Something About Molly
by Roxy_Raven
Copyright© 2026 by Roxy_Raven
True Story Sex Story: When I first started writing stories about my sex life I made a backlog list of experiences from my past that I knew I wanted to write about and this is one of them! It's the story of my first girlfriend, Molly. Writing this kinda gave me clues about myself because this experience may have contributed to why I'm such a horny kinky slut!
Caution: This True Story Sex Story contains strong sexual content, including Ma/Fa Teenagers Consensual Heterosexual True Story Cheating Light Bond Spanking Anal Sex Exhibitionism Oral Sex Public Sex .
This story is an OOOOOOOLD one! It’s about my first girlfriend back in high school when I was still trying my best to play the role of “teenage boy” and failing miserably at it. 🤢🤮 Of course my first relationship couldn’t be a normal one, no! It just HAD to be with a fucking narcissist! 😮💨 (As did the two that followed, but those are stories for another time.) This bitch was MEAN too! The shit she did would fuck me up for YEARS! 😡 I’m not gonna go into full detail about everything but to give a few examples she pretended to dump me just at see how I would react, she faked being pregnant, she told me she fell off her roof to keep me from coming over to her place so she could cheat on me, and one time she cheated on me at my birthday party with a close friend of mine in my bathroom and forgot to lock the fucking door so I walked in on it!
All that being said, some of the sex we had was pretty hot. She was horrible for me but I stayed with her for years for a reason. Molly is truly a fitting name for such a person! 🤣 Our first time, she decided to leave her bed room door open because nobody was home, or so she thought. Turns out her mom was home and walked by while she was riding me! That was literally how I lost my virginity btw! 😅 Her mom told me later that she was gonna cut my dick off and store it in a pickle jar before laughing and saying she didn’t actually give a shit if I fucked her daughter as long as I didn’t get her pregnant. We definitely never used a condom but I’m intersex so that was never an issue. Another time involving her mom was when I learned she sleep walks! Molly and I were going at it in the living room and her mom stumbled out into the kitchen, fiddled with some things, then walked back to her room. I didn’t know the sleep walking was a thing until Molly told me about it later.
We did a fair bit of public stuff too. I fingered her at the park, we fucked behind a CVS, she gave me head behind the city library. We also fucked in a few friends bathrooms and in my bed with a couple different friends sleeping next to us on the floor. One of those friends happened to be the man who would later become both my first boyfriend and my first partner as a woman, Eric! At the time Eric was a HUGE prude so he was pretty pissed when he learned I fucked Molly while he was asleep a few feet away! 🤣 There was another time she stroked me to completion and used my cum to flavor her popcorn while we were watching a movie on her couch with her sister. We even tried some kinky things. I remember trying anal with her and at one point I tied her up and spanked her till her ass turned red too! Come to think of it ... it’s no wonder I’m such a kinky slut with a taste for exhibitionism when THIS was my first relationship... 🤔 Huh...
Anyways, I think the hottest thing we ever did, in my option, was the time we fucked in her step dad’s favorite chair! 😈 This guy was a MASSIVE prick! He treated her far better then her biological father did (I won’t get into that because it’s gruesome) but he was still a massive asshole! Her family was in the process of packing to move to Minnesota and I was spending time with her for what would (thankfully) be the last time. Looking back that move saved me from who knows how many more years of emotional abuse but at the time I saw it as a bad thing back then. She was the only girl I had ever been with and I was losing her. I wanted to make sure our last time was a good one and not only was her dad an asshole, he was the reason for the move! The entire family pretty much went along with whatever he said and he wanted to move to be closer to his family so that was that. She was reluctant to do it in his chair at first but when she started thinking about how mad she was at him for making her move she decided, fuck it! (And by it I mean me! 😘) I obviously don’t remember all that much about it because it was a VERY long time ago but I do very distinctly remember using the rocking motion of the chair to hit her g-spot, which resulted in her squirting and leaving a giant stain. Her dad was a slob so it blended in with the food stains well and he never noticed! 🤣 If you’re wondering how the fuck I was good enough to make a girl squirt when I was that young, I wasn’t. Molly and I just had a LOT of sex so I got to know her body very well by that point. I loved making her squirt all over me, especially when I was inside her because the feeling of her squeezing me as her muscles uncontrollably contracted was delightful. 🥴 Looking back on it now it’s obvious to me that the entirety of my first three romantic relationships were a vicarious thrill because every time I fucked Molly (or my second girlfriend, or my ex wife) I always imagined what it would be like to be in her position. It’s to the point that now memories of the feeling of a cis girl squeezing down on me are why I love squeezing down on anyone whose fucking me. I know what that feels like and I finally get to be the one to do the squeezing the way I always wanted to! 🥵
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