Fingering My Ass: Using Anal Toys & Butt Plugs

The joys of using toys & fingering my ass!

Fingering my ass and playing with toys was a kinky curiosity. I discovered it when I first went on a kink-exploring spiral! See, I was actually pretty tame once. I’ll say I was tame just once. Because once my curiosity got going, it was game over. I shamelessly started exploring all kinds of different fetishes. But the beginning was so sweetly curious. See, I’m a total masochist sometimes. I crave a little pain, whether from using clothespins, spankings, etc!

I had never played with my ass in the past. The thought of fingering my ass was still new to me. But there I was, being a curious devil and going through online forums. I used to visit a specific site where people would trade all kinds of tasks and punishments. It was an overwhelmingly naughty experience. I think the excitement came from reading about all these different kinks and tasks that people would give each other. It excited me to think about giving control to someone else, it thrilled me to think about playing with myself as they commanded.

And I loved using toys and fingering my ass.

That was when I got my first vibrator. I purchased a little clit vibrator that looked vaguely like lipstick. That little thing brought me so many body-rocking orgasms. And soon after, I kept seeing tasks involving butt play. The first ‘anal’ thing I tried was rather innocent, and a flop. I tried to fit a banana in my ass, per the random person’s request. I had yet to learn a few things… That my ass is VERY tight, and that if you want to fuck any kind of fruit, it better be frozen or it’ll squish instead of go in! So I settled for fingering my ass instead. And that felt so curiously good that I kept exploring.

The ideas continued. Instead of fingers, they wanted to see how many markers I could fit. I had a set of smooth-ended markers that I started fucking my ass with. Then I fit a second, then I fit a third… Oh, that feeling of stretching my tight little ass out was so intoxicatingly good. I would slip one extra marker in at a time, squirming and struggling to keep it in. My legs were shaking. I was trembling from how good it felt, and the intoxication from that mix of pain and pleasure. Just like that, I’d become motivated to buy actual anal toys.

Fingering my ass was fun, but butt plugs were better.

I found the sexiest little butt plug at the sex store, too. It was a dark gunmetal butt plug, with the most vibrant red crystal heart at the flared base. How fucking sexy is that? I took it home immediately, along with a few other toys. When I slipped it into my ass, it was such a different feeling. I had plenty of experience playing with my pussy. But fingering my ass was exciting, and stretching my ass with markers was a challenge. But this metal butt plug had a ‘weight’ to it that was so fulfilling to fuck my ass with. I started pulling it in and out just to feel my little asshole stretch and then squeeze it tight.

All night long, I played with my new toys, putting on a show for myself in the mirror. I started by fingering my ass to get it warmed up for the rest. Then I focused on that little butt plug for a while. After a while of abusing my little asshole by pumping the plug in and out, I was craving something bigger. And that’s where the vibrating dildo came into play. I got a nice vibrating dildo with a suction cup on the bottom. And my first order of business was to set it up on a little chair. I lubed it up liberally and then carefully hovered above it.

My little ass was craving it.

As I lowered down onto the thick head of the toy, I almost regretted my decision… I was so tight, and that toy was so thick! Fingering my ass hadn’t prepared me for the way that thick dildo stretched me out. As I turned on the vibrations, I felt the sensations rock my entire body. It helped my tight ass relax a little, and it felt so good too. I lowered myself down onto it a little more, then I double-checked those ‘tasks’ I was given. Horny guys were so ambitious! They wanted me to bounce up and down on it a hundred times. A hundred! And my sore ass could barely fit that toy already! I cheated my way through that one and saved the ‘hundred pumps’ for another day. But it unlocked a new world for me. When did you first get curious about anal?

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