To Free or Not to Free. Is there a question?

Grace Leans: Reposting this thread here rather than in the chat room for any thoughts on the subject.
My boy has been in chastity for a mere two weeks now. I'm taking him to a dungeon party tonight. Always wondering if I should take him out of chastity for the night so he can have some fun with his (my) cock. It's never straight forward. I know he'd love to be released for the party but I also know his frustration would be exciting for both of us. Ahh, the paradox of chastity. Thoughts?
Update: I took him to the Dungeon and decided to keep him in lockdown. I hate to interrupt the build-up of frustration that time creates. Instead I got to practice my caning skills which left his ass looking quite red and swollen. I'm always surprised how much he can take. And as usual in the morning I have his full attention on making me breakfast and giving me an orgasm (sans his straining cock).

 

Further update for your reading pleasure....
After his caged outing to the dungeon party and some well deserved caning for a minor outburst earlier that day I continued his torment by applying some E-stim to him with the instruction to not touch himself during the hour or so he was freed. I graciously gave him a chance for a maintenance" release" with the condition that it had to be hands free using only electrical stimulation to get him off. After some failed attempts of reaching "resolution" I had to assume control of the box and increase the level beyond what he was capable of himself. With in a minute or so, and after some desperate begging, a somewhat ruined orgasm took place. Ah the labors of being a key holder. Happy Holidays everyone. G.L.