This is a fun story I wanted to share. This story is 100% true although I want to admit this story did not happen recently. I just had some fun on dirty pen pals today and was reminded of this story and found this subreddit so I wanted to share.
A long time ago I was in high school. I played soccer my entire life and even did some football. I wasn’t a nerd, but I definitely cared about my grades a bit (nowhere near top of my class, but took some honors classes and did fine). However, I was definitely a ‘good’ kid. I didn’t smoke, I didn’t drink alcohol, I didn’t have sex. This isn’t because I was some sort of narc or thought I was better than anyone, I just was too scared (lol) to even risk doing it. I would go to the occasional HS party and just hang out completely sober lol. Sure, I missed out on some good times but whatever. I had a high school sweetheart for a time, but all we did was kiss. Got the picture of who I was? Ok good.
Anyway, I was considered an extremely friendly and ‘good’ guy in high school. Completely ‘date-able’ and ‘boyfriend material’. The problem was that I honestly didn’t have that much confidence talking to girls or even flirting with them. I’m not sure why. I was good looking, girls had crushes on me, I wasn’t a complete idiot, and was pretty funny. I just got too much in my own head and wouldn’t even risk talking to attractive girls. One really cute girl I actually wanted to kind of date literally walked up to me one day and said she wanted me to fuck her in the ass. Like, she straight up just whispered that to me. I just smiled and said “maybe…. I mean maybe we could. But let’s get to class right now?” (LOL I WAS AN IDIOT)
Well, there were some sexy twins who played soccer. They were sophomores when I was a senior. We didn’t really have the same circles of friends and didn’t really talk much, but we definitely at least knew that each other existed. Well, I DEFINITELY knew they existed. They were petite, athletic girls who were also hilarious. Beautiful tan skin and brown hair. Great cute smiles too. Anyway, I psyched myself out and decided that they were ‘out of my league’ so I never tried to even talk to either one of them despite me having PLENTY of opportunities.
I graduate high school. I gained A LOT of confidence in the years right after high school during college. I figured out that I really tend to overthink things and, well, a lot of things just aren’t that complicated. I started to have fun drinking. I also started to get more confident and one day I figured out that with a basic sense of humor, a job, some confidence, and basic hygiene habits you have a decent shot of a date (and/or getting laid) with a HUGE amount of girls — so long as you were respectful in the process. Anyway, I realized that I was so over-thinking most scenarios that I missed out on a lot of opportunities (relationships wise, career wise, friends wise, etc). But oh well I was confident now.
Anyway, fast forward 8 years after high school, when I had last seen either of the twins, and I have graduated college and even grad school. I have a great job. Things going really well. I’m still in my hometown. I had gotten out of a bad breakup about a month or two earlier and I finally decided to get back out there and try to date again. I hopped on Tinder (which at this time I had become pretty good at — it’s how I had found numerous girlfriends and.. plenty… of dates/hook ups) and what do you know! I saw one of the twins on there!
I started getting flashbacks and thinking “Oh man. Do I swipe right? Do I ignore her? Does she even remember me?” and then I just reminded myself that I was overthinking it. The only question I tend to ask while I was on tinder was “Would you fuck her right now if she walked through the door or not?” The answer was most definitely yes. She still was a total babe, at least according to her pictures. She still seemed nice too and had a friendly smile.
I swipe right. A few hours later, we match.
I’ll skip the boring Tinder lines — but we eventually meet up for a date. We meet up and, well, she didn’t remember me specifically from HS but we had ALL sorts of close mutual friends. It was funny for her to be like “Why didn’t you ever talk to me?!?!?! Why were you shy???” and I would just not lie and say “Well, you were one of the XYZ twins! You were popular and really attractive! And you still are!” It’s worth noting that she was still totally gorgeous and turns out she was A LOT nicer than I had ever imagined.
So we really hit it off. She didn’t quite have a ‘career’ job yet (which is fine, she was a cute waitress at a nice restaurant, which I think is actually a fine career but she seemed self conscious about it) but she was really sweet and nice — and she had mentioned that she was really tired of dating losers who didn’t have jobs. So, it was really refreshing for her to be on a date with someone with a job and some sense of direction. We are a few drinks in and it’s starting to get to that time. I ask the bombshell question “Do you want me to walk you home?” and she blushes, smiles, and says “Yes absolutely.”
We leave the restaurant and walk to her house. She actually gets a little embarrassed because of how average her house was as she was locking the door. I obviously didn’t care because I’m not like that, but then it dawned on me: **SHE WAS THE ONE WHO WAS NERVOUS ABOUT IMPRESSING ME NOW**! And once I realized that, I became extremely confident myself again and was ready to make my moves. She invites me in and we walk into her kitchen.
She walks up to her counter to get some wine glasses, with her back to me with a small smile on her face. I took that as an invitation to try something, so I did. I come up behind her, put my hands on her hips and start to kiss her neck. I can feel her goosebumps on her neck immediately. She then grabs my hands off her hips and throws them onto her tits. She may be small, but her chest is very busty. She let out a huge gasp of air and started to pant a little as I continued to kiss her neck. She was obviously loving it.
After a few minutes of kissing and feeling her up, she took one of her hands off my hands and wrapped it behind her back to grab my cock through my jeans. I was obviously starting to get hard because in my head I was thinking “**HOLY FUCK! IS THIS REALLY HAPPENING**?”
Now, just to keep things in perspective, I’m about 6’2” and 210 pounds. I work out and most definitely have a muscular build — I am much stronger and bigger today than i was as a pencil neck high schooler. Meanwhile, she’s probably around 5’4” and 110 pounds with an athletic build. TBH she’s barely changed since high school just maybe more muscle.
Her hand finds my cock through the jeans and she tries to squeeze it. She then tears away from me and grabs my hand, giggles, and says “follow me” as she guides me into her living room. We sit on the couch next to each other and start to kiss some more, but then she shifts so she is sitting on her knees on the couch completely facing me. She then starts to kiss me on the neck as she uses her other hand to unzip my pants. I’m thinking to myself “**Holy fuck is this really going to happen?**” She unzips my pants and pulls out my cock, which is pretty much 80% hard.
She starts to stroke it lightly with her hand and then stops kissing my neck and instead just wraps that whole little mouth around the dome of my dick. I see the back of her head, but I don’t need to see what’s happened to know. She starts to salivate and lube up my cock. I can hear her moaning as she’s bobbing her head up and down my cock.
Then, she stops for a moment, and then completely takes my WHOLE cock down her throat. Now, I’m not gigantic by any means, but I definitely have a thick 7 inch cock. I could feel her lips at the base of my cock and could feel the head of my dick basically being shoved down her throat. I obviously let out a good grunt and then spank her (She has on a dress still) a little bit and rub her ass.
“Yeah yeah yeah… suck that cock. Fuck yeah” I murmur out a few times as she keeps going up and down my shaft with her throat. She then takes the cock out of her mouth and I’ll never forget that beautiful site of seeing all that fuckin saliva stringing out of her mouth and from my dick. MMM. So fuckin sexy. She gives me dome for about 5-10 minutes… meanwhile I’m rubbing her ass and wrapping my hand around her ass to rub her clit too.
She teventually got on her knees in front of me on the couch and started to deepthroat me and just staring at me. This happened for what felt like an eternity (in a good way) but was probably only a few minutes… She was starting to get all cutesy too with her eyes “Is this what you like….?” as she would take me all the way down. It was obvious that SHE was the one trying to IMPRESS ME, which again just made my confidence fly through the ROOF and I was LOVING IT.
Anyway she comes up for air again, spit stringing from her mouth onto my cock and she chuckles “Haha. I’m glad you kind of like it messy….” and she goes down and sucks me some more keeping eye contact. Then she comes back up for more air and asks in such a sexy, desperate voice “[My name] .. I’m so fucking wet..[she lets out a nervous, embarrassed laugh]… please don’t think I’m a slut but PLEASE let me ride you. I want your fucking dickkkkkkkk.” she says in a begging and cute/teasing way.
I let out a chuckle and say something like “You think I’m going to say no? Let’s fucking do this.” and I grab her arms and basically pull her up on my lap. She still has her dress on and my cock feels her panties and yeah they are most definitely soaked. I have my hands on her hips and I’m kissing her neck. She takes a hand and reaches under her dress, grabs my cock, and slides it underneath her panties and right into her fuckin drenchin pussy. She lets out a gasping moan and borderline collapses on me as I go deeper in her.
I then wanted to make sure I wasn’t some bitch who was gonna make her do all the work…. so I take my hands and wrap them on her ass cheeks (dress is still on!) and I pull her ass off my dick a little bit and then slam her body down onto my cock as I thrust up. She immediately looked to the ceiling eyes wide open and let out a squeel. She covers her mouth with one of her hands as the other one holds her up for support on the couch railing behind me. I then start to get into that rhythm of just lifting up her little body off my cock and then pulling it down onto my dick as I thrust it up into her.
The couch starts shaking obviously and rubbing up against the wall but it didn’t fuckin matter. She also started to put some of her own energy into me. She eventually stopped looking at the ceiling and just threw her face into my face and kissed me wildly saying all sorts of things like “yes yes yes yes….” or “fuck meeee fuck meeeee.” It was the ABSOLUTE fantasy for me.
We were starting to get sweaty (we were basically still fully clothed to be honest). I rubbed her clit a bit too while she was riding and she had a few quivering spells. Not sure if she orgasmed but she definitely quivered. I was getting tired of being a bottom so I told her to hang on. I grabbed her hips and lifted her up off the couch so I was standing and she having her legs and arms wrapped around me. I started to fuck her a little bit mid air and she was loving it but honestly I could only do this for about 15-20 seconds — but it was worth it. I then clumsily carried her to the bedroom and threw her on her bed.
She immediately bent herself over her bed. She didn’t even need to tell me what she wanted.
I unbutton my pants and they fall to the floor. I lift up her little dress up and pull her panties down to her knees. I then re-inserted my greasy dick right into that pussy. I fuckin LOVE fucking doggy style because there’s just so much power and it’s so primal.
I grabbed a thick knob of her hair and pulled on it and just absolutely fucked the shit out of her. I mean like her whole bed was moving. We knocked over some things on her bedside table because we were fucking so hard. I deep dicked her for probably… 10 minutes… and now we are both all sweaty from all the work we’ve been doing and eventually I felt that little tingle in my dick. No, we weren’t using a condom (and this was really dumb, but that’s beside the point) So I knew I was gonna cum soon. I fuck her more and more and start to say things like “im… about… to … cummmm.” and then as soon as I pulled out of her pussy, like clockwork and without me even asking she wrapped around and got on her knees and looked up to me.
She had a look on her face like she was concerned… like she wanted to make sure I had a good time. She almost had puppy eyes. She kept frantically saying “Face or mouth??? face or mouth?? face or mouth??” And honestly I was in the process of cumming and couldn’t really verbalize anything so I just grabbed a tuft of her hair and aimed at her mouth (she got the picture that I wanted to cum in that mouth of hers) and she opened wide looking up at me. I shoot out my first string of cum and it hits above her upper lip and she just slides the head of my cock right into her mouth.
She then starts to fucking suck on it SUPER HARD. like almost painfully hard. I grab the topside of her head with both my hands as I continue to orgasm. She coughs a few times on my cock, but she doesn’t throw up or anything.
Eventually I stop cumming and we initiate some fun small pillow talk as we clean up the area and ourselves. We decide to take a shower together and call it a night. I’d sleep over that night…
——–
Anyway…. there is a lot more to this escapade but I at least wanted to share part 1! The moral of this story is that confidence is absolutely king. So for all of you guys out there who are wondering if you should go for it… yes. You should go for it. Who cares if you get shot down. You need to go for it! You’re probably more marketable than you realize! Just don’t be an awkward weirdo!!
Source: reddit.com/r/sexystories/comments/beqryh/true_storym4f_a_fantasy_8_years_in_the_making