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

It’s Lipstick Time!

Don’t be caught out with a cheap lipstick on Halloween night! A high quality lipstick is a great way to lift your game. Try treating yourself to a great lipstick like the one listed here. There’s a self hypnosis video below to help make the most of it!

Welcome Rini…

Rini – one of my newest members.

What a delightful surprise to find a lovely new member, Rini, today, who kindly sent this lovely pic. I look forward to all email from my members and try to answer each and every one. Sometimes that not easy, as I usually have to field around 130 emails a day. If I get a little behind (phrasing), don’t be too surprised. However, I do eventually get to everyone.

I’ve been amazed by the growth on the site. We are now listed as one of the top crossdresser websites in the world. That’s due to the loyalty and kindness of all my followers.



This Halloween you can crossdress like a winner!


‘I think what you need to do,’ Said Julie, ‘is come up behind, give it a good push and then reach around and jerk it off.’

This all sounded strangely familiar to me, which was a little surprising as Julie and I were standing in Sylvester’s workshop, looking at the rear assembly of a D6 Catapillar tractor. Now, anyone familiar with the difficult task of replacing what Sylvester told me was ‘rear bearings’ of the drive system, will understand precisely what Sylvester and Julie were talking about.

‘I think it needs more lubrication,’ said Sylvester. Well, that certainly rang true.

‘You need to pour hot oil over it,’ said Julie. ‘That will make it expand.’

‘I’m sure it would.’ I chimed in, helpfully.

Julie, as any of those who are in either my Admirers Club, or the Premium Program, will know grew up in a farming community. It’s surprising what you get to learn growing up in overalls.

However, that’s not the main reason I’m writing to you. We are heading toward Halloween – that most important date in the Crossdressing Calendar. I am always interested in hearing your Halloween costume ideas.

Mildred, from Colorado Springs writes:
“This year I’m combining an office formal look with a horror theme. I’m dressing as my former mother in law.”

This seems a creative approach and is sure to yield some amusing comments when shared on Facebook with family members. We always encourage sharing.

So, I’d love to hear some of your ideas about crossdressing for Halloween. You can comment and share on this Blog Post to be sure plenty of ideas are out there.

And don’t forget there’s a host of Breast Forms and Skirts, as well as other ideas of things to order on my website. Be sure to check out my Shopping List. These can help complete that perfect costume.

Let me know how you get along. If you haven’t already done so, you may even buy yourself a special Halloween gift and sign up for my Premium Program if you haven’t already done so!



Paul Simon - You Can Call Me Al
Here’s a quick competition. The first correct response wins either a free Premium Program membership, or free Little Black Book membership – whichever you prefer.

Here’s the question: What common factor is shared in this video and another of the newsletters I’ve produced? For new members, back copies of the newlsetters are carried on my blog.

Need crossdressing supplies? You first place to look is Fiona’s Shopping List. In this evolving list of suggestions and supplies you’ll get some ideas and suggestions, and even be able to add you own thoughts as well. Take a look, and maybe even order some products online. Have fun.

You may also want to look for some very nice suggestions for wigs – to help create exactly the look you desire. Or maybe you’re looking for a sophisticated solution for eye makeup.

I always love to suggest ideas for leotards, which really are the corssdressers friend. Take a look around and see if something tickles your fancy!

I can help you with everything from a body stocking to a breast form!


Are you reading the exciting adventures of Andy in “Clothes Maketh The Man”?

Manipulated and taken advantage of by the evil Devina, Andy finds himself compromised into dressing. You’ll never believe what follows!
If you haven’t yet dived into the extraordinary serialised feminization adventure you can find it here:

Read the story – Clothes Maketh The Man http://fionadobson.com/clothes-maketh-the-man-part-1/

My Little Black Book is now available for as little as $2.95 a month. What a wonderful way to connect with other crossdressers.

Email, chat or Skype with new friends around the world. Get in there today, by joining for just $2.95 HERE Be sure to email me after you’ve made your payment, so I can set things up for you.

Do you remember the first time?

Hi, I was chatting with some of my members online the other  night and we got to talking about our first time. I don’t think any of us really knew what we were doing at that time. I was about 5 when I first tried on a pair of black panties. My cousin had been over, and they’d been left.

I think my mother must have washed them and put them in my draw by mistake.  Either way I found them, and realised they weren’t mine.  I tried them on all the same, and I can remember thinking it was naughty. I can also remember getting an erection – which was definitely a little strange.

For some of us, it was our sister that played ‘dress up’ with us. For others it’s some other situation completely. Have a listen to this great newsletter by Katia Thornwood, one of my friends. It’s a little unsettling, but shows a slightly different slant on the whole thing.

It’s Playtime With FIona – and Ken’s been a bad, bad boy.
Of course we all have a different path into this – and for each unusual start there’s an unusual outcome.  I know so many men who crossdress, and hide it from their wives, only to fnd later (when their guilty secret is discovered) that their spouse really likes the fact that they like to dress up. And of course there are the ones that go the other way.

In the end, we all know we just have to be the person we’re meant to be – and find ways to accomodate that. There’s good ways and bad ways to do that.

I’ve just added a new page to my site that will help people understand a little about this. On my site you can tell your own story in the comments section of the following page – http://fionadobson.com/my-first-time/.  You might find your own story is not so unusual. It’s a good thing to share.  Don’t forget to register on the site. That way you’re sure to get a lot more out of it.

If you are interested there’s a little about my own journey here: http://fionadobson.com/the-three-reasons-i-couldnt-stop-myself-from-crossdressing/

Ironically, it’s often not until later in life that many people embrace this behaviour. Perhaps it’s just when we feeel more comfortable with it.

Now, Sylvester, my mechanic has just pulled into the drive.  He wan’t me to take a ride with him on his chopper. Have a lovely evening!



You won’t believe how fast a homeless person can run!

You won’t believe what happened to me on the way home the other night. Now I can’t even go to the local Whole Foods store!   I’ve just got back from a great break in PV, Mexico. So, I arrived home and there’s no milk in the fridge.

Julie, has been looking after Hannibal, my dachshund, and I knew he wanted a walk with me, so I took him along with me to the store. It was pretty late, and some of the staff were taking in the flower display from the street, where they always look so lovely.

As I was looking at them, and thinking how fresh they were, and how they’d freshen up my apartment, I thought I might buy some.  I turned my head at that moment to see Hannibal, my dachshund, peeing on the homeless guy who sometimes sits there.

He looked back, mortified, his legs wet, and a pool of pee spreading over his cardboard sign, which said – ‘I’ll accept anything.’

It’s absurd, but I couldn’t help thinking that was a rather open offer. I said I was sorry, reaching in my purse,  and found all I had was plastic, and a few peso coins. He wouldn’t take the plastic, and the pesos were no good to him.

I ended up making my apologies and leaving, hurrying inside the store. I felt awkward, though probably a little better than he did.  I must say it was a silly and embarrassing incident, but there it should have rested.

However, fate was not going to be so kind. The following day I had some friends arrive to stay.  They are Ukrainian and the wife, bless her, decided I should have borscht for my lunch and cooked some up.

This was clearly well intentioned, but not my favorite form of soup.  I’m more of a clam chowder person.

Either way, I dutifully took the borscht she’d made with me to the agency, when I left for work. It turned out we had a business lunch that day, and I didn’t get to eat her soup, which I am sure would have been delightful. Instead it remained in my bag, until I noticed it there on my way home. Thinking I would be a little devious, I decided to toss it out of the car window, and say to my guests how wonderful the soup was, and how grateful I was that she made it.

So, there in the very slow moving traffic I lowered my car window, and was about to pour it into the street, when the traffic came to a complete halt, and I found myself next to a particularly angry looking biker. I gave him a smile, but bikers and crossdressers don’t always mix well.

He looked back with disdain. I though I’d better not de-borscht myself in front of him. I gave him a cheeky smile and a week, and he scowled back at me. I lowered the passenger side window and tossed the borscht from it’s tupperware container.

That was when I heard a shout.  It seemed to come from beside the car. I leaned over to the passenger side of the car and looked out on the ground, and there at the foot of a parking meter was the homeless guy, covered in borscht.

He’d moved a few blocks down the street, but it was definitely him.  He turned his borscht covered head in my direction and then recognized me, and said ‘You!”. As the traffic moved on he scrambled to his feet, and started chasing after me in the slow-moving traffic. He was bundled up, but hurried along very quickly after me.  It was just a little frightening.

I raised the window, but it was quite surprising how quickly this poor fellow could move, sprinting beside the car and banging on the window.  All the while he was shouting and making a terrible fuss. Only when I caught the lights just right could I accelerate away fast enough to leave the fellow, with his flapping arms and wailing.  I felt terrible for him, of course, but what could I do?

I pressed my patent leather clad high heeled right foot down and left the poor chap in the rear view mirror. In a face-off between the V8 in my Buick and a homeless person, the Buick generally wins.

I puzzled over his turn of speed for a while till I got home. He really was very quick for a homeless guy.  Now, those of you who know me know that I am a kindly soul. Of course, I have my peccadillos, but I am generally a simple type. I feel no malice or unkindness to homeless people.

I was thinking this as I walked round my vehicle checking that it hadn’t been damaged by his banging on the window. That was when I noticed the glove caught on the door handle.

No wonder he’d been shouting so loudly as I accelerated away.

Oh, well. What can you do? I hope you’ve enjoyed this little story from the world of FionaDobson. Http://fionadobson.com

Don’t forget, I’ve got many free videos for you on Youtube, and soundfiles on Soundcloud.
I had a lovely email from Gunnar, from Iceland, yesterday. He had listened to one of my Youtube videos about ideantity and the importance of having a gurl name.

“I love your youtube videos. In one about female identity you say that its important to have a girl name for my girly side. I have always had problems coming up with a name that sticks. I ask you thus for help to find a girl name for me. “

Asking a girlfriend or emailing me for a suggestion, and telling me a little about yourself, is a good idea if you’re stuggling with this.  Identity is a very importaant part of crossdressing.  For many people the idea of dressing is a means to step into an alternative identity. A huge part of that is thinking what name reflects that identity.  Is she a gurly girl, a tomboy, or perhaps a very professional individual.

One great way to select a name is to type into Google, favorite baby names of (insert your year of birth). The result will list the top few male and female names.  Choose one of the top five. In many instances this will feel just right.

A name like ‘Candy’ may not suit that identity if it’s a person that is most at home in a Channel suit. Equally, ‘Olive’ or ‘Maud’ doesn’t much sound like a slutty vamp. Half the fun of dressing is creating the backstory of this character. If you want a fun exercise sit down one night and write her Resume, as though she were applying for a job.  As you develop the character you’ll find your ideas of who she really is clarify. There’s a reason why we say ‘Accept yourself as you are – create yourself as you wish.”

As you explore the idea of alternative identity, you may want to think about the various aspects of who ‘she’ really is. Is she playful, or studious? Does she take life seriously, or live on the wild side? Eventually you’ll realise that crossdressing permeates every aspect of who you really are.



Meet Aunt Pearl – Serial Trophy Wife and Gambler.

My aunt Pearl always used to say that you don’t win the lottery unless you buy a ticket. I remember the words echoing in my ears as they carted her off to rehab yet again, for her gambling addiction.

She was not only a serial gambler, but also a serial trophy wife. Her habit allowed her to work her way through the fortunes of six husbands, some of whom died in what can only be described as mysterious circumstances. Fortunately the standards of police investigation in Northern Rhodesia at the time were not quite up to the standards of  CSI tv shows today. One went riding on his ranch, and was never seen again. Another choked to death in a tragic sausage eating competition (no surprises there), and another had a mysterious heart attack while taking his daily exercise.  No one would think playing bowls could be so strenuous.

Needless to say, Aunt Pearl died a very wealthy woman. When asked where her wealth had come from she would often reply that one of her husbands had been involved in the ‘underground’ doing secret work during the war in London. This seemed very cryptic, and it’s certainly true that she did generally marry older men, much more frail than herself. One had indeed been in London during the war, though he worked on The Underground, driving a train. It was he who won the lottery and was the basis of her fortune.

You doubtless wonder why I am sharing these intimate details. Well, I am still sunning myself on the beach here in Puerto Vallarta, Mexico. A flat tummy is good, as far as it goes. A bronzed one is even better. I’ve been getting some help from Juan the masseur, who has helped in so many ways. He’s rubbed all manner of things on my body to improve my tone.

My presence here is due in part to my cashing in a few stocks and investments. I always make a point to have a small portfolio of shares; as Aunt Pearl said, ‘you don’t win the lottery if you don’t buy a ticket’, after all. I am not suggesting you take investment advice from a crossdressing femme like me, but this market feels right for an adjustment. I can’t help thinking it’s about to slide for a while. Best revisit those precious metal stocks. They look a lot more secure than most right now.

So, I cleared a few positions and slid down to Mexico for a couple of weeks. Juan is doing a masterful job of keeping things up with much more certainty than the current market.

I have been learning some useful Spanish phrases, which I will list for you at the foot of this message. Juan is very talented, a master of tongues. He said to me just the other day that he envied my good luck on the market.

“If I stand close to you, perhaps some of that good luck will rub off on me!” He said with a laugh.

I smiled at him, looking at the rather obvious bulge in his speedo, and replied that if he stood much closer it would be more than just my good luck that would rub off on him.

Have a wonderful week, and remember – “Accept yourself as you are, and create yourself as you wish.”



An unexpected guest.


I must say that this week has been an extraordinary handful at the advertising agency. I have found myself torn between a number of difficult situations.

The first and most difficult was with one of our public relations clients, who for reasons of discretion I will help remain anonymous by just using her first name. From time to time, conserving anonymity is a discreet and essential part of the work of our public relations division, and I am often asked to help that side of the business out.

So, I will just use first names, as I am sure you will appreciate the delicacy of the situation. Well, anyway, this week one of the agency’s top clients suffered a somewhat humiliating piece of news which required her to remain out of reach of the press. Of course, this is the price of celebrity. As her marriage has unraveled the press have been all over the story. With this in mind my client and friend, we’ll just call her ‘Angelina’, was in need of a quiet place to retreat away from the media.

It’s not the first time she’s visited, of course. Going out for a night on the town, in glorious Montreal, is one of her guilty pleasures. We’ve had some wonderful times, on more than one occasion being mistaken as sisters.

She hurried through from the airport, one morning this week, only to find Ali’s smart car parked in my driveway, so she was unable to drive directly into the garage. She called me on her cell, worried that the press might be hot on her high heels. She called me in a state of excitement and quite breathless.

“It’s all right,” I said, calming her. “Just feel free to use my rear entrance.”

So, it’s been a week of tearful reminiscing and comforting my good friend. But then again, what’s a gurlfriend for?

Next week I’ll be traveling south, and will be sure to keep you informed about what’s going on. In the meantime, what a great time to upgrade your membership and see what fun we can have dressing you up and putting you through your paces. If you haven’t yet listened to episodes of Fiona’s Inbox this would be a great time!