Decent into Debauchery Pt. 01

I think I did a good job tonight treating her like my girlfriend. I wore stockings for her and cooked her dinner and we had an amazing time together. You have been right about everything else, I hope you are right about me getting on my knees for her; just the thought of it has my hands gravitating away from the keyboard.

I am wearing the stockings as I writ this, although it was not at your request. I already had them on for our dinner tonight. But I am wondering what you meant when you said, 'if you were right about me?' What else do you know about me that I don't?

B

I hit send and re-focused my attention on Chastity. She seemed to be having a hard time falling asleep, turning over and over. I enjoyed watching her, even her restlessness was a dance of beauty for me to admire. She was teasing me without even realizing it. I pinched one nipple and slipped two fingers inside my pussy and started a slow deep rhythm, just watching her fight for sleep and listening to my own breath.

I felt my orgasm growing in my abdomen but I needed it to come slowly and hit hard so I removed my fingers and ran circles around my clit with my wet digits. My hips gyrated as I imagined lying in that bed next to her, touching her, pleasing her, being used by her; I wanted to be her object of pleasure. My breathing was getting deep and ragged when I noticed her hand moving under the blanket. I froze. Was she doing what I thought she was doing? Her hand was on her breasts, pulling at her nipples slowly while she seemed to look straight up at me. It seemed as if she was rounding the first turn on her pleasure coaster. I began to mimic her movements, joining in her quest for relief. My eyes did not avert from her as I learned how she enjoyed playing with herself, she started with heavy breast play before she even attempted to touch her pussy. She tweaked her nipples, twisted them, even licked them and bit them. She began to slowly tease her hand down her body while still pulling on her nipple and I leaned in closer to ensure I did not miss a single detail.

DING!

I almost jumped out of my skin; I was so focused on Chastity and her exploring hand. I clicked the message and let it open while I continued to stare at my secret lover giving me instructions on how to please her. I glanced over for a second to see the message when big, bold letters caught my eye.

B,

REMOVE YOUR HAND FROM YOUR PUSSY! Tonight is about enjoying the act of watching, you will not touch yourself you will only watch. You have an opportunity to truly dive deep into the world of voyeurism; do not dilute it with nonstop orgasms.

I have no issues with you being crass; it is honest and therefore follows the rules. I am glad the two of you had such an enjoyable time. You must continue to do things like this at least once a week. It can be your sexy date night. As long as you have the stockings on when you reply to me I do not care what encouraged you to put them on. I care about rules being followed and getting to know my curious B.

What do I know about you, I know that you immediately stopped touching yourself even though you hate it. I know you get wetter every time you get a message from me; I know your clit swells with the thought of doing as I tell you. What I know about you is what you are soon going to realize, you are submissive. Take some time and look it up and tell me if I am wrong. If I am right the next message you send needs to include a picture of your stocking clad legs. Good night B.

XX Mistress T

My hands were on the keyboard, my pussy was soaked, my dream girl was touching her pussy for me to see and I couldn't get myself off. I was conflicted. Was I a submissive? What does that even mean? I mean damn, I just got used to this voyeur thing and now I'm something else as well?

I watched while her hand moved under the blanket and her mouth hung open while she worked on maintaining a rhythm of moaning and breathing. I felt my clit burn with the need for attention, only to be mocked by the first line of Mistress T's last email. I watched her intently, wishing I could join in her pleasure physically. Mentally I was with her, but of course it was a tortured pleasure not being able to touch her, or myself.

Her orgasm was one of the most beautiful things I had ever seen. The way she writhed, the sound of her moans, the way her back arched and she pushed her nipples into the air...it was art in motion. She fell asleep soon after and with no other choice, I got ready to follow suit—completely frustrated and soaked.

I lay in bed in the dark and I knew that from this point forward, my life would not be anything close to what it was a week ago. I had a secret girlfriend and a Mistress; my life was getting better by the day. As I smiled and began to drift off to sleep, I decided that tomorrow I would take some pictures for my Mistress and try once again to get into my best friends panties.

DING!