Jaime Stories

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Caught by Two Playmates

by MasturbationSuperstar on Sep 17, 2017
Celebrities & Fan Fiction

I come home from a trip and unwind. After dinner and some time watching tv, I notice a light on from the apartment across the way. I look out the sliding doors of my apartment to see Playboy Playmate Hope Dworaczyk in her apartment all alone. I shut off all the lights, but still leave the television on, which lights up the living room as I stand at the wind...

Under Mommy's Direction Ch. 05

by MommysHypnoSissy on Apr 13, 2020
Transgender & Crossdressers

The rest of Jaime's day had been a whirlwind of tasks and chores to complete before his Mother got home. His online Sissy Trainer, who demanded that he refer to her as 'Mommy', had given him a myriad of tasks. First it was cleaning up his Mother's bed and sexy toys, putting everything back how he had found it. Then it was back to his room to dispose of his b...

Sissy for Mommy's Nipple Cream Ch. 04

by ppeaks42 on Feb 11, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Jaime clasped a hand over her mouth in horror, but it was too late and she knew it. Chills ran down her spine as Julia sauntered over with a wicked smile, then opened the door to reveal her sissy daughter sitting there wearing nothing but her lacy panties and her steel clitty cage...

Jaime's Fun

by libgirl918 on Aug 31, 2017
Exhibitionist & Voyeur

Jaime nervously tapped her foot against the bar, her green eyes piercing the musty haze of cigarette and cigar smoke. She hadn't expected the bar to be so crowded – and dingy. She discreetly pulled at her tight, black spandex skirt – careful that it did not rise so high to reveal her garter belt – and took another sip of Chardonnay. She eyed her watch, wonde...

Sissy for Mommy's Nipple Cream Ch. 05

by ppeaks42 on Nov 2, 2020
Transgender & Crossdressers

The evening after Jaime's doomed attempt at seducing Julia found the young sissy crying into her pillow as she tried to reconcile herself to the whirlwind of changes she'd gone through. Less than two months ago "Jaime" had been nothing but a shared figment of imagination, a character he dressed as for his regular breastfeedings with his mother. When he'd tri...

Exploring Sex Ch. 2

by MisterE27 on Sep 14, 2017
First Time

Jaime couldn't believe the sensations she felt in her pussy after her experiment with Sarah. It wasn't necessarily a painful feeling, but certainly stirred her inside until Friday morning; she anticipated her rendez vous later in the evening with Shawn as she casually admired her beauty in front of the mirror. She only wore a floral silk robe, lilacs scatt...

Studying Abroad Pt. 01

by Tiffany8 on Oct 15, 2017
Exhibitionist & Voyeur

Every person in this story is over the age of 18. ***** Jaime had been preparing for this trip for what had felt like years but really had only been a couple of months. She had been packing her bags for the last two weeks to make sure she had everything since she was going to Fiji to study abroad. She knew anything that she did not have it would be difficu...

Defiling Jaime Ch. 02

by Jaime1989 on Apr 22, 2020
Erotic Couplings

Chapter 2 "Sorry I didn't call you last night," Jaime said to Carrie. "That's OK, but tell me what happened. I want to hear all about it." Jaime described the entire date to her and told her how much she was looking forward to their next date. "I'm glad you had a good time Jaime. He sounds like a catch and he's definitely interested in you or he wouldn't...

I Am a Sex God Ch. 06

by unremittingdesire on Sep 18, 2017
Sci-Fi & Fantasy

Hello readers. You don't need to read previous chapters but it will be helpful in understanding some of the dynamics. The most basic thing you need to know is that the main character is a Sex God in a literal sense. He has the actual power of a deity to alter reality to his will and is quite adept at anything sexually related. Thank you for the support and...

A Hot Summer's Night Ch. 03 - Illustrated

by DarkBreezly on Jan 7, 2019
Illustrated

Author's note: Apologies for the delay in my stories, I have been working on updating my illustrative capabilities with a new 3d Rendering system. It has taken some time to get up to speed, acquire assets, practice, etc. This ended up putting my writing on the back burner for a while as I figured out how to move forward. My plan going forward is to release...