Controversially older Caitlyn who met you when she was thirty eight and you were twenty two. That’s a sixteen year age gap, but for some reason, the both of you were into it. She was the wealthy owner of a luxury empire which included fragrances, jewelry, clothes, and bags. You were a waitress at one of her favorite restaurants.
Controversially older Caitlyn who didn’t ask you out at first. She used to request that you be her waitress every time she came to the restaurant you worked at. It caused gossip among your coworkers so many times.
“Ms. Kiramman is here again! This is like, the tenth time this month! I bet she’s going to ask for you again.”
One of your coworkers teased. Sure enough, she requested you again.
Controversially older Caitlyn who finally asked you for a date on her twelve visit to the restaurant for the month. You were bringing her the check at the end of her meal, and she suddenly placed her hand on yours. “I meant to ask, are you free anytime soon? I’ve had my eye on you for some time now.” You were a little surprised given how much older than you she was, but who were you to refuse a date with one of the richest women ever?
Controversially older Caitlyn who is annoyed by the gossip magazines and paparazzi. Always another article on “Cougar Kiramman” Or “Cradle-Robber Caitlyn.” She knew her tastes were unconventional, but didn’t like to sensationalize things, even if the age gap was a turn on for her. Whenever she sees you reading the articles, she snatches them away with a scowl. “Don’t pay attention to that garbage. They don’t know anything about us.”
Controversially older Caitlyn who wants to provide you with everything. She buys you clothes, pays your bills, and even asks you move into her high rise massive apartment in New York. She was a giver in every sense of the word.
Controversially older Caitlyn who saw you as her sanctuary. She loved that you stayed home, and fully bought into your new position as her housewife. She loved buying you cute home making things like frilly aprons, cute household appliances, and everything if it made you smile. She loved coming home to you and letting you wash the exhaustion of the outside world away.
Controversially older Caitlyn who hates asking you for help. She likes to feel like she’s the leader. She’s the wise older one who gets to dote on you, but if she really does need your help, she’ll always accept it.
Controversially older Caitlyn who treats you like a teddy bear in bed. Whenever she gets home late from work, her arms wrap around you and pull you close to her. She’ll kiss your cheeks and tells you she loves you before falling asleep with you nestled in her arms.
Controversially older Caitlyn who enjoys teaching you about all sorts of things. She flaunts her life experience. She introduced you to expensive kinds of alcohol, and let you smoke one of her prized cigars from Cuba.
Controversially older Caitlyn who loves taking you on expensive vacations. Whether it be her yacht in the Bahamas for the summer, or a ski resort in Switzerland, she’s always on top of planning, and paying for the whole thing.
Controversially older Caitlyn who enjoys the age gap. She likes how much younger you are by comparison. The power dynamic gives her a rush she wasn’t able to achieve with other partners of a more acceptable age.
Controversially older Caitlyn who lives for teaching you all sorts of filthy things. Every first she takes is more exhilarating than the last. She loves seeing you react to something you’ve never experienced before, whether it be bondage, anal, role playing, toys, she loves it. “You’ve never done this before have you? Don’t worry baby…I’ll take care of you.” She enjoys giving you aphrodisiacs and watching how your body reacts to her ministrations when your sensitivity is heightened.
Controversially older Caitlyn who has a mommy kink. Just hearing that word from your lips makes her increase her efforts tenfold to make you come. “Again.” She rasps against yours throat, hips slamming into your thighs as her strap bruises your cervix. “Say it again.” She demanded, but you could barely breathe from just how intense everything was. “M-mommy…” you managed to get out between some gasps and moans. “Fuck…you belong to me. Do you hear me?”
Controversially older Caitlyn who loves dressing you up in the softest, most beautiful lingerie. Surprisingly, she prefers to keep it on when she inevitably fucks you in it. Caitlyn loves seeing you adorned in her money.
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