So the other night was the last time I was allowed to cum. Initially Miss H and I decided that before starting on my current period of chastity we would have two last days to had sex and generally chill out with each other. Well, one thing led to another and things got heated, in a good way, and before you know it Mistress had changed her mind about when exactly my chastity should start. Right in the middle of sex she kind of stops, looks at me, and tells me to pull out of her. She announced that my chastity was starting early and I wouldn't be cumming that night after all.
I don't know if this was planned from the beginning or she stopped because I wasn't sexually satisfying her or she honestly did just change her mind spur of the moment, but it was a shock what ever the reason. So of course I started whining like a little bratty bitch to please allow me to penetrate her a few more times at least but she seemed steadfast in denying me.
At this point I got desperate so I tried to bargain with her, offering up various methods of self humiliation in exchange for being allowed the privileged to cum. I don't even remember what I initially offered to do but it wasn't long before I was saying anything I could think of that might provide just enough embarrassment to tempt her into letting me cum. I told her I would cum on her feet and lick it off, that I would lay upside down and jerk off onto my on face, anything to just let me cum. Mistress toyed with me for a while until I finally was so desperate I was literally begging and pleading to allow her to let me wear a condom to have sex with her and promising that I would swallow the entire contents of it after I had cum.
It took about two and a half seconds after she said yes that I was suddenly regretting my choice. I get so worked up when I'm horny and haven't cum in a while that I tend to forget just how quickly and deeply I fall out of "subspace" immediately after cumming. It's then that that once super erotic thought of swallowing down a huge load of my own cum suddenly becomes crushingly shameful and humiliating, and not in the way I enjoy. I quickly began trying to back out of the deal but Miss H would have no part of it. She told me I had one minute left to cum so not wanting to waste the opportunity to orgasm, I did. I thought that Mistress might see the look of disgust and shame on my face and let me escape without performing what I had so foolishly offered. We lay in bed cuddling and I honestly believed I wouldn't have to go through with it.
She just smiled and said "Drink it. Now."
I didn't have much of a choice so I did as she ordered, wincing as I held the condom up above my mouth, waiting for my warm sperm to splash down between my lips. I took it like a shot, one big gulp and done with. Mistress seemed happy enough by what I had done and we soon slipped off to sleep together, she seemingly amused and content while I laid there in the darkness contemplating just how much of a sissy bitch I was really becoming.