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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