I was a Senior In high school and I really liked a girl named Jennifer just because she was so innocent. I knew she was a virgin and I knew she never had a boyfriend before, and she was just starting her Junior year. She was a beautiful tall blond with small perky breasts, a 6 pack from being a 3 sport star, and a big phat bubble but that she was so embarrassed about and she would always hide it. She was very shy when it came to any talk about sex and she would turn bright red if anyone ever mentioned anything about her ass. But when she played sports she couldn’t hide it in the uniforms and it would be bouncing everywhere and she started getting hit on a lot more. I knew I had to make my move soon and asked her out and slowly became friends with her and we started dating. Every kiss or touch was such a huge mountain to climb with her as she was so prude. It would take weeks to get to the next base with her but finally it was time to start rubbing her pussy and she knew it. We would talk about her girlfriends having sex and shaving their pussy’s and how they would talk about our dicks with each other, some of them had pictures of their boyfriends dicks and video’s of them having sex. Jennifer was so shy she would never do that kind of thing but it got her excited hearing and seeing her friends sucking cock and fucking.

My buddy Jason went to the school in the next town over and we grew up together watching porn at each other’s house with his younger brother and a couple other friends so when he started hooking up with his girlfriend he used to take pics of her tits, pussy, and ass and video’s of them fucking and her sucking dick. The other guys would show off pics of their girlfriends too but everyone knew how prude Jennifer was so it was impossible to take any pictures of her. I told Jason that I was going to finger Jennifer on Saturday night down at the park that all of us guys always hung out at. There was this parking spot in the corner of the big parking lot where we had made a little place to hang out in a big bush and you couldn’t see in but you could see out. There was a street light right under the parking spot so you could see everything perfect. He asked if he could watch in the bush and I said sure since I knew she would never know and he and the other guys all showed off so many pics and video’s of their girlfriends, I wasn’t even sure it was going to happen.

So Saturday night came around and I told Jennifer that we were going to a nice restaurant so she wore a nice skirt for the first time on a date and I was so pumped up when I saw it because I knew I was going up it later that night. We had a nice meal and then I went to the bathroom to text Jason that I was coming down to the park and he said he was already down there with the boys, I said the boys? and he told me that his younger brother and our other 2 buddys were down there too. Jason and his brother went to a different school but the other 2 k**s were in my school and a grade behind Jennifer but they were good buddy’s that I grew up with so I said ok but make sure nobody says a word, and then I told them she has a dress on, lol. He said, oh we are ready, brought the lube. I was nervous now that I was about to hook up with Jennifer with my 4 buddy’s watching but was turned on too.