It all began by chance, seeing some things he wasn’t supposed to, then driven by curiosity and hormonally clouded judgement, he saw more. Then by design and persistence, eventurally Tommy discovered the secret his mother was keeping from everyone.
By the time Tommy was turning seventeen, his libido was in full command of most of his decisions in life. He was driving, dating, partying with friends, and becoming a young man. He was tall and stocky like his father, almost six feet and naturally a member of the high school varsity football team. With his looks and status in sports, there was no shortage of girls that wanted to explore they're budding sexuality with him.
And as a responsible young man, he always told them they needed to wait until they were older to have sex... NOT!
He had a reputation. The team knew, the girls knew, and most likely the teachers and his coaches knew, he was a player, on and off the field. Through his junior year he had dated or hooked up at a party with all of the who's who of popular girls in his high school and even some from nearby schools. The boxes of condoms he would go through in a couple weekends was surprising!
Despite all of the attention and encounters he had with the hottest of cheerleaders, girls most guys would never even get a chance with and only fantasized about, he was getting bored with them and wanted something more.
As Tommy's sexual experience grew, he began to have an interest for more mature and classy women. He found himself drawn to gawk and fantasize about his female teachers, dressed in skirts and heels and button-up blouses or conservative dresses with a hint of sexiness. Stealing peeks under their desks as they would sit and cross their legs, admiring the curves of their ass under a form-fitting skirt as they wrote on the board, standing over them at their desk to look down their blouses as he pretended to care about a question on a quiz, or maybe getting just the right angle from below as he followed them up the stairs.
He would stare and imagine undressing and touching professional women he would encounter or the mature saleswoman working in the mall. Probably because these women typically held positions of importance or authority to him, his fantasies often revolved around them being submissive to him, needing to please him and willingly do anything he desired.
His biggest influence, and most likely the reason behind his fetish for the mature professional look, was his mother, Elizabeth. As long as he could remember she was a professional in sales and always dressed to impress; high heels, short skirts or dresses, low cut or borderline sheer tops, stockings and nylons. Often lingerie that would be reserved for most women’s special occasions were everyday-wear for her. And with the natural hormonal teen urges and lack of impulse control, he was more familiar with her wardrobe and intimate items in her closet than she was.
He was watching porn on the internet a lot. He loved the videos with mature women. The ones themed with secretaries, teachers, flight attendants, librarians, all the cliches of mature women in high heels and stockings and classy dresses or uniforms. Unless there was some special function at school, the girls his age were all in sneakers and leggings and maybe the occasional mini skirt, but just didn't have that look that he fantasized about.
The other thing that he was drawn to, the thing that gave him that intense nervous excitement in his gut, were the videos where the women looked and acted so confident and powerful but then when confronted by a strong man, or a few, became reluctantly submissive and did anything they were asked.
It was spring, he just turned seventeen. Over the past year his mom had become one of his common sources of inspiration and occasional eye candy. To her he was just her son, the one she had to clean up after and cooked for. She never even thought to look at him in any other way, so she clearly never thought he would be looking at her any differently, but he was.
Because she didn't think of him as a sexual man, her guard was down around him. Sitting or laying on the couch, she would not even pay attention to how high her skirt had ridden or how the wrap of her dress had fallen open. The glimpse of her stocking top, her panties on display, or sometimes laying with the top she was wearing gaped open to expose her breast and nipple. No second thought really given to the sheer skimpy nightgown she would wear in the kitchen in the morning as she made her coffee. Not realizing how the cheeks of her cute ass would peek out the bottom hem, sometimes even the lips of her beautifully smooth shaved pussy peeking from between her legs when she would bend forward to pick something up. Curve hugging leggings, see through tight tops with no bra, nipples clearly visible. Even the occasional streak through the kitchen in her bra, high heels and pantyhose to get her dress from the laundry.
These were the types of teases he would get on any given day, and they would trigger his erection and need to masturbate to the images in his mind.
But recently, he had noticed something seemed different with her. He couldn't quite figure it out or understand, but she seemed like something was weighing on her, and in a strange way he felt like it was something sexual she was dealing with.
He noticed, if it was even possible, some days what she wore to work was even more sexy than normal for her. Things like her high heels were always the highest, sometimes you could clearly tell she wasn't wearing a bra, and on several occasions he caught the glimpse of stockings with garters. There were even a couple times that he noticed when she got home, she looked like her hair was messed up or her lipstick was smeared.
Many days he would get home from school long before his mom and step dad got home from work. Some days when he would be especially worked up, he would explore his mom's closet, looking for her intimate secrets. He was familiar with all of her hosiery. She had great legs and loved to show them, so there was no shortage of stockings and garter belts, thigh highs, and sheer pantyhose in every color and a variety of patterns. Those were just her everyday items. She also had fishnets and body stockings, many crotchless. On several occasions he stood there running the sheer material of one of her stockings over his cock.
There were no granny panties to be found. There may have only been three or four pairs of bikini panties, the rest were all thongs or g-strings in every color. Some were lace, some were sheer, some tied at the hips. Some particular pairs caught his attention because they were so incredibly skimpy, just three strings with a tiny triangle of material in the front.
He would look at her dresses, feel the material, imagine what it would feel like rubbing on her body. He would open them up to see how they tied or zipped or buttoned.
He looked at the wall of shoes to the right, 99% of them some type of high heel. Open toe, pumps, slingbacks, sandals, wedges, in all colors and patterns but all sharing a heel no less than three and a half or four inches high.
All of this gave him fuel as he would have his pants open stroking himself as he went through her intimate apparel. But the thing he always saved for last, the shoe box he discovered strategically buried in the corner under some coats, was the holy grail at the time he found it. Even though he knew every item in it, his hands still shook as he opened it because it revealed the side of his mother that was hidden from him.
He took the lid off and inside was an assortment of sexual secrets. There were three different dildos, all molded to look and feel real, one was about five inches long, another almost eight with a suction cup on the bottom, but the third one was his favorite to imagine her using. It had a suction cup base and split into two dildos, one slightly smaller than the other. If he would have found that when he was younger, he probably would have naively asked ‘why are there two?’ But now, after many experiences making his girlfriends cry out as he took their anal cherry, he knew exactly how this one worked. The thing that excited him so much was thinking that she used that and did it to herself. She liked that. He would sit there looking at it and stroking his cock, imagining that she probably stuck it to the bathtub and would straddle it, riding it to make herself come.
There was a half full bottle of lube, that he noticed was replaced often, which told him these toys got a lot of use. There were small vibrators, metal balls that he had to look up on the internet to find out what they were, and even a pair of nipple clamps. In the bottom was a pair of handcuffs and a blindfold with red lips printed all over it. Finally, a couple of letters from a long time ago between her and his biological dad. Mostly mushy stuff, but a couple references to giving blowjobs and tying her up.
Every time he would open the box he would make a mental note of exactly how everything was placed, so the next time he looked he would know if anything had been used. And never fail, vibrators and dildos would be in different positions. Sometimes even still wet from where she washed them off after using them last.
Tommy had a job with a local landscape company that he was planning to work full time in the summer, but for now he was just working weekends until school was finished. It was at one of those weekend jobs that he had an experience that cemented his fetishes and emboldened him. He felt like it was the day he became a man.
He and another guy were scheduled to work at this rich guy's house, just cleaning up the yard and freshening up the mulch for spring. He got there at 8:00 AM and met the owner of the company who was delivering the dump truck load of mulch and dumped it in front of the house. The owner told him the guy that was supposed to help him called off sick so he would have to take care of this job by himself. He told him he'd give him a few extra bucks since he knew it was a lot of work and he left.
Tommy was bitching and moaning to himself as he was wheelbarrowing mulch around the house and as he came back to the front, a gray Mercedes pulled up to the garage and parked. He was stopped in his tracks as the door swung open and a pair of gorgeous legs with tan high heels, wrapped in tan nylons, swung out of the car. It was a blonde woman, maybe around 40, in a beige button-up dress that was hiked up high and open enough to expose the tops of her tan nylons as she got out.
She paused also and smiled as she spotted the young man watching her, and then proceeded to do her best to put on a show as she leaned into the backseat of her car to gather a few bags, again her dress riding up and revealing the tops of her nylons.
Tommy walked over to introduce himself and offered to help her carry the bags into the house. Her name was Susan and she was the wife of the owner of the house. She was very appreciative of his offer and handed him a few bags and headed up the walk. He followed a few feet behind her watching her hips sway as she walked and climbed the steps to the front door. She peeked back over her shoulder as she walked up the steps, an experienced woman who knew when she was being checked out, enjoyed the attention of this handsome young man.
After some small talk, awkward flirting and mild innuendos, Tommy headed back out to his job in the yard. As he worked, he couldn't get the image of her legs out of his mind. An hour had gone by and the sun was beating down now so he had his shirt off as he was shoveling and wheeling the mulch around the house. He wasn't completely naive either. He noticed Susan in different windows around the house as he worked, watching him. When he came back to the front, she came down off of the porch carrying a cold glass of ice water for him. He immediately noticed as she came down the steps that a few more buttons on the front of her dress were open. The tops of her nylons were visible now with every step she took, and the inner curve of her cleavage was exposed.
She stood there and complimented him on the job he was doing as he guzzled down the glass of ice water. Her hand delicately traced over his shoulder and down the back of his arm and back up again.
