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Simon couldn’t believe his luck. Finally, a swipe match! I mean, he knew he wasn’t exactly god’s gift to women. He was a dork all his life, as shy as they get, and skinny to a fault. But he had a place and a job – quite the accomplishment for a kid just out of high school. So he was as surprised as he was discouraged when he found 0 matches in two weeks of tinder. In fact, Simon was ready to throw in the towel up until this morning when he got his first match, Nikki. And she was hot too! Blonde, fit, curvy – into comic books, tech, and computers games as well! “Hey there cutie! Wanna go for a cup of coffee? meet me at 02 Overpass Yard,  cincinnaTi, Ohio 452 25.” 

Simon was shaking with excitement as he approached the dive coffee bar. He hadn’t been on a date since freshman year of high school, and that was only because he promised to do her homework for the rest of the year.  His luck was about to change! While he was waiting he kept dwelling on the way she had typed the address, must’ve been a typo.

His excitement turned to joy when Nikki arrived, looking exactly like her profile pic. “Hey! You must be Simon. I’m Nikki, it’s so wonderful to meet you.” Simon opened his mouth but nothing came out, he was completely choked up. “Aww, frog stuck in your throat? Let’s clear it out with a cup of the best coffee in town, my treat” Nikki said with a wink as she approached the register. After a moment she returned with two cups of joe. “You first,” she said as she handed Simon the coffee. Simon brought it up to his mouth and took a sip. It was good, but something about it was off. It tasted somewhat bitter…like a…too much grounds…or somethi…som….

[sometime later]

“Wake up sleepyhead!” Simon opened his eyes to see Nikki’s face staring at him, only it was exaggeratedly big, like 3-4 times bigger than usual. He tried saying something, only to realize he was gagged. When he tried to move he found he couldn’t as his arms and legs were bound. When he looked down, things started to sink in. He was standing on a counter, which meant he must’ve been somewhere between 1-2 feet tall. And that’s not the weirdest part. Somehow, his penis grew. It hung down to his ankles and was wider than both his legs. “I can see things are starting to sink in for you,” Nikki said as Simon began to squirm and mumble through his ball gag. “You see that address – is actually a front for the operation my mom runs – Boytoy Inc. You see, we recruit lonely desperate men like yourself. And sell them off to lonely desperate women – who also happen to be rich!” Nikki said. “Oh don’t give me that look! I gave you a chance with the address. 02 Overpass Yard,  cincinnaTi, Ohio 452 25 – B is the 2nd letter in the alphabet, I capitalized O, Y, T, and O and sectioned off the 25 in the zip code for Y, the 25th letter in the alphabet. That spells Boy Toy - get it!” Nikki giggled as she stood up and clapped in amusement. Simon looked at her in disdain, before hearing a jingle at the door. “Oh, that must be your new owner, Kathy!”

In walked one of the largest women Simon had ever seen. She looked to be in her late forties, or early fifties, with brown hair shoulder length hair with bangs, and somewhat fair skin. She was wearing a tank top and jean shorts. Simon had guessed that she was a good amount over 6 feet tall as her head came close to the top of the doorway when she entered. But she wasn’t just tall, she was quite fat with the biggest rear end he had ever seen. Kathy looked like the type of lady that started out with a huge rear end. Then years of sitting and overeating caused her ass and thighs to balloon out to the elephant butt she sported today. Her hips practically scraped the doorway as she walked in, and her jean shorts strained to cover the entirety of her ass. “Is the little guy ready for me?!” Kathy yelled out

Simon stared in awe as her thighs and ass jiggled with each thunderous step. Either the counter was low, or Kathy was taller than he had thought, as the mammoth woman approached him he found himself staring straight at her meaty cameltoe.

“Oh my gawd he’s perfect!” Kathy guffawed in a harsh NY accent as she reached out to assess her purchase. Her meaty paw gripping the scrawny little Simon as she gripped him around his waist, squeezing his impossibly large dick in-between his legs as she brought him up for inspection. Kathy wasn’t ugly per se, but she certainly looked her age, with frown lines from years of living, to her very fine peach fuzz on her upper lip and chin which only someone as small as Simon and up real close could see. Nothing out of the ordinary, but to a shrunken young man it was jarring. 

“And look at that monster between his legs! I don’t know how you do it but my gawd, it’s not even hard yet?! I kinda want to size him up before I walk out. Can you get him hard for me? I’m so glad I went for the boner control upgrade.” Kathy stated as she handed him to Nikki. Within seconds Nikki had pumped his dick to rock hard before she set him back on the counter. Kathy then turned around and stuck her enormous butt out as Simon’s oversized manhood saluted her. She backed up until her enormous denim-clad cheeks made contact with the tip his dick. Kathy looked over her shoulder and grasped his chest as she began rubbing his manhood up and down her enormous crack.

“Would you look at that, he’s so small I bet he could fit entirely in my asscrack.” Kathy laughed along with Nikki. “Not only that, but he’s so perfectly sized that if I wanted a change of pace I could use half his body for a dildo.” Simon was terrified of the thought of this fat bottomed behemoth over half his age using him as her sex toy, but there was literally nothing he could do.

That night, Kathy rode him hard. She rode him so hard and for so long that Simon was literally imprinted in the ass crater Kathy left behind on the bed. He cringed at the feeling of her full unkempt bush scratching against his entire lower body as the rest of him lay completely flattened under her oppressive ass as she thoroughly herself at his expense, over and over again.  He kept trying to get soft, but he couldn’t. They changed him to the point where he had no control over his penis. No, that was all Kathy’s control. And she took full advantage of this control. She worked him over so hard, so many times that she passed out with him still beneath her. By now it was morning, and he had barely got an ounce of sleep from the oppressive weight and occasional bout of gas, not to mention the snoring. Little did he know that Kathy was about to wake up from a night of full rest, ready to give him another go. Simon whimpered as Kathy began to stir, and the giant butt that overlooked him began to roll back over. Was she awake yet? Simon couldn’t tell, but there was no escaping his morning wood, and the oppressive activities that were destined to follow. He had been catfished.

Chapter End Notes:

I may adjust and elaborate some parts in the future. But for now this is a short one-off that has been illustrated on Giantessfan. Though I don't think they quite made Kathy as described.

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