Taking Mom's Place

Editor's note: this story contains scenes of incest or incest content.

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*All characters are 18+ years old.

This is the first entry to this story, so if you like it I can continue it.

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Jack walked back into his old room with his suitcases in tow and couldn't help but feel the shame and sadness that lingered there. He knew that his father was extremely disappointed, and extremely sad about the situation, too, which didn't help Jack's state of mind. He threw his bags onto his old bed and sat down on the side. He had just flunked out of college and had to move back into his dad's house. That alone wouldn't have been too much for either Jack or his dad, but with his mother dying only nine months ago, that was the kicker. It's what too away Jack's drive to work hard in college, and it's what killed Jack's dad's happiness. Jack's dad, Martin, loved Jack's mom more than anything, and despite Jack and his sister trying to help him to move on, he never recovered really.

Jack was now back and living in his childhood house, but with the biggest part of his childhood dead the house didn't feel at all the same. Martin moped around, slowly and depressed, while Jack tried to stay in his room out of shame. Jack sensed the disappointment in Martin, but neither were in the moon to confront any problems. So, for the first week or so, Martin and Jack went about their own but separate lives in the same house. Martin left for work at seven, came back by six, and then usually either drank himself to sleep or goes out to bars with his two friends. Meanwhile, Jack stays at home all day on the computer and finding ways to entertain himself. All of his childhood friends were still in college, leaving him no one to connect with.

But Jack found ways to pass the time, and a lot of that went to masturbating. Jack wasn't a total lost cause, but when it came to girls he was pretty close to it. He had only ever dated a girl for a month in his senior year of high school, then never could get another. He had lost his virginity, but he didn't last long and he never got a chance to try again. And so, porn was one of his closest friends. It started when he was a freshman in high school, and it started off with normal tastes. But with time he got bored of that and started trying new things. By the end of his sophomore year, he had found a genre of porn that piqued his interest. It was called 'Sissy' and was all about feminine boys being forced or choosing to become girls. He was interested, and it soon grew on him.

Back then, he eventually got into trying cross dressing a bit as he snuck into and tried on his sister and mother's clothes. But his mother caught him and talked to him about it. His mother was the sweetest thing, and loved him dearly, but she didn't want him to get in over his head. He explained to her that he wasn't gay, just interested in feminization a bit, and she saw fit to help him through that phase. She taught him some starters on how to do his makeup, dress, and even act a bit, all without Martin knowing. Jack always loved his mother the most, because she was the most understanding and caring. With her help, Jack exhausted his interest in being a sissy and forgot about it, as did she. But now, with all this free time back in the house he used to live in, he reopened some sissy porn and got thinking.

Jack had mid-length brown hair, lightly tanned skin, brown eyes, and a smooth face. His facial features were small, as was the rest of him. He was abnormally short, only about 5'7", and he wasn't very well built. Not very muscular, wider hips for a boy, and all around skinny and shaped more like a girl. As a boy, he wore baggy clothes usually to hide these things, but they all helped him in his cross dressing. He looked at the tabs of porn opened on his computer, filled with pictures of sissies, and he recalled back to his time dressing up. He thought about what he thought then, and he tried to put himself in that mindset. He was on his favorite site, one with a sissy forum for people to share pictures and comment.

It was one in the afternoon. Mat had eaten lunch, his dad had been gone for a while, and the house was empty. He looked at the pictures and read the comments, still amazed at how much support sissies got. He had never shared any photos, but he had seen many photos and many uplifting comments. He found one 'girl' that looked a bit like him, same height, same hair, same eyes, and same face and he could envision himself as her, posting his pictures. Mat took a few minutes to build his confidence, then stood up from his chair and walked out of his room. He walked down the hall and into the wide double doors leading to the master bedroom. It was clean, but very empty, two things it never used to be while his mother was alive, and Mat looked around. He saw the closet and dresser that belonged to his mom, where he got many of the clothes that he used back then, and he walked up to it. He opened it revealing all of the same stuff still there. He then opened the closet revealing the rest of his moms things.

She had quite a shoe collection, along with many nice dressed and a plethora of pants, skirts, shirts, and stockings. Mat grabbed a pair of skinny jeans, a white blouse, a black lace bra, and the panties to match. He then grabbed a pair of wedges and some socks. He brought them into the master bedroom and laid them on the counter. Next, he left the master bedroom and went for his sisters room. He found that everything was still there, despite his mother talking about moving this stuff into storage, including Jack's sister's collection of wigs. His sister went through a phase where she shaved her head, then immediately regretted it and had to get several wigs. There was a long brunette one, a short blonde one, and a curly red one.

Mat always liked the brunette one the most, not only because it was like his own hair but because it reminded him of his mom's hair, beautifully long and smooth with the color of rich chocolate. So he grabbed that one and a few other things and went back to the master bathroom. He rummaged around in the drawers to find all of his mothers makeup, and sure enough it was all still there in the same bags as ever. He laid them all out on the counter then went back to rummaging. He found his mom's razor and lotion, and to his surprise he found some nair hair remover and he grabbed that too. He then began to run the shower and took off all of his clothes. He stepped in and began to shave his whole body.

He started up on his chest area, shaving what little bit of chest hair he had, then his arm pits, and moving downward he got to his crotch. He shaved away his pubic hair, leaving a smooth and clean part of skin above his pathetic 3" dick. Eventually he got all the way down his legs and feet, and after washing through some of the nair and finding some of his mothers sweet smelling body washes, he stepped out and was completely smooth. He rubbed the lotion all over to complete the feel and smiled at himself in the mirror. He had some smooth and sloping shoulders, also like a woman's, and with no hair his legs were like that of a woman who didn't work them out much. He sat down in front of the vanity mirror and began to get to work.

He recalled as much of what his mom had taught him, but had to look up how to do a lot of the other things. He worked layer through layer of his makeup, applying some red blush, red lipstick, black eyeliner, and dark pink eye shadow. He plucked his eyebrows a bit to give them some more feminine shape, he painted his nails red, and he finished it off by clipping on some fake earrings he grabbed from his sister. It was a simple, but sexy look. He then slipped into all of his clothes and looked at himself. He looked more feminine than ever, even back when he had his mom help him, and he thought about what he used to call himself the.

His mom had told him that while he was dressed up as a girl, he was one. And if she was a girl, then she needed a name. She picked the name Jackie, and despite her mother rolling her eyes and laughing at the irony, she stuck with it. She then whispered to herself in the mirror, "Welcome back, Jackie."

She left the bathroom and into the bedroom. She stood there, and realized that though she had spent about an hour getting ready, she still had not much more to do. So, to entertain her boredom and to please her curiosity, she continued to go through her mom's things. She shuffled through her boxes of old photos, shoes, and dresses and crawled through the pile of junk in her closet. Eventually, Jackie found a box tucked away on the top shelf of the closet labeled, "Toys."

Jackie brought the box out to the bed and opened it up, gasping. Inside were a few things, a 7" see-through dildo with a suction cup on the end, a 9" black dildo with realistic veins and balls, a metal plug with a 2 inch diameter, and some gimp things including a whip. Jackie had never known about this side of her mom, but realizing it was making her as hard as ever in her jeans. Then she remembered the dildo that her sister had that Jackie had found all those years ago. Jackie couldn't help it, she ran back to her room and jerked her little dicklette off until she came. A little bit of her come landed on her hand and she stared at it. She had seen so much sissy porn, and so many stories that her immediate thought was to taste it. Before, she would've said no, but now she wondered what the worst could be and she did.

The bitter taste hit her with surprise. She hadn't even wondered what it would taste like, but this was not it. It wasn't bad, but it also wasn't her favorite. She had licked all of it off of her hand, but she wondered if maybe a second taste could help her decide whether she liked it or not. So she reached with a finger to a bit that had landed on her chair and scooped it up and into her mouth. This time it was a bit better, maybe because she was expecting it, and she thought that she needed to try more to be sure. All the rest was in some toilet paper, so she had to jerk off again to get what little came out. This time she caught it all on her hand and lapped it up like a dog. It was beginning to grow on her.

She cleaned up then went on to entertain herself for the next few hours. She stayed dressed up as she frolicked around the house, pretending to do chores and fulfill womanly duties. She went into her backyard to get some air and sat on the deck for a while. She grabbed her phone and took some photos of herself around the house, and while taking pictures she thought about some of the things she had seen sissies online do in photos. So she ran upstairs and grabbed the smaller of the two dildos out of the box. She set up her phone in her sisters room and proceeded to take some photos of her licking and starting to suck the dildo. It felt weird in her mouth, but the photos turned her on.

She went back to her computer and uploaded those pictures to her favorite porn site along with the caption, "First time posting as a sissy. Just a little taste!"

She looked at the time and saw that it was somehow 4:30, and she jumped out of her chair to run back and clean up the mess. She cleaned the closet, drawers, bathroom, and shower. She took all of the things she had used back to her room, along with the box of toys and clothes. She quickly took all of the clothes off and took off her makeup. Right as she slipped back into her boy clothes her dad walked in. And with that successful first day, Jackie's visits became a common thing.

Jackie got ready and had her time to play almost every day after her dad left. She did almost the same things every day, dressed, masturbated, played with the toys, frolicked, and took photos. She always posted the photos she took online, and she was beginning to see comments that were giving her some serious confidence boosts. She was beginning to enjoy life again, jackie's fun excursions being the only bit of light in her day. She laughed and smiled as she danced about the house, beginning to become so enthralled in what she did. She got better at her makeup and dressing, watching videos and reading guides on how to improve. She read these posts online to sissy forums about how to be a good sissy, she read them as a joke but she actually began to take lessons out from them. All was well for the time.

Over the next few days she improved at being a girl, through having chat conversations online with people who commented on her photos. She practiced with her body, too, and she practiced every day sucking her dildos. She tried a couple times to fuck her sissy hole with one, but the pain was great and she wasn't too eager to start, so she didn't get too far with that. She practiced her voice, and got really good at it, while chatting with strangers on chat websites like Omegle. She got a lot of requests to do sexy things, some of which she was glad to do, but most of the time she just closed the chat when things got too weird.

One morning she even found a routine online that was supposed to help with her feminine figure, including some yoga and small exercises. So, she rummaged through the garage and found her mom's old yoga and workout sets and brought them up to the master bedroom. she got dressed in a simple and flexible get up, checking out several pair of stockings in the process and throwing them on the bed, then began to stretch. She had only done yoga once before, with her mother as a young kid, and she wasn't too good at it. But at least this time, she felt a drive to keep up with it. She did a lot of squats and sit ups with her workout routine, and she was surprised to see how quickly she started to see results, her core shrinking and becoming more toned than ever, and her butt getting quite shapely in a nice bubble butt.

Then, two weeks later, Jackie was out and about doing chores. The house had gotten a little messy, and Jack's dad asked if he could clean the house a bit. So, Jackie was dressed with an apron on and was going about the house cleaning and humming away with joy in her heart and excitement in her dicklette. She sweeped and cleaned the floor downstairs, something her dad didn't even ask her to do, and cleaned and wiped the counters in the kitchen. She was finishing up the house and it looked cleaner than it had when Jack moved back in. She was dusting some things when she heard the door open.

She turned with a fright to see her dad there, dressed in a suit with his briefcase in his hand and a peculiar look on his face. His older face showing every sign of age, and his short, grey hair combed neatly. He stared at her as she stared back, her face getting red like a tomato. He calmly moved to the island in the center of the kitchen and placed his suitcase down, saying, "You look just like her, you know... If I didn't know she had passed, I would almost think you were her."

Jackie didn't say anything in her shock, so Martin went on, "I had thought something was up when I noticed some things out of place in the bathroom. Then I found a pair of stockings out by my bed and I knew it was something with your mothers stuff. Indeed, I began to notice things disappearing. I didn't know if you would go for it, but I asked you to clean to see if you would react like your mother always did. And here you are, in her apron, and the house looks spotless..."

Again, Jackie just slowly turned to completely face her father. Marrtin asked, "Are you nervous? You seem very nervous."

Jackie finally choked out the words, "Yeah. I guess."

"Well, I don't think you should be. Your mother told me about your time as Jackie when you left for college. She wanted to tell me after you had gone in case I didn't respond well to it. It shocked me, but it didn't bother me. I really didn't mind my son preferring to be my daughter. But this is different, no this bothers me in a different way, because you're not trying to be a daughter. You're trying to be My loved wife."

"Wh-What?"

"You're dressed like her, your makeup is exactly as she did hers, your hair is hers, your face, and even your body. Granted, yours isn't such a figure but it's as close as a boys can get to that, I think."

Jackie had to pause and look at her hands, worried about losing her home, and asked, "And, that bothers you?"

"As I said, it bothers me in a different way." He said, his face never failing to stay calm, "Because it's too perfect. You are her. And it bothers me because I fear what I could do wrong to lose her again."

This hit Jackie like a train. She felt dizzy and the world spun a bit. She shook her head and just mumbled, "What?"

"It's ok. I knew I could never find the right words. But seeing you gave me a bit of hope for another bright day. Look, I fucked this up and I made it weird for you, so I'm sorry. I'm going to go to the bar, and you could get back to what you were doing. Forget that I said anything, I'll leave you a card so you can get yourself dinner." And with that, Martin pulled out his wallet and left one of his credit cards on the island. He closed his suitcase and then walked back out of the door, the same look of depression replacing that peculiar look on his face. He left and went to the bar, leaving Jackie with a red face and a broken heart.

She felt so bad for her dad. She was only now figuring out what he was talking about. He saw her and could only see her mother, and that really hit him. It gave him some hope of feeling happy again, reunited with his wife. And he fears that he scared her away from being this. She hung up the apron and went to her room. She sat against her wall, lost in thought, and a few tears welled in her eyes. She looked at her hands, her nails red and her skin soft and smooth. She didn't know why, but all she could see were her mothers hands. She hugged herself and tried to picture her mother hugging her. She had hidden the pain from losing her mother down inside as best she could, and she realized that her dad had done the same.

She never got dinner that night, and never left her room. She looked over her old texts with her mom, and her old photos with her in them. She saw her mother quite clearly, but any one with Jack in them just seemed blurry. After being told how much she was like her mother, all she could think about was being her. And that wasn't the bad part, the bad part was how it almost made Jackie feel a bit better about her death. In being her, it kept her a live, kinda, inside of Jackie. She heard her dad stumble in and go to his room. She was still dressed up, and trying to ignore the crying she heard coming from the master bedroom as she fell asleep. But she couldn't ever shake the guilt, and she dreamed that night of her mother.

In the dream, it was her as younger Jackie getting taught by her mother how to apply lipstick. Jackie asked about what her dad would think about this. Her mother thought about it and said, "He's open minded but somehow also stubborn in a way. I don't think he would be opposed to it, but I also don't think it's what he would want to hear." Young Jackie looked down and at her hands. Her mother then said, "But, that's not to say he doesn't support you. He would support you whatever you do, wherever you are. He loves you, and he just wants whats best for you."

The dream shifted and changed, and suddenly she saw herself as her mother sitting at Jack's graduation, with Martin sitting next to her. She watched as Jack walked up to the stage and took his diploma, shaking the hands of his principal and teachers. Martin's hands grabbed hers and she leaned onto Martin's shoulder. Things changed again and suddenly she was younger, and so was Jack and Martin. Jack was only a freshman and she was sitting with him talking to him about Jackie. She smiled at Jackie, and she said, "You're so cute like this. You remind me of myself. If you stick with this, and it becomes you, I want you to be like me. living her best life with a great guy, like Martin."