Jessie’s Fantasy Chapter 8: A New Beginning

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I sat in stunned silence after the love of my life gave up my little secret to all of my friends. After losing a bet with John, I had to dress up as a woman and try to hook up with a guy as payment. Tracy and her friends did such a good job making me look like a woman, that I was able to fool all of my friends into having unplanned, but very much enjoyed, sex with me. It wasn’t until Ross and Steve had their turn with me that Tracy decided to announce to my friends who Jessie really was.Tracy said, “Oh my god hun, you were amazing with these studs! I can’t believe that you actually let all of your friends fuck you and cum inside you!”Fear and a slight moment of panic came across me. I wanted to run away and never see or confront my friends again. I was certain I would get the crap beaten out of me as a couple of my friends tended toward homophobia, and the sheer act of fooling them wouldn’t likely sit well with them.Brian turned toward me in disbelief. “No way!!! There is no way that you are our friend Jesse. He doesn’t have a hot body like you do.”“Or a sexy ass like you do!” piped in Scott.I glanced at all of my friends and bowed my head down. I was about ready to cry. I slowly placed my hand on the back side of my head and unfastened two clips that held my wig to my natural hair, and pulled my wig off. Next, I removed my dress and turned to face them. My poor deflated boy clit was noticeable for all to see.As I lowered my face again, I replied to them. “Yes. This is me, Jesse.”Mark came up to me. I cowered a little as I was certain Escort ankara he was going to be the one that would kick my ass. He placed his hand on my cheek and lifted my face so our eyes would meet. I didn’t see any anger on his face. All I saw was one of bewilderment and confusion. After many seconds of him staring deep into my eyes and pure silence, he spoke.“Jessie, you are one of the hottest, most sensual creatures I have ever been with. I would never in a million years guessed that you were my male friend Jesse.”With that, he proceeded to kiss me. I was in complete shock of this turn of events. We kissed for what seemed like many minutes, and I noticed my tension and fear melted away.Tracy pushed Mark aside and stated to him, “Don’t get too attached to Jessie. She is mine.”What followed was several hours of my friends and I talking about the events that had unfolded over the last couple of days. There was question after question about what I felt, did I like it, who was the best, would I have sex like this again? So many questions came my way. It was all very respectful and they were treating me like a lady. It was odd, as I was a total slut for them. But two things were certain. First, not a single one of my friends suspected at the time that I was following up on my payment. Second, I knew our friendships would never be the same, but at least I knew that they would still be friends of mine. After all of the questions and conversation, there was still the elephant in the room that no one dared to Balgat escort ask. Did I like it enough to continue to be Jessie and give up my life as a male? As Tracy and I were getting up to leave, Ross asked one final question.“Jessie, what will happen after tonight? Are you going to be our male friend Jesse, or is he gone forever?”I replied, “I’m really not sure right now.”On the drive home with Tracy, I was a mix of emotions and conflict. We talked the entire time in the car about my future and what my plans were going to be. Let’s just say that I kept going back and forth as there were aspects of my male self that I enjoyed, and there were female aspects I enjoyed. I told Tracy, I needed to do some soul searching before I conclude what my future would look like.Throughout the week, I continued to wear cute panties under my work clothes as male underwear, for some reason, didn’t appeal to me in the least. I really never thought of it at the time, but my mind was truly made up. That weekend, Tracy dressed me up in sexy lingerie and we made love for hours on end. It was a weekend where neither of us wanted to get out of bed. We just enjoyed exploring each other and learning how to please each other the most. I have to say that our love making was very soft, and we took our time. It was some of the most erotic and most satisfying sex that we had since we became a couple.As the next couple of weeks went on, I started enjoying my feminine side, which meant that I always wore panties to work, and removed Batıkent escort bayan all traces of my male self once I got home. My phone would ring, yet I wouldn’t answer it seeing it was one of my friends. Tracy and I were still intimate with each other, but I noticed that something seemed off with her, especially when we started making love in the morning. When I brought it up to Tracy, she changed the subject. “Hun, I know you are ignoring your friends. They really don’t deserve that. Please go out with them this weekend.”“I don’t know,” I replied.I started getting emotional. It was odd, but the last week I felt very emotional for some reason. This wasn’t like me in the least.“Please call them up and talk to them.” She repeated.I called up Brian and talked to him. After the conversation, I turned to Tracy and told her I was going to go out with my friends tonight. Tracy smiled and said, “Oh good! I am so glad you decided to go with your friends. I’ll make sure I dig up some of your casual clothes to wear.”I turned to her and stated, “That won’t be necessary. I would like to wear something sexy.”Tracy looked at me and smiled.Work seemed to drag by. I just couldn’t wait until 4PM when I would head home and get ready for a night out with my friends. When it was finally time to leave, I called up Tracy and let her know I was heading home. After a fairly decent commute, I got home and opened the door. “Hunny! I’m home!”Unlike every night that I came home, Tracy didn’t answer. I yelled it again, and still no answer. I walked into the kitchen and saw Tracy with her two friends Suzy and Brooke sitting around the kitchen table.“Hi, Hun! So sorry. I didn’t hear you come in.”“That’s OK hun. Hi, Suzy and Brooke! What’s the occasion?” I asked.Tracy opened the conversation “Do you remember our first night together?”“Of course I do.

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