Being Not Gay with Jimmy 03 (Patreon)

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Chapter 3: Sweatpants

It was a stupid thing to fight about.

My favorite sweatpants had been missing for about two weeks, and I had already mentally retraced every place they could be before I remembered Jimmy had borrowed them after a workout when he forgot his change of clothes. I texted him about it and he said he had given them back, which I knew was wrong, and I said so, and he doubled down, and I got annoyed. The sweatpants weren’t even really the point, but I had committed to the position, and I guess my stubbornness won out.

“Fuck you” was the last text I sent before we didn't talk for three days.

Three days sounds short, but with the frequency we had been hanging out and “doing our thing” it wasn't. We had been getting together for the gym and hanging out afterward basically every day for a few months at that point, and the absence of him was on my mind. I was depressed, and it was weird, and masturbation basically lost its fun instantly.

I went to the gym without him, thinking about him the whole time while I lifted heavy things toward my head. I kept picking up my phone to show him something out of instinct, then putting it back down, sighing internally. I got frequent boners the whole first day, thinking about what we could be doing if he would just apologize and admit he lost my sweatpants.

Then I developed a new problem.

It was only the first day without Jimmy when I realized that jerking off alone had started feeling insufficient. It had crept up on me between waking up and skipping my usual mid-day wank. The regular method of spanking it felt like it was missing an element, like I couldn’t get over the finish line. Still, true to my routine, I pulled it out in a bathroom stall at school, and rubbed myself down until I dribbled out a light amount of goo. The lack of volume proved that this just wasn’t doing it for me. It symbolized that I needed an escalation of some kind, something with more going on, and without Jimmy around I had to improvise.

I don't know what made me think of it, but with enough boredom and pent up sexual energy, I came up with the idea that I needed to play with my ass a bit. I had always played with my ass a bit, just for fun, basically my whole life, and my hormonal energy had finally pushed me into thinking it was a sexual thing. I searched for something that seemed geometrically plausible, like it would fit in my ass, and I found it in the kitchen.

The cucumber was pretty close in proportion to Jimmy’s cock, which seemed fitting for some reason.

I brought it into my bathroom, got naked, and covered it in vaseline. Before I could talk myself out of it, I put a leg on my counter, my raging cock jutting to the side, shoved it into my ass.

The burn was strong, but I kept it in. Something about knowing Jimmy’s cock was the same size made me maintain in my head that it was possible to take this, and that I shouldn’t give up. Not that I ever expected to take Jimmy’s cock, but I knew that anal sex existed, and the girls in those videos seemed more than happy to take one, or even two large shafts inside them at once. So there couldn’t be anything wrong with shoving a Jimmy-sized cucumber up my melon hole and stretching myself out. Plus, even through the tension, I honestly liked the feeling. Maybe all those years of playing with my ass was time well spent after all.

Due to my determination and rubbing my cock vigorously, it eventually worked considerably better than expected. I blew a fat load that squirted onto the mirror, and slowly pulled out the vegetable, breathing hard, happy that I had made a new discovery. 

I tried a few other things over the next couple of days. A particular shaped shampoo bottle. This utensil from my kitchen that I cleaned very thoroughly before and after. I told myself that I was not thinking about Jimmy. I was thinking about escalation of my sensations. These are different things.

On the third day I was in my room with the cucumber again. It was probably the last day that I could use it, and honestly I was getting bored with the anal explorations. I missed my friend.

Acting on impulse, I took a picture of my ass with the cucumber halfway in. I was kind of surprised when I looked at it. My hole was stretched open like a pussy in porn. My brain did a backflip.

Then, not really thinking about what I was doing, I sent it to Jimmy.

My heart raced as I watched the screen. I know I could’ve “unsent” it, but a heart appeared on the message almost immediately. I smiled big, feeling suddenly overwhelmed with emotion. I stared at the hearted pic for a minute, then he sent a text.

“Come over”

—[]—

He met me at his front door. His mom's car was gone. He looked at me for a second, and I looked at him, and the three days of not talking to each other sort of disappeared in an instant, at least for now.

We said what’s up and went downstairs, sort of half smiling the whole time, like we were getting into something naughty.

He sat down on the couch and I sat on the other end and we were quiet for a second, back to normal. I put my feet up on the couch, next to him, and slowly slid them closer to him, before I pressed a foot into his crotch, feeling that big dick on that small frame that I had gotten accustomed to.

Then he said, "If you like that stuff." He paused. "I mean, from that pic. It wouldn't really be gay for me to just… give it to you."

I looked at him.

He looked back, completely sincere, working through his own logic in real time.

"Just to see what it feels like," I said.

"Yeah," he said back, "exactly."

I turned to face him slowly, feeling myself pulse below my waist. I used my foot to push at his waistband, and when he pulled his shorts down himself, I lifted my legs up. I pulled my shorts to show my ass. I didn’t say anything, just letting him approach me. 

When he crawled toward me on his knees, I watched his impressive manhood bouncing in the air, throbbing and ready for action.

He grabbed my legs tentatively, letting his dick touch me. I grabbed it and aimed it at myself, and he pushed in quickly. 

The initial sting was stronger than the cucumber, but the sensation of a real dick was very different. He leaned forward and pushed in further, and I held his hips, holding him back. I was lucky I had gotten used to vegetables, and that I was already lubed up today, because he didn’t seem very keen at holding back.

I held his body as I let him into me slowly, inch by inch, until he I felt him pressing against my stomach from the inside.

“Fuck, dude,” I said with an exhale.

“Dude,” he said above me. “It feels so good.”

“I like it too,” I said, watching his face as he looked down at the penetration. 

He pushed a little harder, somehow getting into me another centimeter or so, and for some reason that’s what made me yelp.

He ignored my response, and started humping. I held his ass, like I was trying to slow him down, but it did nothing to stop the furious humping. 

He grunted above me, feeling the first penetration of his life, while I was lying there getting fucked by my smaller, hung friend. 

I just looked down and watched as his impossibly thick shaft disappeared repeatedly below my balls, bracing until it started to feel really good. So much better than the cucumber. There was some magic about someone else doing it for you, and the dick was a better shape. I thought about how I might get a girl to do something like this with me someday, but the thought passed as I embraced what I had in the moment. Jimmy was everything I needed.

“Can you jerk me off?” I said. 

He grabbed my dick without hesitation.

“Fuck, it feels so good,” I said, “You’re gonna make me cum, dude.”

He stroked me while he humped me, going faster and faster like a rabbit. My legs tensed and I almost pushed him away on accident when I crossed over the edge, but he pushed back and got balls deep in me again, pushing the nut out of me. 

I don’t know if he did it on purpose, but I was aimed at my face, and I caught a couple streaks across my open mouth before I streaked the rest across my abs and shirt. He gave another couple pushes into me before he paused and exhaled. 

“I’m cumming dude, I’m cumming in you. I’m sorry.”

“No, it’s cool,” I said. “It’s better.”

After, we lay there for a while without talking. The basement was quiet. His mom still wasn't back.

"Okay," he said eventually.

"Yeah," I said.

He went and got Gatorades and we put the streamer on, and I took the weighted blanket off the back of the couch and pulled it over both of us, and we watched for a couple of hours. I kept a hand on him, feeling like we were the closest friends in the world at that moment. 

Suddenly, I remembered about the sweatpants.

I went up to his room without saying anything, and I found a pair in his closet that I knew he liked, the grey ones he wore to workout in a lot, and brought both back downstairs.

I brought them into the basement and held them up. "These are mine now."

He looked at them. Looked at me. "Whatever you want, daddy."

I felt something move through me. That joke went a little far.

—[]—

After that, we continued “practicing” together, getting ready for sex with real girls, and we even kissed a few times in the heat of the moment.

It was a weird thing, and I can’t really explain it. But “practice” is the only word for it that makes sense to me. We were both virgins, and we were curious, and we had already established a working situation, so we just kept going. He helped me figure out what I liked. I did the same for him. When I eventually got with a girl for the first time, which happened about four months later, I was considerably more prepared than I would have been otherwise, and Jimmy was the first person I called after, and he was happy for me in a genuine way, and that was that. Of course, he wanted his “taste” afterward, and I let him lick me down.

He got with a girl a few months after me. I was the first person he called too.

We still hang out when we can. He's at a different school now, so it's not as often as before, but when I see his name on my phone I always get excited, and when we're in the same place it picks right back up, the same as always. He's still got the baby face. He's gotten bigger from the workouts. He's still terrible at talking to girls, but he makes it work sometimes, somehow.

I don't think about what we do and feel weird about it. It’s just something we do, two best friends figuring stuff out, and it has made us closer, and I'm glad it’s a thing.

Even when I’m with a girl, Jimmy's my favorite person. I don't need to explain it more than that.