Bailey Stories

782 results
Orientation
Length
Source
Infinite Scroll

Bailey Ch. 03

by WhiskeyIsGood on Oct 21, 2019
Transgender & Crossdressers

Holding to my word, I didn't let the incident with Billy and his friends scare me away from Bailey; I kept seeing her, even after the beating I took. To be honest, I'm not sure if he was trying to lay low or what, but Billy seemed to keep his distance from me for a while...thankfully. Bailey and I continued hanging out, going to parties, playing video games...

Futanari Academy Ch. 02

by TheOrcKing on Jun 3, 2019
Transgender & Crossdressers

(All characters participating in sexual activity are age 18 or over.) This chapter is a repost, it has been edited and has undergone very minor rewrites for style and flow. Nothing in the story has been changed. Chapter 02 "Is our son in trouble?" "Are is his grades slipping, is that it?" "No, no! Nothing like that. In fact, your son is an exceptional y...

Two Hundred Dollars Ch. 21

by xtorch on May 15, 2019
Fetish

115 Dollars "So let's get this straight," Laura said. "Go ahead." Laura set her tea cup down firmly in the centre of her gingham place mat and squared off against Bailey. She gave one last glance around her mother's kitchen before going on. "Getting spanked to pay off a debt," Laura paused. "Not prostitution." "Right," Bailey agreed, equally firm, and s...

The Rendezvous

by primowalker on Sep 2, 2017
Erotic Horror

It was the kind of cool, crisp morning that you would expect from October. The first frost of the season was just beginning to melt from the grass so that the dog's paws and his sneakers were quiet wet before they'd even walked fifty yards. They'd only just started coming here earlier that week. There were two baseball fields, a boat landing, a small playg...

Two Hundred Dollars Ch. 07

by xtorch on Nov 6, 2018
Fetish

169 Dollars Bailey managed to avoid Kent for the rest of Thursday and on into Friday. She spent a lot of that time trying to figure out whether she cared about what had passed between them. By Friday afternoon, after a great deal of deliberation, including the consultation of several online dictionaries while browsing in incognito mode, she had definitely...

A Wet Summer Ride

by AbigailAnne on May 20, 2019
Toys & Masturbation

It was a cool, grey Summer afternoon. Adeline had spent the day checking off items from the farm's 'To Do' list. In the stable, she spent her time scrubbing off dirt patches from Lark, one of the family mares. Adeline brushed one of the long, blond hairs that had strayed from her braid out of her eyes. Bailey was supposed to be back from his afternoon ride s...

Futanari Academy Ch. 12

by TheOrcKing on Jun 10, 2019
Transgender & Crossdressers

(All characters participating in sexual activity are age 18 or over.) This chapter is a repost, it has been edited and has undergone very minor rewrites for style and flow. Nothing in the story has been changed. ***** First thing Monday morning, Bailey found himself sitting outside of the Vice Principal's office. He was ordered to report there by Pickwell...

Two Hundred Dollars Ch. 24

by xtorch on Jun 24, 2019
Fetish

It took Bailey three hours to realize what had happened. To be fair to her, she experienced in those few hours so much discomfort just from sitting down, the nagging sensation of having forgotten something important had registered on the needle of her sensations. But, sometime around two o'clock in the afternoon, she noted that her underwear felt a bit f...

The Mop and the Cyclops Ch. 03

by RusticxReads on Mar 23, 2020
Sci-Fi & Fantasy

The Mop and the Cyclops Chapter 3: WARNING: To those reading this, this story contains dual-cocked futanari, huge cocks, tons of cum and quite a bit of belly bloating, as well as some other funky kinks. Read only if you're into that shit. You've been warned... or blessed... take your pick! With both hands on the pink beauty's inner thighs, I sit there as...

Two Hundred Dollars Ch. 20

by xtorch on Apr 9, 2019
Fetish

116 Dollars Bailey took her notebook in hand early Tuesday morning when she realized she hadn't filled it out in several days. Thank god I remembered to do it on Friday. That was hella complicated, what with Laura helping and all the showing and removing clothes. That forced her to go over the eight spankings Laura had delivered. I'm not even going t...