(Smut) Phil is new at prostate stimulation

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I'd been masturbating for a long time about 11 years in fact because I started at 17. But it's always been the same, wrap my hand around my cock, tease my thighs, sometimes tweak my nipples, but it was just a routine now. I wanted it to be fun, not a chore. I heard from of my mates that they had tried fingering themselves and found it enjoyable. Of course this was with several pints and I'm pretty sure they are all straight so I was still surprised to find them admitting to doing it. I should try it, I mean, how hard could it be?

I grabbed my lube that I hid under my mattress, most people have it under their pillow or even on their nightstand but I was very private when it came to sex. I slowly started stroking my thighs, tweaking my nipples, getting myself hard, the same old stuff. Then I poured lube on my two fingers and sighed, "it's now or never." I shoved them into my hole and howled with pain. Then I heard it. The quick footsteps, and the knob turning. "Phil what the hell happened?!" Dan spoke before he saw me. His eyes widened when he saw my position. My heart raced, what the hell was I supposed to do? Ow! My hole hurt like hell, I groaned as I pulled them out. Dan's face went from shock, to confusion, then realization. "Phil is it your first time trying this?" Dan walked over and sat on the edge of my bed, concern in his eyes. I nodded, freaked out, of course Dan saw me naked before, but not like this. Dan signed. "Mind if I give you a few pointers?" I couldn't respond my eyes wide.

"Ok, first off, when its your first time you're going to need a lot more lube." Dan grabbed the lube and started putting it on my pointer finger. "You ALWAYS start with one finger, unless you already stretched earlier in the day." Dan started moving my finger and slowly pushed in. "Start off slowly and build up your speed after you add more fingers." Dan put lube on my middle finger and pushed it in. Eventually it started feeling actually kind of pleasurable. I bit back my lip, trying not to moan. "Phil, it's ok, I know this is kind of weird but you really should know how to do it properly. You can moan." Dan lubed up the last finger and pushed it in. I started panting and letting out little shy moans. Suddenly Dan pushed them in a little father and at an angle. It felt amazing, "Dan, oh fuck!" I saw Dan smirk a little. "That, my dear Phil, is your prostate. Just hit that a couple times and you'll be cumming in no time." Dan started to get up to leave, leaving me to finish on my own. "Um, Dan, will, you, stay?" I asked between pants, blushing somehow more than before. He gave me a 'look' but sat back down on my bed. He snuggled up to me and started sucking my neck. "Oh, Dan! Damn! Fuck that's good!" I started hitting my prostate as much as possible, eventually cumming on my chest.

I grabbed a tissue and cleaned myself up. I turned to face Dan. "Um thank you. That was um, well, the best wank I ever had." Blushing furiously. Dan giggled, "I don't think there was actually a lot of wanking. I hope the kissing wasn't over the line." Dan looked down. "No it was fine, it's been a long time since I got that much attention." I smiled sadly. Dan looked up and lurched onto me. His lips were rough in certain places which I'm sure was from him biting his lip. I laid down on my back so that he was on top of me. Eventually I pulled away for air, "I think we should talk later." Dan nodded and mumbled against my neck, "But later is not now, now we should kiss."

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⏰ Last updated: Jun 23, 2015 ⏰

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