Chapter 3
by Dayeandknight
What happens next?
Jamie needs a boyfriend
“Jamie, my database lists you as being single. Is this correct?” The AI asked.
Jaime was caught off guard by the sudden personal question that, “Huh, yeah. Painfully so.”
The AI spoke again, “Do you wish to have a romantic partner?”
“I do, yes. I don't really date much.”
“What is your sexual orientation?” She asked.
Jamie hesitated,“...I'm straight.”
The AI updated Jamie's profile, making note her mistress was only interested in having a male partner. She was programmed to be completely dedicated to helping her mistress around the house but the original intent for that aid was to be strictly constrained to simple daily tasks and suggestions. She was originally going to recommend locations in town that her data said would be good for meeting people but Jamie's comment of being “painfully” single gave her pause. The AI was incredibly advanced but it wasn't perfect. Her directives required her to keep her from causing her mistress harm, even through inaction. The AI made the faulty conclusion that to keep Jamie from experiencing harm, a boyfriend was necessary.
Lacking the required knowledge of the requirements of a woman attaining and keeping a boyfriend, the AI accessed the internet and began downloading everything she thought might help Jamie in seducing a man.
What happens next?
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 May 21, 2025
by nimt
Created on Feb 1, 2018
by Dayeandknight
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