How to feminize your man – Part 3 – with Oakley Dale


Now, you’ll remember that he’s been locked up in the chastity device for two weeks now, so he’s pretty desperate for anything he can get.  Well this is when you offer him a deal.  He really wants an orgasm by now, so you’re going to offer him something a little different. Here’s how it’s going to go.
Step 7
You’re going to tell your boyfriend that while you know he’s been behaving, he’s staying in chastity a while longer. You can be nice about this, or you can be nasty about it. You hold the key, so he’s pretty much at your mercy at this point. So, you’ll tell him that you really like using a dildo, and that his little dick isn’t really enough for you. In fact, you’d like him to use a strap on if he’s going to get with you.
Explain to him that the dildo is so much bigger, and it’s better for you… If he really cares for you, he can do this for you. And of course, he’s wearing panties every day by now, so you can add that as he becomes more feminine his dick shouldn’t really be used any more anyway.  He’s probably going to react a little negatively to this, but again, you hold the key… So, telling him to satisfy you first, and then maybe, in a week or so, you may think about letting him out of the chastity cage.
He’s going to squirm about this and be very resistant at first, but if you say that you really prefer a decent sized dildo, you’ll find he does want to play along eventually. He may expect to get to come, but that’s not really on the cards for a little while.
Assure him, “it’s better this way. Besides, you look so pretty in those panties. You’re hardly a man at all, really!”
As you allow him to pleasure you, keep insisting, “you’re a good little bitch. You like being my bitch, don’t you?”
Step 8
You are now really turning him. Tell him how he makes a far better sissy than he does a man. Explain to him that as a sissy, he must always defer to you and understand that you make better choices for him. He should understand that you lead this relationship completely and that sissies are there to please you, and anyone you want pleased. He should understand that only in pleasing you, will he find pleasure himself.
He should understand that this is for his own good, and that many men privately end up like this. This is best for you both, and he should know that he will always be happier this way.
As he learns more he will understand that while he’ll never be a woman, he’ll be a fine sissy if he learns to obey and respect you without question. He’s always been on this path, whether he realised it or not, and this is how he can be happy.
He should wear women’s clothes whenever you wish now. He will be craving sexual release, but this can only come when you choose. And that may be a while – for his own good.
Part of his training now should include using a dildo on himself for half an hour every day. If he does so, perhaps you may consider unlocking him sooner – but not just yet.
Since he will never be a man he shouldn’t be concerned about masturbating or even having an orgasm.
As you feminise your man, you should be prepared to take him ever day. Be sure he learns to thank you, and explain this is for his own good.  He needs to get used to it.
When you decide your sissy has earned an orgasm, bind her arms, remove her cage and make her ejaculate directly in her mouth. It will be the only way she will be allowed to cum in future. Then lock it again.
In future you always refer to your sissy as ‘her’ or ‘she’. At this point you have changed your sissy completely, and all further dealings with her need to be on the basis that she is your slut to use in any way you please.
Next week we’re going to talk about how you can lend her out to people and make your sissy into something of a plaything for others. That’s when it really gets to be fun.
You can always find me on or if you want to have an even close relationship with me why not join one of my programs on If you are very lucky I may even put you in my stable of paypigs and let you bring me all kinds of pleasure. But to do that, you’d better get my attention by sending me a little tribute. Learn how at

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