Remember that a chastity slave stays locked while getting fucked. If he can’t cum in his cage, then he doesn’t get to cum.
Remember that humiliation is the objective. Do whatever you can to humiliate and emasculate him.
Each position has pros and cons.
Missionary: a classic but requires a lot of endurance on your part. Definitely do it from time to time. it’s going to really make him feel vulnerable being face-to-face on his back with his legs in the air, but ultimately not my favorite.
Cowgirl (cowboy?): this one is particularly humiliating because it makes him climb up on top and do all the work riding your cock in full view. he will never feel more exposed. It also gives you a break and allows free access to his cage. You can easily place a vibrator on it for extra simulation.
Reverse cowgirl: similar to cowgirl, but a different view.
Also provides you a rest from other more engaging positions and allows you to see how eager he is to bounce up and down on your cock. This one can be fun to watch because it really shows how much of a slut he has become. It also gives him access to his cage, and you can let him use the vibrator on himself, making it even sluttier and more humiliating for him as he rides.
Doggy style: the quintessential pegging position. Gives your upper body a break from positions like missionary, but allows you to dominate and really exert control over him. This is the position you go in to show him whose boss. this position puts him in the most vulnerable position so far, putting him totally in your control. It also gives you access to smack his ass and pull his hair like a good little bitch he is. This is your chance to really give it to him. Fuck him hard and fast when you get tired, just stop and just wait… if you have them trained well he’ll start pushing back onto you and fucking himself. if he doesn’t start doing it on his own, smack his ass and tell him to do it. This adds tons of humiliation. I can’t think of anything more humiliating than him bent over throwing his ass back into your cock like an eager cock whore. Just enjoy the view, you won.
Blowjob: an all-time favorite. he should never get away from giving your cock its well deserved blow job. He needs to respect your cock and worship it. That starts with a good solid blow job. Put him down on his knees and make him gag. Hang his head over the bed and fuck his face. Take pictures. use a double sided dildo so that you get pleasure from it as well. It’s so hot to have an orgasm while he’s sucking you off.
These are the basics, but don’t forget the extra things you can do to make it extra humiliating.
Open the window while you fuck him and make him worry that someone might see or hear. Take him to the window and press him up against the glass or take him out on the balcony/patio if you have one and make him ride your cock in plane view.
Restrain him to the bed with bondage equipment. Put nipple clamps and a ball gag. After you’re done fucking him. Detach the dildo from your harness andleave the dildo in his ass. come back later. Give him some time to really think about what just happened.
If he’s gonna get fucked like a bitch, dress him up like one. Make him wear slutty lingerie while you peg him.
Take pictures and videos. You’ll want these for later to keep him in line. If you’ve got pictures like this on your phone, no man is EVER talking back to you.
the cornerstones of male chastity is humiliation.
Anything you can do that would humiliate/emasculate him is likely the right answer. Anything that takes away his masculinity and puts him in the traditional female role is exactly what he wants.
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