Sex Stories part I: How I Lost My VirginityI’m not sure what..
🕑 Added 2025-03-21 01:42:14 +0000 UTC
Sex Stories part I: How I Lost My VirginityI’m not sure what made me want to start this series and share this information with you. Part of me thinks it’s interesting to hear a side of someone’s sexual journey. There’s something erotic about it and another part of me wants to share it because I’m sure not many people do- not many people hear about stories that pertain to other’s sexual lives in such deep detail. As such, I felt the most convenient way to convey this information to you is through text as opposed to hearing me talk about it. Think of it as a sexual auto biography of sorts. Maybe I’ll release the audio version someday... I grew up religious and as such, any sexual acts meant certain doom in the afterlife for me. So, I repressed a lot of urges I had to be with any woman throughout the younger years of my life. I had opportunities to, maybe more than one should have at my age, but I never pursued or accepted any advances from anyone. It’s interesting. Both men and women have asked me, and I always said no. Thankfully, I had access to the internet and knew how to erase history from my computer growing up. This was my outlet. Sometimes I’d log on three/ four times a day- especially when no one was home, or I had nothing going on. I didn’t realize how intense my feelings were and how unnatural it was for me to feel the need to release these urges. I knew it was common to a certain degree, but looking back, I felt like it was excessive. I’d get to class early and head to the bathroom with a video preloaded or excuse myself. I’d then go into the locker room before anyone was there before lacrosse practice and do the same thing. It was very ritualistic for me. Even days when I was sick, I could never contain myself. I had a few girlfriends, don’t get me wrong, but we’d only ever make out or touch each other. The first person I ever kissed, made out with and fingered was the same person. My first kiss happened in a movie theater (fitting for the story as it progresses). The first time I made out with her was at her house and the first time I fingered her was as the same place. I remember the first time she gave me a head. It was at night and outside. It felt amazing and I thought, if sex is as good as this, then I’m going to be addicted. It never went any further though. I wanted to “save myself”, but the opportunity to not “save myself” never happened. Towards the end of our relationship, one individual made it apparent that they were, and always have been, really into me- her best friend. We were at a party once and my GF and her were at the same place, different areas though. My GF was in one room alone, and her friend was in another. I remember me making out with my GF and leaving to go tease the other one. What was I doing? My GF was trying to make it obvious to me that we were alone in there and no one would bother us but... I didn’t care. The idea of making out with both women was far more appealing than losing my virginity. Isn’t that a strange concept. Why sleep with one woman, when I could be touching two. Looking back, why did neither of them questioned where I was going and how they didn’t catch on is still today a mystery. I’m still friends with my then GF’s friend, and it’s nice to reminisce on these weird moments of growing up together. She eventually found out what I was doing. She wanted to work things out, but I felt dissatisfied and disappointed with myself. She wasn’t really my type anyway, but her friend was so enticing. I think a part of me wanted to be with her. Not just to have fun with her, but to also be in a relationship that I was happier in. I remembered we texted about sexual fantasies a lot, and I had to fight the urge. The best thing to do was to remain friends with her and distance myself. The guilt I had against myself was too strong and it helped me stay in line with what I was believing at the time. My type has always been consistent, oddly enough. Fit woman, smaller breasts, usually dark hair. These women embodied that to a certain degree. I always cringed at the women with large boobs, light blonde hair, you know the type. I wasn’t attracted to them. I always sought after videos of “natural” looking women. Looking back, I can remember a few videos and stars I used to frequent but for the life of me I can’t remember who they are or what videos they are. Probably for the best though. I kept my faith and my beliefs into the summer before college. That summer is when I met a woman at the restaurant I was working at. I knew she was in college because she graduated a year before I did, but since she went to college out of town, I only saw her during the summer. Summertime was the only time she was free. I knew she was a cheerleader, but she was also really smart and apart of clubs during the spring. I always thought she was attractive. Back in the day, a simple picture of a woman with clothes on was all that was needed, and she was no exception. I remember days after working with her I would go home and think about her. Just closed my eyes and that was enough. We got close and we exchanged phone numbers. I would always make her laugh and, me being clueless at that age, had no idea what was going on or what was about to happen. I remember this night well... It was the night before The Dark Knight Rises came out. I went to my local theatre with a few of my friends to catch the midnight premier of the show. I was, and still am to a certain degree, into Batman and DC Comics. I got a text from the woman I worked with stating that she thought she saw me. I ignored it. “I’m with my friends, I don’t have time for girls” -I cringed when I wrote that, but it was the truth. Oddly enough, one of my friends I went to the theatre with was with someone who wanted to sleep with me throughout school. “Don’t talk to her,” she’d always say. I could take care of myself. She started to text me fairly consistently while we waited for the movie to start, my friend side eyeing me. “I’ll be late when the movie is over lol”, “it’s a far drive back for me”, “do you live close to here? Just wondering lol”. Again, completely clueless, I just thought she was asking questions because she was honestly “just wondering”. The night was coming to an end, and I drove some of my friend's home, including my friend who was into me. On the way back we talked about our relationship, and I told her that she was never really in the friendzone. I could always see a future with us. This meant a lot to her of course but, again, I didn’t realize what was about to happen or the implications of telling her that would entail. I dropped her off and went back home. Apparently the one who had been texting me all night was still in town. She was so tired and didn’t want to drive home. I told her to come over, no one would be home when she woke up in the morning. We got back to my place, and she had a bag with her. Almost as if she prepared for this to happen (she 100% did). She asked who home was, where everyone was, when they’d be back etc., My clueless ass thought nothing of it... We got inside and within the first few minutes, she made it obvious that she had no intention of sleeping. We began making out for a long time. Nothing else, just her and I kissing. I wanted to do more with her. I knew what I was doing but I was afraid to. “What if she doesn’t want me to?” - another cringe while I typed that. It was getting early, or late, depending on how you look at it and I put my hand down her pants. I have never felt a woman as wet as she was. I started to finger her. Slipping my fingers inside of her while she gripped my cock. I was so hard it was painful. We continued to touch each other. My finger sliding out every so often to rub her clit, and her pulling out of my pants to switch hands. Never did the thought occur to me to take her pants off and fuck her.The hand job fest lasted just as long as the make out session. Up until this point, we were both sitting on the floor. About a few hours in she put her hand my chest and I went to lay on the floor. When she did, she took my pants off and she audibly gasped when she saw my cock. She just stared and didn’t say anything. After a short while she grabbed it and slowly started to jerk me off. She wasn’t trying to make me cum, and I wasn’t trying to either... not yet at least. At this point it did finally hit me “I’m going to have sex.” And I wanted to. She eventually stopped and took her pants off and continued to do jerk me off slowly. She kept biting her tongue and finally she got on top of me. “Is this, okay?” She asked, I nodded my head, too nervous to speak. She grabbed my dick and slowly put me inside of her. The rush I felt still lingers with me to this day. The warmth and wetness and tightness of her vagina. It’s all I could focus on. With every little move and bounce I was that much closer to cuming and within literal seconds, I did just that. It was intense, more intense than any orgasm I’ve ever had. I just had sex, and I had to go to work... I had her get off me and I rushed out the door. She thought I didn’t like it, but it was just the opposite. I wanted more and I was craving her. She was all that I could think about. This time though, I needed to be on top. I wanted to do it properly. Later that week I got the chance to. I went over to her house, and no one was home. It was still summertime so we didn’t have college, and her family was on vacation. I remember talking to her. She told me about all the signs she would give me, and I just never picked up on any of them. We were in the bed and started to make out, but I wanted to fuck her immediately. I took her pants off first and started to finger her. Shortly after, I took mine off too. I was excited to be inside of her, but what the fuck was I doing? I’d look back to when I’d hump my pillow, or whatever else I had, and I used the same motions on her. She really liked it. I also lasted much longer, thinking about stuff like football and Batman to keep my cum at bay while the sounds of her euphoria moans filled the room. I came inside her. A few minutes later we fucked again. I’d love to say we did this all summer, but we didn’t. Her parents were swingers, and that’s the life she’d ever known. She wanted to date me, and we did, but she was always after someone else and it broke my heart. I couldn’t keep doing that with her even though I wanted to be with her physically my heart couldn’t. We ended things when we went back to college. My first semester was filled with heartbreak, but the winter before my second semester and into that semester and beyond, I started to date someone new... I’m sure you know where this is going.
