Stage Six Of My Journey To Becoming Joann free porn video

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As I awoke on Christmas morning I found three presents on the end of my bed. There were handwritten tags on each with the message: open in private. There was no doubt in my mind as I opened them that they were from Sis. The first was a body shirt that pulled down and snapped in the crotch. It was white with a v-neck trimmed with lace around the neck and sleeves. The second was a set of breast forms slightly bigger than my regular ones with conspicuous and pert nipples. The third was a very sheer, yet plain bra that hooked in the front. I really wanted to try them on, but it was already 8:30 am and Mom said Dave would be here at 9:00.

 

I put on my sweat pants and a tee-shirt before using the bathroom. Sis’s door was open a little, so I peeked in to see if she was awake yet. “Merry Christmas, Jo,” she said as she saw me.

 

I walked in, gave her a hug, and said, “Merry Christmas to you, too. Thank you for the gifts. I can’t wait to try them on.”

 

We both went into the living room and sat on the floor next to the Christmas tree waiting for Mom. Hearing us talking, Mom yelled down that we had to wait for Dave before opening our gifts. A few minutes later, he was knocking on the door. Sis ran to the door to let him in. She was always excited to open presents on Christmas morning and this was no exception. I got mostly clothes (men’s) from Mom. Sis got some jewelry and clothes. We got Mom a ring with both of our birthstones on it. Dave surprised Mom with plane tickets and New Years Eve reservations in his home town. Sis whispered to me, “I think they’re getting serious.”

 

The four of us spent the day together including Christmas dinner. Dave seemed quite interested in me and Sis’s personal lives. This would make more sense in a few weeks. At the end of the night, Dave left for his hotel. Mom told him she would see him tomorrow. The three of us sat up and watched Christmas movies until it was time to go to bed. I would have to wait to try on the new clothes Sis bought me.

 

The next day at lunch, Mom asked if we would mind if she spent a few days with Dave. We both assured her it was okay and how happy we were to see her finally with someone. We told her we would work on the Christmas leftovers for dinners while she was with Dave.

 

As soon as she left, I went straight to my bedroom to try on Sis’s gifts. She followed me saying, “I want to make sure you like everything.” I stripped down and put on a pair of boy short style panties. Sis came in from her bedroom with a can of adhesive. “Hold your arms up,” she said as she carefully sprayed my chest. Then she took out the breast forms and sprayed them. “I really think you’re going to like these,” she said.

 

After a few minutes, she placed the breast forms on my chest and adjusted them. I pulled the bra on from behind me and hooked it in the front. “Why don’t they make all bras hook in the front?” I questioned, “It seems a lot easier.”

 

“I don’t know,” Sis replied. “They’re probably designed by men.”

 

I pulled the body shirt over my head, then reached down and snapped it. Sis handed me a pair of tight stretch jeans. After putting them on I went to the full length mirror in the bathroom. I loved the way I looked and felt. It looked like I had real tits. The nipples were pushing through the fabric. The bra was hardly detectable, almost making it look like I was braless. The shirt was pulling between my ass cheeks and against my tucked in dick and balls. I gave Sis a big hug as I said, “Thank you so much. You really know what I like. I want to leave this on for a while.”

 

“Maybe you can wear it on New Year’s Eve,” Sis suggested. “Did you talk to Bob yet?”

 

“No,” I answered, “I’ll call him tonight.” I couldn’t stop rubbing my hands on my breast and my hips. I felt so sexy. Sis smiled as she could clearly see how much I was enjoying the new ensemble. “Damn, you know how to make me feel good,” I exclaimed.

 

“So do you. Now, maybe you can help me a little with one of your gifts from a few weeks ago,” she said as she motioned me to follow her. As we walked into her bedroom, she pulled her blouse off over her head dropping it on the floor. Then she pushed her sweat pants down and stepped out of them. She asked me to unhook her bra as she let it fall onto the floor before pulling on a silk nightie. Opening the drawer in her night table, she pulled out the bag from Fantasies where we stopped a few weeks ago and handed it to me saying, “I’ve been waiting to try these out and I need some relief until I see Michelle, again.”

 

With that, she pulled her panties down, stepped out of them, and climbed into her bed laying face down with her legs spread open. There were two packages in the bag. The first was a large vibrating dildo with raised rings around it. The second was the dildo for anal use that she said she would “try on her back door” when we were at Fantasies. “There’s batteries and lotion in the night table. Use the lotion on the anal one,” she instructed. I reached over, grabbed the batteries, and put them in the vibrator.

 

I put the head of the dildo up to her pussy lips, moving it up and down her slit trying to find her little entrance. Finally, I had to rub my finger along her slit until it slipped into her tiny hole. Then I lined up the dildo on top of my finger and slowly started pushing it in as I removed my finger. Sis let out a little groan as I could feel the dildo start to penetrate her. I was surprised at how much resistance there was pushing it into her. She began to gasp as I continued to push. “Are you alright?” I asked as she groaned louder.

 

“I’ll be okay,” she answered. “Just go slow, this is the biggest thing I’ve ever had in me.” I watched as her pussy lips opened up as each raised ring pushed into her and then looked like they were swallowing it as they closed in on the smaller diameter between them. It seemed like forever as I forced what must have been nine inches long into her. Her face was buried in her pillow muffling her groans while her hands were clenching the head of her bed. Finally, I had the entire dildo in her pussy with only the rotating switch left exposed.

 

I opened the other package and removed the anal dildo. Then I rubbed the lube, which turned out to be warming lotion, on it before lining it up with her back door. It was smaller in diameter, shorter, and more streamlined. Here I was an expert at insertion. I pushed it into her puckered hole a little bit, then withdrew it slightly. Then, once again, I pushed it in a little and started working it in and out. As she seemed to relax, I pushed further until it was in a few inches. When I felt she was ready, I slowly pushed it steadily up her ass as I could hear her groans turn to moans. Finally, it too was all the way inside her except the small ring handle.

 

Next, I turned the knob on the vibrator a little. I could feel it start to vibrate. Sis let out a long subdued moan. Then I turned it up all the way. She raised herself a little on her elbows and began to cry, “Holy fucking shit.” With that, I began to alternately push and pull the two shafts a little in her two holes. I couldn’t tell if it was her body or the dildo vibrating. She started to tremor as she pushed her head back. Then she just started repeating, “Yes, yes, yes,” over and over, again. After what I assume were multiple orgasms, she closed her legs tightly together clenching her ass cheeks for the grand finale. “I can’t believe this. I should have tried this years ago. You can’t believe how hot I am inside right now.”

 

Actually, I could believe much of how she was feeling. I was also quite wet myself. My little dick must have leaked out precum for a while in spite of being restrained by the body suit and tight jeans.

 

Sis kept her legs tightly closed as she moaned off and on for ten or fifteen minutes. Finally, she simply collapsed, spreading her legs slightly. I started pulling the dildo out of her ass which caused her to start moaning, again. When I pulled the last of it out I could see her hole open like the dildo was still in it. Suddenly, it just closed up. While I remember this on some of the porn videos, I never saw it in person. It was awesome.

 

I took the dildo to the bathroom and washed it in the sink. When I returned, Sis was laying on her back licking the vibrator like a lollipop. “I love the taste of pussy,” she declared. “Thank you for helping me out. That was awesome. I really needed that.” She got up and went to the living room sofa and turned on the television.

 

Since it was still early, I went to my bedroom and called Bob. I asked if we had plans for New Year’s Eve. When he said “No”, I asked if he wanted to go to a party with Michelle and Amanda. He replied, “Okay.” We agreed to meet at his apartment around six on New Year’s Eve. After we finished talking I went out to the living room to tell Sis. She was sprawled out on the couch asleep in just her silk nightie with her legs partly open. She was wet all over inside her thighs, on her ass cheeks, and on her pussy lips. I didn’t want to wake her, so I placed a throw blanket on her to keep her warm. Then, I went back to my bedroom took off my jeans and body shirt. Since the breast forms were only on for a few hours and felt so good, I decided to leave them and the bra on. I went to Sis’s room, grabbed a long negligee, and put it on. I went back to my bedroom where I eventually fell asleep watching porn on my laptop.

 

The next morning I awoke to the sound of the shower. I walked into the bathroom and sat to pee. Sis called, “Is that you, Jo?”

 

I replied, “Yes, I had to pee.” Then I went on, “I talked to Bob last night and he’s good with a double date to the party. I was going to tell you last night, but I didn’t want to wake you.”

 

“Sorry, but you made me feel so good it exhausted me. Thanks for covering me up. I hope I wasn’t in an embarrassing position.”

“No, you should never be embarrassed with that body. Let’s talk about the party when you get dressed.” We still had another day before Mom came home, then she would be leaving the following day for a week. With no work, school, or soccer, I could spend most of the week dressed as I pleased. I went to Sis’s room to pick out a lighter coverage bra, a blouse with a plunging neck line, and a tight pair of stretch jeans. I was changed before Sis finished her shower.

 

“Don’t we look sexy today?” Sis exclaimed as she walked into her bedroom with a towel around her. “I guess you’re going to take advantage of the alone time.” She picked out some clothes for herself, dropped her towel, and dressed while she continued to speak. “Why don’t you make some breakfast while I start the laundry. Then we can sit, talk, and maybe watch some television.” We spent the day planning for New Years.

 

The remainder of the week was great. I was able to spend a lot of it dressed in my limited female wardrobe and Sis’s extensive collection. Sis kept picking out clothes for me through the week. The timing was also perfect since Mom would be away the two days before the party.

 

I started New Year’s Eve by giving myself an enema before taking a bath in Mom’s large tub where it was easier to shave my legs, arms, and chest. Sis came in and offered to shave the places I couldn’t reach. She also poured some bath lotion in the tub. I love the smell of women’s fragrance products. When I came out of Mom’s room Sis directed me to our bathroom where she washed my hair in the sink. She said she would style my hair later after she took a bath. I put on a night shirt and watched television while waiting on her to keep my mind occupied. I was getting excited about being with Bob.

 

When she was done her bath, she called me into her bedroom. I sat down at her vanity where she styled my hair a little differently than in the past. She explained her every move to me so I could do it in the future. Then, she polished my nails and I polished hers. We both packed our bags the night before and had our outfits for the night already laid out. I pulled off my night shirt so Sis could attach my new breast forms. After the adhesive was set, I put on a thong, the new bra, and blouse. As I pulled on my jeans, I noticed Sis had replaced them with a pair that zipped up in the back. She said they would make my butt look better. She was right.

 

We both put on our make-up at the same time. I watched carefully so I could do it better by myself from now on. Sis handed me a pair of platform shoes and told me I should walk around the house a while before we left to get used to them. I took her advice. While I could easily walk in them, I didn’t look too feminine at first. I had to adjust my style of walk to look convincing. With the exception of my voice, I felt quite confident about passing for a full fledged woman. I would still have to resort to an almost whisper when talking.

 

Sis gave me a waist high coat to wear. We both grabbed our bags and headed for her car. She said we would pick-up Michelle first, then Bob. She called Michelle a few minutes before we arrived there and she came out as we pulled into the driveway. I got out of the car so Michelle could sit in the front seat with Sis. Michelle gave me a hug and a little kiss on the lips before saying, “Hi, Joann, it’s good to see you, again.” Then she got into the front seat on her knees, put her arms around Sis, and pulled her tight as she kissed her for a long minute. I pushed her door closed and got into the back seat. “Sorry, I haven’t seen Mandy in over a week,” Michelle exclaimed after finishing her extended kiss.

 

When we got to Bob’s, I had to walk up to his door since it is hidden from the parking lot. We returned to the car and climbed into the back seat. Bob immediately said, “Hello Michelle and Amanda. It is good to see you both, again.”

 

The party was at a frat house on the college campus only five minutes from Bobs. We parked in the street less than a block away. There must have been several parties as the street was full of revelers everywhere. As we walked into the house, I realized I was a stranger there. Amanda, Bob, and Michelle knew many of the people. However, this worked in my favor and actually made me feel more comfortable. We all sat down spending the next five hours drinking toward the target time of Midnight. Michelle and Mandy were quite open with their affection for each other. No one even seemed to take much notice. Bob was also quite forward through the night rubbing my leg, hugging, and kissing. Of course, we looked like an ordinary couple.

 

A few minutes before midnight, most of the party headed into the street to ring in the New Year. Fireworks erupted from a distance as everyone cheered. Bob wrapped his arms around me and we both kissed for several minutes. “Happy New Year, Joann! You’re the best, I’m so glad I met you.” I pulled his hands down to my ass before reaching around his neck for another kiss. As we finished our second kiss, Mandy and Michelle were putting their arms around the two of us. We exchanged kisses and Happy New Year's wishes before returning inside for another drink.

 

Before I knew it, I realized we were all getting quite drunk. I asked Sis if she was okay to drive. She said she was if we left before she had any more to drink. We headed for the car, then drove to Bob’s. He suggested we all stay at his apartment for a while to sober up a little. He brought out some snacks to munch on as we sat around the table. Bob suddenly said, “Mandy, you and Joann are amazing.” Sis looked at him a little puzzled.

 

I whispered in her ear, “Don’t you remember when you told Bob and Jim we were both men dressed as women at Michelle’s party a few months ago?”

 

Sis started laughing as she said to Bob, “I’m sorry, I lied to you.” Now Bob had a puzzled look on his face. She unbuttoned and unzipped her jeans, then took Bob’s right hand and pushed it down her panties. “Surprise,” she said.

 

Bob responded by looking at Michelle and questioning, “And you?” I wasn’t sure if Michelle was mad or hurt, but she was certainly confused, so I let her in on the joke. To my surprise, she lifted her skirt, which immediately revealed her gender since she wasn’t wearing any panties. It also made me confused now. Did Michelle realize I was not a real woman? Did Sis tell Michelle I was her brother?

 

Sis jumped in, “Michelle and I are lesbians. Joann is my sister, I mean brother. Does that clear everything up for everyone? Michelle, I’m sorry I didn’t tell you.” Then she looked at me and started to breakdown crying, “Jo, I didn’t mean to hurt you, I ruined everything, didn’t I.”

 

Bob rescued the day, “Joann and I are going to my room. Mandy and Michelle, you can use Jim’s bed if you would like, if not lock the door on your way out.” He took my hand and led me to the bedroom. I went into the bathroom and changed into a mid-length sheer teddy with a matching bra and panty.

 

When I returned to the bedroom I climbed into bed and whispered into Bob’s ear, “You’re the best, I can’t wait to feel you inside me.” I laid on my stomach and spread my legs a little. Bob rolled over on top of me gently pulling my panties down below my ass. Then, he rubbed his dick between my cheeks as he started to harden. I felt the tip of his dick against my hole and pushed my ass up a little to make it more accessible. He started to push until he began to penetrate me. Then he pulled back and pushed again. I was dry so it took some poking to open up my asshole. I thought about last week with the anal dildo and Sis. Her hole opened up after a little working it. I usually start off with some oral play to get Bob’s dick a little slippery. However, I wasn’t about to put his dick in my mouth after it was in my ass. I told Bob to get some lube from my night bag. He got out of the bed and got the lube. As he was putting it on his dick he said it was getting hot. Sis must have put her warming lotion in my bag.

 

Bob put his dick up to my hole, again, and started to push. The lotion made a big difference. I could feel the head of his dick slide through my sphincter and up my ass. The heat was amazing. It felt like his dick belonged in my ass. The lotion didn’t feel wet like the lube. It was more of a syrup feeling that allowed his dick to glide in my ass while still creating friction and so much heat. My ass was on fire. I could feel him bottom out as his balls were compressed against mine. He started withdrawing giving me an empty feeling that wanted him to push back in. As he was almost out he started pushing in. My ass welcomed him back impatiently. Each repeated stroke brought more heat and fulfilment. The alcohol must have had an effect on us both. We went on like this for a long time.

 

Finally, I closed my legs tight against each other forcing Bob to move his legs outside of mine. He was sitting up on his knees with his weight on my ass cheeks. This forced my cheeks together tightening my grip even more on his cock. But, it also gave him better leverage to push into my tightened ass with his hips. I could even feel the heat on my ass cheeks now. His hands were on my shoulder blades to keep him steady. Now his forward thrusts were stronger and I could feel the entire length of his shaft rubbing my cheeks, anal ring, and insides. He was panting and I was moaning loudly. While I’m sure Mandy and Michelle had to hear us, it didn’t matter as we were literally caught up in the heat of the moment. I couldn’t believe that each time we fucked, it was better than the last.

 

Suddenly, I came like never before. My panties were soaked and my little dick was sliding in a pool of come. I knew Bob was close. He was starting to moan loudly and began to just keep pushing, trying to go as deep into my ass as possible. Then with a last push, he yelled out, “Ohhhhh fuck.” I could feel his balls pulse between my legs, his thighs tighten, and his cock pumping his cum into my ass. I wish I could feel his actual cum deep inside me, but I don’t think that is possible. He stopped and held still for a few minutes, letting his dick spasm two or three times.

 

I asked him, “Leave it in as long as you can. I feel so empty when you pull it out.” He moved his knees back and laid forward on my back with some of his weight on his elbows while moving his hands under my tits. I love this position. I squeezed my ass cheeks with my muscles several times to both our delight. He kissed me on the back of my neck. I responded with, “You’re the best and you were my hero tonight. I hope things went as well with Mandy and Michelle. Do you think they heard us?”

 

Bob responded, “Unless they were deaf, I’m sure they did.”

 

Bob’s dick was quickly shrinking in my ass. I knew it would come out shortly. While I love his bare dick in my ass, I miss licking the cum off it after sex when he wore a condom. Oh well, can’t have everything. When it finally shriveled out it left a small trail of his cum dripping from my ass. Bob got up and went to the bathroom to wash off and pee. When he returned we laid side by side on our backs relaxing.

 

A few minutes later, Michelle and Sis came into the bedroom. Sis walked along Bob’s side, leaned down, and gave him a little kiss as she said, “Thank you so much for taking care of my sister and not letting me screw up the night.”

 

As she stood up, Bob put his arm around her waist and hugged her saying, “You’re welcome, it was my pleasure.” Sis put her hands on his head pulling his face against her pelvis as she looked at me. I smiled, which she must have taken as an invitation. She climbed up on the bed, lifted her night shirt, and straddled Bob pushing her pussy in his face. He had little choice but to oblige her,

 

Michelle took that as a cue and climbed on top of me in a “69” position. She pulled down the front of my panties and started licking the cum on my cock as she pushed her pussy into my face. Her pussy tasted sweeter than Sis’s. While my cock started to harden, I was still spent and a little drunk. This did not deter her at all. This was the first time I ever had my dick sucked and Michelle was going to make it memorable. In the meantime, I was licking up and down her slit. When I reached the top I messaged her clit with my tongue. When I reached the bottom I pushed my tongue into her hole. She had my little cock and balls completely in her mouth as her tongue messaged them. Then she would pull back letting my balls come out and suck hard on just my cock.

I could hear Sis moaning out an orgasm. She climbed off and started to jerk Bob off. Then she pulled my head from Michelle’s crotch onto Bob’s cock while Michelle continued with my first class blow job. Sis moved over and took my place on Michelle’s pussy. With all of us inebriated, this went on for at least half an hour. Finally, Bob put his hands on my head as he usually does when he’s getting close. As he pushed down, I took his dick into my throat. When he started to groan, I pulled up so I could feel and taste his cum. He didn’t disappoint me. He must have shot four or five times into my mouth. Normally, I would pause, but my body was responding to Michelle’s motion. I had to pull my mouth off of his still stiff dick and swallow my mouthful of cum as I sat up. This forced my little dick further into Michelle’s mouth. She started sucking harder. I leaned back on my knees placing myself just above her head. She tilted her head back and I leaned forward on my hands. I started fucking her face as I looked down on Sis’s face in Michelle’s pussy.

 

Sis must have hit the spot on Michelle as she started bucking her pelvis and moaning on my dick. For the first time in my life I came in someone’s mouth. Michelle came at the same time and she just kept sucking as part of her orgasm. Sis sat up and pushed my head down on Michelle’s pussy. Michelle and I squeezed each other tight as our orgasms slowly subsided. Sis rolled over on the other side of Bob sandwiching him between her and Michelle and I. When Michelle relaxed her grip on me, I moved my head up to the same end as everyone else. Sis was spooning Bob, who was spooning me, as I was spooning Michelle. Bob and Michelle were naked. Bob’s left hand was on my left tit and my left hand was on Michelle’s left tit. We all fell asleep in that position.

 

Michelle was the first to wake in the morning. She rolled out of the bed and stood up. She was beautiful standing there naked. She had blond hair, pert tits without a bra, smooth light skin, and a perfectly proportioned ass. I so wish that was my body. Sis got up and asked Bob if she and Michelle could use the shower. A few minutes later we could hear them giggling and laughing in the shower. Bob looked at me and said, “That was an interesting night.”

 

I responded, “Does this change anything between us?”

 

He answered, “Of course not.” With that I rolled on top of him rubbing my ass against his dick to get him hard. “What about Mandy and Michelle?” he asked.

 

“What about them?” I replied. “After last night there is little to hide. Besides, I think they’re already occupied and I need you inside me, again.” I reached over to the night table and grabbed the warming lotion. I rubbed some on Bob’s dick helping him harden faster. Then I pushed myself up, pulled down my panties, and lined up his dick with my hungry ass. As soon as I felt it against my waiting hole I descended down faster than ever before. I never wanted it so badly before. I bottomed out in seconds. After pushing my pelvis back and forth several times, I pulled up until the tip of his dick was almost out. Then I dropped my entire weight down swallowing his dick completely up my ass. I could feel the warming lotion heating up my insides. I started moving my body up and down on his shaft like it was going to be my last fuck.

 

I never felt so horny. I couldn’t get enough. Bob was already panting loudly. As I could hear him begin to let out a moan I raised up until he was almost out of me so I could feel him cum in my ass. Suddenly, I realized Michelle was standing next to me. She started jerking me off through my panties. I came in less than a minute while Bob’s dick was still just inside my asshole. When I pulled off of him, I could feel his cum between my cheeks. Michelle said, “Awesome, you’re a mess. I hope you didn’t mind me helping out. I was waiting for Mandy to finish in the bathroom.” She pulled up my panties in the back and kissed me on the cheek. Bob and I just looked at each other.

 

When Sis was done in the bathroom, it was my turn to get cleaned up and dressed for the trip home. I put my body suit and stretch jeans back on since I loved the way they made me feel. Mom would not be home for a few days so I could wear everything home. Bob gave me a long “I want to see you again” kiss before we left. We dropped off Michelle at her house and went home. We both had to go back to work the next day.

 

I had a lot on my mind the next few days as I digested all that happened over the New Year holiday. It was only the start of a defining year in my journey to become Joann. Mom brought the next major event. She arrived home from her five days with Dave announcing she had to talk with Mandy and I. After dinner that night, she told us that Dave asked her to come live with him. They were both cautious about their relationship but agreed they wanted it to continue. Mom said she understood we had school and work here. She said the house was paid off from the divorce settlement and proposed Mandy and I could pay just enough rent to pay the expenses. This way she could keep the house and we could remain here. The rent was dirt cheap split between the two of us.

 

We expressed our happiness to Mom and agreed to her suggestion. We also agreed to keep her bedroom always available for her to visit. The hotel where she bartended set up a transfer to Dave’s town. She was excited since she would be the Bar Manager and it would be day work. Of course, she would also be with Dave. Mom deserved this break. It also provided me with more time and freedom to be Joann.

 

Mom moved out the last Friday of January. That Saturday morning I emptied most of my drawers and started filling them with my clothes for Joann. I kept two drawers for Joseph’s clothes on the bottom of one bureau. Sis came in and asked me what I was doing. After explaining it to her she asked, “Does this mean you don’t want to share clothes anymore?”

 

I replied, “Of course, we can still share, we just need more room and I’d like to keep some of my favorites in here now that I can dress more often.” I spent the entire weekend dressed as Joann.

 

The next event came a few weeks later at work. The boss called me in his office. He told me we just got several large contracts. This would require six more CNC machines. The programming load would jump up and we were running out of office space. He wanted to know if I’d be willing to work from home. The company would pay for the computer, programs, and all internet services. The drawings would be e-mailed to my house. When I finished a machine program I would simply save it on the company file where it While would be accessed by the shop and downloaded into the milling machines. I would only have to come in if there was a discrepancy in the machining. I would be promoted to “Head Programmer” along with a substantial raise. How could I say no?

 

Within two weeks the company set-up a computer, phone, large printer, and a big screen monitor in the den in our house. I got up Monday morning for my first work at home day when I realized I could stay Joann all week except to attend my final semester on Tuesday and Thursday nights at the Community College. I started wearing stretch pants and pullover blouses with a comfortable bra and bikini or boy cut panties during the day for working on the computer. Since Sis was going to school Tuesday, Wednesday, and Thursday nights, I would often make dinner for both of us. I also started spending more time on the internet in the evenings.

 

Sis started having Michelle spend the weekends at the house. The two of them would often walk around the house in nothing but their bras and panties. I think Michelle was more bi-sexual than Lesbian. She started pulling me into their activities. On Saturday night we all sat and watched some porn on the living room couch when Michelle asked if I could use Sis’s toys on her. Apparently, Sis told her about the time between Christmas and New Year’s.

 

We went into Sis’s bedroom. Sis and Michelle both stripped naked as Sis laid on her back. Michelle climbed on Sis in a six-nine position with her ass facing the end of the bed. Sis said, “Fill her up,” with a laugh as the two started licking each other’s pussies. I opened the night table drawer and pulled out several dildos, vibrators, and warming lotion. I selected the large vibrator that I used on Sis two months ago. Then I rubbed my finger up and down Michelle’s slit until it pushed into her warm hole. I put the tip of the vibrator over my finger pushing it in as I pulled out my finger. I started pushing it into Michelle’s pussy. Her lips pushed open and closed as each ring of the vibrator disappeared into her as she started to moan in sync with the rings.

 

Once the vibrator was completely buried, I lubed up the anal dildo while Sis was licking around the exposed end of the vibrator. I then lined it up with Michelle’s little ass hole and gave it a slight push. She gave out a loud gasp as she cried, “Oh, I love this like you do, Joann.” With that assurance, I proceeded to slowly push the dildo deep into her ass. When it was as deep as it could go, without losing it in her ass, I turned the knob on the vibrator in her pussy. Michelle started moaning, “Ohhhhh, this is the best.”

 

Sis stopped licking just long enough to utter out, “Do you have something for me?” I moved to the other end of the bed and grabbed a vibrator with raised nubs all over it. Since it was not as large as the ribbed vibrator in Michelle’s cunt, I easily inserted it into Sis’s pussy, before turning it on vibrate. Michelle put her mouth over the end of the vibrator. Both of them were now moaning with their mouths full as their heads and bodies were constantly bobbing. I was sitting up on my knees between Sis’s legs watching Michelle work the dildo in Sis’s pussy with her mouth.

 

Michelle reached up under my night shirt with her one hand and started jerking me off through my panties. Her moan changed tones as she began to have an orgasm. She increased her pace and grip on my dick. I came like a race horse. She continued to rub my dick spreading my cum all over her hand as she had multiple orgasms. Sis was moaning loudly also now and was having a couple orgasms herself. Finally, they both collapsed. Michelle raised her head up, pulled me closer, and licked the cum from my panties. Then she pulled the top of my panties down a little and put the end of my now soft dick into her mouth licking it clean.

 

I moved back to the other end of the bed and pulled the dildo out of Michelle’s ass and took it to the bathroom to clean it. When I returned Michelle and Sis were sitting up on the bed next to each other with the vibrators in their mouths giggling like little girls.

While Michelle made me feel good and it was exciting to watch both of them, it was apparent to me what I really wanted. I needed a man. Since Sis and I had the house to ourselves, it was time to invite Bob over. This year was shaping up to become the pivotal year in becoming Joann. Up until now, I was Joann one or two days a month. Now, I could be Joann five out of seven days. I decided to call Bob on Sunday morning. He said he could come over Friday night. I can’t wait until then.

 

 

 

Same as Stage six of my journey to becoming Joann Videos

2 years ago
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Stage eight of my journey to becoming Joann

After returning home from dropping Mom and Dave off at the airport, I immediately jumped in the bathtub and took a long bubble bath. While I was in the bathtub, I shaved the stubble that was starting to form from days of neglect. When I finished my bath, I rubbed most of my body with a good lotion to restore its smoothness, followed by a badly needed pair of sexy red lace bikini panties with a matching bra. I pushed a pair of “B” cup self-adhesive breast forms into the bra. They are quick and...

Crossdressing
4 years ago
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Stage five of my journey to becoming Joann

As I opened my eyes it was quite light. I sensed it was late morning. Bob was still spooning me, but his dick was soft and must have pulled out of my ass sometime through the night. I quietly rolled out of the bed and walked to the bathroom. Before sitting to pee, I reached around and pulled another condom from my ass. I guess when he lets his dick soften inside me it shrinks from the condom leaving it in my tight ass. I’m finding it to be an after sex turn-on. I sat on the toilet and peed....

Crossdressing
3 years ago
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Stage Three Of My Journey To Becoming Joann

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...

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Stage Two Of My Journey To Becoming Joann

Life was becoming a little confusing. I was out of high school and attending the local community college part-time at night while I worked at the machine shop during the day. I played soccer on the college team in the inter-county conference. Mom helped me buy a nice used car. Still, I wore panties, a bra, and nightshirt to bed every night. Sis was working part-time at a hairdresser while taking cosmetology courses in the evening. We still sat together in our panties and nightshirts...

Crossdressing
3 years ago
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Stage Four Of My Journey To Becoming Joann

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...

Incest
3 years ago
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Stage One Of My Journey To Becoming Joann

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Older Women Joann

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Being Joann

I sat in front of my computer and started surfing transgendered sites when I came across an article on psychiatrists specializing in cross-dressers, transvestites, and transsexuals. Some of their treatments included a psychological evaluation, hormone therapy, group sessions, and preoperative assistance. The mail order hormones I was taking were having some positive effects, but I read there were better and safer hormone medicines available by prescription. also really wanted to get some breast...

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1 year ago
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Jane is taught about sex from her older sister Joann

After our sex lesson that night, two weeks passed before anything happened. Dad got the flue and the mom got it and so every day when my sister and I came home, there was a parent there. We talked and Joann gave me some ideas on how to get Danny to eat my pussy and still not make me a slut at school. She showed me how to masturbate so I would get the most out of it! She told me how she really wanted to masturbate together and taste my pussy and how she wanted me to lick hers. But, with the...

Incest
1 year ago
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Jennifers Journey Becoming the Perfect Wife Part 1

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2 years ago
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Seasons Beatings From Joanne

Katherine Wilson sat at the kitchen table staring at the clock on the wall. She was angry. Fuming in fact. She had struggled to cook the family a roast dinner with her broken right wrist and here she was, waiting for them to return from the football match. Her husband and son were late. Not unusual, but this time they were spectacularly late. Nearly two hours after they had promised to be home, they had still not arrived. She had called and texted them but had received no reply. She had sworn...

Spanking
3 years ago
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Seasons Beatings From Joanne

Katherine Wilson sat at the kitchen table staring at the clock on the wall. She was angry. Fuming in fact. She had struggled to cook the family a roast dinner with her broken right wrist and here she was, waiting for them to return from the football match. Her husband and son were late. Not unusual, but this time they were spectacularly late. Nearly two hours after they had promised to be home, they had still not arrived. She had called and texted them but had received no reply. She had sworn...

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1 year ago
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Joanne

In The Park – Part oneThis is a continuation of the exhibitionist adventures of Andrea and Mike as depicted in the 'Carried Away' story which appeared earlier this year. The story is kind of long and it is divided into two parts. I would appreciate all comments.I hope you enjoy the story.Andrea had become increasingly curious about exhibitionism since her experience at the beach with her husband. She surfed a lot of web sites and eventually came upon some personal ads. She ended up e-mailing...

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Jennifers Journey Becoming the Perfect Housewife Part 4

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Jennifers Journey Becoming the Perfect Housewife Part 2

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1 year ago
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Kelly is my wife’s best friend, but could I get her into bed?My wife, Joanne, and her best friend, Kelly, met in college and have remained friends for five years. Joanne is a sultry brunette, but Kelly is a gorgeous blue-eyed blonde that I wanted terribly from the moment we met.Kelly and her husband, Jack, came down from New York to Florida for a visit this summer and I could hardly keep my eyes off of Kelly. Her long blonde hair and blue eyes were driving me crazy! But we’d just met, so I knew...

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Life was tough at the moment for an 18 year old. Jobs were hard to find and keep, and I was desperate to earn an income and not be reliant on handouts from the government. Then I got a job, not the flashest of ones, it was selling and installing water efficient showerheads. I had to go door to door and try to interest the householder. They were reasonably priced and I had some success. It was a Friday morning and I was about to leave home to scope out a new suburb in my city when my mum...

3 years ago
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JoAnne had the fresh scrubbed complexion of a teenager. Her soft brown hair looked equally good in a pageboy, a ponytail or pigtails. She had the nice tight body of a high school cheerleader and at twenty-two she looked like the All-American girl next door. She did not resemble in any way, shape, manner, or form what she really was - an absolute slut. She had been one since she was eighteen when, high on beer following a football game, she had allowed five guys to take her cherry. Everyone in...

3 years ago
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Jennifers Journey Becoming the Perfect Housewife Part 17

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Jennifers Journey Becoming the Perfect Housewife Part 15

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Jennifers Journey Becoming the Perfect Housewife Part 3

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Jennifers Journey Becoming the Perfect Housewife Part 13

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Jennifers Journey Becoming the Perfect Housewife Part 7

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2 years ago
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When I first met Joanne

I was home in Melbourne looking over Craigslist seeing what was on for offer. I enjoy pussy and cock so was looking at all the sections and then came across t4m.So had a look and found a advert for a mid 30's tranny wanting a guy to come over for some fun.Now I've enjoyed watching shemale porn and so sent a message. It wasn't too long that I got a response from Joanne.Anyway getting to the chase. I rang the doorbell and I was met by a very attractive woman. She introduced herself as Joanne.We...

2 years ago
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Chrissys Journey to Becoming a Woman Chapter 2

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2 years ago
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Jennifers Journey Becoming the Perfect Housewife Part 16

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2 years ago
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Jason Becomes Joanne

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3 years ago
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Jennifers Journey Becoming the Perfect Housewife Part 10

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2 years ago
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Jennifers Journey Becoming the Perfect Housewife Part 14

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2 years ago
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Jennifers Journey Becoming the Perfect Housewife Part 18

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2 years ago
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Jennifers Journey Becoming the Perfect Housewife Part 5

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3 years ago
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Jennifers Journey Becoming the Perfect Housewife Part 11

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1 year ago
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Jennifers Journey Becoming the Perfect Housewife Part 12

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Jennifers Journey Becoming the Perfect Housewife Part 9

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1 year ago
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Becoming Suzanne A Womans Journey

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1 year ago
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Becoming Suzanne A Womans Journey Part 3

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3 years ago
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Jennifers Journey Becoming the Perfect Housewife Part 6

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4 years ago
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Journey into Cuckoldry Six of the Best

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Cuckold
3 years ago
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Jennifers Journey Becoming the Perfect Housewife Part 8

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3 years ago
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Becoming Suzanne A Womans Journey Part 5

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2 years ago
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My Journey To Becoming A Bull

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1 year ago
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My Sensual Journey Part One

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1 year ago
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Becoming A Slut Wife Joanna

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2 years ago
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Wifes journey to becoming a slut

I have several stories relating to this journey so will start at the beginning.My name is Bill and her name is Debbie.We were young married and both adventurous I had no idea how wild my wife would become. We had c***dren within the first year and from there even though we had an active sex life it was getting mundane. Deb was always open to things as loved to show off her beautiful legs ass and tits. Loved to wear skimpy shorts and tube thops that showed off her big nipples. Access was very...

3 years ago
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My Journey to becoming a BBC Queen of Spades slut

This has been a long journey that has been over 2 years in the making but it was worth the wait. It started when I was able to be completely open and honest with Master and share my fantasy of being with black men and being a Queen of Spades. He was so accepting and supportive of turning my fantasy into a reality. It wasn’t a subject we discussed everyday but it was always there in the back of our minds. I knew it would happen when the time was right but I didn’t know when that would be....

2 years ago
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Temple of Torture Vanessas First Journey

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1 year ago
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Finding My Femininity A Journey of SelfDiscovery and Love

I was always a good boy, never causing any trouble or needing to be disciplined. But then my mother came up with the idea that I might like to wear a dress, and I was terrified. I didn't want to be seen as a sissy or a girl, but my mother thought it would be good for me to explore my femininity. When she presented me with the Punishment Dress, I was confused and scared. I didn't know what to think, but my mother insisted that it was a punishment for something I had supposedly done...

3 years ago
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Journeys

Every journey has a starting point, but sometimes it’s difficult to tell if there is a destination.Sometimes you just start rolling and you end up someplace you never imagined.That’s true of any journey. Even an innocent bike ride on a warm summer morning.The starting point. A middle-aged man with a wife and kids, not entirely happy but not entirely unhappy either. Happy with most things except between the sheets. It happens to a lot of marriages, after the kids come along. After the partner...

Love Stories
2 years ago
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my journey to becoming a cuckhold

My wife and I have been married only for a few months when our sex lives started to change. We had lost contact for many years as we were both previously married and reconnected later in life. Lynn is is buxom brunette that is a little on the plump side. Since rediscovering each other, we spent lots of time talking about what we had done sexually over the years. Lynn was facinated with the fact that I have been very adventourous. I have been into anything extreme. I loved cock as much as pussy...

3 years ago
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Janels Journey With Becoming A Jizz Dependent

The Situation.It happened a few years ago, the world had been getting stranger by the day. Could it be do to more and more people learning and using occult chaos magick? Our lady Eris must sure be grinning with this most6 resent, most bizzare, and more exciting change to have befallen planet Earth. Some sort of random sexual virus came into the world. It sprang up randomly and without rhyme nor reason with whom contracted it. Those whom did were very secretive about it lest people findout and...

1 year ago
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Journey into Cuckoldry Sweet Sixteen

The days had passed slowly but they had eventually passed. It was Saturday - THE Saturday. The night my wife was to become a whore! It was ten thirty in the evening. I was sitting in the same booth in the same bar in which Julie, Gary, Alice and I had started our New Year’s Eve celebrations but this time the bar was barely a quarter full and I was sitting there alone, apart from a tall glass of ice cold beer. My tummy was bubbling with excitement but, I suspected, not as much as those of the...

Cuckold
2 years ago
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Journey To Work And Mary My Mature Nylon Tights Pa

A story of how my boring mundane work journey was made bearable by fantasising about a lady who used to get on my train each day, her inspiration for this story came from her gorgeous nylon clad legsthe lady was real sadly the story is made up...One day on the train to work, the mature lady who most days i shared a train carriage with on the way to work, asked if I liked what I saw when I overdid the fleating glances at her vey smart work attire.Her attire of smart black blazer, white blouse,...

1 year ago
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The Journey

THE JOURNEY By Anne Gray Note: I originally posted this story in 2003, complete with the usual mistakes made by would be authors, in five short chapters. I am very grateful to Vickie Tern for the advice and comments that, I hope, make this revision a better story. It tells of the Journey a young man makes to fulfill his dream. The category is crossdressing and the code G; the story is complete. Chapter...

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