What a crazy twenty-four hours it had been. It all started last night with me losing a bet to my friend John, one which I should have never lost, but did. My payment was to dress up as a female while going out with my friends until I was able to successfully have a guy try to pick me up. Earlier today, I went to my friend Tracy’s house and told her about my dilemma. After a few laughs, Tracy took me seriously and enlisted...

After an amazing afternoon with Tracy, Suzy, and Brooke regarding my transformation and amazing feminization via sexual acts that wore me out, it was time to meet my friends. Before we left, I called my friend John and told him that female Jesse would have to wait. I told him a little white lie that I had developed stomach flu and had been throwing up all afternoon. John told me that he was disappointed, and was and certa...

Here I am in the bathroom buck-naked and hairless. An amazing thing happened in the tub of my best friend's bathroom. My secret love and best friend Tracy, just had an amazing love making session. We were starting to get hot for each other after I dried off when the door bell rang, and her beautiful naked self ran out of the bathroom to answer the door. I started reflecting on what just happened. Mister shy guy, loses a b...

Nearly everyone has a sexual fantasy that they would love to act on sometime in their life. Unfortunately for some, it never becomes reality. There are many different reasons, ranging from having fear or hesitation, to fantasizing about someone they can’t have, or the situation just never presents itself. This is a story of one such fantasy. Hope you enjoy! It was a Friday evening and I was on my way to meet my usual grou...

Sue and I were starting to catch our breath from our office session when suddenly someone started knocking on the door. “Jesse! You’re late to your meeting with me! What in the hell was all of that noise coming from your office? I sounded like someone was having sex in there!” Now I knew I was going to get it. That was my manager Steve. Steve burst through the door and his mouth immediately dropped. After what seemed like...

I could not believe what a great time I had on my first date with Sue. Her planning was impeccable. From getting caught at the department store, to my new set of lingerie and clothes, and then a feminization session at the salon. Only to wrap this up with a surprise sexual encounter with Sue, her male friend Quenten, and all whom I met at the various retailers. It was a first date that I would never forget. I still was in...

I could not believe I was going out with Sue on a date. It was our first date and she appeared to be my match made in heaven. First, we got caught with my face between her thighs while wearing lingerie in a department store dressing room. Next, we made our way to the shoe shop where not only did Sue buy me a killer set of four-inch heels that were strappy, brown open-toed sandals with little jewels on them, but the store...

Sue and I had a great time in the lingerie section of the department store. Getting caught by the sales clerk was definitely not something we planned on happening, but in some strange way it added a whole new dimension to what we had done. Both of us got out of the store as quickly as possible and headed into the mall. Sue suddenly turned to the right and stopped at a shoe store. This shoe store catered strictly for women...

I felt like my life was spiraling out of control. It all started that one fateful weekend when my secret love of cross dressing was discovered by my coworker Dan. He knew he had me, and he had his way with me. Then came the next weekend when Dan invited me to his house only to have himself, Aaron, and Zach take turns with their sissy slave. And now last night, I was humiliated because of my performance with Tracy while be...

I spent the weekend trying to recover from the pounding that I received from Dan, Aaron, and Zach. I was their slave, and I had enjoyed it immensely. What I didn’t plan on was having all of my moans, groans, and enjoyment being filmed from twelve different angles, along with Dan telling me that he was going to share this video with our office mates. I was worried, yet anticipating what Monday would bring to me in the offi...

It was turning into a wild night, and I was the party favor. After Zach and Aaron had their way with me, I thought I was done for the night. But I couldn’t have been more incorrect with my assumption. As I was getting ready to leave the living room, Dan tugged on the chain that was attached to my neck choker. I went to my hands and knees much to Dan’s pleasure. Zach, and Aaron had been giving each other high fives for the...

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 lavende...

It had been an unusually long and hard week at the workplace. The week started on the wrong foot when a major project was likely to be delayed by a month because of a supplier issue. Stress was adding up through the week as my manager kept demanding that I get the project back on course by week’s end. Come Thursday, there wasn't an end in sight. I was thinking my job will be on the line. I was near the breaking point and...