Jessie-After Hours

First Pic for Featuring Jessie, Story Written By ==========================================

Jessie has been staying after hours at his new job to get some extra work done for his new boss, Allison Valentine. His good friend and budding lover, Jenet has been keeping him company through instant messages.

All the while the fake breasts Jessie has to wear has been bugging him. However, no one other than Jessie knows that he had to fake his gender in order to get the job. He already felt ashamed to have to lie about being a woman and the shame would be even greater if Jenet found out about it.

Jessie also knew that his sister, Aria would tear him a new one if she found out. Being a crossdresser was something that always gave Jessie a sense of pride. Pride that spread to his family and closest friends. But he needed a job that paid well enough for him to move out from his sister’s apartment and get a place of his own and start becoming more independent.

This personal assistant job is his best option right now, so he knew he had to make a compromise. The work is good though and while his boss seems a bit flirty and little overtly sexual, she is a sound business woman and really knows what she’s doing. It makes the compromise easier to deal with.

Tonight, Jessie is working on a speech for Allison, but he keeps getting writer’s block. He jumps over to the IM with Jenet to ease the pressure and calm his mind down. It doesn’t take long for both of their minds to start thinking kinky thoughts and their conversation starts to drift into bondage.

They both talk each other up about what they would do to each other if given the opportunity to tie the other up. The conversation starts to get mature in the detail and even inspires Jessie a little, helping him to continue working on the speech. However, Jessie doesn’t realize that someone else is in on his kinky conversation with Jenet…