#EroticJournalChallenge First Time…

When was the first time you realized you were ______? OR When was the first time you realized you liked or enjoyed ______?

Richard: Jayden and I thought it would be fun to do the same kink for this one, and we decided to do anal/painal.

Jayden: When I was young (too young to be having sex), I thought I liked anal. I don’t know if it was just that particular partner or if it’s too long ago and so it’s fuzzy, but I did remember liking it. There was definitely a part of me that was into it because it felt “cool” or “sexy” to be into anal. A lot of girls weren’t, from my limited knowledge of the world, and so it made me “better” to be into it.

As an adult, I realize that a lot of that is bull shit. Liking anal doesn’t make you better or worse than anyone else, it’s just a matter of matching up with someone who has the same kinks or interests as you. There’s also a lot to be said for different partners bringing things out in you.

For years and years in my previous relationship, I only did anal with one partner (that was one of the rules we had) and it was fine. About 95% of the time, I didn’t look forward to it, but I was willing to do it because he liked it. I certainly didn’t protest about it.

And then I met Richard. He wanted to do anal, and I wasn’t so sure, but I wanted to please him (hey, that’s my kink!), so I said yes. I was worried because my understanding from the discussions we’d had, he can *last* in the bedroom. I was afraid I’d be sore and need to stop. But Richard has always been a very accommodating partner, and I had a safe word, so… why not?

I’d be afraid of spoiling the story, but the prompt was “when was the first time you realized you liked anal,” so… I’ve already spoiled the ending. So, here you go, a fictionalized retelling of the first time Richard and I had anal sex and I realized that it was fucking awesome.


We had already had sex today, and I was tired. And I was supposed to be busy doing things, but I can’t focus. All I can think about is being close to Richard, touching him, feeling his body against mine.

I’m sitting in an armchair that is definitely not big enough for two, but here he comes anyway. He leans down and kisses me. I moan softly against his mouth. He’s practically climbing into my lap.

“This is a bad idea,” he says, but my legs are already spread for him. I don’t care. “No,” he says, stopping me, “Get up and go over to the couch.” The couch with the ottoman in front of it made a much better space.

I go over, pulling my dress off and dropping it on the floor. I lay on my back, my legs spread for him, and I’m dripping wet. I’m always dripping wet for him.

“I want your ass,” he growls.

I’m scared. I know that he had wanted my ass, and I had even been trying to prepare for it, but I didn’t love anal as a rule, so the prospect of his big cock in my ass was terrifying. “Take it,” I groan. I want it. As scared as I am, I want it.

“Turn over.”

I get up on my knees in the right position, thrusting my ass into the air. He slips inside my pussy once, twice, three times, and then goes for my ass, but I’m so tight. He pushes his finger inside me.

“Oh my god, you’re so tight.”

All I can do is groan. I am so bad at talking during sex.

“Are you ready?” he asks.

“Yes,” I grunt. My face is buried deep in the pillows on the couch.

He presses his cock into my hole, and it burns as it stretches me out, but he gets it in. Oh god, he’s inside me. It hurts, but it feels incredible. He doesn’t wait. There’s no gentle thrust to get me used to how big he is. He’s using me. And it’s fucking hot. He thrusts in and out, filling me each time. It’s incredible. I’ve never had sex like this before. Before long, it feels good. Amazing, even. I really thought it would just hurt more the longer it went on, but it doesn’t. It feels great.

——————

And now we can’t go more than a week without anal before I get very grouchy and pouty. Apparently, I just needed the right partner.


Tomorrow and Sunday, we’ll post Richard’s written a fictionish account of some fun painal from his experience. Don’t miss it!

One thought on “#EroticJournalChallenge First Time…

  1. My my! What a read. Anal is not something we’ve done before but I know Matt wants to. I do have a hard time relaxing though so it’s probably unlikely to happen.

    Liked by 1 person

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