#1 Crush

A short story by Lauren Emily

This story contains: her and him, contemporary romance, lovers reunited, anal, firsts, toys, cunnilingus

I never thought I’d pay to peg a stranger.

I call myself “vanilla with sprinkles,” because missionary is underrated, threesomes are hot, and toys are the wave of the past, present, and future. I don’t know if I’m a top or a bottom. Most kink doesn’t do it for me.

With one exception. 

As far back as I can remember, I’ve wanted to peg a man.

I’ve wondered what it would be like to don a strap-on and go to town. To feel the new weight between my legs as I swagger toward the mythical him, both of us naked and open, ordering him to turn over. I imagine reaching his most intimate place, hearing his deep grunts as he jacks himself off, then turning his head to mine to kiss me long and hard as I penetrate. 

I want the sensation. The power. The rush that comes with stepping so far outside my comfort zone it’s a little scary but even more exciting. I want the confidence to know I can make it happen.

The thing about pegging, though? Wanting it’s one thing. Making it happen is another.

It’s not just that even the most supposedly evolved boyfriend or one-night stand freaks the fuck out when I offer so much as a pinkie in his asshole. And the kinky men aren’t any better—since they inevitably want something specific in return, something I’m never comfortable giving. 

Online? Forget that too. My app-loving pals do just fine, meeting everyone from flings to eventual spouses. But as a Dateline devotee, I suspect if anyone is going to be murdered during an IRL encounter, it’s me.

 So here I am, edging toward my thirty-fifth birthday unfulfilled, reaching a breaking point.

That’s when I hear about him from Cici, my sluttiest friend and the first woman to eat my pussy.

“He’s also bi,” she tells me. “Up for anything and worth every penny.” 

The catch: he’s strictly word of mouth.