My younger, much more experienced partner and I were discussing fantasies last night. I have this pair of 4″ pumps she is particularly fond of, and she mentioned she might like to be fucked in the ass with the heel. They are not stilettos, they are wooden heels, not completely rounded, albeit fairly slender. While I am not one to pooh-pooh anyone’s fantasy, I can’t quite bring myself to believe that this would be safe. Pain factor aside, this seems like it has the potential to be very damaging, especially in the hands (or feet) of someone who has no idea what they’re doing, like myself. Do you have any thoughts as to how I could incorporate her fantasy into our sex life without actually hurting her (and not “hurt” in the good sense)?
–Feeling Like a Heel
You mentioned that you’re inexperienced, so before you approach this shoe fantasy, you’ve got to get some experience with basic anal penetration and sex toys. Start out with dildos and plugs, experiment with different techniques and what your bottom likes until you get really comfortable with them. One of the earliest letters I received for this column was about shoe fucking. A woman wanted to fuck her submissive with the narrow toe of her shoe. You’re talking about the other end, so you’re wise to be cautious.
Whether stiletto or not, a high heel is usually pointed and inflexible enough to make it a less than ideal penetration tool, and since you’re a beginner, I am going to recommend a safe option: the bait and switch technique. Put on the shoes, taunt her, step on her, tease her, tell her how you’re going to fuck her in the ass with those terribly menacing shoes. Then blindfold her, tell her it’s because you want all her senses to be on alert and concentrating on this new and unique sensation. Hidden nearby should be a wooden dildo, selected because you said the heel was wooden. Wooden dildos can be hard to find, but they’re out there (my picks: NobEssence and Jildos). With the image of your shoe heel firmly planted in her mind, the dildo can be firmly planted in her behind! It will have a similar weight and texture, and if you’re good at it, she will never know the difference. When you’re done, drizzle some lube on the shoe heel, take her blindfold off, and everyone will be satisfied!