Jackie Begins her Transition

All characters are 18+

Also this is the 2nd part to this story. Reading the first, "Taking Mom's Place," makes it much more understandable and enjoyable.

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After that second day with Martin, Jackie began to settle into her new rhythm. She began her actual transition, beginning to take testosterone suppressors and estrogen supplements, growing out her hair, working out daily, and practicing everything that she loved. Martin's life improved rapidly having a "wife" again, waking up and kissing her goodbye, coming home to a nice home-cooked meal, and making sweet love to her until they fell asleep. And Jackie was loving her life more than ever, too. She began to make rapid progress, her workouts shaping her body in amazing ways, and the hormone supplements doing some outstanding work. She was told that she should expect her breasts to get to about the size of the females in her direct family, and given both her mother and her sister were quite busty, this made her pretty happy.

Martin and Jackie didn't tell Jackie's sister yet, they were planning to do it when it would be best, so for the first month and a half they were in their own little bubble. As Jackie got more and more passable, she started to go out of the house more and more. Her butt was filling out, her waist shrinking in, and her breasts developing paired with her ever feminizing face and growing hair meant that she even began to catch some attention while outside. She went on runs, something she would have never even considered as Jack, and she loved the feeling of strangers eyes on her. Overall, she was just loving her new body.

Jackie full-time moved into the master bedroom, and her and Martin converted Jack's old room into a guest room. Jackie took full ownership of her mom's old clothes and things, and began to fill in the closet with some of her own stuff. The house was kept constantly clean, and Jackie never slacked on her duties around the house. She got quite good at it, slipping into a groove as she put on some music and danced around the house keeping things tidy. Martin never had to worry about those things anymore, and they helped Jackie stay occupied while she was essentially a stay-at-home wife. They talked about Jackie getting a job, or going out and finding some friends or something else to keep herself occupied, Martin hated for her to be stuck at home all day, but Jackie didn't want to do anything until her transition was complete.

Jackie's mid-length brunette hair grew out quickly, and by this time it was a few inches down her back and past her shoulders. She studied up on how to keep it as nice as possible, and had many shampoos and softeners to keep it as flowy and soft as it could be. Martin loved her hair, as did she, and it reminded both of them of Jackie's mothers. In fact, many things about Jackie began to resemble her mother. Her voice as it got higher and more feminine became eerily similar to her mothers along with her body figure, and her character too. Starting the first few weeks into the transition, Jackie began to feel her emotions stirring wildly. She was warned about this, but as it happened she had never experienced such beautiful and vivid emotions. She felt massive mood swings, but she also began to see things in such a more beautiful way, and she loved it.

As she got better and faster at her house work, she began needing a few other things to tackle to occupy her time. She began gardening in the back yard, reviving and sustaining the rose bushes and flowers in the back. After some time the backyard looked almost as good as it did when her mother was still in charge of it, and it became one of her favorite hobbies. She even planted and maintained some bushes in the front yard too. She would go out in the afternoons, in her jeans, white tee-shirt, sun hat and gloves and go tend to her plants. As she did so, she got to see the life of their street like her neighbors in confusion at the sight of her walking up to introduce themselves. She always introduced herself as Martin's niece, as she was obviously too young to be his actual wife, and they were all happy to hear that Martin had found someone. Jackie worried that they might see the irony between her name and Martin's son, but none seemed to notice, probably because none of them really knew Jack because he had spent all his time in doors. Getting to re-introduce herself to her neighbors really helped her, especially meeting their next door neighbors, the Smiths, again.

The smiths had always been there, as long as Jack had, and they were always a nice folk. Their son, Robin, was two years older than Jack, and had never much associated with him as he was more of the athletic, jock type. He did talk to Jack's sister, but she was still too old for him. One day, Jackie went outside to tend to her flowers and Robin was out mowing the lawn. She waved and said hello then got to work. As she worked, however, she noticed that he was very interested in her, staring at her for long periods of time. She always loved attention, so she put on a bit of a show for him, bending over and sticking out her butt a bit. She knew that he hadn't interacted enough with Jack to have any suspicion about her, so she took all of her liberties to toy with him.

As she did love attention, she kept posting photos of herself online. She kept an almost day-by-day log of her transition, and soaked in the love she got online. Occasionally she posted some lewd photos, which always got her tons of support and sexy comments, but she always felt like she wanted to reserve herself for Martin. But she couldn't fight how much she enjoyed men's attention, it started to become a problem as she toyed with them whenever she got the opportunity to. On her runs, while gardening, while shopping, and even while out to dinner with Martin. She couldn't help herself from being a tease. Martin noticed, but as he was adamant that he didn't want her to be tied down to him, he supported her and her flirtatious habits.

The only other thing she loved from men more than their attention was their loving. She became well educated in the art of being the submissive bottom during sex. Her and Martin explored everything and anything sexual, even breaking out the bondage gear Martin and Jackie's mother used to use. She got to the point where she could take every inch of Martin's 9.5" dick in both of her holes, and she could come multiple times while having sex with her pathetic, caged clitty. She was becoming quite the nymphomaniac, and neither her or Martin could deny nor object to it. Martin never had as wild or deep of loving with Jackie's mother, and Jackie had never felt so deeply stimulated and satiated. Every time she had Martin's member in her or on her, she felt herself go a little dick crazy. It even happened when she got private messages online from followers sending pictures of their own dicks to her, she couldn't help but toy with them a bit.

But all around, Jackie and Martin were both loving life. Each of their regular days had become much more exciting and optimistic, and they were enjoying their time. So almost two months later and Jackie was having a regular day. She had just finished her workout and was changing into her gardening clothes. Her jeans were beginning to tear, but she didn't mind, and she put herself together with a bit of makeup and her sun hat and went downstairs. She grabbed her things out of the garage and went out back to start. She did her rounds, clipped her hedges, and watered her plants in the backyard and looked at her handiwork. It was looking awesome, and she was extremely proud of herself as she walked around the side yard and into the front. She walked up to her flowers on the front grass and noticed Robin was out on his driveway playing basketball. She waved at him and he waved back, and she paid no more mind to him.

She found him attractive, and given they were both pretty similar in age she felt a very weird attraction to him. He was well built, very athletic with a broad chest and shoulders and muscular arms. His face was strong and his jawline was fortuitous. He had short, tossed blonde hair and blue eyes. He was wearing a pair of basketball shorts, shoes, and a muscle-tee with the sleeves cut off. Needless to say, he was attractive and Jackie wouldn't disagree. She didn't want to complicate things, however, so she tried to keep things as quiet as she could around him and tried to make sure she didn't take things too far. They had only talked at length once, and the rest of their interactions had been short greetings. So she got down and began to work on her flowers.

She was halfway done with her front yard when she heard a bounce behind her and the ball roll up and tap her foot. She stood up in surprise and turned to the basketball sitting by her foot. She picked it up and looked up to find Robin walking toward her with a laughing grin on his face. She held the ball out to him as he approached and he took it out of her hands, saying, "Sorry about that, I'm working on my shot."

"No problem, as long as it hit me and not my flowers." Jackie joked.

He laughed a bit and hesitated with a look of contemplation on his face, "Jackie, right?"

"Yeah."

"Awesome. Takes me a while to remember names."

"Yeah I understand that, I'm the same way."

"So, you look college age, do you go to school?"

"Well, I did, but not any more. It wasn't for me so I moved back in with my mom and Martin before I can figure out what I'm doing." She had practiced that lie, ready for this exact question.

"Ah, yeah I understand. I go to the junior college and am trying to transfer to a D1 for basketball."

"Oh that's cool, do you have any idea what you want to major in?"

"Whatever is easiest to let me play basketball, I guess." He laughed.

She genuinely laughed back, admiring his demeanor and charisma. He was definitely the type of guy that you envisioned as the perfect jock who gets all the ladies, "That's funny. I hope you find somewhere."

"Thanks. So how old are you then?"

"I'm turning on twenty. And you?" She asked, fully knowing the answer.

"Oh cool, I'm twenty-two. I haven't seen your mother around, only you. Is she busy?"

Jackie was also well prepared for this question, "Yeah, her and Martin are both really busy. Martin, being a lawyer, is busy all day and my mom is a representative for a big company that sends her all over the place."

"Oh that's awesome. So they just leave you alone all day?"

"Yeah, it gets kinda boring, which is why I take care of the gardening and stuff." She said, motioning to the flowers.

They went on talking for a while. And with every passing word, Jackie found herself admiring Robin more and more. He was extremely fit, and she followed the creases of his muscles on his arms with her eyes as she talked. He was really funny, and she found herself extremely drawn in by his words. She hadn't really flirted before, unless you consider being a tease with your body, nor had she been flirted with yet, so she wasn't sure how to feel or act. And she didn't realize that she had played right into his hand when he commented how hot it was out and she said, "Yeah it really is. I don't see you drinking anything, are you sure it's the best idea for you to be out here without a drink?"

"Oh I'll be fine, I drank some water before I came out here."

Practically melting in his hands, she said, "Oh that's not good enough. You're really sweating and red, here come inside let me get you something to drink." And she led him inside.

As she led him up the porch and into the door, she could feel his eyes on her butt. They walked into the kitchen and she grabbed a plastic cup out of a cupboard. She placed it on the island and opened up the fridge. He commented how clean everything was and she thanked him. She pulled out the lemonade and poured him a glass, he thanked her and began to drink. They kept chatting about all sorts of things. He asked about her time in college, things like parties and sororities that she had been a part of. She hadn't thought about these things so she had to make it up on the spot. His questions kept getting more and more personal and she started to get more and more heated trying to answer them. Finally he finished the lemonade and asked if she had a boyfriend, to which she said no.

"Really? A beautiful girl like yourself? Why not, haven't found anyone good enough?" He said, slowly working his way around the island.

"No, I just didn't want to deal with it while I moved back in with my mom."

"So you were dating in college?"

"N-no, I was mostly interested in socializing and things. Didn't get that far before I left."

"I'm amazed, guys at parties must have been all over you." He said, now by her side and beginning to lean closer.

"Well I don't know about THAT." She said, playing the fool.

"Well I do. You're gorgeous, any guy's dream," He said, now reaching his hand around her and placing it around her lower back, "Your face is beautiful, your eyes are gorgeous, your hair is like an angels."

She found herself unable to respond as she stared into his eyes, amazed at how far she'd been caught. He didn't say anything else as he leaned in and planted his lips on hers. They began to make out, as she turned to fully face him and stand up. His other hand came around and planted itself on the top of her butt. Both his hands now began to explore, tugging at her jeans and peaking fingers into the top of them. She was completely melting into his arms, and she couldn't find any strength to stop him as he groped her. If it weren't for the months of cage training, she would be getting very hard right now, much like her nipples were beginning to get.

Their kiss got sloppier and more heated as they began to explore each others mouths with their tongues. He was now molesting her ass with both hands, and she pulled herself into his chest. Her leg pressed against his and she could feel his hardening member through his basketball shorts. They made out for a long time, the minutes falling away as the two only took momentary breaks to catch their breaths. Finally, however, he began to shift her out of the kitchen and lead her to the couch. They got there with a stutter and they fell backwards onto it, leaving Jackie on top of Robin, their kiss unending. They kept their faces locked together for a few more minutes before Jackie decided to take initiative.

She pulled off of him and rolled off the couch. He sat up straight and was about to ask her why she had left when she reached for his shorts. A sly grin crossed his face as he realized what she wanted. She was hungry for more than just a kiss, so she clawed for his shorts and began to tug. He helped her pull them off and lifted himself up a bit to pull down his boxers, and suddenly his nine inch member sprung free in all of its glory. It was slightly shorter than martin's but maybe a bit girthier. She marveled at it and grabbed it with one hand, it's heat radiating into her hand. His hand found the back of her head and he was lightly nudging her to get closer to it, but she didn't need any push. She closed in and began to kiss and lick up and down his cock. He was amazed at how quick to work she was and his hand had to catch her head.

He was being impatient and started to use more force to push her head up to line her mouth up with the top of his cock. She knew what he wanted, and she wanted it too, so she let him position her mouth right at the top of his cock. She wanted to impress him right there, so she left his hand hanging as she shoved her head down the length of his cock, devouring every inch of it before her nose stuck into his pubic hair. The smelly, sweaty musk that hung around his crotch filled her nose and she was drunk with his manliness. He was in shock that she had just taken all nine inches with one go, something he had never seen another girl do, and his hand just hung there. Finally she began to bob up and down on it.

She showed him a real good time, using every bit of skill she had earned with Martin as she rocked his cock in her mouth, popping it in and out of her throat at ease. Her tongue played with it like a lollipop and she was able to maintain eye contact most of the time, maintaining a cat-like look of catching her prey. He was losing it, leaning back and moaning in the ecstasy of her skills. Both hands now planted on her head as he tried to force her into a rhythm, but she showed no sign of needing his help as she dropped down and pulled back up on his dick. His moans grew louder and louder until his grip on her head began to grow tight and mess with her hair.

He growled at her, "Damn, girl, you're gonna make me come so fast."

And she just kicked it into high gear. She felt his dick tense up, ready to unload his sperm, and she dropped all the way down and held it there. He released rope after rope of come directly into her throat, and she was able to hold him there until he was done, swallowing every bit of it. Finally she pulled all the way off and sucked in a breath as she smiled at him. He was lost in a world of joy as his body lay limp on the couch. He looked at her and laughed, "Damn. You're the best cock sucker I've ever met. You're actually amazing."

"Thank you." She said standing up. She turned and acted coy as she bent over slightly, presenting her ass to him in a taunting way, knowing he didn't have anything left in him. In response to this he just slapped her ass and complimented her on it.

She insisted then that she had things to do and that they could talk later, rushing him out of her house. He refused to leave unless she gave him her number, so she wrote it on a little piece of paper and sent him out the door. Once he was gone she turned and thought about her experience, her stomach full and her heart pumping. She felt guilty for cheating on Martin, but at the same time he had given her complete freedom to do as she pleased so it was REALLY cheating, and she loved it too. Later that night she got a text from him and they began to talk.

Jackie felt bad about it still, so when Martin got home she told him what happened. He wasn't at all hurt or surprised, and in fact, supported her finding new people to "talk" to. But since she couldn't fight the feeling of cheating, she made it up to him by riding him all night. The next day Jackie and Robin started to thoroughly talk. She began to send him pictures, too, from her working out and getting dressed. She knew, however, that he wasn't going to eventually find out that she was a sissy so she started to think about what to say. A week after their first time, Jackie texted him asking him to come over. He was over in a flash and they kissed as he walked in.

She asked him to sit on the couch and they could talk. She started by explaining what their relationship was, purely friends with benefits. Then she began to go deeper. She knew that she still couldn't tell him who she really was, nor what was actually happening at her house so she had thought up a story to tell him that seemed pretty believable. She told Robin that her mother and her used to live an hour away before her mother got a transfer. But she also used to have some major gender dysphoria before high school, and soon she began to transition into being a girl. She went to college but came back, and at this point she was basically done transitioning. He was stunned to hear this, and a little upset too that he had been toying with a trans girl. He didn't believe it, so she right there pulled down her pants and panties to reveal her caged clitty.

he didn't know what to say so he sat there in pouting anger and confusion. She knew how to handle this, though, as she dropped back to her knees and began pulling down his pants. He didn't help her, as he was still upset, but he didn't stop her either. She told him, "It shouldn't matter that I was a boy, because now I love to be the girl. My penis is caged because I'm not a boy, and you'll never see anything boyish about me, I can promise you. Besides, who cares that I've got a cock when I can do this." And she then took his cock down all the way into her throat in one go. He tried to fight the ecstasy but he moaned a bit and broke his stern look. She then kept sucking until finally he broke down and ordered her to stop. She knew what was coming so she immediately stood up and leaned over the couch.