I had met this girl on Tinder. She had a quirky profile and was clearly into being silly and not taking life too seriously. We chatted for about a week before finally being able to schedule a meet up. We met at a bar nearby her place. She seemed cuter in person than in her photos. At least I always find them to be more attractive in person.
She was clearly a little nervous and it came out in her awkward conversation style. As we both sipped on some cheap beer we talked about comedy, movies, favourite quotes, stupid internet memes, and how to be confident. I told her about all the public speaking I had been doing lately. She asked about tips and advice. I gave her some and she seemed receptive. I could tell she was attracted to the “casual professional” nature of how I presented myself. We joked some more, had a couple more beers, and then decided to head out for a walk thinking the night would wrap up soon.
We walked around the mixed use neighbourhood. Passing business and houses along the way. We walked along a side street and came across an old high school. We walked up the deserted pathway to the front entrance. We sat down and chatted some more under the light of the entrance doors. I could tell she wanted to kiss me so I went for it.
We start quietly kissing out on the steps of the school. We are both in full jackets as it’s October and chilly. My hands find their way onto the bare skin of her back. Stinging her with my cold touch. She inhales quickly while still pressing into my face. This continues for a while. We are kissing and feeling each other up. I suggest we move as this kind of behaviour in front of a high school might draw some attention. We are still out in the open and clearly visible.
I suggest we go back to her place knowing it is pretty close by. She seems hesitant but eventually agrees. We walk the distance from the school to her house. We are both still a little makeout-drunk from our passionate liplock a few minutes earlier. We get to her place and head inside. She offers me a beer and we continue drinking and chatting.
After finishing my beer, I slide up to her again and put my arm around her waist. She is much smaller than me so she is easy for me to maneuver. I start kissing her again. We both naturally drift towards her bedroom. We lay on her bed and continue kissing. We are on our sides. Face to face.
I reach my now-warm hands up her shirt again. Feeling her smooth skin against my own roughness. I press her into me. Trying to absorb her while teasing her lips with mine. My hands find their way to her cute little butt. I squeeze and caress it over her jeans. I want more. I put my hand down the back of her pants and grab a handful of her round cheeks. My greedy hands are now exploring her pristine flesh. I can tell she is really enjoying my butt massage. It must have been a while since a man has grabbed her in such a way. I slip her pants off so she is now just in her panties.
I move my hand from behind her and position it to reach down the front of her panties. I shift her so she is now lying flat and I am leaning over her. My fingers find their new home. I can feel her wet velvety-soft opening. I tease her just a little. Slightly rubbing her clit before slowly pushing a solitary finger into her moist opening. She is moaning now, hungry for more. She wraps her hands around my neck while I start to rub her mound more quickly. She tells me how good I am at it. This fuels my lust so I add another finger to make it two. The noise she makes doubles and our heavy breathes synchronize. She stops me. Pausing the pleasure. She says she doesn’t want to have sex.
She tells me she just finishing her period and is not feeling it. I tell her I understand. We don’t have to. Not all the best things require full sex. I tell her “there are other things we can do”, with a naughty smirk. I then lick the two fingers on my right hand and put them down the back of her pants – touching her asshole. She makes a surprised sound and her face changes to a blank stare. She doesn’t stop me though. I start rubbing her little asshole with my wet fingers. “Do you like it?”, I ask. She says it feels nice. She’s never been played with like that before. I pull my hand away and soak my fingers with another coat of saliva.
My hand once again slips past her lacy underwear and finds a spot between her plump ass cheeks. She is totally relaxed. Even for someone new to ass play she is totally receptive. Maybe it was the beer, maybe the hot makeout session, maybe she had been waiting for this. An index finger slips inside her. She closes her eyes and enjoys the moment. I’m fingering her ass now. She is just as caught up as when her pussy was being massaged. I start going a little deeper. Slowly fucking her ass with my finger. I can tell she enjoys the in-and-out movement. She wants me to finger fuck her ass.
I soak my fingers again. I ask her if she likes it. She says “yes, yes it feels really good”. There is surprise and a bit of embarrassment in her voice. “I didn’t think it would feel this good”, she says in a sleepy tone. That is my queue to continue pleasing my new woman. I now try putting two fingers inside her. She accepts them eagerly. I’m fucking her ass with my fingers now. She is turned on her side with my hand around her penetrating her once-virgin ass.
The pace slows down and I let her catch her breath. I pull my hand away and I ask her how she feels. She said that was so hot. She is lost for words. She puts on some sweat pants and we head to the kitchen to refresh. We open more beer and start chatting more again. We are completely dancing around what just happened in the bedroom down the hall. I can tell she is a little shook. She is unable to think straight. At this point, I’m going nuts and I just can’t keep my hands off her any longer. She is leaning against the counter facing me. I start kissing her again. We are immediately on fire as if we never stopped. I tell her to turn around. She does. She starts breathing hard with her eyes half closed. I pull her pants down slightly. Revealing her ass perfectly packaged in her lacey panties. I pull them down slowly. She is shaking ever so slightly. She is standing there with her pants down, hands on the counter, and I’m pressed up against her.
I touch her pussy and it is entirely soaked. She loves this. I lick my fingers yet again and push them into her asshole. Instant pleasure. She moans as if they never left. She sticks her ass out so I can have my way with her hole. I ask her again, “is that good? do you like that?”. She whispers positively. She likes it. I’m so horny at this point. My dick is hard. Pressing up against my pants. I start to undo my belt and slide my boxers down. My rock-hard cock flings out.
She turns around to see me there with my pants undone, stroking my dick – ready to go. I want to fuck her ass. I need to. I want to push slowly into her. I want to watch my cock get swallowed up by her hungry asshole. Feel that skin against mine. Feel the pleasure between us. Feel the pop as my cock slides into her tight entrance. I want to feel my load spilling inside that virgin ass.
She reaches out and feels my dick in her hands. She says its nice. She likes it. She wants it but she is hesitant. She says not tonight. She wants to feel my dick inside her, she wants me to fuck her ass, but this being a first date – it is just too much too fast. I concede and put my cock back in my pants. Still horny, I let it be.
We chat a bit more and start another beer. My mind is elsewhere though. So is hers. I can tell. We are both not really interested in conversations. We are just drunk on sexual tension. It’s late so we decide it’s time to wrap up. I start to grab my things. She is just watching me get my stuff together. Looking at her and thinking about the things we had done just 20 minutes ago left me wanting more. I stopped packing my things. I’m not done yet.
She is leaning against the wall as I press myself into her and start another makeout. She was dying for it. We went from 0 to 100 again. I’m kissing her hard, exploring her with my hands. I reach my hands down her loose pants. That ass is a magnet. I can’t stop grabbing it.
I tell her I want to finger her more. She wants it too. I spin her around and pull her pants down again. Licking my fingers for the last time I press them into her waiting hole. Heaven – again. She is as vocal as I am rough this time. I have two fingers in her. Moving them in and out, up and down. Her breathing is loud. Her moans are loud. I’m fucking her ass with my fingers – all the while thinking about the future possibility of my cock pumping in and out of that tight ass. My palm slaps her cheek each time I push my fingers inside. It took all my strength to not just whip myself out and penetrate her right there.
I slow down and her breathing does too. I take my fingers out of her and her legs become weak. She is spent. She pulls her pants up and sighs. She then thanks me. She says “thank you, I didnt know I liked that”. I’m sort of shocked at this statement. She is thanking me for fingering her ass? I say she is welcome. I tell her I want to try anal with her and cum inside her ass next time. She agrees we need to make that happen.
Source: reddit.com/r/gonewildstories/comments/l7i7ep/mf_first_guy_to_play_with_her_that_way
Oof. This was so hot.