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Chapter 13
by wilparu
Will Aiden accept?
YES - The Stockyards Market
-Erin-
“I… tonight?" Poor Aiden was shocked. Almost as much as Erin was. Well, hopefully, he declines gracefully, no need to make it awkward for this Jennifer woman, she doesn’t seem so bad-
“That, uh, would be f-fun?” The woman’s confident smile grew even more so as Aiden’s eyes widened slightly as if he could not quite believe what he had said either. He shifted in his chair and took a breath, but if he intended to continue with a less positive statement he never got the chance.
“Wonderful! You are making me extremely happy, Aiden!” Jennifer mimed wiping a bead of sweat off her brow, “Here is my card, let me grab that pen there honey, thanks, OK I’m just writing my private cell phone number on the back. Please, call me after work, or text me, I don’t want to get you in trouble for slacking!”
In a daze, Aiden watched as the woman jotted a few words under the phone number she had given him. “Now, for you, I am available any time tonight, or even earlier. The artist's market goes all afternoon until late, so no need to wait until it gets dark. Do you live in a rooming house? On your own? I’ll pick you up in my car, wait for you outside, then off we go.
Erin realized she was staring rudely at Aiden when Jennifer Cardinal turned her head to look at her again. Her voice pitched to the young man’s coworker, she said, “I understand it’s a sudden request, Aiden. You’re truly making my entire week - no, my month! - by agreeing to visit the market with me. I assure you my intentions are honourable, I’m not a scumbag woman with a husband and kids tucked away while I play the field or anything. You are a very handsome boy - sorry, young man - but I just want to get to know you, no strings.”
Swallowing down a sour taste, Erin gave the woman in the expensive cream suit a stiff nod as she turned toward the stairs. ‘Not my business, good for the lad I guess’, she thought. ‘That woman is clearly pretty experienced but didn’t seem rapey at all… a bit forward, but anyone who built her own company like that is bound to be assertive. I didn’t think Aiden would fall for the first rich woman who flashed her cash at him like that though, he seemed like such a proper, good boy.’
That thought, even as it forms, grabs Erin’s attention. Halfway up the steps, here she is stomping away with a huge frown like someone did her wrong. What the hell, that’s the cavewoman shit she calls out from her Mom and sister, and now she is acting like Aiden is not capable of being his own person with his own valid desires and agency.
By the time she is back in her office, Erin has resolved to give it no more thought. Let Aiden live his life as a young man in the big city, she has no right to judge him for anything, it’s just the bone-deep toxic femininity that permeates society as a whole. You gotta recognize when the role models you had growing up, whether it was movies and TV or your horndog Mother who still brags about all the boys she deflowered while at uni, have conditioned you to think of men as lesser somehow. As if they owe you attention and respect, even romantic interest and sex.
Nope. Not Erin. As she starts banging away at her keyboard with some extra percussive **** she glares at the spreadsheet in front of her and resolves, once more, to forget all about Aiden’s personal life.
-Aiden-
“Didn’t I say?” Jennifer Cardinal held her hand out in an airy gesture, as if she had conjured it all from thin air.
“Oh… wow.” Aiden, his nerves still jangling, looked down the alleyway and gave a happy laugh. “This is so cool!”
A hundred and fifty-odd years ago this area had been a few ranches and stockyards near the river but outside the city proper; the city quickly grew around it and replaced the cows with brick warehouses and small factories by the 1930s but the area retained the ‘Stockyards’ name. After a half-century of benign neglect almost inevitably the warehouses and half-empty stone merchant buildings became affordable studio space for artists and then a hip area where condos mixed in with artist co-ops, popular night clubs, and chic restaurants.
The long cobblestone alley behind one of the largest art galleries was now full of temporary stalls and crowded with a few hundred people. Most of the outdoor market spots were for small local merchants, craft breweries, home bakeries and artists eager to sell their wares to the urbane shoppers.
Aiden wasn’t sure he had ever seen anything so exciting and vibrant in his entire life.
Jennifer gave a happy grin at his genuine excitement. She was dressed as she had been earlier, in a perfectly tailored off-white suit, matching jewelry at wrist and ankle and a small designer handbag. With her long, straight black hair, mid-part and flowing down her back, her light brown skin and proud facial features she was every inch the wealthy, successful woman.
When he had returned to his tiny apartment, still half in disbelief, Aiden had hurriedly washed up and changed his baggy long-sleeve sweatshirt to a, well, a different baggy long-sleeve shirt. But this one was at least a marginally thinner material, so slightly less frumpy and unfashionable. He hoped.
True to her word, Jennifer had been standing beside her car in front of his building at the arranged time. Aiden didn’t know much about cars, but he knew enough to recognize an extremely expensive sports car when he saw one. The bright yellow machine was low to the ground, like a jungle cat on the prowl, and it stuck out in his gritty neighbourhood like a sore thumb.
And yet, even on a street full of cheap tenements and boarding houses, Jennifer Cardinal stood with the casual ease of someone who felt she belonged anywhere and everywhere. She might be getting second - and third - looks from the locals, but she had eyes only for Aiden.
The realization that she was there to pick him up, that this rich, gorgeous, powerful, woman was looking at him with happy eyes and a welcoming smile, shook Aiden to his core. He could barely believe it.
… and the realization triggered a tiny flicker in his belly. A sense of almost pride that someone like her would be interested in any way in a poor, miserable, ugly boy from a shitty, dying town.
And now, here in the alleyway, Aiden could still feel that doubt flaring up, and yet it wasn’t overwhelming. It wasn’t making him shut down or run away as he had half expected. He simply wasn’t as afraid as he would have assumed he would be. Like anyone who knew him back home would have assumed.
“Ahh, look at this Aiden,” Jennifer herded him to the nearest stall where a pair of carefully dressed men stood at attention before a riot of colourful clothing. “This is some very fashionable menswear. I’m not an expert myself, but these are super cute I think.”
The clothes were indeed quite stylish, even Aiden could see that. Short sleeves abounded, of course, and some of the tops were practically little vests. Surely, you would only wear that with an undershirt, your entire arms and some of your chest and stomach would be showing in that! And yet, the colours and fabrics were almost hypnotic, and Aiden let out a quiet sigh as he ran his hand down one shirt, a double-breasted piece of a deep green fabric that felt soft as a cloud. It featured shorter sleeves but not quite as scandalously short as some, and it was cut to fall to your belly button. Only extremely beautiful boys with no shame could wear something like this!
He could never wear something so fine, or so overtly, well, sexy. A small tag had a handwritten price of $250 on it, which made him almost giggle at the absurdity of having one piece of clothing, a top you could only wear at a fancy party or some expensive restaurant, that cost almost a full month's rent.
“Do you like that one?”
Guiltily, Aiden put it back and laughed, “No no! Well, yeah, it’s gorgeous,” he looked earnestly at the man behind the small table, “It’s just not er, for me.”
The owner of the boutique kept his eyes on Jennifer, his face bland. The woman turned to him and nodded, “I’ll take it. And over there, that rack of men's slacks? What colour would you suggest for Aiden here?”
“W-w-wait, what?” Aiden stammered.
Jennifer gave him a quick smile but kept speaking to the shop owner. “In fact, can you pick out one of those nice undershirts from there? Yes, something to match this lovely green collared shirt, and the pants too.”
“Oh no, Jennifer-“
She held up a hand, but it was her smile that stopped him. “No Aiden, I am buying this for me. Do not worry about the price, at all, I sure am not. I am going to let this lovely craftsman pick out a few pieces of brilliant fashionable clothing and if you want it you can have it. And like I said, no obligations and no expectations. I have the means, and I want to treat you, but you do not have to accept if you don’t want to. But I am buying it!”
The shop owner was rapidly pulling out some shirts (an undershirt that cost $70!!) and holding them to some sleek men’s trousers, quickly determining the best match while giving Aiden a solid once over to note his colouring and size.
He wanted to insist, he wanted to say no, he really really did. The clothes were beyond amazing, and even ignoring the shocking prices Aiden knew in his soul that he would look absurd in such pretty things, a disgustingly plain boy like him. He had to put his foot down and deny this insane gift!
But the vendor had already bagged not only the green top, light grey pants, and slinky undershirt but had included a few other items as Jennifer casually pointed. She handed over a card without even asking about the total, and Aiden could only stare.
Back home, they knew what kind of boy let a rich woman buy him things like this. Even worse than the sluts who would let any girl who smiled at them touch their privates were the whores, the boys who sold their Goddess-given chastity for money and favours. That didn’t feel like what Jennifer was doing, not really, she was so nice and generous and had made it clear she had no expectations for a ‘favour’ in return. She just seemed excited to share the experience of the market with a new friend.
But Aiden knew what the old fire and brimstone preacher back home would say. With her waist long unbound and uncut grey hair flying as she yelled and slammed the Good Book down on her pulpit, pointing accusing fingers at all the men and boys who would tempt honest Christian women astray.
The same preacher who had asked Aiden, point blank, what he did in school to get in trouble like that. Who simply glared at him when he protested his innocence, when he dared tell her he had done nothing.
“I…” Aiden licked his lips when she turned back to him, her expression assured and serene.
“Thank you, Jennifer. It’s, uh, way way too generous, and I really shouldn’t. But… thanks.”
Her smile was like lightning out of a clear blue sky.
What's next?
The Fairer Sex
A world of strict gender roles, reversed
Explore a world where the roles of each gender are still strictly enforced though societal and social pressures, only they are the opposites of those we know. Women are expected to take the lead in almost every situation, with the men in their lives as meek followers, and scorn and mockery awaits anyone who steps outside these boundaries of good behavior. This is clearest of course in the world of romance.
- Tags
- Mother, Mother-son, Discipline, Bondage, Spanking, Femdom, Training, Alternate Universe, Gender Role Swap, Crossdressing, Personality Change, threesome, femboy, Proposal, Romance, Pussyjob, Humping, Female Supremacy, Male Sub, Gender Roles, Marriage, Cuckquean, Pegging, Love, Cum eating, spank, pretend couple, interracial, Outercourse, mommy, CFNM, Nursing Handjob, Gentle Femdom, Wife, Boobs, Handjob, father, daughter, panty sniffing, Striptease, Punishment, Fdom, Domestic Discipline, Comfort, Tears, Househusband, 1950s, Mommydomme, MILF, Doctor, Nudity, Choosing, Older Sister, Amazon Position, Riding, Rough, Muscles, Amazon, Workplace, Stripping, Domination
Updated on Jun 13, 2025
by Conan The Librarian
Created on Aug 13, 2020
by Haoro
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