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.
I did not want to ask any friends as online dating was really looked down upon by most people back then, so I needed to keep this out of the view of my group of friends. This led me to ask Jackie if she would not mind taking a few pictures of me for my online profile for my new dating ad. She agreed as being a good friend that she was even though she said she did not know the least bit about taking pictures but was game to try. I told her it would be easy and that I would bring in my digital camera the next day for her to take a few pictures of me first in my business suit as I wanted to show that I was a professional and how good I could look being cleaned up.
The next day I came in with my suit on and showed Jackie how to use the camera and we found a place in the office with the best light against a wall next to her desk. Once she got the hang of the camera, I told her that I wanted a few pictures in my full suit and then with my jacket off to start off with and she agreed that would be nice for a online profile.
Once she started taking a few pictures with me with my full suit on, she then told me it was time to take the jacket off which I did. She then took a few more shots which I thought that would be good enough for the photos I wanted in a suit but then she told me to lose the tie and unbutton my collar buttons. I thought this was a good idea, a little more casual but professional looking photo as she snapped away.