Oakley Dale – Feminize your man Part 4

You’ll see from the first 3 periscopes in this series that you’ve got him used to taking instruction from you by now. You can find those easily by going to fionadobson.com and using the search box to find ‘Feminize your man’. So, your little gurl is behaving pretty well by this stage. She has a good idea that she’s never going to have sex in the way he used to have in his previous life. Now everything’s different.
And this is when you introduce – very gently – the idea that as a complete sissy her usefulness is defined entirely by her ability to give pleasure to others. This is going to take the form of service – doing chores, cleaning the house in a suitable costume, perhaps, but also sexually.
Introducing the idea by this stage is not really that difficult. By this time your sissy only has orgasms at your choice of time and means, and she should be entirely trained to know that she’s never going to have sex with you – unless it’s entirely your own choice.
As a woman this is likely to make you feel quite empowered, to say the least. You can always threaten to tell his friends, and you should have a nice selection of pictures to help convince him to be co operative by now. Ideally, though, what you should start to find is that he doesn’t really need to be threatened at all. Mostly, I find that my sissy’s want to do as I tell them. They are completely driven to please me.
At this point you’re going to suggest that maybe it would be better if he try satisfying a man. After all, he’s such a gurl now! Looking after just one man, for a little fun, would be the most natural thing in the world. In fact, it’s a reward for him.
He’s pretty well prepared physically to be able to do this by this stage, of course. He’s probably going to enjoy it. But, you retain all the control. Make it quite clear that you get to choose who he is going to satisfy.
It’s also important you explain that, however he feel, he’s to make your chosen stud believe he loves it. He should be told to gush over the man – ‘what a big dick! Oh my god, I just love it! I want it so bad!’
Make sure he’s prepared with instructions to tell the chosen stud how wonderful it is.
Now all you have to do is choose someone. I always choose an exboy friend. It seems appropriate. Of course, you could have someone in mind – it’s always fun to choose someone he works with, or sees regularly. It’s like a constant reminder of his feminine self and how it’s there at your disposal, not his.
I’ve told him so many times, by this stage, that the previous guy was so much more of a man, and that he is sweet – “but like a girlfriend really. And, I’m sorry, but you never really satisfied me as a man. And you’re doing so well as a woman.”
Now, when she performs for your chosen stud, you’ll want to help and encourage her. You may even find a nice pic or two helps keep him focused, and after all what better way to help her than share it with some friends of Facebook. And in the end, your helping her. She’s find out who she really is!
Now, I’d like to remind you that you can find some great help feminizing your boyfriend, or even finding crossdressers to date, on FionaCobson.com – In Fiona’s Little Black Book there’s hundreds of crossdressers just waiting to chat or even meet you.
You can always find more of me on OakleyDale.com – and I’ve got a special thing for you today. I’d love to hear from any of you who want to be a ‘special friend’ for me. My special friends are called Pay Pigs – and you send me something to get my attention. You can start by sending me a little tribute to oakleyxdale@gmail.com – you can learn more about how I can help you with this on OakleyDale.com

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 FionaDobson.com or if you want to have an even close relationship with me why not join one of my programs on OakleyDale.com. 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 OakleyDale.com.

How to feminize your man – Part 2 – With Oakley Dale – Crossdressing

You can find part 1 – here: http://fionadobson.com/oakley-dale/how-to-feminize-your-man-part-1-with-oakley-dale/


These instructions are very simple, but they take time. There’s no point rushing this, and you’ll fin it far more enjoyable if you invest the time and effort to make the changes lasting or even permanent. If you haven’t heard the first in this series, just look for the link on FionaDobson.com.

So, by this time, he’s wearing a pair of panties more or less every day. If he has to go to the gym or the pool, maybe you cut him some slack, but otherwise, he’s pantied and you shop together for nice feminine panties. Ask him which ones feel nicest, which feel they feel like they fit best – simply engaging him in the talk will help him say that he likes one over another – which sounds almost like ‘I like wearing them’. You’re actually conditioning him to like them as much as anything. Soon he’ll just put them on without you suggesting it, as long as you continually affirm how turned on it makes you feel.

The fourth task is easy.

One evening, out of the blue ask him to paint your nails. Simple as that… except you tell him how good he is at it “just like my girlfriend xxx. We used to paint each others toe nails hwne we were kids, and then make out, pretending each other were guys. It was pretty hot! Would you like me to paint your nails?”

If you get him a little turned on before you ask him, it will help, but he’ll likely say, “OK, but just one!” Just go along with this, and absent mindedly do them all. Don’t worry, he’ll play along. Once painted, refresh them every three or four days, and tell him that each time you see them you get so turned on you just can’t help it.

Next – Task 5.

At some point you’re going to have to begin something he may have wanted for years. If he’s ever talked about ‘anal’ now’s your chance to give him what he wants, though maybe not quite the way he anticipated. Next time you make love have a small vibrator, or adult toy, and surprise him with it. There’s a first time for everything, after all. Tell him, you like it because it makes you feel powerful. You love that he trusts you so much. Tell him you always wanted to and so few men let you do what you want.

Now keep in mind he’s pretty receptive to your training by now. He’s ready to do anything for this enhanced sex life. He’s also unknowingly drifting into an increasing submissive sexual role. You should be sure that you are stimulating him anally when he climaxes, and that’s going to be a feature of your lovemaking from this point forward. What you’re doing is setting up the association of him eventually needing to feel the anal excitement to achieve orgasm.

By this time, when he comes, you should be using language such as – ‘You’re such a good girl,” and “My little girl loves to be used, deosn’t she?” whenever you’re enjoying sexual intimacy. Believe me, he’s going to be so occupied enjoying himself, you won’t need to worry about what he is thinking.

In fact, at this point he’s going to be so receptive to suggestion during the process that he won’t even realise that he’s being programmed into a femme role. It’s going to seem like the most natural thing in the world.

On to Task Six. This is one you have to play very carefully. In fact, in successful feminizations of this sort, this is the tell tale task – the one that dictates what happens next.

Ask him if he finds that his orgasm is more intense following a period of not having sex. You should be recording each time you have sex up to this point, and you’re now going to find what the average period between nights when you have sex is.

So, if it’s every four or five days you are going to need to know that. Here’s why; you’re going to deny him sexual release for at least double the average period between sex. Now, he’s not to know that you’ll likely satisfy yourself, or make your own arrangements. During this time you should keep encouraging him, telling how good it will be.

When the time comes, and you do make love, he’ll be thrilled. However, you are going to pretend that you think he’s been jerking off and relieving himself. You want to try the experiment again. Only this time you want to be sure it really works, which is why you’re going to ask one of your girlfriends to get hold of a chastity device. He’ll balk at the idea at first, but you let him know it’s just for a few days.

Now, I’m happy to answer your questions – but if you’re enjoying this, then perhaps you should check out http://FionaDobson.com – where you can learn all about crossdressing. And if you want to feminize your boyfriend, be sure to look out for Part 2 in this 3 part series, by following me on Twitter and Periscope. That way you’ll know when I’m doing them, but they’re also on http://FionaDobson.com – You can also find more of my Periscopes at http://OakleyDale.com



How to feminize your man – Part 1 – With Oakley Dale

These instructions are very simple, but they take time. There’s no point rushing this, and you’ll fin it far more enjoyable if you invest the time and effort to make the changes lasting or even permanent.

So, here’s how you start – and I suggest you don’t really tell him much about what you’re doing. We all love surprises, right?

So, the first step is really simple. All you need to do is, one night when it seems he’s eager to have sex, and you can make that happen by teasing him a bit, or denying him anything for a while, you’re simply going to ask him to wear your panties while he makes love.

Now, don’t push it further. Just ask him to, and tell him it makes you feel really turned on. Most guys will go for this. If you need to, just tell him it gets you excited about a lesbian fantasy you have. Don’t worry, he’ll go for it.

You’ll probably find he likes this exercise, but the next one is going to be more challenging, so you need to be quite insistent. Wait for a few days, and keep telling him how hot it was when he made love to you in your panties. But now you’re going to ask him if he wouldn’t mind shaving for you. You want him to shave his pubic hair and also his legs.

When you do this tell him that you actually find that men’s body hair really grosses you out. You had a previous boyfriend who understood, and when he shaved it became so much more sensual for you. In fact he found it more intimate too, and the sex was way better.

After he’s shaved once, insist he keeps his genitals and legs shaved. Each time you make love tell him how you like it so much more now. Suggest to him that he seems to be enjoying it more now, too.

Now, you’re a week or so into this exercise now, which is when you tell him that you want him to wear your panties every time you have sex. Tell him, you’d do the same for him – and that you really admire a man who is so committed to pleasing you.

When you buy feminine razors, about this time, start buying him feminine razors. There’s little difference other than the color, of course, but you are beginning to condition him into this new behavior. At this stage he’ll have little idea that you are modifying his behaviour – but that’s OK.

In fact, it suits you just fine.

Now, I’m happy to answer your questions – but if you’re enjoying this, then perhaps you should check out http://FionaDobson.com – where you can learn all about crossdressing. And if you want to feminize your boyfriend, be sure to look out for Part 2 in this 3 part series, by following me on Twitter and Periscope. That way you’ll know when I’m doing them, but they’re also on FionaDobson.com – You can also find more of my Periscopes at http://OakleyDale.com