My first evening messaging with Mistress Penny. ([u/prettypennyp](https://www.reddit.com/u/prettypennyp/)) I let her know I was home and awaiting and commands she might give me. Mistress Penny sends her first message, “I’d like it if you played with your nipples until you’re drooling in your cage,” she said. I responded “As you wish, my mistress. Will master help me in any way? Please” Mistress Penny wants to know, “Tell me how you want my help.”
I begin following the command given, Oh, Mistress Penny I wish that you were in my room right now with the red lights on. You tell me to bend over, shaming me you say to only look at your feet, because I was not worthy to look at you yet. You pull out a leather crop tracing it along my back. As you reach my ass you give it a little quick smack. The is an escape from the tips of my lips as you do this, a little chirp of pleasure, surprisingly enjoying the slap you just gave me. It is a vocal giggle of aroused glee. At the same time I begin feeling a twitch between my legs.
As I finish typing this I look down to my cage and raise 1 finger to it pressing the tip of my finger against the tip of my caged cock. Already a little string coming from the opening in the cage from my cock.
Mistress Penny approves with “Mm, what a lovely little imagination you have! Such lush visuals.” “Well I want to make sure you are able to visualize what I am doing as I type it to you.” It feels so good. My nipples played with as I typed and played. Drool in cage. Check. As you commanded, my mistress.
A brief break before the next message comes from my Mistress. “You mentioned you’ve been experimenting with anal. Tell me a little about what you like.”
I like something small to start. Some beads or something with a small point. “What would mistress like me to use?” I ask as I send a picture of a little blue gem anal plug, and some pink anal beads. “I would like you to use the beads,” she responds. “Is that what mistress wants me to use?” I inquire. “Yes, I’d like to know how many you can take.” “As you wish, my mistress.”
I like to start with just a light pressure pushing against the opening of my anus, so I take the beads in my hand and proceed to bend over the bed. I take just the first bead and slowly push it up against my asshole. Just a light pressure pushing against the entrance. Slowly I begin to push it, ever so slow and cautious but deeper. As I push against my opening, bending over, across the corner of my bed, I feel the pressure as it begins to slide deeper, deeper inside. After I feel the pressure of the first set of two beads pushing inside, one tiny bump followed right behind by the other. I check thinking only the first two slid in, but I was wrong, it was the first four. Eager arousal begins to build in my body. I feel the next bigger set, they are right behind the first 2 sets, bigger but still wanting in. I push more and suddenly I feel the pop of the next two little beads.
“Very, very good.” Mistress Penny coaxes.
As the fourth pair of beads reaches my ass, even though it is another step bigger, my hole opens right up, accepting them in, surprising me that my ass is hungry for more. As I do this, I notice that my nipples have been brushing against the sheets all the whole time. I take just a few moments to enjoy the brushing and arousal on my nipples focusing on the ecstasy it is causing as it sends shocks straight to my groin. I send a short video to Mistress Penny of my nipples brushing against the sheets.
Slowly I start to fuck the beads that are caressing my anus. Sending a shiver up my core. I send a voice clip, “MMmm it feels so good” I moan out. Mmm mistress. It feels so nice. I think this is all I can take at this time. Just the first four, small double sets. “As you commanded, my mistress.”
Source: reddit.com/r/eroticliterature/comments/iid16a/first_encounter_with_mistress