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 a hard-on as the warm liquid fills my bowels. I cleaned my face as I held the water inside me for almost ten minutes. Then I sat down on the toilet and expelled the entire contents. I always feel cleaner after douching my asshole.

Leaving my breast forms on, I changed my slinky bra to a full coverage one for running, followed by a full coverage panty. I put on my soccer uniform and shoes, combed and pulled my hair back into a pony tail, and grabbed my bag with clothes for after practice. I was out of the house and on my way before Sis got home.

When I pulled into the parking lot at the soccer complex, there were several gurls standing around. They all greeted me as I got out of my car. One of the not so passable ones, Jamie, asked if we could move Gurls Night to Saturday night instead of Monday. This would give us more time than after practice.

After a few minutes of discussion, I agreed to not only move it to Saturday, but make it a pajama party for those who wanted to stay overnight. Everyone was excited. Chrissy and I went to the locker room together, as usual, to stow our clothes before going out on the field. As we loosened up, I noticed Donny in the spectator area. We exchanged waves. Now, I was excited.

After practice, I showered, combed my hair, put on my make-up, and perfume. I had packed some sexy clothes the night before: a short pleated skirt, a peasant style sleeveless strapless blouse, strapless bra, and black lace bikini panties with red trim. Since I was hoping Donny would be here tonight and I know his dick is on the soft side, I brought a five-inch butt plug in my bag.

I put a dab of lubrication on the tip and set it upright on the bench. Then I pulled my panties down and sat on it pushing it into my ass. It had a tee-handle that was hidden by my cheeks when fully inserted. I pulled up my panties and pulled my skirt back into place. When I walked into the locker room, I got several compliments, hugs and kisses.

Chrissy said, “You go, girl. I can’t wait until the pajama party. Now be careful tonight.” When we walked out the front door, Donny was standing in front of the other guys. He greeted me with a kiss on the lips. As I looked around, I saw Kevin and Steve. They smiled, but kept their word and didn’t say anything to arouse suspicion of our previous gang bang.

Donny took my bag and walked me to the car. Then he asked, “Can we go for a drink?”

I responded, “How about your place?” He looked a little surprised, but quickly answered with a yes. “I’ll follow you,” I said. It was a twenty-minute ride to his apartment. I parked next to his car in the parking lot. He came around and took my hand as I got out, keeping my legs closed as Sis taught me so long ago. Donny held my hand all the way to his door. I felt like a school girl. Of course, a naughty one with a butt plug.

His apartment was nice. It looked like he lived alone which he confirmed later, as we talked. He opened a bottle of wine and poured us each a glass. He turned on some music, dimmed the lights, and sat next to me on the couch. It was so romantic. It didn’t take long before I was in his arms and his hands were all over me. He asked me if I would like to go to his bedroom. I just gave him a huge smile and picked up my bag.

He took me by my hand to his bedroom. As we sat on the bed, I pulled his shorts down. I think he was turned on by my aggressiveness. I started stroking his shaft while he started rubbing my shoulders. It was as I remembered, large yet soft. I moved back a little and put my head down to lick the tip of his dick. He let out a small moan.

His pre-cum was getting me hot and I started taking him into my mouth. He moved his hands to my head signaling that he wanted more. I took a breath, silently said, “ahhh,” and pushed my head down forcing his dick into my throat. His dick was made for my throat. While it was one of the largest I ever swallowed, it was softer and did not hurt like Bill’s. It easily slid in and out. As I pulled up, the slit in the tip of his dick oozed out his thick and sweet pre-cum.

My mouth became wet, lubricating his shaft, making the next entry into my throat easier than the first, also adding to the taste. We were both building our lust as I continued to deep throat him, then alternating with licking his tip and sucking it on the way back down. The butt plug in my ass reminded me that I wanted more than a mouthful tonight prompting me to whisper, “I want you inside my ass.”

He answered, “I’ve dreamed of this all my life.”

I pushed my head down for one last throat fuck hoping to make him a little harder. I was worried that I wouldn’t be able to get his somewhat soft dick into my tight ass. I forced his dick as deep into my throat as possible and held it there for the better part of a minute before pulling off. I quickly reached into my bag and pulled out the extra large size condom that I bought a few weeks ago in anticipation of this night. Opening the pack, I couldn’t believe how large it was.

As I pulled it over his shaft, it reminded me of a few years ago when Jennifer put a regular size condom on my dick and it came off almost immediately. The large condom did not restrict his dick. It was a little loose. I pulled out some lubrication gel which was thicker than normal, rubbing it on the tip and all around the shaft. It clung, rather than ran.

I climbed up on Donny like I was getting on a horse. As hovered above him, I reached behind me, pulling my panties down in the back and pulled the butt plug from my ass, placing it my bag. He looked quite surprised, not realizing it was in me all this time. Easing down on his dick, it began to bend and fold under me. lifted up and reached down attempting to hold it upright as I tried to push it into my ass. Frustrated, Donny had to wrap both of his hands around his shaft.

Easing down, again, his tip pushed between my cheeks and against my hole. He spread my cheeks with my hands behind me lifting up my skirt at the same time. As the tip pushed against my rosebud, his hands kept his shaft erect. I could feel it slowly pushing into my sphincter. I carefully let my weight lower myself onto his dick as he squeezed his shaft tight with his hands so it could not escape forcing it up into my ass.

When he was in far enough, he removed his hands and I sat down completely on his lap. His dick continued to ooze into my ass for another minute or two. I was glad that I had the butt plug in for a while. I don’t think we would have got his dick into my ass if I hadn’t opened it up a little first.

When it felt like it was done pushing in, I started to move my hips back and forth. Similar to my throat, his dick filled my anal cavity, but did not have the familiar brutal feeling of a rock hard shaft. It was soothing and very comfortable. I felt like I could keep it in me forever.

Lifting up and down, I felt like I was jerking him off with my asshole. Instead of his dick sliding in and out of my colon, its skin clung to my insides while I pulled it up and down his inner shaft. I didn’t want to lift too much because I was worried it would pull out and we wouldn’t be able to get it back in. I moved my body up and down in short deliberate movements. I watched his face as he smiled and looked into my eyes with an expression of satisfaction.

He moved both of his hands to my hips and started to guide me back and forth, occasionally prompting me up and down at the same time. I leaned back to try to force it deeper into me with little success. I took his hands in mine and used them to push and pull myself in a steady rhythm. We went on like this for what seemed like forever. Finally, he started to gasp a little. I increased to a frenzied pace feeling his hands squeezing mine harder.

He started bucking his hips and breathing heavy. I pushed down on his groin with all my weight as he finally declared, “I’m cumming baby, I’m cumming!” I didn’t slow down until he put his hands back on my hips stopping my crazed movement.

I sat still for a few minutes as he regained his composure. Then I raised myself up on my knees pulling his dick from my ass and the condom. As I rotated around I could see his dick from the tip to the base was covered with his cum. I lowered my head and put it in my mouth licking it clean. He grabbed my head to restrain me a little. I think he was still quite sensitive. His shaft was warm in my mouth and I loved the taste of his cum. I was convinced that his dick was made for my mouth.

I pulled my panties up and my skirt down, leaving the condom in my ass. I so love the feeling of the lubrication and condom between my cheeks as I walk. As Donny got up and put on his shorts, I put on my shoes and grabbed my bag. He walked me to my car, giving me a big hug, before I got in to head home.

When I got to the house and walked in, Michelle and Sis were sitting on the couch. “How was your night, Joann?”

I replied, “It was okay, but I didn’t get off.”

Michelle said, “Come over here poor baby and let me take care of you.” I looked at Sis. She shook her head with her approval. I walked over to the couch in front of Michelle. She lifted the front of my skirt and pulled down my panties. “My, my, you are a wet little girl.” With that, she put my little dick in her warm mouth. It felt so good as she began to suck it. She wrapped her arms around my waist rubbing her right hand on my backside.

She pulled off of my dick just long enough to ask, “Are you running around with a condom in your ass?” Sis gave me a concerned look as Michelle resumed sucking my dick.

“Jo, you have to stop that. You’re going to get something that way,” Sis warned.

I was going to answer her, but Michelle brought me to a climax as I held her head in my hands with my knees started to buckle a little. She sucked me like a vacuum cleaner swallowing every drop of cum. Then she turned me around and pulled the condom out of my ass. I pulled my panties back up and sat down next to Sis. “As long as the condom is hanging out, I can’t get any cum in my ass. It’s okay. I really like it. Please, don’t get mad.” She hugged me and said she was just worried about me sometimes.

Suddenly, I remembered my earlier conversation with the gurls and said, “Oh, by the way, we’re changing Gurl’s Night out from Monday night to a Saturday night pajama party. Will that be okay? They were hoping to spend more time with us.”

Sis answered, “I guess it’ll have to be.”

Michelle said, “Great, I can’t wait.”

Two weeks later, on Saturday morning, Michelle, Sis, and I went through the house, cleaning one last time. Sis went out to buy some alcohol to stock the bar on the patio while Michelle and I made snacks. Then the three of us got into the big tub in Mom’s old bedroom and took a bubble bath.

We took turns washing each other, playing about. Afterward, we helped each other with our hair, dressed in only our bras and panties. Michelle picked out clothes for all three of us. We were dressed and sitting on the couch when the doorbell rang.

I went and answered the door since I was technically the host. It was Chrissy. I brought her into the living room and introduced her to Michelle and Mandy. Both of them complimented Chrissy on how good she looked. Michelle asked, “Are those tits real?”

Chrissy immediately answered, “Yes. Of course, I have implants. Would you like to feel them?” Michelle didn’t hesitate to take her up on her offer. Girls are so much friendlier and open. Chrissy instantly bonded with Michelle and Mandy.

A few minutes later, the rest of the team started arriving. I introduced everyone as they came in. As the living room filled up, I moved the party out to the patio. A few of the gurls were asking Mandy for tips to looking more passable. She took one of them to her bedroom vanity and showed her how to make-up her face like she did with me a few years ago. When she returned, everyone couldn’t believe the difference. Mandy was the star of the party. She was having a great time taking each gurl to her bedroom and teaching them how to look like a real girl.

Michelle was showing some of them how to walk, talk, and dress. At one point, she even took off all of her clothes on the patio so she could show everyone how girls dressed and undressed. I’m not sure if everyone knew she was a real girl at first, but they sure did after that.

As I sat talking to Chrissy, each gurl came and told me how much they appreciated the party and how much they learned from Michelle and Mandy. Several told me how lucky I was to have a sister like Mandy and a friend like Michelle. I told them I already knew that.

Some of the gurls couldn’t stay for the night and left. By midnight, there were five who were staying. We put two in Mom’s old room and two in the guest bedroom. I asked Chrissy to stay in my bedroom with me. We both changed into nighties and got into my bed. Chrissy spooned up behind me and started stroking my hair. She was giving me goosebumps, but it felt good and I responded with a little sigh. Then she reached over and started rubbing my breast prompting me to push back into her, feeling her tits against my back. This was a new feeling for me, and I liked it.

After a few minutes, I rolled over facing her. She pulled my head toward her chest and I instinctively placed my lips on one of her nipples. Then I pulled her nightie up over her beautiful tits and started sucking on her left nipple. She began to let out little sighs. I moved to her right nipple which made her sigh louder. I knew I had to have breasts like this some day.

I started kissing my way up her breasts, to her neck, and then to her lips. I thought to myself, I was becoming a lesbian. We kissed for a few minutes pushing our tongues back and forth into each others mouth. Chrissy started giving me little kisses on my neck working her way down my body until she shifted around into a “69” position with me. She pulled down the front of my panties and put my little dick in her mouth. I reciprocated pulling down her panties and putting her dick in my mouth. I was surprised. She was well endowed.

Tonight, was another first. I never had a sixty-nine with another dick. It was a great feeling. The more I sucked on Chrissy’s dick, the more she sucked on mine. It was a double pleasure. I felt a little guilty, however, since I had a bigger mouthful than her. I could deep throat her a little, but I was not long enough to reach into her throat.

We were both wet and I was hoping we could cum at the same time. I tried to concentrate on her dick to distract me from mine so I could hold out long enough for a tandem orgasm. As I pushed her dick into my throat, I could feel her suck mine harder. It was as if I was pleasuring myself. I continued to deep throat her with a passion, sensing a response. She was breathing heavier and beginning to quietly moan.

Suddenly, she sucked hard on my dick and made a humming noise. I could feel her tense up and her vein pulse as it pumped her cum into my mouth. I stopped holding back as I let loose with my own cum. We were both sucking cum at the same time. It was amazing. We both laid there with each other's dicks in our mouths for a while.

When Chrissy finally released my dick, she pulled hers free from my mouth and turned around coming back up to me. She kissed me full on the lips, pushing her tongue into my mouth. Although we both swallowed each other's cum, I could taste some of mine on her tongue. I bent down a little and pulled up her panties before pulling up my own. We fell asleep in each other's arms.

We awoke to noise throughout the house. Michelle was in the bathroom showing one of the gurls how to put her hair up without any help. Mandy was in her bedroom giving a follow-up lesson on make-up to another gurl. Someone was in the kitchen making breakfast.

Chrissy got up in her skimpy teddy, walked into the bathroom, sat, and peed, while Michelle and one of the gurls were still in there. The doors to both bedrooms in the bathroom were wide open. As I got out of bed and walked toward my dresser, Chrissy came up to me and gave me a big hug and kiss on the lips saying loudly, “Joann, you were wonderful last night.” She was obviously an exhibitionist.

I put on a robe and went into the kitchen. Jamie and Connie were making a large breakfast for everyone. Jamie was wearing a teddy. Connie was wearing a night shirt. These were the same gurls who had to sneak onto the deck at the bar last month. They both gave me a hug and a kiss on the cheek. Jamie said, “Joann, I can’t thank you enough for inviting us here and helping us. Michelle and Mandy are amazing. I feel so much more confident. How do I look?”

I used a familiar phrase, “You look marvelous. It was my pleasure to have everyone here. Maybe we can do it, again.”

A voice behind me answered, “That’s a great idea. Let’s do it, again, next month.” It was Sis. We all sat and had breakfast before the gurls dressed and left. Afterward, Sis told me she had a great time. “I enjoyed helping and teaching the gurls to look better. It’s the reason I took cosmetology. I wanted to make women look good. Of course, this is a bigger challenge.” We all laughed, but I could see the satisfaction in Sis’ face. She finished off the conversation saying, “Michelle and I would like to come to your first game, if you don’t mind?”

I replied, “Of course I wouldn’t mind. I’d love to have you both there.” I thought to myself that Sis was finally shaking her guilt from helping me on my journey to becoming Joann. I can’t think of my life on any other path.

After helping clean-up from breakfast, I took a shower and dressed in a two-piece bathing suit I recently purchased on line. It was a high-cut bikini bottom and a very skimpy string halter type top. I wanted to lay out in the back yard in the afternoon and get a tan that would leave some girly tan lines on me for a few months.

I didn’t want to wear any breast forms and I couldn’t wear my girdle panty so this was not a “public outfit”. The hormone therapy was growing my breasts to a near “A” cup so the top looked okay. But, I still had a little bump in the bottom that bothered me. Michelle insisted I was the only one that noticed it. She and Sis were going to get some things from Michelle’s house. We agreed that we would all lay out in the back yard when they returned. In spite of the small bump, I felt so sexy walking around in the bikini. Summer adds a new dimension to dressing like a woman.

When they left, I went into my office and sat down at the computer. I typed a letter to Mom. It was time I told her about Joann. A letter was the best way since it would let me carefully choose my words and she would have to hear my entire explanation without stopping me. Sis could also look at it first, so she would know what I was telling Mom. It was important to me that neither Mom nor Sis felt guilty about my choice to become Joann.

I explained that my physical stature was the main factor in the beginning. I didn’t mention Sis’s involvement in my early transformation, only her recent acceptance and support. I wrote that I participated in sports and had started in a man’s occupation, so the presence of a father would not have made a difference.

I finished the letter shortly before Sis and Michelle returned. I asked Sis to sit down and read it. As I watched her read it, I started to worry about her reaction. When she finished it, she stood up with a few tears in her eyes, before hugging me. “Joann, I love you so much. Can I let Michelle read it?” I nodded my head in agreement. While Michelle read it, Sis said, “I was going to ask you if you were sure you wanted to do this, but I think you are.”

When Michelle finished it, she also gave me a hug saying, “You’re the most beautiful person I know, next to Mandy, of course.”

I replied, “Let’s get some sun.” Michelle and Sis changed into string bikinis while I pulled three lounge chairs from the patio out into the back yard. Michelle rubbed tanning lotion on my back as Sis rubbed it on Michelle’s back. Then Michelle turned around and rubbed it on Sis’ back. We spent the afternoon sunning and sipping on rum punches. It was a great weekend for Joann.

Michelle suggested I take a shower while she and Sis made dinner. Then they could shower together after dinner. When I took off my bikini, I had a beautiful tan with a white area on my two breasts and down my pelvis. I loved this look. I trimmed my pubic area with a razor to maintain my small heart shape before using my laser hair remover on my legs. The hormones reduced most of my hair growth, but I still have to shave once in a while just like any woman.

After showering I pulled on a one-piece strapless terry cloth cover-up with no under garments. This was twice today that I was feeling so sexy in summer clothing. The feeling reminded me of the first time I ever put on a pair of panties.

After dinner, Michelle and Sis went to the bathroom together. I changed into a silky teddy ensemble, pushed my old silver bullet up my ass, and watched porn on my bedroom television until I came in my panties. I fell asleep with the television on and the silver bullet still running.

Monday morning I got up, put on a thong, a padded bra with no breast forms, a halter top and a short, but loose, pair of short pants. I wanted to be comfortable since I was expecting to be in front of the computer all day. Just before noon, there was a knock on the front door. It was Bill Simpson, from across the street. He said the mailman must have accidentally put our mail in his box so he brought it over. I told him his timing was good. I was getting ready to stop for lunch. He asked me if I wanted to come over his house since he made a large pot of home made tomato sauce for the week. I said, “Okay.”

We walked over to his house. As soon as we stepped inside I could smell the sauce. He cooked some angel hair pasta and put the sauce on it. After lunch, we sat and talked for a few minutes. Bill said he worked from home, also. He said he’d been lonely since his wife left and thanked me for our encounter last month. It was the only time since his wife.

I could see he was leading into another interlude as he put his hand on my knee. Of course, I was game. After all, he had the biggest dick I ever had in my mouth. I reciprocated by rubbing his upper leg. I could see and feel his oversized member in his left pant leg. It didn’t take much to reach up his short pants to touch it. He was already starting to harden. I helped him pull his shorts down and off. I still couldn’t get over its size.

I leaned down and started licking the pre-cum from his tip. As I started to pull his shaft into my mouth, I remembered it made my throat sore last time. I started bobbing up and down on it to try to get it wet before taking it in my throat. When I thought it was wet enough, I pushed my head down to force it in, but it was still quite painful. I pulled up and worked it in my mouth some more. Bill leaned down and said, “I really want to fuck you.”

I wasn’t sure what to do or say. I sat up and said, “I’m sorry, I can’t do that.”

He responded, “I know you don’t have a pussy, Joseph. But you do have a great ass.” I wasn’t ready for this.

“What are you talking about, Bill?”

“I knew you were Joseph for quite a while. I saw you coming and going in your car at night over a year ago when your mother was still living there. There’s nothing to be ashamed of. You make a pretty girl and this is the twenty-first century. I’m certainly not going to say anything to anybody. I wish my wife had been half as good as you.”

I stammered, “I don’t know what to say.”

He answered quickly, “Say yes, you want to get fucked.”

I knew from the first time I saw his dick that I wanted it in my ass one day, so I said, “Yes, I want it inside me. Do you have a condom?”

“Unless you have some disease, we don’t need a condom.” Bill said, “I told you I haven’t had sex since my wife left. Anyway, I can’t keep it hard with a condom on. I do have some lotion though. Let’s go to my bedroom and I’ll get it.” I followed him up to his bedroom. He pulled a squeeze bottle from a dresser drawer and handed it to me as he laid on his back on the bed.

I squirted the lotion on his tip and shaft, rubbing it up and down like I was jerking him off. Then, I climbed on top of him and pulled my shorts and thong down in the back. His dick was so big, I actually had to lift up a little to get it under me. As I let down a little, I started to wonder if I was going to get it into my tight hole, in spite of his rock hard condition. I had to reach back and pull my cheeks apart to keep them from pushing inward. I could feel the tip of his dick against my rosebud.

As I let my weight down, his tip started stretching my sphincter open to limits never before experienced. It had been a long time since I felt pain or apprehension taking a dick in my ass. I could feel every detail of his tip as it passed through my anal ring. I had to stop and pull out a little, then push it back in. This was required at least a dozen times before I could accept it into my anal canal. When the tip was far enough in, my knees were finally on the bed so I could control my descent by bending them.

After the tip passed through my anal ring, there was some relief as the tip of his dick was larger than his shaft. As I continued to bend my knees to let my body force the impalement, I could feel it inside me. I lifted my hair over my head with my hands. It felt like his dick was in my stomach. I had never been so fulfilled before and it was still pushing up my ass. His eyes were almost closed and he was uttering a subdued moan.

My ass had never been forced open so wide before in my life. I stopped pushing down for a moment. It didn’t seem like we were going to reach bottom. I pulled up a little to feel the lubrication. It seemed like it was there, but my ass was getting so hot inside. I let my weight down, again, and felt his dick move up my ass to a depth I didn’t know possible.

Finally, I felt my cheeks come in contact with his thighs. It was like a submarine in a movie freefalling into unknown depths until it hits bottom. I relaxed my knees and became totally impaled on his huge member. I started squeezing my cheeks involuntarily as if trying to loosen my bowels from around the huge invader. Bill let out a loud moan from the message my colon was giving his dick trapped inside me.

My ass was on fire. My little cock was oozing out pre-cum into my panties. I lifted up a little until I could feel his dick try to slide from my ass, before dropping back down forcing it into its maximum penetration. I couldn’t hold back and exclaimed, “Oh, shit,” as I had an anal orgasm.

I began bouncing up and down with abandon. Bill put his hands on my waist to slow me down a little. The heat in my ass was amazing. I couldn’t get enough of him inside me. Apparently, he too, was feeling the heat as his eyes and mouth was wide open. He began to gasp making small indistinguishable noises before finally declaring, “Baby, I’m coming!!! Oh, yes, am I cumming.”

I could feel his giant member pulsating in my hot tight ass as I leaned back to force it in as much as possible. His hips pushed upward and he was almost convulsing under me. “Ohhhhhh, I can’t believe this,” he cried out as he gave a final push upward before collapsing.

I leaned back on my hands while firmly planted on his cock, my knees still on the bed. My shorts and panties were down my legs just enough that I could see my little cum drenched dick. I could feel his dick starting to shrink a little, easing the pressure inside my colon. Yet, I was still adequately filled. He was as big soft, as most men are rock hard. I could have stayed like that all day, but he started moving his legs after a few minutes.

I pushed my feet forward a little so I could pull my body away from him, in a crab walk motion, freeing his cock from my ass. I thought I was going to have another orgasm as I felt it sliding out of my hole. When the tip of his dick finally popped out, I suddenly felt wet between my cheeks like someone was pulling my enema hose out without shutting it off. My first thought was that I was bleeding. As I looked down, there was a large pool of cum on the mattress. My sphincter must have stayed dilated letting Bill’s cum drip out. What a mess. I raised my one leg over him and sat on the edge of the bed before standing and pulling up my panties and shorts.

I asked him if he had a towel so I could clean up the mess. He responded, “Don’t worry about it Joann, I’ll get it. I think it’s my mess anyway. I’m sorry I called you Joseph earlier. I hope I didn’t upset you. I really want to see you, again.”

I assured him that this was not the last time. He got out of the bed and put his shorts back on walking me to the front door. He gave me a big hug and a long kiss on the lips before saying goodbye.

A few days later, I received a letter in the mail from Mom. I was so relieved when she said she loved me no matter what I chose to do in life. She said she supported my decision and would always be there for me and my sister. A huge load had been lifted from me. The last hurdle was gone to completing my final stage to becoming Joann. You can read about it in my next chapter.