While I know there are tutorials all over the Internet, I thought this would be a fun topic to talk about with you sissy girls.

How to Start Walking in Heels

I know that shoes are expensive as all get out and if you are a sissy who tends to purge periodically (STOP IT!) you hate to pay for expensive shoes. You don’t have to! You can find cheap shoes at cheap stores all over the place. I also encourage girls who wear heels out of town to just get some cheapo ones in the city where you are so you don’t cry when you throw them away before going home.

All that said, there are ways to learn how to walk in heels gradually. I am going to show you different types of shoes with different types of heels, from chunky to stilettos and by the time you have made it through the range, you will be a sissy on the runway!

Chunky Heels

Walking in chunky heels is the way to start practicing how to walk. The thick heel offers a great deal of stability and if there is an ankle strap, that adds even more foot and ankle control. Of course, the lower the heel, the easier it is to walk.

Foot Positions When Walking

When you walk in heels, you do NOT walk Toe to Heel, a common mistake with many sissies learning to walk in them. You walk Heel to Toe. Your feet can walk a normal step apart or if you want to get fancy, you can walk like you are on a straight line.

Higher Heels

These heels are higher, but there is still a great deal of ankle control in the first 3 shoes. The 4th one on the right has the least amount of control for the foot, so should be worked towards gradually.

Note that none of these shoes has a pointy toe. I highly suggest you learn to walk in heels withOUT a pointy toe until you are an expert, then graduate to the most painful of the painful: the Pump.

Stilettos with a Round Toe

When you are ready for advancement, it is time to get yourself some stiletto heels, but still with the roundish toe. Notice that the first shoe on the left has ankle straps. That will offer more support for steadiness than the one on the far right without the straps. The third one has straps over the top of the foot as opposed to the ankle, so that is going to be medium support.

When you are ready to move to the stiletto with pointy toes, the most painful of the shoe category, go for it!


The one on the left has some flimsy ankle straps, but at least it is something. The others, you are balanced precariously in and must THINK when you are in them. I know Carrie Bradshaw can run in her stilettos, but the rest of us would break an ankle. Well, even Carrie can fall sometimes,

The point (pun intended) is, you have to really take it slow and easy in pumps like these. BUT, have FUN when you are in them! They are gorgeous, aren’t they?