This story happened back in the late 1990's right before the internet really kicked in.
For a number of years, I worked in a small office which mostly entailed myself and our company office manager Jackie with the occasional consultant stopping in to work or make copies. But for the most part, it was me and Jackie who handled the company business in a small office. Because we both worked in such a small office together for several years, we had become good friends but that was all we were as Jackie was married with kids and her nice house with a white picket fence. We were both 30 at the time.
Jackie was a nice petite 5' 2" 115 lbs with a nice ass and perky breasts and always dressed really nice everyday for the office. She was a hotty MILF and I must admit was not bad to look at every day at the office.
As for me, I had just gotten myself into the best shape of my life by following a bodybuilding workout which set well on my 6' 165lb frame. Now that I had the look, wanted to start getting into the online dating scene looking for a girlfriend on Match.com. Keep in mind, this is the early period of online dating which you got two paragraphs and a few pictures to sell yourself to the ladies for dates.
This was also the early stages of digital photography and I had bought a digital camera to take a few pictures of myself for my new Match.com profile. Being the early period in digital cameras, this camera I bought did not have a timer feature to allow me to do a timed selfy with so that meant I needed someone to take my profile pictures for me.