Having a sissy in chastity is a lot like having a rechargeable battery.

Orgasms for your sissy? No Mas.

Sounds funny I'm sure but there is rhyme to my reason.

Chastity, like many other things, isn't a magical pill that will fix all your problems. Diet pills while they will work to remove pounds if you aren't careful you'll gain it all back. You'll need to do maintenance after the fact to keep the weight off and it is something that most people do not do. That ab blaster is not going to give you abs w/o the proper diet to rid the fat from your belly.

The basis for orgasm control/denial is founded, in part, on the idea that while the male is interested in pursuing sexual release he will be more solicitous of the lady’s pleasure, and in general more amenable to various services for her. For some, an additional motive is that more time between his releases will make them more powerful and pleasurable. However, the truth is that these effects are a complex mix of psychological and physiological effects, created by repeated “teasings” or other arousal which engage his desires and build at an emotional level.

So chastity isn't, on it's own, going to make the sissy (I always talk sissy on this site but this can also relate to your male submissive/slave), become more submissive or sexually frustrated. There is work on both ends that needs to be done in order to achieve this goal.

If you do not make sure that your sissy is sexually frustrated then it will not have the affect that you nor your sissy are hoping for. It'll just be another thing that is in your lives. It's an attachment on her body.

This is where the seed of the rechargeable batteries analogy flowers.

Pray tell how?

I said that in order to keep the game moving forward you must make sure that they are sexually frustrated but you may ask "How in Sam heck am I to do that?" It is very simple actually. There are three things that you'd want to do and I'll enumerate them here.

1. Teasing and Denial
2. Ruined Orgasms, CBT, Post Orgasm Torture
3. Prostate Milking

Essentially do you not want your sissy to have a pleasant orgasm. If you can just do ever let them have one again so long as there are no medical issues, of course. If you can keep her from having a satisfying orgasm you'll keep your sissy at the height of her erotic energy and she will not be able to resist your charms. Or whims or beatings or humiliations or cuckolding.

Tease & Denial

This is where you want to start. T&D is the easiest thing you can do and can be so powerful that the other two aspects of this game can be done sparingly. The T&D will make your little sissy/slave want to explode. There isn't much that you need to do and it's different for each sissy. Whatever the trigger is for your sissy is what you'll want to focus on.

For instance, me, it's about dressing and cuckolding. If my mistress talks about how exciting or fun it is for her to see me in sissy garb with a nice pair of stockings/pantyhose that is enough for my clitty to want to break out of it's metal cage. If she touches me or teases oral sex it will hurt but it's enough to make my little dicklet's balls begin to fill. Serving, bondage, humiliation et al are all things that excite me and I'm sure some or most if not all of these things and more will do it for your sissy. 

Perhaps if she's like me then she'll love to underdress. When you go out for a dinner together have her wear her corset and stockings and a butt plug jewel under her boy clothes. Sure, she'll have to wear boy clothes every once in awhile and it's best when she's dressed up like a little slut but it doesn't mean that she can't be dressed underneath :)

Have her train to suck/take a cock and eat cum. I'm sure that'll really make her dicklet hard. Or, if it's in chastity as it should be, then it will try to get hard.

Ruined Orgasms, CBT, Post Orgasm Torture

These techniques are different from the other two headings. You'll have to remove the chastity cage for most things in here to properly spike that erotic energy.

Ruined Orgasms

This one is cruel and so much fun. For you. I promise you that every sissy dreams of mostly the same thing and Ruined Orgasms & CBT are two topics that will show up in their fantasy list.

A ruined orgasm is simply an orgasm that isn't pleasurable. That means that you can put post orgasm torture because it diminishes the pleasure received from an orgasm it can be done before, after or including any of the other methods so I will discuss that one later.

There are many techniques that you can use to ruin an orgasm and one of the most popular is the release method. Once your sissy is going to have her orgasm just release right at the point of no return. She'll spurt but with no extra friction or pressure it is completely unsatisfying and, if you're lucky, she'll want to cry. You can even demand that she tells you when she is about to cum so that she is the orchestrator of the demise of her orgasm. It adds a little to the humiliation but also, simply put, it's funny.

There is the "stop gap" method. Instead of releasing you pinch the tip or close it with your thumb and do not let anything out. It's painful and humiliating. There are plenty of other methods that you can find online. 

Using a vibrator while your sissy is still in chastity and allowing her to cum is beautiful and merciful. It is also great because your sissy is still in clitty bondage and there is that reminder that while she came she still had to come in a cage.

Using a vibrator while your sissy is still in chastity and still ruining it is sublime.

CBT

CBT is shorthand for Cock & Ball Torture. Use humblers, flick the balls, squish the balls or put weights on them. All this and more. I'm sure that her clitty will be righteously hard.

Post Orgasm Torture

Post orgasm torture is quite simple. It doesn't need to be done with a ruined orgasm but it makes the experience so much more regrettable for your sissy if you do. This is a sub-facet of CBT since you are definitely torturing the cock and balls.

After she spurts many things happens to a male's biology once they do. They drop in dopamine making them not want to continue having sex or partaking in the affair. All that erotic energy goes away like magic and all those things that they said that they wanted they will not. Their little clitty also becomes extraordinarily sensitive. This is the important part.

When you keep touching, but more importantly here, stroking, that extra sensitive clitty it will be enormously painful for her. She will flail, she will fight, she will plead and she will do anything to stop you from stroking her. This is post orgasm torture.

Just be careful and have her tied up if you plan to do this. She may mistakenly hit you because she can't handle herself.

Prostate Milking

This one is the most humiliating. Once you have learned to do this you'll want to just, well, milk her. You massage her prostate and it'll dribble out in buckets (not in literal buckets but more than she normally does) and all without having to touch her filthy useless clitty.

Think of it as maintenance of the pipes. Or maintenance of your plaything/toy.

You've teased and denied her and you want her balls to be smaller because they are just too annoying. Or she's having more difficulty walking around and doing the tasks that she needs to accomplish to make you happy. You also do not want her to orgasm because that would mean that you'd have to start from scratch with chastity. And a ruined orgasm gives her a little bit of pleasure.

Well, a prostate massage gives her no pleasure if done correctly AND you empty out her worthless balls. Win-win-win-win-win. If you make sure that she enjoys her product all the better.

Some information on Prostate Milking.

Where do I go from here?

Keep teasing, keep denying orgasm, keep ruining her orgasms and milk as needed. If you can do it throughout the day.

It's what she wants so why not comply? Besides, keeping her in a high state of arousal is of great benefit to you :)

*curtsey*