Tonight’s degradation fun. (Patreon)

Mistress and I have decided that any time I want to masturbate, I have to tell her a half hour before I do, and then I have to do it in front of one of my cameras. That way, if she wants to say no, she can.

Today though, we discussed expanding on this a bit. We decided that she should get as many orgasms as she wants, and I should have to beg, bargain and pay for every one I get. To that end, she has agreed that whenever I want to jack off, she’ll attach some price to it (provided she sees my message and gets back to me within a half hour). For instance, I’m allowed to message her and say “Mistress, I’d like to masturbate.” And she is then free to say. “Ok, you can masturbate, but then you have to punch yourself in the balls” Or whatever “price” she wants to attach to it, so long as it’s within a half hour of my request. She’s also allowed to simply say “no” if she doesn’t want me to jack off, or if she doesn’t feel like thinking up a price.

Well, it’s been a few days since I came, and I asked her about an hour ago if I could jack off. First, she said that I can if I dump the cum from my condom into a shot glass and drink that. I said OK to the price quickly, as I’ve done this several times for her, and though I HATE it, that won’t happen to horny me, it’ll be post orgasm me, and fuck that bitch right? So, then she messaged me back and said that I have to fill a full shot glass, which meant I’d have to augment my real cum with a bottle of fake cum I bought and mix it together. The end result is really hard to swallow (pun intended), but still I’m so God damn horny I immediately agreed.

Then she came back to me with the added cost that I’d also have to dress up in my full sissy attire tonight after I cum, and again I agreed. Not only was this not discouraging me, but the worse she makes it for post orgasm me, the hornier it makes sissy cunt me (incidentally, that's who I am right now). And after that she said I had to wear a sissy outfit all day tomorrow too.

Finally at this point, I started to wonder what was up. She isn’t usually like that, piling on more and more. That kind of crazy talk is usually my purview, so I asked her if she was just role playing, or if she actually was not wanting me to jack off tonight. I put my words in (parentheses like this) to indicate that the question wasn’t role playing and I wanted an honest/real answer. As I had begun to suspect, she actually didn’t want me to cum tonight, but for whatever reason didn’t want to just tell me “No”. I don’t pretend to have a full understanding of her mind. Well, in addition to the best sissy play I’ve ever had lately, I’m starting to feel very in sub-space with her, and the idea of suffering to please her made me feel really good.

I had a suggestion. “Mistress, in order to show my devotion to you, may I please not be allowed to cum tonight, but may I still pay all of those prices anyway as if I had cum?” Well, this was the right thing to say. She immediately got much more into it and started talking sexy. We started fantasizing, and upping the ante, and pretty soon my orders for tonight had evolved into what they are.

So, she is going out on a date, and I am staying home dressed in sissy clothes. A half hour ago I was required to fill a shot glass with fake jizz, and take a “shot” on my office camera for her amusement right at 6pm, not knowing if she was even watching or not, but knowing that I didn’t have any choice, because if she was watching, and I didn’t do it, she’d be giving me a punishment, that could even be her outing me to someone I know.

And speaking of being in front of my camera at a certain time, here’s what I’m required to do for the rest of the night. (I already did it once, at 6pm and it was tough.) Every hour, on the hour I have to be in front of one of my cameras and take out my sissy clit. I have to stroke it till it gets hard, then keep stroking it for 10 full minutes on camera without coming. Then after cleaning off and eating any pre-cum, I have to tuck my little prick back into my panties and go about my business until the next hour.

If she catches me coming tonight, she’s going to out me to someone. If I simply fail to complete my hourly assignment, she’s going to do some other punishment to me that I don’t yet know. I’m so deliriously horny I can’t stand it, but it’s also the best. I hope to be caught in this awful and wonderful trap for the rest of my life!

P.S. It's now 7:21, and I just had my second round of tease and denial. The original deal was that I make my clit hard, then stroke it for 10 minutes once it was hard. it was taking me a few minutes to get it hard, and she was getting a little impatient (I think because she was waiting for her date to show up, and knew she's had to stop watching any second.) When she mentioned how long it was taking me, I suggested that there be a time limit at the top of the hour for me to get fully hard. If I fail to get hard in that time, it counts as disobedience, and there will be consequences. She asked me how long I thought I'd need to get hard, and I said I could probably do it in 1 to 2 minutes. I was hoping she'd be mean and say 1 minute. As I watched the tree dots ... while she typed, I waited in anticipation, and suddenly "30 seconds to get hard" popped up on my screen! OH MY FUCKING GOD! This woman will be the death of me, and I LOVE IT! As it's only 7:30, and I have several more times of teasing myself to get through tonight, it's quite likely I'll be adding more to this story.