First Cuckold experience/First Sexual Experience

A little background I grew up in a very religious household. This happened in my old High school health class where we never had an offical teacher so it was just a bunch of substitutes coming in so we never really learned anything.

About 10 years ago in my high school health class I became friends with Kassandra(Fake names obviously). While there was never anything between us she was very open to me about her sexuality including telling me a few personal stories. During this point in the year we were both virgins. Later that year she lost her virginity and told me about the experience but that wasn't until a few months later.

We both sat in the back row away from everyone. For a few weeks an old friend, Henry, who I grew apart from a couple years before ending up joining us during class. The main difference was he had confidence around women while I was too shy to even ask someone out.

One day Kassandra made a bet with us where the winner would get to put our hand in her pants. Sadly I lost. After class we went to a secluded area. I went along because Kassandra invited me to and couldnt say no. Slowly Henry moved his hand into her pants and started rubbing her pussy. Kassandra tried to stay quiet but her whimpers turned me on more than almost anything else has since.

This went on for about 10 minutes before Kassandra came. That was the first time I've ever seen a woman cum. Once she calmed down we all left. Henry for the next couple weeks continued to finger Kassandra and would rub her tits and ass over her clothes even in class. The whole time I could do nothing but watch.

Henry ended up moving to a different school and Kassandra and I continued to hang out until we finished that class but I never found the courage to try anything with her.