For context of how my ex, Grace and I got to this point, please refer to parts 1 and 2 of these posts. Thanks!
After a few weeks of becoming more sexually familiar with each other through oral sex and masterbating each other, I started heavily considering going to the next step. I wanted to penetrate her. Yet, I found myself somewhat scared to initiate it. Up to this point, we hadn’t gone any further, so what if she didn’t want it?
I knew that we had an upcoming fall break trip with some friends to one of their grandparents’ lake house. This seemed like a great time to begin exploring the idea of full on sex because we wouldn’t have to worry about our parents being around.
The week of the trip arrived, and we headed up to our friend’s (who we’ll just call Anna) grandparents’ house. With us came some other friends, who we’ll just call Tommy, Ashley, and Mike.