This story happened a few years ago when I was in high school.
So I had a crush on this girl I knew called Taylor, for about a month. I finally worked up my courage to ask her out. We dated for about two months when we had our first sexual experience together.
It was a Saturday night and not much going on, because I live out in the country. The area has a decent size town to it, but not much to do unless your 21. A friend of mine was having a party at his farm, so my girl and I decided to go check it out. There were about 20 people there, all people from our school. We had a bonfire, some music blaring from our trucks, and the usual party scene. We had been hanging out for a while, when Taylor asked if I wanted to go walk through the trail they had on their farm. I said sure, why not. It wasn't a long trail or anything, but it was a really nice walk under the stars during the summer. It was almost like a scene from a movie. It goes by a lake, where we decided to stop; we lay down next to the lake looking at the starts. I had her cuddled up in my arms. I then leaned over and gave her a kiss. She then brought up the topic of sex. Something we only had discussed once or twice before. I told her that I didn't think we were ready for sex yet. We turned the topic to something more innocent for a while, but then I asked her if she wanted to go swimming. She said sure and took off her shirt and shoes leaving on her sports bra and shorts. She looked over at me and gave me a 'what are you waiting for' look. I said I didn't really want to get my clothes all wet, because I had nothing else to change into.
We then gave each other an awkward/playful/sexual look. She was the first one to break the silence. She said with sort of a nervous laugh, 'Well we could always go skinny dipping.' Of course I agreed. We had never seen each other naked before, but we slowly started to kiss as we stripped down. Once we were naked we raced into the water and swam around for a while. As we played in the water, my boner kept rubbing up against her. She finally said, 'Do you want me to help to take care of that?' Respecting the fact that I just told her I didn't want to have sex just yet though, she offered to give me a handjob instead, which I anxiously agreed to. We then got out of the lake and laid in some nearby grass, both still completely naked. It was obvious that we were both very nervous, we were both still virgins and hadn't done anything real sexual yet, but as soon as she took hold of my dick, I just relaxed and embraced the awesome pleasure she gave me. It was incredible. After she was finished Taylor and I got dressed and went back to the party. It was a fun night!