True story how I faked getting caught jacking to finally get my friend to jack with me.
In my freshman year of college a group of friends and I would often go out of town to watch our football team play. This weekend it was just James and I. When we got to the hotel they did not have a record of our reservation. The only rooms they had left of course were ones with single queen size beds. James and I said that would be fine.
We dropped off our bags in our room and headed on out to the game. It was late when we got back and we were tired so we took quick showers and headed straight for bed. Now I usually sleep naked, James and my friends know this, but James is more of the modest type so in difference to him, especially since we were sharing a bed, I decided to wear a pair of briefs to sleep in. I was still sitting on the bed in my towel when James came from his shower in his towel. I noticed though, that there seemed to be a bigger bulge then normal under his towel.
As he removed his towel to put on his own briefs I definitely noted a much plumper dick than is his norm. I could feel my dick take notice. James is a beautiful guy, he's my height at 6'1" sandy blond hair, an athletic body with long legs. He has short curly blond hair on his chest that runs into a dense happy trail that ends in a small patch of short blond pubes above a heavy four inch free swinging dick and nuts. I stood and dropped my towel and started to step into my briefs when I noted a surprized look on his face. I looked at my dick and saw it was plumping up some but still behaving so I looked at him and asked "What?". He asked me when I started sleeping in underwear. I told him I hadn't but since we were sharing a bed I didn't want him to feel uncomfortable.
He blushed a little bit and said ok. Did he seem... disappointed? Did I just miss something? I pulled on my briefs and laid down on my side of the bed. James finished pulling up his briefs over a nice chub and laid down on his side. I thought to myself "Maybe he wanted me to stay naked. I wonder if I can get something going here?" It was fairly warm in the room so there was no need for cover. We talked for 30 minutes about our girlfriends, about the lack of sex, (his girlfriend was his high school sweetheart and a virgin!) and how "we had to do for ourselves". Each time we started getting detailed he got nervous and changed the subject. During a lull in our conversation I noticed a change in his breathing. He had fallen asleep! As I laid there thinking about my near miss I noticed his breathing changed, his eyes moving under their lids and his fingers twitching, he was dreaming.
His dick started to swell, it crept under his briefs up toward his right hip. His dickhead enlarged and become more defined under the fabric. Soon his ever growing dick had stretched the briefs tight as it pushed against the elastic band of his underwear. I stroked my now very hard dick through my briefs as I watched his cock flex in response to his dream. I had an idea and I thought to myself, "I may yet get to jack his dick tonight." I pulled down my underwear to my thighs and moved my right leg up against his leg and started to slowly stroke my dick and move my hips in rhythm to my jacking.
James's breathing changed again. I knew he was awake, I could see his eyes open to just a slit as if he were still asleep. I played with my nuts as I continue to slowly jack. I milked out some pre-cum and spread it around on the head of my dick. James's dick flexed twice and I noticed a small wet spot starting to come through onto his briefs. I whispered "Damn James, that's one hard dick. You must be dreaming some good shit". At the sound of his name his eyes came open a little more and he looked at me. I said "hey dude, I'm sorry man, I didn't mean to wake you but I couldn't help it. I woke up with this hard dick and just had to start stroking it." He told me no problem. I nodded toward his dick and said that he must have been dreaming a good one too. I asked him if he wanted to join me. He hesitated only a moment and said "sure".
We pulled our briefs off. I thought this guy was beautiful before but his dick was perfect. It had to be a good 7 1/2" to 8" long, a thick straight shaft that was topped with a large pink bell shaped head. I pulled out a small bottle of lube from my bag and put some in my hand. I asked him if you wanted some, he said sure, so I reached over with my hand and spread it on his cock. He inhaled sharply but made no move to stop me so I started to stroke his rigid cock. James seemed to want this but there still seem to be some hesitation...... A thought came to mind and I asked him, "Has any guy ever jacked you off before?" he said no. "not even a buddy?" He said "Nobody, not ever, not even my girlfriend!" What?! He saw the look on my face and said "For real John, I'm starting to think she might be gay." Umm, What do I say to that?
I couldn't believe that I was the first person to touch his dick, to Jack this beautiful cock. He leaned his head back and softly moaned as I slowly brought my hand up to the top of his dick, giving two short strokes than a long down stroke to the base of his dick. As I continued to stroke him he started moving his hips, moving his dick in my hand to rhythm of my strokes. I told him "dude, I still can't believe I'm the first person to touch your dick, you've got such an awesome cock!" He laid his hand on my thigh and asked me if he could touch my cock. I told him whatever he wanted to do. He put some lube in his hand, reached over and picked up my cock. He started stroking me without much pressure or rhythm, like he was afraid to touch it. I told him to relax, to treat it like it was his own dick. He adjusted his grip and started to stroke my cock. I watched him, watching himself stroke his first dick ever, my dick. He lifted my balls in his hand, letting them move across his fingers as he continued to stroke me.
I started to move my hips to match his stroke. The feel of his hand on my dick and nuts was unbelievable. I could feel the pressure building quickly in my nuts. He seemed to become ever more excited, intensely focused as he watched my dick swell to its fullest, the veins hard on my shaft and my dickhead dark and shiny with the pressure. His fore head creased and his hips began to thrust harder into my hand as he watched me approach release. We were both so close now. Our thrusts were a split second apart, our hands slapping against each other's nut sacks, slap slap, slap slap. I felt my cum empty into my dick. My dick spasmed as I gave a last hard thrust into James's hand and yelled out "James I'm there, Oh shit James, awwwww!! Cum exploded from my dick in a huge shot that landed on James's hand, forearm and my chest. My cum was still in the air when James sounded a loud groan. His hips pushed up and his dick spasmed hard in my hand as his cum lifted into the air to come down on my hand, arm and chest, again and again, cum shot after cum shot erupted from our dicks to cover us until we were utterly drained. As we caught our breath and cleaned ourselves up with their towels I smiled at him and asked "Well?" He softly laughed and said "that was totally fucking awesome!" I totally fucking agreed.