1. 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 ...
    yesterday hoping Bill liked it and would want to see me in it again. I wasn't sure he even knew i was wearing one. After i was satisfied with my appearance, i put my ear up against my bedroom door to listen for any activity from my family. I was positive i didn't hear anything and slowly opened my door. I was so nervous i was shaking. It felt taboo walking in my house like this and i could feel myself rock hard under my skirt. I made my way down the stairs and to the garage door, where i parked my car, i was about to open it when. I heard someone opening my parents door across the room behind me. Quicker than any door i had ever open, i was in and out in a flash. I hit the button to open the garage door and ran to get into my car. My heart was racing as I started the ignition and pulled out and drove out of my driveway fast as i could. I made it, i couldn't believe i made it. Once i was out of the neighborhood i lived in, i heard my phone was ringing from the purse i brought with me. An old one my sister was going to get rid of before i snached it. I looked to see my Dad calling me. I’m sure he was just calling to see where i went. There is no way he saw me so just calm down I told myself. “Hello?” i answered his call sounding calm as possible. “Jacob? Did you just leave through the garage?” He asked “Uh yeah. I’m going down to get breakfast with a friend this morning. I told you about it last night.” I said acting causally as possible. “Yeah now i remember. I just swear i thought ...
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