The scene on day two was an abomination. Two, straight, virgin, Catholic teenagers touching each other's cocks. For both of us, it was the first time either of our dicks got attention from someone else. Nobody had wrapped their legs around me like this. God had sent floods over this sort of behavior. Luckily, bodies are only programmed to feel blinding arousal or guilt at any given moment. Not both. In that moment, Rob and I were committing a mortal sin and we couldn't even feel it. We could only feel the pleasure that we gave to each other's greased up flesh poles. A surprising and sexy turn given how much I hated Rob the day before.
Day 1
So before my next experience with a man at 28, I had one blip with a classmate at the Catholic retreat for seniors at my high school. It was so long ago and followed by such a long hiatus from men that it often doesn't register for me. I was 18 at the time with a stocky, athletic build from soccer and football. My skin was tan from hanging by the pool with friends. I was straight, I was Republican, I went to mass every Sunday, and confession twice a month (none of these hold true today). So basically I was a good, hairy, little Catholic boy that jerked off twice a day.
The retreat was up in the woods at a compound that had a dozen 4-person cabins. The layout was dorm style where a bathroom split the two rooms of the cabin. Each room had two twin beds and the entire cabin was made of paper-thin walls. This was one of the only trips my mother let me go on because it was religious in nature. Needless to say, I was beaming when I arrived. Some of my buddies were on the retreat and I was praying they get my cabin.
My heart sank when I saw Rob approaching our porch. He didn't look happy to see me either as we mostly tried to ignore each other back at school. Rob was a huge ween. While I was starting to realize that I had been indoctrinated, Rob was notorious for being one of the more sheltered kids in school. He was a 6'1 swimmer who was a big part of the swim team state championship. He had a lanky frame, was completely smooth (from shaving for competitions), and had a ridiculous bubble butt. Of course, I only registered the physical features of men at this time as more of a comparison to my own. Rob had flowy, blonde hair, and a strong jawline. Somehow, God had let this objectively attractive guy become a huge dweeb.
Rob took the bed that was maybe 3 feet apart from mine as we heard Harrison and Patrick take occupancy of the other room. Rob opened up his duffle and pulled out a toiletry kit. He threw it on the joint nightstand and pulled out his toothbrush even though we hadn't had dinner yet. Classic Rob probably brushed 4 times a day. When he came back from the bathroom, I noticed that he had a vat of petroleum jelly in his bag which got my young brain laughing.
"What?" Rob said already irritated by my presence.
"Petroleum jelly, dude?" I prodded.
"What? I have to use it for swimming or my skin gets too dry."
"Mhmm." I said with disbelief.
"What else would I use it for?" Rob asked earnestly.
"Jerking off. Obviously." I was worried that I was letting on information that was weird about myself. On more special bate sessions back home, I would take a little dollop and go to town. Never too much so my mom wouldn't realize it was missing.
"You can use it for that?" Rob asked without a clue.
The meal chime played and we left to eat dinner. Tonight was supposed to be about settling in so everyone retired early. I laid in bed staring at the ceiling in the dark. I couldn't sleep because I was still horny thinking about Rob's petroleum jelly. After a few minutes, he had a consistent sounding inhale/exhale so I pulled out my cock from my pajama pants. I let my hand ride the cock train under my covers which slowly moved.
"You asleep?" Rob whispered to me.
Jesus! My heart jumped and the shame set in. Fuck. I decided the best course of action was to play it cool.
"Just gonna jerk off." I whispered back. The cabin was quiet and any noise would carry to our neighbors.
"Oh nice." Rob replied also trying to play it cool. I found his comfort sort of weird. After a few moments, I gripped my cock again. The blood had run out from my fear, but pretty soon I was working with a hard 6.5 again. The sheets of my bed began to rise and fall again. I glanced over to Rob in the dark whose face was intently aimed at my bed sheets. Rob must have realized that it was weird to just watch and his covers began to move. The fucking voyeur kept watching.
"Hey, can I see what you're doing?" He asked in a low voice. This seemed totally out of character from the guy who used to rat people out for cursing.
What a fucking weird request. I had never jerked off in front of a guy, but I had heard stories of dudes doing it. I was beyond horny and excited from jerking off in the vicinity of anyone who was aware. For someone as this inexperienced, this was the biggest thing to happen...ever. Without really understanding that you have to clear your head before making decisions horny, I replied, "Uhhh, sure I guess." Rob ran and turned on the light. He covered his exposed cock which waddled back and forth. He jumped back into bed and covered up. His size looked a bit ridiculous attached to the immaturity of his motions, like a big oaf.
I ripped the covers off my cock which was covered in glistening precum. It was so engorged that it pointed straight up. "Oooo," Rob said. I don't think he meant to say that. "Dang, Warren, you have a big dick." I guess he did.
"Thanks," I replied. Very quickly it became awkward to be jerking off with a spectator who was hiding. "Rob, you have to jerk off as well. If I'm going to show you, then it's only fair." Rob pulled the covers off and revealed his 5.5-inch, cut cock. I was excited that I was bigger than this much taller guy. Mainly, Rob sucked so it felt like I had something on him. A few moments passed and Rob just oddly squeezed his head. He was watching me with so much interest, like he didn't want to miss a second of what I was doing.
"I've actually never really jerked off before." Rob confessed.
"Wait, what?" I said surprised.
"Shhh. Well, like I have squeezed it, and it felt good. But nothing has really happened." He replied. I was shocked. How had this 18-year-old never watched porn, or jerked off. I was astounded, but he said it with so much embarrassment that it had to have been true.
Too horny to really consider the punishment of teaching someone how to commit a mortal sin, I went straight into a lesson, "Dam, okay. Well first off, don't squeeze. Grab your cock like this." My hand closed around my dick. Rob copied. Now, just go up and down. I began to stroke and he did the same. Rob began to leak. "Smear some of that on your fingertips. Now, rub it on the underside of your shaft." Rob groaned. "Shh. Good, now focus on the underside. That's what will make you cum. There's a part just below the tip that should feel really good if you rub it." I wasn't ready to cum, but my cock was so engorged that it felt like it was going to physically explode. I grabbed myself hard. The harder I squeezed my cock, the more relief I felt. Rob was breathing heavily as he explored his new meat toy. He looked up every few seconds to watch me.
This was the hottest I had ever felt to date. My 18-year-old brain didn't know it was the presence of a man that was escalating the way my body was reacting. It was just another jerkoff session that happened to trigger ALL of my arousal. I started humping up into my fist. "Now, the harder you grip and the faster you stroke, the quicker you'll cum." I added. "Like this." I clutched my cock with a vice grip. I needed to release the pressure immediately. I looked over at Rob who still had his eyes wide like he was witnessing a miracle. His breathing was shallow and he had started to stroke like I taught him. The scene was too much new stimuli. The orgasm started deep. I had to suppress every urge to scream out. The cabin neighbors would definitely hear.