Heads up: This is very long because I’m not very good at shortening things and it’s a long story overall.

I was recently (as in Sunday, June 10) at my best friend’s (who is a female, while I am a male (also, she’s 16 and I’ll be 16 in 16 days from today, June 13)) house and I stayed over 2 nights, neither of which did we (or really just I, because she would sleep from about 5 am-9 am) sleep but instead just stayed up all 48+ hours just for the fun of it. The first night was normal for us, we just laid there watching movies together. As for the second night, it was normal up until the point when she fell asleep, which was around 4 am. I thought nothing of it and closed the laptop and set it to the side so that it wouldn’t wake her up, but she has always been one to hold onto things in her sleep so, also like normal for us, I had one arm around her and she held me close. Her father doesn’t like the idea of his daughter having a male staying the night with her, but once we convince him to let me stay the only rule is that I can’t sleep in the same room as her. We didn’t break the rule, but I usually leave whenever she falls asleep. She was holding me tight enough and was close enough to the point where I wasn’t able to get up without waking her up, so instead I just stayed with her and held her while she slept, as I thought she’d eventually change positions so that I could go. It was around 4:30 when I checked the time, so I still had nearly 4-5 hours before her father wakes up, so waiting wasn’t the issue. Rather, I soon became half-tired after checking the time. She usually asks me to rub, massage, or scratch her back and a lot of times I do it for her without her asking just because she never complains about it or stops me or says anything about me doing that, so as I laid there I started to rub her back. A few seconds after starting to rub her back, she started rubbing my chest (one of her hands was on my chest already). I had turned to my side before I started rubbing her back just so I wasn’t uncomfortable on my back and I could feel her breath on my face since we were so close together. Now this is when the story really begins; after we stayed like that for about half a minute, she shifted toward me a bit more and next thing I know we were kissing. This was my first kiss, so I had know clue how to react or how to kiss, but it felt good so I did my best to follow her lead for the next maybe 5 minutes. She put one of her hands down my shorts and started stroking my d***, which was also a first for me. I’m not sure why, but I believed that she was still asleep, so I felt wrong for it and pulled my head away. As soon as I pulled away, she grabbed me and pulled me toward the top of her body, so I followed her hands and was then on top of her, and we were once again making out. It felt even more wrong now to me, but I really didn’t want to stop. We made out for about 30 seconds before I felt her hand grab mine. She pulled my hand down to her v***** and I started to rub her through her shorts (I’m a virgin, but I still knew what I was doing for the most part). She started breathing heavier and moaned once or twice and we continued like that until she grabbed my hand again and led me up to her b***, which I began to hold and squeeze since her hand starting squeezing mine – and I knew what she wanted from that. After maybe 5 minutes, I rolled over onto my back and pulled her over on top of me and we continued to make out as she had started to stroke my d*** again. It wasn’t until about a minute like that until she finally said something. She said, “Are you sure you want to do this, [my name]? We don’t have to if you don’t want to.” I don’t know what I was thinking about but when she said my name I felt my heart rate spike and I couldn’t think straight and I didn’t know what to say, so eventually I said, “We’ve gotten this far already, we might as well keep going.” She kissed me again and then rolled off of me and her bed and undressed, again asking me if I want to continue. I sat up and said “F*** it, lets do it” and I rolled off the bed in front of her and undressed. I laid back down and she got back onto the bed and got onto her hands a knees over me, one of her hands on my d*** and the other ruffling the back of my hair and we started making out again. I’m not sure how long we stayed like that, but eventually she sat back and she stroked my d*** for a while. After a few minutes, she said to me me, “Are you hard? You have a big d*** so if you’re not hard enough I could hurt you.” I didn’t know how hard I should be for it, so I told her “Hard enough.” I don’t exactly remember what happened after this besides that I started going flaccid and she was going on about us not having to do it if I wasn’t ready and about how she doesn’t want to be my first if I don’t want her and she was asking if I was scared and was trying to reassure me of things, like that she was on birth control so that I didn’t need to worry if I came early and that we weren’t going to get caught by her parents or siblings. The last things I remember are us admitting to each other that we both have had feelings for each other for a good while, me telling her that I wanted to wait until I know something will happen so I’m ready for it, and her promising me that we’d still be bestfriends no matter if we kept going or not. Well after our conversation in the n***, we put our clothes back on and continued where we were in the movie and everything was back to normal. I had to leave later that day because I had football practice on Monday.

I did bring it up with her on Monday, asking her if it actually happened or if I was dreaming or had imagined it all. She assured me that it actually happened. Nothing was awkward about it for either of us, but she did laugh right before we got dressed and said that if I told anyone that she’d kill me because she knows both places that I live (parents are divorced, that’s a different story). Anyways, Monday night I brought it up again and I went over “another time that I’m ready” with her. Pretty much what the plan is now is that she has to come onto me because I’m too p**** to do it to her and we do it whenever she feels like it (and I’m at her house almost every weekend, so there’s that tidbit of information). I also asked her if this was going to be a one time thing and she told me it doesn’t have to be and I told her that if I like it then I’m not going to want it to be a one time thing but I don’t want to just be seen as friends with benefits or f***-buddies or whatever else and I want to still be bestfriends. So yeah. That’s my story. Hopefully she doesn’t know about this website because even though it’s anon she’ll know it’s me. Also, if anyone has any advice for me about anything to do with losing my virginity or anything like that, I’m open to hear it.