This is my first time writing out a story like this, but this was so hot that I still think about it a year later. I am not a succinct writer so apologies for the length.
I’m going to put **** before the sex stuff starts but here’s the buildup:
So right before everything shut down in 2020, I matched with this guy on a dating app. I’m going to call him Charlie. Charlie is a couple years older than I am (21F) and before the pandemic used to split his time working in my city and in his, where he owns a condo.
Charlie is hot. He takes care of himself, eats healthy, works out 6 days a week, lifts, and regularly grows his hair out to donate. He has tattoos all over his torso and a tongue piercing. He’s about 6’4″ so he towers over my 5’2″.
I on the otherhand, am short and curvy. I don’t think I’m the hottest person out there but I have a decently full ass and am a 34DDD/F or G depending on the bra. My measurements are roughly 38-31-43.
We started talking in Feb 2020 and even though lockdowns meaning there was no way we were going to meet anytime soon, he quickly became a good friend of mine. Fast forward to August 2021, we’ve been talking this whole time, nothing too sexual or risque but we’ve talked about my still being a virgin, kinks we shared, and us hooking up in the future.
I struggled with my self worth for a long time so at 20, I had actively made the decision not to have sex until I was sure I was doing it for myself, and not to appease my partner or anything like that. A while before going to see Charlie, I slept with my ex. I chose my ex because I felt safe with him, and he wasn’t too large or long (not that he was small, he was perfectly average and exactly what I wanted as an introduction).
With my first time gone, I felt more comfortable, ready, and excited to have sex with Charlie.
We planned my trip out to him about 2 weeks in advance, I was coming early Tuesday afternoon and leaving late Thursday afternoon. We had already talked about potentially having sex if the vibes were right, which after over a year of snaps, texts, phone calls, video calls, was almost certain but you never know.
This is when the teasing started. He would send me photos or videos of him just out of the shower with nothing but a towel wrapped very low on his hips, sometimes dancing to some silly song or singing to one of his dogs in his arms. So obviously I would send flirty responses with low cut tops, booty shorts and towel photos. These got more and more saucy as the day got closer. Both of us feigning innocence whenever we would call the other out for being a tease.
The day comes, I’ve packed my bag with only clothing that showed off my assets or left little to the imagination.
I make the trip out, leaving at 10am and get to the other side of the ferry around 2pm where he’s picking me up. I was already aware that he’s over a foot taller than me, but he was also muscular, and this being our first time meeting in person made me realise how small I felt next to him. I’m not a skinny girl, so this is a rare feeling for me.
We drive to his place and spend a greater portion of the day hanging out with his pets and having a fun time together.
Later in the evening, he wants to take me to a cool view point so we make the drive out. By the time we get there, the sun is just finishing setting over the city and it’s a gorgeous view over a hill of a river and the lights. There’s a concrete wall that lines the edge of the steep drop, and we sit on that for a while talking. We start walking up and down the wall, at a point I’m standing on the post so we’re eye to eye and we start making out. We decide to head home.
****
We finally get back to his place and the energy between us is palpable. He unlocks the door and holds it open for me to walk through, and as I pass his hand, his fingers graze the strip of exposed skin between my crop top and leggings. And this was the tipping point. He pulls me in and we start making out again.
We’re on the couch, I’m straddling him, grinding on his boner and our hands are wandering all over. He seems a bit hesitant with escalating anything even though I’m very much giving him every signal I can so we pause and check in.
I ask if he’s not interested because we can definitely stop.
“No, I just don’t want to do anything you’re not okay with”
“Trust me, I am enthusiastically enjoying everything right now…” I grind my hips down on him a little and then it hits me that he had mentioned not wanting to take my virginity just because I was there. So I ask “Did I tell you I had sex?”
“Oh, you didn’t tell me that. How was it?”
“It was good, I’m apparently a little tight and just need a little to warm up to the size. I’m excited to try more things and you know… Maybe get railed sometime”
I start nervously tracing one of his tattoos during this and I see it click with him. He sits up so his chest his touching mine and kisses me again, grabbing my ass and we’re back. He gets me to stand up and we walk into his bedroom. I’m getting really turned on and my submissive side is coming out so instead of making a move, I just look up at him.
“What do you want me to do for you?” I ask innocently.
“I think it’s time to get on your knees and show me how much you like sucking dick”
I instantly drop to the ground and look up at him. He pulls his pants down and I don’t think twice before I’m giving him the best head I can. I’m going deep, letting his head hit the back of my throat and using one hand on the rest of his length and the other to play with his balls.
After a little bit he pulls me off and pins me against the door. He groans something in my ear but I can’t think of anything past his hands on my tit and clit and his boner pressing into my back. He’s kissing and biting my neck, driving me insane. After a bit of him turning me into putty, I ask him to just fuck me already.
My clothes are off in half a second and he’s tossing me onto his bed. I turn over and assume my favourite position, my face in the pillows and ass in the air, hands crossed behind my back.
“Please. Fuck. Me.”
He quickly lubes both of us up and starts pushing into me.
“Fucking shit” he groans while only halfway in “you’re so fucking tight”
After giving me some time to adjust, he starts with slow but deep strokes.
“So. Fucking. Tight” he’s growling this between every stroke into me meanwhile I can’t bring myself to do anything but moan.
I’m absolutely trembling now, at some point my legs gave out so he’s fucking me prone, straddling my ass and I’m trying my best to twerk back onto him.
He stops for a second, halfway into me and I look back over my shoulder to see what’s up.
“Twerk for me”
So I do. I start shaking my ass back on him and moaning even louder when he reaches around to rub my clit.
“Spank me.” I somehow manage to get that out and he doesn’t waste a second before giving me a light smack. “No. Harder. Fucking spank me!”
He pulls my ass up so I’m back on my knees and starts properly spanking me while I’m still pushing back onto him. He keeps going until my ass is hella sore in the best way.
After a little while, he gets out of me, rolls me over and lays next to me. We’re both breathing hard and he pulls me closer to him, lightly rubbing my ass and kissing me. We just make out for a while just cuddling and caressing each other.
After a while, he goes back in, and if you’ve never tried to fuck sideways, it’s nice in theory but just okay in practice.
We end up back in doggy, but this time with a pile of pillows under my hips for comfort. I’m the most turned on I think I’ve ever been, I’m begging for more of him in me and for him to just fuck me however he wants. This is when he starts just ramming me. Hard, fast, deep strokes. He’s hitting my cervix, which is not something I usually like but I’m so fucking horny right now that it feels amazing.
He was the first person to ever hit that spot, somewhere I didn’t even know existed. I think that anyone who’s ever been fucked that deep and enjoyed it knows exactly what I mean. It’s heaven when you’re filled to the brim.
Neither of us came that night, we fucked until we physically needed to stop, cuddled, showered then fucked again before going to bed.
The next couple days were filled with us having sex 2-4 times a day and ended with me missing the ferry I meant to take so we just went for another round and I caught the next one.
We’re still friends today, with the possibility of us hooking up if the cards ever align but currently he has a girlfriend and a schedule far too busy for a visit.
Source: reddit.com/r/gonewildstories/comments/v92fwq/fm_i_travelled_45_hours_each_way_to_get_railed
Hot af! Good for you to let yourself loose like that.