My job at Canadian Tire just wasn't paying enough anymore and after a few weeks of looking I finally found another job with more pay. Ever since my hot and horny meetings with Greta the sexy older waitress I've made a conscious effort to go out of my way to be as sweet as a peach pie to all older women. For some reason I had the best luck when I chatted up waitresses. I found that waitresses not only collect tips but they can also be pretty big tippers themselves!
For example, take a 49 year old honey named Tina. She worked with me in the downtown Toronto nightclub where I had been working for about a year. I was the doorman or bouncer and Tina was hired to help out during the bust late night shift. There was only one problem, Tina was clueless and had no idea what was expected of her. She had just recently gotten divorced and had never worked a day in her life.
Tina was 26 years older than I was at the time but when she got flustered, upset or confused she acted and looked like a teenager. I tried my best to help her out as much as I could. I even covered up for her if she screwed up. And believe me I didn't mind. In fact I would have done anything to get into her pants.
She had a super sexy body, she looked much younger than her age and I made sure I told her how great she looked every chance I got. I made sure she'd catch me sneaking peeks or gawking at her boobs so that she knew I had the hots for her. I knew she wasn't getting laid at home since the divorce and she told me she wasn't seeing anyone while we talked one day. I wanted her to know that if she ever got horny or had the urge that she could count on me to help her out.
Eventually, I got my chance to do just that but not before some hesitation on Tina's part. She wasn't sure that it was a good idea for her to be getting involved with a younger man, a man less than half her age, so initially the sex happened in rational dribs and drabs.