[MF] 22/21 – How I lost my virginity with my high school crush 3.5 years after graduation. (VERY long)

So, there is a *lot* of backstory here since we’ve known eachother for almost 8 years but TLDR, Sarah (not her real name) and I dated freshman year of high school and it was one of those shitty freshman relationships where neither of us could drive and it was just destined to fail, but we remained friends (Even though I still liked her) throughout school and developed a friend group that we hung out with a lot. We all went to different universities after graduation so we kind of grew apart, but we tried to hang out over summer breaks and stuff as much as we could.

So fast forward 3.5 years after graduation to this thanksgiving break, everyone from our old high school friend group is back in town and we are all finally 21, so what else is there to do other than to hit up a bar and get drunk with each other for the first time? So since I lived the closest to our hometown in my own place, everyone met up and pregamed at my apartment. Some real quick info on Sarah, she is latina, about 5’1″ or 5’2″, and she isn’t exactly skinny but definitely not fat or overweight either (which is totally my ideal body type), B-cups (I think? I don’t know shit about boob sizes) and an amazing butt that was just made better by her natural curves. She also has the most beautiful face and smile in the world (sort of similar to Gina Valentina, i guess), and a very bubbly but also sassy personality that makes her just a joy to be around. I, on the other hand, am the definition of an average white dude. I am 6’1″, I have a skinny frame but I kind of have dad bod forming in the stomach area, with an decent looking face and about a 5 – 5.5 inch dick (I actually am too subconsious to measure it so idk for sure). Like I said, average.

I had an almost unconditional on Sarah for about 7 years despite us being apart for so long so just seeing her again for the first time in over a year made me super happy and nervous at the same time. Her drink of choice was a bottle of premade Jose margaritas and during our drinking games she downed about 2/3 of it within 45 minutes so she became pretty drunk pretty quickly. When we began to discuss the uber she sat super close to me and began doing that thing that girls do where she would touch my leg any time she talked, laugh loudly at what I said even though I’m not funny, etc. etc. (God bless alcohol finally giving her confidence to flirt with me). I got the message and began flirting with her back, touching her in the uber and even holding her hand as we were walking around finding a bar.

Eventually we got to a bar, bought our drinks and went straight to the dance floor, where Sarah randomly began grinding on me like I have never seen before. This girl who was always so sweet and shy and reserved when I knew her was now twerking on me in plain sight in front of all of her friends, grabbing my hands off her waist and placing them on her boobs and between her legs in the middle of this public bar, in front of all of her friends. It was the most insane thing that has ever happened to me and I had to make sure that I hadn’t overslept and was in the middle of some super fucked up lucid dream. I was starting to get hard and she knew it, grinding on me harder and even reaching back and rubbing her hands across my crotch. This went on for about 30 minutes until the emotions that had started building inside my drunkass head grew to be to much for me to handle, and I pulled her aside to a more quiet part of the bar, and our short conversation went something like this:

“Sarah, just kiss me now, please.”

“I can’t.”

“Then what the fuck is all of this.”

She grabbed my hand and let me outside where there were a few tables with maybe 10 or so people scattered around them. We sat down and the first thing that she said was “I don’t know why I just can’t get over you”, which perfectly summed up my feelings for her as well. We cuddled up on the bench and talked for what seemed like hours, about how we had secretly liked each other for all this time, but neither of us could find a way to say so, and how we were too scared to try anything in fear ruining our friendship and friend group that we had built. Since we hadn’t seen eachother in over a year, we caught up on everything – school, jobs, new friends, prevoius partners, it was at this point we figured out that we had each kissed others while drunk but nothing else had happened and neither of us had had sex yet or been in a relationship, which I was surprised by considering how confident she was acting, but I was also relieved. Eventually I asked if I could kiss her and she said yes and I got the kiss that I had dreamed of after all of this time. We made out for about a minute until she pulled away stating that we were in public, and we spent a little more time in silence, cuddled together out in the cold just embracing eachother’s presence. Of everything that happened on this night, that was probably the best part, I was literally living in a fairy tale or a teen romance movie and it was the most amazing feeling ever. Eventually our friends got worried and found us outside and dragged us back in where we got a few more drinks and fucked around with pool and one of those arcade basketball games for a little while until we left.

By this time it was about 3AM and we Uber’d back to my place to pick up our stuff. The group plan was for us to have our DD drive us to Waffle House and then go back to Emma’s (another friend that was with us that night) house since she had spare beds and my apartment only had a couch and a beanbag chair for 5 people. Sarah had a different idea though, and I knew without her needing to tell me. I casually implied that Sarah and I would drive seperately to give more room in the car, and after assuring that I was sober enough to drive (don’t worry, I was…barely) we headed off to possibly the worst Waffle House trip ever lmao, everyone was drunk and tired and we were all crammed into this tiny booth so half of my ass was hanging off and all I wanted to do was just go back to my place with Sarah. The food was great as always though. Once we left I finally asked her “We’re not going back to Emma’s right?” and she just shook her head, confirming my suspicions, so we said our goodbyes to the group and drove back to my place.

Now, I’d like to say we started smashing like rabbits in the livng room as soon as we got back, but that wasn’t the case. We went into my room, changed into sleeping clothes and took our time getting ready for bed. It started slow with spooning and cuddling, and I was sort of afraid to make the first move since I didn’t want to do anything she was uncomfortable with. I started rubbing her boobs while we were spooning and then she turned over and kissed me, and it was on. We made out like crazy, years of attraction and lust for each other just all coming out. I had kissed a girl before, but it was someone that I had just met hours before and it was nothing like the pure emotion of kissing Sarah. I went down and kissed her neck and she snapped at me to not give her a hickey, which just made me kiss her harder, and I started moving my hands around her body, exploring her boobs, hips, and ass.

After about 10-15 minutes of that, I asked her to take off her shirt, to which she said no, so instead I just reached up under her shirt and bra and started rubbing her nipples that way. I was afraid she’d turn that down as well but her moans solidified that move for me. Not long afterwards she took her shirt and bra off on her own and my mouth went straight to her nipples, I started gently, just licking them with my tongue, but she immediately said “don’t be scared”, (which by the way ladies, is the one of the hottest things you can say to a dude during sex) so I began sucking on those things like nobodys business, swirling my tongue around them and biting them softly as she moaned along with me. This was when she reached down my shorts and grabbed my dick and started giving me a handjob (the best one she could inside of gym shorts) and I responded by slowly reaching down between her legs and rubbing her pussy over her panties. As soon as I made contact I felt her body shudder and I immediately pushed her panties to the side and began rubbing her clit, and then sliding my middle finger into her pussy. She was very wet but also very tight, and it took her a few minutes until I could slide a second finger in there. She orgasmed almost immediately after I put the second finger in, and then asked me if I had a condom.

I got up and went in my bathroom and put it on, then as I started to pull her panties down, she immediately got second thoughts and said to me instead: “Let me suck your dick”. “Are you sure?” I asked like a dumbass and she just looked in my eyes and smiled at me as she moved down to my crotch, took off the condom (what a waste of a perfectly good condom) and began giving me a BJ. It was at this moment that I literally pinched my arm trying to wake myself up from this insane dream, but nothing changed, and here was the girl of my dreams, fully naked, sucking my dick in real time. It was the hottest goddamn thing that I think I will ever witness in my whole life. Unfortunately it wasn’t a very good blowjob objectively since it was her first time so I didn’t get to cum, but the intent was more than enough to make it amazing. Eventually I motioned her to come up and kiss me and I asked if I could repay the favor. She said “If you want to” so I went down, practically tore off her panties, and went to town. I was a little nervous since I have heard horror stories of a smelly pussy/ bad tasting juice, etc., but she tasted like fucking heaven. I could have laid there for hours eating her out as she forced my head down into her and moved her hips with her moans, but after about 5 minutes she came again and pulled me back up to kiss her, tasting herself on my lips. She whispered in my ear, “Slow” and without even getting another condom she grabbed my dick with her hand and placed it on her pussy. Unfortunately, the story kind of comes to an end here, neither of us had any clue what we were doing so it was sort of awkward and she was so tight that I could barely get my dick inside and couldn’t go deep without it hurting her (Disclaimer: even though we didn’t really have sex, penetration happened so I’m counting it). So we gave up on that and she gave me another BJ (and I still couldn’t cum even though I was trying my ass off too, fuck whiskey dick) and we laid back down and tried to sleep.

I think we got about 2 hours of sleep combined that night as I couldn’t sleep with her ass pressing up on my dick and vice versa, so we gave up on that and just laid there cuddling, holding hands and making out watching netflix until we each had to go leave and be with our families for thanksgiving. We had the relationship talk and decided to give it a go, but unfortunately we couldn’t find a time to see eachother again before she left for school and despite her flirting with me the entire weekend over snapchat, she eventually called off the “relationship” for reasons that I don’t know yet and we have barely spoken since. I was devastated, as all of my feelings for her had came back in full force, and I am still trying to get over everything that happened and the teen romance fairy tale that could have been. I am hopefully going to see her again over this upcoming Christmas break so we can talk it out and see what we are feeling about us in the future.

Sorry to end this on a sad note, but that is life sometimes and I wanted to write this all down somewhere to get it all off my chest. I’ve never done anything like this before so please give me any feedback you may have and hopefully I will have some more stories to write (preferably with Sarah) soon.

Source: reddit.com/r/gonewildstories/comments/ecwd2m/mf_2221_how_i_lost_my_virginity_with_my_high