Yes, but only if you wear them backwards.

May I sleep in a wedgie tonight?

Yes but a bra connection wedgie

Can I wear female clothing under my male clothes tomorrow

Yes, but onlyif it is soiled.

May I cum in my cock ring?

Yes but after you edge ten times

Can I wear female clothes under my clothes tomorrow without doing something against my limits

Yes but only if you it it after
May I please poo it has been three days because I haven't been able to get permission

Sorry I was replying to the one above yours u may wear female clothing if u pee in it

What part of not against limits do people don't get

Sorry lol u may wear female clothing if u have something in our ass

I need permission to pee and eat my lunch

You may do so if your ass is plugged.

May I take these girl's clothes off?

yes a hour after you cum in them

may a take a shower

Absolutely!

May I take my plug out of my ass for a while and cum?

you can remove your plug OR you can cum

May I break a my chastity time ?

Ofcause you are not allowed! What are you thinking? Add 1 week of chasity instead.

My i sleep with blanke and pillow today?

Only if you cum on your pillow first!

May I sleep with my pajamas on?