[M]->[M/M] Curiosity, Sated; Part 1 | 2016

This is a story of recent experiences with a close friend of mine, but all things start in the past. This part will be a bit of a precursor, detailing the story of discovering what I want to try with him. If people end up liking it, I'll go on to detail the rest of our experiences so far. If not, ah well. I tried. :D

So, for a long while in high school I thought of myself as straight. I'd always been a very, very shy guy when it came to talking with girls though, actively avoiding it with a heavy blush if things ever steered towards dates and the romantic. But one thing I'd never really thought about were other guys.

Highschool lunch is when I met him. The first time I'd ever even seen or heard of a gay guy, and he sat in front of me every day. It was the beginning of my curiosity about gay guys and the things they'd do to each other, a curiosity which wouldn't go away. Over time, I began looking into it, stumbling across things that made me outright squirm in my seat for reasons I didn't know yet. Anal sounded disgusting and dirty, but... Intriguing. There had to be something to prostate stimulation for them all to enjoy it so much.

It happened in the shower soon after. Hot streams of water slowly coursing down my side, curling and tracing along my body as the thoughts came back to me while I enjoyed a hot little bit of self-pleasure. What would it be like? To have something gently pressing against my rear, stretching it, slowly sliding inside..? My hands paused as I bit my lip. If any place was good to try it, the shower would at least have the easiest time to clean.

So I prepared. I leaned over, taking the shower head from above me and directing the hot water between my cheeks, shivering softly as it massaged my sensitive little pucker, cleaning it gently. One hand slid back to caress and grab a cheek, pulling it open as my thumb twitched the lever on the nozzle. Suddenly the showerhead gurgled and blasted a much stronger stream hard against my ass, making me shiver and nearly drop it. It felt surprisingly good, powerfully peppering the ring of muscle. As nice as it felt, though, I had other things in mind...

Stepping forwards and placing the showerhead back above, I gently bent over again, bracing my body against the wall. Over the past few weeks I'd done quite a bit of research, stumbling across information about how to best do anal, what it felt like... Slowly, I rubbed a finger against my cleaned rear, pressing the tip gently into the ring of muscle. I could feel it flex and stay quite closed as I gently rubbed it around, getting used to the soft sensations and pressing slowly, very slowly, ever deeper. Soon I'd managed a small amount of penetration, gasping as I sank in to the first knuckle. I shivered and flexed around it, feeling the tight walls squeeze close. It felt wonderful, my shaft slowly twitching and eagerly leaking more pre than I'd ever seen... I had to have more.

My finger came back out slowly, then returned in a flash with a bit of spit and pre. In it went, pressing bolder now, slipping in and gently but insistently fighting the convulsions of my tight little hole to press deep. In and in it sank, making me quiver slowly. It wasn't long before another finger joined it. Then another. A third, fourth... I was lucky to have the house to myself. I was taking ages to enjoy this. But it still wasn't enough. I loved the feeling of the fingers slowly stretching me as I sank down on them, the fullness of it, the way the pressure hit just the right buttons on my prostate... But it still wasn't enough.

I glanced around and noticed a small white bottle. Small, however, was relative: It was very small compared to a shampoo bottle. To my eyes, it looked just right. As thick as six fingers, a gentle rounding to it's base edge. Perfect. I grabbed it and slicked it up, the water still spattering away behind me in the tub, slowly loosing heat.

It wasn't long until the fat, blunt end was pressed tight against my somewhat-stretched hole, making me quiver anew. I shifted to press down on it, bracing it against the tub's bottom, nearly moaning as it stretched my entrance, hard. It hurt, but felt so very, very good. What felt even better came moments after, when the whole fat thing slid deep past my sphincter and filled me up just perfectly. I could feel every little quiver I was making around it, could feel it pressing hard, hard against my prostate. As much as I was shaking, I didn't dare press it in and out... But I did take time to enjoy it deeply. I had the hardest orgasm of my life up to that point soon after, and nearly collapsed in the tub. No wonder they loved prostate stimulation so much...

Weeks later, I tentatively picked up my phone, and shyly texted my friend. I wasn't sure where this curiosity was heading yet, but... If anyone knew, he might.