Interrogation/Confessions While Masturbating

Masturbate him while administering a strict interrogation and extracting confessions. Make sure his hands and legs are completely tied down so he cannot move. 

Pleasure him with nice lubricated and lovely strokes when he answers your questions and give your information.  

When he is more resistant to answering your questions then stop pleasuring him immediately until he resumes his cooperation.  Apply the chastity device again prior to untying him.

 

Release, But Don't Touch!

Let him out to masturbate, but make it impossible or extremely difficult to for him to touch himself directly.  Give him rubber kitchen gloves or lock oven mitts on to him that he must use to masturbate while you stand over him and observe him enforcing a strict time limit.  He may have to rub up against something.   Take lot’s of pictures of him trying to masturbate while it’s impossibly hard!

 

Un-Erotic Release and Milking

Release him from the Chastity Device daily to be masturbated by you in a very dry and unexciting way, using a thick rubber glove…. Then apply the Chastity Device immediately within 5 minutes afterwards with ice if necessary.

Chastity Removal/Compliance Insurance

Lock something on him (Ankle weight, butt plug, collar, etc) every time he's let out of Chastity, in order to ensure he puts the Chastity device back on afterwards. 

This is so important, because once you release him and after he orgasms, he will not have the sexual drive for obeying you and putting the chastity device back on himself.  He will need the added motivation of not being fully released ever, and only finding comfort again once he re-installs his chastity device.

Practice Orgasm Control

Practicing ruined orgasms, orgasm on demand, and orgasm control.  He should be lying face up on the bed naked with his Chastity Device off and his hands tucked under his buttocks or tied down so they cannot move.   

You should be dressed in very sexy lingerie is sitting beside him masturbating him with one hand. You can even make him think you will let him penetrate you, but stop him at the last minute.   The point is to tease him, making him think he’ll be able to cum, but to stop him from doing so and keeping him just on the edge.

Be ready to grab a handful of ice-cubes from a bowl full of ice to slow things down and ruin his orgasm just when he's on the edge.