He Asked Me To Wear Heels

When my friend suggested I sign up for online dating, I’ll admit I was apprehensive. I certainly didn’t expect to find myself in lust with a guy only a few weeks later. We had definite chemistry on the first date which ended in passionate kissing. He invited me over to his house for the second, and we both knew the night would end in more. He sent me a text the day before.

“Hmm…what are you gonna wear?”

“Any requests?”

“Heels and a skirt. And wear red lipstick.”

The dormant glamazon within me stirred. She rose to the surface once again. It called to her.

Yes—I would wear heels. And a skirt and the red lipstick too. But this time would be different. This time around I’d made a commitment to myself to be transparent in dating. To date in flats and minimal beauty products in order to give a preview of what daily life with me was really be like. Any guy who was interested would just have to take me as I was.

Instead on this occasion I wore a black mini skirt, red stilettos, and Lipstick Queen Scarlet Sinner. On the ride in the Uber I felt a little bit like a hooker…and it kind of turned me on.


He opened the door. I was taller than him in my red Barbie mules.

“You did what I asked.”


He led me into the bedroom. Then bent me over the bed, lifted up my skirt and spanked me.

“I like that you are so obedient.”

Oh, this is going to be fun.

Something was at play here that I hadn’t considered—masculine men are attracted to sexy women—to hot women. To women who wear makeup and heels. To women who exude sexuality. To women who look good on their arm. And I was reaping the rewards. His excitement was obvious and it was easy for me to please him this way. Turning him on turned me on as well. Ultimately I had turned myself on with my own fuckability.

To make peace with the barefoot goddess, I’ve placed wearing red lipstick and heels in the category of what sex columnist Dan Savage calls being GGG—Good Giving and Game. It’s a decree for sex positive people which states “one should strive to be Good in bed, Giving to one’s partner, and Game for anything—within reason.”

This was within reason.

After we had sex I took a shower, wrapped myself in a towel and caught a glimpse of my face in the bathroom mirror. My skin was rosy and clean. My eyes were shiny and bright. I looked about fourteen.

“You fucked all my makeup off.” I said to him as he laid on the bed.

“Yeah, that was the point.”

It made me smile. Because I realized that a wise man knows you are not your makeup or your high heels. He knows that underneath those things you are a woman with bare feet and a bare face. And that is someone I’ll wear heels for every time.

How about you? Have you ever dressed up to give someone pleasure?

Author: Eden Lighthipe

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