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 around after school in her panties and a nightshirt, exercising our new found freedom when Mom worked. She would often model her new bras and panties in front of me to get my reaction. I couldn’t help wonder what it was like to feel so sexy. I once asked her if I could feel her bra clad breast.

She took my hand and rubbed it over both her breasts. Then she said anything more would be perverted for a brother and sister. She liked to walk around the house with as little on as possible and I enjoyed watching her.

Mom assigned the masculine household chores such as mowing the lawn, taking out the trash, washing the car and such to me. Sis was assigned the laundry and inside house cleaning. On Saturdays, she would pick up my dirty laundry from the hamper, wash, dry, and fold all my clothes, then leave them in a basket on my bed.

One Saturday when I was putting away my basket of clothes I found a pair of Sis’s pink lacy panties. I couldn’t help holding them up and looking at them. They were so sexy, smooth, and felt so good on my skin. I thought to myself she must have accidentally placed them in my basket, so I put them on top of my dresser to give them back to her later.

A few days later they were gone. However, the next Saturday there was another pair of panties in my basket. These were black with red lace and red flowers embroidered on them. This time I had to try them on. I took off my sweat pants and briefs. My heart started racing as I pulled the panties on.

Little did I know this was to be a life-changing experience. The bikini type panties cradled my cheeks like a pair of hands. They pulled my balls up between my legs and made my skin tingle everywhere they touched. I didn’t want to take them off so I pulled my sweat pants back on wearing them the remainder of the day Saturday and all day Sunday.

Mom was home that weekend and commented on my smile and good mood. Sis gave me a smile as if she knew I was wearing her panties, though she never said anything about them to me.

Monday was a school day so I threw the panties in the hamper. That Saturday, as before, there was a new pair of panties in my basket. I put them on immediately and wore them throughout the weekend. Sis still had not said anything about them.

The next Saturday there were two pairs of panties and a sheer long negligee. I wore the negligee to bed on Saturday and Sunday night. As in the past, I placed the sexy articles in the hamper during the week and they were replaced with new ones on Saturday afternoon. This went on for a few months.

Then one Saturday a nightshirt was included with the panties and negligee. On Monday night, I went to the kitchen to get some juice. As I passed through the living room I noticed Sis was sitting on one end of the couch in just a nightshirt and panties. Her right knee was raised against the back of the couch leaving a good view between her legs. I went back to my room, removed my sweatshirt and pants, then put on the nightshirt she left on Saturday. I already had a pair of panties on.

I went back into the living room and sat on the other end of the couch with my left knee up and leaning against the back of the couch. Sis looked at me, smiled, and said, “Nice panties.”

After thinking a minute for some appropriate comeback, I replied, “I like yours better.” She stood up and slid her panties down her legs to the floor. She then bent down, picked them up, and threw them to me.

“Let’s switch then,” she responded. I stood up, slid my panties down, and threw them to her. I then pulled the panties on that she gave to me.

They were wet in the crotch prompting me to tell her, “There’s a wet spot on these panties.”

She quickly responded, “I’m surprised there’s not a wet spot on yours, didn’t you like them?”

I said, “Yes, I did like them.”

She then pulled on the panties I was wearing and said, "We'd better go to bed before Mom gets home."

I walked to my bedroom with a raging hard-on. As I touched my panties where my dick was poking them I realized there was now another wet spot. I jerked my little dick a few times and it exploded with the best orgasm I ever had to this point making a mess of the panties. I took them off and threw them in the hamper in answer to her earlier comment. I put on a clean pair of panties and a negligee and fell fast asleep.

The following week we were, once again, on the couch in only panties and nightshirts. Sis acknowledged the messy panties from the previous week and said she could do better this time. She then reached her hand between her legs and began to rub herself. This caused her to make many facial expressions followed by a loud moan. She then removed her panties and rubbed them across my face before handing them to me.

I responded by removing my panties and handing them to her before placing hers on me. I was disappointed to see her stand up and walk to her room with my panties in her hand before saying goodnight, although it did give me a good view of her beautiful ass. I went to my room and jerked off in the wet panties. This time I kept them on through the night.

A few weeks later it was Christmas. Mom gave both of us laptop computers. She said work was going well and with the divorce settled, she was in great shape financially. She thanked sis and me for helping her through it all and told us we could start having friends over, having proved ourselves quite responsible. She said it was time to start living a normal life although she had to continue working at nights to get the big tips that helped her financial freedom.

Mandy was the first to bring a friend to the house. She was a beautiful girl named Jennifer. They would spend most of their time in Sis’s bedroom which was next to mine with a “Jack & Jill” bathroom in between. One day when walking into the bathroom I heard Jennifer moaning. I quietly looked past the other door to see Jennifer lying on the bed with her knees up and my sister’s head in between her legs.

Jennifer was facing away from the door, but sis was facing the door. At one point she looked up and saw me. She just smiled and continued to pleasure Jennifer. It was then that I started to realize sis’s actions over the past year. She was treating me like a sister.

That night after Jennifer left, I saw sis on the couch in her favorite spot in her panties and a sheer negligee. I went into my bedroom and took off everything except my panties and pulled on my weekly nightshirt. As I sat on the other end of the couch,sSis moved over closer to me and began to tell me all about her first lesbian experience.

She became so excited about it that she had to grab my hand and hold it on her pussy to show me how wet she was. I said to her, “OK, you win the wet spot contest tonight.” She stood up and pulled her panties down and gave them to me. I took my panties off as she sat down. Then I kneeled down in front of her and put her left foot in the panties. She quickly opened her legs preventing me from placing the right foot in.

As I looked up at her she placed both of her hands on my head and started pulling it down to her lap. I stuck my tongue out to meet her pussy and began licking as soon as I touched it. She guided my head down to her tiny hole where I reached as deep as I could with my tongue. Her pussy was warm and wet. She moved my head up and down her slit. At the top of the slit, I licked side to side and could feel her start to tremble.

Suddenly she pulled my mouth tightly against her clit. She started to tense up, let out a deep long moan and became hot and wet while forcing my face tight against her. My face was soaked with her juices. As I started to lift my head she leaned down and licked the wetness from my face.

Finally, she stood up, grabbed her panties in her hand and walked off to her bedroom. I put the wet panties on, went to my bedroom and jerked off the now biggest orgasm ever in both volume and intensity before falling asleep in a wet and smelly mess.

The following night I found Sis on the couch in another sheer negligee with her new laptop. I slipped on a nightshirt, grabbed my laptop, and sat beside her. She was watching two lesbians in a “sixty-nine” position. She showed me how to get all kinds of pornography on my laptop, almost all of it was women. Then she suggested I should wear a negligee instead of a nightshirt next time. She told me that from now on I could take and wear anything in her bedroom.

With that, she closed her laptop and stood up. I could see she wasn’t wearing anything under the negligee. She asked me how she looked, with which I replied, “Hot, sexy, and beautiful.”

She said, “That’s exactly how I feel.”

“You should feel this way, too.”

“Maybe tomorrow night,” were her closing words as she slowly walked to her bedroom.

We spent two or three nights a week through the remainder of winter on the couch with our laptops viewing porn while dressed in skimpy nighties. Sometimes I would choose the night’s ensemble, sometimes sis would choose. She stopped the Saturday deliveries in my basket insisting that I come to her bedroom regularly to choose my intimate wear.

On one of my first visits to her bedroom, I tried on one of her bras. While I was comfortable with sis when wearing panties and eventually a negligee, a bra seemed different. It really wasn’t functional. It signaled a new meaning in my dressing in women’s intimate clothing. I started to wonder if maybe sis’s reason for having me pick out my own clothing was to make it my decision to continue forward on this path.

Then, again, maybe it simply did not serve a need for her. Either way, I was enjoying this adventure and wanted to take it to the next step so I picked out a few bras to wear when by myself. In fact, I left the one on that I first tried as I carried my weekly supply of intimates to my bedroom. This was definitely a step up as I really felt like a hot sexy girl now. I was also sure that dis would eventually comment when she started seeing the bras in my hamper.

After a month or so of wearing bras, sis replied in her own special way. She surprised me by leaving a bra in my clean clothes basket. It was the sexiest bra I had ever seen and it was heavily padded. It was red with lace along the top of the cups. It had a heart sewn where the cups joined. The clasps were on the back like most bras which I could now hook behind my back. I had to try it on immediately. It felt so good against my chest and the padding made me look like I actually had tits.

I pulled on one of my nightshirts while standing in front of the mirror. The bra made me look like a woman from the neck down. Unfortunately, it was Saturday afternoon. Mom was home, so I couldn’t prance around the house like this. I took the nightshirt and bra off. I had to settle for just panties under my sweat pants until later that night.

When it was time for bed, I wore the new bra, panties, and a negligee to sleep. It became a regular habit after that. Although I thanked my sister a few days later, I still did not wear a bra around the house when she was there, not even when we sat on the sofa together.

Mandy started having Jennifer over more often along with a few of her other girlfriends. She would often leave the bathroom door slightly open when she was licking Jennifer’s pussy. On occasion, she also would also lick some of the others and they would sometimes lick her. However, I never saw Jennifer licking Mandy. One night while we were sitting on the couch I asked sis about this. She said Jennifer told her she didn’t like licking pussy, she just liked having her pussy licked. Sis said she liked licking Jennifer’s pussy and wished Jennifer would reciprocate, but she would wait until Jennifer was ready.

As sis started having more friends over, she started getting invited to their homes, as well. One Friday, she told me she was staying overnight at one of her friends. Shortly after she left there was a knock on the door. It was Jennifer. I told her Mandy was not home. She said she knew that already. She didn’t come to see Mandy, she came to see me.

I gave her a puzzled look as I invited her in. Jennifer said she knew that I knew about her and Mandy’s sexual exploration and she was hoping I would help her out a little. “How can I help you?” I questioned.

She replied, “I’ve never been with a guy and I need to know what it feels like.”

Still quite surprised by all of this I asked, “Why me?”

She responded, “I trust you. You know all about Mandy and me, yet you haven’t said anything to anybody.”

The timing was uncanny. If she had knocked a few minutes later I would have been wearing Sis’s bra and panties much to my embarrassment. I brought her to my bedroom and before I knew it we were ripping each other's clothes off like dogs in heat. Suddenly she stopped, reached into her purse, and handed me a condom.

When I gave her a puzzled look, she took it back stating, “We don’t want me to get pregnant.” She then opened the pack, took out the condom, and started to roll it over my dick. At that point, she commented that she thought I would have a bigger dick. Although my dick was as hard as a rock, the condom was quite loose.

Since I was already on my back, she climbed on top of me and lowered herself on to my little dick. I could hardly tell if I was inside her. She started moving her hips back and forth like crazy. Although we were both excited, neither of us were getting any satisfaction. She was becoming frustrated and I was becoming embarrassed. After what seemed like hours, but was probably only a few minutes, she got up. The condom slid off and was on the bed. She said, “Don’t tell anyone about this, including Mandy.”

I replied, “Believe me; I don’t want anyone to know either.” She got dressed and left.

As soon as she left I took the condom and flushed it down the toilet. I put on a pair of panties, my favorite bra, and a sexy teddy. I sat on my bed with my laptop and watched some porn where a guy with a big dick was fucking some babe. I became wet as hell and finally came with just a few yanks on my little dick. I put away the laptop and fell fast asleep.

As the end of the school year approached and I was quite confused with all that had happened recently, I decided to sign-up for Football. Since Football is an Autumn sport and starts at the beginning of the school year it was necessary to sign-up before the end of this school year. The coach who is a gym teacher and a sports advisor suggested I sign-up for soccer instead. He said at five-foot-two and one-hundred-and-twenty pounds, I would have a much better chance with soccer than football. I took his advice and signed up for soccer.

The summer brought many changes. Sis now had her own car and as it did not get dark until late, we did not spend any couch time together. Both of us spent time at friends. I got a summer job at a local machine shop through a school program. One of the CNC milling machine operators began to teach me how to write programs for his machine. Since I was good at math I became very good at programming. The summer passed quickly.

Two weeks before school started I had to report for soccer practice. The advice given to me at sign-up was good. I fit into the soccer group well. My teammates were similar to me: long hair, thin, fast, and comfortable with their features. There was no competition to bulk up or build bulging muscles. Everyone was easy going and I could be...