it.
At 6 pm, Colin knocked on my door. “I’m not gay” was all he said when I opened the door.. “I didn’t say you were,” I said. “Then why did you dare me to let you suck my cock? That’s pretty fucking gay if you ask me! I asked Colin to step inside, but he refused. This did not need to be a public conversation, but it was about to be. “Colin, I told you. I’ve experimented a little with guys. I felt bad for you, and I thought I could help you out. It doesn’t make me gay, and it certainly doesn’t make you gay. Getting sucked off by anyone should feel good. Does it really bother you so much that a man turned you on and made you cum? What are you really upset about? Colin just stood in my doorway with nothing to say. I don’t think he had the words to express himself, and I wasn’t going to let him inside now while he’s angry. “Come back and talk when you’re not angry, Colin,” I shut the door.
Colin didn’t knock again, and I saw him get into his car from my window. Why do guys get so upset about sex stuff?
Three weeks had gone by, and Colin hadn’t reached out again. I had taken for granted how much time we actually spent together. Even though I often say I live my life without regret, I was very much regretting what I’d done to Colin. I missed him and wanted to talk to him, attempting to salvage at least our friendship if it was even possible, but I couldn’t reach out to him. I would have to wait and see if he would come around.
Colin knocked on my door on a Saturday morning. Saturdays mornings, Colin and I would spend together either running or working out. I hadn’t exercised on a Saturday since the incident. “Hey,” I said. “Hey,” he said. “Can we talk?” he asked. “Of course,” I invited him in this time.
“I’ve had time to think, and I think I’ve got my shit worked out. I’m not mad at you. I never was. I just had to work some things out about myself, about you, and all the dumb shit that I do. FYI, I haven’t pulled out my cock for anyone in almost 3 weeks. I’m honoring the terms of your dare, and I just don’t want to do it anymore. I’m not my cock. What I do know is that my problem with girls still exists. After that night with you, I called an old girlfriend of mine just to fuck, and she flat-out said no way. She liked me, but just wasn’t interested in getting fucked by me and told me so.
That brings me back to you. You told me you’re not gay, but I think you’re full of shit. I talked to some of the guys on the baseball team, and there are at least three guys who think you and a few of your buddies are gay. Maybe you think you’re being discreet, but I think you’re fooling yourself. I want you to be honest with me, Dave. Are you gay?” I wasn’t prepared for this confrontation, but there was only one way to answer that question. As much as I wanted to lie and tell him no and make something up, I had to be honest, finally. “Yes, Colin. I’m gay.”
Colin was quiet, like he had something to say but couldn’t quite bring himself to. “You know, I kind of always thought you were gay, and I didn’t give a flying fuck. When I pulled out my cock, you always looked more interested than anyone else. You instantly gave yourself away, and I’m honestly a little disappointed that after all the time we’ve been friends, you never told me. It's kind of fucked up that you had to play games with me just to get your hands on my cock. I would have let you touch it and hold it and probably a whole lot more if you had just asked. I’m proud of my cock, and it certainly doesn’t get the kind of attention it needs. Everyone wants to see my cock, but no one wants my cock. I would probably have let you do what you wanted, and I would have been glad to do it. But you had to play games!”
I couldn’t have felt any more shitty. Colin was feeding me facts, and I felt terrible. I had nothing to say. He didn’t want my excuses. I just didn’t trust him enough to tell him the truth about me. What could I possibly say?
Colin walked towards me and put his hand on my shoulder. “Do you have any idea how many times gay guys have asked to suck my cock? Hundreds. They see it, and they think they can change me. I’m not gay, but the idea of anyone sucking my cock is goddamn appealing, yet I said no every time, but not to you. We have a connection and a friendship that means a lot to me. I trusted you. I wish you had trusted me.
As shitty and guilty as I was feeling, I was getting a very sexual vibe from Colin, and it wasn’t my imagination. His body language was screaming, “ suck my cock again”. According to him, I was the only one who ever asked to suck his cock that he said yes to. He trusts me.
“Colin. I’m gay. I’ve had daydreams about your cock for as long as we’ve been friends. We never talked about sex until 3 weeks ago, even though I wanted your cock so badly. That hasn’t changed. I’m sorry about the game playing. I’m an idiot, but If you think we have a connection and still trust me, I want another chance.”
Colin now had both of his hands on my shoulders and a big, devious grin on his face. “I thought you might say that”. He stepped back, pulled off his t-shirt, and then unzipped his pants. They fell to the floor, and once again the monster cock was staring up at me. Colin kicked his pants out of the way, then took his position on the couch as he had before. I wasted no time at all and was quickly between his legs.
There was no shaking or discomfort from Colin this time. We had finally established what we were to one another. I’m his gay friend who likes to suck cock, he’s my straight friend who will accept a blow job from me because girls are shitty and don’t like his monster meat. Their loss.
I had Colin's cock in my mouth and down my throat in seconds. I took him as far as I possibly could, and Colin expressed his admiration for my skills. No girl can work a cock like I can, and Colin would agree. Colin was going to get the complete treatment that I was denied 3 weeks ago. For 25 minutes, I ravaged his cock, had both balls in my mouth, and rimmed his ass. Rimming took a few attempts, but once he realized what I was doing and relaxed into it, he was pushing back as any man should. The taste of him was simply intoxicating.
I once again took his cock into my mouth and worked his cock like a man with conviction. I was intent on milking every ounce of cum from him and leaving his balls empty. I worked the head of his cock while I stroked him with my other hand. I applied pressure to his tip and stroked his cock aggressively. Colin began to breathe heavily, and I knew the prize would be mine shortly. I worked the head of his cock, stroked his shaft with my other hand, then pushed a finger gently up his asshole. The rimming had relaxed him, and Colin’s hole did not fight back. It was only a matter of moments before Colin’s cock erupted like a volcano in my mouth. Hot cum was being pushed down my throat in volumes, and I refused to allow any of it to spill. The taste of him was just as I remembered. I wasn’t overcome with the feeling that this would be the last time, but just in case, I wasn’t going to miss a drop. Colin sat back, spent, then pulled me in close for a hug to assure me that everything between us was going to be ok.
I was so happy to have my friend back, and our relationship had evolved. Colin and I had a standing meet-up every Thursday night. I got to worship his monster cock, and he got sucked off properly as he deserved. We had become very comfortable with one another and would simply hang out together naked. He didn’t mind at all if I lay between his legs after we were done. Sometimes he would even stroke my hair as I kissed his flaccid, yet still monster cock.
A few months had passed, and our friends-with-benefits situation had become a very natural thing for both of us, but it was a one-sided arrangement. I was getting him off on the regular, but I was taking care of my own needs. I desperately wanted that to change, but how far could I push Colin? He was getting off with me regularly and finally enjoying regular sex, but I wasn’t going to turn him gay. He isn’t gay. He likes women, and I’m a very willing substitute that he’s accepted and enjoying. I’m not fooling myself.
I finally had the nerve to approach Colin about taking the next step. I asked Colin if he ever thought about fucking me. His answer didn’t surprise me. “Absolutely not” . I explained to Colin that it would take some practice on my part, but I wanted him to fuck me. I spared him all the prep details, especially the part where I had been practicing with an extra-large dildo for months. I stressed to him that I wasn’t scared of his cock and fucking a man would be different than fucking a woman, but I was confident I could take him, all of him, if he were willing. Colin was on the fence. We’d gone this far, what did we have to lose? He didn’t rule it out and agreed to think about it. I think he was concerned about hurting me. As if!
Weeks had passed, and nothing had changed between us. I was tired of waiting for Colin to make up his mind, so I took him by surprise. One Thursday evening, I’d douched and prepped hours before with the intention of trying to take in his massive monster cock. My mouth was working on his cock as it had been for months until I climbed on top of him and presented him with a bottle of lube. “Don’t freak out, just listen. You don’t have to do anything. Just lie back and let me take care of you. I’m going to sit on your cock and gradually lower myself onto you. I honestly don’t know what to expect, but I really want to try. If I’m ready to actually take a fucking, I’ll let you know and you can have your way with me”.
Colin seemed hesitant and backed into a corner, but his cock said otherwise. I lubed up Colin’s cock and got it as slick as I could, then lubed up my very ready hole. I’m not an inexperienced bottom by any means, but Colin’s cock is more significant than any cock I’ve ever taken, and it was going to be a challenge regardless, but a challenge I was up for. The 12’ dildo I’ve been practicing with was getting easier every session to the point where the pain was minimal and I could cum. The real thing shouldn’t give me any problems, right?
Colin’s cock was a little longer and a lot fatter than my dildo, but I was confident.
I straddled Colin’s legs and continued to apply lube. Colin’s wide-eyed expression and look of desire made me want it even more. I didn’t want to disappoint him. He loved the blow jobs, but up to now, he didn’t have a lot of proper fucking under his belt with girls and had never fucked a dude. After many months of blow jobs, Colin was very comfortable with me handling his cock. It seemed natural. I wanted desperately to give him a fucking he would never forget. It was now or never.
I lifted myself and placed Colin’s cock between my ass cheeks. I told Colin a few times, ‘Let me do the work and I’ll let you know if it’s okay for you to take over.’ The most natural thing to do is to push forward, but I needed Colin to let me get him inside me first. He seemed anxious but was doing his best. The initial acceptance of his cock into my hole was difficult. Colin's cock was thick from head to base, and I simply wasn’t as relaxed as I needed to be. I took some deep breaths and forced myself to relax and dropped onto Colin’s cock, maybe 4 inches deep. It was a very intense 4 inches, but I wasn’t going to give up. I dropped down a little further, and it was like my hole was putting up a fight. I wanted this, and I could see in Colin’s eyes that he did do. I bit my lower lip, took another deep breath, and forced myself further down Colin’s cock.
It was like my asshole suddenly gave up the fight, and I was fully opened up. Just like that, Colin was balls deep inside me. I couldn’t move for a moment and knew Colin was dying to start his fucking motion. I rose up and down slowly, allowing my rectum to get familiar with this invader. It didn’t take too long, and I gave Colin the go-ahead to start fucking me.
“Oh my gosh. It’s so tight,” He said. I couldn’t help but think that every asshole and every vagina were going to be tight when faced with a monster cock, but I kept that to myself. I controlled Colin’s fucking as best I could, but riding him like this wasn’t going to work for much longer. Every time he pushed into me, I felt it deep, and my quads were burning from holding Colin off from pounding me to death.
I lifted myself off of Colin’s cock and told him I needed a breather. I really did need a break from his massive cock. At first, I wasn’t sure I could take him, but it wasn’t as difficult as I imagined it would be. I wasn’t going to be able to sit on his cock like that for the duration. We’re two big men, and we needed a different position.
I got on my back and raised my legs and told Colin to get between them. “You can see my asshole, Colin. Aim for it, and I’ll help you get in there. Just take it slow and don’t try to push every inch of your cock into me all at once. I can accept it, but I need time to do so. Got it?’ I made Colin lube up my hole, which was a 1st for him. He’s touched my cock many times over the last few months, but he’s never seen my asshole, let alone put his hand anywhere near it. My asshole was waxed, pink, and ready. If I had to say so myself, my hole was pretty and inviting. Colin got a good look, and he smiled with approval. Now he was fingering it up and pushing lube into my hole. This was all new to him. If he wasn’t enjoying it, he’s a damn good actor.
“Ok, Colin, I’m ready”. I’m actually a pretty flexible guy and pulled my legs back as far as I could to give Jimmy the best view of his target. With my feet practically behind my head, Colin found my hole with no problem and pushed himself into it with admirable patience. Once I gave him the go-ahead, Colin went to plow town. It was a lot of work, but I was able to keep him from wrecking my entire rectum. I had to push him back several times to slow him down before I finally got used to the sheer volume of what was inside of me.
Colin was now fucking me into the following year, and I couldn’t believe how amazing it felt. It was the most enormous cock I’ve ever taken, and I think the dildo practice helped out immensely. I could feel Colin's pace increase, and I just stopped holding him back. The man needs to fuck without restrictions. He’s been holding back from power-fucking anyone for years. Not tonight, though. “Fuck me, Colin,” I demanded. Give me every inch. Fuck me like you’ve always wanted to fuck”.
Colin did not hold back. I could feel his hips slamming against me, meaning every inch of his monster cock was deep inside me, and I absolutely knew it. All in all, Colin was inside me for maybe 20 minutes. Colin looked deep into my eyes, and his expression was beyond grateful.“I can’t hold off any longer,” he said. I'm going to cum.” Even with that brief warning, I timed my nut just as he busted inside me. Colin watched the cum explode from my cock and onto my belly. He looked fascinated that I was cumming just as he was. It was one of the most intense orgasms I’d ever had. Colin was utterly spent, and as soon as his balls had entirely drained inside me, he collapsed on top of me. It was the 1st time anything like that had happened between us. It felt very natural to have him on top of me. Colin caught his breath, then finally pulled himself out. He was still 90% hard, and I felt every bit of that extraction. I’ve never felt so empty in my entire life.
Colin looked at me with such gratitude as he rubbed my cum all over his torso. “I want to kiss you, Dave. I don’t know why, but I think I just need to”. I looked up at him, closed my eyes, and waited for it. It was a lovely, sensual kiss. A kiss of appreciation, really. I no longer had romantic feelings for Colin. We were friends, and I was more than happy to take care of his sexual needs from time to time. A romantic item I knew we would never be. The kiss changed nothing, but I felt the enormity of his appreciation.
Colin and I continued our arrangement until we graduated. We were both moving on to Grad School, but in different parts of the country. There would no longer be weekly blow jobs or anatomy-altering fuck sessions. I wanted him to fuck me one last time before we headed our separate ways, and the feeling was mutual. There was no guarantee that we would ever see one another again, and we both wanted it. It was a fantastic, yet bittersweet fuck, timing our orgasms together, one last time. I was going to miss his cock, and I was sure I would never find another like it.
Colin and I kept in touch, and I was overjoyed that he’d finally met a woman who didn’t have an issue with his cock. I would tell him many times over the years that there is a person out there for every cock.
Many years later, Colin called, saying he would be in my town for business. We made dinner plans, but we hadn’t talked about getting together to fuck. I had a boyfriend, and he was with the same gal for years. Neither of us was in an exclusive relationship, but in the back of my mind, I just wanted to get destroyed again by Colin's enormous cock. When we met up, he looked just as good as he did the last time I saw him. It was like we’d never been apart. I was still very active and fit and reminded Colin that I was still very flexible, which he chuckled at, but he knew exactly what I meant. I was hoping my flirting wasn’t over the top.
After dinner, lots of catching up, and a few drinks in his Hotel bar, he reached across the table and grabbed my hand. “I want to fuck you so badly,” he said. I produced a bottle of lube from my jacket pocket… Fuck? I was hoping you’d say that.
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