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Will You Be My Mommy?
🕑 Added 2023-01-20 12:45:01 +0000 UTCThis week's short story.
When Bob and Crystal went through their divorce, things were rough. There was a lot of animosity on both sides, and it got very messy as everything was fought over. But as often happens, Bob was able to afford a much better attorney, so when the judge handed down the final settlement, it was quite lopsided in his favor.
Crystal could live without the money or the house. But what really broke her heart, was that the judge ruled that Bob would be a better parent for their only child, her daughter Lindsay. Never mind that Bob was the one who started the breakup when he had an affair with his secretary at work. Still, he got custody of Lindsay. Crystal felt crushed at the news.
Now things got even nastier. Once, when Lindsay slept over at her mother's apartment, she returned fifteen minutes later than the agreed-upon time. A week later, Bob had a court order barring Crystal from keeping her daughter overnight anymore. In fact, their contact had to be 'supervised' by Bob now. It was a terrible insult to her, which caused a rage to build inside that she had never known before. She vowed to get even with Bob.
In the latest round of legal wrangling, one of the ploys that Bob had used to show what a 'good' parent he was, was to point out the fact that Lindsay's field hockey team was in danger of not being able to have a season because the assistant coach had to quit. Bob had stepped in by volunteering to coach, saving his daughter's team.
This impressed the judge, showing how devoted he was to his daughter.
"If the mother cares about her so much, why isn't she volunteering to coach?" the lawyer had said. He failed to mention that Crystal was working two jobs just to make ends meet, and there was no time to volunteer as a coach. But the ploy had worked.
And so now, Bob was the assistant coach of his daughter's field hockey team. The head coach was Natalie, and she was unhappy when she found out that Bob would be joining her.
"This is a girl's team, in one of the few sports where there are no boy's teams" she had argued to the athletic director. "We need a female role model for the team. Not a man."
"I'm sorry" replied the A.D. "But we have no choice. We don't have the budget to hire someone, and he is the only volunteer we were able to find."
Natalie was steamed. She was being forced to take on a man as the assistant coach.
It was the day before the first match. The practice was just wrapping up, with the girls running two laps of the field. Bob watched proudly as Lindsay finished in the pack out in front of the other girls. She had always been very athletic.
"Tomorrow is our first match," said Natalie.
"Yes, I know. I can't wait" said Bob.
"Do you know about the uniform rule?" she asked.
"The girls all have to be in uniform to play. Of course."
"But so do the coaches," said Natalie.
"Really?" said Bob. "I wasn't issued a uniform."
"You're getting one now. I've got it in the car."
"Very good," he said.
Bob walked with Natalie to the car. Hanging in the back was a uniform, like the girls wore, with an athletic shirt, and a green kilt. She reached in, took the hanger off the hook, and handed it to Bob.
"What's this?" he said.
"Your coach's uniform" she replied.
"But this is a player's uniform."
"The school board decided that the players will relate better to the coaches if we are in the same uniform that they are. So this is the coaching outfit for our district. I've got one just like this, and I have to wear it too."
Bob was filled with doubt. How could he wear a girl's uniform, with a kilt?
"Oh, and as you know, the regulations say that sports bras are required. You'll need to go out and buy one for yourself. If you're out of uniform, you will be sent home. Sorry, but that's the rule. And a rule is a rule."
"I understand," said Bob, who was steaming mad.
What a terrible choice! He would either need to embarrass himself by showing up to the game wearing a field hockey uniform, including a sports bra, or else he'd have to quit. Then Crystal would have ammunition to get Lindsay back. He couldn't allow that. He was going to have to swallow his pride and wear the kilt.
That night, after Lindsay went to bed, he went out to a local store that was open until midnight. With much trepidation, he went into the women's athletic department and bought a sports bra for himself.
The next day, after work, Bob drove to the school. He went into the coach's room, and then into the private restroom inside. He took off his suit and tie, stripping down to his boxers. He put on the sports bra, the shirt, and the green kilt. He felt like an idiot.
Then he put on white socks like the girls wore, and athletic shoes in the same color as theirs. Now he was in uniform. He hung his clothes up in a locker, picked up his clipboard, and went out onto the field.
As Bob stood there discussing the lineup and the strategy with Natalie, he felt completely embarrassed. A grown man in a kilt. Nobody could see the sports bra (other than Natalie, who asked to see that he had one on), but that felt equally embarrassing.
The game started, and soon he forgot his troubles, as he focused on the athletic event. It was a close game up until the end when Lindsay scored to put her team ahead for good. When it was all over, he congratulated her on her fine performance.
"Dad!" said Lindsay, "You're embarrassing me!"
"How?" he said.
"Those hairy legs of yours. You look ridiculous in your kilt with hairy legs.
Bob was desperate to keep Lindsay's approval. So that night, after they went home, he took his razor into the shower and shaved his legs. He didn't want to embarrass her again. He needed her to like him.
He didn't want Crystal to gain any leverage, so she could get Lindsay back.
Two days later was the next match, and Bob was in a panic. As he dressed up in the team outfit for the match, exposing his now-hairless legs, he could not find the sports bra. He was sure that he had packed it away in his bag, but it just was not there now.
"Your legs look nice," said Natalie. "Do you have your bra on?"
"Um, I have a problem there. I seem to have lost it."
After much ranting and raving, Natalie shook her head and went to her locker room. She returned with a bra in hand.
"This is an old one of mine. Try not to lose this one."
Bob nodded and went to put it on. He did not like that woman, Natalie. It was kind of sickening to think that he was putting on a bra that supported her boobs. She was kind of dumpy, and a little too heavy. Not what he liked in a woman at all.
The bra she gave him was white. It had a lot of padding, and a pretty frilly lace trim along the edge. The cups had a lacy pattern as well. Bob was alarmed that when he put his shirt on, you could kind of see the lace pattern in the cups through the top. He was too focused on that to notice that the padding of the bra made it look like he had small boobs too.
He paced the sidelines with Natalie as play started against the school's arch-rival, Midville. This time, they weren't so lucky, they lost a close match, although they always seemed to have a chance to win it.
"Don't worry" said Bob. "We play them again, the last game of the season. We'll get them when they come to our house."
Natalie looked at him disapprovingly.
"Do you girls know why we lost?" she said.
There was silence
"We lost because we did not play as a team. If we are to win, it will be as a team, not as individuals. I don't care how good any single one of you is; it is only the team that matters. We will have a team meeting on Saturday, to do some team bonding. We need to be a team if we are to win."
All of the girls applauded. Bob joined in too. He had no idea what he was in for.
On Friday, Natalie told all of the girls that as a team togetherness thing, they would all wear similar clothes to the meeting at her house on Saturday.
"We will wear skirts and tank tops," she said. "See you at six."
Bob went to walk away when Natalie tapped him on the shoulder.
"That includes you too, coach. I expect you there to bond with your girls. Don't disappoint me."
It wasn't a threat, but then again, it was. He was going to have to show up, with a house full of girls, wearing a skirt and a tank top. Bob considered quitting right then and there, on the spot.
"Don't worry" said Lindsay. "We'll go shopping tonight, and I'll help you pick out something."
And so, Bob found himself at a fancy department store, in the women's department, with Lindsay helping him to pick out a skirt. She found one that was white and pink, with a cute print pattern. It would come down to just below his knees. For a tank top, she found one that was a light blue color, which she assured him looked cool with the skirt. It included a built-in bra.
He went home and tried it on.
"Let's see dad!" said Lindsay, excitedly.
Bob came out, blushing.
"Oh no. Your chest hair looks all icky. And you need to shave your armpits too. That hair is gross."
And so, Bob hit the showers again, armed with his razor. Once he was hairless, he put the outfit on again for Lindsay.
"Hang on a minute dad," she said. "I'll be right back."
Bob waited, wondering what she was going to do. When she returned, she was holding a pair of panties, and a pair of pantyhose.
"Your legs will look a lot better in nylons," she said. "They're too rough. And you can't wear boxers under a skirt like that! So here are some old panties for you. Go ahead, try them on."
Bob was hesitant to do it, but he sighed. It was for Lindsay. So he did it. He returned to the living room to show her. Lindsay lit up and ran over to give him a hug.
"I like it when you're dressed like that," she said. "It makes me really like you. We can do so much together now. I loved shopping with you. Today was so fun."
Bob didn't realize just how much she craved a female parent.
The next day, at 4:00, Lindsay said they needed to start getting ready to go out to meet the team.
"It's two hours away honey. We've got plenty of time."
"No, we don't. You had better start getting dressed."
"Okay" sighed Bob.
He went to his room, put on his panties, pulled on his pantyhose put on his skirt and his tank top. There. Five minutes. Now, what would he do for the next hour and fifty-five minutes? He went to the living room to wait for Lindsay.
"Come on in here" she called out from her room.
"Is it okay for me to come in?" he asked.
A father doesn't just want to walk into a teenage daughter's room.
"Of course it is," she said.
Bob was shocked to see her in her skirt, but with only a bra on top. He looked away.
"It's okay," she said. "You're in a skirt too."
Bob thought about how she didn't need to remind him. He frowned. Maybe this was a bad idea. But Lindsay really warmed up to him when he was in a skirt. When he was dressed as a man, she was often cool or distant. But whether it was the kilt at the games, or now the skirt at home, she treated him very differently. She didn't act like she didn't want to be there. It was important that she like him, in case Crystal appealed in court, which she surely would at some point.
Lindsay put her top on, and Bob felt very relieved. Now she told him to sit down at her vanity.
"What for?" he asked.
"You need some makeup" she replied. "If you're going out dressed like that, you need your face done."
"No I don't," said Bob.
"All of the other girls will. You don't want to embarrass me in front of everyone, do you?"
"No," said Bob, defeated. She had just shamed him into wearing makeup.
He just sat there as she put all sorts of powders and creams on his face. She did up his eyes, his lashes, his lips, and his face. She also gave him a necklace to wear, and a pair of her old clip-on earrings. As she worked on him Bob caught sight of a tattoo on her arm
"Just when did you get a tattoo, young lady?" he said sternly. "You didn't have my permission to do that!"
"Chill out dad, it's not a tattoo," she said. "It's henna. It will wish right off. Here, let me give you one too. All of us on the team are wearing one."
She took out the henna tattoo and applied it to his arm. When she removed the backing, it looked like a real tattoo of a winged horse with a long mane. Bob felt ridiculous in his getup. He watched as Lindsay did her own face. Then she went to her closet, returning with two pairs of shoes.
"I went shopping today, at a secondhand store," she said. "I think these will fit you."
She handed him a pair of women's shoes. They were pink, with an open toe, and a two-inch heel. Lindsay had a similar pair for herself, but the heel was higher. Bob put them on and teetered a bit as he stood up in heels for the first time.
Lindsay laughed at him and spent the next fifteen minutes making him practice how to walk in heels.
Suddenly, it was just twenty to six. Bob realized they had to go now, or they would be late. He walked to the minivan and got in. He had some difficulty at first with the pedals, being in heels. That would take some adjusting to! He backed out of the driveway, praying that none of the neighbors would notice him wearing full makeup and earrings.
Fifteen minutes later, they arrived at Natalie's house. Bob and Lindsay got out of the car and walked in the front door. The house was already filled with girls, all of whom had on skirts and tank tops too. None of them made fun of Bob. In fact, they all treated him nicely.
"Hey coach," said Sally.
"I like your shoes, coach," said Tina. "I've been wanting a pair just like them. I didn't realize you knew so much about fashion."
"I had help," said Bob, pointing to Lindsay.
After everyone talked for some time, Natalie called the team meeting to order. The girls all sat on the couches, the chairs, or on the floor. Natalie and Bob stood in the front.
"Everyone's name is in a hat here," she said, holding up a cardboard box. "I'm going to pull out one, and coach Bobbie will pull out one."
Bobby? She had always called him 'Bob' before. Oh well. He reached in and pulled out a slip of paper.
"Janice," said Natalie.
"Tina," said, Bob.
"You two are partners. Go stand together in the corner."
The coaches pulled the next slips of paper.
"Abigail," said Natalie.
"Bobbie" read Bob. He didn't know any girls named Bobbie on the team. He looked up at Natalie.
"I thought you'd fit in better if your name was a little softer" she whispered into his ear.
Then she addressed the girls.
"Abigail, you and coach Bobbie are partners."
First, they did some of the standard trust exercises that Bob had seen in coaching books. Fold your arms over your chest, and let yourself fall. You have to trust your partner to catch you. Then she falls, and you catch her. Then they played some games, where it didn't matter how well an individual did; you won or last as a team.
After a milk and cookie break, they were supposed to do the next exercise. Natalie led everyone to the kitchen.
"Whoa," said one of the girls, as she caught sight of what looked like a hundred different colors of nail polish.
"We need to pick out a color as a team," said Natalie. "Then everyone will paint her partner's nails."
"Yeah!" said all of the girls, clapping.
It took a little while, and some debate, before the team reached a consensus on one single color. In the end, they chose the same red as the school colors, to match their uniforms. Natalie had an idea that it might end up that way, so she was prepared with a dozen bottles of nail polish in that color. One by one, the girls painted each other's nails.
Bob sat there, letting Abigail put the bright red color into his nails. He wondered how hard it would be to take off later.
"We should all wear our nails like this to the games," said one girl.
There was a swelling of cheers, as everyone got excited about the idea. Bob frowned. How would he be able to get off from work, get dressed, and do his nails before every game? There just wasn't time.
As one last show of teamwork, the girls decided that they would French-braid each other's hair. Only there was a problem. Bob's hair was too short.
"Bobbie, may I suggest that you get a wig, and let Lindsay braid it" whispered Natalie. "You wouldn't want to be the only one on the team without French braids, would you?"
"No" whispered Bob in reply.
Great. Now he needed a wig.
On the car ride home, he asked Lindsay.
"Honey, do you think that I should get a wig, so you can French braid my hair for the next game?"
"Awesome!" said Lindsay. "Hey, that wig store on Main Street is still open. Let's get one now."
"You want me to go into a store like this?" said Bob.
"It's late. There won't be many people in there. Come on, this will be fun."
He was defeated. He couldn't argue with her. Better to do it now, on a Saturday when it was almost empty than to be seen going into the wig store during a busy day. He and Lindsay went in, and she immediately found a wig of long, auburn hair, which she insisted was perfect for him.
She made him try it on, and wear it home.
When they got back home, Bob was exhausted, and his feet hurt from the heels. He was really glad to get back into the safety of the house, where nobody would see him dressed up like that. He went upstairs with Lindsay, who was acting giddy, like a little girl.
"Will you tuck me in?" she said.
"Sure," said Bob.
She tore off her top and her skirt right in front of him, which caused him to look aside. He heard her jump into the bed. She was wearing an oversized T-shirt as a nightie.
"Will you read me a story, mommy?" she said.
Bob was in shock. Mommy? Him?
"Over there, on the table. Please!!!!!"
"All right," said Bob.
He picked up her favorite book that he and Crystal had read to her when she was just a little girl. He read it to her, and her face became calm and happy. Soon, her eyes closed. Bob turned off the light, and left her room, as she drifted off to a happy sleep.
Bob solved the nail problem, at Lindsay's suggestion. He bought some fake "press on" nails. He could go to work with plain nails, with no polish. Then in just a few minutes, he could have long nails, which were painted a bright red color. So now, he paced the sidelines in his wig, which was French-braided, just like the girls, along with long red nails. By now, he was used to coaching in the skirt. It no longer felt strange to him. It was just part of the routine.
Two weeks later, on Saturday, it was Lindsay's birthday. Bob asked her what she wanted to do for her birthday, and she had a special request for him.
"You know I miss mom," she said.
"I know," he said.
"I know I can't see her anymore because she was very bad," said Lindsay. "I love you, and I love being with you, but I miss having a mom."
He nodded, understandingly.
"I told you how much I liked it when you were dressed up for me. It was like having a mommy again, but one that loved me, and cared about me."
As she hugged him, Bob swelled with pride. This was exactly how he wanted her to feel: dislike for her mom, and love for only him. It was working out very well. Crystal would never have her daughter back. Never.
"For my birthday, will you do something special for me?' she asked.
"Sure my little pumpkin. Anything you want."
"I loved it that night with all of the girls when you were one of us. Will you be my mommy again, for today?"
She was asking him to dress up as a woman again. It was a hard thing to be asked, but what the heck. He kind of dressed up like a woman twice a week for the field hockey matches.
"If that's what you want," he said.
"You're the best mom in the world!" said Lindsay.
She excitedly led Bob up to her room. There, she began dressing him up. This time though, after she had him put on a bra, she had a surprise: a pair of fake boobs that were glued onto your chest, making it look like you were stacked. Bob put them in place, and couldn't stop staring at his chest, which now poked out in front of him.
Lindsay had bought a yellow house dress at a new set of heels at the secondhand store, which he now put on. But she wasn't happy.
"You need something else," she said.
She went to her closet and returned with a girdle.
"Take your dress off, and put this on," she said.
Bob did as she asked, and he felt really funny in the girdle. It really constrained him. It seemed to flatten his tummy, and the padding in the hips and the butt seemed to give him curves. So when he put the dress on again, he looked a lot more feminine than he ever had. Along with the big bulges on his bosom, and the long hair from the wig, he was really starting to look feminine.
He put on his nails, while Lindsay did his makeup. She asked him to put on the necklace and earrings again, but this time she also had a ring for his finger and a bracelet.
"I love you so much mommy," said Lindsay. "You're the best mommy in the world! I love you more than anything."
Bob felt so happy that she felt that kind of love for him. It was music to his ears.
They went downstairs, and Lindsay suggested that they bake a cake together. Bob was stirring the batter when there was a knock on the door.
"I'll get it," said Lindsay.
A minute later, she returned with two other girls that Bob had never met before.
"Mom, this is Kate and Cindy," said Lindsay. "And guys, this is my mom."
"Hi Mrs. Davis," said Kate.
Mrs. Davis? That was Crystal. He was Mr. Davis. It felt terrible to be addressed as his own wife!
Bob played along as if he was her mother. He continued to bake the cake, while the girls ran up to Lindsay's room. He got out milk and cookies for them and set them up on the table.
"Girls, snack time!" he called out.
They all came downstairs and talked as they ate their milk and cookies. Bob took the cake out of the oven and put it on the cooling rack.
"She let me lick the batter," said Lindsay to her friends.
Bob didn't like being referred to as 'she'!
The girls all talked and talked about everything. And they wanted to include 'Mrs. Davis' in their conversations. After the cake cooled, they decorated it together (Lindsay got to lick the last of the icing). They were sitting around the living room, eating the birthday cake when there was an unexpected knock at the door. Lindsay was using the bathroom, so Bob instinctively went to get the door.
It was only when he was opening the door, that he realized how he was dressed. He had become so relaxed that he wasn't thinking anymore about the fact that he was dressed up as a woman. He was very shocked when the person outside the door was none other than Crystal herself!
"Hello Bob," she said, as she looked him up and down, "Or is it 'Bobbie' now?"
NO! Of all the worst things that could happen, this was it. His ex-wife finds him dressed up as a woman, pretending to be Lindsay's mother. Now her real mother was here, and Bob knew he was in deep trouble.
"Hi girls," said Crystal. "Why don't you go up to Lindsay's room? I need to talk to her mother."
Bob swallowed hard. He had been caught. Now, what was she going to do? Crystal walked in, and touched her cheek to his, making a kissing sound. Then she moved her head, so they were touching the other cheek.
"You know," she said, "I didn't believe it when I first heard that you were a pre-op transsexual and that you were well along in your transition into womanhood. But I've seen the pictures, and now that I've seen you with my own eyes, I know that it's true."
Bob wanted to tell her that it wasn't true, he wasn't turning himself into a woman. But if he did that, then Crystal would have wonderful grounds to take Lindsay from him. What kind of environment is it to raise a girl, where the father goes around dressed up in women's clothes? She had him trapped. Either he had to tell her he was transitioning to womanhood, or he'd lose Lindsay.
Crystal reached into her purse and pulled out two bottles of pills.
"You remember how the doctor put me on hormones after they had to remove my ovaries because of the cysts?" said Crystal. "Well, my hot flashes stopped, so I'm not taking them anymore. Since you're becoming a woman, you'll be needing these now."
She handed him the bottles of female hormones.
"Even though I see you looking all pretty in a dress, I still have doubts about your intentions," she said. "I want to see you take some of those pills now. If you really are becoming a woman, then having a few more female hormones in your bloodstream won't be bad at all. But if you're a man hiding behind a facade, well then, you know how female hormones will start to feminize you. They'll make you lose your ability to get it up. You'll grow boobs. And a lot of other things. Show me that you're really becoming a woman. Take some of those for me.
Bob was trapped. What a terrible choice! Lose Lindsay and be totally humiliated by his ex-wife. Or take his first dose of female hormones, which would start to alter his body and his mind. He really would become a woman. With a shaking hand, he took three of the white oval pills from the bottle and gulped them down with water.
Just then, there was a knock at the door. Bob went to see who it was now. It was Natalie.
"Oh hi Bobbie," she said, greeting him with the cheek-kissing thing as if he was a close female friend.
"Hi, Natalie" he replied.
"Crystal!" she said, her voice raised in excitement. She ran over and embraced her old friend.
"You two know each other?" said Bob.
"Yes, Bobbie" replied Natalie. "Since college. She was the one who came up with the initial idea and the plan to turn you into a woman."
"And Natalie is the one that told me to show up to the game, so I could take this photo of you dressed in a kilt. Is that a bra strap showing? And I love your long hair and nails in the pictures. You're quite cute as a woman Bobbie."
Bob looked at the photo. He didn't know she had been sitting in the stands photographing him!
"And here are some photos from the girl's party at Natalie's house. You look darling in your skirt."
Bob's mouth was dry.
"And here are some photos from today," she said.
"How did you get those?"
"Lindsay was so proud of you, she took them with her cell phone, and emailed them to me. I had them printed up right away before I put them on my website."
"On your website?"
"Yes. I've been tracking your progress from manhood to womanhood. And I've got it all posted on the net. The girls at work all check in every day to see the latest development. They can't wait until you're fully female."
Bob felt like crying. An hour ago, he was so happy with his life. He had his daughter who loved him now, he had screwed his ex-wife in the divorce, and everything was fine. But now, he realized that his ex-wife had manipulated him all along. She was turning him into a woman, and he hadn't even realized it.
Now he was wearing a dress. And makeup. And had female hormones absorbed into his bloodstream. Lindsay was calling him "mommy", and introducing him that way to her friends. What a terrible moment for a man to realize that he is being turned into a woman, without even fully realizing it.
"Mommy!" said Lindsay. "Mom, I mean Crystal, says that you're letting her move back in, so I can have both of my moms. I'm so happy that we'll have all three of us girls here together."
She gave him a hug. How could he say no to his darling little girl?
Natalie and Crystal said their goodbye in the driveway.
"You were right Crystal. Men are so easy to manipulate. You set it all up, and he's fallen into your trap. Now he'll be a woman. Like us."
Crystal gave her an evil grin.
"Wait until we set him up with a man. Now that will be fun to see."
"I can't wait. I can't wait."
