I think I can speak for a lot of young American males that growing up as a young man our first real paying job in high school was working at a grocery store as a box boy.
Our high school football coach happened to have a relationship with a local grocery store owner who would hire some of us players as box boys for after school and weekend work to not only keep us out of trouble, but also to earn some extra cash. We were all 18 years of age in our senior year of high school. We were all very motivated young guys in the best shape of our lives.
Working as a box boy taught me real life skills that I would use later on in my sales career such as learning to work for a boss, consistently showing up on time, learning to work with other employees, as well as working with customers.
Another skill I learned as a box boy that rewarded me very well later on in my life was learning to read and be comfortable and convincing when talking to adults. Especially mature adult women. To be more specific, talking to MILFS.
I started working at the relatively high-end grocery store in an upscale, southern California suburb in my senior year. My work hours would generally be after school for a couple hours during the week and occasionally working weekends. One observation that immediately struck me like a bolt of lighting was that most of the customers shopping in the store were women.
Women of all shapes and sizes from all walks of life. Housewives, professional women, white-collar women, blue collar women, nurses, teachers, personal trainers, Pilates instructors, white women, Hispanic women, black women women, athletic women, slutty women, wealthy drama queens, and desperate hungry housewives.
It was a potpourri of mature women with an incredible number of MILFs who shopped there including Including my mom, and many of the other players moms.
I wasn't the only one to make this observation. Almost eveyone of my coworkers my age also made the same observation. We were all young, overwhelmed with hormones and jusy looking for opportunities to jack off or better yet, fuck anything we could. These women provided a lot of us with fantasies to jack off over at night after a day of work.
We were also lucky enough to have a supervisor who was one of those guys that seemed way too old and talented to be doing what he was doing, but he continued doing it. We knew it wasn't for the money. We would all later discover that being a box boy had extra benefits. We jokingly referred to him as the Milf Whisperer. His name was Jackson.
Jackson was one of these guys that had the swagger and confidence at a young age who could talk to anybody about anything. He also had an amazing ability to read people and identify the female customers that might have potential for sexual adventure without offending them.
We would also come to find out that Jackson had something else going for him. Jackson was blessed with an extraordinarily large cock and a pair of swinging balls that mature ladies found difficult to resist.
Every day at work, it was as if Jackson was the instructor and we were his students. As women came into the store, he would mentor us and point out which women had potential for sex, and which ones didn't based on the way they dressed, their age, their sexy walk and their body language.
Two types of MILFS always got Jackson's attention. Wealthy upscale, snooty bitches in their 40s and 50s who were totally overdressed for the grocery store or classic milf moms wearing tight clothes, big hair, lots of perfume and showing a lot of cleavage. He loved wealthy socialite women and also loved his women to be a little on the trashy side. He always told us that trashy women were loose and fucked like animals.
Once Jackson identified a potential milf target, he had a routine. He would find them in the aisles while they were shopping and start the conversation by asking her,
" Excuse me Miss, can I help you find something you need?" He explained to us to always address a woman as "Miss" and never as "Ma'am" regardless of their age. Miss inplies youth whereas the word ma'am implies old. That is an important point to remember when you're trying to get into a woman's pants.
Most of the time his targets would respond by saying, "No thank you young man, I'm doing just fine." However, occasionally his target would respond by looking him up and down and saying, "Yes young man, I do need some help." Jackson immediately knew he had a potential target.
Jackson would engage the mature woman in casual conversation while he helped her find the item she was looking for. He could tell right away if she would be open to suggestive conversation and he always let her know that he would meet her at the checkout stand and help her take her groceries out to her car. Bingo.
Once outside the store, Jackson would help her load her groceries in her car so he could check out her ass and maybe get an upskirt peek at her panties if she was wearing a skirt. He would let her know very directly that the store was OK with tipping.
Some women would tip very generously knowing this young man was hitting on them. He would also make sure they knew that he was old enough to do home deliveries, and to make sure they specifically asked for Jackson when they place their orders.
Jackson always prefered to do his deliveries in the morning knowing that most of their boyfriends or husbands would be at work at that time. Jackson was always bragging and telling us stories of his two favorite home delivery customers, Mrs. Vandenberg, and Miss Erica. One day, Jackson told us all about his first home delivery to Mrs. Vanderberg's home.
Mrs. Vandenberg was a classy, upscale milf married to a very wealthy older gentleman. She was a stay at home socialite wife in her late 40s with blonde hair, long tan legs, and big tits and would like to dress provocatively when Jackson arrived with her groceries.
Jackson found out on his first home delivery with Mrs. Vandenberg that she was definetly kinky and wasn't shy about needing cock. Mrs. Vandenberg would play a game of cat and mouse with Jackson by making suggestive comments about the size of the cucumbers, carrots etc, while wearing a low-cut blouse, short skirt and high heels.
Jackson told us could no longer conceal the obvious raging hard cock that was growing in his pants watching sexy Mrs. Vandenberg bending over and reaching over head putting away her groceries. Jackson was smart, he was not going to make the first move on this mature MILF without knowing how she was going to react. The last thing Jackson needed was to have some bitch customer calling the store to get his ass fired.
Jackson leaned back against the kitchen counter, crossed his arms and taunted Mrs. Vandenberg as she started to stare at his very noticible bulge in his pants.
