A Beginner’s Guide To Contouring.
Restricted content
Crossdressing for fun – a self hypnosis journey.
Is there a gurl inside you ready to be unleashed. Join me on the journey of self discovery that really will set you free. Would you like join my free feminization program?
Become a Patron!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!
Become a Patron!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.
😊
Fiona
Become a Patron!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. |
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. |
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. 🙂 Fiona |
Would you steal a crossdresser’s make-up?
Addressing the burning issues of the day, Jules asks the question on everybody’s lips; ‘Would you steal a crossdresser’s make-up?”
Become a Patron!Fiona’s Shopping List – Eye Shadow.
Since I had Sylvester do some work on my electrical wiring I have been having trouble with my fuses. Periodically I find myself bathed in darkness as the electricity goes out. I’ve had several electricians come to check the system, and another is coming to check the fuses shortly. Currently I blow three or four a week under the stairs. Frankly, I’ve had about as much as I can swallow. I think I should just replace the entire wiring system.
That, however is not the main reason I am writing today. I thought I’d include a little tip for all those crossdressers who are yet to master their make up, and let’s be honest, there’s a few!

Generally a girl starts playing with make up when they’re nine or ten years old. These are often forrays into mum’s handbag or make up draw and at first they are disastrous. However, particularly after playing with friends, they gradually improve. As they get older their makeup often becomes bolder and they learn various subtleties in their choices of color and their techniques.
Many crossdressers struggle, and get upset with themselves for not getting great results from the very start of their makeup use. This can be disheartening. I understand, and you should be aware that it doesn’t have to be that way. Be patient and practice.
While I don’t generally give specific make up tips – there’s many others out there who do amazing makeup tutorials on Youtube – I will offer this. If you choose subtle colors, using minimal amounts, you can gradually incorporate a few colors into your everyday regime without putting yourself into a position where you’re exposing yourself unnecessarily. A subtle amount of eye makeup to sharpen your look is a great way to feel feminine and to gradually improve your makeup skills.
The palette above is a good example of what you may want to start using. Nothing too garish, unless you are really ready to go full Ru Paul on the world. If you’re just starting out, applying a nice blend of shades now and then will be satisfying and even if you’re not completely ‘out’, can really help you enjoy your look.
After using make up for years I can firmly attest that less is generally more. Don’t be afraid to go for ‘subtle’. It will build up your confidence and if you can integrate it into your daily life. Then as you do gain proficiency you will find that experimenting with a greater range of tones is easy.
The other tip I’d add for anyone using eyeshadows for the first time is to be sure you have a selection of brushes. Applying the shades with a nice brush gives you even coverage and makes merging one color with another much easier. Using a little foundation on the eyelid will provide a smooth start point, though sometimes when you just need to grab and go, it’s not entirely necessary.
Enjoy the video tutorial below, but be sure to explore the Amazon link below for color palettes that might work well for you. In the end be sure to remember that practice makes perfect.
Don’t forget, you can join my Elite Whatsapp Group to enjoy chatting with new friends about your adventures with makeup. Check out the Elite Whatsapp Group here.
Fiona.
Restricted content
A man at my backdoor, with an enormous tool in his hand!
|
|
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.
Playtime with Fiona – Part 4 – Eyeliner.
This is a very basic training exercise for eyeliner. It’s all about practice. Let me know how you do.
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.

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.”Restricted content
It’s Lipstick Time!
We’re not always going to have the time to get completely dressed. Here’s a great way to quickly enjoy the feminine side of yourself.
This self hypnosis recording will help you feel comfortable using a little lipstick to emphasize the sensual nature of your personality. Be sure you have some lipstick with you when you do this wonderful exercise.
Fiona’s Shopping List
Fiona’s Shopping List
Here’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
Foundation
Concealer
Matte Blush
Eyeliner pencil
Mascara
Matte eye-shadow without shimmer (harder colors come later)
Brow pencil
Lipstick
Lip gloss
Lip liner
Make up remover and wipes
Clothes
Panties
Stockings
Fishnets
Garter belt
Bra
Corset
Sports bra
Leggings – Colorful
Heels
Body stocking
Body shapers (waist cincher, spanx shapewear etc)
Teddy or camisole
Pastel Tee Shirts
Mini skirt
Mini Dress
Summer sun dress
Accessories
Sunglasses
Wig
Eye lashes (self adhesive)
Bangles
Necklaces
Ear rings (clip on)
Belt
Rings
Nail polish
Nail polish remover
Other products
Moisturizer and skin care
Cleansers
Cosmetic bag
Suitcase
Make up bag
Body scent and fragrances
Body lotion
Be sure to add to this list in the comments below.