N and I have had weekly check-ins since… March(?), I believe. At these check-ins, we go through the (ever-mounting) list of tasks N assigns me to complete—photoshoots, orgasms, etc. If you can think of it, N has probably asked me to do it, and I have probably done it.
For the check-in, N will usually tell me what to wear to our Zoom call. Sometimes it is more professional clothing, other times it might be lingerie. Today, I met with N toward the tail end of my work day. This morning, N picked an item of my clothing from 3 options, as he does with some form of my clothing each day. Today, N chose black leggings for my bottoms. I wore those and a dark purple blouse with gold buttons to our Zoom meeting.
Characteristically, N immediately asked (told) me to start rubbing my clit over my leggings and to undo the top button on my blouse… then a second… and a third. Eventually, N asked me to take off my bra and expose one of my breasts so that I could play with my nipple while I continued to rub my clit, and he stroked his cock and we talked.
Unbeknownst to N, I have been on edge all day. I was looking forward to our Zoom, because (most times) N will facilitate an orgasm (or four) for me to have while we meet. I love coming for N. I love coming for N during our check-ins.
When I come, or when I’m close to coming, my eyes tend to roll in the back of my head. I told N on our call today that it was involuntary and he said, “I don’t think you understand what the word involuntary means!” (I disagree. It’s involuntary).
N told me to make myself come. I asked him if I still could only touch myself over my leggings, and he permitted me to, “Do whatever the fuck you have to. Just come, woman!” So, I slipped my hands inside my leggings, under my panties, and dipped my fingers down into my warm and wet cunt, and began to rub my clit harder and faster. Then, N said “But don’t fucking let your eyes roll back. Look at me the whole time.” I paused for a second to take in the new instructions, realizing this would be nearly impossible. I voiced my concern, and my doubts of the fairness of the ask, and N directed me just to keep going and to keep my eyes on him.
So I tried! I really did! But it’s involuntary, N! Of course, as I got closer, my eyes instinctively rolled back and N raised his voice slightly and said, “Nope! Stop. Stop right now.” I laughed, because I was really close, and groaned. I, again, protested and complained about the impossibility of this task, and then N told me to try again. I slipped my hand back into my, now very wet panties, and tried again to make myself come while focusing on N’s face on my laptop’s screen. N remarked that, “The harder this is for you, the hotter this is for me.”
I was a soldier this time! I was starting to get so close, I got distracted by the hotness of my struggle, and how badly I wanted to come, and my eyes rolled back in enjoyment. Before I even realized what I had done, N again, loudly, told me to stop. This time, feeling rather desperate, I laid my head on the table in front of me and groaned. Complaining and protesting. N told me I could try once more, but if I failed again we were done. Determined, trying so hard to focus and control myself, I once again slipped my hand into my, now-soaked, panties into the hotness of my cunt and began to rub my clit as I looked at N. This time, my eyes didn’t falter. N gave me words of encouragement about how Good of a Girl I was and directions to “Just look at me and fucking come.” I quickly became closer and closer and finally started to orgasm. My eyes shut and my head craned back as I enjoyed my rather highly anticipated orgasm. Then, I heard N protest that I had rolled my eyes back, right as I came! But by that point, it was too late. (I disagree, I made myself come while staring at him the whole time but my eyes just shut right as I was coming!)
Then, N asked (told) me to stand up, take off my blouse and leggings, and make myself come while standing up. My camera only allowed N to see my breasts, stomach, cunt, and thighs, so he said I was free to let my eyes roll back, I just had to make myself come before our timer on Zoom ran out. I had just under two and half minutes. I made myself come, rather quickly, still enjoying the residual sensations from my last orgasm, and then N and I said goodbye.
