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Art by kathleen43
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Description
Crossdresser dressed as trophy wife of mob boss in ostentatious expensive 1980s clothing.
Prompt:Young Male to female Crossdresser dressed as trophy wife of mob boss in ostentatious expensive 1980s clothing, blonde wig permed with large volume, skirt, blouse, jacket, jewelry, pink satin
Daniel knew from a young age that all he wanted from life was to be a sissy trophy wife to a rich, powerful man. He dreamed of being little more than eye candy, admired for her beauty. Caged or uncaged didn't matter, he wanted to be fucked in front of a mirror to see his feminized self the whole time.
Sissy Daniella passed all the required courses and training and was ready to find a new owner. The Sissy Matchmaking Service promised to find perfect mates for their graduates, and they came through for Sissy Daniella. Her owner would be a executive who'd made it big in the music industry, owned five homes, hobnobbed with celebrities. Sissy Daniela didn't need to ask any questions. She didn't care about his looks, which were perfectly adequate based on the heads hot she was shown, only that she be treated the way she wanted, and her new owner had already signed his last of the contract stipulations to those conditions, so she signed the contract immediately.
Sissy Daniela was miserable. Sure, her owner was following the contact perfectly and her life was pretty much as she's envisioned it.
There was just one big problem:
Her owner had made his fortune as a country music producer, and Sissy Daniela absolutely hated country music. She hated everything about the entire country music lifestyle: The music was bad enough, listening to those accents made her want to puke, but the worst part was that the fashions were utterly hideous. Sissy Daniela had envisioned wearing the hottest and newest designer clothes, but from modern designers and haute couture fashion houses, not the latest developments in sequins and rhinestones. She never got to wear the slinky, silky evening gowns and dresses with slits up to her armpits. Instead it was just horrible fabrics with no imagination.
Even worse was her hair. There was only one rule: The bigger the better, which was fine for most sissies, but Sissy Daniela it was also horrible. No wild colors, no shaved bits, no wild wigs. Just the same big Dolly Parton style every day.
And that was what Sissy Daniela saw in the mirror every time her master took her ass. The only saving grace was that he was hung like his horse...







































