Pleasing Bill: A Crossdressing Story #2
Date: 4/25/2018, Categories: Fiction, Anal, Blackmail, Oral Sex / Blowjob, Domination / Submission, Humiliation, Reluctance, Trans, Trans, Trans, Voyeur, Author: JessRider, Source: sexstories.com
Chapter 2: First Day On The Job “That’s what i like to hear. Now at 12AM tomorrow i want you to be at our house dressed up in the sexiest outfit that you can get your hands on. I’ll text you our address.” “I can't. My family are still at home by 12.” I pleaded. “That’s not my concern. Now this is your first task i’m telling you to do. Are you going to fail me already? Because you be here at 12 o'clock on the dot or you can forget about ever seeing me again.” Bill said annoyed. I couldn't disappoint him. I need to prove i’m going to worth his time. “I understand, Sir. I will be there.” “That’s a good little whore. See you then.” He hung up. How the hell am i going to get out of here ,dressed up like a slut, and be there at 12? I kept some of my sister’s clothes she was going to give away, and didn't notice were missing, in my room. So i know what i am going to wear but how do i leave the house with anyone seeing me. I never even left my house dressed like a whore. I can leave before they wake up but i’ll have to kill time before i get to Bill’s. I went to sleep with my alarm set to 9AM knowing my family is a bunch of late sleepers and wouldn't be up until 10 or 11. I should be able to leave without notice. The next morning i was up and dressed with in 10 minutes of waking up. For the outfit i decided that a black short skirt with a white shoulder length top. I Put on the only girly shoes i had and applied some extra make up than normal. I decided to use the same wig from ...