Best Friend And “Straight” Roommate

"Let me take a measurement, please. God, you're so much bigger than I am!" I begged, hoping the thirsty compliment would persuade him into agreeing.

"Ok, fine. I'd actually like to know," was his reply.

I held the tape at the base of his dick and ran it out to the tip careful to touch him in the most clinical way so he wouldn't make me stop. I savored each moment, though, and can remember vividly the heat of this monster on my fingers. "7 3/4, um, no 8 inches at the slit," I reported. But the most impressive part to me was the girth. I turned the tape measure and wrapped it around his monster. Perhaps he was a bit more hard now.

"Holy shit!" I exclaimed as I saw the measurement. "Six inches around! Eight by six! You've got two inches on my length and an inch and a half on my girth. 8 x 6-- Damn!" (These are real measurements, not the inflated porn/Grindr/photoshop 'internet inches' common today, and Jonathan was truly in the top 1%.)

"Hmph, good to know. I don't have a tape like that and haven't measured since high school," he admitted.

My dick was straining against my boxers. "Jonathan, please, I have to see something." I pulled them down and my dick sprang out. I was as hard as can be, though a much shorter, thinner version of what I was seeing in front of me. Jonathan didn't precum, but I'd been pouring it out, and my boxers had a massive wet patch I could feel, cold against my foot now where they rested. My slit was wet with a fresh bead. My head was flared and veins pronounced, but the difference between myself and my best friend in front of me was almost comical. I felt so small!

I moved closer to him and he didn't flinch away, so I put my dick side by side with his. His dick head was pressed against my skin and pubes as I compared us and mine tip barely reached the fringe of his bushy pubes, spreading precum which looked looked like stringy dew sticking to grass.

"Oh my god, Jonathan," I exclaimed, "I'm ridiculously turned on and yet humiliated at the same time. I've always been pretty similar in size to guys I've hooked up with and dated. Maybe I'm a touch longer and they're usually thicker. But look how tiny I am in comparison to you!"

"Yeah, it's a dramatic difference," Jonathan agreed looking down at our cocks together. "Your dick is fine, but it definitely is something to see a side by side comparison." We knew each other so well and the tone of his voice told me he was turned on even more by realizing his size this way. Something changed in that moment. He felt more superior, more manly. His dick grew even more hard and inflated.

"Ok, well I'm going to have to jack off now," I said my eyes bugging out as I saw him inflate more. This was my fantasy come true! "How about you just stand there and I can jerk off quickly with you as eye candy?" I proposed. Might as well make the most of this even if it wasn't going to be a perfect ending.

"Tell you what, Matt," Jonathan started with an egotistical, even condescending tone that had suddenly infused his voice. He began to stroke himself slowly, stepping toward the bookshelf and picking up a miniature hourglass that was still out from when we'd had some friends over playing Taboo. "I'll give you sixty seconds or ninety seconds or whatever this times to do whatever you'd like to my dick. Time starts now." He held it directly in my face and flipped it over in his hand. The sand started to flow.

As fast as those grains moved through the hourglass, I dropped to my knees. I fondled his balls in one hand and wrapped my other hand around his cock. My fingers couldn't wrap all the way around and touch because of his thickness; it felt like I was grabbing my forearm. I lifted his dick and licked his balls, sucking lightly on them before bringing his monster cock to my face. I ran my tongue all over his head, then licked the length of the underside of his dick like a lollipop, pressing it up against his belly. It was so large, I couldn't seem to get more than part of it in my mouth at once. Would this dislocate my jaw?

"I don't know how to get this in my mouth," I stammered, hesitating. Plus, although it seemed unbelievable, I thought he looked even more engorged than before. I was crackling my fingernails through his pubes. I touched my dick with one hand, which was aching and dripping precum into the carpet. Jonathan didn't precum at all. I stroked myself once and knew I could blow my load at any moment.

"Time is running out," Jonathan taunted, shaking the timer which was halfway done, though he seemed a bit breathless and his voice had a strange quality to it, which surprised me. Clearly I was doing something for him.

I grabbed his dick, opened my mouth as wide as I could, and jammed it in. The head alone filled my mouth completely and I couldn't do much other than twist my head around. With both hands, I jerked him off meanwhile.

"Oooh," a breathy moan escaped from Jonathan.

My eyes were tearing, lips hurting from this stretch, but I was a determined gay and was going to have my full minute worshipping this monstrousity. But I started to gag and couldn't get my breath. I had to pull back from his cock. I thought I was going to throw up. I stroked his length furiously with my spit for lube as I backed off him and caressed and pulled on his balls, which were now quite tight and pulling into his body.

"Time's up," Jonathan announced, his voice barely working and in a strange tone. I sat back on my feet dazed from not just the drinking/smoking earlier in the evening, but the whole night, and mostly that I'd almost killed myself trying to suck his dick. I still couldn't tell if I was going to pass out or throw up.

Through teary eyes, I looked up at Jonathan to try to figure out why he sounded weird as he'd spoken and was shocked to see his face twisted in ecstasy, eyelids fluttering. In my agony, I hadn't realized how turned on he'd gotten. For all his braggy showmanship and despite his denials, he did get off on my attention and affection. That's when I felt hot wetness hit my face.

"Oh my god," Jonathan practically shouted while moaning, grabbing his dick to control it as it spewed. His dick was spraying me with cum on my face and neck. He lightly stroked himself with one hand and ran the other up his stomach, pinching his nipple, convulsing as his orgasm continued. His cum was going everywhere, my hair, eyes, up my nose. He looked down at me, his mouth open and eyes mixing what I guessed was arousal/ O-face with shock as he watched his load cover his best friend's face.

I grabbed my dick and started tugging during this unexpected dousing. It only took a few strokes before I too was spewing cum. Normally I don't shoot far, but I was so turned on from everything that I blasted ropes of cum on Jonathan's left foot, close to where I was kneeling.

We both calmed as our orgasms subsided. He was still looking down at me and I up at him from my knees. I started wiping my eyes and face clear. We both started laughing.

"Well, Matt, I hope this was everything you hoped it would be," Jonathan said, lightly tapping me in the face with his dick playfully. "Sorry about that cumshot. I haven't had sex in a couple weeks since Sarah left town and it snuck up fast. I haven't had a girl ever go after my cock with such gusto!"

I smiled, standing. "I thought I was going to choke to death. But at least it would've been a 'monumental' death," I replied. We both laughed again.

"Well, I'm going to shower and clean up for bed," he said, looking down at and lifting his cum covered foot, his face scrunching up in disgust. "You do the same and then we'll smoke once more before bed."

"Matt," Jonathan continued in a serious tone, "I love you; you're my best friend, my main companion. But you can never tell anyone about this. I already get too much 'Jonathan's secretly gay' crap from everyone. I only let this happen because we're moving apart in a couple days and everyone is gone. And I really didn't intend for it to go this far. I need your word. Never."

"I've always told you I'd keep it between us if anything happened," I replied, cooly. "That still stands."

With that he turned and left the room, starting his shower. I retreated to my bathroom and showered as well. My mind continued to replay the night over. I set out my journal to write it down later and immortalize another insane night as Jonathan's "main companion."

XXXXXXXXX

We didn't do anything sexual in the last two days as roommates; most of our attention was focused on packing and I felt like I'd gotten the desire out of my system, for the time being. I headed off to the Midwest for grad school and Jonathan upstate New York. I visited him a few weeks after we moved and he brought me to a party where he was meeting his grad cohort. Once again, I played his wingman and helped him score with a new girl. I felt angry and dirty to fall back into that role, and I'm sure part of that had to do with how our encounter had changed my feelings for him, even slightly. He launched into a tirade at the end of that visit about how we weren't lovers and I should forget our one crazy night and how he regretted it. Still, the next morning he flaunted his morning wood in front of me before I left the next day. That visit really damaged our friendship. We would interact over social media once in a while and I watched him marry, divorce, change professions, and remarry another woman. I always wondered how they handled his massive member. I actually think this encounter turned me off to huge dicks, though I was a size queen until I felt so humiliated side by side with Jonathan; I really, vastly prefer average now. I can simply do more with it and it's more enjoyable. And I don't feel inadequate myself!

Some part of me always fantasized about a threesome with him and his wife, or else just another crazy evening with the two of us. When we spoke more recently, he would talk about us visiting each other and how much he wanted to reconnect in person instead of by phone or text. He said he'd been nostalgic for old times. What else could that have meant? Unfortunately, Jonathan died, suddenly and tragically young. While I'll never have a chance to visit him and find out what his desire to see me was about, I write this tribute in memory of the times we had together. He was a profound person, intelligent, and deep friend, although I needed a ton of therapy after being his roommate for a year. May his memory and my story inspire you to make the most of every one of your personal interactions for the brief while that we get them.