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My Personal Hero
By RogerGirl

"Mom, can you help me with something?" my older son asks calling to me from his room.

"What is it honey?" I ask as I come in his room.

"I don't want you to freak out or anything, but can you dress me up like you?" he asks nervously.

"You want me to dress you up like a woman?" I ask a little surprised.

 Jake has never shown any interest in cross-dressing before and he has a girlfriend, so I admit I am a little confused.  Maybe he's been holding this in for a while and has finally decided to come out to me.  

"I should probably explain before you jump to any conclusions," he continues, "This isn't some kind of desire to dress as a woman or anything, I'm doing this for school.  I have to do a photo project where I dress up as my personal hero and show myself in various scenes explaining why this person is my hero."

"And you chose me?" I ask a little taken aback.

"Of course mom," he replies, "After dad left us you raised the three of us by yourself.  You had a full-time job and were still able to be there whenever we needed you.  Why wouldn't I choose you."

"Well, I appreciate that," I say with pride, "but wouldn't it be easier to do the project as your favorite athlete or a historical figure you look up to."

"I could, but they aren't my heroes, you are," Jake responds.

"Well, if we are going to do this," I continue trying to see how committed he really was, "You will have to spend two days living my life, a weekday and a weekend.  That means everything I do.  Are you OK with that?"

"Yes mom," he answers, "You do this for us everyday of the year.  The least I could do is spend two days in your shoes."

 Oh, I'm so proud of him.  I hug him and we make plans for the project.  Since senior ditch day is coming up on Friday, he will instead spend the day with me.  I tell him it will mean giving up going out with all of his friends, but he doesn't seem to mind.  I also tell him he will have to remove his body hair and again he agrees.  In the next couple days, I begin making preparations for his transformation.  I buy him a pair of realistic breast forms and a prosthetic vagina and buy him a couple sets of underwear in the style I wear.  I am in my late 30s and I have a boyfriend, so I often try to dress up nice.  People have always said we look a lot alike and I guess this weekend I am about to see just how alike we look.        

 On Thursday, I pick him up from school and take him to my salon where I have made an appointment for him.  I had explained the situation to the ladies there and they all thought it was very sweet what he was doing.  When we arrive, they are all over him and shower him with praise.  Jake's hair is long like mine is and I instruct the ladies to give him the same hairstyle as I wear.  Prior to arriving I had him remove his body hair and put on the prosthetics I had bought for him.  He is wearing his new underwear under a pair of jeans and a sweatshirt.  I made sure to get the breast forms in my size, and unfortunately for Jake mine are a C cup.

 They take him to the back where he changes into a simple skirt and blouse outfit and the ladies wash his hair.  Soon, Jake is engulfed in a world of femininity.  His hair is dyed, cut, and styled (he has been planning to cut his hair for a while and will cut it after the project), his eyebrows are shaped (only slightly so as not to make him look to feminine when this is all over), he is given a manicure and pedicure and his nails are painted, and his makeup is done.  I wait in the waiting area reading a magazine so as not to ruin the surprise when it is all over.  

 After waiting quite some time, the ladies instruct me to come on back.  I step through the curtain and see a beautiful girl standing before me.  My son's normally brown hair is now a light blonde, his lips look thick and full, and his eyes and eyelashes look amazing.  The blouse shows off a hint of cleavage and the skirt and heels make his legs look long and shapely.  It is like looking at myself at 18.  Before I forget, I make sure to take a few pictures of him for his project.    

"Do I look OK?" my pretty son asks me nervously.

"You look beautiful," I reply as I take him into my arms and hug him.  

 We grab his things and I hand him a purse as we head to the middle school and elementary school to pick up his younger brother and sister.  I take some more pictures as Jake drives to the schools and picks up the kids.  When we get to the middle school, my younger son, Cody, looks surprised to see two moms waiting for him in the car.  He begins to laugh at his older brother, but I quickly quiet him down by threatening to take away his new Playstation if he doesn't treat his older brother the same way he would treat me for the weekend.  My daughter, Maddie, has a much different reaction to Jake's new look.  She squeals with excitement and tells us how much fun it will be having an older sister.  I quickly remind her that it is just for the project and not to get too excited.  

 When we get home, I give Jake a list of my daily chores and guide him through doing the laundry and making dinner.  Jake is a willing student and follows each of my instructions without any complaint.  I have instructed the younger kids to pretend I am not there and to think of Jake as mom for the next three days.  Cody seems reluctant at first, but when I refuse to help him with his homework, he finally gives in and goes to Jake for help.  I can see Jake is a little stressed dealing with managing dinner and taking care of his younger siblings, but he doesn't complain and works through it.  I guess he inherited more from me than just my looks.  I take some more pictures of him throughout the evening to work into his project.  

 Soon it is time for dinner, and we all sit down to see how Jake's first meal has turned out.  He serves each of us some meatloaf, mashed potatoes, and vegetables with a dinner roll.  When he pours me a glass of wine, I tell him to pour a little for himself.  He seems a little surprised, but I remind him he is me for the weekend.  We begin to eat, and Jake soon finds himself facing one of my daily dilemmas.  My daughter Maddie is a very picky eater and refuses to eat her vegetables.  Looking at Jake, I expect him to get frustrated and angry, but surprisingly he handles the situation quite calmly.  After a few failed attempts, I see an idea come over his face.  He goes to the fridge and takes out a jar of applesauce.  He comes back to the table and mixes Maddie's vegetables with the apple sauce.  Maddie looks a little suspicious, but takes a bite.  Surprisingly, she seems to like it and even takes seconds.  Maybe Jake won't be the only one learning something this weekend.  

 After dinner, Jakes helps the kids with the rest of their homework and they watch a little TV before going to bed.  Standing in the doorway, I watch as Jake tucks Maddie in, reads her a story, and kisses her goodnight.  

"Good night mommy," Maddie says.

 I guess I've never noticed it before, but Jake makes a very good mother.  Sure he mostly follows my example, but throughout the night he has also incorporated some of his own ideas into his parenting style.  He has proven himself to be strong when it comes to discipline, but also fair and loving.  I watch as he says goodnight to Cody.  Cody seems hesitant, but as Jake leaves the room, Cody calls him mom.  I follow Jake to the living room to watch him collapse on the couch.  I say nothing since this weekend I am merely here to observe for the most part.  As such, he will be using my room for the next few days and I will be sleeping in his.  I want him to experience as much of my life as possible, and part of that includes my bedtime habits.  

 After watching a little TV, he goes to my room and changes for bed.  I step in and help him remove his makeup and give him a quick run through of my nightly routine.  He seems a little unsure how to use the toilet with his new prosthetic, and from outside the door I give him a few instructions.  He goes to bed in a tank top and a pair of boy short panties, my usual sleeping outfit.  I say goodnight after he sets his alarm and I go to his bedroom to get some sleep.  

 The next morning he is up bright and early and right back in the thick of motherhood.  He wakes up Cody and Maddie, then takes a shower, dresses in my office skirt and blouse, and I instruct him on doing his hair and makeup.  Once he is ready, he checks on his siblings and comes downstairs to make breakfast and lunches for the kids.  While the kids eat, I quickly get ready, and leave with them as Jake takes the kids to school and goes to work.  I have already informed the office where I work, that Jake will be coming in with me today and they readily agreed.  

 After dropping the kids off at school, Jake drives to the office and my boss leads him to my desk.  He and my co-workers guide him through my daily workload and soon he is tasked with answering phone calls and filing papers.  Everyone at the office seems pretty cool with what he is doing and they try to include him as part of the group.  He attends meetings and they take him out with them to lunch.  After a few hours, I can tell he is feeling uncomfortable in the heels he is wearing, but he sticks with it.  At the end of the day, we leave the office and everyone wishes him good luck on his project.  He is exhausted, but his day is not over yet.  

 We go home and pick up his brother and sister for soccer and dance class.  Since I work, they both take the bus home from school so they are all ready to leave the moment Jake and I walk in the door.  Jake drops Cody off at soccer practice then grabs a drink at Starbucks before we get to Maddie's dance class.  The drink gives him a little pick me up, and trust me he will need it.  While Maddie is in dance class, Jake and I sit with the other moms who tell him how sweet it is that he is doing all this for me.  Soon he is chatting like one of the girls and the moms are treating him just like they normally treat me.  Jake seems a little surprised at some of the topics the women are discussing, but he says nothing and goes along with it.  

 After dance class, we pick up Cody from soccer and the kids want pizza.  I can tell Jake just wants to go home, but he takes the kids out for pizza anyway.  Jake is nervous about being out in public dressed as a woman, but nobody picks him out as a boy.  In fact, I even notice a few guys checking him out, but I don't say anything since I don't want to make him feel uncomfortable.  While we wait for our pizza, the kids ask Jake for quarters for the arcade and Jakes fishes some change out of his purse.  

 A couple hours later, we finally return home and the kids are on a sugar high after all the soda they drank at dinner.  Jake takes off his heels and collapses on the couch while the kids run upstairs to their bedroom.  I look back at Jake and he is fast asleep.  I look at him and smile.  He has been so good through all this, but tomorrow he will get to see another side of my life that he doesn't know about.  During the week I am often stressed and tired, so on the weekends I take some time to myself to decompress.  

 The next morning I wake up Jake and tell him our plans for the day.  He goes upstairs to get ready, and soon we are on the way to yoga after the babysitter arrives.  Jake is wearing a pair of yoga pants and a crop bra top.  His hair is tied back in a ponytail and he is wearing a pair of my sneakers on his feet.  Surprisingly, we seem to wear the same size clothes and shoes.  When we get to the yoga class, my friends are waiting for us and they welcome Jake into the group.  The instructor goes slowly for Jake and it takes a few attempts for Jake to get the positions just right.  Luckily he is pretty flexible.  After the class, we take our showers (Jake in a private shower of course) and my friends and I take Jake to the spa.  Jake seems much more relaxed after a massage and a facial and a steam room session.

 Now relaxed, Jake is soon dressed in a dress and heels and finds himself spending a girls day at my friend Kirsten's house.  I let Jake have a few drinks and we spend the afternoon having lunch and talking.  I can tell Jake is feeling a little left out, especially when the subject of men come up.  I pull Jake aside and ask him something he might be a little uncomfortable with.

"Jake, I don't want to pressure you into anything," I begin, "but there is one aspect of my life I would like to share with you if you are willing.  It is entirely up to you, but I'd like to set up a double date for us with Zach and his son."

 Jake seems a little hesitant, but he eventually agrees to the idea.  I call my boyfriend Zach and explain the situation to him.  Zach had an 18 year old son, Ian, who is pretty good friends with Jake.  I wait as Zach talks to Ian, and soon it is all set up.  We say goodbye to my friends and head home to get ready for our date.  I instruct the babysitter to take the kids out to dinner, and the two of us spend the evening getting ready.  The guys will be taking us out someplace nice, so Jake puts on a black dress that ends just above the knee.  

 When Zach and Ian arrive, they hand us each a bouquet of flowers and take our arms as they lead us to their car.  Ian seems quite taken with Jake's beauty and the two of them sit uncomfortably in the back seat.  Ian is uncomfortable calling him Jake and I can tell Jake feels the same way.  Neither of them are very comfortable with the idea of being two boys out on a date together.  Zach and I decide to fix the situation and Jake and Ian agree to refer to Jake as Kayla for the evening.  Now that they are both thinking of Jake as a female, they seem a little more comfortable in the situation.  
 By the time we get to the restaurant, Ian is treating Kayla like a real girl.  He takes her hand as we walk in the restaurant and is a gentleman the entire evening.  Kayla seems a little nervous at the attention Ian is giving her, but she remains committed to her new role.  As I watch the two of them together, an idea pops into my mind.  Maddie is very young still and it will be some time before I get to do these kinds of things with her.  The weekend so far has been about Jake playing me, but I'd really like to spend tomorrow with Kayla as mother and daughter.  I excuse myself and ask Kayla to join me in the bathroom.

"Honey, I know this was just for your project," I say, "but seeing you tonight I would really like to spend a day with you as mother and daughter.  It's entirely up to you though.  I don't want to force you into anything."

"Sure mom," Kayla replies, "That actually might be kind of cool."

 We return to our dates and after dinner we go to the mall to buy Kayla a few things for tomorrow.  The past couple days she has been wearing my clothes for the project, but I don't want Kayla to look like a 38 year old woman, I want her to look like an 18 year old girl.  Kayla picks out a few outfits and shoes and tries them on.  She buys a pair of jeans, a skirt, some sleepwear, a couple tops, a dress, a swimsuit, and a few pairs of shoes.  We also buy a couple sets of underwear and a purse and makeup that are more her style.  The guys compliment Kayla on her style and they take us home.  We say our goodnights and Zach kisses me at the door.  Ian is more hesitant and gives Kayla a hug and a kiss on the cheek.  Before he leaves he asks Kayla to go out with him tomorrow and she agrees.  This time it will just be the two of them.  

 We go upstairs and put Kayla's new things into her room.  Since the project is over, she will be sleeping in her own room tonight.  We change into our pjs and spend the evening eating ice cream and watching a movie on the couch after Cody and Maddie go to bed.  Kayla is no longer in mom mode and I have instructed her siblings to treat her like their older sister for the rest of the weekend.  After the movie is over, the two of us go to bed.  

 The next morning, I am back in mom mode and resume my duties around the house.  Surprisingly, Kayla is more than willing to help.  She is quite convincing as a girl and I have to admit I am going to miss having her around the house.  I call the babysitter to take Cody and Maddie for the day and our mother daughter bonding begins.  We spend the afternoon doing each other's nails and giving each other makeovers then spend some time in our swimsuits in the backyard by the pool.  We stay in the shade so that she doesn't end up with any embarrassing tan lines.  Kayla looks quite lovely and very feminine in her new two-piece swimsuit and it appears her body is a lot more feminine than I had thought.  Her legs are quite long and her hips are a little wider and her waist is a little narrower than most boys her age.  As I look at the pretty girl next to me, it is hard to imagine that she is really my teenage son.  I decide to get into the spirit of the day and engage Kayla in a little girl talk.    

"So how has being a girl been so far?" I ask.

"It's OK," she replies, "I probably won't do this again, but being a girl is kind of fun."

"What do you mean?" I ask a little curious.

"I don't know," she responds, "I guess it's kind of cool getting to see things from the other side."

"Well, I'm glad you are enjoying yourself," I say, "How do you feel about your date with Ian?"

"A little weird," she answers.

"I can understand that," I say, "Do you think he's cute?"

"Mom, you know I don't like boys," Kayla whines.

"I know that honey," I continue, "Think of yourself as a girl though.  As a girl do you think he's cute?"

"I guess," she replies after giving it some thought.

 We continue talking and she relaxes a little on the subject of boys.  After some time by the pool, we go back inside and get changed.  I ask her to call her girlfriend to join us for the day.  She seems afraid of letting her girlfriend, Erin, see her as a girl, but eventually I convince her.  Soon Erin arrives with a couple other girls and to Kayla's surprise, they treat her just like one of the girls.  I take them out to lunch and we spend the afternoon walking around the mall.  We try on clothes and Kayla even begins to feel more comfortable when boys check her out.  The girls and I even get her to flirt a little and tell me which boys she thinks are cute.  Kayla seems shy about the situation, but Erin reminds her that she is a girl today and it doesn't make her gay to notice that other boys are good looking and that girls do it all the time with other girls.  At one point she becomes separated from the group.  A boy comes over and tries to talk to her and I wonder how she will handle the situation.  

"You seem sweet," she says gently, "but I have a boyfriend."

 I watch as she pulls out her phone and shows the boy a picture of her and Ian from the night before.  The guy seems to understand and walks away.  It looks like she can handle herself pretty well.  We spend a little more time at the mall then head home to get her ready for her date.  Since tonight is a regular date between teenagers, Erin and the others help her find something a little more casual than she did the night before.  She puts on a skirt and top and a pair of wedged heels.  The girls wish Kayla good luck on her date and head home.  Before long there is a knock at the door and Kayla nervously opens it.   

"Wow, you look great," Ian says when she opens the door for him.  

"Thank you," she says with a slight blush and a smile.

 She grabs her purse and the two of them head out for their date.  While the two of them are out on their date, I go and pick up my younger kids and take them out for tacos.  After dinner I bring the kids home and they are both in bed by the time I hear Ian's car pull up.  I go to the window and watch as Ian walks her to the door and gives her a goodnight kiss on the lips.  Ian drives off as Kayla enters the house in a daze.  

"How was your date?" I ask as Kayla comes and sits next to me on the couch.  

"I don't know," she replies, "It was OK I guess.  We saw a movie and had dinner at Chili's."

"That sounds nice," I say, "Did he kiss you?"

"Mom!" Kayla shouts in embarrassment.

"Don't worry," I say trying to comfort her, "There's nothing wrong with kissing a boy.  You were a girl tonight."

"Well," she replies after relaxing a little, "At the movies he put his arm around me and I rested my head on his shoulder.  At dinner we sat close together in the booth and sometimes he would accidentally touch my leg.  I pointed it out when he did and he would apologize.  I feel weird telling you this next part."

"It's OK, sweetie," I say, "I'm your mom."

"OK," she says hesitantly, "After dinner he parked the car at lookout point and told me how pretty I was.  Before I knew what was happening, he kissed me on the lips.  We didn't make out or anything, but he kissed me a couple more times.  Then he kissed me when he dropped me off at the door."

"Did you like kissing him?" I ask.

"Not really," she responds, but it wasn't as bad as I thought it was going to be.  Does this mean I'm gay?"

"I don't think so, honey," I reply trying to comfort her, "You were just playing the role of a girl."

 We talk a little longer then we go upstairs to change Kayla back into Jake.  Having worked at a salon when I was younger, I cut his hair and pretty soon Kayla is gone completely.  The next day Jake goes back to school and resumes his regular life.  During the week, we go through the photos and finish putting together the Powerpoint for his presentation.  Of course we only include the photos that are relevant to the project.  On Friday, he presents his project and he gets an A.  As expected, he is afraid how his classmates will take his dressing up as a woman, but surprisingly there seems to be no backlash.  A few guys even admit to him that they wished they had the courage to do what he did since their mothers are their real heroes too.  

 It's been several years since that weekend and life has resumed much as it did before.  Jake never dressed as a girl again after that day and going out with Ian didn't suddenly turn him gay.  That summer he graduated and left for college.  He visited when he could and after college he started law school.  He is now an attorney at a small firm downtown and is married with a 2 year old daughter.  His wife is also an attorney and they seem pretty happy together, despite both being very busy.  Jake is a great father and it's clear he learned a lot from the project.    

 A year after the project, Zach and I were married and Jake and Ian were both in the wedding party.  Things were awkward at first, but eventually things returned to normal between Jake and Ian.  Ian also moved away to college and got a job as an accountant.  He is also married, but he and his wife haven't had any kids yet.  

 When Jake and Ian moved out, life resumed at home.  Cody and Maddie both got along pretty well with Zach and quickly took to him as their step-dad.  Cody is now in college and it is just Maddie at home.  She is a junior in high school.  Now that she is older, we do mother daughter things together like I did that weekend with Kayla.  Of course, unlike Kayla, Maddie is definitely interested in boys and that presents a whole new set of problems.  

 The other day, I found myself going through some old files on my computer and happened across the photos from Jake's project.  As I look through the photos, I can't help but think to myself how proud I am of him.  How many boys would not only be willing to spend the day living the life of their mother, but also let their mother turn them into their daughter for a day.  Sure I may be his hero, but he is definitely mine.    
When Janet's 18 year old son is a assigned a photo project that involves him dressing as his personal hero, she is surprised when he selects her.  Soon her son is getting a firsthand look at her life when he becomes her for a weekend.  
Haegun Featured By Owner Mar 24, 2015
WOW!  I laughed and I cried.  This was so heartwarming, realistic, fun.  Well done.
rogerwilko Featured By Owner Jun 5, 2014
From one roger to another, good story! I didn't know U were on Fictionmania as well... I've checked that site out a few times, but never seen U... Have U ever heard of a related site called The Big Closet? One of my friends introduced me to it, & I like it quite a bit... 
MariaSki Featured By Owner Mar 26, 2014  Hobbyist General Artist
A well written and fun tale. I found it at Fictionmania. Nice to see it here.
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Submitted on
January 23, 2014


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