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Mothers (and sisters) know best Chapter 1

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CHAPTER 1
A SPLASHING VISIT

In the town of Oakwillow, down on Chestnut Street, there were a number of almost identical houses. From about 20 houses most of them were occupied. Families with average or above average income lived there. Each house had 3 bedrooms, 2 bathrooms, one kitchen and one living room, along with the backyard and the shed. Most of the houses consisted of families of 4 or less. They weren't really suitable for more than 4 people. Most of them had a dad, a mom and 1 or 2 kids, and if a family would ever be blessed with another child, they would usually move to a bigger house. Many of the residents of Chestnut Street were average people, with decent wages that led happy lives. There wasn't anything strange, interesting or even remotely peculiar about the residents or Chestnut Street, except perhaps for the residents of house number 13. 

What was strange about house number 13? Well for starters, there were 5 members. Unusual, but that wasn't the strange part. The house consisted of 4 women and one man. One would assume that it was a happy couple with 3 daughters but that was only be half-right. The residents of house number 13 were indeed happy but the house didn’t have a dad. Instead the house was occupied by 2 teenage girls, a younger boy and, not one, but two mothers. Believe it or not, that still wasn't the strange part. Both mothers had a daughter from their previous relationship and both of them had bad luck with men. One of them was left when she was pregnant with her second child and the other mom got out of a bad marriage. While a lesbian couple with children wasn't a big deal to anyone in Oakwillow, nobody expected such a union to last for a long time and that's exactly where the strange thing starts. Surprisingly this union worked out well. The two daughters clicked almost instantly. Shortly after moving in together they became best friends and after a year they refereed to each other as sisters. The mothers were no different. Since both of them had truly horrifying past relationships, nobody expected them to ever find love again. However, ever since they decide to live together their lives were full of laughter and joy and love oozing everywhere. They were probably the most interesting house on Chestnut Street, two families that joined forces and made it all work. The mothers had jobs with decent wages, the daughters did well at school and were also very athletic and popular among their peers. Everyone always smiled whenever they saw this family full of girls. Everything was going pretty much perfectly for them.

Jennifer Michaels was the oldest resident in house 13. She was a stunning 42 year old woman with shoulder-length (usually) brown hair. She had a bit of a chubby figure but she definitely wasn't fat, just a bit curvy. She often joked that after her second child, she would never be able to regain her perfect body.
Since she worked an office job, she always dressed formally. Her outfit usually consisted of a short black skirt, a working coat and sky-high-heels. Heels seemed to be her favorite thing to wear. Jennifer had her first child (a beautiful daughter she named Lisa) when she was 25. She and her college boyfriend were dating for 3 years before she got pregnant. After giving him the big news, the boyfriend at first seemed really happy. They moved into a small house and after 3 years Jennifer was informed by her doctor that another baby is on its way. Unfortunately, just as she was about to give her lover the big news for the second time, he told her that he was leaving her for another woman. This, naturally, broke Jennifer's heart after which she declared that she was officially done with men. Despite this, she still loved her second child to death and swore that she would raise him to be respectable towards women, unlike his father. After the nasty break-up, she spent the next 13 years living with her parents. Even though they offered to provide everything for their grandchildren, Jennifer was too proud. She paid rent to her parents and provided her children with everything they needed. It was a tough life but at least her children were happy. Things got much happier when she met her.


 Emily McCormick who was 35, was a much slimmer and more athletic than Jennifer. She had small but very visible muscles and she often showed them off while wearing her yoga outfits. Ever since Emily could remember, she had short hair. Her hair used to change colors almost on a daily basis. Sometimes it was blonde, sometimes it was red and sometimes it was dyed in a crazy color, such as blue or pink. She claimed that only the sexiest girls could "rock" a short hairstyle like her and get away with it. She had her daughter when she was only 18. Emily claimed that she had made some really bad choices when she was younger but that her daughter was the best mistake that ever happened to her. When Emily got pregnant she was forced into a wedding by both her family and the father's family. Needless to say, it didn't work out. Emily's husband had a drinking problem and would sometimes beat her. At first, she was tolerating the abuse until the day he hit her daughter. After this, she left him and never looked back. The worse thing was that, even before the abuse and the beating, Emily never found her husband, or any other man, attractive. Emily was a cheerful and an outgoing person. She always looked on the bright side, even when things were down. She often used the saying: “After the rain, sunshine will come”, and she lived her life based on that. After the divorce, she decided to become physically stronger so she took up yoga. A few years of dedicated training and she became a licensed yoga instructor and even worked at two different locations because she needed the money to raise her daughter properly. It was naturally a hard life, but it got much easier when she met her.


It was love at first sight when the two middle aged women met. Emily instantly fell in love with Jennifer. Jennifer was unsure at first, but she definitely felt a spark. The two single moms had a few friendly dates and as they spent more time together, they realized that friendship was just not enough. They fooled around for a year, introduced their kids to each other and finally decided to join forces and buy a house on Chestnut Street. With both of their wages, they could easily afford the upkeep and would have enough money to support all their children.


Lisa Michaels was Jennifer's 17 year old daughter. She was a stunning teenage beauty who was also very smart. She had long brown hair, the same color as her mother (her natural hair color at least), only her hair was much longer. Lisa loved her body and would never miss an opportunity to show it off. She almost always wore dresses and sandals claiming that she had great “goods” and that there was nothing wrong with showing them off. At first glance, she definitely seemed like a slutty girl, but that couldn’t be further from the truth. Lisa was extremely bright. She was the problem solver of the family and the peacemaker whenever a fight broke out. She was a sister anyone could rely on. She only enjoyed, as she claimed “Teasing the weaker sex" by wearing somewhat revealing clothes to get some extra looks. Her clothes always screamed “trendy” and “look at me”. However, anyone who spent more than 10 minutes with her would realize that this was not a naughty girl but quite the opposite. Lisa also had a bit of a temper problem when people would borrow her things without asking but other than that, a lovely daughter every parent would be proud to have.

 

Beth McCormick was Emily’s only daughter. Unlike Lisa who leaned more towards being beautiful, Beth was the definition of the idiom “Cute as a button”. Beth would only ever wear things that ranged from people saying “Awwwwww” to people saying “Oh my god, she is so precious”. Beth was like the “baby spice” of the family. She would always wear something frilly and extremely girly but she would never cross the line to looking ridiculous. For example: on some days she would wear the frilliest pink shirt with sparkles, glitter and anything else eye catching but then she would wear very plain jeans. She would also wear, the cutest, frilliest skirt with lots of ruffles along with black stockings and a plain white blouse. Beth always claimed that she could wear pretty much anything and still look cute if she balanced it out with other clothes and it was true. She always looked cute, no matter what she wore. Part of this was because she also knew how to sew and would often make clothes for her and her family. Despite the cute and innocent looks, Beth was a beauty just like her mother. She had a perfect body and perfect teeth. Unlike her mother, she had long blonde (dyed) hair that she often put in pigtails or any other style she would find cute.  She wasn’t as good at school as Lisa but she wasn’t horrible either. She loved clothes and fashion, but most of all, she loved being cute. Whenever someone was in a bad mood, Beth made it her job, to cheer that person up. She loved to act silly and would always become a clown when the world needed one.

 

Because of their past and their colorful personalities, the neighborhood would often call house 13 “The House full of Pretty Girls”. Despite the name, the house also hosted one male resident.

 

Mike Michaels who was 14, was the only man in the family. Unlike the rest of his family, who were relatively active and outgoing, Mike was a complete loner. He had a very skinny body, barely any muscles and shoulder length messy brown hair that he barely even washed. He was also much shorter than the rest of the household which made him look even younger. Mike was the black sheep of the family. Even though he loved and respected his mother, his Sister, Emily and Beth he never cared much about spending time with his family, and that bothered the other household residents. Mike felt very overwhelmed by being surrounded by so many women that he sealed himself away into the world of video games. At times, he would only ever emerge from his room to go to the bathroom or to eat. At first, everyone thought that this was just a phase but as time went by without any improvements, everyone started to get worried about Mike. His sisters and mothers begged him to spend some time with them but he always declined. Everyone tried to get Mike’s attention. Beth tried to make superhero costumes for him, Lisa tried to hook him up with her girlfriends, Emily tried to teach him yoga and his mother tried to go to comic conventions with him but nothing seemed to keep Mike’s attention for long. He simply did not want to spend time with anyone in his very loving family. Not even people outside his family interested him, as he had no friends in school and the neighborhood children that were about his age didn’t interest him at all. This was starting to become a huge issue for the rest of the girls in house 13 and they were seriously starting to worry about the future of the only boy in the house. That was until one day…

 

One chilly summer day, the family was visiting Emily’s mother in a town that was about 2 hours away by car. The family made these visits annually and it was considered very rude for anyone to miss them, so even Mike, who would usually avoid such gatherings, had to come. Emily’s mother lived in a small apartment on the first floor of a building. The apartment was barely big enough to welcome 5 people but that never stopped the Michaelss and the McCormick family from visiting. Once they arrived the girls greeted the grandmother with lots of kisses and hugs. Mike was also forced to hug her. She was a very warm and welcoming woman, as soon as Emily and Jennifer started living together she demanded that Jennifer calls her “Mom” and Lisa and Mike “Grandma”. While the girls were chatting and catching up, Mike stared out of the window. There was a single swing outside the apartment and, for some weird reason, Mike got the urge to swing for a while and get lost in his thoughts.

“I’m going outside for a while”, Mike declared.
“Why are you going outside sweetie? It’s still wet from the rain yesterday and wouldn’t you rather chat with your grandmother a bit more”, Jennifer begged her son to socialize at least a little, even though she knew that Mike would probably find an excuse momentarily.

“I’m just a bit... I just need some air”, Mike said and went outside.

Grandma looked at the floor and sighed.

“He is still the same as he’s always been” Grandma said sadly.
The other girls in the room silently looked at the floor as well.

 

 

 

Outside Mike made his way towards the swing. It was a little cold that day, so he was wearing a jacket and some long jeans. There were a few puddles on his way towards the swing so he carefully hopped over them. Once he made it to the swing he noticed that there was a puddle of water right under the swing. He thought nothing of it and just sat on the swing. At first he only sat down, barely even moving, thinking about what game he should play next. He gently started swinging his legs back and forth which forced his whole body to start swinging. Before he knew it, he was swinging like a little kid and… he was having FUN!
“Holy crap, this is so much fun! Why is this even so fun? Who cares anyway”, he thought as a smile began to form on his face.

He had spent so much time isolated from the outside world that he had forgotten just how much fun swinging on a swing-set could be. However, that wasn’t enough for Mike. After about 5 minutes of swinging he wanted something more adrenaline pumping.
He thought about doing a very high swing jump, just like the ones he had seen the cool kids in kindergartens do. He was 14 after all, so how hard can a swing jump be if preschoolers can do it. He swung himself higher and higher. Just a little bit more. He was ready to jump off the swing and into the distance but just as he was about to let the chain go, he got scared and grabbed it back. This caused him to lose balance and he went flying back with the swing right into the puddle underneath it. A huge splash could have been heard that even caused some people to look outside and stare at the poor unfortunate boy who luckily didn’t get hurt. His pants and underwear were completely soaked.

Even though he hadn’t done it in years, Mike’s eyes started to water and he began to cry. He started running back to his grandmother’s apartment crying. As he ran he was splashing all over the road as he was way past paying attention to where he stepped. Once he entered his grandmother’s apartment, everyone immediately noticed him.

“Oh my God Mike, what happened to you”, Lisa ran towards him.

In a flash everyone was around him. While crying, Mike explained what had happened to him.

“This is exactly why I told you not to go outside”, his mother said firmly.

This did not help Mike’s crying.
Emily made her way towards Mike and hugged him. He hugged her back.
She didn’t let go of him until he calmed down.

“Now sweetie, I think you need to get out of those pants”, Emily said.

“Wait mom, do we have anything for him to wear”, Beth asked Emily.

“Umm, Mom, do you have any Grandpa’s old clothes?” Emily asked her mother.

“Oh you know I’ve given all of it to charity”, grandma replied apologetically.

Everyone stood there around the soaked boy until Beth spoke.

“Well… I do have a pair of pants that I brought in case it got any colder”, said Beth, who at the time was wearing a very frilly skirt with leg-warmers.

“This caused Mike to look confusingly towards Beth as she went to her backpack and brought a pair of skinny blue jeans.

“I don’t know. They might just fit him”, she said as she held them up for everyone to see.

“ABSOLUTELY NOT!”

Everyone looked towards the direction those words had come from.

The always quiet and lonely Mike had an angry look on his face.
“THERE IS NO WAY IN HELL I AM WEARING GIRLY CLOTHES”, he shouted loudly.
His shout was so loud that it came as a shock to everyone. Nobody had ever heard Mike raise his voice so much. Mike made sure to make it clear to everyone present that he seriously did not want to wear his sister’s jeans.

“Ummm… OK”, Beth said, still in shock from what she had just heard.
She went back towards her backpack to put the jeans back when Jennifer stopped her.
“Hang on, Beth”, said Jennifer.
Jennifer headed towards her son. She crouched down to match his height, looked him directly in the eyes and said:
“First of all, young man, it is your fault you got wet. Second of all, instead of being thankful that you have such a wonderful sister who would let you borrow her things you yell at her, and finally, why the HELL ARE YOU EVEN YELLING IN FRONT OF YOUR GRANDMOTHER LIKE THAT, you should be ashamed of yourself, we are only trying to help you here.”, she said angrily.

Mike didn’t have anything to say to all that, so he just went quiet.
An awkward silence began and lasted for about 40 seconds.

“Now, work together with me Mike. Grandma doesn’t have any Grandpa’s old clothes. The only one who has something dry for you to wear is Beth. If you stay in your wet clothes you will catch a cold, which nobody wants and I’m not having you ride in the car in those wet pants. So just be a good boy, and put on those jeans”, Jennifer calmly explained.

“Yeah, and seriously, just look at them. They aren’t even that girly”, said Emily pointing at the Jeans that Beth was holding to which everyone nodded.

Mike started to get angry again but even he had to admit that he was out of options.

His mother took his hand and the jeans and headed towards the bathroom.

She closed the door and told Mike to take off his pants. At first Mike protested but then Jennifer calmed him down saying that he has nothing to be ashamed of around his mother.

Mike reluctantly took off his pants. He grabbed the jeans and just as he was about to start putting them on, his mother looked at him and spoke.

“Oh my God, you even got your underwear wet”, she said obviously annoyed.

She opened the door to the bathroom and left the door open which caused Mike to be seen on his underwear by everyone present.

“Mike’s underwear is wet. What are we going to do?”, Jennifer asked.

At first there was silence and then Lisa sighed and dug through her purse.

She presented a sealed plastic container.
“Throw them away, once we get home”, she said with an annoyed voice like she was paying for a parking ticket. She handed the container to her mother.

Jennifer took the container and headed back into the bathroom with her son.
She opened the sealed container and pulled out a plain pair of cotton panties.

As soon as Mike saw them his eyes widened.
“No way mom! No way am I wearing panties”, he said those words loudly but not as loud as he yelled earlier.

Jennifer looked at her son. “Do you have a better idea?” she stared at him.

“Can’t I just wear the jeans on my underwear?” he asked.

“You would ruin your sister’s jeans that way and would also catch a cold, sorry but your underwear simply has to come off”, she explained.

“Wait, can I just wear Beth’s jeans without any underwear”, Mike suggested with a twinkle in his eye, thinking this would be a better solution.

Jennifer looked at him angrily.
“Son, don’t make this a bigger deal than it already is. Now, I’m going to leave you here until you have changed. Put on those panties and the pants and come out”, she said that, exited the bathroom and closed the door.

Mike was left there with a pair of Beth’s jeans and a pair of Lisa’s panties. He hated the situation he was in. He knew that there was no way out of it so he angrily removed his wet underwear. He took the freshly unpacked white panties that were left there. They felt incredibly soft. “Yuck” he thought, but he still had no choice. He raised each of his legs and put them through the holes on the panties. As soon as he got them in place he felt very weird. The panties were very comfortable but the fact that they were made for girls made his stomach twist. The panties were plain white, but were obviously made for a female body. Disgusted with his current situation he reluctantly took Beth’s jeans and proceeded to slide them up his legs. Once they were in place and they were buttoned, only then could he feel how amazingly tight they felt. They made his hips look wider and his butt stick out, while his legs were hugged closely by the much softer fabric than he was used to.

 

He slowly came out of the bathroom.

“Hey, looking good girlfriend”, Beth yelled jokingly.

“SHUT UP! DO YOU THINK I LIKE THIS? WELL, I DON’T. SO SHUT UP!” shouted Mike.

Again, this caused confusion. People were used to barely hearing the lad talk at all, but there he was standing and using more emotions in his speech than anyone had ever seen or heard him use.

“Don’t be like that Mike, they really do look good on you, and nobody can really tell they are made for girls”, Emily reassured him.

“They DO NOT look good on me”, he angrily replied.
Again, people were shocked, as they were just expecting him to keep silent and not reply.
It was obvious to everyone that wearing his sister’s pants was really bothering him.

Jennifer came over to him and pulled the sides of the jeans to take a peek at the panties.

“What the hell?” Mike flinched and his mom let go of the pants.
“Relax honey, I’m just checking to see that you aren’t cheating”, she said teasingly.

“Well… cut it out then”, he said angrily. Again a reply from Mike. In just ten minutes it seems like he had said more than what he would usually say in a whole week.

“Well it’s about time we head back home grandma”, said Emily.
Everyone said their goodbyes and went back into the car.

Jennifer sat at the driver’s seat, Emily rode shotgun, while Mike sat in the middle seat with both of his sister’s on each of his sides.

As they rode, Mike kept his arms crossed. There was an obvious frown on his face.
Usually during long car rides, he would have taken out his 3DS or PS Vita and not pay attention to anyone, but for some reason none of those were out. He just stared into the distance until he felt a poke on his left.

“So how do you like my jeans sis?” asked Beth, which caused everyone except Mike to giggle a little bit

“I told you to cut it out. Just leave me alone. I don’t like this any more than you do!” he said.

“Oh what are you talking about sis, I love sharing clothes”, said Beth jokingly, followed by giggles from both the back and the front seats.

“Hey, stop calling me “Sis”! As soon as I get home, I’m taking the pants and the underwear off and we will forget that any of this ever happened”, he said.

“They are actually panties sis, we don’t call them underwear”, Lisa added teasingly.

Now even Lisa started calling him “Sis”. Mike was not amused.

“Look, I don’t care what they are called, they are made for girls. I’m a boy, and boys don’t wear stuff like this. I seriously can’t wait to get back home and slap on a pair of boxers and some school slacks”, Mike explained angrily. He wasn’t shouting because he feared that his mom might give him another lecture again.

“Listen to you sweetie”, said Jennifer while keeping her eye on the road, “You are talking so much! I can’t remember the last time we had a conversation with you”, she said happily.

“Mom, what is wrong with you. This is not a conversation. I’m angry. I don’t like this, I want to get out of these dumb pants”, he complained.

“Sorry Mike. It’s just… you are always so quiet. We try very hard to get you to talk to us, to tell us how you feel or what you are thinking of but you always shut yourself into your room and avoid us. I’m just so happy that we finally got to exchange a few words with you, even if they are just shouting words”, Jennifer said that very sincerely with a hint of sadness.

Mike couldn’t reply. Was he really all that quiet? Maybe he could try a little harder to talk to his family. He thought for a moment and then Beth interrupted his thinking.

“Yeah, Jennifer is right, I miss talking to you, come to think of it, ever since me and mom moved in, I don’t think we’ve ever had a conversation with you. Hey, maybe we should get you to wear girl’s clothes more often so you would speak to us”, she said laughingly.

Everyone started laughing at Beth’s comment. Everyone except Mike, of course.

“Enough! I don’t want to talk about this anymore. Stop teasing me already. Jeez, why do you keep doing this”, he asked.Emily turned around from the front seat to face him. “Because you are still talking, and because you look so adorable in your sister’s jeans”, she said it and started giggling.

Naturally, this caused Mike to rage again, and the rest of the car ride passed relatively fast with someone often pointing out something about the pants or the panties and Mike furiously defending himself.

Needless to say, Mike spoke more during that car ride than he ever did in a very long time and his Mothers and Sisters really liked the communication even if it consisted of mostly teasing and shouting.

As soon as the car pulled over in the driveway of house 13 on Chestnut Street, the little boy in girl’s jeans grabbed his mother’s keys and with amazing speed unlocked the door and rushed to his room to change his lower clothes. Mike was back to being his old, non-talkative self again, and after taking a shower and freshening up in the bathroom, he retreated to his room from which he didn’t come out until the next day.

A couple of months ago, I was just derping on DA, when I noticed that I had received a note from someone. Someone actually wanted to pay me to write a story for them. The deal was that I write a 4000 word story about a boy who get feminized by his mothers and sisters. Since this was my very first commision I wanted to make it good, so, I went a little crazy and ended up with... 40000 words. My commisioner, juliasissie, was kind enough to let me share this story with the rest of DA and since the story was based on juliasissie idea, any praise you may have for the story is also a priase for her. 

This is Chapter 1 of a four chapter story.
Chapter 2 coming soon 
© 2017 - 2024 alksndr202
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huberthowhow's avatar

I think Mike needs a good spanking. His rudeness to both sisters, despite their attempts to help him, is inexcusable.