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Stage Three Of My Journey To Becoming Joann

"Continuing journey into the world of cross-dressing..."

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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 you for dressing me up and taking me out. I hate to say it, but I really enjoyed the night and can see myself doing this, again. Did you like the party, too?”

“Very much. Michelle and I had a little sixty-nine fun and we both got off. I really really needed that badly.” Suddenly she recalled, “That damn Jennifer used to leave me hanging after I got her off. I took it out on your face one night. I should have apologized and thanked you then.”

“I was glad to help out. I still remember it quite well,” I responded.

Sis said, “I don’t know about you, but I can’t wait to get home and into something comfortable.”

When we arrived home we both went to Sis’s bedroom where she picked out a sheer teddy with a matching bra and panties for me. Then she pulled my hair back into a little ponytail. We both undressed and put on our nighties. Sis took me into the bathroom and helped me remove my make-up. When she was done I went to my bedroom and tried to sleep.

However, all I could do was think about how good it felt being fucked by Bob. My ass was still a little wet from the lubricated condom. Before I knew it the sun was coming up. I would have to put regular clothes on since it was Sunday and Mom would be coming home.

Around noon Sis and I were eating lunch when Mom came in. She sat down with us and announced she had met someone a few months ago at the hotel bar where she worked. He stayed at the hotel there for business several times a year. She waited until now because she wanted to be sure they had a serious relationship. Mom wanted to bring him to the house for Thanksgiving to meet us. Sis and I told her how happy we were that she finally started dating and looked forward to meeting him.

~~~

The next few weeks went fast. I was working all day at the machine shop and practicing soccer at nights. Sis was working and still going to cosmetology school. On Thanksgiving, Mom brought over her new friend. His name was Dave. He was divorced for several years, had his own computer programming business, and seemed like a nice guy. It was the happiest I saw Mom in years.

She made a great dinner and we all enjoyed the day. Dave had to fly back home in the morning so he left shortly after dinner. Mom had a four day weekend from work so Sis and I spent the whole time with her.

We all returned to our normal routine on Monday. I went to Sis’s room that evening to pick out some nightwear for the rest of the week. I tried on a sexy teddy with a matching bra and panties. It immediately made me feel horny so I grabbed the silver bullet vibrator out of the night table drawer. Then I reached into the back of my panties and pushed it into my ass before turning it on vibrate. I gathered all of my choices for the week and walked back to my bedroom holding the remote control while the vibrator was running in my ass.

As I lay on my bed I felt like it was so long ago that Bob’s dick was in my ass instead of the vibrator. Before I knew it I was dozing off when I heard Sis say, “Hey Jo, you better put this stuff away.” I looked around and realized there were bras, panties, and a negligee lying out on the bed. “You don’t want Mom to see this, do you?”

“No, you’re right,” I replied. She picked up the items and put them in the bottom drawer of my dresser. Then she sat on the end of my bed.

“What is that noise?” she asked.

“What noise?” I asked.

She pushed me over on my side and saw the remote wire hanging out of my ass. With a rather unpleasant look on her face, she responded, “Is that my silver bullet in your ass?”

“I’m sorry, Sis. I need to get off.”

“How long have you been using a vibrator?”

“I guess about six months or so. I always wash it off real good. It’s not like I can go out and get one somewhere. You told me I can come to your bedroom anytime I wanted to get anything. Please, don’t be mad at me,” I begged.

Sis cracked a little smile, “I forgive you. You keep it. I’m going to have to take you out so we can both buy some new equipment. What else have you had in that cute little ass of yours?”

After a few moments, I looked at her and replied, “Bob.”

This time she gave me a huge smile and said, “I had a feeling you got into something at the party. Or should I say something got into you. You’re going to have to tell me all about it tomorrow night. I have to get to bed before Mom gets home. I’ll see you on the couch tomorrow.”

With that, she tugged on the wire a little, shifting the bullet in my ass. As I squirmed she could tell I was getting close so she reached over and jerked me off a few minutes until I came like crazy in my panties. “It’s a good thing I do the laundry,” she said before going back to her bedroom. I turned off the vibrator, but left it in my ass with my cum soaked panties on and fell asleep.

The next night I got home from school by 9:00. Sis was already on the couch in a nightshirt watching a DVD of a woman pushing a vibrator into another woman. I went to my bedroom, changed into a nightshirt and a bikini panty, and then went to join Sis on the couch. She turned down the volume on the television before asking me to give her all the sordid details of my experience with Bob.

As I started telling her, she kept prompting me for every little detail. I told her how he gently entered my ass and how I could feel each nub of the condom rubbing across my sphincter. I told her how he picked me up off my feet so the entire weight of my body forced his dick deep into my ass. I described how I came without touching myself and had to lick my fingers to keep her dress clean. She then replied, “Thank you for being so considerate with my dress. Maybe you could take care of one more thing for me.”

“Sure, what do you need?”

Sis spread her legs revealing no panties and a vibrator in her pussy. “Help me with this,” she said as she turned up the volume on the television to hear the woman moaning.

“What would you like me to do?”

She slid down the couch lying completely on her back with her feet on my legs and desperately replied, “Use your imagination.”

I leaned over and started moving the vibrator around in her pussy. She began moaning lightly, moving her hips, and spreading her legs further. After several minutes I could see she was trying to reach an orgasm without success. So I leaned up more and started licking her clit while moving the vibrator in and out. The volume of her moaning rose along with her hip movement.

I worked my tongue up and down her slit from the vibrator to her clit. It was hard to tell if it was the vibrator trembling or her body. She grabbed my head with both hands pushing my face hard against her clit while raising her body. Then she let out what was almost a howl as she orgasmed to another planet.

When she finally started to relax her hold on my head she declared, “Holy shit Joann, you don’t know how bad I needed that. Thank you so much.”

“You’re welcome, but I probably owed you that for last night,” I said as I pulled the vibrator from her sopping wet hole. She took the vibrator from my hand and placed it in her mouth licking it clean.

She let out a little smile as she said, “We’re even.” She slid back up to a sitting position at the end of the couch and pulled her shirt down as she licked her lips. “Mom is working Sunday so we can go shopping. I’d like to take Joann. What do you think? You know everybody at the Halloween party thought you were a girl. It would be easier to shop for lingerie as a woman than a man and much more fun.”

“Let me think about it,” I answered. Although, I was already getting excited at the prospect of such an outing. I think I already knew my answer was going to be yes. Sis removed the DVD and turned off the television as we both headed for our bedrooms. I could still taste her juices in my mouth and on my lips, as well as being quite wet myself.

When I reached my bed I started jerking myself off until I came in my hand. Then I put my hand up to my mouth and licked it like I did that night with Bob. It wasn’t bad I thought. I could suck a dick and swallow if it ever came to that.

After my soccer game on Saturday, I noticed Sis was waiting by the parking lot. “Well, is Joann going shopping with me tomorrow? Does she want some new sexy things to wear?” she questioned me.

I answered her, “Yes, Joann will go shopping with you.”

“Good. You better get some cash today unless Joann is going to use Joseph’s debit card which could cause some problems. Mom is leaving for work around noon tomorrow. I will leave some things in the bathroom for you in the morning. You’ll need to shave everywhere, then shower and wash your hair around 11:00. Leave your hair wet. I’m going to stay over Michelle’s tonight.” She gave me a little peck on the cheek, then left.

I went to the bank and withdrew five hundred dollars. I wanted to have enough money to pay for some of Sis’s things, as well, since everything I had so far was from her. It was time for me to pay my share. When I arrived home Mom was making dinner. We sat and talked for a while about my job, school, and soccer.

During dinner, she asked me how I liked Dave. I told her it was good to see her so happy and if Dave was the reason, then I liked Dave. Then she asked how I felt about him spending Christmas with us. I assured her, “That would be great.” After dinner, I helped Mom clean up the kitchen and then sat in the living room watching television until I went to bed.

When I got up in the morning I noticed that Sis left some clothes in my bottom drawer for the afternoon. I did my weekend chores before telling Mom I was taking a shower. She said she was leaving for work in a few minutes and to tell Mandy that she would be home around midnight.

I went into the bathroom and locked both doors. There was a ladies razor, shaving cream, bath gel, and lotion on the sink as Sis promised. I started by lathering and shaving my legs, arms, chest, face, and underarms. Then I got into the shower where she left shampoo and conditioner. I washed my hair first followed by the rest of my body. As I was drying off there was a knock on the bathroom door.

“It’s me, Mandy.” I unlocked the door and she came in. She took my towel away from me and wrapped it around me from my chest down. “Come into my room so I can fix your hair.” She blew dry my hair as she created some bangs in the front, then pulled it back into a ponytail. “Your hair is getting long and easier to style. Go put the clothes on that I left in your drawer while I take a shower.”

As I pulled out the clothes I realized she left me a thong. Although I saw them in her drawers before, I never wore one of them. I had to find the tag to figure which way to put it on. This was a new feeling. My ass cheeks were exposed and I could feel the back of the thong on my butt hole. Then there was a pair of pantyhose. This also took a little work to get on. But, it was worth it. They felt so good on my legs and seemed to warm them.

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The bra was padded with full coverage cups. The jeans had a slight stretch to them and were very tight. The pantyhose seemed to help the jeans slide on. The zipper was much shorter than my regular jeans and they only came up to my hips. Finally, the shirt, or should I say blouse, was tight with a stretch band along the bottom. The buttons were on the wrong side making it a little difficult to fasten. As I walked toward the bathroom I could feel my whole body tingle as the pantyhose caressed my legs, the thong tightening between my cheeks, and the blouse pulling along my bra.

Mandy yelled, “I’m almost ready to do your make-up, Jo.” I walked into her room as she was drying off and watched with delight as she started dressing. She looked so hot in a thong. I helped her with her bra by hooking it in the back for her. She suddenly said, “I almost forgot. I have a pair of falsies with adhesive on them. Let me put them on you.” She unbuttoned the top of my blouse, reached in and inserted a falsie in each cup, then positioned them in place. “Sit at my vanity so I can do your make-up,” she instructed.

It only took her about ten minutes to do my make-up still in nothing but her bra and panties. Then she finished getting her clothes on as she told me to pick out a pair of shoes to wear. I found a pair of black open-toed shoes with a single strap and a short heel. Sis thought it was a great choice so I put them on.

They weren’t quite as comfortable and easy to walk in as the flats, but I thought I could handle them. Sis picked out a purse for me and filled it with some needed items. She told me to get my money and put it in the purse. She grabbed two black furry coats and we were ready to go shopping.

Sis’s car was in the driveway so it was a short walk to get into the car. I was a little nervous one of the neighbors might see me, but I didn’t see anyone outside. We had to drive about thirty minutes to the mall so I felt we were a safe distance from home. As I got out of the car and started walking toward the mall entrance I realized I still needed to work on my walk. Sis started giving me some advice, “Move your hips a little from side to side, but not too much. Don’t hunch. Keep your chest out, be proud of it.”

I started to pay more attention to how Sis walked as I tried to imitate her. It was making me feel more sexy and I could feel my ass sliding against the back of my jeans with the thong in my crack. I was almost disappointed when we reached the lingerie shop. However, that changed quickly when we walked in and I saw the beautiful selection. As I looked around there were women everywhere occupied with looking at the intimates. We blended in and I almost immediately felt comfortable.

“Well, do you see anything you like?” Sis asked. “How about these panties?” She started picking some up and laying them out. “Pick the ones you like and I’ll check the sizes.”

I must have picked up ten pairs of various styles of panties. Then we found some bras, a few short teddies, and a long sheer negligee. I also picked out a skimpy sexy girdle. Sis picked out some things for herself. When we reached the check-out I told her I was paying for everything to make up for the years she let me use her things. She smiled and said thank you.

Next, we walked a few stores down to a chic women’s clothing store. We picked out several jeans, blouses, and a few dresses. Sis said, “Let’s go try these on.” I don’t know why it didn’t occur to me that we would have to try on clothes. As I looked at Sis with a very nervous look, she comforted me with, “Don’t worry, it will be alright, just let me do the talking.”

We walked into the dressing area and the attendant asked how many items. Sis explained that we were sharing a dressing room and we had ten items between us. I guess this is normal since there was no objection. As we started undressing and trying on the clothes I became comfortable and started having fun. We helped each other dressing and undressing.

I learned I was a size 10 the same as Sis. We ended up keeping everything we brought into the dressing room. Again, I paid for it all. We...

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