Conspire with a another woman in another city to tease him with you.
When he travels to that city, make sure he's in chastity with a plastic lock. Then have him meet with that what woman (maybe a girlfriend of yours, a friend of his) and either get her to extract his chastity secret or to tip-toe around some sort of secret she's discovered about him. Then get her to give him a sealed envelope to be given exclusively to you.... which should read: “I’ve figured out that he’s a sissy, confronted him, and he says your keep him in Chastity. I think it’s cute that you do. He told me you have numbered locks for him, so if you want me to check up on him when he’s around, I’m happy to do so, just text me with the number…..boy, he’ll be very surprised....although I always knew he was a bit of a sissy."
You can share the note with him later, so he suffers some very sweet humiliation, then let him know that you’ll be taking her up on the offer!
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I have a girlfriend that my cuckold sissy hubby and I visit with two times a year. She knew prior to our visit that hubby was a cuckold sissy. In speaking with her I mentioned I would send her his key, by mail, and that she should wear it upon our visit. It worked like a charm as I left the condo one morning, so they could eat breakfast alone. In chatting he came out and asked about the key she was wearing. She teased him with other answers before reveiling that the key belong to his chastity. She showed him the ingraving on the key which bears his sissy name. The look on his face was priceless according to my GF. I returned later with a lingerie gift for my cuckold sissy to wear for my girlfriend and I. Later that day my girlfriend and I allowed my cuckold sissy to watch, and then join in, in a little bisexual love making.
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