Story Prompts, Articles, and Ramblings - 1. I'll Never Wear Boxers Again

During my late teens and early twenties, one of my best friends in the world was a boy named Jason. I met him at Giant, a local grocery store chain where I had been working for four months, and we immediately hit it off and became inseparable.

I remember the very first conversation we had on that humid summer night in the parking lot of the grocery store. I was the front end supervisor, a position that mainly said I was a cashier but had the magic card that could offer overrides and had to ensure everyone received their breaks in a timely manner. Basically I was a shift lead.

It was on one such break the first time Jason and I hit it off. He was five-ten, 140 pounds, he wore glasses and had light brown hair that could turn blonde if seen enough sun. I was ready to go to break and asked Jason if he smoked, he replied yes but his cigarettes where in the car. I told him to run and get them.

I don’t know why this stands out in my mind, but the look on his face when I asked him to smoke with me is an image I’ll never forget. His face lit up and he smiled broadly and then took off running towards his car that was parked way out at the end of the parking lot.

We bonded over our love of movies, and by the time the break was over, I had invited him out to the pool hall after work to hang with my friends. From that moment on, we became known as Jason Squared.

Nights playing pool turned into bar crawls once we turned twenty-one. And after about a year, we picked Monday nights for our weekly night out. This night was for us, no other friends, no girlfriends, and no problems.

It was during one such pub crawl when I first told him I was gay. He took this declaration in stride; he didn’t much care what other people did or didn’t do behind closed doors. He was very progressive seeing as he came from the deep south. Though looking back over the events, I wished he would have showed more emotion one way or the other than the indifference he seemed to show at the time. It might have saved me a ton of heartache later on in life.

Jason and I had always been comfortable around each other from the very beginning. It was common for him to crash at my one-bedroom apartment for days on end. It was also common for us to sleep in the same bed, or should I say pass out as most of our nights ended up with us being hammered. Waking up with us snuggling happened so many times it wasn’t something that we thought or cared about.

Before I told him I was gay, we’d go on double dates, and the girls would often complain that we spent more time talking to each other than we did to our dates. It was often joked about in our circle of friends that we acted like an old married couple. I was a big part of his life, going over to his family’s house to celebrate holidays, births of nephews and nieces, for ten years we were inseparable. I guess looking back; it was rather obvious that sooner or later we’d start fooling around.

The first time it happened between us was after one of these Monday night pub crawls. It was after two am, and we had stopped on the way home from the bar at a gas station for cigarettes and sodas. Plus Jason, who probably to this day has the smallest bladder I’ve ever encountered, needed to go to the restroom for the twentieth time that night. I paid for the cigarettes and sodas and waited for him in the truck. And I do remember the look on his face when he climbed inside the truck and got behind the wheel.

He was almost always smiling, it was his nature, he was a happy person, but that night the smile on his face was different somehow. I couldn’t place it. And he was acting strangely on the drive home; he seemed nervous and giggly at the same time. Like he knew something I didn’t know and couldn’t wait for me to get the surprise. At the time, I just figured he was drunker than usual.

Once we arrived at my apartment, he started flirting with me in a way he never had before. For instance, while we walked to my apartment from the parking lot, he put his arm around my shoulders and walked with me. When I walked up the stairs, he grabbed my butt. While I fished for my keys in my pocket at the front door, he rested his head on my shoulder.

I will admit that all this behavior had started to turn me on. Of course I had been attracted to him from the moment I met him. But he was also someone that I identified as straight plus he was one of my best friends, I had long accepted the fact that it would never happen between us.

So after about twenty minutes of this weird flirting, I stood up and declared I was going to bed. And I’ll be honest, I wasn’t really that tired, but I really wanted to take care of my almost out of control libido in the privacy of my room.

I remember he stood up and looked down at the floor and asked in this quiet voice if he could stay with me. He didn’t ask if he could crash, he didn’t ask if he could sleep over, he asked, rather nervously I might add, if he could stay with me. And for a moment, a brief moment, I almost said no. I mean, I really wanted to jack off. But I could never tell him no, so I smiled and said sure.

In my bedroom, I took off my clothes and slipped into a pair of shorts. He walked in and asked if he could borrow a pair of boxers to sleep in, something I thought was really weird because he never wore boxers. He was a briefs man. I motioned towards the dresser and told him to help himself. He rummaged around in my underwear drawer for a moment and then said he was going to change in the bathroom. That was definitely strange as we had changed in front of one another lots of times.

But I climbed into bed and turned off the lights and the TV on. As I waited I mindlessly flipped through the channels not really looking for anything n particular. After a few minutes, I heard the bathroom door open and then heard his footsteps down the hall. I turned off the TV as the bedroom door opened and in walking this…glowing…thing right about waist level.

I don’t know about now, but back then, in most gas stations, in the restroom was condom machines that you could buy single use for a dollar. He must have bought one of the novelty glows in the dark condoms.

As I lay there in bed, I was quite taken aback but more than a bit intrigued. In the four years that we knew each other, I had never seen his…thing…out and proud as it were. I was nervous but managed to say something along the lines of nice penis.

Jason started laughing and flipped the lights on. He was standing there in my pair of boxers and had shoved three of his fingers of his right hand into the condom. He laughed and turned off the lights. Then he started walking towards me, his condom covered hand wagging before him leading him to the bed. I remember watching him walk towards me and I almost wished it really had been his…thing.

Once he reached the bedside, he started giggling again; I was transfixed, wondering what he would do next. And I watched in fascination as the condom covered hand moved to his right side. Then I saw the glow in the dark disappear from sight. I didn’t take me more than a moment to realize his fingers were inside the boxers he was wearing. For a moment, nothing happened. Then as just a hint of a glow started to show against his pale skin, I realized he was pushing down his boxers. This time it wasn’t his fingers, I could tell because once it freed from the confines of the boxers it bounced up and smacked into his stomach with a whack. And it was definitely better than his fingers.

He took another step closer to the bed, now he was only inches away from my face. He was so close I could smell him, a mix of body wash and his own natural scent that caused me to take a deep breath. The hand that was covered by the condom moved and the two colors merged into one. He held it straight out from his body, inches from me, and whispered, ‘do you like my surprise?’.

I didn’t answer, I couldn’t. I didn’t want to risk anything ruining this moment. But I reached out and grabbed the glow in the dark condom. He shivered at my touch. I pulled him over on top of me and we both started laughing. Needless to say, neither one of us got much sleep that night.

It was a few years later, in one of his more sober moments that he would admit that he had been racking his brain for months trying to find a way to seduce me. He had wanted to make sure I was interested in something sexual with him before he tipped his hand as it were.

Looking back, it was clear how methodical he had been in his seduction. There was the constant touching, him always wanting to sleep together, the invitation to late night drunken naked hot-tubing; it had all been done with the purpose to get me into bed. I asked why he didn’t just ask me if I was interested in him. Apparently, once, shortly after we first starting hanging out, I mentioned that I would never have sex with a friend as I would never want to risk losing the friendship for a night of fun. Apparently I had said that at the first party we had ever gone together.

Of course, I laughed. I remembered that party, and I remembered why I said that. There was this girl that had been trying to get with me for months, and since I had no interest in her, I informed the entire group, that I don’t have sex with my friends, so she would leave me alone. And it worked, she did. I wonder how much time I would have saved if back then I would have just told everyone that I was gay.

That was the start of our sexual relationship. I was completely head over heels in love with him and I know, no matter what he claims now, for a time, he was in love with me as well. But though he would move in with me a few months later, and stay for six years, he only thought of us as friends with benefits. Though we were inseparable and spent a lot of nights together in my bed, being gay was something he has always denied. He once told me, after we had went separate ways, that I was the only guy he had ever been attracted too.

It was a confusing time for me, on the surface, during the day, we hung out with friends, he dated multiple women, and I had numerous partners myself, but at night, when it was just us, we had this relationship that only appeared in the cover of darkness. There was real love there, spoken at times but always shown in the way we lived.

Our friends would later admit they suspected us but with the women he dated and all the boys I played with; it wasn’t more than a passing thought. And truthfully, none of our friends cared. Though our friend, Nelson, was a bit freaked out when Jason asked me to be the best man at his wedding. Nelson was one of the few people that knew about us, and the most conservative of the group. But he kept his opinions to himself.

One night, during those confusing years while we lived together, we had just gotten back from our Monday night pub crawl. We were pretty messed up that night, for some reason we had been playing a drinking game with the bartender and had more shots than usual. He had been dating this girl from one town over and I had been chasing this nerdy little boy I had met in the AOL chat room a few weeks earlier. This was one of those times we hadn’t fooled around for a while; he was in the midst of feeling guilty about being with me.

The moment we got home, he went into his bedroom, and I jumped online to see if nerdy little boy was in the chat room. He was, and for about twenty minutes or so, I was content to do some dirty chit and some salacious chat.

Friends with benefits or something more, ever since that first night we fooled around, we had established a certain set of rules for when we fooled around. Speaking for myself, I was always ready to fool around. The way he let me know he was horny and wanted to fool around was to walk around in a pair of boxers.

I had been chatting with nerdy little guy for about twenty minutes, when Jason opened his bedroom door and walked into the living room wearing a pair of brown silk boxers. He made sure I was watching as he walked into the kitchen and got a drink of water. Then he walked back and gave me a smile and then headed back to his room. As I stated before, I was always ready to fool around, and judging by the bulge in his boxers, this was one of those times that both of us were ready to go.

He made it clear what he was wanting, yet on the computer, nerdy little boy was almost ready to meet in person. I could feel it, we were so close. But then I looked into Jason’s room and he was lying on his bed with one hand in his boxers. I turned off the computer and ran into Jason’s room.

He smiled when I walked in and pulled down his boxers and put his hands behind his head, as if to say, go ahead, do anything you want to do to me. I attacked his crotch and for a few minutes, we both were enjoying ourselves immensely. When suddenly, he tensed up, sat up and started puking his guts out. I was sober enough to know what was about to happen so I managed to move out of the way fast enough where I didn’t get anything on me but he covered himself and his sheets. It was rather disgusting and definitely wrecked the mood.

Once he finished, I helped him to the bathroom and put him in the shower so he could clean himself off. While he was in the bathroom, I grabbed his sheets and put them to wash. I cleaned off his bed the best I could and then went back to the computer to see if nerdy little boy was still online.

He was, so we started chatting after I made up a stupid reason why I just disappeared in the middle of our last conversation. A few minutes later Jason comes out of the bathroom, freshly showered, his shaggy brown hair dripping in his eyes, and fully aroused. He smiles at me and walks into my room and jumps on the bed flat on his stomach. Needless to say, I never did get a chance to meet nerdy little boy.

Jason and I’s weird relationship would continue for years to come. While we were alone, locked up safe in my apartment, we would be together for hours. But we almost never talked about our night activities in the light. As I spoke before, we had dozens of unspoken rules we followed, silently and in secret until I couldn’t handle it anymore. To my memory, he never acknowledged our lust filled nights during the day in all that time.

But all that changed the day I met his fiancé for the first time. He had invited me out to dinner to meet her and we had been reliving some of our wilder times. At the time he called me to meet his fiancé, he had moved out for about two years and we hadn’t really spent much time together during that time so it was nice to catch up with him. After all, for ten years he had pretty much been the focal point in my life.

Jason was telling stories about our now famous Monday night pub crawls, and he gets this weird look on his face and tells the story of the time he almost puked on my head. Of course the first thing she asks is why we were in bed together. Unlike my usual quick witted self, I was at a loss of words, but he smoothly told a g-rated version of the story that seemed to make sense to her at least.

Later on, when she had went to the bathroom, he laughed and said the look on my face during the puking story was the best thing he ever saw. I didn’t think it was that funny, remember I was still in love with him and completely jealous of his fiancé. She was amazing too, which made it even worse.

But that changed when he leaned in close to my ear and said, “I know I can’t love you like you want me too, but sex with you is something I will always remember and no matter who I marry, you’ll always be the one that gave the best head.” Or it was something to that effect.

It was the first time I could remember him ever admitting to having sex with me while sober. But it was the right thing to say, because that statement convinced me to agree to be his best man. And over the next five months until the wedding, we did have a few more times where we all got together and relive those younger days.

The day of the wedding was the last time I saw him. He has now been out of my life longer than he was a part of it. Through mutual friends back in Pennsylvania, I hear he has two lovely daughters and has been married for 13 years. And I really do wish him the happiest of lives. And though our friendship has disappeared over time, I will always have the memory of that apartment and the time we spent there.

During the night I first met his fiancé, we somehow got on the subject of boxers. She mentioned that she prefers guys that wear boxers but he wouldn’t give up his briefs. Jason and I exchanged looks and started laughing. He pulled her close and kissed her on the mouth. “I told you, I use to wear boxers for a time, but I don’t anymore. And I’ll probably never wear boxers again.”

Three days after the wedding I moved from Pennsylvania all the way across the country to get away from Jason and his new bride. San Francisco was the farthest place west I could go and still stay in America. That’s what it took to get away from the memory and the regret. Because on the night before he promised to forsake all others, he showed up on my door with a bottle of whiskey and asked if he could come in. The night, before his wedding, he was wearing boxers.