Stage nine of my journey to becoming Joann
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Stage Four Of My Journey To Becoming Joann free porn video
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 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 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 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 as cheap as living on campus in a dorm and much more private,” Bob explained. “I work part-time at a clothing store and this is their busiest season so I had to stay here for the holidays. Now I’m glad I’m staying.”
I asked, “Is that the same Jimmy that came to the party with you? I don’t think he liked Amanda and me very much.”
“Yea, that’s the same Jimmy,” responded Bob. “It’s not that he didn’t like the two of you. It just took him by surprise and he comes from a very conservative environment. He still doesn’t believe both of you are guys.”
“It doesn’t bother you?” I questioned. Bob answered by taking both our glasses, setting them on the end table, and kissing me full on the lips. I could feel his hand rubbing the inside of my thigh. I responded by putting my arm around his neck. He worked his mouth from my lips to my neck leading him along the trail of perfume that Sis strategically applied on me.
“You smell so good,” he exclaimed as he continued to kiss me all over. My whole body was beginning to tingle. I rolled up onto his lap facing him with my knees straddling his legs as I kicked off my heels. I wrapped my hands around his neck as he moved his hands from my waist to my bust back and forth. I leaned my head back as I felt the electricity from his hands on my body. He started to concentrate on my tits as he noticed my response to his touch.
I moved my knees open slowly sliding down his legs releasing my hold around his neck until I was in a kneeling position. With my knees on the floor, I took both hands and pulled his nylon sweat pants down to his ankles followed by his boxer shorts. Lifting his feet, one at a time, I removed his lower clothing. Then I pushed his legs apart revealing his beautiful dick which popped up like it was looking for me. I leaned down and gave it a little lick with my tongue. I could hear Bob sigh as he slid toward the front of the couch a little giving me better access.
I licked around the top of the head and down the shaft where I could feel the vein that was facing me. He was starting to develop some pre-cum that was turning me on. I opened my mouth and began to descend down the shaft until his dick was against the back of my throat. Then I withdrew slowly with my lips pursed tightly around the shaft and my tongue dragging along his vein.
As I reached the top I wiggled my tongue on the end of his head still keeping my lips wrapped around it tasting more of his pre-cum. Then I started another descent down his shaft as far as I could, followed by another slow withdraw, again, using my tongue to massage his vein. Bob put his hands on my head on the next cycle. As I reached the bottom of his shaft he pushed my head down wanting to go further. I could feel the end of his dick pushing into my throat. I started to gag and cough a little.
Bob started to apologize as he removed his hands from my head. I released his cock from my mouth to look up at him and say, “That’s okay, I’m new at this. Will you let me practice some more?”
He grinned from ear to ear as he said, “You are so hot. How did I get so lucky?”
I leaned down and resumed my slow descent on his shaft, each time trying to take it into my throat. Then I tried breathing in before going down so I could hold my breath when I tried entering onto my throat. This was a little better, but I still couldn’t stay down too long. His dick was becoming coated with my slobber which also made it easier to push into my throat. I was starting to get into a rhythm when I could hear Bob cry, “I’m going to come soon.”
I tightened my lips a little forcing my tongue against his vein while cupping his balls in my right hand. He started to pant and tense up. I could feel his balls start to pulsate, and then I felt his vein pulse as his cum pumped through his dick and into my mouth. I pulled back slightly so I could let it fill my mouth and taste it. His hands were on my head, again, this time holding my head still as he shot his loads of come into my anxious mouth.
I pushed his dick back into my mouth a little further and held my hands around his waist as I could feel his whole body shudder several times as he completed his release. I held still in that position with my lips securely around his dick. I could feel an occasional twitch of his aftershocks on my tongue from his vein.
His tension started to subside slowly as his dick began to shrink in my mouth. After a few minutes, I pulled my mouth from his dick slowly while keeping my lips tightly sealed. As I raised my head I could feel and taste my mouthful of cum. I moved my tongue around in my mouth to feel the texture of it before taking a big swallow. Then I licked around my lips with my tongue to clean them of any cum that started to escape.
Bob pulled me up next to him cuddling me as he kissed me behind my ear and stroked my long hair. We just stayed like that for close to an hour as he now rubbed his hand on my side from my bust to my thigh. As I savored the taste of his come in my mouth, I realized I was quite wet myself from my own pre-cum.
Bob’s hand stopped rubbing me as I sensed he was dozing off. I reached over to the end table and took a few mouthfuls of wine listening to the soft music that seemed to disappear during my first experience at giving a blow job. It was another major step for Joann. As Bob started to open his eyes and move a little I suggested we retire to his bedroom. He smiled broadly as I pulled him up. I told him I would need to use the bathroom to freshen up and would like a little more wine. He filled my glass and told me he needed to use the bathroom first. I sat back on the couch and enjoyed my wine. I felt so comfortable, relaxed, and natural.
When Bob returned, he went to the refrigerator getting some fruit and cheese. I thought to myself, how romantic. We sat and talked for thirty minutes as I finished the bottle of wine he opened on my arrival. He leaned over and kissed my cheek. I smiled as I stood up and walked to get my bag. “I won’t be long,” I assured him. “Which way to the bathroom?”
Bob took my hand and led me to the bathroom. He pointed to his bedroom door, “That’s my bedroom there. Take your time.”
As I stepped into the bathroom I realized my zipper was on the back of my dress. I called to Bob, “Could you unzip me?” He quickly returned and pulled my zipper all the way down for me. He watched as I let my dress drop to the floor and step out of it.
“You’re amazing, I can’t believe how beautiful and sexy you are,” he said as I shut the door. When I saw myself in the full-size bath door mirror I thought to myself, he’s right. I look and feel hot. I rolled down my pantyhose, unhooked my bra, and pulled off my thong which was now tight in my ass. The adhesive on my breast forms was impressive. I felt like I had real tits. They were firm yet hung a little without my bra on.
I pulled out an above-the-knee sheer teddy with a matching bra and panty that Sis must have picked out. The bra was light and skimpy so I really appreciated the adhesive now. The bikini panty had some small ruffles and was firm enough to hold my goods in. I pulled the teddy over my head. The pink material closely matched my finger and toenail polish. I touched up my make-up and put on a little more perfume. Then I pulled out the “bedroom purse” Sis packed me. It had condoms, lube, and tissues in it. I took the tube of lubrication, squatted down, and squeezed some of it into my asshole before placing it back in my case.
I walked into the bedroom, put my travel bag in the corner, and put my purse on the end table. Bob was lying in the bed with a blanket on. As I lay down in the bed he turned off the light. He put his arms around me pulling me into him. I could feel he was completely naked. I put my arms around him. We began kissing with our tongues moving in and out of each others mouth.
I reached down and took his dick in my hand. It was starting to harden a little. I moved my lips to his neck, then to his nipples. He trembled slightly as I licked his nipples. Then in one continuous motion, I dragged my tongue from his nipple across his stomach and pelvis to his dick.
I began licking up and down his shaft like a lollipop. As it began to grow I started licking the head of his dick paying particular attention to the small slit. After a few minutes of licking, I could begin to taste his pre-cum. I felt the same urge I did earlier and had to push his dick as far into my mouth as possible. This time I had a better angle and was able to take him into my throat within a few attempts. My lips were feeling his balls on my downward motion indicating I was fully consuming his hot meat. He let out a little moan.
I sat up and reached for my little purse, removing a condom. I used my teeth to rip off the wrapper before rolling the condom over Bob’s dick. Then I straddled him on my knees moving up his body until my ass was above his erect dick. I lowered myself until I could feel his head between my cheeks before lining it up with my waiting hole. Then I slowly sat as I could feel the tip of his dick push into my sphincter forcing it open. I could feel the ribs of the condom sliding through the tight ring of my ass.
Once into me an inch or so, it was pure pleasure after that. I put my arms up and around my head as I continued to almost suck his dick into my ass. I could feel the heat of his cock warming my insides. As I let the muscles in my legs relax the full weight of my body was now pushing my ass to consume his dick completely.
I could feel his balls against my cheeks. I slowly lifted my body up feeling his dick withdraw from my ass until only the head was still inside me leaving me with an empty feeling that demanded refilling. I lowered back down in aTo continue reading this story you must be a member. Join for FREE here.
Nova
- 09.08.2020
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