Bailey Stories

782 results
Orientation
Length
Source
Infinite Scroll

Goldie Locks

by CaseyMathis on Jun 26, 2019
Humor & Satire

** My own take on a classic fairy tale... Goldilocks and the Three Bears. Enjoy!** Once upon a time, there was a young, successful business woman called Goldie. Goldie had everything a woman could wish for; long straight hair as dark as chocolate, a svelte size 12 figure, pert breasts that didn't need a bra, dark eyes that you could get lost in and an almos...

A Day in Office Ch. 02: Fantasy

by vantan on Sep 16, 2017
Fetish

Vanessa had barely made it closing the cubicle door when the men's main door swung open. Vanessa hoped their talking would not distract them from anything out of the norm. "Traces" of an unusual lunch time event that had ended less than 10 minutes earlier could still be spotted, especially if one were to look hard enough - in particular the urinal unit which...

Recruiting of a Sissy Maid Ch. 14.5

by Sissy_Chantel on Dec 16, 2017
Transsexuals & Crossdressers

Readers, I am adding another quick short story of tranny girl Bailey hungry for men and cock. Inserting this story between Chapters 14 and 15 of "Recruiting of a Sissy Maid". I hope you all enjoy it. ***** Title: Another T-girl Bailey out and on the Prowl for Men and Cock Story Friday night, I've been feeling a desire to dress up as Bailey all fucking day...

The Lady Executive Returns Ch. 10

by VickieNight on Sep 15, 2017
Novels and Novellas

Readers, please note that this is a multi-volume and multi-chapter story. It is best when read from the beginning "The Lady Executive, Chapter 1". While Lance was mentioning real estate to me, Caroline was in Boston in her Penthouse getting ready for work. As she looked at herself in the mirror, she didn't see the tall, stunning, beautiful woman she was...

6-Month Waiting Period

by gallactic_erotic on Apr 20, 2020
Romance

There's a fine line between losing your shit and actually tumbling over the edge. I have spent most of my life teetering on the edge, desperately trying to avoid the inevitable tumble. But fuck, the fall is fun sometimes. "Sara, I'm gonna need you to hang back for a few after the show. We've got some stuff we wanna throw at ya." Shit. I'm 27, right? We...

A Dangerous Obsession

by Dixiedevil67 on Sep 26, 2017
Exhibitionist & Voyeur

*** THE NEED WITHIN *** Bailey didn't know why she did the things she did. It was like some unseen force controlled her from within. Once she got a thought in her head, she was compelled to find a way to act it out. It consumed her, the planning, the thrill of possibly being caught, the rush she gained during her daring escapades. But, her obsessions were b...

Milking The Bull

by DamienDeath20 on Jan 23, 2019
Transgender & Crossdressers

A.N.NEW STORYYYYYYY!! :DDD This story is actually heavily inspired by the Monster Musume universe, if you've never heard of it you should check it out, it's pretty funny and quiiiite sexy :3 The Following Contains: Breast milking, and cock milking by a human femboy with an anthro minotaur. Yum. This story is long since overdue so read along and enjoy...

Emma Ch. 02

by Emma7588 on Feb 5, 2018
Erotic Couplings

I bit back a moan of disappointment as the explosive climax that had been building fizzled out like a damp squib. Above me Tom thrust against me, his cock pumping my pussy as he moaned my name over and over again. I felt him jerk against me, his hot cum filling my pussy before he collapsed on me, body trembling from the intensity of his climax. "Thank you,...

Sexual Institution

by NudeDreams on Sep 11, 2017
Exhibitionist & Voyeur

~Everyone in the following is over the age of 18~ * Maddie looked herself over in the mirror as she slid into her uniform; a tight fitting, partially see-through white button down blouse with a high hemmed grey pleated skirt. Her dark auburn hair fell just past her shoulders, and she had styled it in a wavy curled fashion that framed her small, cute face....

Girlfriend’s Daughter

by Nicegent42 on Mar 6, 2021
Transsexual

Bailey hung up the phone smiling “Well three hundred dollars poorer I will be, but I know you are will be worth it Candy.” His mind drifted back in memory to the beginning of the month when he had the escort over before and how wonderful it felt when she had him in her mouth. The smile lost most of its luster when he looked over at a photo of him and his gir...

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