Embarrassing sex stories are usually normal: I bumped my head during sex, or I accidentally broke my boyfriend’s dick while riding him

But Jack,  owner of the smallest genitalia I have ever seen, is at the top of my embarrassing sex stories list. It’s embarrassing- for him. It’s not even one of the many weird fetishes I have. It’s all on him. 

Let me set it up for you.

I’m in a hotel, and Jack is naked and stands in my heels. I’m on the bed, and I’m mocking him, all per his instructions. My clothing is not even sexy– jeans and a t-shirt. This is the saddest sex hookup I’ve ever been involved in.

Jack stands with his hands over his dick, shoulders tremblings. My gaze flickers over his reddened face, his little pot belly, past his coltish legs and at the high heels on his feet. “You get hard wearing my shoes, don’t you, you pathetic loser?” I ask him.

“Yes, m’am.”

“You like that it’s the closest you’ll ever be to me, my nasty foot sweat on your feet, don’t you?”

Jack says nothing, but nods. His balance shifts from leg to leg; he’s tired from being in the heels for the last hour.

The air conditioning of the hotel room kicks on, the scent of Febreze now between us. Yet I can still make out his sweat in the air. The pig keeps sweating from arousal, and not even Febreze can wash that putrid stench from my nostrils.

“Answer me, worm,” I demand, laying back on the bed, positioning myself to stare down at him.

“Yes, m’am.”

Talk about fuel for embarrassing sex stories! 

I gesture at his cock. “You know what makes you pathetic, Jack? That you asked for this. You knew your penis wasn’t going to satisfy me, told me how small it was, told me about how you wanted my shoes, and you’re still hiding like a little worm. What a loser.” I tap my fingers along my wrist, trying to think of how to humiliate him.

“I mean, I’m not even going to see it, you’ve told me it’s so tiny. So either show me your cocklet or walk out that door right now.”

Jack’s shaking hands move to his sides.

A pathetic button that pokes out at me. Laughter builds in my core, bursting out of my lungs in the most unladylike way. I snort a couple of times from sheer amusement. I wouldn’t even call it a cock!

And worst of all, that does it for Jack. His eyes shut, face red, and he comes all over himself.

Of course, I only know because he tells me so.


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embarrassing sex stories