"You coming, Rich? We're going to that Lebanese restaurant around the corner."
"Yeah, sure," I smiled as we filed out of the little basement room after our meeting. I'd tried several different AA groups but I stuck to this one, mostly because it met on Friday evenings (the most triggering for me) but also because the people happened to be the friendliest. For the first time in a very long time, I actually had something resembling a social life. Who would've thought I'd find it here of all places?
Just then, the neighboring meeting came to an end as well and the people started coming up. That's when I saw him.
"Caleb!" I shouted out. He saw me, smiled, and started walking up toward me.
"You guys go ahead," I turned to my buddies. "I'll meet up with you later."
"Richard, hi," Caleb walked up to me and gave me a hug. The fact that he even remembered my name gave me butterflies.
I hadn't seen Caleb in a few months. I never saw him at Dr. Martinez's anymore. Even though his Sex Addicts group met next-door to my AA meeting, Caleb didn't seem to be a regular and I rarely bumped into him here either. He looked different; he had grown a scruffy beard.
"Happy New Year," I said, even though it was almost spring. "Are we still saying that?"
"Sure, why not? Happy New Year," Caleb seemed to be glowing.
We chatted for a while, until the crowd around us had completely dispersed.
"Would you like to have some coffee or something?" Caleb asked me. "There's that coffee shop we went to last time."
"I… I'd love to."
I never liked Lebanese food that much anyway.
Walking with Caleb past all the other couples, gay or straight, who were out on dates, felt inevitably romantic. When we sat down at the coffee shop, I texted my brother to let him know I'd be out later tonight, and I turned to Caleb to continue our conversation.
"I haven't seen you at Dr. Martinez's in a while," I said. "Did you switch to a different time?"
"I'm… not seeing Dr. M anymore."
"Things kinda got… complicated between us and we agreed it's best if I see someone else."
Coming out from a meeting where you were encouraged to be brutally honest, I felt like I should speak with honesty now as well.
"I know," I admitted. "I… overheard you."
"What?" Caleb seemed surprised.
"I hope it's not awkward. It was right before the holidays. I forgot my phone at his office and when I went back to pick it up I heard you two… having sex."
Thankfully, Caleb laughed. He looked down at his cup for a couple of seconds, before looking me in the eyes again.
"Yeah. That was the last time I saw him," he said. "The next day he emailed me and apologized for everything, which I found unnecessary 'cause we both made it happen. He recommended a list of other therapists and refunded everything I paid him."
"That's… probably for the best," I said awkwardly. Then, something inside me told me to reach out and take Caleb's hand in mine. Luckily, when I did so, he didn't pull away.
We held hands for the most part of the following thirty minutes, until we finished our drinks. When I said I was planning on taking a cab home, Caleb offered to drop me off.
"Listen, Richard," Caleb said just as I was about to leave his car, parked in front of my brother's building. "I'd love to get to know you better. If you ever wanna… hang out or anything, hit me up."
I smiled. The fact that this man, who I considered to be so far out of my league, would ask me that, made me feel ecstatic. Then I remembered Dr. Martinez saying that I shouldn't think of myself or others that way. And he was right.
"I'd love that," I replied to Caleb, moving in just a few inches closer, hoping that he takes the hint. He did, and we kissed in his car. And the butterflies were back.
Like many other Fridays, I was done with work early. I texted Kimi, and she suggested we go for a walk in Grant Park. Going for a "walk in the park" wasn't my usual idea for a date, but I accepted. And I'm glad I did.
It was a lovely afternoon. The weather was finally nicer, and everyone seemed thrilled to leave the Illinois winter behind. As we passed an old man selling balloons, I stopped to buy Kimi a heart-shaped one. It was by far the cheesiest thing I've done, possibly ever, but it made me feel young again.
I was really falling for this woman. Maybe it was the fact that we did things like go for walks in the park instead of fucking, which was my go-to activity, but I was really developing feelings for her. There was still plenty of uncertainty. Kimi had sucked me off a few times, but we never went further than that, not just yet.
That was a part of the reason why I had asked my brother if I could jerk him off. I wanted to know what dealing with another person's cock felt like. I knew it wasn't the same, but I wanted to be prepared. Weird or not, I was lucky that Richard obliged. I was lucky that my brother and I had gotten close enough that we could do stuff like this, and things still wouldn't be awkward.
When I got back home, it was still early in the evening. My brother had sent me a text saying he'd be out later tonight. I took my clothes off, and realized the red briefs I was wearing were Richard's. I hadn't noticed it this morning; they must've gotten mixed up in the laundry. But these were the sexy briefs I put on when I went to his apartment by myself. The day that I found…
"I wonder where he keeps it?" I snuck into my brother's room and started searching. I remembered the black dildo I found that time. Now that I was curious, I wondered what it'd feel like to… try it out. Richard was gone for the evening, something that never happened. So if I were to do this it had to be tonight.
Feeling like a criminal, I snooped through my brother's stuff. Until finally, I found a box in his dresser that contained a small collection of sex toys. The largest thing in the box was the dildo.
"Fuck, how do I do this?" I said to myself out loud. It was rhetorical; I knew what to do. Although no one has really played with my hole yet, I'd fucked plenty of women up the ass. It was the same just in reverse, right?
I took the bottle of lube that was also in Richard's box and I lubed up the dildo. "Here we go, I'll just try," I told myself. Doesn't matter how much I can take. This is just a quick test.
Doing it while squatting seemed the easiest way to take it. I got in position and went ahead. The initial feeling was.. weird. Not particularly nice. Kinda painful. I stopped and realized I should shower first if I'm gonna do this.
I hopped in the shower and washed my ass as well as I could. There was lube sticking to the hair that I had growing between my cheeks (that's one problem I'd never faced when dealing with women). I washed, toweled off, and went back to Richard's room.
"Okay, take two," I said out loud.
I tried sitting on the dildo again. This time, I felt more prepared. I gritted my teeth and ignored the pain. "This is actually quite manly," I thought. I mean, what's manlier than being able to take pain and ignore it and take it like a champ?
Then suddenly, I started laughing. I looked down at my hairy body, squatting on my brother's dildo on the floor in his room. This was kinda ridiculous, but I… I could make it. Little by little, I felt the toy go up my ass. Holy fuck, I was really doing this!
In that moment, I learned two lessons. Once: I could take more up my ass than I thought I could. And two: when my brother said he'd be "back later," he meant only half an hour later than usual. Unexpectedly, he bust into his room and caught me, half of his dildo sticking out of my ass, the other half inside of me.
"Holy shit, man!! Are you okay?!"
For fuck's sake! I thought today would go down as the day Caleb and I potentially started dating. Nooo, Patrick had to one-up that. It would go down as the day I caught my straight brother fucking himself with one of my sex toys.
"Is this what you do while I'm gone?!"
"No, Richie, this is the first time, I swear," my brother said. I found it interesting that he used my childhood nickname again.
"Then whatever you do, don't pull it out too quick!"
"I don't think I could if I wanted to. This… feels weird. Interesting, just weird."
"Do you… want me to leave?"
"No stay," Patrick said. "This is an experiment."
"What kinda goddamn experiment?!"
"Don't use the Lord's name in vain!" Patrick quoted our mother in the same tone she would use, and he and I started laughing. Sure, that was the real issue with this situation.
I stood in my room, fully dressed. Two feet in front of me, my older brother was still squatting on the floor naked. I thought I could see him bouncing up and down just a little as he sat on the dildo.
"So this is what you're… experimenting with?" I said.
"Yes. Can you help me with something? I wanna try this on all fours, but I don't want the dildo to plop out. Can you go back there and hold it for me?"
Holy fuck, whatever my brother was going through, he did not give a fuck anymore.
"Why couldn't you get a sports car if you're going through a mid-life crisis? You do this instead. Hold on," I said and I started taking my jacket off. It was too hot in here, and what I was seeing only made it hotter.
I got on my knees behind my brother. I put my left hand on his ass, and my right hand in the center of his back.
"Now bend down slowly," I instructed him, and felt him start to go down. With my left hand, I held the dildo in place until Patrick got on all fours, hands and knees.
"Now bark!" I joked.
"Woof, woof," my brother played along, making us laugh again.
"How does that feel?" I asked with genuine concern.
"Okay. Kinda dry."
"Hold on," I said and reached for the bottle of lube. I squirted some at the tip of his asscrack and watched it drip down between his hairy cheeks. I also got some on my hand, and used it to lube up his hole around the dildo.
"I'm not gonna lie, I'm impressed," I admitted. "This is your first time? This isn't a small toy. You got half of it in."
"Really?" my brother sounded proud of himself. "Do you think you can push it in a bit further?"
Was my brother really asking me to fuck his ass with my own dildo? Our parents truly were rolling in their graves.
"Hold on," I said, and continued to take the rest of my clothes off. I was hot, but also: I was hard. My erection felt painful inside my jeans, and I needed to get rid of them.
Just to be safe, I squirted a bit more lube around Patrick's hole. I knew my brother had a hairy ass, but I'd never seen it up close. Now, I spent a while rubbing it, right between his cheeks. In part because I wanted to rub the lube in, but mostly because… this felt nice. With my nose basically touching his ass, I got a real good view as my brother's hole pulsed around the dildo.
Sweat dripping from my armpits, I started to push the dildo in. "Ahh!" Patrick moaned, arching his back. It didn't sound like a yelp of pain. He seemed to be enjoying this.
Slowly, I pulled the dildo out just an inch, before pushing it back in again.
"Is it going back and forth?" my brother looked back and we made eye contact.
"Aha," I nodded. "Can you feel that?"
"Fuck yeah I can," he smiled proudly.
"Should I keep going?" I asked, still pushing and pulling the dildo back and forth, little by little.
"Yeah, just for a little bit," Patrick said and faced forward again. He arched his back further and stuck his ass out like a true hungry bottom asking for more.
I held the dildo by its rubber ball sack and pushed it in further. By this point, it was three-quarters inside my brother's ass. With plenty of lube now, it was making a sloppy noise as it went in and out.
"Do it a bit faster," my brother asked. This was obviously his competitive side, testing to see how much he can take.
"If you say so," I obliged and started speeding up, more and more until Patrick begged me to stop.
"Okay, okay! You fucker," my brother chuckled. I slowed down and went easy again. Looking down, I realized my boner was dripping precum all over the floor. And that is when I thought to look at my brother's cock. I bent down and took a peek between his legs.
"You're hard," I noted.
"Holy shit, yes I am," Patrick reached between his legs and grabbed his boner with his right hand. "It just sort of happened."
I watched my brother jerk himself off while I fucked him with the dildo. For once, I felt like the pro in the game we were playing. I knew exactly how to do it, fast then slow, deeper then almost all the way out, teasing Patty until his furry thighs started shaking.
"Holy shit, is this what this is like? I could get used to this," my brother panted, jacking his cock quicker and quicker. I thought of us as kids: Patty teaching me to play soccer. How to throw a baseball. And now here I was teaching him the pleasures of anal sex. And he was taking to it like a duck to water.
With my free hand, I rubbed my brother's ass before moving down to his taint and then his balls, giving them a few tugs and making him feel even better. But I couldn't ignore my own cock any longer. I wrapped my hand around my boner and started stroking myself at the same pace as my brother.
Faster, and deeper. The dildo was almost all the way up my brother's hairy ass. His legs shook, and he started to grunt loudly.
"Holy fuck, I think I'm gonna cum!!" he shouted, then let go of his own cock. He arched his back and stuck out his ass as far as it would go. I picked up speed and shoved the last inch of the dildo inside Patty's hole.
"AHHHH! FUCK, YESSS!!"
My brother was shooting his load on the floor, handsfree. He pushed his ass out, begging me to go as deep as possible. I shoved the dildo in until its balls were touching Patrick's.
"Ahhh," Patrick continued to cum like a horny beast. I couldn't believe my eyes. I took a deep breath, and I started shooting my own load, my left hand tightly wrapped around my cock. I stroked it fast and saw my jizz shoot out and land on my brother's ass. It was a large load, which dripped down his cheeks and kept going down his thighs.
When we were done cumming, it took us several minutes to calm down. Very slowly, I pulled the dildo out. There was a jizz rag in my box of sex toys, and I used it to wrap the dildo it, before putting it aside and looking at Patrick's ass.
I was facing my brother's gaping hole, a sight I never thought I'd see. It pulsed, lube and cum glistening on my brother's ass. It was still wide open, so it took two fingers and stuck them in, as if to say "Good job!"
"Mmm," Patrick moaned, still breathing fast as if he'd run a marathon.
"I…" he tried to catch his breath, as I fingered him for a couple of seconds. "I think I owe you dinner after that."
Patrick and I had a surprisingly normal dinner after that. We took turns showering, before sitting down at the dinner table. My brother told me about his developing relationship with my former neighbor, and I filled him in on the prospect of dating Caleb. After dinner, we played video games for an hour before I started yawning and headed out to my room.
"Hey, Richie," my big brother yelled after me. "D'you wanna share a bed tonight? Just so?"
We brushed our teeth and both lay down in his bed naked, cuddling up. We were both exhausted, and it felt lovely to have someone to hold onto. Again, it brought back memories of doing this as kids.
"Night, Patty. I love you," I whispered. It felt like the right moment to say it.
"Night, Richie. Love you too," my brother hugged me tighter, gave me a soft kiss on the cheek, and drifted off to sleep.