In the summer of our Junior year of college, a male lover of mine Quentin (not his real name) and I spent a week together on Cape Cod in P-town. We’d spend our days going to LGBTQ bars and we’d often role-play as “brothers”. We loved flirting with anyone and everyone, playing up our roles and then gauging their reactions as we’d sneak a touch or a kiss that was far too inappropriate for siblings. Most people wouldn’t really react or were even a little stunned but one older woman had a different reaction.

Alice (again, not her real name) was around twice our age, and each time we’d slyly touch each other, including me openly rubbing Quintin outside his shorts, she would laugh and tell us how bad we were. She asked if we got high and invited us to a house she was staying at just outside of the town. As we sat down to smoke, the conversation immediately turned to sex. She kept asking how far we’ve gone and we kept demonstrating till eventually we all ended up in a living room with her sat naked in a chair watching two “brothers” 69’ing on a couch. She enjoyed taking charge, even directing us a bit, and we got so into how much she loved it.

The three of us had sex for over half the day, in different combinations. She would watch and feed our dirty talk, but would join one or both of us when she wanted. The most memorable part of the experience was when she was laying back in a chair with Quintin kneeling, his amazing body thrusting between her spread legs. I was happy just watching but Quintin waved me over. I slid into him while he was still in her and we became a chain of lust. Before long this sent her over the edge in an orgasm I still remember today. It sent Quintin off as well and I felt him flex as he matched her orgasm with his own. The sound of them both orgasming and the feel of his ass convulsing sent me into an orgasm that felt like my nervous system had left my body through my dick and I added my own moans to theirs. After a few minutes which felt like hours we collapsed into a puddle each trying to catch our breath.

Later as we got a cab back to where we were staying, we were not sure if Alice knew we were role-playing or not (we both secretly hoped not). We never saw her again on that trip or any trip I’ve taken to P-town since, but the experience was unforgettable!