Finally, after all my patience with this beautiful woman, I've done it with my step mom's friend, who we'll call Steph.
To start, Steph has been very flirty with me since we've met when I was 16. She always hugs me and calls me cutie, etc. It used to make me uncomfortable but eventually I realized, holy shit this woman is incredibly sexy. Steph is blonde and fairly short (5'3" give or take). She has nice C cups and a nice round ass for a white girl. She's had two kids (and she's only 27) and still looks amazing, which made her even hotter in my eyes. I've never pursued anything and always just left the flirting there, but at this point it was my graduation party, and I'll soon be moving 4 hours away. So I pursued…
During my graduation party, we were sent to the store (which happens frequently during parties, she always volunteers to make quick runs to the store for my parents and I'm asked to go along with her) and on the way I had been thinking intently and nervously about how this could be my last chance to at least pursue something with her, and I finally got to it. I figured that if anything is gonna happen, it'll happen now. So before we went into the store I asked Steph to wait to go inside cause I had to tell her something. So I told her what I was thinking.