Six stories about anal sex

1. Shaun is model-pretty, he mostly just fucks older married women, but he says I’m fun.
It’s Homecoming night, my Budweiser soaked blue gown is flipped up over my waist. Heavily scented with pot and Drakkar Noir, he leans in and whispers “I want to be the first to fuck your ass.” Shaun promises to go slow. If I like it, he says, then I’ll want to do it again.

He scoops a translucent fingerful of Vaseline from a little tub, then rubs the outside of my asshole in little circles.  Slowly, he slides one finger, then two, gliding them in and out for a long time. I almost fall asleep from the rhythm. I lie on my stomach, he nestles in close, guides his dick in. It doesn’t hurt a bit.

2. Lee is hiding something, I find out exactly what in his toolbox one day. When he comes home from work, I throw the box of condoms at him. We’re young and violent. I’m seven months pregnant and freshly twenty-one years old. He says he bought them so he could fuck me in the ass. I call him a liar, stab the little blue packets through with a kitchen knife.

Weeks later, I find another box in the crawl space. Bitterly, I ask him if he was still planning on ass fucking me. Shoving me face first onto the water bed, Lee rolls a condom on. He holds me down and forces his dick in my ass. The condom isn’t lubricated. Biting my lip, I refuse to make a noise. He frees one of my hands, and I hold the heaviness in my stomach. I cry the next time I shit.

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It’s still the early dial-up internet days.

Everyone has already figured out that everyone else lies. Except me. I lurk in chat rooms. No one believes my personal ad, they think I’m kidding: 5 ft 9,  128 lbs, red hair. I swear I’m for real. Another private message window pops up, this one lives an hour from me.  He’s articulate, literate, and witty.  He knows things about sex that I’ve never even heard of. I’m smitten.

I chain smoke in the dark night after night while the scene unfolds line after line. Since he won’t tell me his age, I assume he’s years older. He won’t talk on the phone or send me a picture. Maybe he’s married or really old, like forty. Frustrated and angry, I type: “What are you, 15 or something??!” The blinking cursor hangs an eternity…

I can’t forgive him, I’m heartsick. I blow off a real date with a schoolteacher to meet him at the mall. His mom chaperones. She sits by the fountain and watches us hug. She tells him I ooze sex.

Now it’s thirteen years later. I email him to tell him I might start writing some of this crazy shit down , should I tell this story?  “Nah,” he writes back. “We never even had sex.”

This is my first time with a girl.

Stephanie’s pussy reeks. I don’t know what to do. I can’t keep this up much longer.  I’m licking her through wads of black pubic hair with the very tip of my tongue, trying to stay back. Breathing through my mouth only makes it taste stronger. It’s hard trying to be suave and butch when I’m trying not to gag.

Stephanie tries to finger me, but she’s got long sharp hot pink nails and wears lots of rings. She keeps gouging me. Every time we try to kiss we end up giggling. I’m covered in a nervous cold sweat. I’ve seen porn, this isn’t how it goes. Thankfully her baby wakes and won’t stop crying.

This is literally a fucking disaster.

For one entire year I decide to fuck like a man.

I fuck who I want, I don’t call back, and I tell them they can’t stay over. It takes me two months to convince Eric that sex is all I really want.  He’s fifteen years older, addicted to pills and owns an entire building downtown. I come over, fuck him, and leave to prove my point.

It always starts the same. He undresses me, orders me to the side of the bed and methodically eats me out, pussy and ass, for an hour. He doesn’t take his clothes off. I lay there exposed, not sure why I’m so excited. I don’t know yet about doms and subs, but this is definitely it. He yanks me to my knees and crashes into me from behind. I ask to stop for a cigarette, he smacks my ass hard and roars “You wanted to fuck, now fuck.” The pills make Eric paranoid.

He has guns hidden in every room of the house. More than anything I want him to load one and hold it to the back of my head when he fucks me. I never ask because I know he would do it.

It’s hour six

…of my thirteen hour drive to Kansas City. It’s really a booty call, but I convince myself it’s love. I’ve known Alan since the first week of junior high. In high school he was always my second choice. I was in love with his best friend. Now I am obsessed and desperate. Alan’s learned to dangle the proverbial carrot, I fall for it every time.

I’ve driven to Fort Wayne, Terre Haute and Grand Rapids, to budget motels that advertise kitchenettes and weekly rentals. I pull in as the sun sets. We spend a weekend in a decrepit camper, stoned on pot and muscle relaxers. He’s beginning a bad alcohol habit, he sweats beer. The camper is cramped and smoky. A thunderstorm shakes the earth like a herd of running dinosaurs. He fucks me and I make love to him.

Alan will never tell me that he loves me until it’s too late. After this weekend he stops calling and moves away. I won’t see him again for ten years.

New Year

This is the fourth New Year’s Eve in a row that I fuck Tony.

We fuck only on New Year’s, our little secret tradition. Leaving the noise of the party behind, we slip off to a makeshift bathroom in someone’s basement. I balance on the toilet seat that rests on the sloshing bucket, my little red lycra dress snags on the dirt wall.

Tony’s leg tangles in the old brown shower curtain that serves as a door, it moves back and forth revealing us with every thrust. The room smells like warm piss and we smell like cheap beer. I wrap my legs around him, knocking down the sign that says “Don’t shit in the bucket, go upstairs.”