1. Jessie's Time for Payback


    Date: 11/14/2014, Categories: Crossdressing, Author: JessieCD, Rating: 14, Source: LushStories

    After Dan left me with his cum dripping out of my ass, I kept replaying his words before he left. “Jessie, you were amazing! I can’t wait to tell all the guys at work about this!” It was Friday night. Dan was the first one to make me feel like a woman, but now I had another dilemma. How am I going to face him and all of my co-workers if he indeed tells everyone about me? I woke up Saturday and took a nice relaxing lavender salt bath. While soaking and exfoliating my skin, I reflected back on the events that happened the night before. Even though I fantasized about being a woman, and wondered what they felt while having sex, last night was quite unexpected. It was a serendipitous moment. I smiled while I replayed the events in my head. Later in the day I went on a shopping spree. I usually like the more anonymous feel of online shopping, and today was no exception. Even with my new Red Riding Hood costume, I couldn’t resist looking at the women’s costumes at several online Halloween retailers. All of the hot sexy costumes were starting to get me more and more excited. I went to the clearance page and started to scroll through the discounted costumes. Then I found it. It was the costume that was the subject of many fantasies. It was the Slave Leia costume. My fantasies were of me enjoying a woman dressed up as Slave Leia, not of me dressed up as Slave Leia. But here I was, picking my size, and completing the check out. Now that I was going to have another new hot sexy costume, ...
    I needed a new pair of shoes to go with it. After several searches, I found a pair of bronze colored strappy high heeled sandals. They were perfect for the costume, and the retailer had a size that would fit me. Another check-out, and another satisfied customer. The shopping spree definitely took my mind off of what might happen on Monday. Monday came, and I was dreading going into work. The commute was painfully slow which only served to extend my agony. When I got into the office, there was nothing out of the unusual. I sat down in front of my computer and checked my e-mails. There was one waiting for me that was from Dan with ";)" as the subject matter. I hesitated to open it up, but in the same token, I had to know what he sent me. Jessie, Thanks for having me over to celebrate our achievement last week. You sure know how to celebrate! ;) Dan Okay, not too bad. On Wednesday, I was walking down the hallway when I thought I heard Dan say, “and I was the big, bad, wolf,” to Zach and Aaron. As I walked by them, there weren’t any snickers or stares, so I thought to myself that I'd misheard Dan. The rest of the week was uneventful, so I felt pretty good that maybe this would blow over and only Dan would know my secret. At least it was uneventful until Friday. On Friday afternoon, I received another e-mail from Dan. Jessie, I’ve been thinking about last week a lot, and I would like to continue our celebration tonight at my place. Be there at 8pm. Dan It was now Friday evening, ...
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