Best Friend and “straight” Roommate

This story is a compilation of a few events with one of my undergrad roommates, Jonathan, a flamboyant exhibitionist, who proclaimed himself straight, though his actions seemed to blur and contradict this. I recently found a diary I kept from that time, pulling me back to those days and the crazy adventures we shared, which often left me horny and tormented. I decided to write up a few of them here and hope you enjoy. Here I recount when I first met Jonathan, a time I overheard him having sex with his girlfriend, and just before we moved apart— the day when he finally whipped out his hard, huge dick in front of me. Let me know in the comments if you ever had a "Jonathan" in your life; I suspect it's fairly common.

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My earliest memory of Jonathan is the first time he spent the night at my apartment. This was in the summer before my senior year of undergrad. My current roommate was out of town for the weekend, having a final vacation hurrah in the US before her return to her native homeland in Norway. After a few other prospectives had fallen through, I was a little desperate to find a new roommate at the last minute. A mutual friend suggested Jonathan and I would make good roommates. Aside from having had classes together because we were in the same degree, I didn't know Jonathan well, so we agreed to hang out one evening, and, in his words, to have a "sleepover" to see how we clicked and how he liked the apartment. For whatever reason the night wasn't memorable, but the next morning something happen that I'll never forget.

I woke up a little early like I usually did, and went to the kitchen in my boxers and t-shirt to get some water. Around home I pretty much was always in only my underwear. I was just wondering when Jonathan was going to wake up at the very moment he walked around the corner, also in a t-shirt and boxers.

"Good morning," I said, cheerfully.

"Morning," he mumbled, rubbing his eyes. I'd learn he hated mornings and waking up.

Jonathan was a bit taller than I was, maybe six feet to my five ten, and he had a toned body, though he didn't work out regularly. He ran occasionally and liked to swim, even earning his lifeguard certification in the year I knew him. I did yoga once or twice weekly; I had a decent aesthetic, though I was a bit more chubby than Jonathan. He had sandy brown hair, slightly receding, and brown eyes, compared with my blonde hair blue eyed combo, and he was more of an olive complexion than my pasty white. His great facial features included an intoxicating smile. He had a sort of movie star, perfectly groomed look, but without the work, even apparently upon waking!

I was delighted Jonathan was uninhibited and only wearing his underwear in front of me. Among our mutual friends, Jonathan had a reputation for being suuuuper well hung. In fact, some girls had given him a nickname of "the monument" because his dick was supposed to be of monumental proportions, like the Washington Monument. I stole a glance at the flimsy boxers he was wearing today, expecting to see a bulge swinging, but it looked like nothing was there! I couldn't understand this, even I had a bigger bulge in my boxers, and I'm an average sized guy— a grower at that. At this point, I was thinking it might be my only chance ever to see him in his underwear, if we didn't end up rooming together, and I wanted to see this beast for myself.

"Can I get some water?" he asked groggily, interrupting my mental soliloquy.

"Sure, make yourself at home," I replied.

Jonathan stood, unmoving. Realizing he didn't know where anything was yet, I got a glass and filled it from the tap for him. He took it, leaning back against the counter. As he drained the glass, I took the opportunity to check his crotch again at this new angle. That's when I saw. His dick was huge and hard! Tucked up into the waistband of his boxers, he hadn't even waited for his morning wood to subside before coming out of the bedroom! That's why there was no dangle. It looked like a Pringles can stuffed in his boxers sticking up until his t-shirt overlapped. I immediately started to get hard and shifted my stance to cover my tenting boxers, standing in a ridiculous cross legged manner that somehow seemed to squeeze and stimulate my prostate.

Jonathan chatted casually with me about the plan for the day, while I nodded and smiled. Meanwhile, every chance I got, my eyes went to his crotch. We must've stood there 15 minutes talking before he started to lose his erection— I'd later learn he was turned on by exhibition— and finally his dick softened enough to pop out from under the waistband. It immediately waggled straight out in his boxers, still quite large and perpendicular in his semi state. At that very moment, he made a dramatic point as he spoke and gestured with flair that allowed him to seamlessly grab his dick and conceal it from view. He announced he was getting ready for the day, rushing out of the room past me to take a shower. I immediately reached in my boxers, popped my dick out the fly, and started jerking off. I had a large, dark spot of precum on my sky blue boxers from how aroused I'd gotten watching him this whole time and wondered if he'd noticed it growing wet as we talked. He had seemed to be smirking at times. I blew my load in a few tugs, electrified by what I'd just seen. Needless to say, I decided Jonathan would make a perfect roommate.

Living with Jonathan was one sexually frustrating experience after another, probably my most frustrating year ever sexually! He was a straight guy whose closest friends and roommates had always been gay men. He loved going to parties with me because I'd be his wingman and help him score whatever his "girl of the month" was. After he'd flirted a bit with her, he'd find me and pull me into the conversation. On cue, I'd wax poetic about his monstrous dick and his nickname as "the monument," and with that, she'd be snared: all the girls wanted a ride after my endorsement. Then she'd be around for a few weeks until they were tired of each other. These weren't long term connections. Plus, senior year, almost everyone is headed elsewhere after graduation, so longer connections weren't really being considered.

This was how Jonathan liked things. He told me numerous times that he liked life best with me as his "main companion," while about once every week or two, he'd call up a girl to have sex with. "Main companion" meant we were together all the time, best of friends, inseparable. We ate together, worked out together, vacationed together, visited each others' families, shopped, drank and used drugs together. In fact, near the end of our year as roommates, Jonathan declared that he preferred sleeping in the living room, him in a reclining chair and me on the couch, because that way we could sleep in the same space together and never stop being together, even at night. It was crazy! I always felt he got jealous when I brought a guy home. He was undoubtedly controlling.

When we were in our apartment alone together, we were rarely clothed beyond our underwear. I'd grown up just being in my underwear at home, so it seemed natural to me, plus, it was always slightly arousing to be in front of a cute guy in undies. Jonathan took that as the cue for home life, and while he would laugh at me when I walked in the door and immediately stripped down to my underwear, leaving a trail of clothes like a fireman, he would always follow a second later. Once a mutual friend showed up unannounced and Jonathan flipped out because we'd both gotten out of the shower and were just wearing towels, hanging out with obvious boners under the fabric. He made a new rule: any visitors had to call or text ahead.

Jonathan was constantly tormenting me and seeking my sexual thirst, though he refused to quench it. One of my most vivid memories is of the day he earned his lifeguard certification. He decided, because of the size of his large cock, that he needed to wear a Speedo underneath his board shorts to keep it contained. So he purchased a few and then did a fashion show of these Speedos for me at home. (Which in hindsight was ridiculous; no one would see them underneath his shorts!). He got more and more aroused as he tried on different ones until it looked like he was smuggling a nightstick in a bright red brief. Rather than avoid mentioning his boner, he started to adjust the angle of it and ask me, hypothetically, if he were to get hard when on duty, which angle made it the least noticeable, right, left, up, down? But he never allowed me to touch his dick. Then he'd point out that I'd gotten hard and now we both had boners at the end of an event like this "fashion show" and say that it was time for us to go to our respective rooms and jerk off. He wouldn't jerk off in the same room as me, despite repeated requests.

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Things escalated during our final month together, though. A few weeks before the summer ended, after graduation was over and we were beginning to make plans to move out, Jonathan had his last visit from his long time "girlfriend," Sarah. In retrospect, I'd say she was a fuck buddy who tolerated all Jonathan's other interspersed flings, but that wasn't polite language in the south where we lived. Sarah and Jonathan usually hung out once every couple weeks, but had gotten together less frequently as the summer was winding down.

I knew their routine by heart at this point: Sarah would come over after dinner, hang out in the living room with both me and Jonathan for a half hour making small talk while we all shared some wine. Then there'd be some excuse to look at something in his room on his failing computer which would lead to them retreating there and getting things on. This night would be no different, I figured, except that Jonathan and I were drunk and stoned before Sarah arrived because we were partying hard, ending the summer with a bang.

When she knocked on the door, Jonathan leaned over to me and whispered, "She's not going to stay the night. I'll be quick; I really prefer it to just be the two of us."

"I can do whatever she does for you," I retorted.

"You're a trip, Matt," came his reply, laughing as he opened the door and greeted her enthusiastically.

The night proceeded exactly as their nights did. I was bleary eyed by the time they ended up heading to his bedroom and just sank back into the living room couch. Suddenly I realized I could hear clothes rustling and slurpy sucking. My eyes popped open. He hadn't closed the bedroom door.

"I love your monster cock," I heard Sarah say. "I'm running out of chances to enjoy it."

"Nonsense, we'll visit each other in grad school. Boston won't be far," Jonathan's muffled reply came. (He was lying; he'd say anything.)

My dick was instantly rock hard. I couldn't believe I was hearing this! I mean, I'd heard them through the door before but this was different. It was so vivid! They were probably 10 feet away and the sounds of their fucking were growing louder. Sarah began to whimper rhythmically, "oh, oooh, umph," on a softly repeating track that was drifting into my ears, along with the sound of their bodies sliding and slapping together. I could hear the bed creaking in regular rhythm. I felt like I was in the room with them.

I debated two options in my hazy, drunk brain: one, getting up and going to my room where I could jerk off, or two, moving into the hallway where I could hear better, but still be out of sight. Meanwhile, I started stroking myself right then and there on the couch in my boxers. As their sounds grew, I decided to stay put, worried that any movement on my part around the apartment might be heard and end up with the door closed. I was getting close anyway, crazily turned on by this auditory voyeurism.

"Sarah, ohh, oof... God your pussy is tight... I'm gonna blow," Jonathan's voice grew louder. I busted silently in my boxers on the couch right after hearing that and with a grunt from the bedroom heard that Jonathan must've too. It'd been a few weeks since he'd gotten laid, so his stamina was low. (One of our mutual friends told me he relied on the size of his member to do the work; he wasn't actually rumored to be excellent in bed or have much stamina. He justified it to me that everything felt incredibly tight because of his size and so he often got off quickly.) Neither of us had lasted very long just now. Plus, simultaneous cumshots!

I was trying to figure out how I was going to play this off. My wet boxers were obviously full of cum, and Sarah would have to leave through the living room where I was siting. If I walked to my room now, they'd definitely hear and see me in my cummy glory. My stoned brain wasn't working quickly.

"JONATHAN!" Sarah's voice came in an urgent whisper. "You didn't close the door! OMG. Do you think Matt heard?" I heard some scrambling and the sound of clothes being put back on quickly.

I pulled an afghan halfway over myself, covering my mess, and put my head back, feigning sleep. It wasn't difficult in my half drunk/high state. Meanwhile, I heard footsteps softly trickle in and out of the room a couple times. The front door unlocked and opened. A quick kiss and whispered goodbye and the sound of the door locking. A few more footsteps. A pause. Silence.

"Open your eyes and stop pretending, Matt," Jonathan's voice came at full volume from a few feet away now. "Did you enjoy that? I did it as a gift for you."

I peeked open my eyes and Jonathan was standing in front of me in boxers, his dick still partially hard, with an obvious cum stain on the front from the leaking of the last drops as he softened.

"You're crazy," I replied. "That was insane! I could hear everything."

"I know. You know you loved it. And she's gone, so it's just us, which is how I like it best. Come on, let's get stoned again before we sleep," he replied.

When I moved to get the pot together and roll a joint, the blanket came off and my cum soaked boxers were in view. Jonathan started snickering.

"See, Matt, you did enjoy it!" He grabbed his dick and flopped it in his boxers. "We both got off and are in cummy undies now!" He started laughing outright. He was referencing the small amount of leakage he had versus my outright mess. I didn't know how to respond so instead lit the joint I'd just finished rolling.

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A few weeks later, and three days before we would move out and end our time as roommates was the climax of this crazy sexual year. We were sitting in the living room drunk and stoned hanging in our underwear as we usually did. Jonathan started to get a bit aroused and I noticed his dick growing. This wasn't unusual and typically would end with us heading to our respective rooms to jerk off and then reconvening to carry on the evening a few minutes later. Jonathan always said we were jerking off "together, apart." Tonight would play out differently, though.

Jonathan kept sitting there as his dick grew and reached full mast. The boxers he was wearing were a pair that meant he needed to do laundry soon. They were flimsy, and the white gossamer material had about the thickness of a Kleenex. I could see his dick, which was not just tenting the material, but throbbing visibly with his pulse. The angle of his cock in his boxers and his reclined posture made the ridge of the head completely visible. This man's member was long and thick. He was watching me as his throbbing member hypnotized me, looking at his cock, flexing it to make it rise and strain against his boxers, and watching me as I watched him. I quickly grew rock hard, tenting my boxers as well, though a much more modest tent due to my average size. Like Jonathan, I didn't sit up, adjust, or conceal my aroused state and let my cock throb in my boxers for him to see. Jonathan began to run his hand up and down his dick over his boxers and started flapping it around, still making deliberate eye contact with me while he did this. Neither of us was getting up to leave and jerk off as we always had at this point and the exhibition of having our tented underwear so brazenly on display was completely unusual. The sexual tension was thick in the room. It was like a match of gay chicken. The change in behavior from him was really turning me on and my heart was pounding; I already felt like I could cum.

"God, I am hornyyyyyy!" he exclaimed loudly. He started thrusting his hips slightly as he continued stroking himself through his boxers.

"Jonathan," I said desperately, "Pull it out! Let me see it! I'll show you mine." I'd already seen him naked when changing or because of a dropped towel after a shower a few times— but these times he'd been mostly soft. I say "mostly soft" because Jonathan was a big time grower, and once doing yoga in his boxers I'd seen him pop out totally unaroused where you'd never have guessed what would happen when he boned up. However, he always seemed in some state of partial arousal and literally every other time I'd seen him, even changing in a public dressing room, he was somewhat fluffed and at least a third hard. I'd practically seen him already naked and hard as we were always in underwear around each other and often aroused before we'd jerk off. But I wanted to see 'the monument' in the flesh.

"Matt, I've got no desire to see your dick. I'm not into guys, so the 'we'll be in it together' mentality doesn't work," he said. "Besides, you are basically seeing it now." He grabbed himself with two hands and tucked the material around his dick, flexing it. I could see veins through the thin material of his underwear.

"We're running out of time," I protested. "You've tormented me all year, flaunting 'the monument' in front of me, and now in a couple days we'll be off to grad school, separate, and I'll never see it! You owe me for all the times I've bragged to whatever girl you wanna get with about how huge you are to help you get a hookup. Whip it out!"

"You really wanna see it?" he asked taunting, then shrugging. "Ok." He stood up and pulled his boxers down, revealing his huge cock. I stared at it, as my dream came true and I finally saw him completely naked and aroused.

Now I've seen a lot of dick in my life, but his was and still is the largest I've ever seen in person. His cock was absolutely huge but it was also aesthetic. The head was reddish purple and flared, even more massive than the shaft. Thick veins ran along all sides of it. He began to shake his torso, wagging 'the monument' back and forth. He had a hairy belly that continued down into bushy pubes. He didn't need to manscape, unlike me, because his dick looked huge no matter the state of his pubic hair. If being a dick model were a profession, Jonathan would've been perfect for this occupation.

"What do you think?" he asked, his voice giddy with excitement he tried to cover as he smirked at me while I sat up and squirmed in ecstasy on the couch, leaning forward to get a closer view. He was clearly really turned on by this exhibition.

"It's huge and gorgeous!" I exclaimed, "So straight with no funny bends and a bulging head!" I wanted to feed his ego to see if I could egg him into more. "Lift it up so I can see your balls better," I requested. He complied, and revealed his nut sack. Now, my balls are very large and unfortunately make my average dick look smaller, but his balls were average and actually looked quite small because of the size of his huge dick. "Nice!" I said, "Your dick's huge, but your balls are normal."

"I'm not even completely hard," he boasted, holding his dick in one hand and smacking it against palm of his other. He clearly was, though. If he could get harder, it was impossible for me to imagine.

"Can I touch it?" I asked.

"For the millionth time, no, Matt," he replied. "You just get to look."

"Ok... well then... Don't move," I said, springing up from the couch. I ran into my bedroom, my dick flopping in my boxers, to get my tailor's tape measure and returned to the living room where he stood with a query on his face.