Oh such sweet cheeks you say, no bum pun intended, this article is the second of three on creating a feminine “look”. There is an art to getting your cheeks to accentuate your face making it appear more feminine. As you are aware, there are many face shapes. In this article, I’ll concentrate on my personal  face shape which is square and in most cases, you’re likely to have a square face shape like mine.

After I have completed the makeup of my eyes and eyebrows, it’s onto my cheeks. Here, I have to make a decision based on what I have done with my eyes. If I’ve started with a cat eye look, I want my cheek bone and apple to reflect that, so they’ll be more pronounced.  If I decided on makeup for round open eyes, I would still accentuate my cheek bone but soften the apple of the cheek to match how my eyes were done. By now you have applied your beard cover (if needed) foundation (primer and base) and are ready to contour your face structure. I use a moderate dark brow contouring liquid with a 1 inch brush applicator and follow the cheek bone up towards my ear. But I also angle it a bit more towards the top 2/3 of my ear, this angle will help narrow the face and match up with the angle of cat eye, creating lift for my face. With your contouring liquid run your brush along and slightly under the jaw line. Apply some under your lower lip. Take your brush and apply it from your temporal area on one side of your face, across your forehead, at least 1 and 1/2 inches above your eyebrows ending on the other side of your face. Take a smaller brush, 1/4 inch and run a line along each side of the ridge of your nose. These two lines will be about 1/2 inch apart. Don’t be alarmed with how it looks, you have more to do yet. Now take another 1/2 inch contouring brush and use a very light liquid, not white and begin to fill the spaces. Apply some above and below your just darkened cheek bone, forehead, the length of your nose and tip. Looking in the mirror, yes, I feel your concern, but don’t be. Take a large blending brush and begin to blend in the darker contours. Take another blending brush and do the same with the lighter liquid contour areas. Repeat until the darker and lighter shades have no definite edge but you still have significant differences in the two shades. Once your pleased with your effort you can take a big breath and relax. You can now start to see the transition of your face from male to female.

I let my makeup bake for a few minutes and I use this free makeup bake up time to slip into my panties, garter belt and stockings. Or, if I’m using pantyhose, I’ll pull on my panties, hip padding, then my bodyshaper panty and finally my pantyhose.

With that done, I return to the mirror and apply loose translucent powder over my face, being careful not to get any on my eyes or brows. Brush off any excess and again map out your face. Even though we are concentrating on our  cheeks, I will include the nose but that could be an article unto itself. With your contouring powder, which often comes in either 2 to 3 shades together (mine has 2). I use the darker shade and 1 inch brush applying it to the cheek bone, keeping in mind the sharper angle I want and carry the shade along the same line I did with my contouring liquid up to the edge of my ear. I do the same with the lighter shade just above this.

En Femme Style

For me, I now take an almost white shade and fill the triangle like space, under my eye,  along the edge of nose on the face and back up towards the temporal area. You can run a darker shade down the edge of the nose and a lighter shade on the ridge of your nose using a 1/4 inch brush. With this contouring part done you have to blend the shades again. Try not to leave an edge between the two shades, blending is very important.

Now it’s time to sweeten the cheeks so pick the shade you want to work with your eyeshadow. Smile at yourself in the mirror and note the elevated part of your cheek. This is your sweetest part of your cheek, alas, sweet cheeks! Take your blush and apply it and start off with small strokes. Since I want my cheeks to work with my cat eye, I’ll  make my apple a bit more oblong or egg shaped. If your doing round eyes you can stay with a rounder blush application but still blend it out towards to ear.

Finally, we are almost there, I take a very light colour shiny highlighter powder and brush some on the top edge of the apple out and upwards towards the temporal area. I also run a little down the ridge of the nose. Take the translucent powder brush, tap out any powder and go back and lightly clean up any powder that is obvious. Here we are at the end of our cheeks makeover. You should see a change in the angles of your face. The contouring and highlighting is really simple, the areas that you darkern will appear further away, the highlighted areas will pop out. The makeup trick is to change the shape of your face to a more feminine look. Making your cheeks look the way you want does take practice but really it’s not difficult and the outcome is face changing or gender changing for that matter. I am a huge fan of MAC and have generally always bought their product because of their quality and because MAC stores are welcoming to all genders, drag and crossdressers.

Thank you all for reading about how to establish “Sweet Cheeks”. Please tab back up to the top of this article to see the finished cheeks of mine!

Sincerely, Melissa




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Denise Smith
Active Member
30 days ago

Thanks Melissa. There is so much great information here. No wonder you always look so lovely.

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