Mistress Stacey and Sub Legion,

Great questions.

First up: define what chastity means to the both of you.
Ask yourselves some questions.

When, if ever, do you want it broken?

Under what circumstances will Legion be allowed to climax?

Will there be consequences a climax occurs without permission?

Legion can you be honest with this about to your Mistress?

One simple way to get started is with submissive tasks.

For example,
an item of clothing, jewelrey -- a ring, chain, watch -- etc,
can be used for control. When Legion is wearing said item, Legion is under the control of Stacey. Period.

If Legion is feeling bolder, a piece of ribbon tied around a certain body part and worn under clothing might have the same affect.

From the moment the item is worn until removed with permission by Stacey, the chastity and climax control begins.

Stacey, depending on whether or not you enjoy watching or hearing your sub orgasm, you might enforce a time of day, or moment when your sub must orgasm for you.

When I started with my Nat, he had been "trained" NOT to cum! "Bloody hell," I thought. "I want that man to climax and climax often under my control."

I started with having him masturbate up to the point of climaxing multiple times per day. He could only finish when I was on the phone or chat and gave him permission.

We've got lots of threads around here on orgasm control and denial. The first step is to just get started. Think about the end result you want to acheive and take baby steps towards it.

To your success!

Ruby