My First Time by Casey

My first time by Casey Wildmist

I've been learning a lot over the past couple of weeks at the wonderful instruction of Miss Crissy. It's been an eye opening experience in so many ways and it's hard to put into words all the feelings I've been having. For now I'm going to stick with one experience in particular that blew my mind and showed me what it is I'd been missing in my life.
Miss Crissy gave me a bdsm check list to fill out, which I did over the course of a few days, and one thing listed on there that made me tingle with curiosity was anal play. Of course I'd seen videos and read plenty about it, but I'd never done anything involving the "back door".
We were talking one evening when Miss Crissy gave me the instruction that when I showered next I was to lather up my fingers and explore my ass, and if it turned me on I was allowed to edge but not cum. I nervously followed her instructions and found that stroking my anus and penetrating it slowly with one finger was indeed a turn on. After reporting this to  her, Miss Crissy suggested I pick up some lube and gloves, which I did a few days later.
That evening she ordered me to get my lube and gloves which set me to squirming with anticipation. After following her directions to lube my ass up well, I slowly sild my index finger into my anus, unable to restrain the moan of pleasure. Hearing her laughter and enjoyment of my reaction just made me want more and I slowly began to fuck my ass with that single finger, kneeling on the floor and leaning against my seat. I tried to focus on pleasing Miss Crissy and making sure I was showing proper gratitude but the pleasure of the moment kept pulling my focus away. After several slow, deep breaths and slowing my strokes I was able to focus better on her voice. Narrowing my concentration to the sensations rushing through my body and her commands I kept sliding my well lubed finger in and out of my ass, surprised at the way it was turning me on. When I added the clothespins on my nipples that drove me even closer to the edge and had me shaking with the need to cum. Then I heard the wonderful words, the order to fuck my ass until I came. I pumped my finger faster and faster into my body, the sensations building quickly until I was overwhelmed with an incredible orgasm. After coming down from that high I couldn't thank Miss Crissy enough for opening my eyes to this new and incredible pleasure.
And that is my confession of my first time with anal play.