I had a good feeling about his interest. I would comment to raise his interests and curiousity. I had a plan to find out more. I used the base of all my mutual masturbation encounters. Porn. He had a very conservative family and no access to porn I figured. I invited him for a weekend with the intention of pushing the boundaries. I waited till on the way to my house to tell him something. I wanted to gauge his reaction. I told him of the tall stack of porn mags I had to look at if he wanted. I saw him thinking and asked if he wanted to see them. He answered with enthusiasm clearing the doubt. I watched him stew thinking of porn. He had never seen any porn before. I kept the movies for more leverage to use at the right time.
We ran to my room lockin it behind us. I pulled out a tall stack to my buddies amazement. His eyes bulged at the sight of so many to look at. He began to flip through them from cover to cover. An hour later he had gone through the stack twice. I know he was horny and ripe to move forward. I asked if he saw a xxx movie and got another no. I told him I did and watched his eyes light up. I told him I had a condition in order to watch them. I told him it was what I had to do to watch it my first time. It had to in the nude. He hesitated and told him that was the rule. After agreeing he asked to be naked under a blanket. I agreed figuring it was a start and could work on it during the movie. I stripped nude to get the most time naked with him to reassure him. I hoped my nudity would put him at ease and peak his interest. He giggled as I walked and bent over naked in front of him. He stripped under the bkanket.
I sat on the bed and him at the foot of my bed. He sat at eye-level with my penis and saw it everytime he looked back at me. I laid with my hands behind my head. I was horny and kept going from hard to soft. He kept a good eye on me and noticed my growing and shrinking cock. We talked about the girls and sex for an hour or so. I felt he was ready to work on losing his covers. I told him he should be out in the open like I was. He didnt need to hide cause I was cool with him being naked. I pulled on his cover and he mildly resisted as I removed his blanket. He said his dick was small and was shy. I took a long look and saw nothing wrong with it. It was small compared to mine but assured him it was ok. I told him to move on the bed with me. He sat timidly on the bed. I could tell he was a bit nervous. I told him to sit and relax like I was. If we touched it was fine with me.
He sat beside me with our legs touching. He kept his attention split on the tv and my dick. He spent more time on my cock the longer the movie played. I saw his cock rock hard the entire time. I got out the vaseline to lube up offering some. I had a sudden idea to make a move. He wanted some lube and I got some and rubbed it all over his dick. I felt him tense and twitch as I ran my hand over it. I told him I was cool with touching his dick and cool with being touched. I saw the wheels turning now. He seemed to be more focused on my cock. I kept a hand on my cock just to draw his attention. I planned to pave the way and see where it went. I left the game open for him to decide what happens. I soon got a response to my actions after talking about past same sex experiences. He was now certain and sprang into action.
He wanted to give me a dick massage. I said ok and couldnt hide my excitement, instantly hardening to his touch. I got hard nearly throbbing in his hand being so horny. He touched and explored my cock from base to tip. He stroked and looked me over up close and personal. He played with and praised the size of my balls. He played awhile before making his next move. In comparison I was scared and uncertain in need of coaxing. He on the other hand was confident and sure of himself taking the lead. He asked if I wanted my dick sucked. He said he has done it before and was willing to again. He told me how an older boy use to have him suck his dick and knew how. With that he wrapped his lips around my cock sucking it like a bigstick. He needed no guidance or convincing and knew what he wanted to do. He sucked and stroked my penis with skill. It wasnt long before he had more ideas for me. He wanted to sit on my dick. He rubbed a good amount of lube on me. He faced away from me straddling my lap. I was between his cheeks as he bucked back and forth. I slid between his ass as it pressed against me. I stopped him to keep from cumming.
After a breather he grabbed and sucked my dick. He wanted to sit on my dick again and told him I wasnt ready to cum and would stop him before I did. He bucked back and forth making me moan and groan. I began to stop him and saw he wasnt ready to. I told him to go ahead and make me cum. He slyly smiled at the chance to finish me off. He began to move with the purpose of making me cum. He moved faster and firmer atop of me. I began to gasp deeply and announced my pending orgasm. I was squeezed and rubbed between his cheeks to orgasm. My first squirt filled his ass up until it came shooting from the top of his ass. I heard the squish grow louder with every spurt. It shot halfway up his back. I laid with my cock in his cheeks and sperm pouring out his ass. It was a huge orgasm and felt drained.
We stayed naked and later he pressed his ass against me making me stiffen up. He began to mount me and grind on me. After awhile he began to suck and stroke my cock. He expressed the desire to make me cum again. He spread my legs nestling between them to suck my dick. He would sit up as he switched from his mouth to hand. As he stroked me and sat up our dicks nearly touched. He noticed too and tried touching them together. He made them touch trying to get more leverage on me. He closed my legs and had me on my back knees and feet together. He straddled me able to press our dicks directly against each other. It felt good. I told him I might not cum again after the massive one earlier. He must’ve took this as a challenge. He moved grinding atop me with passion to please. I felt his dick rubbing my dick pressed between our bodies.
I felt a tickle as an orgasm built up in my cock. I began to moan out I was gonna cum again and to keep going. He began to press harder against me and move faster. I grunted as I released. I felt our crotches go slick and heard as it grew louder. It covered our stomachs and groins. He kept moving a few minutes after the last squirt, well past my orgasm. I shuddered as he kept grinding and sighed still spinning from the intense orgasm. He hopped off admiring his handywork. He was so proud of making me cum twice. Two huge orgasms!! It was the start of a longtime relationship.