Chastity and orgasm denial discussion

Chastity has become a bigger part of my wife’s sexual life than almost anything else in our marriage. She is quite shy regarding sex and feels significant pressure when I request something new or different. Over our nearly twenty years together, I’ve experienced both successes and many failures. She is aware of my unusual desires and has appreciated the benefits we’ve enjoyed during these last ten months of chastity play.

I know she misses penetrative intercourse; usually, I can’t hold out long when permitted to release. We own a vibrator which she likes occasionally, not hesitating to request it when desired. However, I struggle to bring her to climax using just the device.

In short, I want to add a strap-on to help meet her needs while I am locked up. It would be incredibly appealing for me to remain caged yet thrust into her—a common fantasy, undoubtedly.

I get one chance at this and I don’t want to overwhelm her (though it likely will). Often, when I try to introduce a toy during intimacy, she cuts me off before finishing my sentence with a simple “No.”

What advice do you have for presenting an item that lies firmly outside her comfort zone? I’d appreciate some ideas.

I lack specific experience here, but perhaps suggest introducing a dildo by hand while you are performing oral sex on her. If she approves of one particular model, you might then try advancing to the next stage. An intermediate option could involve holding the device in your hands but using your body's thrusting motion as if it were attached like a strap-on? Wishing you luck.