slight preface, I added “***’s” to where it gets juicy so if you don’t want to read the lead up skip to there. this is my first post here so please be gentle and I hope you enjoy!
I was 21 at the time of this story and had been dating my now ex for just about 6 years. she was pretty much my first everything except kiss and on my 21st birthday I learned that she had been cheating on me for only God knows how long. I actually had plans on marrying this girl until all this happened so needless to say I was devastated and extremely depressed. couple of days go by and I was even stupid enough to try and win her back but she had already gotten involved with someone else. since we had been dating since I was 15 and I had been loyal the entire relationship I hadn’t hooked up with another girl pretty much ever aside from just kissing and dumb shit you do as a teenager that seems really cool at the time but you look back and its just straight up cringe lol
about 2-3 weeks go by and I felt more lonely than ever before in my life when suddenly I get a message on my Facebook. it was this girl I had known back in high school we’ll call her Lena. she messaged me and asked me if I was doing alright after the breakup and how I was handling it. being completely oblivious to what was actually happening I lied and said Im handling it great and am currently exploring my options. she lets me know that she is there for me whenever I need her (ya know the usual just checking on you messages) then a rush of adrenaline hit me like a freaking freight train and something compelled me to write back, “hey are you free anytime soon? just to take you up on your offer of being there for me if I need you.” my game was way off and I was super rusty at flirting in general seeing as how I wasn’t flirting with anyone other than 1 person for 6 years and to this day I have no idea how or why I even replied back. to my amazement, she actually said how about tonight? so I replied back a little hesitant, “wait is this a date? because I just got out of a relationship.” and she replied back instantly. “wait till the end of the night and if it went well, we’ll call it a date.” I agreed and immediately hopped in my car, flew to my barbershop, and got ready for the night. it was a very strange feeling getting ready for the night and I honestly had no idea what to expect. at this point I didn’t even think we would be doing anything sexual especially for reasons ill get to. she didn’t even say what we were going to do and again I was still stupidly oblivious and still kind of had my ex on my mind so I had no intentions on even doing anything physical.
the clock strikes 7 and I text her that I’m outside.i got my haircut, was dressed in regular stupid clothes still thinking we weren’t doing anything special. I still remember it vividly and cringe just thinking about it. I was wearing my Flash symbol shirt ya know the red flash that runs fast from DC comics? lol and some black cargo shorts. I figured id take her to a local sushi place and maybe just talk or whatever. now before I say anything about her let me be clear Lena wasn’t really my type in high school. I fully acknowledge that I myself am most definitely not a 10 out 10 either but nevertheless, in high school she had terrible skin, was super dorky but in the worst ways possible with an awkward lisp because of her retainer, and just wasn’t appealing in the slightest for me. if I’m being honest if I hadn’t been depressed beyond belief there’s no way in the world I would’ve agreed to take her out, but ohhhh my fucking God… talk about a fucking glow up. she came out of her house wearing a tight white short dress with red flowers on it, she had long straight dark hair, it was summer time so it was also golden hour since the sun was going down, she was Puerto Rican so she had this perfect caramel colored skin and her skin was the most clear skin I’ve ever seen completely changed since high school, and her body, omfg her body was model worthy. women literally pay to have their bodies look as amazing as hers. she had thickness in the absolute perfect spots, a huge ass but not so huge that it looked out of place and it was tone, you could tell she had worked on it for years, she was only 5’1 but her legs were flawless in her heels, perfectly perky D’s, could make an argument for DD’s, and a tiny waist. she had a textbook hourglass figure. I felt like I was Dr. Grant from jurassic park when he sees the Brachiosaurus for the first time in the jeep. my mouth dropped and I was in awe and I immediately felt embarrassed because I was wearing a stupid ass flash shirt and goddam cargo shorts. I hopped out the car and went to her and she greeted me with a long hey and immediately hugged me. idk if this is weird or not but she also smelled amazing like vanilla. she stepped back and almost involuntarily I looked her up and down at disbelief this was the same Lena from high school. her retainer obviously did its job too because her smile was to die for. mixing the perfect amount of adorable and sexy. after a little bit of chit chat we got in my car. her legs and ass looked fucking incredible sitting in my car and I just couldn’t stop staring until she looked at me and smiled and said with a chuckle, “so are you just going to stare at me or take me out?” I took a couple seconds to clumsily say, “uhhh yup lets go get sushi.” and we were off.
for the sake of the length of this story I’m going to condense dinner as much as I can. we talked about what was going on after high school, she talked about her going to college and I talked about my college and we then discussed our ex’s. she asked me what happened with mine I told her and turns out she also only dated one guy ever before and it was a 3 year relationship. she then said to me, “I almost walked back in my house when I saw you seeing as I’m more of a marvel girl myself.” I was immediately embarrassed and was apologizing saying, I had no idea she was going to look like THAT. she was totally cool with it, thank God. then things got… interesting after one blunt question. out of the blue she asked me, “so when was the last time you had sex?” I almost choked on my salmon roll. I said, “its been months to be honest. me and my ex had been on a dry spell before I found out she was cheating it had been like 3-4 months.” she replied, “ok just asking.” but with this smile that just screamed I want this guy. so I asked her the same and she said about the same maybe a little longer. she then said she had a crush on me in high school. I obviously didn’t but I couldn’t tell her that so I played it off that since I was in a relationship I didn’t really see her like that at the time but I sure as shit had a crush on her now. she smiled and was like you like me now right? and I of course said yes. after a bit more talking we went back to my car and she put lip gloss on her amazing lips. just enough plump to them that they were thick but not huge to the point they looked fake. I had an extremely loud sound system so we didn’t talk much on the way back to her house because she plugged in her phone and we started rapping our favorite songs and jamming out. as a side note I no joke almost crashed like 4 times just staring at her amazing body and just admiring her beauty whenever I could.
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we get to her house and I didn’t want to leave her. I open her door and walk her up to her front door and she says to me, “so was this a date?” I said that I really wanted it to be and then she leaned in and kissed me. I have never wanted to kiss someone so badly before in my life. I also had more adrenaline pumping in my system then I had ever had before. I then grabbed her waist pulled her in closer, it felt amazing to finally kiss someone different and someone so fucking sexy. feeling her perfect D size titties press up against me made me instantly rock hard. keep in mind I hadn’t had sex or any physical contact in at least 4 months so even a little stimulation was driving me crazy. she pulls back and says that no one was home.i felt like this was an absolute blessing from God I remember thinking to myself is this his way for apologizing for my ex but I then was thinking to myself now’s not the time for a fuckin philosophy class. we went inside and it was indeed empty. still not fully realizing what was going on, I just sat on her couch while she went to the bathroom. she came back out and without even a word she straddles me and we start making out. her dress rides up and even through my stupid ass cargo shorts I can feel my tip just barely grazing her pussy. I had my hands on her waist (I’m a shy and pretty timid guy so I didn’t want to screw anything up and make her want to stop) she then pulls back from kissing me and stands up. she says to me, almost demanding,” pants off.” as if she was my queen and I was her subject. without a word, I ripped those shits off as fast as I could. I looked down and I was amazed again. my dick is nothing too special I’ve always considered myself to be slightly above average 6.5 inches but unfortunately not the thickest I’ve never actually measured the girth but its about average id say. but then I took my pants off it was like another blessing. I guess it must’ve been adrenaline from finally hooking up with another woman but my dick was a solid 7.5 and getting thicker and thicker with every heart pump from my ever-increasing heart rate. to this day I have no idea how this happened but I wasn’t going to question it. she smiled in approval and without skipping a beat she just bends over and starts sucking it. I didn’t know what to look at or what to even do, she was still in heels and she just effortlessly bent over and started blowing me. should I look at her amazing ass perked up from bending over? her perfect titties on the brink of falling out of that tight white dress? her plump lips wrapped around my dick? and then as if she heard the millions of thoughts in my head she looks up right into my eyes with it still in her mouth and winks at me and takes me all in. I have NEVER been so turned on in my entire life. with just one wink, I was hers. she had me in the palm of her hand and she knew it too. I could see her smiling slightly each time I moaned as she kept going up and down and it was driving me crazy. after the best blowjob I have ever received, she stands up and says, “since you already have your pants off its only fair I take something off too.” she lets out a little giggle at the end of her sentence too… she knew she was winning. then without me even catching enough of my breath to respond, she slips off her heels and starts taking her dress off making sure I’m watching her do it. this is when I saw she had a belly button piercing and a ridiculously sexy tattoo of some flowers going from her hip all the way up to her top rib. tattoos are my ULTIMATE weakness and my biggest attraction. I saw this tattoo and honestly thought I was going to pass out from being so turned on. my heart was pumping so fast I honestly didn’t even feel it anymore. she put the little white dress to the side and then took her thong off. I then said “hey that was 2 things.” and then she said, “yea and now its your turn for the second” being the smoothest man alive that I am (lol), I then took off my watch and set it on the table next to the couch I was sitting on and she then said, “fair is fair” and took her bra off. seeing them out of the bra they were definitely DD’s but with perfect sized nipples so they looked perky and perfect. she asked if I had protection and I of course had no intentions of having sex so I said no. she then ran to her room and pulled out a condom that had her college logo on it, saying “I knew It was a good idea to go to orientation”. I start putting it on and she then takes my shirt off and straddles me like before. we kiss a little more and then I got tired of being timid. if this was going to happen I was going to enjoy it and savor it. so as she reaches back to put me inside her I shove it in to her surprise. she let out a little gasp and smiled but I was in brute mode. grabbed both ass cheeks and started to slam them down while in rhythm with me pushing myself in deeper. now was her time to be pleasantly surprised. she let out another gasp and smiled grabbing my hand and pinning it against the couch and the other grabbing my face gently yet firmly pushing it back desperately trying to regain control over the situation. I then picked her up and bounced her off my hips going in as deep as I could. again, mustve been adrenaline because I’m not that strong of a guy and I was literally holding this girl up fucking her as hard as I could. I put her down on her back and put both hands on the back of her knees and continued to fuck with everything I had. she just looked at me moaning and gasping for breath, I wanted to show her I was still in contention to win this invisible competition we were in of who got more turned on by who. she wraps her legs around my waist and starts to claw at my back just firmly enough that it felt amazing. I had to slow down slightly to avoid cumming too quickly so I took the time to pull out and saw all her juices and cum all over it. I then lick all over her body and especially that tattoo, I sucked on her perfect tits some more and before I could reinsert she stands up and shoves me back down on the couch, turns around and puts me back in her. now she was fucking me. almost as if she was angry at me for making her cum she fucks me harder than my ex ever did in the entire 6 years we dated. her ass was so big and tone it started making loud claps against my body as she moaned and looked back at me with her gorgeous smile as she rode me. I couldn’t say or do anything except accept the fact I was definitely going to lose this time. I start slapping her ass and the more I do the faster she goes. I then tell her I’m going to cum and she chuckles and just simply said “good.” I can’t believe I even lasted this long we had been going on 20-30 mins by now probably 40mins if you include the foreplay and for not having any physical contact in at least 4 months I was in shock I didn’t cum in the first 2 mins. she hears my moans getting louder and then tortures me by going super slow until I finish. her pussy lips gripping me as she slowly lifts up until just the tip is inside and then slamming back down over and over again until I finally tell her I’m cumming. she keeps me deep inside her this time and shakes her ass on it while I cum possibly the biggest load of cum I’ve ever had in my life.
she stands up and turns around to straddle me one last time, and kisses me and just said, “wow I was not expecting my day to go like this.” with another one of her sexy chuckles. I get dressed and she walks me out, kisses me at the door and says, “we definitely gotta do this again sometime.” I didn’t know what to say, still in a state of euphoria, and just kissed her and said, “most definitely.” Got in my car and took off.
we had numerous other hookups over the course of the year after this first one but she eventually ended up moving away with her family far away. we are still friends to this day though so who knows lol maybe we can relive the past someday.
Source: reddit.com/r/gonewildstories/comments/i9xfuk/m21y_first_time_hooking_up_with_a_different_f22