Dear Annie,
Congratulations on accepting my offer of employment. I trust you and I will each enjoy your tenure equally. I thought it might be helpful to lay out my expectations for your first week of work. I’m sending this on Friday afternoon so you have the weekend to think, prepare, and ask any questions you may have before Monday morning rolls around when, I hope, we will be off to the races.
Daily Responsibilities Overview
As you know, you have a number of daily responsibilities as well as periodic opportunities to serve and requirements that may materialize.
First Monday Dressing Instructions
The first, most obvious, most important, will be the start of your day on Monday. I’d like for you to dress for me. Because you won’t have been working for me previous, I will not select your clothes specifically from among the choices you give me. Although, beginning Monday evening, I will ask that each night at 8 o’clock you send me photos of three options tops and bottoms as well as any additional hosiery or items that might be required. I will make my selection no later than 11 p.m. each night and I will ask that you honor it the following day.
But on this, your first Monday, dress yourself, please. Dress simply in jeans and a t-shirt with lacy, light-colored bra and panties that match, if possible. As you dress, I would like to see. This can either be in photos taken as you add each item of clothing of your bra on you, of your jeans on you, and of your t-shirt on you, or it can be in a single video. Regardless, I want to see privileged views of your thighs and cunt and of your cleavage and your ass as you dress.
Once dressed, you will have one more element of this task to perform. And this will necessarily be on video. Edge for me. Use your fingers, use your vibrator, I don’t care. But bring yourself tantalizingly close to orgasm and show me. If you’re comfortable with your face in the video, great. If not, no worries. The goal here is to keep my eyes focused on your pussy as you bring yourself pleasure and deny yourself satisfaction, at my request.
Calendar and Scheduling Requirements
Once you’ve completed this task, I have only a couple of more requirements of you on this day.
One. Share your Google Calendar with me. I need not see the details of your work appointments, your free and busy status. And I would like to see your personal calendar in its entirety.
Two. Offer me windows of time across the week as I might see fit. These windows might be as short as 30 seconds or as long as several hours. For any such window, send me a Google Calendar invite in the notes. Any constraints on your availability to me, whether those constraints are geographic or social or logistical. For example, if you tell me that you’ll be in a coffee shop If you tell me that you can’t be in public, that constrains what I might ask of you. If you tell me that you must be at your desk, that constrains me. If you tell me that you can be anywhere that you can get to within the bounds of the time offered, that offers me opportunity.
I would like for you to ensure that I have at least two windows of time adding up to at least one hour on every day of the week. This could be a 60-second window and a 59-minute window. It could be three 20-minute windows. It could be a 20-minute window and a 40-minute window. It’s up to you. All I care about is that there be at least two, and that they add up to at least an hour. These times can be at any point in the day, and they should be scheduled without reference to my schedule.
In addition, while I don’t commit to making use of this, I ask that you offer me at least one window of four or more hours. And that this window, if at all possible, overlap with at least three hours of my availability. And if not three, at least two.
In the future, I’ll ask that you do this calendaring exercise on Sundays or over the weekend for the coming week, but no later than 8 p.m. on Sunday. And you would be welcome to start your week early in this way if you’d like. But I recognize that your employment with me does not technically begin until Monday morning. So no pressure.
Voice Memo Tasks
I have one other task with which I would like to seed your week. And that is the following. I need to learn about your wardrobe and your masturbation. I’d like to do this in two ways, among others. First, please record for me a voice memo on each topic. With regard to your wardrobe, describe it to me in detail. And with respect to your masturbation, describe that to me in detail.
And a general rule for me, when you are recording audio for me, unless circumstances prohibit it, in which case you should tell me so, I would like for your fingers to be touching your pussy while you’re speaking. And I’d like for you to tell me that at the beginning of each recording. And at the end. And I would like for you not to achieve orgasm unless specifically instructed by me to do so. Feel free to come painfully close, however.
These recordings I’d like from you at some point in the course of the day on Monday.
Clothing Directory Task
With respect to your clothes, there is an ongoing task. And that is for you to begin to compile for me a comprehensive directory of every item of your clothing. Initially, it’s fine if this is photographic or video evidence of your clothes in their closeted or cabineted state. But over time, this directory will grow to feature photos and videos of you in every item of clothing you wear. This will facilitate both my getting to know you and the selections I may make with respect to your dressing.
Closing
I hope you have a good weekend and that you are as excited about your start as I am.
Warmly and with my hard cock in my hand.