JessieCD 7 Mar 2022 Chapter 1: The Question of Taking the Pill Jessie explores the question of, "If you could take a pill to become the opposite sex, would you?" If you could take a pill that would permanently change you to the opposite sex, would you take it? Few people would state an immediate yes to jump on the chance to take a pill that would change their gender forever. Most of which either knew at a very young age or even just recently realized that their genetic makeup did not suit who they are on the inside. If you could take a pill that would permanently change you to the...
JessieCD 12 Oct 2018 An Unexpected Surprise Now that Jessie coupled with her step brother, what is in Jessie's future? A long overdue sequel to my stories "Mistaken Identity" (Ch. 1) and "The Coupling" (Ch. 2). I couldn’t believe the turn in events. Here I was in the kitchen, half-naked, juices from our coupling dribbling down my thighs, and it wasn’t my dream man John, but my step-brother Matthew that was behind me all naked. It certainly was the best sex that I had ever had, but I really wanted my parent’s best friend John to fill...
JessieCD 8 Dec 2017 My Third Time After Jessie confesses her love for Kasey, what happens next? After Kasey and I made love the second time, I seriously started to question what I wanted to do with my life. I really hated the fact that I had this male appendage, yet the last two nights with Kasey made for a convincing reason not to get rid of it and remain transgendered. Yet, the hate for having any male parts was strong, and I didn’t know if I could live life with it even though Kasey showed me how much pleasure...
JessieCD 30 Oct 2017 My Second Time Now that Jessie lost her virginity, what happens next? Never in my wildest dreams would I have thought that my first time would have been with a woman. I was born a genetic male, but growing up, I always knew that my body didn’t match who I am. My early life was miserable as I was always ridiculed by my classmates in my little home town. I finally graduated from High School and moved out of that horrible place and started college in Seattle. College was so much better. M...
JessieCD 20 Oct 2017 My first time Now that Jessie has entered college, what will happen? It was my eighteenth year, and I was ready to start my new adventure. It was really sad to see the summer go so quickly, but I also realized that a whole new life was in front of me. My bags were packed with my belongings and I was ready to get out of this miserable town and on my way to the big city. I was looking forward to meeting people who didn’t know my past, and would only know me as me. Of course, I still had...
JessieCD 1 Oct 2017 The Coupling After a Mistaken Identity (see story of same title), Jessie plots to take on the neighbor. About six weeks after our unusual family event this one fateful summer day, I woke up to get ready to go to my classes at the local college. Normally, my mother is up and going, but today was different. She was nowhere to be found. I always give my mother a hug and a kiss before I leave the house, so I called out to her.I yelled out, “Mom? Are you awake?”I heard a very muffled response from upstairs. After I walked u...
JessieCD 30 Jul 2017 The Cherry Stem Girl Chapter 2 Jessie has proven her talent to one lucky man, but that was just the beginning. I couldn’t believe what just happened. I was at a party with my best friend Alicia, when she announced to everyone my neat little trick. After showing everyone that I could tie a cherry stem into a double knot with just my tongue, I attracted the attention of three guys. Scott who was the ring master, got me all worked up while I was dancing with him and his two friends, Brian and John. Next thing I know, I was the ce...
JessieCD 29 Jul 2017 The Cherry Stem Girl Chapter 1 Jessie has a talent that only her best friend knows. Until now... “Hey Jessie! I want to see you do that trick!”“What trick?” I replied. I was pretty sure what my friend Alicia had in mind.Alicia looked at me with a sly little grin, “You know what trick. Come on. Show us how talented you are!”I gave her a teasing frown. “Not now! It will be embarrassing with all these people around.””That is exactly why you need to do it. You’ll be the hit of the party!” Alicia walked away from m...
JessieCD 11 Dec 2016 All I want for Christmas Christmas is coming, and Jessie finally knows what she wants. All I want for Christmas… It was only three days until Christmas, and I was madly going store to store, shopping for my fiancée Brad. I was on the verge of giving up for the day as he was incredibly difficult to shop for, unlike me who loved anything sparkly. My final stop was to a Brookstone, in hopes of finding some cool gadget that he might like. While browsing, I found a drone that piqued my interest. Maybe this is so...
JessieCD 2 Dec 2016 Mistaken Identity One day of mistaken identity yields a life time memory. I was eighteen and in my senior year of high school. That entire first half of the year was all about my girl friends talking about all of the hot looking boys on the football team and how my friends would want to date and have sex with them. Towards March, several rumors started to circulate around the school that the three most popular football players had dumped their girlfriends. My girlfriends wasted no time, and too...
JessieCD 23 Nov 2016 Jessie's Path A true story of the Path that Jessie took. One’s path in life has three primary sections. The first one is what made a person who they are. Everything from their parent’s genetics, to how they were raised, the environment they grew up in, and any uncontrollable outside influences causing a life changing event. The second section of the path is what we see, feel, hear, taste, and touch at this very moment in time. It is a collection of fleeting moments that may or...
JessieCD 21 Nov 2016 Jessie's Fantasy Chapter 8: A New Beginning Jessie finishes having fun with her male friends, So what does Tracy have in store for her? 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...
JessieCD 7 Aug 2016 Jessie's Fantasy Chapter 7: The Tables Got Turned Now that Jessie decided to turn the tables, how will she handle all of her friends? Here I was, getting my boy pussy plowed by my good friend Scott, when Mark decides that he needs to call Jesse, the male me. As he was starting to dial my phone number I realized that I never turned the ringer to vibrate after we left the night club. I was panic stricken as they all knew the distinct ringtone that I used. I couldn’t let my phone blow my cover. I had to think fast, but what to do? Suddenly, Scott moaned th...
JessieCD 25 Jul 2016 Jessie's Fantasy: Chapter 6 Turning the Tables Now that Jessie fooled his friends, who will turn the table on whom? I was floored by what Tracy had said to me. “Because, the male Jesse is no more for the time being, it is womanly Jessie that needs to go.” It seemed that my love just told me that I had to meet up with my male friends tonight. My mind was going a mile a minute. I already fooled my friends once. But can I do it again? If I do, what is going to happen? What will I let happen? My stomach felt like butterflies. I was getting...
JessieCD 13 Jul 2016 Jessie's Fantasy Chapter 5: Afterthoughts Now that Jessie fooled a male friend, what is in store for our heroine? After Tracy mouthed, “I love you” to me, I knew right then and there that Tracy not only loved me as a male but also me as Jessie. I could feel my cheeks get warm and flushed from her comment and my thoughts. This was turning out to be the best day of my life. My thoughts were interrupted when Mark’s cock softened to the point that he slid out of my backside. Now my thoughts were replaced by something totally different.It...