Short Story: Don't Tell Mom the Babysitter Feminizes

Here's a new short story for everyone. Merry Christmas!

Don’t Tell Mom the Babysitter Feminizes!

Written by Courtney Captisa

Edited by Sally Bend

“It’s so nice to meet you!” smiled Jessica, the skinny 18-year-old brunette girl at the door of the McLandon household.

“Please come in!” said Ms. McLandon, waving Jessica, who was carrying a large backpack, in from the front door. “My sister has told me very good things about you,” she added, referring to Jessica’s babysitting skills. Jessica had been working for her sister for over a month now, babysitting her 9-year-old and 3-year-old, and was the first person she recommended to her sister when discussing a much-needed date night.

Dating as a single mom in her late-30s was becoming increasingly difficult.

“Oh, wow, your house is so pretty!” Jessica was smiling as she looked around at the contemporary artwork and large mirrors in the hallway leading to the living room.

“Thank you,” said Ms. McLandon. “Please excuse the mess in some parts of the house. It has been so hectic lately - at work and around here.” She raised her arms up for expression.

“Don’t worry. I’ll clean up while I’m here, after the kids are in bed,” said Jessica.

Ms. McLandon smiled, realizing that Jessica was an angel sent from God already. “Please, make yourself at home. You can put your stuff down there,” she said signaling to a sofa in the living room. “Let me give you a tour of the house,” she said excitedly. 

She first showed Jessica the living room and kitchen while making small talk, mostly about Jessica’s life as a college freshman at the local state university, and how she originally found her sister through a recommendation from a mutual friend at church. Ms. McLandon went on to tell Jessica about her two children, Casey and Andrew, and some of their habits and responsibilities throughout the night. While in the kitchen, Ms. McLandon’s 10-year-old daughter came in the room, excited to meet Jessica since it was cool to her to hang around an older female, but not as old as her mom or her friends.

“And you must be Casey!” said Jessica smiling wide and bending forward with her hands on her knees.

“Yah!” said Casey, who was wearing a green shirt with a cartoon character on it, and had her dirty blonde hair in a side ponytail.

Their feminine emotions kicked in hard as both extended each other’s arms for a hug. After their short embrace, Casey backed up, smiling, and jumped up and down. “Mom said you are on the soccer team!!!” 

“Yeah! I’ve been playing since I was this high,” said Jessica, making a hand motion from the ground. “You play too?!?!”

“Totes! Can we play outside?!” she responded.

“Maybe sometime when it’s light outside,” said her mom, smiling.

“Don’t worry. We are going to have a lot of fun indoors tonight. Plus… you know it’s a little chilly,” Jessica said rubbing her arms against her pink fleece hoodie.

“Okay!” said Casey jumping up and down again.

“She’s the energetic one,” said Mrs. McLandon. 

“Where is Andrew?” asked Jessica, still smiling excitedly to meet her son.

Ms. McLandon rolled her eyes slightly. “Probably in his room playing video games.”

“I can’t wait to meet him!” said Jessica.

Ms. McLandon crossed her arms. “He stays in his room for the most part. You know boys that age. He has been complaining that he doesn’t need a babysitter.” She then walked closer to the foyer that led to upstairs. “Andrew! Come down and meet Jessica.”

Andrew could hear his mom from his bedroom but ignored her.

“Andrew... Please come down. She’s excited to meet you!”

“Just a minute!” he screamed in hopes that if he came down, she would get off his back and hopefully Jessica wouldn’t bother him the rest of the night. He frantically threw off the black heels he was wearing and pulled down the nylons. Standing up, he took off his mom’s mixed lace, flair-sleeve shift dress, followed by the black 36D black bra that was obviously too big for him that he had found. Although he didn’t want to take off the panties that felt so comfortable down there, he threw them under the bed with the other clothes and quickly threw on some boy clothes to hurry downstairs.

When he saw Jessica, he couldn’t speak. When his Mom mentioned a babysitter a few days ago, he imagined some overweight woman in her late-20s, like the last woman who came over. But, instead, here was this petite college-age woman with girl-next-door looks. Her breasts were not large, but they fit her figure. She looked like the type who would be captain of his high school varsity cheerleading squad.

“Hi! I’m Jessica!” she said with a cute smile, and a little wave, knowing he probably wouldn’t come running up hugging her like his sister did. He wanted to touch her, but a hug wasn’t what he had in mind.

“Hey…” he said.

This girl was no more than four or five years older than him. And SHE was his babysitter?! Part of him felt like he had lucked out getting a babysitter who looked like this, but another part of him felt embarrassed that a girl only a few years older than him was now in charge of him.

Jessica displayed her artful skills of smart talk. “Do you have Super Crush Brothers XII? I challenge you later on!” she said playfully, pointing at him for the video game death match.

“You play video games?”

“Yeah! Love them!” she said. “What were you just playing in your room?”

Andrew didn’t want to say, ‘Pretend like I’m a sissy girl,’ and instead lied, “Battlefield Evil Corps.” 

“Ah, I think my brother plays that on Live,” she responded.

He smiled knowing that there was a new type of connection, although he couldn’t see himself playing with her in reality, and imagined that she would be busy entertaining his little sister by doing their nails or something.

Ms. McLandon looked at the time on her iPhone. It was 7:40 and she needed to start driving to meet the date she had by 8 at an Italian restaurant in town. “I need to get going. Jessica, if you need anything, don’t hesitate to text me. Andrew, Casey… please be on your BEST behavior for Miss Jessica.”

“Yes Mom…” Andrew said hurrying back to his room.

Casey came up and grabbed Jessica’s arm. “Jessica! Want to see my room?!”

“Sure Casey!” said Jessica in an authentic excited tone.

Ms. McLandon smiled, “Bye. Love you both!”

Casey took Jessica upstairs to show her the new artwork she had in her room while Andrew had managed to get upstairs before them, and lock his door shut to immediately jump in his bed. Jessica looked amazing, but confused emotions hit his mind. He was attracted to her due to her striking looks, but part of him wanted to LOOK like her. He wanted her figure. Her long hair. Her pink nail polish. To wear the dark denim jeans with long white blouse, pink hoodie, and jewelry she had on. To smell like her, the rose-like nature that she armored. Andrew closed his eyes and imagined various things as he sank down into a world of pleasure.

_____

“Thank you so much!” Jessica said at the end of the night, receiving $100 cash from Ms. McLandon.

“Oh, no, thank you! You did everything I asked of you and more! Are you available next Friday?” she asked, since the date went well, and she had set something up with the same man.

“Yes! Same time?” 

“I will let you know. It may be about an hour earlier.”

“That’s no problem at all, Ms. McLandon.”

“Please, call me Stacy,” she responded with a smile. 

“Okay Stacy. Bye bye!” said Jessica as she excitedly left the house. Both women were so excited about the new opportunity that neither noticed that Jessica had left without her pink hoodie. The temperature had not gone down much, so Jessica didn’t notice when she left.

Halfway down the road, she noticed she had forgotten something.

“Crap. I left my hoodie!”

_____

The next Friday, Jessica returned to the McLandon household. She was greeted at the door once again by Stacy, although this time, she was showing more cleavage in her blue dress than last week. 

“Hi!” said Stacy. 

“Hey! Thanks for having me back!” Jessica said as she entered on Stacy’s cue.

“Jessica!” screamed Casey, running up to her, wasting no time greeting her new favorite babysitter.

“Hey Casey! Did you check out that movie I told you about?”

“Yeah!” screamed Casey. “It was soooooo funny!”

“I knew you would love Amy’s Princess Vacation!”

After some short banter between the three girls, Stacy gave Jessica instructions for the night and went on her way. She didn’t see Andrew at all, who was staying in his room, debating on whether to engage with Jessica more or not. Part of doing so made him extremely nervous, so he didn’t even bother coming down to say hi. Meanwhile, Jessica spent time entertaining Casey, doing some crafts and playing games before making sure she brushed her teeth before bed. Jessica knew that Ms. McLandon wasn’t going to be home until a little after midnight this time, and around 9:30, once Casey was asleep, she knocked on Andrew’s door.

*Knock *knock.

“Who is it?” asked Andrew, who really was playing a video game.

“It’s Jessica!” she responded in an almost cartoonish hyper voice.

“What do you want…?” Andrew asked in his nervous, yet boyish tone.

“Open up… I have something exciting for you!”

What the hell could that be? He thought. Was this a game? 

“What is it…?”

“Open up! It can’t wait forever!” she said in an excited tone of voice.

He finally gave in to temptation and paused the game to unlock the door. Once getting a look at her, he had the same crush-like-hit come to his body. Her hair was not in a braid like it was last week. This time, it was flowing down, and she had more makeup on, especially her eyes. Her pink blouse showed off her girly arms and B-cup breasts, while she appeared to have on yoga pants this week, and he couldn’t help but wonder what her ass looked like.

There were no words that came out of his mouth. He waited for her to make the first move.

“Let’s make this quick!” she said, barging into his room.

“What?!” he asked shocked by her statement.

“Your mom told me an interesting story tonight.”

“WHAT?!” he asked even more nervously.

“That you spend a lot of time in here, and that it is your private liar, but that we need to play a game in here.”

“You want to play me in video games now?”

“We can later, but first we need to play a game on how fast we can get this room clean!”

“That wasn’t what I was expecting…”

Jessica laughed, “Yeah I know it’s not the most fun task, but with the both of us, I think we can have everything to her liking here in about thirty minutes or so.”

“Umm... Jessica… can this wait a few minutes?” he asked knowing he had things to hide.

“I wish! I don’t like cleaning either, but you know it’s so important in life. Let’s just work together as a team. How about you take those dirty dishes down, then start cleaning around the dresser, and I’ll take care of where things are probably most dirty, like around the floor. Have to get all of this stuff clean before I vacuum,” she said before bending down and starting to pick up some clothes of his that were on the floor. 

“Jessica… I don’t want to do this now!” he begged.

“It’s not that hard, Andrew. If you keep this place clean, we won’t have to spend as much time on it in the future. Ready, set, go!” she said quickly picking up clothes and throwing them in the nearest hamper.

Suddenly, Jessica spotted a familiar garment underneath some clothes. “Oh my gosh, there’s my hoodie. How did it end up here?” she asked curiously.

Andrew played dumbstruck. “Maybe mom put it in here by accident.”

“Do you have a girlfriend?” she asked sincerely.

“Kinda…” he lied once again.

“That’s sweet! What is her name?” Jessica asked while picking up stuff.

“Melody…” he said standing still.

“Cool! Let’s keep on cleaning. Come on. Catch up!” she yelled as he stood there, shocked, as she reached under his bed.

Suddenly, Jessica’s enthusiasm came to an immediate halt and Andrew’s face turned bright red. He felt his penis shrivel at humiliation.

She placed her hand on the dress and pulled it out from under the bed. Jessica noticed that it was the same dress that Stacy had worn on her date last week.

“Why is your mom’s dress under your bed?”

He didn’t answer her, knowing that his cover had just been blown.

Jessica continued digging her hands under the bed, carefully pulling out a pair of pink panties with a matching bra. “Andrew… What is all of this stuff…?” She could tell he was very nervous.

“I don’t know how it got there…” he said in hopes that she would throw them in the hamper with the rest of the clothes and forget about it.

Unfortunately for Andrew, Jessica wasn’t stupid. “This was the dress your mom wore… and I’m assuming her bra and panties, based on the size. I don’t think a girl your age could fit in this stuff…”

Andrew became even more nervous. His palms were sweating. He said nothing.

She was puzzled. Her hoodie was in here. His mom’s clothes were in here. What teenage boy accidentally has his mom’s clothes in his room? Something wasn’t adding up. Equally nervous, she asked him. “… Are you wearing this stuff?”

“NO!” Andrew shouted.

“Quiet. Your sister is sleeping! It’s okay… you can tell me…” she said still nervous. It was the first time in her eighteen years on Earth that she had to deal with something like this.

His relationship with Jessica had been a short one. Just one night of babysitting. Why in the hell would he openly admit his crossdressing habits with her, when it had been such a deep secret for two years? It wasn’t like he had easy access to female clothes. There was no girlfriend. No close female friends at his age. His only options would be to sneak into Mom’s room or attempt to try on Casey’s stuff, which wouldn’t fit him, since she was just over four-feet-tall.

“Andrew… I want you to be honest with me…” Jessica, said growing more concerned.

He knew he had nowhere to hide. While lies were a part of his regular vocabulary, how much could he do with this very sweet, very pretty girl in his bedroom? It was a part of his wet dreams.

“Fine… Yeah… I like wearing girl’s clothes. Are you happy?!” he said, getting angry.

She was silent for a second. While she didn’t know him too well, she could tell he was emotional about it. She thought about the men in her life, and how none would probably admit to wearing their mom’s panties like he just did. Jessica thought about the best way to handle the situation.

Jessica pushed him down lightly to sit at the edge of the bed with her, and started calming him. “Thank you for admitting that to me. You are very brave! What makes you want to dress like a girl?”

He was flabbergasted, surprised that she wasn’t getting angry that he had earlier jerked off while pretending to be her, wearing her pink hoodie. Then again, she didn’t know about the jerking off part.

“I don’t know…” he said honestly, almost in tears. “I’m confused.”

“Do you want to be a girl?” she asked.

“In some ways… I like being a boy don’t get me wrong… but… the clothes…. the makeup… doing sissy things…”

She continued to rub his shoulders, still confused about his gender identity. “How often do you do this?”

“As much as I can.” he admitted. “It’s hard to do so when my mom is home, though.”

Jessica was still awestruck by the conversation, but thought it was important to keep the connection with him, as part of her responsibility - though other parts of her job description called for other areas of responsibility. “We still need to clean up… I’ll put your mom’s things in the laundry separately, and place them back in her room. Please clean up while I’m down there. When we get the room spic and span, then we can play some games! What do you want to play tonight?”

Andrew didn’t speak for a moment, but then replied, “Dragon Warrior X.”

She had heard of it, and knew of the character design. “Okay, I’ll be that big ugly orange creature and you can pick the character of Princess Claire or something!”

______

A few weeks later…

“Okay, your sister is fast asleep,” Jessica said at 9:15 pm. 

“Great!” Andrew said with excitement. 

Over the past few weeks, he had lied less to Jessica, and admitted more of his desires. Jessica, being the awesome babysitter that she was, thought that bonding with Andrew would not only include video games, but also some things that were more up Casey’s alley… like doing nails and playing dress up.

“I haven’t worn these yoga pants in years, so it’s all yours, and PINK had a sale this week, five panties for $10. These are your style,” said Jessica holding up a pink laced thong amongst some other bright colored sissy panties.

Andrew felt like he was in heaven. Ever since admitting his feminine side to Jessica, she had been extremely supportive in his journey of gender exploration. “I love them!” he said enthusiastically.

“I knew you would!” she said smiling.

A few minutes later, they found themselves watching a movie on the living room sofa together. Andrew admitted that he liked “being one of the girls around here” and to sometimes forget that there was a penis down there spoiling the fun. He was wearing the new thong she had bought him, the black tight yoga pants that looked like they gave him a girlish figure, one of Jessica’s old purple lace push up bras that were stuffed giving the illusion of B-cup breasts, and a pink girly cut shirt that said, “Always a Daddy’s Girl” on it. 

His nails had been painted, both on his hands and feet. The pedicure could be easily concealed with socks when it came time to go into hiding, but there was disappointment in the fact that he would have to remove his fingernail polish later that night, before his mom found out.

To add to his feminization, he started shaving his legs, thanks to Jessica’s sisterly-like advice on how to properly put cream on and shave down there, along with his armpits. For additional hair, though, Jessica had bought him a brunette wig for about $50 at a costume shop that had a slight waviness to it. He loved twirling his fingers around the end of it. There was no chance in hell he was going to be able to buy anything like that by himself, either in-person or online, so Jessica was a savior when it came to getting his hands on transformation materials.

On the sofa, Andrew was fully decked out in girl mode, with his wig and some light makeup, along with the comfy outfit that made him feel like a girl. 

“Oh no!!!!” Jessica said, putting her hands over her mouth as she watched, wide-eyed, the scene in the movie where the secretary accidentally throws away the adoption records of her best friend.

“I hope she still gets the baby!” said Andrew, not expecting that he would like a movie like this, one aimed at older girls. He snuggled closer to Jessica as an excuse to get to touch her in the living room. There were still no moves made, though, as he had found out that Jessica had a boyfriend. Not that stopped his fantasies.

“Thanks, Allie,” Jessica said in response to the name he now liked to be called.

Andrew suddenly freaked out as he heard the front door open, and his mom announced her presence. 

“I’m home!!” yelled Ms. McLandon, smiling greatly after having some close interactions with her new boyfriend.

He hit the floor as if someone had just thrown a pipe bomb, and looked for the closest place to hide.

Jessica calmly paused the film and got up to welcome her back home. “Welcome back! How was your night, Stacy?”

“Perfect! Casey is sleeping like a baby and Andrew and I were just watching Models to Moms.”

“WHAT ARE YOU DOING?!?!” Andrew whispered at Jamie between clenched teeth, undecided if he just wanted to take off the wig and fake breasts immediately, and hope the hell his Mom wouldn’t notice he had yoga pants on… but then again there was the makeup.

“Oh, I’ve been wanting to watch that for months! How is it?”

“Funny, but sweet too! Miranda Raven is so hilarious in it!”

Ms. McLandon walked into the living room, closer to the sofa where Jessica was standing. Andrew was still on the floor, shocked that Jessica had not tried walking towards the front door to stall his mom while he tried to play escape artists and return to his room where he could take off all this sissy shit.

“Where is Andrew at?”

“Right here!” said Jessica laughing.

Andrew felt his penis shrivel in humiliation. He became very sweaty, knowing his mom was about to see him. Why in the hell did Jessica just say that?

Ms. McLandon walked closer with a smile that matched Jessica’s, and then saw her sissy son on the floor, dressed like a girl. “Andrew… what are you doing on the floor?”

Wait…What was he doing on the floor? Why didn’t she question that he was dressed like a girl? He nervously turned his head, since his cover had already been blown, and looked up at his Mom, who was still smiling.

“I’m sorry, Mom…” he apologized.

“Aww, you don’t have to apologize, honey. You look like a pretty girl.”

“Wait… you aren’t mad?!”

“Of course not, Andrew. I love you no matter what you want to wear.”

Andrew felt very relieved, but there were still some unanswered questions. Luckily, Jessica was there to explain things to him.

“Yes, I told her, Allie.”

“Oh, that’s your girl name?” asked Stacy, who came to hug her baby.

“You said you weren’t going to tell anyone!” said Andrew, feeling like this was the first promise Jessica had broken.

“I didn’t, though the agreement was that I wouldn’t tell anyone outside the house! Remember?”

He had a hard time remembering the vague statement that was made the first night he was caught crossdressing.

“I’m really not mad honey,” said Ms. McLandon. “I want you to be yourself. Are you happy when you are dressed like this?”

“Yeah…” he said still shocked.

“Jessica told me a few weeks ago, because she felt like I needed to know everything that happens here when I’m gone. She told me about how she found my clothes in your room and the talks you’ve had.”

His face turned even more red as she embraced him in a motherly embrace.

“Does Casey know?”

“Not yet,” said Ms. McLandon. “We are going to have to slowly introduce her to your feminine life.”

“Maybe Princess Dress-up Party next week?” asked Jessica with a slight laugh.

“That could be a start,” laughed Ms. McLandon with her.

Andrew didn’t like the idea of his little sister finding out, since she might tease him, but he took the liberty of knowing he may be able to dress around the house more often.

“I have a present for you later,” said Jessica. “My mom found one of my old homecoming dresses. A huge tulle gown and I think it will fit you perfectly!”

Ms. McLandon smiled and held her boy tightly. “Isn’t she the best babysitter ever?!”

Andrew smiled, “Yes… yes she is.”