Synopsis: Ian isn’t your typical thirteen year old boy, but he hopes to make some new friends when his father gets a promotion at work that means they have to move to a new town. He meets some boys that seem like they could be his friends, but he soon finds that they aren’t really his friends, but he does find a true friend, and also someone to help him explore his love of dressing as a maid. Just when he thinks he’s found what he wants to do with his life, things go wrong and his life falls apart around him.
Synopsis: Ian isn’t your typical thirteen year old boy, but he hopes to make some new friends when his father gets a promotion at work that means they have to move to a new town. He meets some boys that seem like they could be his friends, but he soon finds that they aren’t really his friends, but he does find a true friend, and also someone to help him explore his love of dressing as a maid. Just when he thinks he’s found what he wants to do with his life, things go wrong and his life falls apart around him.
Chapter One: New home, New start.
Ian Phillips was sat in the back of his father’s car looking at the kids playing on the street as they pulled onto the driveway of the new house. Ian wondered how long it would take him to make some new friends in this new town. His father had been promoted at his job, but it meant them moving to a new County, so Ian had been forced to pack up his life and move with his parents as he was only thirteen and he had no family that he could stop with back at the old place, and he wasn’t very good at making friends with people, so he wasn’t leaving any close friends behind, just a couple of kids he use to speak with at school. They were kind of the other kids that didn’t fit in with any of the other groups you got at school.
“Don’t look so down sweetie, I’m sure you’ll soon make some new friends.” Gail, his mother said from the front seat when she saw how down in the dumps he looked when his father had parked up.
“I know mom.” Ian said with his best smile. “I can’t wait to get out on my bike and investigate the area.” He added.
“You’ll have to wait until we’ve got unpacked first son.” Shawn, his father warned.
“I thought the removal people sorted all that out.” Ian whined.
“They will place all the furniture and boxes in the house, and even in the rooms for us, but we still need to get everything unpacked and put away.” His father explained. “And yes you will be helping us do all that.” He added with a frown. “I’m going to have you with a bedroom full of boxes for the next couple of years.”
“Yes father.” Ian sighed.
They all got out the car and then Shawn let them all into the house. Ian had just gone up the stairs and found the room that was going to be his, when he heard the sound of a large truck pulling up outside. Ian went over to the window and saw it was the removal people there with their things from the other house.
Ian tried to keep out the way while the men brought everything into the house, and then he helped his parents get everything unpacked and put away. Ian then spent some time unpacking his things in his room and trying to get it looking like his old room, but this room was much bigger. He wanted to get everything unpacked himself and put away, so his mother didn’t find things he didn’t want her to see. He found the suitcase with the items in that belonged to Isabella, Ian knew his mother and father would never understand why he had a suitcase full of female girls clothing that was all in his size. Ian had been drawn to female clothing as far back as he could remember, and over the years he’d managed to get a small collection of items together, which he kept hidden from his parents in a small case that was now hidden at the back of his closet.
“Do you need any help sweetie?” His mother asked after knocking on his bedroom door and then just entering the room.
“Mum...! Can’t you wait for me to say it’s safe for you to enter?” Ian whined. “I could have been naked in here.”
“And why would you be naked while unpacking your things?” His mother asked looking a little too smug with herself.
“Well I could have been doing something else that you wouldn’t want to see me doing.” He countered.
“Like what?” His mother asked trying not to grin now.
“Never mind, just wait for me to invite you in next time.” He said just before he went back to putting things away.
“You should lock your door if you don’t want me walking in on you.” His mother pointed out as she looked over towards the bedroom door.
Ian hadn’t noticed his bedroom door had a lock, the one at his old house didn’t. He knew right away that he would be making good use of that lock here, so he could let Isabella come visit. He even had his own bathroom at this house, so he wouldn’t have to worry about getting changed when he needed a toilet break.
He soon had his things unpacked and then he went down to have some dinner with his parents before he was allowed to get his bike out and go explore the area.
“Don’t go too far, and keep out of trouble.” His father warned.
“I’ve only just got here dad, what trouble could I get in?” Ian asked.
“With your track record at the old house, I won’t put anything past you.” His father frowned.
“I was getting picked on dad, so it wasn’t like I went looking for trouble.” Ian snapped just before he walked out the back door and slammed it shut behind him before his father could say anymore.
Ian wasn’t one of the largest kids around, so it had caused him to be the target of some bigger kids in his old town. His father blamed him for not sticking up for himself more, but Ian found it better to run away from the bullies rather than get a beating from them. He hoped that he could make some more friends here in this new place, and stop all the bullying before it starts.
He’d been riding his bike around the block for just over half an hour when he came across a group of boys on bikes.
“Hey! You the new kid that’s moved in to number Eight Elm Close?” One of the boys asked as he blocked Ian’s path through them.
“Yes...” Ian said trying not to look scared as he found the boys crowding around him as they sized him up.
“Welcome to the neighbourhood.” The boy smiled as he held out his hand to shake Ian’s. “I’m Dean, and this is Paul, Simon, Peter and Joe.” Dean said as he pointed at each boy as he said their name.
“Hi, I’m Ian.” He smiled back as he shook each boy’s hand.
“That’s a nice bike you have Ian, do you want to hang out with us? We could show you around.” Dean asked.
“Sure, I’d like that.” Ian said.
Dean and the others were soon showing Ian how to get to the local shops, and where the park was, which Ian was impressed with as it had a skate park and a BMX track.
“Do you have a skateboard?” Simon asked as they watched a couple of kids doing some tricks.
“Yes, but I’m not very good on it.” Ian admitted. “Are you any good on one?” Ian asked Simon.
“Si is mega cool on a board.” Peter said before Simon could answer for himself.
Simon just shrugged like it wasn’t a big deal. “I’m not that good; it’s just that Pete is really bad.” Simon chuckled as he had to duck a slap across the back of the head by Peter. “Drag your board out sometime, and I’ll give you some pointers.” Simon said as he jumped off his bike and started dancing around as he kept slapping Peter on the head in a playful manor.
“Thanks, I’ll do that, but I must warn you, I’m not very good.” Ian said with a grin as he watched Peter and Simon playing around. He was happy that he seemed to be making friends already, and it was only his first day in the new house.
The time was getting on and Ian knew he needed to get home before his parents started to worry about him, so he arranged to meet up with the others the next day at just after noon. Simon was going to give him his first lesson on how to ride a skateboard properly.
“I was beginning to worry about you sweetheart.” Gail said when she saw her son enter the kitchen.
“Sorry mum, but I met some new friends and I lost track of the time.” Ian grinned excitedly. “One of them, a boy called Simon, he’s a really good skateboarder and he said that he’d show me a few things.”
“That’s nice sweetie, but please be careful; you know how much I hate it when you go out on that thing.” His mother said looking worried.
Ian’s mum worked as a nurse, and she’d seen too many children come into A&E with their faces bashed up because they fell off a skateboard.
“I will mum.” Ian smiled as he grabbed a can of coke out the fridge and went up to his room to carry on sorting out his room.
Once in his room he opened the can of pop and then took a sip before he set to work getting undressed so he could take a shower and then let Isabella out for a couple of hours. He’d locked his bedroom door and made sure the lock worked, the last thing he wanted was to think he was safe to dress as Isabelle, just to find out the lock didn’t work. He use to wedge a chair under his bedroom door at the old house to stop his parents walking in on him, but this was much better, not that his parents ever bothered him when he was in his room.
Ian was soon out the shower and dried off, so he set to work slipping on a pair of pink silk panties he’d bought online, thanks to his parents trusting him with an EBay and PayPal account. Ian knew his parents checked what he bought on his EBay account, but not his PayPal one, so he’d set up another EBay account to use when he wanted to buy something for Isabella. He’d bought a lot of things for Isabella that way, and due to both his parent’s working, he was able to have the stuff delivered to the house without his parents finding out, and if they did, he would just say it was a birthday gift for one of them, or a Christmas gift if it was past their birthdays.
Once he had the panties on, he picked out a padded bra to wear. He added a little bit of padding, just to make his breasts a little bigger, but he was still a little young to be wandering around with large breasts, and he liked to look like a normal girl for his thirteen years of age.
With his underwear on, Ian pulled out the dress he was going to wear while he sorted out his room. The dress was actually a maids uniform in black silk with lots of petticoats. Ian had loved the way these maids looked ever since he saw an old movie when he was younger. He knew he had to have one as soon as he saw them being sold at a shop on EBay.
Ian slipped on a pair of nearly black tights and then a second pair of frilly panties before he slipped the dress over his head and then struggled to pull up the zip at the back. With the dress on and smoothed out, he then tied a small white piny around his waist before he stepped into a pair of ballet flats. He would borrow a pair of his mothers black heels if he had the house to himself, but he knew his parents would hear him walking around his room in heels, so this was the best way to play maid with them in the house.
Even though Ian had let his hair grow out as much as his father would let him, it was still too short to do anything to feminine with, so he’d bought a maid’s cap to go with the uniform. He soon had the cap pinned to his head and he looked in the mirror and saw maid Isabella looking back at him.
“Good evening Isabella.” Ian grinned as he did a little curtsy, and the girl in the mirror did the same.
Isabelle set to work sorting out the room with a smile on her face, but it was taking longer to get the room tidied up due to Isabelle stopping every time she passed the mirror. She would do a spin and giggle as she saw the skirt on the maids dress flare out to show all the puffy white petticoats and her legs encased in the black pantyhose.
Ian never risked using makeup because his parents had been known to call him downstairs once in a while, and it would take too long to remove the makeup, so he just played dress up with the clothes.
He finally had the room looking clean and he then sat at his desk to set up his computer. He couldn’t go on the internet yet though because they were waiting for the engineer to come and hook up the new broadband internet access. Once the computer was set up, Isabelle picked up a book and then relaxed on the bed until it was time to get ready for bed and then go to sleep.
Isabella didn’t own a night gown yet, but Ian was going to fix that, now he had a lock on his door, but for the time being he decided to sleep in the bra and panties he was wearing. He brushed his teeth and then smiled before turning off the light in his bathroom and then jumping into bed, loving the feel of the bra wrapped around his chest.
Ian was just getting ready to leave the house the next day, so he could meet up with the boys he’d met the day before, when there was a knock on his bedroom door just before his mother pocked her head in. The talk they’d had about her waiting to be invited it forgotten.
“Sorry to bother you sweetie, but this box ended up in our bedroom by mistake.” His mother said as she placed a medium sized box on the bed.
“Thanks mum.” Ian smiled as he stepped over and opened the box to find it full of old toys he never played with anymore.
“Your room looks tidy.” His mother said as she looked around. “I swear you must have a maid hidden away in here.” She giggled. “I thought teenage boys were suppose to never clean their rooms, but yours always looks so clean.” His mother added with pride.
‘If you only knew how close to the truth you are mother.’ Ian thought to himself about a maid being hidden in the room. “I do, and her name is Isabella.” Ian said in a fake whisper as he pretended to look around the room like he was telling his mother a big secret.
“Well get her to clean the rest of the house then as well.” His mother said in the same fake whispered tone. “It will save me a lot of work.” She added with a giggle just before she left the room again.
Ian found himself wandering out the house and up the road thinking about whether or not his mother would let him dress as Isabella and play at being their maid, but he already knew his father would have a fit if he ever saw him dressed as Isabella, and his mother wouldn’t be much better either, so he shoved the thought from his mind and focused on meeting his new friends and getting some tips on how to skate better.
Simon and the others were already using the skate park when Ian got there. He was grateful that they were all wearing safety gear like he was. His mother wouldn’t let him leave the house without it.
“Hey Ian...!” Simon shouted as soon as he saw him walking over to them. “I’m glad to see you were smart enough to wear some safety gear like we do.” He added as he held up his hand to give Ian a high five.
“I was worried that you might not wear any, and I’d look a little foolish wearing all this.” Ian said as he indicated the helmet, elbow and knee pads he was wearing.
“There’s nothing cool about grazed elbows and knees.” Simon frowned.
“Yep, better safe than sorry.” Peter added just before he dropped down into the large hollowed out concrete bowl.
Simon asked Ian to show him what he knew, which turned out to be next to nothing, but Simon was patient with Ian and started to show him how to stay on, and even do a couple of little tricks.
They hung out at the skate park until some older kids turned up and started making fun of Ian for not being very good, so they all decided to leave and go find something else to do. Ian soon learned that Dean liked to take risks and see how close they could get to being caught doing something they shouldn’t. Not wanting to look weak in front of his new friends, Ian soon found himself in the garden of a large house which they had to climb over a large wall to get into.
“I don’t think we should be in here.” Ian whispered to the others as they all hid behind a large hedge looking at a house on the other side of a long lawn.
“You need to do this, if you want to be part of our little gang Ian.” Dean said with a grin that made Ian look a little uneasy with what might come next.
“What do you want me to do?” Ian asked trying not to sound scared, even though he was. Ian knew his father would kill him if he got in trouble and brought home by the police.
“We’re going to break into this house, and then we’re all going to run through it making as much noise as we can, and you have to be the last one to follow.” Dean explained.
“Are you crazy?” Ian screeched out, not able to keep the fear from his voice. “My dad will kill me if I get caught and arrested.” Ian added.
“Don’t worry about that Ian.” Simon said in a tone that made it sound like Ian was being silly. “For starts we don’t have to break in because the basement is never locked, and secondly we only ever run through the basement and out the other side into the woods behind the house.” Simon explained.
“The guy that lives here has never come after us once.” Paul said smugly.
“I’m still not sure about this.” Ian said as he looked at the other boys to see if this might be a trick, but he would be going last, so if it was a trap, then they would be running into it first. “Okay then, let’s do this.” Ian said trying to look a lot braver than he felt.
Ian was soon running across the lawn with his skateboard in one hand and his other waving all over the place as he tried to keep up with the others. He followed them down some steps and then in through a door that was shut, but not locked like Simon had said. Ian was soon running faster when the others started shouting as loud as they could. He thought they would be caught for sure due to all the noise.
Peter was just in front of Ian, and Ian saw him reach out and knock a box with his hand, but Ian was going too fast to stop himself tripping over it. Ian went all his length and let go of his skateboard to stop himself smashing into the stone floor of the basement. He was soon back on his feet and running to catch up with the others.
Ian saw daylight at last and he made his way towards it. He soon found himself on another lawn where he could see a forest on the other side with Peter and the others just vanishing into it, so he followed them as fast as he could.
“I thought we’d lost you back there for a minute.” Simon said as he tried to get his breath back, once they were on the other side of the wooded area.
“Pete didn’t help when he pulled a box over right into my path.” Ian frowned as he looked at a smug looking Peter. “Or was that the idea? You wanted me to get caught?” Ian asked.
“What the hell did you do that for man?” Dean asked as he punched Peter in the arm. “That’s not cool dude.” He added as he punched him again.
“It was just a bit of fun.” Peter said as he tried to defend himself from the attack. “No harm done and he passed with flying colours.” Peter added with a shrug.
“Oh crap...!” Ian suddenly said as he realised he’d left his skateboard behind when he tripped over the box. “I’ve got to go back. I left my skateboard back there.” He said as he turned towards the house again.
“Are you insane...?” Simon asked as he placed a hand on Ian’s shoulder to stop him. “You’re going to get caught.” He warned.
“If I don’t get my board, I’m dead anyway.” Ian said. “It has my name and mobile number wrote on it.” He added with fear in his voice over what his father will do if he finds out.
“Just tell your old man that your board was stolen by someone else.” Peter shrugged.
“My dad wouldn’t buy that for a second, and he’d want to know why I didn’t call him right away and let him know.” Ian explained. “And if I call him now, and he speaks to the people that live there and he finds out I called just after the trouble happened in the basement, then...” Ian trailed off hoping Peter was smart enough to fill in the rest.
“Well good luck then man.” Dean said as he started to walk away with the others following.
“Aren’t you coming back with me?” Ian asked looking a little shocked.
“It’s not us that’s going to get in trouble.” Dean said over his shoulder as he kept walking.
Ian was left looking at the backs of the boys as they walked away without giving him a second look. He realised then that none of them would ever be his real friends, so he made his way back to the house and sneaked into the basement this time looking for his skateboard.
He soon retraced his path back to where Peter had knocked over the box and forced him to fall. Ian found his board and was just picking it up when he noticed something black and shiny sticking out the box that he’d tripped over, so he put his skateboard back down and stood the box the right way up to take a better look at it. Ian let out a gasp when he saw that it was a PVC version of a maid’s uniform.
Ian suddenly forgot where he was and how much danger he was in as he pulled the maid’s dress out and held it up in the air to get a better look at it, he then found himself holding it to his body and trying to work out what it would look like on him. It looked like it might fit, and for the first time he felt the need to steal something from another person.
He was soon looking a little worried when he looked in the box and saw that there were shoes and other things in there as well. He picked up one of the shoes and soon dropped it again after seeing that the shoes could be locked on, and the other things in the box looked like restraints for locking the wearer into all the clothing.
‘Who the hell lives here?’ Ian thought to himself as he started to place the maid’s uniform back in the box.
Once he had everything back in the box he went to place it back where it was before Peter knocked it over, but he was soon distracted again when he noticed that the box he was putting back said ‘BLACK M’ on it, but the other boxes all said different colours on it.
‘They can’t all be maid’s uniforms, can they?’ Ian thought to himself as he found himself to curious to stop himself looking.
He was soon opening a box with the word ‘PINK M’ wrote on the side of it. Once he had the box open he let out another gasp as he saw a pink PVC version of the maid’s uniform with all pink restraints and shoes with the same lockable strap to go around the ankle.
Ian soon found himself holding the pink maid’s dress up to his body as he wished he could try it on and see what it felt like to wear the beautiful looking garment.
“You’re not the smartest thief in the world.” A male voice came from just behind Ian, making him jump and drop the dress on the floor.
Ian spun around to find a man stood behind him leaning on a walking cane smirking at him.
“I’m sorry Sir. I wasn’t trying to steal anything.” Ian stuttered out nervously as he thought about his father killing him when he found out what he’d been doing, and the fact he’d been caught playing around with dresses as well.
“Looks that way to me.” The man said with a raised eyebrow as he looked at the pink Maid’s dress at Ian’s feet.
Ian looked down and saw the dress on the dirty basement floor and without giving it a second thought he bent down and picked up the dress before he folded it back up and placed it back in the box and closed it up again.
“I’m sorry about breaking in Sir, but it was just a prank me and my friends dared each other to do.” Ian tried to explain.
“And where are these friends now?” The man asked as he looked around the basement, but he already knew that Ian had returned to the house on his own, as he’d been watching him on CCTV.
“They wouldn’t come back with me when I realised I’d dropped my skateboard.” Ian said as he bent down and retrieved the board from the floor where he’d placed it when he saw the black maid’s dress sticking out the box.
“Don’t sound like very good friends to me.” The man sighed. “You don’t look like you fit in with them either from what I’ve seen.” The man added as he looked at the boxes and then Ian again.
Ian realised what the man was getting at and he went to argue, but stopped again when he saw the look the man was giving him. It was like he already knew that Ian loved dressing as a maid.
“I am sorry about breaking into your house and causing trouble Sir, but I really wasn’t planning to steal anything. We were just running through your basement for a bit of fun.” Ian explained.
“You were thinking about stealing that black maid’s dress though wasn’t you after you realised what it was.” The man smirked.
Ian went to say no, but he didn’t like lying, and he wasn’t very good at it, so he just let his head drop in shame as he admitted. “Yes I did think about stealing the dress, but I fought the urge and placed the items back in the box.”
The man was just about to speak when he let out a gasp of pain and gripped a hand to his chest looking like he was in pain.
“Are you okay Sir?” Ian asked as he ran over to offer aid to the man, not giving any thought to making a run for it like most would have, given a chance to make a clean getaway, but Ian wasn’t going to leave another person to suffer if he could help them.
“I need my pills.” The man said through gritted teeth that let Ian know the man was in some serious pain as he pointed up towards the house above them.
Ian took some of the man’s weight from one side while the man used his cane for support on the other side as they slowly made their way up into the house. Ian let the man lead the way and they were soon in a study where the man fell into a large armchair surrounded by books. Ian watched as the man took a small white pill out a silver tin and then popped it into his mouth and took a sip of water.
The man let his head fall back on the chair and he closed his eyes for a couple of long minutes as he let the pill work its magic. The man finally recovered and opened his eyes again.
“Thank you for your help my kind sir.” The man said with a smile as he tipped an invisible hat in Ian’s direction. “You could have made your getaway while I was in trouble down there.” The man pointed out.
“It looks like you needed my help Sir, and that is more important than whether or not you call the police and have me arrested for breaking in to your house.” Ian said with some pride in his voice over what he chose to do. “Is there anything else you need me to do for you?” Ian asked.
“Sit and talk for a while?” The man asked looking more hopeful than ordering Ian to do it.
Ian looked behind him and saw a sofa, so he sat down on it and waited to find out what this man wanted to talk about.
They both sat looking at each other for a couple of minutes before the man finally spoke. “Care to tell me about the thing with the dress down in the basement?”
Ian opened and closed his moth a half dozen times trying to work out how to explain what the man caught him doing, but he was drawing a blank, so he just let out a sigh as his head dropped in shame. “I can’t explain it Sir.”
“Is it all female clothes you like, or do you just like Maid’s uniforms?” The man asked with a smile. “And please call me Richard.” The man added.
“I like all forms of female dress, but Maid’s uniforms are my favourite.” Ian said before he could stop himself. He slapped a hand over his mouth when he realised what he’d said.
“Don’t look so worried.” Richard chuckled, but Ian thought it was more like a giggle than a chuckle. “You can already see that I like Maid’s uniforms.” He added with a grin.
“All those dresses are yours?” Ian asked looking shocked that this man would just admit it to him so easily.
“Yes, I use to play maid to my mistress, but I was retired after I was found to have a heart problem.” Richard admitted with a sad sounding sigh.
“Mistress...?” Ian stuttered out nervously as he looked around like she would come bursting into the room looking to punish him for what he did with the others.
“Don’t worry, I live here alone, but this house is owned by my mistress.” Richard smiled. “Do you have a name?” He asked.
“Well thank you for your help Ian.” Richard said with a bow of his head. “You’re free to leave whenever you want, and I won’t be calling the police on you, not after you saved my life.” Richard smirked when he saw that Ian had some questions he wanted to ask.
“Will you be alright if I leave though? Don’t you have anyone to look after you?” Ian asked sounding worried.
“My mistress has tried to hire people to look after me, but I didn’t get on with any of them.” Richard frowned. “Mistress and her new maid call in a couple of times a week to check on me, and she calls every day to make sure I’m fine.” Richard added with a smile. “You’re not looking for a job are you?” he asked.
“I’m only thirteen, and my parents would never let me get a job anyway.” Ian admitted with a sad look as he could just see himself looking after Richard while wearing one of those maid’s uniforms, minus all the restraints.
“Don’t think of it as a job, but more of a friendship with benefits.” Richard smiled. “You come over to keep me company, and I’ll help you become a better maid.”
“You’d let me wear those uniforms?” Ian asked sounding a little too excited as he pointed down towards the floor to where the boxes were.
“Yes I’ll teach you what I know about being a maid, and I’ll also help you explore your feminine side.” Richard offered.
“I’m not sure I want to be locked up though.” Ian said nervously.
“I don’t plan to use any of that stuff on you, that was just another little love of mine, and my mistress liked to make sure I wouldn’t run away.” Richard chuckled, or giggled as that is what Ian heard when Richard laughed. “Bondage isn’t for everyone, and I don’t want people to get the wrong idea about me.” He added with a raised eyebrow.
Ian giggled as he thought about that statement and just how Richard was willing to help him become a better maid, but didn’t want to warp his mind by putting him in bondage. Part of him was a little sad to hear that he wouldn’t be locked up while playing at being Richard’s maid, but he hoped that one day he might get to find out what it’s like to be controlled by a strict master or mistress.
“I think I should finally call in a handyman to fix the locks on that basement doors as well.” Richard said snapping Ian out of his daydreams. “We don’t want your friends wandering into the house while you’re playing my maid.”
“There not really my friends, I’ve only just met them.” Ian explained and then went on to tell Richard about his parents just moving into the area and how he was just hoping to make more friends here than he had at his old home.
“I know how you feel when it comes to friends and the fact you feel different to the other boys because you have a softer side that wants to get out.” Richard said with a sigh as he remembered feeling alone at Ian’s age.
“How did you find a mistress to work for?” Ian asked.
“She found me sort of.” Richard chuckled in his own special way again as he looked to be remembering something. “My mistress is actually my older sister by two years.” Richard added and then waited to see how Ian would react to that.
“Your sister is your mistress?” Ian asked not quite believing what he was hearing. “Did she not like you or something?” He asked.
“No, nothing like that, in fact we have a very close bond to each other.” Richard smiled. “My father tried to groom me to take over the family business, but I just wasn’t cut out for it, then he and my mother were killed, and I was thrown in at the deep end and would have drowned if not for Anne, my sister. She was born to run the company.” Richard added with pride.
“But how did you end up becoming her maid?”
“She found me in my father’s study one evening with a bottle of whisky and a large bottle of pills, and I finally opened up to her about wanting to be a maid and how I wished I could find a mistress to take control of my life.” Richard explained. “She stepped up to the plate and took over the running of the company and hired me on as her maid, and then she would lock me in the uniform and tell me I couldn’t have any of it removed until my work was done for the day.” Richard smiled as he had fond memories.
“Why did she retire you then if she’s your sister as well as your mistress?” Ian asked.
“We found out I had a heart problem, and she was worried that if I kept working that I would end up killing myself even quicker.” Richard admitted with a sigh. “I do miss playing at being her maid, but hopefully I can live again through you.” He added with a grin.
“When can I start?” Ian asked, not needing anymore time to think about any of it.
“You can start by bringing up all the boxes marked with a colour and the letter ‘M’ after it.” Richard said as he rose to his feet and started walking Ian back towards the door to the basement. “Once you’ve brought them all up, then I’ll show you up to a bedroom you can use to change in when you arrive here each time.”
Ian was soon running up and down to the basement to collect all the boxes. It turned out that Richard had a maid’s uniform in just about every colour of the rainbow and a couple that weren’t even part of the rainbow.
Richard showed Ian to a bedroom on the first floor of the large house and Ian then took all the boxes up to that room and started removing the dresses and other items from the boxes and putting them in the wardrobe.
Once all the dresses and shoes were in their new home, Richard had Ian take all the boxes back down to the basement, still with all the other restraints still in them.
“Can I try something on now?” Ian asked looking hopeful.
“It’s getting late, and I don’t want your parents to worry, so I think its best you get off home now and we can have a fresh start on your training tomorrow.” Richard said as he walked Ian back down to the basement where he’d left his skateboard.
Ian had just broken up for the six weeks holidays, so he’d have plenty of time to let Richard train him, or more to the point Isabella to be the perfect maid.
Chapter Two: First day on the job.
Ian had kept all the stuff about meeting Richard and the stupid stunt that led up to it, from his parents the evening before, and as far as his mother knew, Ian was just going out to hang with his new friends, but really he was off over to begin his training to become a better maid. He used his bike so he could get over to Richard’s house quicker and get started.
There was a van parked up outside the house when Ian arrived, so he rang the bell and then waited for Richard to answer it. He didn’t have to wait long before he saw him open the door. Richard had already let him in the main gate at the end of the long driveway after Ian had pushed a button on an intercom mounted to the wall next to the gate, and let Richard know he was there.
“Hello Ian, please come in, and for future use, please use the back door, I’ll give you a key so you can let yourself in.” Richard informed Ian as he led him up to the bedroom they had placed all the uniforms in the day before. “I’ll leave you to make a start on getting dressed while I go and finish up with the handyman down in the basement. I’ve finally gotten around to having those broken locks fixed.” Richard added with a grin just before he left the room.
Ian had been excited about trying on some of the PVC maid’s dresses, but now the time had come, he was scared as he’d never actually been dressed in front of anyone before, and he didn’t know this Richard at all really. Ian walked over to the closet and opened the door and just stood looking at all the different coloured maid’s dresses for a couple of minutes. His worries were soon pushed aside by his need to feel what it felt like to wear one of the dresses.
He stripped out of all his clothes and then he pulled out his panties and bra that he’d placed in his jacket pocket before leaving the house and he set to work turning himself into Isabella the maid.
Richard had shown Ian were to find clean pantyhose and frilly white panties to wear over them, so he got a pair of black pantyhose out and a pair of panties to wear over them and he sat on the edge of the bed to slip them on his legs.
Once he was in his own panties and bra and the pantyhose and frilly panties, he walked over to the closet and picked out a dress to wear. He went for the pink one because it looked the most girly one in the collection. It was a little big on him, but Richard wasn’t a large man, so it didn’t look to bad.
The maid’s dress came all the way up to his throat at the front and it zipped up at the back all the way to his neck, so he didn’t have to worry about flashing his breasts at anyone, not that he had any to flash in the first place. Ian did wish he’d used some extra padding to make him look bigger now he had the dress on though, as he looked at himself in the mirror and saw how lose the dress looked in the chest area. He realised that Richard must have used a much larger set of breast forms when he use to wear these dresses.
Another little detail that Ian hadn’t noticed the day before when he was looking at the dresses down in the basement was the fact they all had frilly panties sown into them, so if Richard locked the dress on him, Ian would be stuck until Richard released him again. He wouldn’t be able to get out of the dress by slipping it over his head, not that he’d be able to anyway without tight the dress fit around his neck. Ian realised that going to the bathroom wouldn’t be possible without asking permission either.
Ian was dancing around as he tried to zip up the dress when he heard a giggle from the doorway. He spun around to find Richard stood there looking at him struggling. Ian froze in fear, but relaxed when he saw that Richard wasn’t making fun of him, but just laughing at how silly he looked trying to zip up the pink maid’s uniform.
“Here, let me help you.” Richard said with a smile as he walked across to where Ian was stood and helped to zip up the dress. “I think you need to grow a little more before the dress will fit you properly.” He commented as he finished zipping Ian into the dress and then Ian heard a click.
“What have you just done?” Ian asked as he reached up and felt the back of the dress where the zip ends and found a small padlock. He felt both fear and a thrill run through him as he realised that he was now stuck in the dress until Richard let him out of it.
“I’ve just locked you into it until you’ve carried out your duties to my satisfaction maid.” Richard said in a strict tone as he walked over to the closet and returned with a pair of pink heels to match the dress Ian was now locked into. “Place these on your feet; I have jobs for you to do.” Richard added looking sternly at Ian.
“Okay.” Ian stuttered out nervously as he took the pink high heeled shoes from Richard.
Richard wouldn’t let go of the shoes as he looked at Ian with a frown. “You should reply with a yes sir or yes ma’am.” Richard informed him.
“Sorry Sir.” Ian stammered out.
“Don’t look so worried my poor child.” Richard smiled. “This is all meant to be fun for you.” Richard added as he finally let Ian take the shoes from him.
Ian smiled back just before he made his way over to the bed and sat down to place the shoes on his feet. Ian was shocked to find that the heels fit him perfectly, but one look at Richard told him that Richard had really small feet, not that Richard was a large man anyway.
Once he had the shoes on, Ian rose to his feet again and felt a little wobbly on the high heels due to them being much taller than anything his mother owned, and they also had a one inch platform sole to them. Ian felt a foot taller now he was stood up.
Ian watched nervously as Richard walked over to him and then crouched down as he pulled something out his trouser pocket. Ian soon realised what it was as he heard a click as Richard did something with his left ankle, and then he heard another click as he did the same thing with his right ankle. Ian knew he was now locked into the high heels, just like he was the dress.
“You will let me out of these things at the end of the day Sir?” Ian asked sounding more nervous than ever now.
“Yes, but only if you get all the cleaning done.” Richard smirked.
Ian found himself hoping that Richard didn’t want him to do too much in these heels, as he wasn’t sure he’d be able to until he’d practiced walking in them a lot more. Ian was soon looking even more worried as Richard placed a hand on his back and started leading him out of the room.
“I can’t go down stairs looking like this Richard...” Ian said in a panic as he tried to worm his way free of Richards hand on his back. “That handyman will see me.” Ian added.
“Firstly the handyman has already left, and secondly, what did I say about calling me Sir or ma’am?” Richard asked with a frown. “I will have to think of a suitable punishment for you now.” He added with a troubled sigh before he started walking again, pushing Ian along with him.
“I’m sorry Sir, but I was scared and just forgot.” Ian said, hoping to make Richard change his mind about the punishment.
“A good maid always does as she’s told without question; this is something you will learn before we’ve finished your training.” Richard said as they made their way down the stairs. Richard did help Ian to make his way down though while he got use to the high heels. “What is your name anyway?” Richard asked as they made their way down.
“It’s Ian Sir.”
“You don’t look much like an Ian to me right now.” Richard smirked. “You must have a female name you like to use when you’re dressed as a girl.”
“I think of myself as Isabella at home when I dress up.” Ian blushed. “Sir...” He quickly added looking worried again.
“It’s nice to meet you Isabella, now let us get you to work, so I can see just how bad you truly are.”
Isabella soon found herself in the kitchen facing a large cupboard full of plates and dishes of all shapes and sizes.
“Place this piny on to keep your uniform clean and then I want you to put on these rubber gloves and set to work washing and drying all these by hand.” Richard ordered. “I’ll be back to check on you later.” He added just before he left the room again.
Isabella just looked at the large cupboard and then at Richard as he left the kitchen without looking back. Not seeing as she had a choice, Isabella set to work filling the sink with hot water while she started clearing out the cupboard.
Isabella had been working for some time and was nearly half way through the cupboard when she heard the sound of heels on the marble floor, so she turned around looking worried as to whom the heels belonged to. She saw a blonde haired woman in a figure hugging red leather dress enter the kitchen. Isabella thought the woman looked amazingly beautiful in the red dress with the long pencil skirt that ended just above the knee and was so tight that the woman had to take very small steps. The woman’s long legs carried on down to a pair of red high heels and her legs were wrapped in black pantyhose or stockings. Isabella could also see that the woman had a very impressive set of breasts trying to escape out the space at the top of the red leather dress. Isabella had become so engrossed in how beautiful this woman was, that she’d forgotten all about being worried about another person seeing her dressed this way.
“Hello Isabella. I trust you like what you see?” The woman asked in a posh sounding voice with an edge of sternness to it.
“Yes ma’am.” Isabella stuttered out. “But where is Richard?” She asked nervously as she suddenly remembered how she was dressed and the fact that Richard had the keys to her shoes and dress.
“Master Richard had to go out, but he left me with your keys.” The woman smiled a wicked smile as she pulled at a chain she had hanging around her neck to pull the end out from between her breasts to reveal a set of keys hanging on the end of it. “You may call me Mistress Rachel.” The woman added in a dry tone. “Now get back to work while I sort out your punishment for disobeying Master Richard earlier.” Rachel said as she spun on her heels and left the kitchen again with such grace and ease that made it look like she’d been wearing heels all her life.
Isabella was eager to find out more about this mystery woman, but at the same time she was worried about the punishment she’d already earned and didn’t want to add to it by not getting the dishes washed, dried and put away again fast enough, so she got stuck in again hoping to show this Mistress Rachel that she was a good maid and didn’t deserve to be punished.
“Good, you’ve finally finished Mistress Rachel said a little later making Isabella jump as she was placing the last cup and saucer back in the cupboard. Isabella let out a sigh, glad she hadn’t dropped them, she knew that would have earned her a bigger punishment. “Take the piny off and follow me so we can get your punishment out the way.” Mistress added in a bored tone as she turned around and left the kitchen again, not looking back to see if Isabella was following her or not.
Isabella followed the woman into a large room that was actually a library. She couldn’t help checking out the woman’s nice round ass as it swung from side to side due to the high heels and the tight pencil skirt forcing her to take lots of little steps.
“Lean over this chair and grip the sides of the seat with both hands.” Mistress Rachel ordered in a stern voice as she pointed to a chair in the middle of the room.
Isabella looked at Mistress Rachel for a second, but soon did as she was told when she remembered what Richard had said earlier about doing as she was sold, and the fact that it was not doing as she was told that got her into this mess to begin with.
She was soon bent over the chair looking very nervous as she waited to find out what her punishment was to be. She had a pretty good idea when she felt Mistress Rachel lift up Isabella’s skirt to give her a clear shot at her backside.
‘Crap...! She’s going to spank my backside...!’ Ian thought to himself, but kept still and never spoke out against it.
“Good, you can do as you’re told.” Mistress Rachel said as she walked around Isabella. “Do you think you should be punished for not trusting in your master?” She asked.
Ian wanted to scream out no, but the part that was Isabella thought she should have trusted Richard earlier, so yes she did deserve to be punished for it.
“Well I’m waiting for an answer Maid...” Mistress Rachel said with a snarl. “I don’t like to be kept waiting Isabella.” She added as she stroked one of her long red nails across Isabella’s frilly panties.
“Yes Mistress Rachel, I do think I should be punished for not trusting in Master Richard.” Isabella said.
“Good; and what do you think that punishment should be...?” Mistress asked as she ran her red clawed nail back the other way.
“It’s not the maid’s place to dictate what punishment she’s earned Mistress Rachel.” Isabella said, hoping that it was the right thing to say.
“Very good my child, you are a natural submissive, and you know your place.” Mistress said with a giggle.
Isabella turned her head to get a better look at Mistress Rachel when she heard her giggle because she knew that giggle; it was the same sound Richard made when he laughed at something. Isabella thought it might be the fact that this woman was Richard’s sister, but Isabella already knew that Richard’s sister was called Anne, but the name Rachel could just be made up.
“It looks like the penny has finally dropped.” Mistress smiled as she saw the look in Isabella’s eyes as she looked at her.
“Master Richard...?” Isabella asked.
“Most of the time, but every now and then I still like to play dress up, but I’ve never had a maid of my own to boss around.” Mistress Rachel said, but it was Richard’s voice Isabella heard speaking.
“You look so different, and those breasts look real.” Isabella said as she tried to get a better look, but she was still leaning over the chair and holding either side of the seat.
“They’re just made out of latex and the choker around my throat hides the edge of them.” Mistress Rachel said with a smile as she cupped one of them in her left hand. “You can stand up again now Bella, I’m not really going to punish you, I just wanted to give you a taste of what my Mistress use to do to me.” She explained.
Isabella still saw Richard as Mistress Rachel, because she sure didn’t look like a Richard at the minute. Isabella couldn’t stop checking Mistress Rachel out. Her hair, makeup, and figure all screamed female.
“Do you think I could look as good as you do one day?” Isabella asked in wonder of the woman Richard had turned himself into.
“You already look really good Bella, but with a little makeup and some padding out in the right places, and you will look better than most girls your age.” Richard said using his female voice again.
“I’ve never worn makeup before.” Isabella said nervously.
“Do you want me to teach you?” Mistress Rachel asked. “We’d have to buy you some though, as it’s not advisable to share your makeup with others.” She added.
“Yes please and how do you get your voice to change like that?” Isabella asked.
“Mistress got me some tapes and made me practice until I could pass out in public so we could go shopping together.” Rachel explained.
“Why don’t you dress all the time if you can look like this?” Isabella asked. “If I could look as good as you, I’d always be dressed as a girl.” She admitted.
“But you could pass as a girl right now, and as for the voice, you’ve been speaking like a girl since you first put that dress on.” Rachel pointed out with a grin. “As for me dressing all the time, I just do it for fun, and I have to be careful how much excitement I get due to my bad ticker.” Rachel added with a sigh as she tapped her chest where her heart was.
Isabella went to argue, but realised that she had dropped into the role of a female since putting the dress on, she’d even got use to the heels now, even if they were making her feet ache still.
“I just feel more like myself when I’m Isabella.” She finally admitted.
“Have you tried talking to your parents about this side of you?” Rachel asked as she led Isabella over to a sofa and helped her to sit down before taking a seat herself.
Isabella watched as Rachel sat straight backed which made her chest stick out even more due to the corset she was wearing under the red leather dress. Isabella knew she was wearing a corset because there was no way Mistress could get a waist that small without one.
“I already know my parents would never understand this side of me.” Isabella sighed. “My father would beat me to death if he ever saw me dressed like this.” She added with a shudder at the thought of her father seeing her like she was now dressed in a bright pink PVC maid’s uniform and pink high heels.
“I will help you explore this side of your nature then Bella, but from what I’ve seen, one day you will have to come clean with them, or break off all contact.” Rachel pointed out.
“Why would I have to break off all contact with them?” Isabella asked looking puzzled.
“You were born to be a maid, and I can’t see your parents wanting anything to do with you once they find out what you will be choosing to do for a living, and how you will one day be living as a woman while serving a Mistress or a Master.” Rachel smiled.
“You’ve worked all that out from just watching me this afternoon?”
“As Ian you are quiet and scared of your own shadow, but as Bella you come alive and love moving around in that dress, as I expect you will in any form of female dress.” Rachel giggled. “I wanted to see how you coped this afternoon before I started teaching you properly, so starting tomorrow I will help you dress properly and how to act as a maid should.”
“Will it be you Mistress Rachel, or will it be Master Richard?”
“Which would you rather be taught by?” Rachel asked with a smirk, like she already knew the answer to that question.
“I’d like you to teach me Mistress Rachel.” Isabella grinned. “I think you look happier than Master Richard does as well.” She pointed out as she looked at the beautiful woman sat next to her with a smile on her face.
“It has been a fun afternoon watching you work in the kitchen and having a reason to get dressed up again.” Rachel admitted as she placed her red clawed hand on top of Isabella’s.
Isabella noticed that the long red nails Mistress had on her hands made them look much more feminine.
“As your maid done enough to earn her release so she can get home?” Isabella asked when she saw the time was getting on and Ian’s mother would be wondering where he was.
“Yes she has done an exceptional job for her first day as my maid, and as earned her release.” Rachel giggled as she pulled out the chain with the keys on and released the locks on the back of the dress and the shoes before she walked with Isabella back up to the bedroom where Ian’s clothes were.
Ian was soon back and looked a little sad to be a boy again. Richard was still dressed as Rachel as she walked Ian to the front door where he’d left his bike when he arrived earlier in the day.
“I wish I could stay here as your maid and never have to become a boy again.” Ian sighed as he looked down at his dull male clothes.
“Once you’ve done with school, and you can venture out into the big wide world, you’ll be able to dress as you please.” Rachel said as she pulled Ian into a hug.
“Will you let me work for you as your maid?” Ian asked looking hopeful.
“We’ll have to wait and see.” Rachel said with a forced smile.
Richard would like nothing more than to make that promise, but he already knew he was living on borrowed time and he would be dead long before Ian ever finished school. He had already decided to call his sister and let her know about the troubled boy he’d found, and also how Rachel had stepped into the realm of playing Mistress now. Richard thought that Anne would be able to offer some help with getting Isabella some makeup and other items she will need as well.
“I’ll be over first thing in the morning so I can spend the whole day as your maid.” Ian said looking a little happier about that.
“I better make up a list of things that you can do then, and I will be punishing you tomorrow if you don’t do as you’re told.” Rachel warned, but she was smiling, so Ian didn’t look too worried about her warning.
“I promise to do as I’m told Mistress Rachel.” Ian grinned just before he got on his bike and peddled off down the long drive as he looked back and waved to the red leather clad woman stood waving back at him with a smile on her face.
Ian couldn’t wait for tomorrow to arrive so he could once again become Isabella, Mistress Rachel’s maid. Ian’s smile faded when he saw Dean and the others hanging out on a street corner, but he just blanked them as he rode past. Simon shouted him over, but Ian just took no notice and kept going. Ian had already made his mind up, and he didn’t want friends if they were going to be like Peter and Dean, no he was going to be a maid one day, and none of them would understand his reasons for wanting to do that, so it was better to keep to himself.
To Be Continued Next Tuesday
Story by SaraUK
Edited and Posted by SamanthaK
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