Life as Joann was moving forward rapidly. With the house to ourselves, I began ordering many things online and having them delivered to the house. In addition, to clothes and lingerie, I ordered a women’s facial electric razor, a laser hair remover, and several kinds of women’s skin cream. I also ordered some different breast forms to try out. Sis insisted on seeing everything that was delivered to the house, which wasn’t a problem, until an order of hormone treatment medication arrived.
“What is this for?” she demanded.
“It will help me look more feminine,” I explained to her. “It will increase my hips and breasts a little. It should also slow the facial hair, too. Why are you so upset? You have been the biggest help in me getting to this point.”
She responded, “I know, but I think it is getting out of hand and I feel responsible.”
“You didn’t force me into anything I didn’t want to do. Why is this such an issue?” I questioned.
Sis answered, “Before it was just dressing up. Now you’re making changes to your body and it seems like I lost my brother Joseph.”
“So you’ve lost a brother and gained a sister. I feel so much better as Joann. I want to become Joann permanently. I’m not the first person to do this and I won’t be the last. Besides, you have given up on men. Do you think that is a mistake?”
Sis responded, “I’m sorry, I’m just worried about you. I’d never forgive myself if I screwed up your life.”
I hugged her as I said, “I’ll be Okay. You’ve helped me in my journey to find Joann and I’ll always be grateful for that. Now Bob is coming over tomorrow night. Can I count on you?”
“Of course.” She replied, “You can always count on me.”
The next morning I got up and started working on my computer early so I could finish early to get ready for Bob. After a few hours, I started to get uncomfortable as it was getting too warm. I realized that all my Joann clothes were for the colder weather. I went into Sis’s room and found a pair of shorts and a half blouse that tie at the bottom in her closet. The shorts were very tight, causing my cheeks to hang out a little. When I tied the bottom of the blouse, it made my tits stick out as it tightened around my mid-drift. When I looked into the mirror in the bathroom, I could hardly contain my excitement. It was going to be hard to concentrate on my work dressed like this. However, it was much cooler and somehow I got through the day.
When I finished my final program for the day, I headed to Sis’s bedroom to get the enema bag from her drawer. I filled it up with warm water and some liquid soap before hanging it on the door. Then I took off my shorts and bikini panties. I took the nozzle and pushed it into my asshole. As I unclipped the valve on the hose, I could feel the warm liquid fill up my bowels until the bag was empty. I pulled the nozzle out, took the bag down, and cleaned everything up. I decided to leave the bag hanging on the door since there was no longer a need to hide it. I sat on the toilet and expelled the warm liquid from my asshole. Afterward, I put my panties and tight short shorts back on since they felt and looked so good.
I made some salad and meatloaf for Bob, Sis, and I for dinner. Before I knew it, the doorbell was ringing. It was Bob. “You look fantastic,” he exclaimed, as he gave me a big hug with both of his hands on my partially exposed ass cheeks. I wrapped my arms around his shoulders as we kissed. Suddenly, I realized, we were on the front doorstep while it was still light outside. I thought to myself; I hope none of the neighbors are watching. As I broke our kiss and pulled Bob inside, he said, “You are so hot, Joann.”
“Thank you,” I replied. “Let’s put your overnight bag in my bedroom. Mandy should be home soon. I made dinner for the three of us.” After dropping Bob’s bag in my bedroom, I poured some wine and we sat in the living room waiting for Sis.
Bob started rubbing my bare leg with his hand. It didn’t take me long before I shifted over and straddled him face to face sitting on his lap. I leaned in and kissed him. He pushed his tongue into my mouth. We were both getting turned on when we heard, “Hey, you two get a room.” It was Michelle and Sis. “I hope you don’t mind. I invited Michelle over. I promise we will stay in my room and leave you two lovers alone tonight,” exclaimed Sis. “Is dinner ready?”
I replied, “Yes, it is. It’s a good thing I made plenty. Let’s eat before it gets cold.” With that, we all went to the kitchen and ate dinner. Afterward, we sat for a while and drank a couple bottles of wine before going to our respective bedrooms.
As Bob took off his clothes, I took off my short shorts and blouse. I took a sheer negligee from my closet and pulled it on over my head. I pushed Bob onto the bed on his back and planted my two lips on his quickly hardening cock, taking most of it in my mouth. Then I started slowly pulling it out while rubbing my tongue on his vein. When it was completely out of my mouth, I started licking around the top of it. I started working my tongue on the little slit at the top of his dick before plunging my lips down his shaft, again. This time he was completely hard so I was able to push the tip of his dick into my throat. He let out a small moan.
I began bobbing on Bob, moving up and down his shaft in earnest. I cupped his balls with my one hand gently squeezing them as I continued to work his cock with my mouth. He placed his hands on my head. Each time I went all the way down on him, he would hold my head, forcing his dick into my throat for a few seconds before letting up. I felt like we were a trained team. We each knew what the other liked.
I was also learning to appreciate wine before sex. We didn’t cum as fast as we did the first few times. I could suck Bob’s dick for over an hour before getting my dessert. After a dozen or so deep throat cycles, I would pull up to lick the pre-cum from the top of his dick. Then I would wrap my lips around the head of his cock and suck it a few minutes before plunging down, again. I was beginning to increase the time I kept his dick in my throat as I got better at controlling my breathing and it became slipperier. I think my throat was getting conditioned to it, as well. I was really enjoying sucking cock.
My favorite part was approaching as I could hear Bob starting to pant. His hands were still on my head, but they were pulling tighter and longer into my throat. As much as I knew he liked to cum in my throat, I wanted to taste and feel it in my mouth. When he shuttered, “Here it comes,” I pulled up until only the tip was in my mouth. His balls were still cupped in my hand so I could feel them tightening up. Then I could feel his vein pulsing against my bottom lip as it pumped his cum into my mouth. The warm fluid started filling my mouth. I could taste the familiar fruit of my labor. Bob was moaning quietly as his cock shot out four or five loads of his warm, soothing cum. I pushed his dick into the back of my mouth and held still as he stopped convulsing. I could feel him begin to relax and soften. I knew he would be sensitive for a few minutes.
Finally, I pulled off, keeping my lips sealed tightly, preventing his cum from escaping my mouth. I sat straight up on my knees. I moved my tongue in my mouth, savoring the feel and taste of Bob’s cum before swallowing his load down my throat. I licked my lips and swallowed again. I must have been smiling since Bob said, “I think you enjoyed that as much as I did.” He was right; I did enjoy it. It made me feel so sexy and feminine. I laid down next to him with my head on his chest to rest awhile. It would be a few hours before he could get his dick hard once more to fuck me.
Around midnight I awoke to Bob’s hand rubbing my right tit. I was wearing my newest pair of breast forms, which was a “B” cup with a larger base and self-adhesive. They were filled with a softer silicone enabling me to feel almost any touch through them to my real skin. I can see now that they were a good investment. I let out a little moan prompting Bob to continue his rubbing as he moved to the other one. With him naked and no blankets on either of us, I could see he was getting hard. I reached down and lightly rubbed his dick with my index finger. It was if my finger was a magnet as I watched his dick rise toward it with each movement around its head. A small drop of pre-cum started to ooze out. I rubbed it around the tip of his dick with my finger causing more to replace it. We were both becoming quite aroused.
I couldn’t hold back any longer. My mouth needed to taste his sweet syrup. I moved my head down and started licking his coated head. His dick grew with every lick until I had to have it in my mouth completely. I pushed my mouth down and forced it into my throat. Holding it in to my limit, I started to gag a little. Backing off, I could feel my slobber on his shaft. I pushed it into my throat a few more times building up the coating of slobber, creating a natural lubrication. As I pulled it out of my mouth, I used my tongue to expel as much of the juice as possible, leaving it dripping down his shaft. He was ready for me.
I climbed on top, straddling him with my knees on both sides of his body. I pulled my panties down in the back and raised my body up over his dick, which was pointing straight up now. Using my right hand, I positioned his shaft so I could feel its head against my waiting hole. Then, I lowered my body on his member, feeling it pushing my sphincter open. I started moving up and down a little working my anal ring open. It had been a while since I was last fucked. After several short pushes and pulls, I began to let the weight of my body sink down, forcing his shaft into my ass. I raised my hands up into my hair as I felt my ass being filled. Bob put his hands around my waist as I began smiling in ecstasy.
When I was completely down with my weight fully on Bob, I began to move my body back and forth, feeling his dick moving around in my ass. Then, I leaned back a little pushing it as far up my ass as possible. My knees were slightly off the bed as I shifted all my weight to my ass as I was literally sitting on his dick. Bob started rocking his pelvis while pulling my waist toward him in a perfect rhythm. I moved forward as he pulled until my knees touched the bed, followed by me leaning back, as he pushed me back down, again. Now I understood the term “riding him”. We went on like that for at least twenty minutes. The heat was rising in my ass from the continued friction. His dick felt like a hot potato inside me. I lowered my hands from my hair and placed them on top of Bob’s to set the pace. I prompted him to rock faster for a few minutes, then a slow, deliberate motion, alternating back and forth.
As I felt myself getting close to an orgasm, I took Bob’s hands in mine and used them to balance me as I increased to a maddening pace. I could feel him starting to buck. I leaned down on him, chest to chest, which pulled his dick almost out of me when he declared he was cumming. I rammed my little dick into his abdomen, setting it off and pulling his dick from my ass at the same time. I could feel him shoot his last stream of cum between my cheeks as I shot my load between our tightly nestled bodies. I collapsed on top of him as he wrapped his arms around me. We stayed like that for a while as we started to cool down a little. When I finally had the energy to move, I got up on my hands and knees moving down to lick my cum that soaked through my panties off his pelvis. I pulled up my panties as I lay on my side, still feeling his cum between my cheeks. Bob got up and went to the bathroom. When he came back, we both fell asleep until morning.
When Bob woke up, he whispered to me, “I have to go to work in a few hours. Can I use your shower?”
I responded, “Of course you can. Your bag is on my bureau. It looks like Mandy and Michelle kept their promise. We didn’t get any visits through the night.” After Bob went into the bathroom, I got up. My ass was still sticky with his cum. I didn’t want to give up that feeling, so I put on a silk robe and went into the kitchen to make some breakfast. If this is supposed to be “the walk of shame,” then shame on me. I love the feeling of cum squishing between my cheeks and the wetness in my asshole. I was actually wiggling my ass to feel it better.
Suddenly a voice rang out, “Interesting moves.” It was Michelle. She walked over and rubbed my ass with her hand. “Feeling good, are we? Anyone ever tell you that you have a nice ass?” She gave me a little kiss on the lips.
I replied, “Yes, to both questions. I’m feeling great and I have been told I have a nice ass. I made some breakfast. Are you and Sis going to eat?”
“Sure. Where’s Bob?” Before I could answer her, Bob and Sis came into the kitchen. We all sat down and ate breakfast before Bob had to leave for work. Then, I walked him to the door. This time I gave him a big kiss inside before opening the door, in case there were any neighbors up and about. As I walked back to the kitchen, I was swaying my hips to move my ass cheeks thinking about the cum there from last night. Michelle and Sis were all smiles as they watched me.
“I’ve got to get some of whatever it is you had last night,” commented Michelle.
I just smiled and said, “I’m going to take a shower and get dressed.”
After taking a pee and cleaning my face, Michelle walked into the bathroom. She pulled down my panties and put my little dick in her mouth. It started to get hard as she licked it. She stood up, gave me a little kiss on the lips, turned her back to me, and rubbed her ass against my dick. Then she pulled her nightshirt up over her head and dropped it on the floor. She was completely naked now as she continued to rub her ass against my dick. Instinctively, I put my hands on her hips. She responded by pushing her ass even tighter against my crotch as she bent over the sink. “Please, fuck me in the ass,” she said. “I’ve always wanted to feel a real dick cum in my ass and I feel safe with you. Please, Jo.”
How could I say ‘no’ when I was enjoying it myself a few hours ago? I know how bad I needed it from Bob last night. I backed up a little and rubbed her cheeks. She had a beautiful ass. I pushed her cheeks apart revealing her cute little rosebud. I put the tip of my dick against it and started to push as I held her by her hips. While there was a little resistance, I was able to push into her ass quite easily. She gave a little moan as she pushed her ass back into my crotch, once again. I pulled out a little, then, pushed back in. Michelle started moving back and forth impatiently. I knew what she wanted. I started moving my hips back and forth with hard forward thrusts pushing into her ass. She responded, “Oh yes, Jo. You know what I want.” I could feel the heat building up in her ass. We were moving together in opposite directions. As I pulled back, she moved forward. When I pushed forward, she pushed back.