Practice with Randy
Once I learned how to do it, all I wanted to do was masturbate, but I had my instructions from my teacher, so, after work was finished on Thursday, I went to the suite to meet up with Randy. We had our meetings twice a week and today was one of them. He also mentored five other boys, so often his meetings ran back-to-back. Today was one of those days. When I arrived to the room, he wasn't there. I waited around for about 15 minutes until I got really bored. Then, I started to look around the room. I had never been so bold as to look through his drawers or under the bed until now, but that is exactly what I did.
When I got to his sock drawer, I found an album of pictures, all of different boys he had mentored through the years with dates, events, and quotations as captions underneath the picture. It made me begin to wonder – how old was Randy? I wasn't, by any means, a mathematician, but I figured he had to be at least 30 based on the years and the photographs. I looked through them and saw a picture of my cousin Alex back when he was a skinny, scrawny runt like me with his arm around Randy, kissing his cheek. It was a nice picture and, for a moment, I wanted to steal it and show it to Alex, but I knew that would be wrong, so I kept it where it was.
When I searched under the bed, I found an old shoebox full of blank electronic disks. I wasn't sure if they were CDs or DVDs, but either way, there was nothing identifiable about them; however, for some reason there did seem to be an order about the mess of them, so I tried to keep them that way as I pulled the top one out and popped it in the DVD player. There, right in front of my eyes, was a younger Randy completely naked, sprawled on the bed. His legs were closest to the camera, dangling over the ends of the mattress, his balls were hanging low and his cock was standing hard and straight up enough to hide most of his chest from view. His eyes were on the camera for a while, hunched up by his elbows to control the remote to the video camera.
Then, his hands ventured down to his shaft and began stroking. Intermittently, he would look at the camera as he slowly stroked. What was funny to me was that Randy did it differently than Coach Vester. Coach Vester used his entire fist and held strong around his entire penis, while Randy played with this piece of extra skin that hung out just under the head. He stroked and massaged that little piece of skin with two fingers and then stroked again. He had a rhythm to it like he was an expert, as I am sure he was by then. Based on the video, I ascertained that he could not have been any younger than 26 or 27 when he did the video as he didn't seem to look all that different, though I hadn't really seen him aroused this way before.
As I watched my mentor stroking and massaging his penis on the video, I began growing inside my shorts, so I reached in and grabbed ahold of my own cock, holding it hard and squeezing with all my might. I watched carefully as the Randy in the video made eye contact with the camera and smiled. Oh, the way he smiled, it made my penis jerk on it's own. I couldn't only squeeze it anymore, so I pulled down my shorts and briefs and let it hang out, my bare ass feeling the coolness of the floor below me. I decided to try and copy what Randy was doing in the video and shivers went all through my body and I found myself closing my eyes and grunting. Once I got the pace down, I was able to lead back against the mattress in front of the TV and repeat the stroke-massage method over and over.
I was so enthralled in the pleasure I was getting from watching Randy in the video and playing with myself that I didn't hear the door open and I didn't see Randy standing there watching me.
"I see you've found my stash, huh?" He smiled.
Shocked, I jumped up and pulled up my shorts and briefs and plopped down on the bed.
"IÉamÉsoÉsorry!" I said, out of breath, still feeling the tingling in my body.
"Oh, no!" Randy began, "don't be. I enjoyed watching. In fact, I'd like to watch you finish. Isn't that your homework anyway?"
Randy seated himself next to me and let his eyes gaze on the television screen. He put his arm around me. Without saying a word, he was confirming, between the two of us, that we both ought to feel comfortable. Then, he yanked at the edge of my shirt and helped me pull it up over my head. Then, he yanked at my shorts and I removed them completely. I looked over at him, deep in his eyes. In fact, I could feel the sexual tension between us as my member throbbed in anticipation.
Randy made no move towards his own growing member under his shorts. I could tell, by the shape of his growth, that he was wearing a different kind of underwear than usual and I stared at his crotch with a questioning stare. He recognized it and smiled slyly at me before he tugged at the elastic band of his nylon shorts and gently pulled them down, revealing a speedo underneath. The crotch of the speedo snugly hugged his banana-shaped penis.
"I went swimming earlier" he said, as we both stared at his crotch. Then, he looked over at my member and gave me a sweet, endearing smile as I slowly enjoyed the sensations that made my body feel like melting. There was something so sensual about pleasuring myself in front of Randy. Maybe it was because I thought of him as an alternate father or maybe because it was just somebody at all, but either way, when he looked into my eyes as my palm slowly made it's way up and down the length of my three-inch dick, I felt at home.
Randy let me go on that way for several minutes, his own penis raging underneath the tight, red material of the speedo. Then, he stopped me by grabbing my hand, though intentionally not landing his hand on my penis.
"Okay, you need some help." He smiled. It was true. I felt pleasure but I didn't feel it the way I think I was supposed to and not the way he was feeling it in the video, so I invited his help. "Here," he said as he pulled my open palm up to his mouth and then spit into it. "This will help make the feeling better and more intense."
I proceeded to watch the video, feel the heat of Randy's almost-naked body next to me, and let the slippery feeling of my palm massaging my member sent shivers through my spine.
Although I think Randy wasn't supposed to do it at that point in the lessons which Coach Vester had set up, he instinctively pulled down his speedo and let his seven inch cock pop out like a jack-in-the-box. Once it was there, staring me down, I couldn't take my eyes off of it. I loved every element of it. I admired how the skin was darker the closer to his abdomen his shaft was and lighter the closer to the head. I loved how his pubic hairs popped out like grass underneath a towering tree. I admired it and he touched it lightly.
"If you really want to masturbate correctly, you have to completely explore your body." He said. Then, he propped himself up on the bed and began running his palms all over his body from his head to his legs, spending most of his time lightly massaging his inner thighs and scrotum. Then, he turned over and let his hands work on lightly massaging his backside; however, I could tell he had a hard time reaching it.
I couldn't tell you why, but I stood up, my soldier at full attention, staring at the back of my mentor, his smooth slender clenched butt cheeks and I offered him my hands. I climbed onto the bed, my knees settled next to his and I ran my finger nails against the skin of his back. I mapped out every freckle he had, every mole, ever dry patch of skin, every smooth patch. I played with the valley that was his spine and ventured even further down his back until I was flirting with his ass. Then, he stopped me.
"No!" he protested but in a moan, the way someone protests who wants something really bad and can't say no but has to say no. I backed down at first and showed my disappointment.
"Sorry." I began to dress as I got up from the bed.
"Look," he said, "I just don't want to rush things. Mr. Vester has a specific curriculum where you learn about others' bodies and explore them. He tells you how to and teaches you the value of loving another man or boy's body.
"But," I began to protest, "I think I get it." I paused and looked at him, sprawled on the bed, twisted in such a way that I could see the light-colored hair that surrounded his hole and I could see the red head of his penis peeking out from the sheets. "I know it's more than just pleasure."
He thought for a moment and considered the situation. I was sure he had many opportunities to explore with boys, so this wasn't as though it would be his only chance. In fact, his other "meetings" may have been sex sessions with some of the older boys he still mentored; however, something in his eyes communicated with mine and said I understand.
And with that, he invited me back on the bed and instructed me to explore only with my hands.
I massaged his whole backside and when I reached his butt, I felt the contours with such detail I felt if I closed my eyes, I could draw it with precision. I let me index finger run up and down his crack and tingle the little hairs that sprung out. I heard him moan in pleasure and I allowed my other hand to go to my own cock and massage it. Then, I ran my fingers down his inner thighs. I don't know if it was reactive or intentional, but Randy spread his legs so I could see the pink button that was his asshole staring at me. I looked at it the way the Coach had looked at Todd's. I looked at how the tight skin swirled and stretched. I let me fingers work their way in to the pink and swirl around it. I kept touching myself, finding that the more I intruded his body, the more aroused I was and the more I sensed a feeling building inside of me deep down.
"Keep goingÉ" It was all Randy said as his face was buried in the pillow and he raised his butt further in the air towards me and stroked his own cock. I licked my finger, thinking it must work the same for this as it does for masturbating – it was obviously pleasuring him. "Go inside," he said, "and keep stroking yourself."
I did exactly as I was told. I sped up my motion against my cock and I let me index finger slowly slide into Randy's hold, feeling a warm tight pressure against my finger. I wanted to keep it in there and feel the warmth that was the inside of my closest friend's body.
Then, out of nowhere, I felt a surging in my body as I continued to stroke myself. In invited it. I could feel my body tensing up and my face turning red. "Are you cumming, baby?" Randy asked, as he sped up himself and his sphincter clenched my finger even more.
"Yeah" was all I could managed before my body began to tense up and my cock throbbed with intensity, bringing all the sensations I had felt to a pique. I whinnied as I came and Randy groaned as he himself came onto the mattress with my finger still inside of him.
For a while, we both remained in those positions, catching our breath. Randy, of course, felt remorse. He felt he had done something wrong and he felt bad that he had dirtied the sheets; however, when he sat up and looked at me, we both could only manage to smile at each other. Then, Randy leaned in and kissed me on the mouth. "I love you, kiddo" he said, as he patted me on the head and tapped me on the butt. Then, before I knew it, he was heading toward the shower and all that was left of our lovemaking was the thick white puddle of cum on the bed sheet. I watched the mirror in the bathroom to see if he was watching, which he wasn't, and I leaned in and sucked every drop of cum off the sheets until it just looked like a water stain. Todd had said it tasted like candy; however, Randy's was warm and tasted salty. Nevertheless, when I closed my eyes and let his sticky goo make circles around my tongue, I loved how it tasted. It was his, after all.