I have an abysmal track record when it comes to dating apps. Believe me, I’ve tried them all. The swipe left, swipe right Tinder formula that you see on every clone and knockoff dating app that promises to find you love, lust, or whatever your heart and/or genitalia desire gets extremely monotonous, especially for a guy like me, who isn’t particularly photogenic and has trouble getting my personality across on a dating profile and a few messages. So color me surprised when one night, I was actually able to successfully score a hookup and let me tell you, it was definitely one hell of a time.
For context, this story happened around 2 years ago, while we were both in college and I was in the process of searching every dating app in the world in an attempt to get laid because why the fuck not? As stated earlier, I didn’t really net much success. Most matches on OkCupid rarely lead to conversations, and the few that did, rarely lead to anything fruitful. I was open about my intentions and admitted that I was down to casually date but that I was very much interested in hooking up. Some women responded to that provocation more warmly than others, but the end result was always the same: me spending a night alone and frustration, relying on Pornhub for comfort.
This particular situation is different from your average dating app hookup story. This woman I had hooked up with was not some random stranger, but actually someone that I had known for a long time since my childhood, so I guess you could say this meeting was a long time coming. For the purposes of this story, I will refer to her as Karlee. Now, Karlee and I have known each other since the 1st grade and even way back then, she had a crush on me. She would do the typical shit like follow me around at recess or bother me for my animal cracker snacks or sit right next to me on the carpet while the teacher read us stories. You know, the usual “I like you” kind of activities that kids do. I thought of her as a friend so I paid her advances little mind as as time went on and we grew older, she stopped showing signs of open affection as the yeast went on. She wasn’t cold towards me, she simply stopped being up under me as it would appear that her crush had dissipated.
Over the years, we went to different schools and kept tabs on each other on Facebook. We didn’t speak often, but we did communicate every once in a while. We were always amicable towards one another, but there was nothing to suggest any remnants of her former passion was still there. All that changed however when I noticed Karlee on OkCupid. I had no idea what she was doing on the app because although we kept up with each other here and there, we weren’t as close as we were when we were kids, so I swiped right on here just to talk to her and inquire what kind of shit she was looking to get into with this app just for fun. She matched with me and after very little small talk, she was very open about her looking for some free dick to fuck with. Luckily enough for her, I just so happened to be in the market of giving out some free dick to satisfy her exact cravings.
Once our intentions were clear, we wasted little time setting up an appointment. Our schedules were busy at the time so we scheduled for two weeks in advance. We spent the time between setting up our appointment and waiting for it to come by catching up with each other, which was great, but I was dying in anticipation waiting to blow her back out. Fortunately, I didn’t have to wait too long as an opportunity arrived just in time for our appointment to happen a whole week before we planned it.
I was at this party somewhere in Lower Manhattan having a good time when Karlee had texted me. We had some conversation where she admitted that she was worried that I’d break her cervix. I’m 6’3 with a stocky build so she expected that I’d be rough enough to break her in half. I reassured her that I’d only break her as hard as she’d want me to. From that point on, I could get a sense of just how wet she was from the tone of her messages alone. We kept flirting and foreplaying in our text messages until I eventually asked if she wanted to see what I’m working with so she could prepare herself. She obliged. For context, I’m 6 inches, so pretty standard in the length department, but I got enough girth to make that pussy run a couple orgasms and then some. I told her that I was at a party so I’ll have to wait until the bathroom was clear to slide her a dick pic. When she inquired about the location of the party, she got really excited. Curious, I asked her what was up and she responded that the place that I was partying at was actually pretty close to her job. Great. She also informed me that her shift was ending soon. Even better.
I could hardly contain the throbbing erection that was suddenly emerging as I was brimming with excitement over the possibility to have her juicy ass pussy gush all over all this hard dick that I have ready for her. I make arrangements to go meet her by the A train stop on West 4th street. As soon as she arrived, my excitement started to get the best of me and my dick was hard enough to cut steel. We hugged, exchanged pleasantries, and went for a little walk before finally getting on the train back to Brooklyn to head to my house. We cuddled up next to each other and had pleasant conversation. She even brought me a snack from her job (she worked at a bakery) and it tasted amazing. It was a cute little mini-date and it felt so wholesome that I almost felt bad about all the naughty things that I wanted to do to her. Almost.
As soon as we reached my house, I led her straight to my room. We sat down on the bed and chatted for a bit before I went and caressed her leg. She commented on my eagerness and I got nervous, believing that I was moving too fast. I was reassured however when she told me that she appreciated my assertiveness because it showed that I was ready to deliver on my promise to satisfy her craving for this hard ass fat dick of mine.
She starts to take her off pants and I respond in kind. I continue to rub her legs and caress her smooth skin with my left hand while feeling up my bulge with my right. I spread her legs and start to feel up on her pussy lips through her panties and she’s starting to soak right through them. She lets out a small whimper as I continue to rub her leg and gently play with her pussy through her soaked up panties. I offer to eat her out so I can taste her juices, but to my surprise, she declines, saying that she would feel bad eating her out after working a whole shift. I told her that it wasn’t a problem to me, but she instead decided that she would make up for keeping that tight wet pussy away from my lips by putting my hard dick all down her throat.
She told me that she was very enthusiastic when it came to sucking dick and boy let me tell you, she damn sure wasn’t lying. She wasted no time putting my dick all up in her mouth and going to town salivating all over it. She smiled and started at my throbbing hard erection with exuberance as she sucked all over like she was trying to rob my very skin of its beautifully dark melanin. I’ve gotten head before, but this blowjob was special because she had an excitement that couldn’t be matched. Her head bobbed back and forth gagging all over to let me know just how much her throat enjoyed the challenge of having this hard dick feel her throat. She decided to take a short break to admire both her work and my dick.
I took the time to slightly gather myself, but she was quick to make my knees buckle all over again. Karlee decided to bless me with the best deepthroat I had ever felt in my life. She put my whole dick down into the back of her throat and let my dick sit in there getting all slobbered over until she had to gag for air. She was making sure to guarantee my pleasure and I very much appreciated her for the effort. I asked for her permission to grab her hair as she continued to pleasure me with her mouth and she was happy to have me do it. I grabbed her hair and gripped it tight and started to control the speed of how fast she continued to suck my dick. It felt great having that control because I usually don’t have that many opportunities to dominate like this. I had fun seeing her submit to me and letting me control the pace at which she enjoyed slobbering on my knob and it just made everything feel even better.
After having her gag on my dick a couple more times, I pull out a condom from out of my drawer because at this point, I’m more than ready to tear that pussy to shreds. She takes the condom and places on my dick, massaging it ever so gently and feeling every throb of my dick as her soft hands stroke me off after the condom is firmly placed on. At this point, I lay her down on the bed and spread her smooth legs open so that I can get a good look at her dripping wet pussy. It was such a wonderful sight to see, so naturally I decided to dive right in.
I start to stroke slowly to get my rhythm going and Karlee lets out a small moan. I gasp myself as I try to get myself accustomed to her soaking wet pussy. It’s even tighter and wetter than I could have ever hoped it would be and I really want to make sure I enjoy this feeling for as long as possible. Her moans get louder as my stroke starts to speed up. I lay into her more and more as I continue to go deeper. I pin her legs up by her head and reposition myself so that I can maximize her pleasure as I keep fucking her harder. I try my best not to slip out as she continues to soak up my dick. After a few more deep strokes, I flip her over so that I can fuck her from the back.
I bend her over right in front of me and she arches her back ever so curvaceously in front of me, tempting me to just drive my dick right through her and put it in her stomach. I insert myself right in her tight pussy and immediately get to breaking her back. I fuck her aggresively as she starts to cum all over my dick. I continue to stroke deeper and deeper as she lets out a load moan while squirting all over my dick more and more. I grab her hair and grip her ass and grip her ass while my strokes aggressively hit her G spot as she starts getting worn out. I start to see her arch giving out and I start to grab her neck while I continue to pull her hair because I’m not ready to let her tap out just yet. She starts getting extremely soaked from this and she cums aggressively all over my dick, moaning louder than ever as her body gives in shakes from cumming so hard.
For my efforts, I get rewarded with her laying me on my back so that she could get on top and ride me. As I laid back, I admired the view before me: this sexy, butter pecan, beauty sitting on top of my rock hard dick with her beautiful perky C cup breast bouncing all up in my face, practically smuggling me. All this excitement started rushing to my dick and Karlee proceeded to respond by bouncing even harder. I lay back and let out a moan of approval as she continues to work. She keeps bouncing until I start fucking her back from under her and eventually we catch a rhythm: me stroking while she was bouncing. It felt like pure bliss. Soon she starts grinding on me while I suck on her tits. Her hips rhythmically gyrate in a soothing and sensual motion and I can feel myself getting close to the edge.
I pull her off of me and pull the condom off so that she can suck me off one more time before I bust. She puts my whole dick in her mouth with an enthusiasm even greater than what she demonstrated with her initial display. As I grip her head and guide her into deepthroating and gagging all on my dick. When I let go, she continues to gag on my dick, and then makes her way to sucking my balls while I stroke myself off. I motion for her to come suck on my nipple, as it’s one of my favorite ways to be brought to a climax, and she complies. She puts my whole nipple in her mouth and licks it nice and slow as she stares me right in my eyes. She massages my balls while she continues to orally massage my nipple, sucking with more energy as I speed up my strokes. I let her know that I’m about to cum and she stops sucking my nipples so that she can catch my nut all over her titties. I bust a huge load and about 5 thick ropes of cum let go all over her chest.
I accidentally Monika Lewinsky’d her sweater in the process and I apologized because I tried my best to aim for only her tits but I was so horny, my dick just decided to do whatever it wanted. She was actually pretty cool about it. After we both recollected ourselves, we both got dressed and I walked her to the train. We said our goodbyes and went about our days. We unfortunately never had the chance to repeat this encounter as she moved to DC shortly after, but whenever I need a good memory to pull out of my spank bank, I gladly recall this memory to get me going. I cherish this night for all that’s worth.
Source: reddit.com/r/gonewildstories/comments/j9mn64/long_time_coming_m