My Boss’s Sexy Shoes

Tonight I stayed late at the office. Really late. Long after everyone had gone home, I got undressed, put on a matching bra and panties and thigh-high stockings. I crawled under my boss’s desk. She keeps two pairs of shoes under her desk in case she needs to go into a meeting. I pulled up photos of her on social media and slid my cock to one of her sexy shoes.

She is an exceptionally beautiful woman of 54 named Christine. As I continued to scroll through the pictures of her, I was thrusting my throbbing cock in and out of her shoe, moaning loudly.

The cleaner had not come in yet, but I could hear him out in the hallway. I was too far gone to stop and far too horny to try and be quiet. To be honest, a part of me wanted him to hear me.

When I heard the deadbolt on the door unlatching, a thrill went up my spine that I cannot even describe. I wasn’t going to try and hide or be quiet so that he wouldn’t notice me. I just kept furiously humping her shoe. He didn’t notice me right away but I continued to thrust my penis in and out of my boss’s shoe. When he came over to empty her garbage can beside her desk, that’s when he saw me, and at that exact moment we locked eyes, and I pulled my cock out of her shoe and shot cum all over it. His eyes immediately went to my cock and my cum, but he didn’t say anything. He just smiled and let himself out.

Comments

Anonymous

by Anonymous on Apr 16, 2025 at 6:30 AM

I'm thinking of the "Little Old Lady Who Lived in the Shoe", but here you are, humping the shoe!

The thing about sexual fetishes like dressing up in clothing you wouldn't normally wear, being intimate with your boss, and humping someone's shoe...is that they're weird. That's what makes them fetishes. But if you are not hurting anyone, then I say, go for it!

If on the other hand you find that humping your boss's shoe leaves you less time and energy to hump your wife's shoe, then you have to stop.

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