The whole interrogation thing can be so very hot, and this is one of the very best questions to ask, ‘So, have you been a bad boy and cum without permission?’
Make sure they are right near the edge when you ask. If they go quiet it means they have, but don’t push it, not yet, now you can have some fun. If you’re planning on doing this it’s even hotter with them tied up.
Don’t push for the answer , even if they start ‘umming’ or about to confess, now you know, make it worse.
‘Because you know you’re not allowed to, don’t you. It’s me who makes you cum, you wouldn’t be that selfish, would you darling?
‘Because if you have, I’d be cross, I’d have to punish this little dick, you know that right?
Keep on stroking the whole time, then you push again for an answer.
‘So, did you, did you cum without my permission, without me? How many times?
If you are into it, make him describe it too. Keep wanking him the whole time, it’s such a mind fuck.
Then maybe tie him up if you like that, so he’s got no control. Depending what you fancy you could rub menthol into his cock and balls (or even ass for serious pain) as the start of a punishment. It’s a lot of fun to claim you were going to let them cum but now of course you aren’t (even if you weren’t). Claim you were going to let them do other things they crave, blowjob, pussy sex, anal sex even, but now ‘they’ve ruined it’
You could smack their cock, or flog it even. But the most fun is forcing it back into the cage while you tell them how long it will be ‘at least’ until they are allowed out. If you’re into spanking etc you could do that, whatever you fancy.
Then make it clear if they aren’t cumming at least you should and make them go down on you with their cock painfully squeezed in their cage.
Even if they say no to the interrogation straightaway and you believe that, you can still change the stakes, ‘you haven’t cum, but have you masturbated?’ and if yes do as above, if no, ‘you haven’t even touched yourself?’ A final no to that and you can ask ‘well have you watched any porn without me?’
He’s a guy, he almost certainly will have done some of those!
Stuff like this, for us anyway, is so much hotter when there’s a reason for doing it. I find it almost impossible to be mean like that for no reason at all, but him admitting masturbating totally makes me feel much more into all of that.
Try it and see!