This one is a bit different from my first series. This is about a young man that has some adventures with a few hot 30-40 something women. Please let me know what you think!
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Tim was quietly playing Xbox in his room, as he always did on a Saturday morning, when his mother knocked on his door. It was unexpected as she was usually out shopping at this time.
"Tim love, I want you to help your neighbour Ms. Hardaway with something now. She asked me if you would help her with a sales presentation," his Mother said after opening the door. She would always just enter after knocking, never waiting for a response. Luckily, Tim was not the normal kind of 18-year-old boy. He never masturbated, it was like hadn't occurred to him or he had any interest. He was really into video games and fantasy games like D&D.
"But, I really don't want to go there can't I," Tim said as he was interrupted.
"No buts! Tim, if you ever want to get a girlfriend, I know you are shy, I was too at your age, you need to start learning how to interact with women... who aren't your mother or sisters!" She said.
"Ugghh... can I at least finish this level?" He pleaded.
"Yes ok, but then I want you to have a shower and put on the new jeans I got you and the blue long sleeve shirt then head over to Ms. Hardaway's house. She said her thing starts at 10am. Don't keep a woman waiting!"
"Yeah ok..." Tim replied. He finished up his game in a few minutes then got in the shower. As his mother had mentioned, Tim was shy. This might have been because he was quite short at 5'4". He had mousey brown hair that was trimmed to a few inches. He had small features and a medium but toned frame. He wasn't very muscular like the jocks, so he would always avoid any confrontations with them. Tim finished his shower got dressed, kissed his mother on the cheek and walked to the house next door. Tim inhaled sharply contemplating the eminent meeting with Ms. Hardaway, then knocked weakly on the door. Maybe he was hoping she wouldn't hear and he could go back home. No such luck, a moment later Ms. Hardaway opened the door and smiled broadly at Tim.
"Hello Timmy! Are you here to help me with my sales presentation?" She said with a melodious voice.
"Er.. y-yeah," Tim said almost jumping when she spoke. Ms. Hardaway was 40 years old and absolutely stunning. She was statuesque and voluptuous. She had long brown wavy hair framing a light olive complexion with a slim oval face with big almond eyes, full lips and straight teeth. Below that she had a large cantaloupe sized breasts that were push up and together to make a deep cleavage behind her plunging V-neck summer dress in yellow with a white flower pattern that ended 8 inches below her full round ass. Speaking of legs, Ms. Hardaway's legs were long and shapely her calves accentuated their length. But maybe the most remarkable thing about her was that she was 6' tall, towering over Tim.
"Thank you so much! You are a lifesaver!" she said as she grabbed him in an unexpected hug, pulling his face into her deep cleavage. Tim was shocked upon feeling the warm globes smother his face, he put his arms out to the side not knowing what to do. He felt a few butterflies in his stomach, and maybe a tingle somewhere below that.
"Well, come in then, take off your shoes and socks first," she said.
"Yes, sorry, ok," Tim said not sure why he apologized as he had done nothing wrong.
He removed his size 11s and socks and placed them in the shoe rack beside the door and walked inside.
"Take a seat, I'm just getting all my products together. Would you like a tea, coffee, water? Something stronger?"
"Uhm, just a coffee thanks Ms. Hardaway."
"No need to be so formal Timmy, please call me Kendra."
"Ok Ms- uhm Kendra."
Tim surveyed the room. He could see a bookshelf full of books with titles such as "The Female Eunuch", "The Bell Jar", "Venus in Furs" and "The art of sensual female dominance". He wasn't sure what they were about, the last one sounded strange to him. The lounge room was well appointed with two long sofas and two recliners. Just then Kendra came back with the coffees.
"Here you are," she said setting the coffees on the table, "So, I don't know what your mother told you, what I'm doing today is an introduction to a few products, like bed clothing for men and a few other things I'll talk about later. Hopefully the friends I have invited will like to buy them for their husbands or boyfriends," she said.
"Oh, ok I see. So how can I help Kendra?" Tim asked.
"Well, I'd like you to model the clothes for us. Don't worry, it's nothing that you wouldn't wear yourself," she said, "It's just always best to see the clothes on a model."
"Ahh.. uhm, well i-it's just I have never done anything like this, I don't want to mess it up," he said.
"Don't worry, you will be great! Just be confident. Your mother told me I might need to give you a little push to get out of your comfort zone. She told me that you need to talk to more women, sorry I don't mean to embarrass you."
"Oh ahm its ok. Yes my mother is right I know," Tim conceded.
"Oh she also told me that you are to listen to me as you would her," Kendra said.
Tim sighed, "Ok Ms. Har- er Kendra."
"Good boy," Kendra said as she kissed him on the cheek. Tim blushed, he'd never been kissed, even on the cheek, by a girl, let alone one as hot as Kendra.
"Ok well the girls should be here soon, so just relax."
"Yes, thank you Kendra."
Kendra went about setting up her product displays, some boxes she didn't open but just moved to the side of the coffee table. Pajama sets on clothes hangers were hanging on a small clothes horse and some boxer briefs were arranged on the table. Tim felt nervous looking at the boxers. He hoped he wouldn't have to wear them. He thought to himself, "what have I gotten myself in for?", he was beginning to regret letting his mother tell him to do this. After 10 minutes he had finished his coffee and heard a knock at the door.
"Be a dear and let answer the door," Kendra said. Tim noted she had said please for anything she asked of him. He thought it was a bit rude but he wasn't upset by it. He felt as though he wanted to do what she asked, maybe because she was so beautiful, tall and had a vivacious personality. Tim opened the door to see three women who looked to be between the ages of 30 and 40.
"Oh hello, is Kendra here?" Val, the shortest one at 5'8", still towering over Tim, asked.
"Yes, she is, ah, getting ready for you," Tim said.
"Can we come in, or do you want to see our ID?" the petite redhead, Jane, said.
Tim laughed nervously, "ahh no, I mean, yes please come in- oh Kendra said to take off your shoes!"
