First time anal (on a first date!) [MF]

I had a sexually explorative summer in 2019, and this is the first in a series of stories I’m going to write up, not in chronological order. Let me know what you think!

I matched with Liam on Feeld, and we instantly were messaging non-stop about what we like, sexually and non-sexually. After a few days, we meet up at a park, getting to know each other while sitting on a blanket having a drink.

We live in a large North American city. I am a 28 F, 5’2 a bit muscular and a bit curvy, with an hour-glass body. Liam was my age but 6’5 (!!) and skinny. We immediately hit it off. After sitting next to each other on the blanket and chatting for a while, the sun sets, and our hands started wandering. Eventually he leans over and kisses me. I live about a 15-minute walk from the park, so we decide to go to my place. Once we stand up, I realize how tall he is. I can easily put my arm around him and touch his butt :)

At this point, I’m really turned on, and getting really wet (I get really wet). We finally make it to my studio apartment. We sit on my small couch and I put my legs over his. He slowly starts rubbing his hands up my legs while we continue to talk. He’s making me maintain a conversation about something unrelated to sex (I clearly can’t remember for a reason) while I am very distracted, hoping that his hands keep moving up my legs. We make out a bit, but he moves back to the teasing. I like the teasing, but I am getting desperate. “Please”, I beg.

He picks me up and moves me to my bed. Bends me over the bed and starts taking off my shorts. Teasing at my thong. I’m quivering in anticipation. Finally, he takes off my thong and fully gets to feel how wet I am. His excitement turns me on even more. I ask if I can undress him. It’s not fair that he’s fully dressed at this point. We take this moment to both strip naked, helping each other remove his clothes, and the remainder of my clothes. I tell him that it’s my turn, and he lays down on the bed. I kiss him, and then slowly move down his body, kissing parts of his chest, touching his body, and eventually reaching his hard cock. I start blowing him, taking him deep into my mouth. He has an aesthetically pleasing uncircumcised dick, that’s quite long but isn’t too thick. It’s a challenge to fully get it into my mouth, but I aim to please, and am willing to put some solid effort in. In and out, and lots of suction. He’s worried he’s going to cum, so he flips me over and starts going down on me.

I love the feeling of his mouth on me, and I like it even more when he slips one, and then a second finger inside me. Curling his fingers with a lot of pressure, I tell him to take his mouth off and really focus on his fingers for a second. One hand pounding my g-spot, and the other pushing on my stomach, and I cum hard and let out a scream. I know this is going to be a great night. We end up grabbing my Magic Wand, and he fingers me again while I hold the vibrator on my clit, and this time I squirt everywhere. He’s never been with a girl who squirts before and is suuuper into it. I’m glad I had put my waterproof blanket down ;)

Now he wants to fuck me. While he’s standing beside my bed opening a condom wrapper, I’m lying down and letting him thrust his cock into my mouth, to get super hard before he fucks me. Condom on, and he slowly enters me while standing, me lying by the edge of the bed now. This feels good. We line up nicely. He picks up the pace, fucking me harder, angling his dick at my g-spot, and reaches over to put a hand on my neck. I’m so turned on and everything feels good. I tell him I’m going to cum. “Cum for me” is all it takes to push me over the edge, and he keeps fucking me while I’m just trying to exist through this orgasm. It’s hard to remember all of the details, but I know that at some point we flipped over to doggy and I couldn’t stop cumming, my pussy clenching on his dick, and even squirting sometimes, as he hit the right spot. Trying to just exist can be a challenge during that, and I love it. He kept thrusting, and as I was telling him I was going to cum again, he thrust hard into me, and cums loudly himself.

After some cuddling, things start getting heated again as his hands moved to my still wet pussy, slowly working their way in. He grabbed my Magic Wand and put it on my clit, and fingered me to another orgasm. Once I’ve started, it’s easy for me to keep cumming. As two sex-positive people open to exploring, we had talked about a lot of sexual preferences and things we want to try. I knew he really liked butts. I had very little butt experience: a finger a few times, and a small butt plug a few times. After texting earlier in the week, I got inspired and picked up a new stainless-steel butt plug ([a Njoy medium plug](https://www.njoytoys.com/product/pure-plug/)), but hadn’t used it yet. This seemed like a perfect opportunity to explore more. He helped me put the plug in with some lube, telling me how cute my asshole was. It went in no problem, and felt good. He slipped his fingers back into my pussy and it felt amazing. Plug, fingers, and then I grabbed a vibrator for my clit, and I was quickly cumming hard, and gushing. Fuck, that was hot. I came so hard that I needed to lay down and catch my breath for a moment.

I kept the plug in, and started using the vibrator on him, below his balls. Like a lot of guys, he had never previously used a vibrator on himself, only on his partners. With the Magic Wand on his taint, I started blowing him, and eventually switched to finishing off with my hands, getting him to cum all over my tits (sized 34F). He wanted to get me off one more time, and so we used my [Njoy pure wand](https://www.njoytoys.com/product/purewand/), a stainless-steel curved dildo that is meant to pound at your g-spot with a lot of weight to it. I love it. It makes me squirt a lot too.

Eventually, we are lying in bed exhausted, after he had cum twice, and I lost count of how many times I came. He likes to do this thing while spooning, where he pushes his soft cock at my asshole (which no longer has a plug in it). At first, I tell him to go ahead because it seems like something that won’t bother me, and I’m down for whatever feels good for someone as long as I don’t actively dislike it. But after a while, it starts feeling really good to me. It starts feeling like a tease to me. At this point, we thought it was the end of our hookup, and we were just cuddling. Quietly, I tell him how good this feels, and that I want him to actually put it in. “Reall?!”, he says with enthusiasm, making sure he’s hearing things right, and then grabs some lube. I relax, and he slowly pushes in. He’s done this many times, and he’s told me that he thinks his long and narrower dick works well for anal. We’re spooning, and I’m holding my magic wand on my clit as a sort of comfort, and I can feel that he’s fully inside me. That wasn’t too bad!

He starts slowly thrusting. I’m trying to stay relaxed, and feel the pleasure in it. And I do. It feels good, and the vibrations are moving throughout my entire pelvis. Every so often I ask him to stop thrusting, just for a second. Not because of pain, more because I’m getting used to the feeling. Eventually, I tell him he can pick up the pace. Now he’s really fucking me! It feels good, and it feels like a lot, and I’m experiencing a lot of sensation between being fucked in the ass and the vibrations on my clit. He’s super into it, telling me that I’m being a “good girl”, and how good my ass feels. He starts breathing louder, and then suddenly I feel his warm cum spurting inside my ass. Damn. I can feel his cock twitching, as the cum pumps into my ass and it feels amazing. We got him to cum a third time, which is something he says rarely happens.

We lie there a bit longer, and eventually he leaves. We hung out a few more times after this, but nothing further came from it.

Note: I regret not using a condom for the anal, it was the responsible thing to do. I had just gotten tested (and he knew this), and he had recently gotten out of a monogamous relationship. Still, it was dumb and we should have grabbed a condom.

Source: reddit.com/r/gonewildstories/comments/f1hmp8/first_time_anal_on_a_first_date_mf

7 comments

  1. I can’t believe he didn’t want to see you again? That was a hot night!! Was it a personality issue between you two? Hope this doesn’t make me sound like a “nice guy” but I would have at least wanted to cook you breakfast the next morning. Happy Hunting on Feeld

  2. That’s too bad. I personally wouldn’t have let you go. You seem to be too good of a catch. You said “muscular look” to describe yourself. I also workout alot to. I imagine we would have plenty to talk about. Best of luck to you. Hopefully I’ll read another great story from you.

  3. That was hot and I’m glad you both had an incredible time. It’s always refreshing having sex with someone whose similar to you. I definitely need to try using my plug and my wand at the same time while my Dom is inside of me because that was hot!!

  4. Reads like a commercial for njoy toys… I get that you used this, but you’re pretty obviously plugging that brand. (pun intended)

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