But It's Better If You Do

I was just finishing up another set of VYou answers, and Phil came in just as I completed the final one. “Hey Phil, want to watch over these with me?” I set them all to play, and he laughed, until we got to the last one.

The question had been, "Do you masturbate?" which I had answered truthfully with "Who doesn't?" Phil stiffened in his chair.

"Well, what did you think?"

"T-they were great, Dan." Phil stuttered, shifting uncomfortably in his chair. There was a moment of silence and Phil blurted out, "I don't."

He flushed hot pink and looked at me expectantly. “Well I’m not going to film them again, they took forever. I know they’re not great quality or whatever, but come on Phil.”

Phil cut me off. “No, uh, that l-last question? I don’t.”

My eyes widened in shock. “Um, what?” I looked over at him to see if he was joking, but he looked incredibly embarrassed. “Why... not?”

Phil rambled, “Well I didn’t when I was a kid and now I don’t know how and I don’t know I need someone to like tell me how and maybe like you could I don’t know this is stupid.”

“You want me to teach you?” I smiled, it was unbelievable that someone older than me didn’t know how to do things I’d been doing since an embarrassingly young age. “I’ll teach you, but not here.” I shut the screen of my laptop and took Phil’s hand in mine, leading him to my bedroom.

I set him at the edge of my bed, thinking of how I could turn him on. I sat behind him on the bed, and laced my hands around to unhook his belt to slip his pants down his legs. I took his hand in my own, lacing my fingers into his so that when I moved my hand over the bulge in his boxers, his palm moved with mine, guided.

I pressed my head into the crook of his neck. “Step one,” I whispered, breathing hot and humid at the soft skin just behind his ear. I ghosted our hands over his slowly growing boner, and when I applied slightly more pressure, started to become rhythmic. He bucked backwards, inadvertently grinding his ass against my own crotch. Once he was hard, I hooked my thumbs into the elastic band of his underwear and pulled it down.

I reached under my pillow - yes, I’m quite gross, judge me all you like - a grabbed a bottle of lube, and squeezed a bit into Phil’s hand. I breathed hot air into his ear and whispered huskily, “Step two,” I wrapped my hand around his, and together we moved, pumping slowly. Phil shuddered. and I could feel goosebumps forming on the tops of his thighs. He pressed back into me, and I quickened the pace, waiting until he was nearly on the edge. I slowed, and whispered as drawn out as I could.

“Step. Three.” I lifted him so he sat partially on my lap, legs still dangling off the bed. I coated two fingers with what remained in the tiny clear bottle and pressed up gently into Phil. He whimpered, and I used my free hand to continue to pump his dick. I could feel his body tense up, and I kissed his neck, pumping him faster to remind him of better things. I knew it was his first time, there was honestly no point unless I found his - oh. I pressed my fingers upwards once more, feeling his body go slack against mine as a little mewl flew from his lips. I hit it again and again, sliding our hands up and down his shaft, and finally, as his legs started to shake, I ran my thumb over his head, and I hit his prostate once again. He moaned shuddery and high as he came over our hands. I shifted so that he sat on the bed and I stood, my hands dirty but otherwise looking the same as I had before we’d started.

“Something like that, yeah? Oh, and clean up before you leave, Phil, I don’t want to sleep on that.”