Special Home Delivery

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.

"Is there something on your mind Mrs. Vandenberg?" She just stood there, staring at Jackson's growing bulge, trying to decide if she was going to let her lust overwhelm her. Jackson was taunting her to come over and touch his cock.

Mrs. Vandenberg took the bait and seductively walked over to Jackson, caressed his face, giving him a deep tongue kiss while pushing her mature tits up against his chest. Jackson knew he had her where he wanted her.

He reached over to the counter and picked up one of the fresh cucumbers and brought it up to her face and told her, "Suck on this for me Mrs. Vandenberg".

Mrs. Vandenberg erotically licked the cucumber from one end to the other as Jackson held it up to her mouth. He was mezmerized at how deep she could take the thick fat vegetable as he pumped it into her throat. He knew she was ready.

Jackson decided to take a chance that Mrs. Vandenberg liked it rough. He grabbed both sides of her white sheer blouse and ripped it wide-open. He could hear the sound of the buttons hitting and rolling across the kitchen floor while exposing Mrs. Vandenberg's nice black lace push-up bra supporting her large, mature,well tanned tits. She threw her head back in ecstasy enjoying the feel of the young man's hands, massaging her breasts through her bra.

He insulted her by telling her "Get down on your knees Ma'am and suck my cock." Mrs. Vandenberg realized she was a victim of her own lust.

Mrs. Vandenberg struggled in her high heels and short skirt to get down on her knees. Jackson reached down and unhooked and removed her bra. He wanted to watch her

mature, hanging milkers as she sucked his teenage cock? She unzipped and unbottoned Jackson's pants and pulled out his cock and said, "Holy shit" as Jackson grabbed the cucumber and laid it next to his cock for a comparison.

Mrs. Vandenberg was stunned but also turned on that Jackson's cock was as big and as thick as the cucumber. She immediately went to work on his cock and balls as only a sex starved mature wealthy white woman can do. Jackson, loved the sight of his large cock laying on Mrs. Vandenberg's face as she licked and popped his balls in and out of her mouth as if they were a large gumball.

Jackson stood with his hands on his hips, leaning against the kitchen countertop looking down admiring Mrs. Vandenberg sucking his hanging teenage balls and licking his cock from tip to base.

He wanted her mature pussy. He pulled Mrs. Vandenberg to her feet and walked her into the living room, still wearing her skirt and her high heels. Jackson took a seat while stroking his hard cock and instructed Mrs. Vandenberg, "Strip for me Ma'am, but leave your shoes on."

Mrs. Vandenberg liked being controlled and dominated. She started to slowly sway her hips back-and-forth as she reached behind her back to unzip her khaki colored skirt and let it fall to the floor. She stepped out of the skirt and walked towards Jackson wearing only her high heels and her black lace panties that matched her bra.

Jackson spread his knees, inviting Mrs. Vandenberg to come step closer so he could bury his face in her pussy. Jackson teased Mrs. Vandenberg by kissing her belly button and licking his way down to her panty line. He slipped his fingers under both sides of her panties and aggressively ripped them off of her mature torso. She moaned and squealed in excitement being manhandled by the young stud who was young enough to be her son.

Mrs. Vandenberg now stood before Jackson's face with her mature, shaved pussy, ready to be assulted by young tongue and cock. Jackson was very strong and in great shape and picked up Mrs. Vandenberg with ease and carried her down the hallway to her marital bedroom.

Jackson enjoyed the feel of a vulnerable naked, mature woman in his arms. Mrs. Vandenberg was almost in a trance, knowing she was about to be fucked by a teenage boy in her own marital bed.

Jackson laid her down on the bed with her head hanging over the edge of the bed with his cock and balls hanging in her face before he fucked her. She wanted to be fucked hard and he knew it. When she was ready, he laid on top of her, forcing her knees apart pushing the head of his cock up against her willing pussy. He was going to give it to her hard and fast not knowing if her husband would be returning for lunch.

Jackson hovered over her in a four-point push-up position, listening to Mrs. Vandenberg squeal as he started to penetrate her and began to relentlessly slam fuck her into the mattress with her high-heeled shoes, waving in the air.

Mrs. Vandenberg grabbed Jackson's ass cheeks with both hands, pulling him deep into her as she ground her pussy against his cock moaning and almost speaking in tongues with every thrust. Jackson knew his time was limited. It was time to unload his balls and give Mrs. Vandenberand his full load get the hell out of there.

He did not dare cum in her mature, still fertile pussy. He pulled out and knelt between her tan thighs while aggressively jerking ropes of jizz shamelessly covering Mrs. Vandenberg from her tits down to her pussy.

However, before he got dressed Jachson had one more thing he wanted to do to Mrs. Vandenberg. Jackson walked stark naked out to the kitchen and returned to the bedroom with one of Mrs. Vandenberg cucumbers. He slowly rubbed the cucumber over Mrs. Vandenberg's swollen clit before he worked it halfway into her mature pussy. It didn't take long for Mrs. Vandenberg to moan and grunt in a shattering orgasm, squirting her pussy juice all over the cucumber.

Jackson looked her in the eye and told her, "Make sure you serve this to your husband tonight." As he was leaving, Mrs. Brandenburg said she would be placing another order next week and expected him to deliver it.

Jackson was backing out of the driveway just as Mr. Vanderburg was returning home for lunch. Jackson and Mr. Vandenberg exchanged a pleasant smile and a wave with Mrs. Vandenberg's torn panties dangling out of Jackson's shirt pocket. Jackson was pleased with himself, knowing that he had just banged this old dude's wife and jacked her off with a 10 inch cucumber that Mr. V. would be eating for dinner later that night.

Jackson would always take a woman's panties as a souvenir of his conquest. He would proudly share his target's panties with the rest of us box boys when he returned to the store. It was his way of showing off and letting the rest of us know he had successfully scored with another mature, milf customer.

After working at the store for a couple months, I was beginning to to get more comfortable with mature women by following Jackson's routine. One day, Jackson and I were talking in the store as an attractive mature woman in her 40s entered the store.

She was wearing tight jeans, a low-cut top showing a lot of cleavage, hair pulled back in a ponytail and high heel boots. She perfectly fit the profile of Jackson's second type of milf mom that he loved to fuck. Jackson was a generous guy so he looked at me and he said "she's all yours kid."

After letting her shop for a few minutes, I found her in one of the aisles and approached her using Jackson's opening line. "Excuse me Miss, are you finding everything you need." I caught her by surprise as she started to say, "No thanks I'm doing just fine." She turned around and saw me and stopped in midsentence and said, "Well, I could use some help. Could you show me to the produce section."

We had some comfortable casual conversation as I escorted her to the produce section and I noticed she had a small sexy gap between her two front teeth. She introduced herself as Erica and said she usually shops at the store once a week when her husband was out of town.

My ears perked up as Erica worked her way through the variety of vegetables ending up with a large cucumber in her hand. She asked me, "Do you think this will be big enough young man?" I sarcastically responded, "Well I guess it depends on what you're going to use it for." She laughed and said, "Yeah, this one looks just about right."

I was about to bust my nut right there in the aisle convinced this MILF slut was messing with my head. I told her I would meet her when she checked out and help her out to her car with her groceries. She said, "Thank you, I look forward to it.

We continued some nice conversation on our way to her car. Her blouse slightly rose up as we were loading the groceries into the back of her car. I could see she had a small tattoo on her lower back and a strip of her purple thong was showing above her jeans. She was a perfect vision of a mature, white trash slut.

Honest to god I wanted to bend her over and force fuck her right there in the parking lot. However, I stayed with the plan and let her know that home deliveries were my specialty and that she needed to make sure she asks for Tommy when she placed her orders. She gave me a nice $10 tip and a smile as I walked back into the store feeling I needed to go in the restroom and blow a load.

Two days later Erica called the store, placed her order and gave instructions to have me deliver the groceries the next day at noon. She also made it very specific that I needed to come around to the back of the house. As I pulled up the driveway of her very expensive, upscale home, my heart was beating with anticipation.

As instructed I carried her groceries around the back of the house. When I reached the gate I yelled out, "Hello Erica, it's Tommy, I have your groceries." She replied, " The gate is open, come on in."

I was pleasantly surprised to see Erica lounging around the pool wearing a very skimpy black bikini. She was laying on her back in a lounge chair, wearing some very stylish sunglasses, a floppy hat and some sexy cork high healed shoes. She got up out of her lounge chair and escorted me into the house, showing me where to place the groceries in the kitchen.

While Erica was putting away the groceries, I could see that the tattoo on her lower back was a scorpion. Clearly, a total tramp stamp. I complimented her on what a beautiful tattoo it was and she smiled and said, "Thank you, I am very proud of it. Would you like to get a closer look."

With that, she put her arms on the countertop, leaned forward, sticking her ass up in the air. I was not going to be shy. I leaned over with my face inches from her ass, close enough to smell her suntan lotion, mixed with her erotic perfume. The tease was on.

I stammered and responded something like, "Wow, that is really nice Erica. Does your husband like it?" I was somewhat embarrassed that I had the balls to ask her that question. I had no idea how she was going to respond.

Erica surprised me by saying, "Oh yes, my husband Bob loves it, and so do all my lovers. They enjoy looking at it when I'm on my knees." All I could do was chuckle now realizing she was totally fucking with me.

My cock immediately started to grow knowing this mature trashy MILF was seducing me. I thought to myself, "what would Jackson do in this situation?"

I did not hesitate for one second. I immediately asked her, "Is that your only tattoo Erica?" She turned around and leaned back against the countertop and asked me, "How old are you young man?" I responded by telling her I was 18 years old. With that she smiled and reached down and slightly lowered her bikini bottom, revealing a small peach tatoo just below her bikini line.

Once again, Erica asked me, "Young man would you like to get a closer look?" Once again, I did not hesitate for one second. I dropped down to one knee and put my face so close that I could see the small blonde hairs glistening on her belly just above her bikini line.

Now Erica had me right where she wanted me.

Erica slowly pulled the strings on both sides of her bikini bottom and let it drop to the floor. I was now staring at the most beautiful, mature pussy I've ever seen with a small landing strip above her pussy lips.

Erica challenged me by saying, "Well young man, what are you gonna do now?"

I didn't have much time to respond before Erica put one hand behind my head and pushed my face into her pussy saying, "Eat me."

As a young man, I didn't have much experience eating pussy, but I went after her like I hadn't had a meal in years. The aroma of her pussy, her perfume, and a suntan lotion, motivated me to alternate, licking and applying slight suction to her clit while I worked my middle finger up into her tight, wet pussy.

Erica then put both her hands on my head and started to tremble knowing she had an orgasm that was fast approaching. She let loose a twitching, moaning groaning orgasm, shooting pussy juice on my face and the front of my work shirt. I was stunned, having never seen a woman squirt before.

I stood up and pinned Erica against the countertop kissing her and pulling the strings on her bikini top. Her large, 40 plus year old hanging tits sprang to life allowing me to grab squeeze and suck on her nipples. Erica was standing in front of me, only wearing her cork heel shoes as she reached down and placed her hand on my cock. I was about to get my first blow job from mature slut wife Erica.