Obligatory apologies for the long backstory. This all happened about 4 years ago when I [20m] was still in college with my first real girlfriend, Tanya [20f] (names changed for privacy). I was her first everything, and while I had technically had sex in high school, it was unmemorable and for all intents and purposes I considered Tanya my first everything as well. Tanya was extremely petite, 5′ tall, slim with a tight body, A cup boobs that looked great on her small frame.
Tanya and her best friend Penny [20f] were absolutely inseparable. I realized super early on that dating Tanya necessarily involved seeing Penny almost as often. They took all the same classes together, told each other every intimate detail of their lives, even slept in the same bed together (Tanya hated her roommates and Penny had a single room to herself. Nothing sexual…yet). This was all fine with me – – Penny and I got along very well and ended up becoming friends on our own. Penny was also fairly short, around 5’2″, and had a more athletic muscular build than Tanya. She had a long term boyfriend all through high school and the first year of college, but they ended up breaking up around the same time I started dating Tanya. She hooked up with a couple people in the first few months I knew her, and I’d always know immediately because she would immediately call Tanya and I over and tell us every little detail. For the most part, she was always dissatisfied and complained a lot about feeling lonely.