Thanks for coming back for Chapter 2. I’m trying to retell the story exactly as it happened, which is why I’m not rushing straight to the climax (pun fully intended). Hopefully you’ll stick around.
I checked my phone multiple times the next morning, hoping for a text from Shawn. I knew he wouldn’t be up as early as I was. A teenager on summer break isn’t waking up at 6 to work out before hopping on his computer by 8. To say that I was distracted the next morning would be an understatement.
I barely slept the night before from the sheer excitement of having seen him mostly naked. His cock looked great, and he had willingly shown it to me. Sure, he was getting advice about which size condom to buy, but still, he got himself hard and walked out of my guest bathroom so I could tell him what he needed.
My motives were mixed. Sure, I wanted to help him get the right condom for his big date that was only a couple days away. However, I had also been curious about what he was packing. The fact that he asked me about condom sizes just happened to work out perfectly for me.
The hours dragged by the following morning. Shawn and I chatted back and forth a lot, so it wouldn’t have been odd for me to text first. Still, I wanted him to initiate the conversation. As I sat down with a sandwich at my desk around noon, my phone finally dinged:
“Hey Tommy. Think I can pester you again?”
“Sup Shawn? You never pester me.”
That was true, finally. When he was younger, he was an absolute pain in the ass. Maybe it was him maturing, perhaps it was my newfound attraction to him, but now, he was certainly never a bother.
“I got those condoms you told me to get. But man…I have more questions. Can I come by?”
“I’ve got a virtual meeting at 12:30. Can you get here around 1?”
“I’ll be there.”
This meeting was already a roadblock in my day, but now, I resented its existence more than ever. I wasn’t sure what he was going to ask me about, but I was confident in my ability to convince him to go as far as he had gone yesterday.
At 1:05, he walked through the door without knocking as usual. I didn’t mind. I had been waiting for his second visit for days. Much to my delight, he had a box of condoms in his hand.
“Not even trying to hide those, huh,” I chuckled.
“Didn’t figure I needed to,” he said, tossing the box toward me. It was open.
“Wait a minute…I thought your date was in a couple of days. Have you already used one of these? YOU DOG!” I was genuinely happy for him.
“No. But I was…um…well, I wanted to put one on so I didn’t look like a total loser when the time came.”
“Ahh gotcha. So, what’s the question?” I truly had no idea where this was going.
“Well, I did something wrong when I put it on. I tore it. Definitely not trying to have a kid,” he looked somewhat embarrassed. To be honest, I could understand why. Putting a rubber on isn’t difficult, but I had to remind myself again of his naivety.
“Ok, so what’s the question? You said you needed to ask me something.”
“I mean…can you show me how to put one on?” He seemed nervous.
His anxiety in asking made me hesitate. I wasn’t trying to force anything on him. I just thought he was a great looking guy.
“Man, you can find anything on YouTube. Hell, don’t they teach you this stuff in sex ed? We had a teacher put one on a banana when I was in the eighth grade.”
His laugh broke the tension of the moment.
“Tommy, I watched a couple videos, but I obviously did something wrong. I don’t even know what.”
“Well alright. Let me go find something in the kitchen to put one on.” I wanted him to stop me. I did not want to throw a condom on a banana to teach a lesson to an 18-year-old. Seemed like such a waste. I came back empty handed after hiding the bananas that were lying on the kitchen counter.
“Tough luck. We don’t have any bananas or cucumbers. You wanna run to the store and grab something?”
“I kinda hate to do that. I mean, can you just show me with one of yours?” He was sheepish in asking, which only made the moment cuter.
YES! I knew I needed to hide my delight, but it wasn’t easy.
“That’s not gonna make things weird for you, right?” My question was at least somewhat genuine. But I was really hoping he didn’t rethink his request.
“Nah. You’ve already seen mine. Only seems fair, right?” I swear to God, he winked when he said it.
I quickly ran upstairs to the bedroom. I opened the drawer beside the bed where my wife and I kept all of our “special items,” and pulled one of my condoms out. I was already getting hard, which was going to be difficult to explain. I tucked it down as much as I could and made my way back downstairs. Shawn was still sitting on the couch.
“So, I guess I need to do something to get it up. Should I take my phone and go somewhere like you did the other day?” I was leading him a bit, knowing that I wanted this to go a certain direction.
“I mean, you don’t have to. I figured if you’re gonna show me how to put one on, we’re both gonna need to…you know.”
“Get hard?” The words were out of my mouth before I could stop to make it seem like I didn’t want this.
He chuckled and nodded.
I went to my go-to site on my phone and set it on the coffee table in plain view of both of us. In the name of total transparency, I should admit, I didn’t watch much of what was on the screen. I was too busy watching him slide his hand into his shorts and start massaging what I knew was down there. My cock was growing when I caught him glancing over at me. Perfect.
“So, you ready to try to put one on again?”
“Do you think I could watch you first?” There was a slight grin that came across his face; this was going perfectly.
I stood up and pulled my shorts down. For as unshaven as he was around his crotch, I was completely smooth. My wife, his sister, preferred it that way, and I was happy to oblige. However, while his entire upper body was smooth, I am quite hairy. I’m in relatively good shape, and love working out. So, while I don’t have a dad-bod, I certainly have the hair of a stereotypical bear.
“Whoa! You shave everything down there?”
“Yea, you don’t want to know why, bud.”
He didn’t look at my face when I responded. His eyes were firmly locked on my throbbing member, and I was fine with that. I gave it a couple good tugs just for his viewing pleasure.
My bare ass sat on the leather couch as I unwrapped the single rubber that I brought downstairs. I put it on just like I had done plenty of times before, his eyes fixed on my cock the whole time.
“See, it’s pretty simple. Put it on the head and just slowly roll it down.”
“Can I say something and not freak you out?”
“Buddy, we’re sitting on the couch and I’m almost naked. You’re obviously pretty hard. I think we’re past freaking out at this point.”
“Your cock is fucking THICK.” He put a lot of emphasis on that word. My length lands somewhere between 6 and 7 inches, so I certainly don’t think my dick is anything remarkable. But it is pretty thick.
“Yours will fill out. You’ve already got good length. You gonna try to put one of those on now?”
He nodded, stood up, and pulled his shorts and underwear down. His black bush encircled his cock and balls. He sat down on the couch, a bit closer than he had been, and unwrapped one of his condoms with shaking hands.
“What are you nervous about, man? It’s just us.”
“I don’t know,” he chuckled. “This is just kinda wild. Never thought I’d be sitting here with my dick out around you with yours out.”
“Would you feel better if I got dressed?”
“Nah. You don’t need to do that.” His answer was a huge relief. I had no interest in getting dressed at the moment.
He awkwardly put the condom on the head of his dick, and inexplicably tired to pull it down by the sides. I had never seen anything like it, and I couldn’t completely hide my amusement.
“See! I already messed this one up too. It’s not torn, but I read online one time that if you mess up putting one on, you should just get rid of it because it’s not gonna work. I can’t do this Saturday night, Tommy! I need to look like I’ve got some level of experience. I’m a fucking 18-year-old virgin.” He was freaking out and I instinticively put my hand on his leg. He didn’t pull away, which I took as a good sign. He pulled the condom off, but his dick was still rock hard. So was mine.
“Shawn. Calm down. How many did you buy?”
“I have six. I bought two of the three packs. That’s all they had at the gas station.”
“Ok. So you still have four, and they have plenty more. Calm down and let me help you out.” I promise, I wanted to help him make his first time a good one. But I was also really enjoying the view.
I told him to get another one out, and he did. I knew this was my moment. I was going to try to take things to the next level of whatever this was.
“This is all still between us, and ONLY us, right?” He nodded at me. “Ok, do you want me to…put one on you. Watch my hand.”
“So like, you’re gonna touch my dick?”
I had gone too far. I knew it. He was going to freak out, leave, and tell my wife everything.
“Listen. You watched me put one on myself, but you obviously didn’t get it. What if you watched me put one on you? But man. If anything has ever stayed between us, this fucking has to,” I laughed to break the tension, and it worked as he nodded.
He unwrapped a third condom, his last one from that box and handed it to me. Now my hands were the ones shaking a bit. I put the condom on the head of his throbbing cock, and for the first time ever, I felt it in my hand. I had fantasized about moments like this one. I didn’t want to linger and make it too obvious, but I was going to enjoy the moment. With the heel of my hand against his shaft, I slowly unrolled the rubber down his dick.
“Now, I don’t want you to waste another one, so I’m going to just roll that one back up and you do it.” He could have done that part himself, but damn, I didn’t want him to. I needed another touch. His hands were at his sides as he nodded and gulped. I was sure he was enjoying this moment, too.
I pushed his pubic hair back and slowly rolled the rubber back up, returning it almost to its original condition. The skin of his cock felt magical against my hand. I left the condom on his head and nodded for him to do it himself. This time, he got it.
I smiled, he smiled, and then, we sat there. Neither one of us moved, both unsure of what to do next. We were two guys with rock hard cocks, condoms on. The porn continued to play on my phone. I decided to take my condom off, as it served no purpose any longer. He watched as I rolled it up.
“Whatcha staring at, Shawn?”
He jumped a bit as I said his name.
“Nothing, Tommy. Sorry. It’s just….nothing.”
“I know. It’s thick.” I laughed and he slowly rolled his condom up and shoved it into the box. He threw the box in his backpack as we both started getting dressed. I wanted more, but he obviously wasn’t ready for that. It’s OK, Shawn; I’ll keep waiting.