This happened about a decade ago. I was in my early-20’s at the time. It was summer and a group of us decided to give a shot at a bar tour on one of the jumping ends of our city. There were six of us, four men, two women. One of the women who would be coming was named Olivia and my god was she beautiful. I had known her for about 5 years at this point, we were pretty close. She was a smoking hot, petite redhead. She was as flat as a board and kind of tomboyish, I never knew her to wear a bra. I knew from listening to her over the years that she very much had a girly, sun-dressy type girl hiding inside, but she always felt insecure about her body. She was a big drinker and a pothead, and was the type to get very flirty and sexual when wasted. I wanted her badly, but she had always been with someone or was otherwise occupied. A couple of times we had been drunk and done the touchy flirtatious thing, but nothing had ever happened. More than once I had to save her from making a drunken mistake at a party with a guy. We liked and trusted each other.