Sylvester enjoys a good pounding.

Sylvester, my mechanic, enjoys a good pounding now and then.  Don’t we all? And that’s precisely what was happening the other day as I entered his workshop.

“What on earth are you doing?” I said, as I watched him sitting on a stool, beating a piece of metal on an anvil.

“It’s called..” bang, bang, “contouring.”

The heavy blows were shaping the metal and shaking the entire workshop. He held the glowing metal with tongs as he worked on it with the hammer.

“Well, that’s not how I do it,” I replied.

“Contouring the piece,” he said as he continued bashing the hot metal with a heavy hammer. Once satisfied with the shape he dipped it in a pail of water and it gave a satisfying hiss, steam rising as it did so.

This did, however, remind me to post something for so many of my members who are struggling with make up advice.  I often steer clear of this, as there are so many wonderful sites giving great make up tutorials. Most of these are run by women who have been excelling at this since they were 7 or 8 years old, and I realise they are much more accomplished than I. However, I do feel that so m any of my members need a little guidance, I try to select the best ones to reproduce here.

Contouring is also of special interest to my gurls.  Most of us have facial shapes that are quite masculine. However, with the correct contouring we can refine the shape considerably. As my friends who are drag queens have demonstrated many times, good contouring completely changes the way people see your face. In a busy club drag queens, like high heeled feathered galleons sail across the dance floor and we’re naturally in awe of their appearances, their faces sculpted like Greek goodesses. Knowing something of these techniques is a valuable skill. While many of us will never come close to attaining the skill levels some of these performers have reached, we can do our best to improve our makeup skills, nonetheless.

Have a good look at the video above.  I’m sure you’ll learn something valuable. Hopefully this version of contouring your face will have more positive results than using Sylvester’s.



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Do you know your eyeliner from your lip liner?

Do you know your eyeliner from your lip liner?

When you first grab your lip liner and use it as an eyebrow pencil you are doing nothing more than most 11 year old girls have been doing for the last forty years. Many of my members experience feelings of disappointment and failure the first time they get up close and personal with make up. As a result they feel disappointed and often quite upset.

Let’s let that go right away. Here’s why. Most people who crossdress attempt to emulate beautiful women, in most cases who have been using makeup with their little girlfriends from the age of 11, or thereabouts. When a middle aged man attempts to look like a 20 year old woman for the first time he is likely to meet a level of technical resistance. In fact, he’s likely to make a dogs dinner of the process. 

It takes years to get it just right. It’s possible to make a reasonable job of it quite quickly, if one practices regularly. In fact, using a few Youtube tutorials you may get quite good at it before long. One of my best friends daughters has helped me tremendously, as you can understand my friends are very accepting of me.

Like everything worthwhile, make up takes time and practice. It’s something that’s a lot of fun to do, and so practice can be thoroughly enjoyable. I like to focus on one particular aspect a week. I may spend one week just on eye shadow, and another on lips, and then move to working on eyeliner or eyebrows. Either way, expect to take a while at it, and don’t worry if it’s not right first time. You are going to have fun working at it, but don’t set your expectations to high at first. 

The other thing to keep in mind is that a man in late middle age is unlikely to pull off looking like a 21 year old whore. Yes, it’s true. You might get to look like a middle aged whore, or better still with a little practice, a sophisticated middle aged woman, but don’t get disheartened chasing the unattainable. Having a good idea of what you are trying to achieve is a good plan. Again, don’t expect immediate success. It’s ok to take your time. Enjoy the process, and you will get there.
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Think of this as a good example of how not to do your make up. Generally it takes a little more time, and should be somewhat more enjoyable.
To put a little further clarity on the subject watch the amazing video below of Boogie, a remarkably brave singer, who had the courage to illustrate how very different the image her video audience has of her, and the reality of her looks is. I believe it takes a great deal of bravery to own the fact that you are not quite the person the public is sold. The reason I include her here is to demonstrate how the media create  a version of femininity that is in many instances unattainable, even for very attractive women. It’s hardly surprising we have the high rates of eating disorders in society that we do.
Boggie is a very talented Hungarian singer, and her song illustrates how what we see may not be the reality of the individual. For those interested, her song is a powerful statement about the value individuality and of the self over the brands we are sold.
For someone crossdressing it’s important to realise that perfection may be a goal that cannot be achieved. That said, beauty is not. There’s a subtle but very important difference there.

I hope you progress toward it and find it without too much pain.



A man at my backdoor, with an enormous tool in his hand!

As I started work on this today I was surprised to find my neighbors son, Max, at my back door. He was standing their holding an enormous tool in his hand. It quite took my breath away!


I said to him, “There’s no way you’re coming inside with that!”

He was, however quite insistent. I explained to him that if he had to go about waving that enormous thing of his, he should try seeing it was properly lubricated and prepared. Finding some oil I took it in my hands and worked the lubricant into it.

Now that I think about it, I don’t think Max had experienced someone doing this to him. A crossdressing gurl just taking control like that. I guess he may have felt a little over excited. who can tell? Life is full of these unanswered questions. Like why my friends always use my rear entrance, and not the front door.

Max seemed to enjoy the attention, and I knew he was excited to get inside. As I worked the lubricant deeper and deeper, and stroked his tool I could see he was becoming more agitated. These young boys are so easily overwhelmed. It’s so important to maintain eye contact, when someone is getting near the peak of  their anticipation, don’t you think? I gave him the can of oil and left him to it.

I turned my back on him, and said I had to get an email off to my friends, and the sight of me walking away from him was simply too much. I think he took one look at my bum in my tight leggings and was squirting his fluid everywhere! What a mess. Anyway, I have to get on with this email! When I first asked him to help me with some repairs and chores this was not what I had in mind.

But that’s not the main reason I’m writing to you today. I thought it might be nice to focus on two things in this email. The first will be moisturizing and the second foundation. These are two essentials for anyone wishing to feminize their skin a little. Moisturizing takes care of the tone of the skin, while foundation looks after color.

Regardless of age, male skin is often left untreated and dry because we are taught from an early age to wash, often using harsh soaps and no further treatment is really encouraged. What I’d like to encourage here is the regular use of a moisturizing lotion around the eyes and the sides of the mouth and nose area..

In your on going quest to feminize, this can be quite enjoyable. Those who have been following me a while will know I am a fan of gentle and subtle change. To start moisturizing every day, following a shave and brushing your teeth, is an almost undetectable but enjoyable process. You will soon find yourself feeling more feminine and your skin quality improving. Likely no-one but you will notice, but you will feel a little more feminine with this simple start to the day.

Now, as far as foundation goes, this is possibly something you don’t want to put on everyday as it is likely to be noticed. Although later, as you become a little more proficient at bringing subtle changes into you life, you may want to start using a little foundation each day, at first it is something that you can start practicing in private at home.

Doing self portrats? Foundation takes away the shiny reflections of your skin in photos. Yes, if you are into taking selfies when you dress, you need to know about foundation! To some degree you can achieve the same effect with a little talcum powder, but too much and you look very pale. Rather as though you’d walked in on Max playing with his tool, actually.

You can buy foundation at virtually any drug store. If you have to, asking the assistant to help you, ‘for your wife’, you’ll find they jump right in. Now, while the safest thing to do is go for a general mid tone foundation, at least to start, if you do need to choose a particular color here’s a helpful tool that will get you started: First choose an undertone, and then your skin tone, and it will list a range of the most available foundation types, along with prices etc..

Next time you decide to take a few selfies be sure to put on a little foundation first. It will make all the difference! For a great tutorial about how to apply foundation, try this Youtube video:



Looking back to the early 1990’s, this video looks a bit different today.

It’s Toenail Tuesday!

If you’re locked down and wondering what to do, join us in our Elite Whatsapp Group and post your painted toe nails. We enjoy chat and ideas about crossdressing, and everything else, for that matter. On Tuesdays we do ‘Toenail Tuesday’ and share pics of our painted nails.

Come on in and join the fun.

It’s Lipstick Time!

Some of my members just aren’t able to find the time to dress fully. Tonight’s self hypnosis file will just let you enjoy a quick game that I think you are going to find a lot of fun.

Where to start with make up? Our Whatsapp Group discusses.

Join our Whatsapp Group to take part in these discussions.

What a busy day it’s been in our Whatsapp group.  I thought I’d just share a little of the conversation there, to give a bit of an idea what it’s like in this great and supportive part of the world of Fiona Dobson. You can follow the conversation below and see that One of the members had been stumped when trying to think about what make up to buy. They then asked the group.

This is what followed. Keep in mind Lenni is one of our cis female members.

Lenni: Hmmm… how did I start with makeup as a little girl? Mascara, lip gloss, nail polish. When I mastered those (mascara takes some mastering)… add eyeliner, blush, and proper lipstick. When you can do those without ‘colouring outside the lines’, add the fancy eye shadows. I learned the lipliner trick when I turned 40. (My mum tells me, sorry honey but ladies over 40 need lipliner. Your lipstick is bleeding into your wrinkles) 🤣🤣🤣

Katy: Thanks Lenny will bear that in mind

Katy: Once I have clothes I can see about posting pictures if I am brave enough.

Katy: Just don’t laugh at my feeble attempts.

Lenni: No one in this group would ever!

Bridget: Oh don’t worry about it, I have feeble attempts all the time. Eye makeup is like the Bermuda Triangle for me

Continue reading “Where to start with make up? Our Whatsapp Group discusses.”

Fiona’s Shopping List

Fiona’s Shopping List

tumblr_o9a40kUvwr1sq920to1_500Here’s a short list of things you are going to use during my program, or generally, as a CD. These are not necessary from day 1, but as you go forward you are likely to pick up bits and pieces on this list.

They are explained more deeply in the Premium Program, but you’ll likely figure out why you need them as you go. Got any ideas of things to add to this list? Please add them in the comments below.

The idea is not for you to rush out and buy all these things at once. It’s more a case of pick them up if you see them on sale, or get the opportunity to acquire them now and then.

This might also be considered a ‘starter’ list. For many of us, the acquisition and creation of a look and a wardrobe is a big part of the fun of crossdressing. Enjoy putting these things together!

Make up



Matte Blush

Eyeliner pencil


Matte eye-shadow without shimmer (harder colors come later)

Brow pencil


Lip gloss

Lip liner

Make up remover and wipes





Garter belt



Sports bra

Leggings – Colorful


Body stocking

Body shapers (waist cincher, spanx shapewear etc)

Teddy or camisole

Pastel Tee Shirts

Mini skirt

Mini Dress

Summer sun dress




Eye lashes (self adhesive)



Ear rings (clip on)



Nail polish

Nail polish remover

Other products

Moisturizer and skin care


Cosmetic bag


Make up bag

Body scent and fragrances

Body lotion

Be sure to add to this list in the comments below.