Sisterhood of Sin -- 12 --The Caged Cock - Sex Stories

Sisterhood of Sin -- 12 --The Caged Cock

Dan's night for the Earn an Orgasm game arrives almost too soon. I've had a busy week; an interview with his probable future mistress, a short business trip where I also met his former mistress, and a session with my shrink where I discussed my experience with chastity. She agrees with me that the orgasm denial subculture is not healthy but she's intrigued about how short chastity sessions and the game can break down barriers. I showed her my chastity belt. The custom creation that I bought from Serena is probably too expensive and not really necessary for short sessions, but she liked how the custom fit dome that isolates my clitoris was more effective than the off-the-shelf models. Serena liked the idea, too, and she's experimenting with ways to make it impossible to get anything in to tickle my nubbin. I arrive in the bedroom at the appointed time, wearing a rented Naughty Nun costume. I have my hands stuffed into the opposite sleeves in the classic penguin pose. I sent Dan there with plenty of time to prepare while I donned the nun costume in our guest bedroom, but he's not ready for me. He's still fully clothed and there's no telltale bulge under his clothes from the cock cage. He looks suitably sheepish when he sees my displeasure. "Somebody is being a naughty boy." "I tried, Cathy. It won't fit." I smack him on the thigh with the wooden ruler I've been hiding up my sleeve, "It's Sister Cate. And it's too late to tell me that now, Danny. We'll either make it fit or ...

... you'll take the punishment I decide." "What's the punishment?" I smack his thigh again, hard enough to draw an "Ow!" from him. "Would you care to rephrase that question with a little more respect?" "I'm sorry, Sister Cate. Please, may I know the punishment?" I have to think fast. This will work better if I give him two options. I go to my bag of tricks and pull out a fairly large butt plug, one that I've never had the courage to attempt. "Yes, Danny, if you can't get the challenge device fitted, you will receive twenty bare-handed bare-assed swats while this is in your ass. You will then wear it through your next two orgasms." His eyes widen as he takes in the size of the plug. "On the other hand, if you can get the device fitted and sealed, the punishment for failing to make it three hours will be fifteen swats and you will wear the butt plug that my sister left with you when you took her anal virginity. You do still have that, don't you?" I had expected that small butt plug to show up some day, and when it never did, I wondered whether he threw it away, but I hoped he had saved it and maybe even experimented with it. This provided the opportunity for him to present it. "Um, yes, Sister Cate, I was hoping to give it back to um, your sister some day." "Get it now." I would give almost anything to know where he hid it, but I don't get that pleasure. He leaves the room to retrieve it. I could follow him, but I'm too afraid of pushing him too hard. He could just refuse to play. I ...