First Time's a Charm

Timothy Bishop
9 mins read
Published about 2 years ago

Every young gay man has that period of time he’ll never forget for its magic — when you’ve moved out of your parents’ house and into the college dorm. When you can to shed that small-town life that held you for so long. When you can finally show the world the gay man that you are becoming. 

That's also when you’ll likely have the best sex. 

At nineteen, I made my way to a college in Quebec, where all of the eighteen-year-olds liked to go because they could drink at a younger age than if they’d stayed home. For me, it was more than the freedom of buying my own booze. I came from a remote place; I couldn’t come out as gay until I left.

I was still young-looking for my age, but at least my body had shed the lingering weight that had held on through childhood, meaning I could stop hiding in baggy clothes, and try something else on instead. Something that might allow me to show the world I wasn’t just another one of the pack of straight men from my hometown.

In the heat of that summer, I wore dark shorts and a polo shirt. Formal enough to show the world that I wasn’t like the guys I grew up with, but certainly not flamboyant. My favorite combination was a blue polo, a pair of shorts that were a bit shorter than what I wore in high school, and Chuck Taylor Converse. 

That’s what I was wearing the night I met Keith. 

Even though he was a year younger than me, having turned eighteen just days before arriving at university, Keith had all the makings of a man. His tall, supple frame drew me in from afar and I could already tell that he was going to be something special.

We had first connected through Facebook before our arrival on campus. The first photo I saw of him was one of him sporting a white dress shirt and a checked vest, playing a guitar. Keith’s piercings included one in his eyebrow and many more in his ears. He had bright green eyes and dark hair and, despite being so young, he had stubble that indicated the full beard was right around the corner. 

On Facebook, we talked of our prospective majors, and plans to travel abroad. While I would be paired with a jock roommate whose best quality was walking around in tight underwear, Keith would have a room of his own with his own bathroom. Our conversations didn’t mention the fact that we were both gay, and I certainly didn’t say anything about how I attractive I found him. I felt gangly, awkward, and out of his league, to be quite frank. It didn’t matter, anyways - Keith had a boyfriend whose photos he posted frequently. 

Then, days before university, those photos were taken down. He never mentioned what had happened. 

After all of my belongings had been moved in and my parents left, I settled in for my first night at university. It was a hot summer evening and I had donned my outfit with care. I sipped white wine in the halls while I chatted with my new residence neighbors, and we all made our way to the beer gardens together. I had no idea just how much the evening had in store for me.

The quad crowded with students by the time we arrived. After about an hour and a drink or two, I began to feel the buzz of anticipation about myself. Where were the other gay boys? I saw men and women kissing, and a few men who I suspected might also be gay would look at each other for a few minutes before slipping off. Then, just as the party seemed to be dying down, in came Keith. 

Keith wore a salmon tanktop that showed off a muscular, furry chest and a pair of gray trousers that showed off the angles in legs that all gay men thirst for. He wasn’t a muscle stud, but he had the body of someone who worked hard and carried himself with the confidence of a strong young man despite being barely a boy of eighteen. 

“You’re James, right?” he said to me. 

“Yeah, I am!” I nodded, too enthusiastically. Between the wine and Keiths' arrival, all the blood rushed from my head.

“It’s great to finally meet you,” Keith said. It was immediately obvious that Keith had intentions for me that night. The kind of intentions that I had hoped for but never truly anticipated. “I can see the effect of travel on you, you’ve got some great color. And great muscle tone,” he added. 

He wasn’t shy. In fact, he had a boldness that I had never encountered. He took my hand and we began dancing slowly to the music, regardless of the fact that there were only straight couples around. We looked at each other, and he leaned in to kiss me. 

Until then, I had never been kissed before. I had jokingly participated in games of spin the bottle as a teenager, but of course rarely found myself in a situation where I could kiss men. When I tasted the sweet nectar of Keith’s soft, sweet lips and the enticing prickle of his soft beard — despite his furry form and thick arms, Keith was one to use a flavored chapstick and musky beard oil — I felt myself being sucked in further. 

Keith looked around, and then pulled a flask from his hip. He handed it to me, and I took a long drink of vodka. Years later, Keith and I would present papers where we would quote the words of a favorite writer’s admiration for vodka. But for tonight, it was just ours — a drink we could finally buy on our own and enjoy and not have to associate with the sexist trappings that held us back so long. 

In fact, Keith was not one to hold back at all. We kissed one another fiercely, letting our hands graze down each other’s bodies, and he finding his hands over my ass. It wasn’t a secret, clearly, and while I felt those around us gave us looks of surprise and wonder, I was more distracted by the growing bulge in Keith’s pants. 

“Hey, guys,” said a student frosh leader a few years older than us. “We don’t care if you’re gay, but if you’re gonna fuck you might wanna take it inside”. 

I pulled myself off Keith, and looked directly into the eyes of the authority figure, and said, “You know what? Let’s do it.” 

Hand in hand, Keith and I left the quad and found our way to the nearby residence building. Since I shared a dorm room with a “straight” jock — I’ll save the tales of my adventures with him for another time — we headed straight to Keith’s for more privacy. We walked up the four flights of stairs, right past his residence assistant, and into his room. I could smell the newly cleaned wood on the walls, which Keith had already skillfully decorated with posters of cut men in tight underwear. 

Ever since I was a teenager I had found the idea of muscular men in tight underwear sensual. I never could have imagined that on my first night in my new life that I'd find myself with the real thing.

“God, this is hot,” Keith said to me in a low, controlled voice as we made our way on to his bed. 

“I’m so glad we ran into each other,” I said timidly. 

Keith leaned in and kissed me, slipping his hand under my shirt. I didn’t yet have much chest hair yet, but he found what little I had starting to emerge. I was about to explore under his shirt when he pulled it off and then tugged mine up over my head as well. I kicked off my sandals and dove my face into the furry chest in front of me, the musk of his soft, dark hair entrancing me, urging me to take more. 

Keith moaned as I slowly bit down on his nipples, even louder as I ran my hands up and down the sides of his chest. I continued to entice him with my hands and teeth, with the brush of my subtle facial hair inviting his boner to grow even harder against me. 

Then Keith leaned over and pulled me on top of him. He began to massage me from outside my clothing and then urged me to take off another layer. 

I wriggled out of my shorts and at Keith's invitation, I lied back on the bed. He then began to touch my hard-on through the tight red briefs I wore, before kissing it from the outside and reaching around to tease my hole. Never having experienced this type of intimacy with anyone before, let alone a more experienced guy who knew what he was doing, I moaned with abandon. Keith grinned, knowing that I was about to be shown the magical first time of my life. 

Keith then stripped off his pants, down to a jock strap. I’d seen models wear them before but this was the first time seeing one up close. He turned me over and rubbed his groin into my ass. I shivered with the excitement and newness of it all. Keith massaged my shoulders and kissed my neck, and grew even harder. He plucked at the band of my underwear. 

“Can I take these off?” he asked in a calm voice. I nodded that he could. 

He slid his hands down into my underwear and then pulled them off completely, giving him full access to my body. 

I always kept my pubic hair nicely trimmed, and I could tell that Keith appreciated that when he rolled me over to take all of me in. Then he dove his face in, licking the area around my cock and smiling as it stiffened. Keith moved me around again, so he could put his hands under my ass, which he massaged with the same skill he had massaged my shoulders. 

“You’ve never had a blowjob before, have you?” said Keith curiously, with a tinge of excitement in his voice. 

“No, not yet,” I admitted. 

Keith squeezed my ass and said, “I’ll be your first.” 

I almost panted when he put his soft lips on my cock. Keith first circled my head with his tongue, which sent shivers down my spine. As I moaned, Keith moved in deeper. He opened his mouth wide and ran his beautiful tongue all around my cock, holding it by the base steadily. I moaned again, with a crack in my voice I hadn’t heard in a long time. Keith looked up at me as he sucked me with his big beautiful eyes, and gave me the look of a trusted friend. 

I nearly cried when Keith took his mouth off my cock until he began to stroke me even harder, skillfully working my foreskin up and down with his hand. 

“I want to see you have your first orgasm from another man,” said Keith breathy with excitement. 

I grew stiffer in his grip, and knew that soon I would orgasm. Keith pulled me in even closer and as he stroked me with one hand, he laid a finger underneath my balls and touched me ever so gently. I orgasmed in that moment, ejaculating on to Keith’s furry chest as he commanded my cock in that direction. 

While I came down, Keith lay his head on my chest and sighed satisfactorily. I didn’t know what to do from here. Luckily, Keith took the reins again for me.

“Want to help me rinse me off?”


Keith pulled me up, and led me to the shower of his washroom. He turned on the water, and pulled me in after him. As the water came down, Keith kissed me, sliding his hands all over my body. He poured soap into a loofah and rubbed me down, and then did the same to himself. We were both giddy, having met another boy so soon after arriving. 

Everything about that moment really was truly magical.

When we were done the shower, Keith handed me a towel to dry off. I looked at my clothes.

Should I get dressed? I wondered. 

Keith finished drying himself off, put his jockstrap back on and climbed on to the bed. I wasn’t sure if he was inviting me to stay over, but when he beckoned me towards him with a single word — “Come.” — I moved quickly and without hesitation. Just as suddenly, he said, “Stop.”

I did so immediately, worried — had I done something wrong? 

But Keith got off the bed, opened his dresser, and gestured for me to come closer still. He put his arm around me and pulled the drawer open with his other arm. Inside were many jockstraps of different colors. 

Keith fished a mesh one out, and said, “Put this on.”

As I rubbed the fabric in my hands, my heart rate began to climb again and my cock twitched, excited that this first night with Keith was far from over.

“I want you to see you in your first jockstrap.” 

It elevated my ass and made my member look even more generous — a perfect fit. 

Keith and I walked to the bed hand in hand and he turned off the light.

Also by Timothy:

My New Master


Written by
Timothy Bishop

Timothy Bishop is a certified travel consultant by day and lover of tender smut. He can usually be found at your nearest red wine location.