Background: The next three stories involve my only long-term on-line subject who I have named Nancy. This subject passed all of the tests I described in story two ("A Few Good Subs"), but before we were able to arrange an in-person session, he was offered a job in a town a great distance away, precluding any in-person meets.
We agreed to continue training via on-line sessions with the stipulation that they might be somewhat infrequent but that he would be required to maintain a high degree of diligence in meeting requests and maintaining a daily submission regimen. After working out some details we agreed to try it out and the relationship continued for over a year.
Nancy is a computer nerd. Brilliant at working with machines of all kinds, but hopeless with humans. He's not terribly self-confident unless he's writing software code, where he feels he's 'among the best.' He's early-thirties, slender, but not really physically fit. Scrawny is the word one might use. He admits to having little experience with women and that he has only had actual intercourse one time.
He told me in high school the good-looking 'cheerleader' types used to taunt him and tease him about being a sissy and he secretly loved their humiliation. He admitted to numerous jack-off sessions imagining various degradations at their hands and that their abuse, and the sexual thrill he took from it, is still essentially the basis of his sexuality.
Apart from female domination, his fetish is lingerie and forced feminization. Through our interactions he has gradually built up a sizeable collection of lingerie which he routinely wears to work under his outer clothes.
It's interesting to note that in the course of our sessions Nancy has never actually seen me. I have sent him pictures that I have told him look similar to me, but never an actual face-shot photo. He has a photo of a vagina that I have told him he may assume is mine which he is sometimes asked to stare at and say devotionals to, but its not mine, just a photo I ripped from the net.
The on-line session
There are a number of different ways we do remote sessions. In this one, I have recorded my commands in a sound file which the subject has downloaded to his iPod. My commands total about thirty minutes with gaps between them. He will respond to my commands during those gaps.
To insure compliance, Nancy will record the session on video and e-mail me the compressed file which I can view at my leisure.
For this session Nancy is kneeling in front of a mirror dressed in sissy attire. His iPod is in a docking station off camera turned up loud enough that my commands can be heard on the video recording. The video is taken from behind him aimed at the mirror such that most of the view is of the reflection of what he is doing.
Session
"Hello Nancy. Please begin by reciting my rules for being a good submissive"
Yes Mistress. The first rule is to listen carefully and obey all instructions to the best of my ability. Inattention to details or laxness in executing instructions will never be tolerated. A good submissive knows that failure will be punished and understands when he has failed.
The second rule is to always be respectful to Mistress and focus all attention on serving her. A submissive who is respectful and focused has the best chance to be rewarded.
The third rule it that a good submissive always knows his place. They only speak when spoken to, do not question or talk back and accept that mistress knows what is best.
The fourth rule is that Mistress and only Mistress controls the submissive's sexual pleasure. My cock belongs to Mistress and she will decide when, if, and how I am allowed to achieve pleasure with it and release if I have earned it. A good submissive should expect violations to be punished.
The fifth rule is absolute honesty at all times. A Mistress – submissive relationship is based upon mutual trust which takes time to earn but can be destroyed quickly. The good submissive understands this rule is to be absolute and is one which will be given the least tolerance if it is broken.
The sixth is a good submissive will at all times wear at least one outward sign of his service and submission. I always wear a pink and red woven bracelet around my ankle as a sign of my service. I never take it off except to shower.
The seventh rule is that a good submissive will think about serving his Mistress even when she is not present. He will think 'What would Mistress have me do?' and "How does this action help me serve my Mistress better?' At least once each day a good submissive will pay his respects to his Mistress without being prompted, even when she is not present.
This morning I kneeled next to my bed, head bowed and silently thanked my mistress for taking the time to teach me how to serve her and for allowing me to serve her and to become a better person.
Thank you Mistress for allowing me to recite these rules. They are a good reminder of what is important and what I must do to serve you well and earn your favor.
"You should know that your performance on your last remote session was satisfactory and has caused me to at least consider the possibility of granting you a release during this session. I hope that will motivate you to be appropriately enthusiastic during this session. Should I grant a release and this session prove slack, there will be consequences. Please think about this."
Yes Mistress. Thank you Mistress.
"If you are carefully following my instructions you should be dressed in a selection of sissy attire and kneeling in front of a mirror looking at yourself and just how submissive and pathetic you look. While I can see what you are wearing, please describe each of your selections and why you have made them"
Yes Mistress. I understand that I am meant to present as a sissy. I have chosen my frilliest pink panties with lace around all openings and lots of frilly ruffles on the bottom. I've also chosen matching pink ankle sox with lace on them and patent black Mary Jane shoes with a three inch heel. I am wearing a pretty baby doll top with flowers and lace at the sleeves. Underneath I am wearing a plain white training bra.
I have chosen these items to show that I am still just a sissy in training and I need your instruction to be a proper sissy. I hope you will find them submissive enough.
"Take a good long look at yourself Nancy. Do you like the person you see there? Does it make you happy to be a sissy for your Mistress?"
Yes Ma'am. I like to be a sissy for you. It makes me happy to serve you.
"Its rather pathetic isn't it? A grown man dressed up in little girl clothes? Getting hard from dressing up like a little sissy boy? Is this what you like? Do you like to look all sweet and girly?"
Yes Ma'am. I like to look sweet and girly. It makes me feel good to dress this way. It makes me feel submissive to dress like this for you and be all sweet and girly. I'm not worthy to be a real girl. I can only be a sissy boy. Thank you for letting me dress like this for you. Thank you for training me to be your sissy.
"What would your boss say if he saw you like this? What about that girl that sits near you? The one you think is pretty. Do you think she would like you as a sissy boy? Would she make you her pet? Look at yourself in the mirror and think about her laughing at you. Laughing at her sissy co-worker. Just sit and look at yourself all dressed in your frillies and think about that."
There is a 3 minute pause while Nancy looks at himself
"It made you hard didn't it. Being humiliated in front of a pretty, intelligent, dominant woman makes you hard doesn't it?"
Yes Ma'am. I admit. It makes me hard to think about being humiliated like that. Sherri is very pretty, and smart. She is like you. I get hard thinking about submitting to her just like when I submit to you. I just want to serve you so much and I feel so small and submissive dressed like this.
I know my place is at the service of an intelligent dominant woman but I know I'm not worthy as a man. I can only hope I will be worthy as a sissy.
"What would you do for her if she was there? How would you submit to your co-worker?"
