Stage Four Of My Journey To Becoming Joann

Close Up

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 first thought was he had changed his mind. My heart started pounding as I read the text. His roommate was going home for the holiday and Bob wanted to know if I could stay for the whole weekend. Soccer was over for the year, the semester was over on Wednesday, and I didn’t have to work on the weekend. I immediately replied to his text with a simple yes. A minute later he responded with, “Great, I can’t wait, see you at eight,” along with his address. My two-hour evening class seemed like five hours as I couldn’t wait to get home and tell Sis about my now extended weekend. I wanted to get started planning as soon as I could. When I finally got home, Sis was sitting on the couch in a nightshirt waiting for me. I told her I would be back as soon as I got changed. I went to my bedroom, tore off my clothes, and pulled on a pair of boy short panties with a satin nightshirt. As I entered the living room I blurted out, “I’m going to spend the whole weekend at Bob’s.” “You’re kidding me?” replied Sis. “Now we’re really going to have to pick out some things. I’m also going to have to give you some lessons putting on your own make-up and doing your hair. When do you finish school?” “I have my final exam Wednesday night and I’m done the semester,” I answered. “We’re going to have to pick out clothes tonight. Tomorrow night we’ll work on make-up and hair. Let’s go to my bedroom.” Sis grabbed my hand and pulled me to her bedroom. She opened the drawer where we put the clothing we bought the past weekend. “Let’s lay all this stuff out on my bed so we can decide what you’re going to take.” We sorted through the items picking out the short black dress, two bras, three pair of panties, the sexy girdle, two tops, and two pair of jeans. Sis went in her drawers and picked out a pair of dark pantyhose. Then we looked in her closet for a pair of heels, a pair of flats, and a pair of pink sneakers. She folded up most of the items and placed them in a small carry case. We looked through her jewelry box and selected a necklace and bracelet which she placed in a small clutch. “It’s getting late,” Sis exclaimed. “We better get to bed.” As I went to my bedroom I thought about how much I had to do by Friday. The week should go fast with so much to do and not much time. I opened my laptop and went on the internet as I lay on my bed. I started looking at sites on anal sex so I would be ready for Bob. A few of them suggested an enema before sex to “keep it clean”. This seemed like a good idea and there were a few methods of doing it. I liked the idea of the douche bag, but where would I get one. I wondered if I could get one at Fantasies that Sis and I went to on Sunday. Maybe I could go there on Thursday night. I put away my laptop and went to sleep in my silk nightshirt and boy short panties. Tuesday night I got home from work before Sis. I put on a pair of new bikini cut panties with lace trim around the legs and waist followed by a heavily padded bra. I wore an old nightshirt in preparation for the make-up and hair lessons. While waiting for Sis to get home I went on the internet to explore more sites for anal sex and tips on cleaning myself out. There was all kinds of information on douche bags, how to use them, and what to put in them. Suddenly I heard Sis yelling, “I’m home. Are you ready to get started?” I walked into her Magosa Escort room as I said, “Ready when you are.” She had a bag of make-up, nail polish, lipstick, mascara, and hair clips. She pulled me over to her vanity and sat me down on the stool. Then she proceeded to show me how to apply all the items she purchased. It took almost two hours before I could start doing it myself. My hair was much easier. I hadn’t cut it in over a year and it was quite straight. She showed me how to pull it back, clip it, and put it in a cute ponytail. “Let’s go in the bathroom so I can show you how to remove all of this and clean your face.” She reminded me that Mom would be home soon. She told me I would also have to clean my face and redo my make-up a couple of times when at Bob’s. “I will help you get ready on Friday night, but you’ll be on your own after that.” It only took about twenty minutes to clean-up. Then she went to her room and brought back a make-up case which she filled up with everything I would need. I was starting to get nervous. It was a lot of stuff. Wednesday night I went to school and took my final exam for the semester. Thursday night Sis had to go to school. I got home before 6:00, so I quickly undressed, put on a bra and a thong, then a pair of jeans and a blouse. I found the make-up case and put on some make-up and lipstick before putting on a pair of flats from Sis’s closet. Finally, I put on one of her coats and headed out to the car. I drove to Fantasies which was almost twenty minutes away. Fortunately, they were still open until 9:00 and it was only 7:30. As I passed by the counter I noticed that the same girl that was there Sunday was working, again, tonight. She gave me a big smile and asked, “Can I help you, sweetie?” I stopped like a deer in the headlights. She stepped from behind the counter, walked up to me and rubbed my right cheek with her finger. “Your make-up is a little smudged. That’s better. Now what can we get you tonight?” she asked. I still wasn’t sure if she knew I was a cross-dresser or not, but I didn’t have a lot of time. Finally, I thought to myself, ‘What’s she going to do, call the newspaper.’ I responded, “I’m looking for a douche bag.” in my softest voice. She took my arm and walked me over two aisles where she picked up a package. As she handed it to me she said, “I think this is probably the one for you. I highly recommend it and have the same one at home. I know you’re going to like it. Do you need anything else tonight?” As I shook my head no, she took my hand and walked me back to the counter. As I paid her she said, “I hope I see you, again. My name is Dawn. I work Sunday through Thursday in the evenings.” When I got home, I saw Sis’s car in the driveway. She was on the couch when I walked in and promptly asked, “Where were you tonight?” Then as she noticed I was carrying a package she inquired further, “And what do we have here?” She grabbed the bag from my hand and pulled out the box. She smiled and said, “Is this for Friday night? It’s probably a good idea if it is.” “I’ve been doing some reading o line,” I replied. “I want to be clean inside and out when I go to Bob’s. I don’t want to gross him out.” “I’ll help you with it tomorrow night when we get you ready for the big weekend. You did a pretty good job on your make-up by yourself tonight. But, you better get it cleaned off and fix your hair back,” she advised me. I went to the bathroom, removed the make-up, removed the ponytail, and brushed my hair back to my normal male style. Sis and I sat on the couch for a while and talked about tomorrow night. I was still in my jeans and blouse. She was wearing a nightshirt. “I’ll be home by five,” Sis assured me. “Make sure your home Kıbrıs Escort by then, too. We have a lot to do if you’re going to get to Bob’s by 8:00. We better get to bed.” I went to my bedroom and changed into a long satin nightgown with a bikini panty and matching bra. I wanted to be comfortable and get some sleep. The next day I left work an hour early so I would be home by 5:00. True to her word, Sis was already home and had the carry case, make-up bag, and the clutch on her bed. She yelled to me, “Get your clothes off so you can shower and douche.” I went to my bedroom, stripped off my clothes, and walked into the bathroom. Sis had the bag hanging on the back of the door into her room and was holding the hose. “Turn around,” she said. I turned my back toward her. She pushed the nozzle along the crack of my cheeks and fished a little to find my ass hole. Then she gently pushed the nozzle into my ass. “Here it comes,” she warned. Suddenly, I felt the warm liquid filling the inside of my ass. There was a strange sensation taking over my body. My dick was getting hard. When it finally stopped, Sis said there was almost two quarts of soap and water mixture in my ass. She pulled the nozzle out and told me to hold it as long as I could before expelling it into the toilet. When I turned around she saw my hardened dick and said, “Are we going to have to take care of that before you go?” as she shook her head and walked into her room. I closed the door and tried to hold the solution in my ass as long as I could. Finally, I had to sit on the toilet and push it out. I couldn’t believe the feeling as the liquid gushed from my ass. Sis yelled through the door, “Get in the shower. I left some good shampoo and conditioner for your hair. Make sure you shave everywhere, too.” I spent the next thirty minutes washing and shaving. When I finished I stepped out, dried off, and wrapped the long towel around my chest letting it drape to my knees. Sis directed me into her vanity chair where she started by blow drying and styling my hair. Then she instructed me to take off my towel and lay on my back on her bed. She sprayed the medical adhesive we bought at Fantasies on my chest and then on the back of the breast forms. After a few minutes, she carefully placed the forms on my chest and told me to lie still while the adhesive dried. She painted my toenails and fingernails with polish as I waited. After the polish dried, Sis got the skimpier black bra we purchased at the mall. She sat me up, pulled it on, and hooked it as fast as possible saying, “I don’t want them to shift before the adhesive dries completely.” I couldn’t believe how real they felt and looked. Then she handed me one of the thongs I picked out at the store and told me to put it on. As I pulled it on she said, “We better go to back to the bathroom.” As we walked into the bathroom I realized the reason. I was getting hard, again. Sis pulled me to the sink, pulled the front of my thong down, and started jerking me off with one hand while cupping my balls with the other. “Tell me when you’re getting ready to come,” she demanded. I put my hands around the back of her neck locking them together, leaned back slightly, and pushed my dick into her kneading hands. She started moving her hand faster as she sensed the excitement she was causing. As usual, somehow I got past the fact that this is my sister that has me so aroused and bringing me to a great orgasm. I started to cry, “I’m almost there.” She grabbed a wet washcloth that was on the sink with the hand that was on my balls. “I’m coming!” I exclaimed as I shot my load into the washcloth. “You sure come a lot with that little pea shooter!” Sis replied. I could see it dripping on her Lefkoşa Escort hand and through the washcloth as she reached into the sink to wash everything off. Then she rung out the washcloth and gently wiped my dick clean. “That should calm you down, young lady,” as she pulled the thong back up into place. She squeezed some lotion into her hand and rubbed it on the back of my neck, back, ass, legs, and my stomach. We went back into Sis’s bedroom. She helped me put on the black pantyhose followed by the short and tight black dress. Sis had to pull the zipper up since it was on the back. She put a couple of hair clips in my hair, a necklace around my neck, and a bracelet on my left wrist. I put on a pair of the highest heels I’ve yet to wear. Last, but not least, we finished the make-up, lipstick, and eyeliner. I was dressed to kill. Sis finished me off with a touch of perfume behind each ear and a kiss on the cheek. “You’re going to have to fill me in on everything Monday night. Here is your coat. Everything is ready on the bed. Your cell phone is in your clutch. Are you nervous?” “Just a little bit,” I replied. “My heart is beating like a drum. I’ve never been so excited. Thank you so much for helping me out tonight. I don’t know what I’d do without you.” I put the make-up bag in the carry bag, slung it over my shoulder, grabbed the clutch, and walked out to the car. I really felt sexy. My breast forms jiggled slightly in the skimpy bra and pushed the top of the dress outward. The pantyhose glided along the inside of the tight dress while the thong was separating my ass cheeks. I was adjusting to the higher heels. As I stepped out the front door I was welcomed by the cool air blowing up my dress. I don’t think I ever felt better walking in my life. I opened the back door and put my bag on the seat. Then I closed the back door and opened the driver door remembering how to bend my legs with my knees close together as I slid into the driver’s seat. I had already entered Bob’s address in my GPS last night. It would take forty-five minutes to his apartment. As I backed out of the driveway I realized that there was a learning curve to driving with high heels. I knew that I would handle it though. Unlike recently, I was feeling more comfortable dressed in public. I pulled in the parking lot of the apartment complex, stepped out of the car, grabbed my bag, and walked toward the unit with his number on it. I passed by a couple walking out of one of the doors. Smiling, I quietly said good evening to them. Then I approached the door and rang the doorbell. Bob opened the door, “Hello, Joann. I’m so glad to see you, again.” Then he gave me a big hug and a kiss on the lips. I could feel his excitement and see it on his face. My nervousness immediately disintegrated. I stepped in as he shut the door. After setting my bag on the floor and my clutch on an end table I put my arms around him, squeezed him tight, and gave him a kiss that included most of my tongue. His arms reached around my waist as he reciprocated with his tongue in my mouth. “I’m glad to see you, too,” I gasped as I could feel his chest against my tits. I reached behind me and put my hands over his pulling them down across my ass. “I’ve been looking forward to this weekend so much,” I said without reserve. When we finally released our grip on each other, I removed my coat. Bob immediately reached for it and placed it on a chair in the corner. As he turned back toward me he lamented, “You are stunning! You look better than I remember last time or could ever imagine. Can I get you a glass of wine?” “Yes, that would be nice,” I answered as I sat on his couch and modestly crossed my legs. Bob went to the kitchen and poured two glasses of white wine. He handed me a glass before turning on some soft music. Then he sat next to me with his glass in one hand and placed his other hand on my knee. “So your roommate is away for the holiday?” I said. “Yes, Jimmy went home to be with his family for the holidays. We got a great deal on this place. It was almost…

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