This story happened while I was in High School and for the sake of the rules we’ll say I was 18 at the time. Given that quite a bit of time has passed the dialog has been mostly improvised from memory but the meat of the story is exactly how it happened.
So there we are in the dead of night driving through the type of place where they play banjo music, refer to black folks as ‘Boy’ still and generally just don’t like their daughters dating people with as much pigment in their skin as I do. Why you might ask? Because I had met another girl off the internet who was very much interested in fucking, but even I was hesitant about going to a place like this by myself.
“Dude, sure you want to do this” My cousin Jay said looking at the house/large trailer that we pulled up too. “You know they probably still lynch your kind around here, right? He said half joking.
Looking down at my phone at the picture of Kayla, specifically her tits, I nodded my head. “Already here, ain’t no way I’m turning down pussy now. Just head back to that Subway or something and give me a bit. Keep your phone on though.” I added as a warning before stepping out of the car and quietly shutting the door. Slinking across the front lawn I slid up to the window and shot Kayla a text saying I was here. A couple moments later I heard the window slide open above me and looked up praying not to see a brother or worse a father staring down at me.
“Hurry up, my dad’s still awake in his room so we have to be quiet for now.” Kayla said stepping back from the window so I could climb through. Standing up I gave Kayla a quick once over, surprisingly she looked just like the picture. Medium length dark hair just passed her shoulders, tanned skin a cute face and what looked like a great set of tits concealed under a hoody. After gawking at her I took a quick survey of the room, it looked nicer then I imagined from the outside though it did have a huge pile of clothes at the foot of the bed. Following my eyes Kayla just gave me one of those looks that said ‘hey don’t judge me’.
Now for anyone who has ever met an online hookup in person, you know there is a certain level of awkwardness that accompanies the first meeting. In my experience the best way to get over this hump, at least when you both know your just there for the sex, is to just dive right in. And that’s what I did.
Before long we were kissing on the bed, her legs wrapped around my back and pulling me tight. I slid my hands up under her hoody feeling the tits that had made me drive an hour in the middle of the night and once I finally got her hoody over her head they did not disappoint. Large C’s they were tanned like the rest of her body with soft dark nipples. It wasn’t long after that that various articles of clothing were taking off and strewn across the room. Soon we both lay on the bed, me naked and her in a pair of sweatpants.
Sliding my hand down the front of her pants I felt her smooth pussy lips against my finger. Slowly I ran the tip of my middle finger along her lips until I felt her getting wet. Not to be outdone Kayla reached over me grabbing my dick and slowly starting to pump it. The feeling of her hand pumping my dick and the feeling of her pussy wrapped around two of my fingers had me thinking this would all be over too quickly.
Deciding to by myself some time I separated from her planning to eat her out and by myself some much needed time to calm down. Even at that age I loved to eat pussy and I quickly begin to give slow deliberate licks to her pussy making sure to just barely run the tip of my tongue over her clit. Before long I had picked up the pace speeding up the tempo just until she would arch her back and grind her pussy against my mouth before slowing back down. Finally tired of playing along Kayla grabbed the back of my head holding my lips against her pussy as she came. After a couple more minutes of teasing I sat back in between her legs.
“Are you okay with doing more than this?” I asked already reaching for the condoms in my jeans.
“Yeah and you can do it without a condom if your clean.” She said just as I pulled the condom from my pocket. Now looking back at this it was stupid for so many reasons and I wish I could say that I still used protection and practiced safe sex. But I was 18.
Quicker than anything I dropped the condom somewhere on the bed and grabbed hold of my dick rubbing the tip up and down her lips for lubrication. I began to slowly push in only to have her buck her hips forward forcing my entire dick inside of her (sign number two this whole no condom thing may have been a bad idea.). Encouraged I began to speed up, pulling out until just the tip of my dick was in her and then thrusting back inside. I loved watching the way her lips wrapped around my dick as I slid out of her. We quickly worked up to a good tempo as I watched her big tits jiggle every time I thrust back inside. Noticing where I was looking Kayla grabbed one of my hands and placed it on her tit squeezing it hard.
Suddenly we heard a door open outside of the room. Pulling out of her I quickly ducked down behind the bed getting as close to under it as I could. For five of the longest moments of my life I sat there and waited as I expected her dad to burst into the room and kill me. It never came.
“I think he finally went back to sleep.” Kayla said her head appearing above me from the bed. Sliding up in bed next to her I started locating my clothes thinking that the mood was ruined. I was wrong. Grabbing hold of my dick Kayla straddled me as she slowly started to get me hard again.
“I’m still wet so I’m good as soon as you are.” She said and that sentence alone to my teenage mind had me as hard as a diamond in a snowstorm again. Grabbing my dick Kayla lowered herself down, and I don’t know if it was the position or what but if anything she seemed wetter than before. Wrapping my hands around her body I began to slowly massage her ass, enjoying the way it flexed as she ground her hips against me. Before long we had worked ourselves back up to full speed with Kayla’s hands on my chest as she rode me like a champ.
“Fuck, Kayla I’m getting ready to cum.” I muttered at this point trying every trick I knew to hold off the inevitable. Without missing a beat she picked up the speed even more practically bouncing her pussy up and down my dick (reason number three I shouldn’t be doing this without a condom). Realizing I was fucked if I didn’t do something I waited until she came all the way down on my dick and wrapped my arm around her holding her in place. Rolling her back onto her back I took control again throwing her legs over my shoulders while I pumped away at her pussy. I couple of strokes later and I pulled out shooting my cum all over her stomach and tits.
Falling down next to her we both just sat there catching our breathe for a second as we calmed down. We kissed for a little bit longer before I began to get dressed explaining that I had to get back before morning. Promising that we’d try to do this again I climbed out of the window and phoned my friends to come pick me up.
Thinking that the sex while good wasn’t worth the drive having done it once now and that Kayla was sending up tons of red flags I actually never planned to see her again. A month later she moved within twenty minutes of me and we became very frequent fuck buddies.
Sorry for any typos I'm writing this while doing a stationary bike. Anyone that can provide constructive and is really appreciated as I have a ton of stories to tell, none quite as tame as this, but I'd like to develop a writing style before I post and butcher them.
Source: reddit.com/r/gonewildstories/comments/307br4/just_a_random_high_school_fling
Sounds like the scare factor made the sex better. Am jelly.