Tl;dr: Prepared all day with a plug, it hurt the first couple strokes but after that it felt surprisingly good. 7/10, would do again.

Now to the nitty gritty.

To preface this: this does not declare open season on my asshole. Don't pm asking to be next.

Yesterday was my very first time having anal sex. My lover has been wanting it for a long time, and like I always say, we're in the business of wish fulfillment.

So I knew he wanted to try it that night, so I prepared all day by wearing and playing with my stainless steel butt plug. By the time I got to his place I was nervous, but determined.

He's so much bigger than me. It shouldn't thrill me so much, but it does.

We start kissing, and rush to tear our clothes off so we can get to skin. He rubs his hands over me, rubs me between my legs, spreads my ass and rubs his fingers over my asshole and groans "Fuck, baby. You're so fucking sexy."

I blush and say aww, because somehow that's more embarrassing than everything else I let him do to me apparently, haha.

First things first, he shoved my legs up high and eats me out. As usual, it's life changing. All I can do is rub his head and moan and say his name over and over. He slides his fingers into me and licks me like it's his job, and slides his tongue back to my ass just when I don't expect. I whisper his name and say "no", but only because it's seems like the right thing to do. He ignores me, as well he should.

He leans up and kisses me, and then finally he's inside me. I start moving desperately against him, shifting my hips so I can feel him against my gspot. He sucks at my mouth and sticks his tongue in my ears while I gasp and moan. He's fucking the hell out of me, and my head is blank. My body is shaking, and my insides are clutching him. I only ever feel this wild with him, only with him do I feel like I'm constantly standing on the edge of an orgasm that will knock me off my feet.

Once he's close he pushes away and his fingers are inside me again and my moaning turns to gasping and sobbing and begging. His hands are my favorite part of him.

We 69, with him sticking his to guess in my ass and rubbing me internally, making me sob against his leg. I get on all fours and blow him while he's on my knees, rocking myself back and forth on to his cock. He rubs his hands softly in my hair and groans, "Fuck baby. That tongue is so good."

Eventually, it's time for the big show. He asks one last time, "can I put a condom on?" His version of, "is this okay?"

I say yes and say, "Hands first!"

I rub lube over my asshole and get on all fours, doggy style.

He says-"Wait, lay on your back." And then a second later he grins at me and says, "No get on your hands and knees. Doggy style." I laugh at him and get on my hands and knees, and then drop my shoulders to the bed so I can reach under with one hand and rub my clit.

He rubs his fingertip over my damp entrance and then, in. He never does anything halfway and slides it ALL the way in, and then out, and then in again while I gasp and my heart pounds with nervousness and sensation. I've had his finger in my ass before, but I'm still shocked by the intrusion. I hear him groan my name as he fucks my asshole with his finger. Hearing the lust in his voice sends shivers down my spine.

His finger disappears and I feel the head of his dick, wrapped in a condom, press against me. I move into him a little, bear down with my muscles. I feel pressure and then he pops in! Maybe an inch slides into me and I go "Oh my god, well ow, go slow!"

"I am going slow," he says and pushes another inch into me. Well shit! Ow! I squeal a bit. I feel myself pulling away a little bit, but his hands are tight on my hips and I can't go far. I feel him push in deeper and I'm shaking and cursing.

I'm trying to remember what I know about anal- to relax, and bear down when he pushes forward.

"I'm gonna pull out okay?" He says to me. And I say "Good idea!"

He slides mostly out of me and I'm about to just give up on this whole anal thing.

He slides back in, and ow! It feels huge and deep- very deep!

And then he reaches down. My feet had instinctually been pressed against his thighs, trying to hold him back a little. He knocks my feet out of the way and seats himself that extra half an inch, and he's fully inside me, and something unexpected happens to me.

I moan. That last push did not hurt. I start moving my forgotten fingers, rubbing my soaking wet pussy. He pulls out of again- and huh, no that didn't really hurt. And then he slides back in and oh. Oh that doesn't hurt either. And then again and I reach my other hand down, slide my fingers into myself, and I can feel his cock in my ass through my walls.

And oh god bless this man, this feels good. I find myself groaning, "A little faster."

And he starts moving faster, and in a minute he's pounding into me like he would if he was in my pussy.

And holy shit. This is good. It's different, and he feels huge in a very small hole.

But there's no pain.

And I can hear him groaning loudly behind me, saying my name, in a way that makes my toes curl. And each time he slides all the way in oh good does it feel good. I finger fuck myself madly, feeling his cock through my ass and rubbing my clit.

I'm moaning so loud, my mouth wide open, bringing down the house.

And finally I gasp and my pussy clenches and my body shudders- a small orgasm rubs through me, tensing all my muscles. I hear his swear, say my name, and then the hard quick thrusts as he cums in my ass.

A moment later he slides out, and I collapse and curl my legs up towards my chest.

Suddenly self conscious I look around for anything, ahem, "messy".

Shockingly, nothing to be worried about, nothing gross going on.

I laugh a little and say "oh my God"

And he says, "Holy fucking shit, Sam. Oh my god. You okay?"

And I laugh and cover my face and say "Yeah that felt... That felt good actually. I'm kind of embarrassed somehow."

I quickly rush to the bathroom to clean up. I was nervous, but to my shock there's no blood, no pain, no even soreness to be had. I wash up and go back to get dressed.

And that was that. My first anal sex ever- and it hurt, but once it stopped hurting it felt good and very bad in the best way. I'm not saying I'm giving him my ass again next time I see him... But there's always next week ;)