Fucking Yourself With High Heels: Kink and Safety

Last Updated on 9 September, 2025 by Cara Sutra

Dear Cara, I have quite a worrying obsession with my girlfriend’s shoes. She doesn’t know, but every time she’s out and I’m left in the house I have to fuck myself in the ass with her high heels. I find myself rushing back from work to get there before her, so I can have a quick play. I feel really guilty but I can’t stop. Is fucking myself with high heels safe? Any advice would be greatly appreciated.

Anon

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Hello there, thanks for your question. I meet many shoe and foot fetishists in my life and I can reassure you that you’re not the first and won’t be the last to have a high heels fixation.

A ‘fetish’ is defined as “a course of action to which one has an excessive and irrational commitment”. This is more often seen with a sexual overtone, whereby the action, activity or object of the fetish causes strong feelings of sexual desire and arousal.

I would ask you to take a deeper look at why you have this need to insert her high heels into yourself. It may be that you love the fact it’s a high heel penetrating you, a real shoe fetish, or it could be a way to realise previously untouched anal pleasure territory.

Perhaps you merely like the idea that this behaviour, which could be seen by many to be quite kinky and ‘dirty’, is done in secret behind your girlfriend’s back. Of course, the fact that she may catch you ‘in the act’ is sure to be prevalent in your mind at the time too, adding to the sense of danger and excitement.

Once you have made sense of your feelings in this regard, you can then make some safe decisions, as well as the right decisions for you, about acting on them.

If you determine that you simply have a love of high heels, why not try discussing this with your girlfriend? If she is the open minded type, you may be surprised by a positive reaction. You could make some purchases together which will fit your fondling fancies.

If you love the danger and secrecy, then it is a little more complex. Of course whether you choose to continue this pattern of behaviour is down to your own conscience, but I can’t really condone using your girlfriend’s shoes and high heels without her knowledge. Any secrets and dishonesty in a relationship is bound to come out eventually and she will be confused and hurt at your actions, in my opinion.

Whatever you decide, be SAFE. Let’s face it, inserting a standard high heel of a shoe into your rear is not the safest of activities. Even if you put a condom over the end it is liable to tear, due to the nature of the rigid heel material. High heels have a small pad on the tip which can come loose and away from the heel very easily. This could easily come apart when inside you and be sucked up into your anal area, leading to serious health problems.

The high heel itself could tear the delicate skin inside the anal canal, leading to bleeding and internal damage. Not sexy, not fun, not nice.

My advice is to buy anal sex toys designed for this area. Whether you use them for masturbation in privacy (or secrecy, if you need), or introduce them to your girlfriend as something you’d like to try, these toys are much safer for you. With flared bases and smooth designs, body safe materials and a wide range of options, you won’t be lacking in the anal pleasure area.

If you’re looking for a high heel dildo, there have been some high heels made with a dildo for a heel. As you can imagine, these are not cheap, but they may fit your needs.

Take a look at the Dilettos Stilettos on Etsy or alternately Ainsley T has some amazing high heels with butt plug and dildo heels for both aesthetics and use by fetishists.

Have fun in all your anal adventures and high heel fantasies but remember – standard high heels are not safe to use up your bottom!

– Cara Sutra