Plain Jane – A 750 Word Story

This story was written for the 2025 Literotica 750 Word Challenge. Below this line are exactly 750 words.

My name is Jane. I’m 5’11,” 150 pounds, big glasses, shapeless clothes. If not for my height, no one would notice me.

I discovered online dating a couple months ago. I answered all the compatibility questions in detail, especially the sex ones, but every guy I’ve met has only cared about getting his dick wet. I’ve been through four of them so far, and none of them did anything for me. I’ve become dispassionate about cutting them loose.

What I secretly want is to fuck a man in the ass. I’ve already bought a strap-on in case I ever meet Mr. Right. Nylon harness, realistic dildo. Sometimes, I’ll get naked and wear it in front of the mirror. It feels good.

It’s not a dominance thing, at least, I don’t think it is. Conventional PIV sex isn’t dominance, right? I read somewhere that the difference between fantasy and kink is that kink is similar to sexual orientation. I don’t know if that’s right or not. If it is, fındıkzade escort this is my kink. My romantic and sexual identity.

Today, I’m on a first date, meeting my latest online suitor for coffee. (Fifth time’s the charm.) He’s nice. Short, glasses, cute in a nerdish way. It’s almost disappointing when he hugs me goodbye at the end without asking me if I want my place or his.

Our second date is a tasting at a local winery. We both joke about how we don’t know anything about wine except that it gets us drunk, which I’m pretty sure is annoying to everybody except us. I’m warming up to him.

We end up at my apartment, sitting on my bed. He asks permission(!) to kiss me. After that, it’s all roaming hands and clothes coming undone. His eyes light up when he sees the spectacular tits that I keep hidden under my giant sweaters. In some ways, all men are the same.

We’re both naked. He’s quite hairy, and chubbier than he looks when he’s wearing clothes. (I’m pretty aksaray escort soft around the middle myself.) I’m telling myself, this is it. Tell him or don’t tell him, but stop wasting time.

I’m about to open my mouth when he says, “I feel like I can tell you anything.”

If you’ve ever been the unspectacular girl who men tend to think of as “unthreatening,” this probably gets your hackles up.

Then he tells me there’s something he’s always wanted to try. What he says next shakes me. Without a word, I go to the drawer where I keep all my sex stuff and hold up the strap-on for him to see. It’s his turn to be shook.

Shyly, he bends over while I tighten the straps around my narrow hips. I pull on a black nitrile glove and lube the fingers. I lay a shining fingertip on his asshole, feeling cords of powerful muscle, and he tells me it feels good. After a bit of massage, he doesn’t feel as tense anymore. I push, and my middle finger goes right in up to the hilt.

I’ve eyüp escort read every article about this under the sun, but I’m not prepared for how warm and buttery he feels inside. I give an experimental wriggle. He all but coos with pleasure.

I try a second finger, then a third, slowly warming him up. He’s pliant, eager.

I make sure he’s watching as I lube the dildo. I think he gets the unspoken message: in a few seconds, this will be inside you.

I kneel behind him and park my silicone dickhead against his hairy pucker. I tell him to squeeze down, hard, then relax. He exhales slowly.

He swallows me easily. When I’m in up to the O ring, we check in with each other, making sure we’re okay. Then I start thrusting.

Soon, I’m sweating, and already sore. My body isn’t used to this. Still, I can’t describe how good it feels. It’s like I’d been having sex with the volume turned down. His cries get high and tremulous. They stir a fire in me.

We roll him onto his back. I fuck him shallowly while he jerks off, until he decorates himself with long, thick ropes of semen. Carefully, I withdraw. The smell of lube and anal funk is intoxicating.

He holds me limply while I reach under my silicone balls and make broad circles on my vulva. I come quickly; my orgasm is explosive. I’m shaking in his arms. He and I will share this moment forever.