Saturday night I sat on the couch with Michelle and Sis describing part of my experience at the club. I told them how most of the gurls were poorly dressed and made-up without the help of caring people like I have. “I’m sure I told you both before, but, I so appreciate what you have done for me over the years.”   Sis replied, “You have always been there for us and we will always be there for you. By the way, we want to go...

I sat in front of my computer and started surfing transgendered sites when I came across an article on psychiatrists specializing in cross-dressers, transvestites, and transsexuals. Some of their treatments included a psychological evaluation, hormone therapy, group sessions, and preoperative assistance. The mail order hormones I was taking were having some positive effects, but I read there were better and safer hormone...

I was excited about the next soccer practice. There were no guys at the last practice due to Gurls Night. I was hoping Donny would be there this week. I stopped working at 4:00 so I would have enough to time to get ready.   I went into the bathroom and filled my douche bag with a little over two quarts of warm water and special soap. I took off my shorts and panties before pushing the enema nozzle into my ass. I still get...

It was almost midnight when I got home from my foursome. When I walked into the house Mandy was sitting on the couch watching the television wearing a shear teddy with nothing underneath. She looked at me and said, “Where have you been all night young lady?”   I answered, “Out with the boys, Sis.”   “I hope you don’t mean what that sounds like.”   I responded, “If it sounds like I had sex with multiple men at the same tim...

After returning home from dropping Mom and Dave off at the airport, I immediately jumped in the bathtub and took a long bubble bath. While I was in the bathtub, I shaved the stubble that was starting to form from days of neglect. When I finished my bath, I rubbed most of my body with a good lotion to restore its smoothness, followed by a badly needed pair of sexy red lace bikini panties with a matching bra. I pushed a pai...

Life as Joann was moving forward rapidly. With the house to ourselves, I began ordering many things online and having them delivered to the house. In addition, to clothes and lingerie, I ordered a women’s facial electric razor, a laser hair remover, and several kinds of women’s skin cream. I also ordered some different breast forms to try out. Sis insisted on seeing everything that was delivered to the house, which wasn’t...

As I awoke on Christmas morning I found three presents on the end of my bed. There were handwritten tags on each with the message: open in private. There was no doubt in my mind as I opened them that they were from Sis. The first was a body shirt that pulled down and snapped in the crotch. It was white with a v-neck trimmed with lace around the neck and sleeves. The second was a set of breast forms slightly bigger than my...

As I opened my eyes it was quite light. I sensed it was late morning. Bob was still spooning me, but his dick was soft and must have pulled out of my ass sometime through the night. I quietly rolled out of the bed and walked to the bathroom. Before sitting to pee, I reached around and pulled another condom from my ass. I guess when he lets his dick soften inside me it shrinks from the condom leaving it in my tight ass. I’...

The next morning I told Sis that I spoke with Bob on the phone, as she suggested, and he invited me over to his apartment on Friday night. I think she was as excited as I was. She said we would have to pick out an outfit tonight when we both got home for the big event.   The next day all I could think about at work was Friday night. Toward the end of my shift, my phone buzzed that I had a text message. It was from Bob. My...

As we drove home from the Halloween party Sis asked me if I enjoyed my first time out as Joann. I replied, “It was great. How did you come up with the name Joann?” “Well, I really didn’t think about it until I introduced you to Michelle. I actually started to say Joseph when I realized I needed to correct myself. I guess Joann was the only logical name at that point. Do you like it?” “Yeah, it’s nice,” I replied. “Thank y...

Life was becoming a little confusing. I was out of high school and attending the local community college part-time at night while I worked at the machine shop during the day. I played soccer on the college team in the inter-county conference. Mom helped me buy a nice used car. Still, I wore panties, a bra, and nightshirt to bed every night. Sis was working part-time at a hairdresser while taking cosmetology courses in the...

My name is Joseph and I want to explain how I started on the road to eventually becoming Joann. I grew up with my sister Amanda, who is two years older than me. I have always called her Sis. My father left my mother when I was around sixteen years old and we continued to live in the house. Eventually, my mother had to start working as a bartender in a high-end hotel bar at nights. I still remember my sister prancing aroun...