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Chapter 2
by ShimoDragon
Which Story?
Dating Advice (Hypnosis)
Riley and Isabelle were a fairly normal young couple. Riley was 19 years old, preparing to enter his first year of college after taking a year to "work on himself" and Isabelle was 20, currently finishing her second year of university. The pair lived together in a cozy one bedroom apartment and had been doing so for the past 8 months. There was only one problem... Riley was an asshole.
"I don't know why you're getting so angry all of a sudden, babe," The couple were currently in the middle of an argument which Riley wasn't taking very seriously, "You can just cook dinner as usual."
"You can't be serious Riley!" Isabelle yelled at her boyfriend, "I have been studying my ass off for these finals and you can't even be bothered to help cook? I've been asking you to help out around the apartment all week but you just keep brushing me off to play video games!"
"Uggggghhhh, fiiiiine," Riley paused his game and slowly stood up from his chair making it seem like the most laborious action he had ever done, "I guess I can heat up a frozen pizza or something. You owe me though. How does some head after dinner sound?"
Isabelle stared at him slack jawed, "You're unbelievable... I ask you for one tiny favor and you expect a blowjob in return?"
"What? I thought you liked giving me head?"
Isabelle massaged her temples as she responded, she could feel a headache coming on, "I do it to make you happy, not because it makes me happy. God, you are so ungrateful sometimes..."
"Ugh whatever, be that way then. I'll go make the damn pizza," Riley lowered his voice for his next words, "They're just psychology exams, why is she acting like it's such a big deal."
"I heard that you dick! That was the last straw, no more sex until I finish all of my exams! And you better give me a damn good apology before then!" Isabelle yelled out before storming into the bathroom and slamming the door behind her.
She looked at herself in the mirror in silence. She felt as awful as she looked. Her usually silky brown hair was disheveled and without any makeup her baggy eyes stuck out like a sore thumb. Worst of all, she was on the verge of tears. How could Riley be so rude and insensitive? He knew that she was passionate about her psychology degree and yet this wasn't even the first time he had mocked it. Every additional day she spent living with Riley caused Isabelle to question why she had ever started dating him. Sure the sex was pretty good but that seemed to be the only thing that Riley even cared about.
Isabelle splashed some water on her face and tried to refocus. She still needed to do some studying before she went to bed tonight. She quietly left the bathroom and went to read over some notes. The last thought she had before immersing herself in the material was of Riley again. She hoped that a lack of sex would knock some sense into him but she wasn't very optimistic.
One week later, Isabelle only had one exam left and she finally felt the stress starting to melt away. She and Riley hadn't spoken much since their argument but Riley had started putting in the bare minimum effort to make a frozen meal when Isabelle returned from campus mentally exhausted. She was starting to think that maybe Riley was actually trying to be better. Unfortunately, that belief was proven wrong the very same day.
She had just happened to look over at Riley's monitor while he was off on a bathroom break. She didn't even intend to snoop through his messages, but the damn fool left his discord chat open for her to see. Even though it was right in front of her in plain text Isabelle struggled to believe what she was reading.
Yeah, Isa's been kind of a bitch lately. This no sex thing is starting to drive me insane, maybe I should just find some girl at a bar to have a one night stand with? It's not like she'd ever know, and it's her fault I'm even thinking about it anyways.
He was casually talking about cheating on her like it meant nothing! He... he really didn't love her. In Riley's eyes Isabelle was nothing more than someone to have sex with. She was devasted. Betrayed. Furious. Her rage boiled as her mind raced until a certain thought popped into her head.
If Riley had it his way then Isabelle would be nothing more than submissive eye candy. A sexpot of a girl whose only purpose would be to pleasure him. So what could possibly be a more fitting punishment than to reverse the roles?
To any regular person it would seem impossible but Isabelle could already see the possibilities. Riley was pretty short for a guy at 5'6, he was also quite slim outside of his hips which were already girlishly wide (he hated when she pointed this out). He had soft facial features as well and he kept his dirty blonde hair just above shoulder length. With a good amount of effort he could look the part. But most importantly, Isabelle was already a practiced hypnotist. She was actually taking psychology in order to become a psychologist specializing in hypnosis.
Was her plan convoluted? Without a doubt yes, but that was the whole point. If she could pull it off it would be the greatest **** against her rude and unfaithful boyfriend that she could possibly imagine. On top of that, she would get to truly test the limits of her hypnosis and prove that her degree was more than some pointless joke. Her anger was fading into the background as she was filled with anticipation and excitement. She was done with Riley, romantically, but she had very feminine plans waiting for him in the near future.
How does Isabelle begin?
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Crossdressing Stories
A collection of separate stories that all involve guys ending up in dresses
A collection of separate stories that all involve guys ending up in a dresses
- Tags
- Hypnosis, Misunderstanding, Crossdress, Halloween, Bet, Dare, Crossdressing, hormones, feminization, sissy, housewife, Stepford, Stepford wife, hucow, Maid, Fetish, Femdom, Thigh-highs, mistaken identity, mind control, manipulation, Accidental, Mr Handy, Vault, Fallout, Magical Crossdressing, Leather, Princess, Secretary, Fantasy, pokemon, Mindcontrol
Updated on Jun 20, 2025
by Mr Nice Guy
Created on Feb 1, 2018
by Dayeandknight
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