Jessie's Time for Payback - Sex Stories

Jessie's Time for Payback

... and I drove over to Dan’s house as Jesse, my male self. I walked up to the front door and heard several voices. I rang the door bell, and Dan answered. “Come in Jesse! Now the party can start!” I walked in and saw Zach and Aaron enjoying a beer. “Jesse!” they said in unison. I replied, “Hey Zach and Aaron!” I sat down and had a beer as well. We talked a lot about the work week and how there is another big project that will be starting shortly. After a while, the subject went on to some of the hot women at our work, and honest talk about who we would want to have sex with. Eventually it rolled back to Dan who was a little quiet during the conversation. Dan told us, that there was a woman that he had sex with recently, and her ass was amazing. He went into detail of how she clamped her legs around him so he had no choice but to unload in her ass. As he was stating this, he looked right at me and smiled. That same look of horror came over my face. Dan proceeded to say that he'd invited her to come over tonight to have some fun with some more co-workers. “I’ve always had a fantasy to have sex with a woman wearing this.” Dan pulled out two packages and I immediately turned bright red. It was my Slave Leia costume and high heels that I'd ordered the weekend before. Both Zach and Aaron wolf whistled their appreciation of the costume and high fived each other. Dan looked right at me and said, “It’s time for payback.” He handed me the package. Dan directed me upstairs into his room ...

... where several other items were waiting for me. There was a wig with a long braided ponytail, a makeup set, and a pair of thigh high nude pantyhose. Before he left me alone, he said, “I want you to get ready to serve us tonight. If you don’t, I’ll share the photos that I took of you in a very compromising position.” I quickly put on make-up, the Slave Leia costume, and neck choker with chain. Next were the nude pantyhose, of which I took special attention to not run them. Finally I put on my bronze colored strappy high heels. I looked in the mirror and realized I might be able to pass as a woman if I could apply make-up skillfully. Finally, I walked downstairs as sexily as I possibly could. Even though I was embarrassed, some of the same thoughts of wanting to be a complete woman entered my mind. I turned the corner into the living room and Zach laid his eyes on me first. “Oh my god! Dan! You’re right! Jessie looks hot as a woman!” I had an unsure smile from the compliment, but it did boost my confidence. Aaron turned to look at me, and his reaction was equally reassuring. Finally, as Dan grabbed my chain he said, “Come here slave. It is time for your payback. Zach and Aaron, be prepared for a night to remember!” Dan tugged me closer to him and he stuck his tongue into my mouth. It wasn’t the same passionate kiss like the week prior, but a harder more dominating kiss. My inhibitions were waning quickly, and I was starting to get hot and horny. Dan finally released me and I ...