A milking which doesn't feel like anything at all. Complete frustration.

I am chaste although I am not locked all the time but I know that I am not allowed to cheat or cum. Recently we started working on milking but I think the ruined orgasms were more fun as we almost got it perfect. Milking these days has left me so incredibly frustrated and I will do what Mistress says just with the hope of a real O (Not going to happen), or a ruined O, but the milking relieves the stress even when it drips out slowly but there is no satisfaction in it. I desperately miss having a real orgasm but I have also found that I am 100% more obedient and will submit to almost anything. It is almost perfect and it has helped Mistress increase my feminization and embracing the fact that I am an owned sissy slut. Now if we could solve the turtle problem I would be locked 24 X 7 and I know Mistress would keep it that way forever, the way it should be. Someday we will get there and She will smile and I will probably cry. LOL

Ten months ago i took a deep breath and asked Mistress Ayn to be my Keyholder. Besides actually serving Her (and the Ladies at the FemDom Mansion), this was the best decision as a sub i ever made. i can count SIX real orgasms for 2019 so far, with other ruined orgasms as ordered by Mistress Ayn. The Holy Trainer is a wonderful device, passing through airport security with no problem. i am only permitted out of the cage upon Mistress's orders and to orgasm upon command. i would not have it any other way. i am frustrated most of the time - and, yes, a milking (only had one and it was unintended during a gang bang birthday present) is not satisfying at all. My frustration reminds me that i am Mistress Ayn's slaveboy and this pleases Her. And, Mistress Ayn is true to Her advice - i am allowed an orgasm rarely but often enough so that i still remember what i am giving up for my Mistress. Chastity has been a true blessing for me, as administered by my Keyholder, Mistress Ayn.

I find Chastity to be addictive and a kink that can push your limits. Submitting to a key holder is a rush. I'm thrilled to see that Mistress Ayn still enjoys Chastity training. I know She would be an amazing Key Holder.

I've wondered who's been holding your key since Mistress Meredith retired. I miss having Her send you to Me. We were quite the duo, She and I.

If someone is a good boy, he might get one on Thursday . . . but it might be ruined. Who knows.

+1

Nope.. not jealous of you...

Well..

Maybe a little

I'd say it was a cross between a ruined orgasm and, a serious mind game.