The first time [anal] [F32, M37]

I don’t recall when or how it was first brought up. The messages between us in those early days made it quite clear that nothing was off the table. When it came to anal sex, it was something we both admitted we were keen to try, but I didn’t know that was in today’s plans when I left my house to meet you.

(Fully formatted story can be found on my website [here](https://sextoyreviews.uk/the-first-time/) but I wanted to share this one as I really enjoyed writing it…).

I arrive at the hotel.
You’re already there; you’ve checked in, and you tell me to come directly to your room where you’re waiting for me. To prove it, you’ve send me a picture of your erect cock. So perfect, and all for me. A shiver of lust goes down my spine.

As you open the door, I can feel my heart thumping, caused by a mixture of nerves and arousal. Our meetings have always left me satisfied, but wanting more of you.

You don’t even kiss me hello, but instead lead me straight to the bed and sit down. You have a plan.

Take off your clothes, you command, and I don’t hesitate; I spent hours choosing the right dress and lingerie for the occasion and it’s all discarded on the floor in seconds.

Lie across my lap. On your front. Again, I do as I’m told. Bum in the air, head rested on the bed, everything on display for your approval.

You start massaging my buttocks; quite roughly, just how I like it. You slap one and I gasp. Shhh you say, and slap the other cheek harder.

I hear the click of a bottle cap being opened, and suddenly, cold liquid being spread over my stinging behind. You rub it in until the whole area is slippery with massaging lube.

Smack. I shudder with pain and excitement.
More lube is added, this time concentrated on my arsehole. Carefully, you slide a finger into me, and make me gasp again. With your other hand, you caress my bottom while you finger it. You add another lubed-up finger and make my nerve endings tingle with anticipation. My mind is racing with thoughts of what will come next.

Play with your clit you say, and I oblige. I realise I’m very, very wet. I feel so horny I could probably cum right there, but I know you’ll be angry if I do and my butt is already feeling sore; I don’t want more smacks.

You remove your fingers.

Hold still.

I feel a solid object – a butt plug – being pressed against me and slipped inside.
I’m relaxed and turned on, but it feels bigger than I’m used to so I have to breathe through it. We need to make sure I can take more, so you can use me in all of my holes. We’ve both admitted that is a fantasy we share.

You tell me to keep rubbing my clit, and slide the fingers on your other hand inside of me, stroking my g-spot. The feeling of being full in both holes is delicious. I want more though; I want your cock.

Not yet, you say. Take me in your mouth first.

Butt plug still firmly in place, I move from your lap to between your legs, unzip your trousers and pull down your pants to reveal your throbbing cock. I can’t wait, and immediately take the whole length into my mouth, gagging as I do.

Good girl.

I use my hands to stroke you as I concentrate on the head, swirling my tongue around. It drives me wild when I make you cum with my mouth, but it’s too soon; you have other things planned.

Stand up, and sit on my cock, you demand.
I climb up on to the bed, kneeling either side of you with my arm around your neck, and slowly lower myself down on to you. You put your mouth first to my mouth and kiss me deeply, and then to my nipples. You nibble on them; gently and then not so gently. Moving my hips, I start off slowly and get faster. As I rock, your whole eight inches buried deep inside me, the feelings overwhelm me and I reach a shuddering climax.

I didn’t tell you to cum, you say. You’ve disappointed me. I’m going to have to punish you.

I’m sorry, I reply, I didn’t mean to, but you aren’t accepting of my apology. You tell me to get off of you, and then to remove the butt plug. I worry slightly that you’re being serious, and our meeting is over, but I know it can’t be.

I watch as you grab the lube, and apply it liberally to your cock.

I now understand what the punishment will be.
You tell me to lie on my side, you laying behind me with your erection pressing into my back. I’m told to use the magic wand on my clit, but only on low. I’m not to cum again until you’ve taught me a lesson.

My butthole, plug removed, is relaxed and gaping slightly and ready for you. Gently, you push yourself into me. It feels a lot. My anal experience isn’t extensive, I’ve never taken anything nearly as big before. You know this, and you go slowly; inch by inch, allowing me to push back against you until your whole cock is inside of me.

With the magic wand turned up slightly, the combination of vibrations and anal stimulation feels so intense I can barely control myself. Soon I’m bucking against you, taking you all in my arse, wanting you to pound me and make me orgasm. I never knew it could be like this.

You grab my tits, hard and desperately. You put your other hand around my throat and tell me not to cum. I’m not to cum until you do. That’s my punishment.

Please, I beg as you fuck me, Please let me cum. Please.
OK… CUM, you say, CUM as I fuck your arse.

I turn the wand between my legs up to full intensity and allow the sensations to overwhelm me. Small explosions course through me, the most intense of my life. I almost scream. Oh, fuck!

You don’t stop. Next time, you’re going to take something in your pussy too, you tell me as you slide your cock in and out of my tight areshole. I’m going to fill you up completely. You’re my little slut, and your holes belong to me.

I cum again; this time so hard that I need to take a minute. I experience wave after wave of intense pleasure as my body tenses and relaxes over and over; it’s unlike anything I’ve known before. Fuck, I love you, I whimper.

You thrust, hard, and grunt, losing yourself in the moment with me. You call out as you reach your own orgasm and cum inside me, in my arse, for the first time.

Source: reddit.com/r/Erotica/comments/zouim8/the_first_time_anal_f32_m37