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I know he wants to cum after aching in his cage for so long. But how much does he really want to cum? Make it clear to him that if he cums, whether from a handjob or sex, regardless of full or ruined orgasm, he will need to swallow whatever amount of cum he ejects. Doesn’t matter if he has post-nut clarity or not, that is the price to pay for cumming. Then see if he still wants to cum.
Setting up a recurrent submissive act like a panties night is great for emasculating your sub. Many guys into chastity are into this type of thing but scared to ask for it, so you’re basically doing him a favor by proposing this. Once a week (you can change the day, we used Friday) you set the expectation that he will wear women’s panties over his cage. On the right guy this will reliably turn him on every week and have him begging for some attention. Of course it’s always fun to just make him show me he is obeying. But the most fun I have with this is when I forget about it until I randomly see his underwear. The teasing I give is so much more genuine when I realize he was being submissive to me without me even realizing it.
Mistress straps the dildo gag on Pet and ride for as many orgasms as she feel appropriate before vibrating her clit and Pets cage until her cums on her beautiful pussy. Mistress then sits on Pets face for a cleanup and another orgasm.
Everyone should have a go at experiencing a Micro-cage. At intervals throughout your lock up period, your cage should be "shrunk." Whilst long term lock ups in micro cages can be a struggle and potentially dangerous, you should experience true snugness. If your submissibe is begging for a release, this is perfect for teasing and punishing. Act as if they are getting a release. Lay them down, blindfold them, and restrain them. Release the cage and do a bit of fondling, maybe a kiss. Then leave them there whilst their member becomes able to fit in a micro cage as you go to "change into something more appropriate." Come back and lock them into the micro cage and let them know this is a result of uncontractual begging. Tell them a fixed time for this punishment (4 hours for example) this should increase on repeated infractions.
Keyholder agrees to tease partner daily, preferably multiple times a day. She also agrees to edge partner weekly (during the weekly hygiene release) preferably multiple times. Orgasms are at the sole discretion of the Keyholder and there are no restrictions on when or if the Keyholder allows.
Switch couples sometimes have trouble with chastity play because after a while the key holder starts wanting to be dominated. This role play is a perfect for when you don’t want to drop the pretense of control over your submissive, but you do want to submit yourself: just put on a hood, chain yourself to the bed and give your submissive orders to fuck the gift “hooded slave girl” however you want to be fucked. Obviously everyone will know what is going on, but the role play is fun! The orders attached here lean into doing a bit of interrogation as well to get the keys out of you, but you can take it in whatever direction you want! And then at the end you take the hood off when he is in the shower and meet back up with him to ask him how it went. Maybe say something like “I examined the slave girl and you could have been rougher. I guess you are just a bit of pussy at heart” to tease him.😂
After penetrative sex, instruct your submissive to clean you with a warm cloth or their mouth, depending on your comfort. Have them kneel and thank you for using them, then guide them to fetch water, brush your hair, or massage your shoulders while you relax. This frames the end of sex not as collapse but as extended ritual, reinforcing power dynamics even after orgasm.
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