Crossdressing Style Icons – Fit Men Cute Boys in Skirts Dresses & Make up

To celebrate the release of my latest cross dressing fashion video I would like to share with you some of the best photos.

Of course boys wearing dresses in rural England is not a purely new phenomenon

In an earlier blog I introduced the androgynous super model (the link to that report is here). Those models make careers out of our inability to distinguish their male or female heritage.

Androgynous Supermodel Andreja Pejic

However there is another group of models that are unquestionably male but make a living by modelling clothes that you might normally expect to see in a women’s wardrobe.

In today’s blog I will present you with some of these iconic fit male models. Traditionally we would have described them as cross-dressing but today I would just refer to them as gender fluid.

As this website is dedicated to gender fluidity these cute boys belong here and I hope you enjoy this little collection.

Dress and make yourself up in the way that makes you most happy!

Pretty Boy Sally

PS. If you are not already a subscriber (its free!) the video is on my YouTube Transformates channel (link embedded in name)


Fit Naked Male Ballet Dancers – A Fem Boy Homoerotic Artistic Fantasy With Nude Athletic Guys

Having just finished my latest video about naked ballet dancers (only men this time – sorry ladies) I thought I would share the images with regular visitors to my blog.

One of the problems with adapting photos for wide screen YouTube viewing is that I can not always capture all the details in the space available.

So here are the, as they say, uncut versions. I don’t think I need to say much more here – the pics can do the talking for me.

If you have not seen the video yet and are interested the link is here.

Time to get out those dancing shoes! (Acknowledgements and big thanks to the artists/idols involved – thanks for sharing your talent)

Pretty Boy Sally


Cross Dressing Men In Stockings Suspenders Bras – A Trans Health Photo Review

Men who wear women’s underwear often take great care to keep their bodies toned and fit. Male cross dressing can even be thought of as a powerful incentive in the battle against obesity.

Cross Dressing Men work hard on their abs to complement attractive stockings, suspenders and bras

It has long been known that the homosexual community often takes an active interest in physical fitness and healthy living. Similar drivers exist in the trans community regardless of being straight or gay – we want to look good in women’s clothes.

The perfect image can also be greatly enhanced by your wallpaper choice

Cross dressing males have an added incentive to keep thin and fit. Women’s clothes tend to be designed to enhance attractive body shapes and are very unforgiving of excess fat.

Men feel more comfortable getting fitting assistance in the shop if they regularly visit the gym

In my earlier photo blog I explained some of the issues of sizing for trans men (the link is here). Even if you get a size that fits it is nice not to have an unsightly ‘overhang’. We all like to look nice in the mirror!

We all want to look our best in the mirror

To illustrate how well some men have crafted their bodies to complement well with ladies underwear I would like to share with you some photos which I consider to be iconic.

We all have different tastes – not all men feel comfortable wearing a bra with their stockings and suspenders

Clearly not everyone will have a perfect body for their trans wardrobe from day one – and I am certainly not into body-shaming. But as you look at yourself in your nice stockings and panties why not plan your next visit to the gym. Perhaps you could use the trip to show off some of your latest purchases.

I hope you enjoy today’s photo review (I am sure you will understand that not all the chaps feel the need to wear a bra). Big thanks to these iconic models for sharing their success.

Pretty Boy Sally