My First Anal Dildo

Let me just start off by saying that getting fucked in the ass is addictive. I started in my early twenties, before I ever knew about femboys or sissies. I don't know why I started sticking my fingers into my tight virgin hole, I just know that at some point I was fingering my ass daily. I didn't know about prostate orgasms, and it was years later that I bought my first anal toy.

I don't know what I was thinking when I bought this thing, but for some reason I thought it would be a good idea to buy a humongous 12 inch long and 3 inch wide realistic dildo. I was so insanely nervous about buying it, as I wasn't "gay", but the feeling just made me all the more excited for it's arrival. I came home from work to a plain brown box on my porch, which I scooped up and ran into the house with.

Thirty minutes later I was in the shower, totally clean inside and out, when I placed my monster dildo onto the tub floor and began to lick and suck on the tip. There was no way it was going to fit, but I was determined to give it my best. The act of sucking that dildo had my little cock so hard, and my left hand was between my legs, lubing and stretching my eager hole.

I turned around, angling the dildo until I could feel the tip pressing into me. I began applying pressure, feeling it's giant head stretch me out. It began to gurt, but I was close and didn't care anymore; the urge to fuck my asshole was so intense that I pressed back harder, despite the pain, until I felt the head of the dildo pop inside of me.

I was so full that I thought I would break myself. I leaned forward, letting my shoulder and face rest against the tub as I slowly and carefully moved my hips up and down. Instantly I could feel my little cock go from hard to nothing but a small little shriveled thing, and looking back between my legs I started to feel a pressure building in my pelvic floor. I began to shudder a little, unsure of what was happening.

The pleasure came unexpectedly, roaring from my prostate to the tip of my little penis, and I began to ooze cum onto the shower floor. I watched it pool up on the porcelain, runny and whitish, and moved my head close enough to lick it up. I had never tasted my cum before that day, but on that day I became an addict. My asshole relaxed on the dildo, but instead of stopping I took it a little deeper.

Working it's head and shaft into my stretched asshole became easier, and after 30 minutes of shooting small amounts of cum towards my face I began to ride the dildo in an upright position. I knelt down over it, taking eight of the twelve inches deeply enough to feel it encounter another barrier. I pressed down against it, and felt another popping sensation. The pleasure flared, mixed with a little pain, as I began fucking myself so deeply that I felt the dildo's balls against my asshole.

Cum was flying out of my cock, all over me and the glass doors of the tub/shower. It became hypnotic; I was focused solely on the sensations from within my own body, and the flavor of the occasional bit of cum that landed on my lips or chin. I fucked myself for over an hour, feeling my raw asshole and insides throb with pain. I lifted up off the dildo and watched it flop down onto the floor.

I cleaned off again, washing off the dildo, and stood looking at myself in the mirror. I turned around, spreading my cheeks, and looked at my ruined ass. I had cum literally all over the place, and had fucked myself so long that I was physically exhausted -- except for my cock. The thought of the cum, the sight of the giant dildo on the counter top, and the feeling of a completely stretched out ass got me rock hard again.

I stroked my cock, and the dildo, rubbing it against my big balls. I imagined jerking off another guy and feeling his cum cover my crotch. I quickly came, thick ropes of cum landing on the tile floor in front of me. As soon as I was done with my orgasm I dropped to all fours and began licking it off the floor. I had never felt for dirty, or sexy, than I did at that moment. I wanted more, and for weeks I did nothing but come home from work and fuck my ass with that monster.

So before you decide to try fucking your asshole with a dildo for the first time, just make sure you have plenty of time available to experiment with. Plenty of lube as well.