Back when I was 22, I’d just broken up with my college sweetheart and began dipping a toe into the wider dating pool. My roommate at the time, Jane, was a few years older than me and worked in software development. During the week, she basically lived at the office, but when it came time to play, she actually proved to be quite the wingwoman. As an occasional sugar baby, Jane had developed a thriving network of admirers and contacts on the local party circuit. It was during one of our nights out that my erotic life came to an unexpected turning point.

As similar-looking brunettes with long legs and small busts, Jane and I could have easily passed as sisters, and we routinely swapped outfits. I was standing in front of the bathroom mirror scrutinizing my bra-free boobs in a backless halter top when I heard Jane come... Read More