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Sentenced To Life

Author: 

  • Sara UK

Organizational: 

  • Title Page

Audience Rating: 

  • Mature Subjects (pg15)


 © January 2013

Sentenced To Life Part 01

Author: 

  • Sara UK

Audience Rating: 

  • Restricted Audience (r)

Publication: 

  • Fiction
  • 17,500 < Novella < 40,000 words

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Crime / Punishment
  • Caught with Consequences
  • Femdom / Humiliation
  • Physically Forced

TG Elements: 

  • CAUTION
  • Maids / French Maids / Servants

Permission: 

  • Posted by author(s)


 © January 2013


Part One

     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.

     “Ian, Sir.”

     “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

    EDITORS NOTE: Please Comment and/or leave Kudos and let Sara know you like her work please, Any comments on spelling, grammar or the layout of the story please PM me “Samanthak” not Sara. Thank you

Sentenced To Life Part 02

Author: 

  • Sara UK

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Fiction
  • Novel Chapter
  • 17,500 < Novella < 40,000 words

Genre: 

  • Transgender

Character Age: 

  • Teenage or High School

TG Themes: 

  • Crime / Punishment
  • Caught with Consequences

TG Elements: 

  • Dominance & Submission / Bondage
  • Maids / French Maids / Servants

Permission: 

  • Posted by author(s)


 © January 2013


Part Two


Chapter Three: Meeting Mistress Anne.

    Ian was up and dressed early the next morning, he was eager to get over to Mistress Rachel’s and start playing her maid again.

     “You’re up early sweetie.” His mother said as he was putting his trainers on at the back door.

     “I’ve got a lot of things to get done today mum, so I wanted to get an early start.” Ian said happily. “I’ll see you later...!” He shouted as he jumped on his bike and peddled off down the driveway.

    Ian wasn’t a very good liar, so he didn’t want to say too much to his mother and risk her finding out more than he wanted her to know.

    He was soon at the main entrance to Mistress Rachel’s home and he pushed the button on the intercom to let her know he was there so she could let him into the grounds through the large iron gates that stopped most people gaining access to the grounds. Dean and the others had still managed to get in though by going over a wall.

     “Hello...?” A voice asked out a speaker just above the button Ian had just pressed.

     “Hello Mistress Rachel, its Ian.” He said into the speaker. There was a keypad so he could let himself in if he knew the code, but he didn’t, so he had to ask Mistress for permission to enter.

     “I’ll let you in.” The voice said just before the gates started to open.

    Ian entered the grounds and then watched as the gates started to close again. Ian thought there must be some cameras around for Mistress to know when he had entered the grounds so she could close the gates again.

    He made his way up to the house and smiled when he saw Mistress Rachel stood at the front door dressed in a black leather dress today that looked identical to the red one except for it being black. Mistress Rachel looked just as stunning as she had the day before. Ian still found it hard to believe that this woman was also the man called Richard he’d first met the other day. Everything about this woman said female.

     “Remind me to give you a code for the gate before you leave today.” Rachel said as she walked Ian into the house. “It isn’t proper for the Mistress of the house to be answering the door to the help.” She added in a posh voice.

    I thought you wanted me to use the back door to enter the house as well Mistress Rachel?” Ian asked as they made their way through the house.

     “You can, starting tomorrow, but I decided to meet you at the front door today instead.” Rachel smiled. “The mistress of the house can do that you know, change her mind.” She added.

    Rachel led the way up to the bedroom where all the maid’s uniforms were and Ian let out a gasp when he saw what was laying on the bed waiting for him. There was a black maid’s uniform laid out on the bed, but the biggest shock for Ian was the fact there was a set of what looked like female breasts laying on the bed next to the uniform.

     “I’m going to have breasts today?” Ian asked as he walked over and squeezed one of the breasts and was shocked at just how real it felt, well real to Ian as he’d never actually felt a real breast before.

     “Yes, you will always wear them when you’re my maid from now on.” Rachel said in a dry tone that made her sound bored. “Now get dressed.” She added.

    Ian picked up the breasts which actually looked a little like a bra, but he wouldn’t need to wear a bra to keep them supported. They even had semi erect nipples that he knew would show through the maid’s uniform.

     “Well don’t just stand their child.” Rachel said sounding annoyed. “You have a busy day ahead of you, and you can’t be my maid looking like that.” She added just before she turned around and left the room so Ian could become Isabella the maid.

    Ian was soon out of his clothes and starting to get dressed in all the items on the bed. He slipped on the panties he found laying on the bed and then he sat on the edge of the bed to put on the pantyhose. There were no frilly panties for him to wear today, but there was a pair already sown into the dress to stop him being able to get the maid’s dress off over his head as he’d found out the day before.

    Once he had the pantyhose on, he then set to work putting on the breast bra as he thought of it. He was shocked to find out that they were weighted like real breast and he loved the way it looked once he had it on. He couldn’t help himself as he started bouncing up and down just so he could watch them move around.

     “I hope they’re not going to be a constant distraction for you...?” Mistress Rachel asked from the doorway.

     “No Mistress, sorry Mistress.” Ian said sounding more like Isabella now he had large breasts of his own.

    He picked up the maid’s dress and pulled down the long zip at the back before he stepped into it and then pulled it up and slipped his arms through the puffy sleeves and then he tried to close the zip at the back, but he was soon being helped by Mistress Rachel who added the padlock again once the dress was on. Ian was puzzled at just how well this dress seemed to fit him compared to the pink one he’d worn the day before, but the biggest shock was when he looked down at his chest and noticed the fact he could see his breasts through a heart shaped cut out in the front of the dress that let everyone see a nice amount of cleavage. It actually looked like he had real breasts, or Isabella did, as he didn’t look like a boy called Ian anymore with a chest this big.

     “Why does this dress fit better than the one I wore yesterday, and why does this one have the cut out to reveal my new breasts?” Isabella asked.

     “You just asked me two questions, but not once did I hear you call me Mistress Rachel, and you never asked for permission to ask me any questions in the first place.” Mistress Rachel said in a quiet tone that made her sound very angry with Isabella.

     “I’m sorry Mistress Rachel, but I didn’t know I had to ask permission first.” Isabella said in a timed voice. “Please forgive me Mistress Rachel.” She added in a more pleading tone.

     “My sweet child you will soon learn that you cannot be given forgiveness for making a mistake, you must earn it by being punished.” Mistress Rachel said in a sweet tone as she walked Isabella over to the bed and then Mistress sat down before taking Isabella across her knee and lifting up the skirt and petticoats on the maid’s dress so she could spank Isabella’s bottom for her.

    Isabella was shaking as she lay across Mistress’s lap waiting to be spanked. Ian had never been spanked before, but his father had taken a belt to his backside a couple of times when he’d done something to earn it, but this was a first for Ian or Isabella as he was at the minute.

     “I want you to count out each spank and then thank me for teaching you to be a good maid.” Mistress explained as she got ready to strike the first blow.

     “One...! Thank you Mistress Rachel for teaching me to be a better maid.” Isabella shouted out. The blow was more of a shock than it actually hurting very much.

     “I was going to give you four more spanks, but now you’ve just earned yourself another five for not listening to what I said.” Mistress sighed. “I told you to say good maid, not a better maid.” She pointed out Isabella’s mistake. “Let us start again.” She added as she got ready to begin again.

     “One...! Thank you Mistress Rachel for teaching me to be a good maid.” Isabella made sure to say it right this time.

    Mistress Rachel spanked Isabella nine more times and Isabella shouted out the number and the same thank you after each blow, and even though Mistress wasn’t hitting her very hard, it was still beginning to hurt by the time she called out thank you after the tenth slap.

     “I trust you will remember to ask for permission to speak in future Maid Bella?” Mistress asked as she helped Isabella to stand again.

     “Yes Mistress Rachel and I am sorry for causing you to punish me.” Isabella said as she tried to rub the pain away.

     “I’m sure you will make lots of mistakes, and I will have to keep punishing you, but I think I will have to find something to strike you with, as it was rather painful on my hand doing that.

    Isabella thought she should try being on the receiving end if she wanted to know what pain was, but then she remembered that Mistress was once a maid as well, so she would already know how it felt to be spanked, so she decided to shut up and try not to earn another punishment.

     “Unless you want me to punish you for not being dressed correctly, I would suggest you get your shoes on so I can get you to work cleaning the house.” Mistress said as she looked at the pair of black heels at the side of the bed.

     “Yes Mistress Rachel, sorry Mistress Rachel.” Isabella said as she sat on the edge of the bed before she remembered to be more careful. She let out a small squeal of pain before she quickly recovered her composure and set to work putting on the shoes.

    Rachel had to look away as she tried not to giggle at the noise Isabella just made, but she soon recovered her composure and got Isabella to lift up each foot so she could add a padlock to stop her removing the shoes until her duties were done for the day.

     “Thank you Mistress Rachel.” Isabella said when Rachel had finished adding the second lock.

    Rachel liked the way Isabella was so eager to please and she already knew she would make someone a wonderful submissive maid one day.

     “You are most welcome Bella, now follow me and I will get you to work.” Rachel said as she turned and left the bedroom with Isabella following close behind. The sound of their heels made sweet music on the marble floor as they moved across the landing and then down the stairs to the kitchen where there were some dishes left over from breakfast.

    If Isabella hadn’t been so eager to please her mistress, she might have noticed that there were dishes for more than one person, but Isabella was too focused on getting her job done to notice.

     “Come and find me in the library when you’ve finished cleaning the kitchen, and I’ll sort you out with your next task.” Mistress said before she turned and left the kitchen again.

    Isabella got her piny and rubber gloves on before she set to work washing the dishes and cleaning the kitchen. She was enjoying herself as she moved around the kitchen humming to herself while she worked. She did finally notice the extra dishes, but just thought they might have been from the evening before, so she pushed the thought from her head as she focused on doing the best job she could and hoped to show her mistress she was a good maid.

    Once the kitchen was spotless, Isabella removed her piny and then tried to look herself over, but had trouble seeing past the large breasts she now had. She’d had trouble working with them stuck out like they did to begin with, but now she felt like she’d had them all her life and found herself wishing she had, she loved the way they bounced up and down every time she moved. Add to that the click of the heels on the marble floor, and Isabella was in heaven right now.

    Isabella made her way into the library to let Mistress Rachel know she was finished in the kitchen and to find out what job she wanted her to do next.

    She saw Mistress was reading the paper, so she made her way over. “I’ve finished in the kitchen Mistress Rachel, what do you want me to do next?” Isabella asked.

     “Firstly I’m Mistress Anne, and secondly you should never speak before being given permission to.” This new Mistress said as she closed the paper up and placed in on the table next to her seat.

    Isabella looked nervous all of a sudden when she saw this new woman. She looked a lot like Mistress Rachel, but unlike Mistress Rachel, this woman radiated power and she had a look of a true Mistress. Isabella found it hard to look this woman in the eyes and had to look away.

     “I’m sorry for my mistake Mistress Anne.” Isabella said as she recovered herself and hoped that her little slip hadn’t just earned her another punishment.

     “I will let you off this once, as I already know that my sister didn’t inform you that I was here.” Mistress Anne said as she looked Isabella up and down. “You are a pretty little thing aren’t you?” Mistress Anne added with a raised eyebrow.

     “Thank you Mistress Anne.” Isabella said as she tried to do a little curtsy.

     “Well I see what you can do next.” Mistress Anne said after seeing the poor excuse for a curtsy Isabella just did. “You can stand and practice your curtsy until you can do it perfectly.” She added.

     “I’m sorry Mistress Anne, but I don’t know any other way to do a curtsy.” Isabella said nervously as she could see another spanking coming her way. “If you could show me, then I would be able to perform it properly.” Isabella added.

     “Do I look like a maid that would spend time showing you how to curtsy?!” Mistress Anne snapped as she rose to her feet and looked Isabella in the eyes.

     “I’m sorry mistress Anne.” Isabella chocked out as she found herself unable to look this woman in the eyes.

     “Rebecca...!” Mistress Anne called out and then waited.

    There was soon the sound of heels on the floor as another maid entered the library. “Yes Mistress Anne?” She asked.

     “Rebecca I need you to spend some time teaching this girl how to do a proper curtsy.” Mistress Anne said as she pointed at Isabella.

    Isabella thought this new maid might be Richard, but that was soon proved to not be the case when she saw Mistress Rachel enter the library with a tray of drinks for herself and Mistress Anne.

     “You have a lot to learn about being a mistress sister.” Mistress Anne frowned when she saw Rachel carrying the tray.

     “Rebecca was about to bring it in when you called to her.” Rachel explained as she placed the tray on the table and then offered Anne one of the cups that were sat on it.

     “You could have called her back.” Anne said in a matter of fact way as she took the offered drink from Rachel.

     “I didn’t want to get her in trouble, and I know how you hate to be kept waiting.” Rachel pointed out as she sat down before picking up her own drink.

     “You know me to well sister dear.” Anne smiled before taking a sip from her cup of tea. “Well Rebecca, don’t just stand there, show the girl how to do a proper curtsy.” Anne said after placing the cup back on the saucer.

     “Yes Mistress Anne.” Rebecca said as she dipped a curtsy in Anne’s direction.

    Isabella watched what Rebecca did, but she was distracted by the fact that this woman was dressed just like her, and Isabella found herself wondering if Rebecca was also male or a real girl.

     “Did you see how I did that Bella?” Rebecca asked snapping Isabella out of her thoughts.

     “I’m sorry Miss Rebecca, but I missed it.” Isabella said nervously.

     “Not very observant is she.” Mistress Anne said to Rachel.

     “Don’t be so hard on the child; it is just her second day on the job.” Rachel defended Isabella.

     “It would be her last if she was mine.” Anne grumbled before taking another sip from her cup.

    Isabella was getting more and more nervous with every passing second in the company of Mistress Anne, but she wasn’t going to quit.

     “Watch what I do and then you try it.” Rebecca said taking no notice of what Anne and Rachel were talking about.

    Isabella watched more closely this time and then she copied it. Rebecca had her do it again and again and again until it was second nature for Isabella to curtsy, but her legs were aching from all the bending she’d been doing.

    By the time Rebecca was happy with Isabella’s curtsy, Anna and Rachel had finished their drinks, so the two maids were told to clear the things away and make a start on lunch, so Rebecca looked at Isabella as if to say I outrank you, so you get to take the tray away.

    Isabella stepped over and dropped a curtsy to the two mistress’s before she picked up the tray with the now empty cups and saucers on before she followed Rebecca out the library into a smaller kitchen area to wash and put away the cups. Isabella realised this is why she never saw Rebecca or Rachel earlier.

    Once they had cleaned and put the cups, saucers and other things away, or more to the point Isabella had while Rebecca watched her every move. They went into the larger kitchen to make a start on lunch. Isabella looked puzzled as Rebecca set to work grilling enough chicken for two while she had her set to work doing a couple of small garden salads to go with it.

     “The help doesn’t eat with the Mistress’s, we eat after them.” Rebecca said when she saw Isabella’s confused look.

     “I can see I have so much to learn about being a maid.” Isabella said with a sigh. “May I ask you a question Miss Rebecca?” Isabella asked nervously.

     “You can ask me anything when we’re alone Bella, and please just call me Rebecca, I don’t outrank you in anyway.” Rebecca smiled.

     “Are you a real girl, or is this just a part time thing that you do?” Isabella asked.

     “What is a real girl at the end of the day?” Rebecca asked with a grin. “I am neither a girl nor a boy, but something between the two these days.” She added.

     “Oh...” Isabella replied looking more confused now.

     “The breasts are real, but I still have my manhood.” Rebecca said in a whisper. “Mistress likes to have that handy when she’s had a stressful day.” She added with a grin.

     “You and Mistress Anne are also a couple?” Isabella asked looking a little surprised.

     “Yes we’re a married couple, but I live full time as a woman now and play maid whenever I get the chance, but most the time we’re just a happy looking lesbian couple.” Rebecca sighed.

     “I don’t think Mistress Anne likes me very much.” Isabella pouted.

     “She’s actually taken quite a shine to you, which is strange for Mistress Anne.” Rebecca admitted.

     “She likes me?” Isabella said looking shocked now. “I’d hate to see what she says to people she doesn’t like then.” She added with a frown.

     “Mistress Anne would never say this to you, well not before she gets to know you fully, but she’s so glad to see Rachel back and looking so happy again.” Rebecca started to explain. “Richard stopped dressing as Rachel when Anne had to force her to stop being her maid due to his bad heart, and he just lost interest in everything, but then Mistress Anne got a call from a very excited Rachel last night, so we came over early this morning to meet you.” Rebecca added with a grin.

     “I think both Mistress Ann and Mistress Rachel are very pretty.” Isabella admitted. “I wish I could be as pretty as them when I’m older.” She added with a sigh.

     “Am I not pretty then?” Rebecca asked with a pout.

     “Yes...! I think you’re very pretty.” Isabella stuttered out when she realised what she’d done. “I just didn’t want to embarrass you by saying so to your face.” She added in a pleading tone. “Please don’t be angry with me.”

     “I’m not angry with you.” Rebecca giggled.

     “Thank you for that Rebecca.” Isabella smiled.

     “Do you want to be a girl when you’re older then Bella?” Rebecca asked as they worked side by side getting the meal ready for the two mistresses.

     “I’m not sure, but I do feel happiest when I’m dressed as a girl, and it was a lot of fun doing the housework for Mistress Rachel yesterday.”

     “Are you not having as much fun today then?” Rebecca asked with a pout. “I’m sorry if I’ve seamed hard on you in the library, but Mistress Anne would have been much harder on you if she’d taken over.” Rebecca warned. “She once had me practice my curtsy all after noon until I was having trouble standing.” She warned.

     “She did? But I thought you said you were in love with each other?” Isabella asked looking confused again.

     “We are, but that still doesn’t stop Mistress from keeping me on my toes, and I wouldn’t expect anything less from her.” Rebecca smiled. “Now stop avoiding my question and tell me if you’re actually having any fun today?”

     “Yes I’m having fun today, but Mistress Anne just seems to scare me a lot more than Mistress Rachel.” Isabella admitted. “She just has a cold stare about her when she looks at me.”

     “That’s because Mistress Anne is a full time Dom and Mistress, not like Mistress Rachel who is just playing that part for you.” Rebecca explained. “Mistress Anne has other Dom’s send their slaves to her for training, and she’s never failed to train a slave yet. She even has other Dom’s treat her like we have to treat her.”

     “Slaves...?” Isabella asked nervously.

     “Yes, well they are mainly maids like you, but some are just kept as pets by their master’s and mistresses.” Rebecca shrugged.

     “I don’t want to be a slave, or a pet for that matter.” Isabella said as she had a vision of someone crawling around on all fours acting like a dog or a cat. “I just like being a maid.” Isabella tried to explain.

     “Then why did you let Mistress Rachel lock you in that dress and those shoes?” Rebecca asked.

     “I... I don’t know, but it kind of feels nice handing control over to Mistress Rachel.” Isabella shrugged.

     “Those are the feelings of a true submissive.” Rebecca smiled. “I love that feeling of not being in control and letting Mistress Anne tell me what to do.” She added with a grin.

     “And the two of you still love each other?” Isabella asked looking confused.

     “Yes we are very much in love, and have some amazing love making sessions after I’ve been punished for doing something wrong.” Rebecca smirked. “I sometimes do things wrong just so I get punished.” Rebecca added with a giggle.

     “I don’t feel anything like that when Mistress Rachel punishes me.” Isabella said.

     “You’re still too young for things like that sweetie, but I can already tell that you will become a wonderful maid one day.” Rebecca said with pride.

     “I hope it’s for a mistress, as I don’t want to be owned by a master.” Isabella said with a shudder as she thought about trying to keep a man happy while being their maid.

     “Some masters can be very good to work for, but like you I think being owned by a mistress is much better.” Rebecca agreed.

     “Were you ever owned by a master then?” Isabella asked.

     “Yes, but he wasn’t a very nice man, and I was rescued by Mistress Anne.” Rebecca started to explain. “He upset Mistress Anne and she bankrupted him and took me in payment, she later fell in love with me and made me her property through marriage.” Rebecca added with a loving sigh.

     “Were you like this when you married?” Isabella asked as she pointed at Rebecca’s breasts.

     “No, it was later when I had the operation to give me these puppies.” Rebecca said with a grin as she stuck her chest out even more. “I was spending all my time as Rebecca, so Mistress Anne paid for me to get these as an anniversary present.” She explained.

     “You’re so lucky to have found someone that’s so understands to your needs, and loves you for it.” Isabella said sounding jealous of Rebecca.

     “I’m sure you’ll find your way in life Bella, just enjoy being young.” Rebecca said as she gave Isabella a quick hug before they both got back to work making the lunch for their mistresses.

    Rebecca and Isabella finally got lunch finished and then they set the table in the dining room before they went to inform their mistresses that lunch was being served.

     “I thought that having you work with Isabella would speed things up, not take longer.” Mistress Anne said as she strolled past with Rachel at her side. Isabella couldn’t help looking at Rachel in amazement when she realised that her Mistress was really a man still. She looked just as beautiful as Mistress Anne.

    The two maids quickly sorted out their mistresses meals and then stood off to one side while they ate. Once they had finished and left again, Rebecca helped Isabella to clear the table and then she made them both a sandwich and warmed up a can of soup while Isabella set the table in the kitchen for them both.

    Once they had eaten and washed the dishes, they both reported back to the library where they found Mistress Anne and Mistress Rachel chatting and laughing with each other, that was until they saw the two maids enter the room.

     “Isabella...? Come here child, I have something for you.” Mistress Anne said looking very serious as she said it and pointed to a spot on the floor just in front of her.

    Isabella walked over as fast as she could, but looked really nervous about what Mistress Anne might have for her, but the thought of how Mistress Rachel had taken her across her knee that morning and spanked her, came to mind, and Isabella knew that getting spanked by this woman would hurt a lot more.

     “Yes Mistress Anne?” Isabella asked in a timid tone as she did a curtsy.

    Isabella watched as Mistress Anne reached down to the side of the chair she was sat in and picked up a case that looked like a cross between a small suitcase and a larger jewellery case.

     “This is just a little gift from Rebecca and myself. A little welcome gift.” Mistress Anne said with a warm smile for the first time since meeting Isabella.

     “What is it?” Isabella asked as she held the heavy case in both hands.

     “Open it and find out silly.” Mistress Anne giggled as she waved Isabella over to a table in the middle of the room so she could place the case down and look inside.

    Isabella opened the case and let out a gasp when she saw it was full of makeup and false nail kits as well as nail polish and other stuff Isabella didn’t know the name of, and all of it was brand new.

     “Thank you Mistress Anne, Rebecca.” Isabella said with a grin from ear to ear. “But I don’t know how to use makeup.” She added with a worried look.

     “Mistress Rachel can show you, but Rebecca and I will be coming to visit often, so Rebecca can also teach you a thing or two.” Mistress Anne grinned as she looked at Rebecca now stood at Isabella’s side looking inside the makeup case.

    Mistress Anne set the two maids to work again cleaning the library and other rooms while the two mistresses sat and talked about lots of different things.

    The afternoon passed quickly and it was soon time for Mistress Anne and Rebecca to leave, and Isabella seemed a little sad to see the two of them leaving.

     “I’ll come and visit again soon Bella.” Rebecca said as she hugged her goodbye. “Just remember what I told you, and be the best maid you can be.” Rebecca added with pride over what she was some of the time.

     “Thank you for all the help today Rebecca and I look forward to working with you again soon.” Isabella said as she hugged her back.

    Isabella then turned to face Mistress Anne and did a curtsy thinking that the woman wouldn’t want to hug a maid as it would be beneath her to do so, but Isabella let out a gasp when she found herself being pulled into a hug with the mistress. All Isabella could smell was a sweet perfume and the rich smell of leather from Mistress Anne’s dress.

     “I’m sorry I was so hard on you today, but I wanted to make sure you were serious about being a maid, and I must say that you look stunning in that new dress.” Mistress Anne said with a grin as she stepped back and gave Isabella a good look over.

     “Did you also buy me this dress as well?” Isabella asked before she realised what she’d just done. “I’m sorry Mistress Anne; please forgive me for not asking permission to ask that question.” She added as she bowed her head.

     “I’ll let you off this once, but don’t let anyone know I was going easy on you.” Mistress Anne whispered in Isabella’s ear just before she kissed her on the cheek.

    Isabella was left smiling as she watched Mistress Anne and Rebecca walk out to a waiting car and they both got in the back and were soon being driven down the long drive and out of sight.

     “I hope my sister didn’t scare you too much today Bella?” Rachel asked as she led Isabella back into the house.

     “She did a little Mistress Rachel, but it was fun hanging out with Rebecca, and she taught me so much in just one day.” Isabella said as they made their way back to the library. “I thought Mistress Anne hated me, but I was glad to be proved wrong.” She added as she thought about the hug she’d just gotten from Mistress Anne, and the wonderful gift of all the makeup in the large makeup case.

     “My sister is all for anything that makes me happy and having you around is just what the doctor ordered.” Rachel smiled.

     “Mistress Anne is very beautiful Mistress Rachel, just like you.” Isabella said as she looked over at Rachel as she walked beside her.

     “Thank you Bella, it is nice to be enjoying these clothes again.” Rachel said as she ran a hand down her side over the tight fitting black leather dress.

     “I prefer wearing my maid’s uniform to things like that.” Isabella said with a smile as she looked down at her own dress and the fake cleavage she had on show through the heart shaped cut out.

     “I must admit that you do look cute in that uniform, and it fits much better than the ones of mine you were wearing yesterday.”

     “May I ask a question Mistress Rachel?” Isabella asked.

     “Yes you may ask a question Bella.” Rachel smiled.

     “Should I wash the uniform before I leave this evening, so I can wear it again tomorrow?”

     “Follow me; I want to show you something.” Rachel said as she led Isabella over to the stairs and then went up to the bedroom where they had placed all the maid’s uniforms the other day. Rachel opened the closet door and let Isabella see that there were five more identical black PVC maid’s uniforms in their as well as all the other things to go with them.

     “Mistress Anne bought me all these?” Isabella asked as she looked at them all hanging on the rail just waiting to be worn.

     “My sister is eager to help you answer your true calling.” Rachel smiled.

     “I wish I could show her how grateful I am for all she’s done.” Isabella said as she stepped into the closet and ran her hand over the uniforms.

     “She saw how grateful you were today, and you’ve given her Rachel back.” Rachel said as she struck a sexy pose which made Isabella giggle.

    As the time was getting on, Rachel decided that it was time for Ian to return and get home before he got in trouble with his parents.

    Isabella actually looked sad as she was released from the dress, but she was soon running to use the toilet once she was out of the dress though. She’d wanted to go most the afternoon, but was too scared to ask about going while Mistress Anne was there.

     “You could have gone at anytime to the bathroom Bella.” Rachel said when she returned to the bedroom looking relieved to finally have an empty bladder again.

     “I was too scared of earning another spanking for asking.” Isabella blushed.

     “You don’t need to ask to take a potty break, just as long as you don’t take too long.” Rachel said.

     “But I’m not able to get the dress off to use the potty Mistress.” Isabella pointed out the fact that her new uniforms also have panties built into them to stop her getting the dress off over her head, not that she could with how tight fitting it was once it was zipped up at the back and locked in place.

     “Let me show you something.” Rachel said as she picked up the uniform that Isabella had just removed. Rachel pulled on the front of the panties and there was a ripping sound as a strip of Velcro pulled apart to allow the wearer to use the bathroom without the need to remove the dress.

    Isabella looked more closely and she saw that the panties could be locked in place if Mistress wanted to punish her for any reason, but for the most part she’d be able to use the bathroom when needed.

     “Why didn’t you tell me about this earlier?” Isabella frowned as she thought about how much pain she’d been in for no reason at all.

    Rather than giving Isabella an answer, Isabella was suddenly across Rachel’s knee again and was having her bottom spanked.

     “You’ve just earned yourself ten spanks for not asking to ask a question, and you also never called me Mistress, and I’m going to carry on spanking you until you start to call out each one and thank me for teaching you to be a good maid.”

     “One...! Thank you Mistress Rachel for teaching me to be a good maid.” Isabella shouted out. She then continued to shout out each number up to ten as Rachel landed each blow across her bottom, which hurt much more on her bottom this time due to her not having the frilly panties offering any extra protection.

     “Think yourself luck I didn’t have anything handy to spank you with.” Rachel said in a stern voice as she let Isabella get to her feet again.

     “I’m sorry Mistress Rachel, and thank you for spanking me and showing me how much you care.” Isabella said as she dipped Rachel a curtsy.

     “You’re most welcome Bella, now you better finish getting changed back to Ian, so you can get home and rest up.” Rachel said with a smile as she looked at Isabella stood there wearing the fake breasts and a pair of panties.

    Ian was soon back and he left the house waving to Rachel as he jumped on his bike and winced as his sore bottom landed on his bike seat.



Chapter Four: All good things must come to an end.

    Isabella was given her first lesson in using makeup the next day and then she got a bigger shock when she saw Mistress Rachel step into the bedroom dressed as a maid just like her.

     “Mistress said you needed some help with cleaning the bedrooms today, so I’m to help you while she’s away on business.” Rachel smiled as she took Isabella by the hand and led her to the first of the eight bedrooms on this floor.

    Isabella smiled as she worked side by side with Rachel like they were both just two maids doing their work while they talked like two friends would.

    Mistress Anne and Maid Rebecca started to come and visit a couple of times a week, and Mistress Ann had been correct about Rebecca being able to help her with her makeup lessons, and Isabella was getting pretty good after a couple of weeks.

    Isabella would have Maid Rachel come and help her a couple of times a week as well, which She enjoyed as much as Rachel loved to play maid alongside her, but Rachel did have to take it easy due to her bad heart.

    Ian got so used to the high heels and the fake breasts he whore as Isabella, that he felt lost at the end of each day when he had to take everything off and leave to return home to his boring life back at his parent’s home.

    He finally ended up getting cornered by Simon and the others one evening as he made his way home.

     “Can we talk to you Ian?” Simon asked as Peter and the others all circled around him.

     “Doesn’t look like I have a choice does it?” Ian said as he looked at them all.

     “It was just a bit of fun the other week when we broke into that house.” Simon said.

     “Well it wasn’t fun getting caught, and being shown the video evidence.” Ian lied.

     “They got video footage of you breaking in?” Peter asked looking worried.

     “No, they got video footage of all of us breaking in.” Ian replied. “They also know who we all are, and said that if any of you ever go near the house again, they will be getting the police involved.” Ian added to warn them away from trying to go near the house again, partly because he didn’t want any of them seeing Isabella there playing maid.

     “We’ve seen you going into the place a couple of times, have they got you doing some sort of punishment for getting caught?” Dean asked.

     “Yes, it was help out around the place, or they were going to call the police and then tell my parents.” Ian lied again.

     “That sucks man, but thanks for not getting us in anymore trouble.” Peter said. “I’m sorry I got you into all this trouble, it was just a bit of fun.” He added, but Ian didn’t trust he actually meant any of it.

     “How long have you got to keep helping out for?” Simon asked.

     “For the rest of the holidays.” Ian said as a cover for him going to the house every day and not having any free time to spend with them, not that Ian wanted to spend any time with them after what they tried to do. It had turned out better than Ian could have hoped for, but he also knew that it could have been very different if it hadn’t been Richard that caught him. Ian didn’t want to think what Mistress Anne would have done to him if she’d been there on the day he let Simon and the others talk him into running through the basement.

    Ian found it weird to think of Rachel as Richard, as he hadn’t seen Richard in the last couple of weeks since the first time Isabella met Mistress Rachel. He finally managed to get away from the boys and make his way home.

    Ian told Rachel what he’d said to the boys that broke into her house with him, and she said she did have video evidence of them breaking in if he wanted a copy to prove that his lie wasn’t a lie, but she didn’t know the boys names or addresses. Ian offered to give them to her, but she wasn’t bothered about any of that, as the locks on the basement doors had been fixed now and no one would get in there without a key or actually breaking the door down.

    Isabella kept helping out around the house and just keeping Rachel company when she was having trouble with her heart. Isabella would watch over her while she slept when she needed to take some medicine and then go to bed for an hour or two in the day. She would explore the house while Rachel slept on the bad days and once she’d got all her duties taken care of.

    Maid Rachel had been helping Isabella one day when she’d had some trouble with her heart and had to go to bed and rest for a couple of hours. Isabella had gotten all the work done and found herself down in the basement looking through some of the boxes down there.

    Isabella was soon looking in a box at a pile of bondage gear. She wondered what it was like to be locked up in all of it and was soon finding out as she started to sort her way through the box. Isabella soon had a ball gag, wrist and ankle cuffs sorted out, and padlocks with keys sorted out to go with them all.

    After going up to check on Rachel, Isabella returned to the basement and her self bondage session.

    The first thing Isabella did was to place the ball gag in her mouth and do up the strap at the back. She had to wonder just how people got any pleasure out of having something like this in their mouth for any length of time. She’d only had it in a couple of minutes and already she was starting to have trouble with drool, but she carried on and placed the ankle cuffs on next and then added a padlock to each one before she struggled with the wrist ones and got them locked in place.

    Isabella found she wasn’t that keen on bondage to this extent, but thought that if she wanted to carry on and become a maid to a mistress like Rebecca was, then this was something she’d need to get use to, so she decided to tidy up the basement while still wearing the bondage to see if she could get use to it.

    She’d been working down in the basement for about thirty minutes when she’d had enough of the drooling problem and decided that she needed to remove the ball gag, so she started to shuffle her way back to where she’d left the keys to the wrist cuffs, so she could remove them and then remove the ball gag. She couldn’t get her hands around to the back of her head with the wrist cuffs on, due to the chain linking them. Isabella was just reaching out for the keys when a loud banging sound made her jump and spin around to see what was making it.

    Isabella froze in her tracks when she saw Simon and Peter stood looking in through the small window in the basement door, but it’s what they said next that really scared her.

     “Don’t worry Ian, we’ve called the police and they’re on their way right now.” Simon shouted to him just before the basement door was kicked in by Dean and Peter.

    He soon realised how this all looked, and they must think that he was being forced to dress like this and then get locked up while he worked like a slave for some group of perverts. Ian was worried about how this was going to affect Rachel’s heart when the police turned up.

    Ian was then picked up and carried out of the house by Dean and Peter before he knew what was happening. Ian was still gagged, so he couldn’t come clean and say that he’d done this to himself, and the keys to the cuffs were back in the basement on the other side of the lawn to where Ian was now sat dressed as a maid.

     “Jesus Ian, what have those sick fucks been doing to you?” Simon said as he looked down at Ian who was now sat on the lawn looking up at the five boys. None of them had the common sense to try and remove the ball gag, even though Ian was trying to tell them to remove the gag so he could explain.

    Ian was forced to sit on the lawn and watch as first one police car showed up, and then a couple more arrived after the first officers saw how Ian was dressed and locked up.

    Richard was soon being dragged out of the house and he looked at Ian with a sad look, but he never fought back or argued his innocence as he was loaded into the back of a police van and taken away.

    Ian tried to tell the police that he’d done it all to himself and Richard was innocent, but the police just said he’d been brainwashed into thinking that, and that Richard had already admitted to all the charges. Ian couldn’t understand why Richard would do something like that.

    The press found out about it and it ended up becoming a big deal in the news and they managed to get pictures of Ian sat on the lawn wearing the maid’s uniform and locked up in the gag and other stuff as well. Ian knew it was one of the boys that took the picture and then sold it to the press.

    Peter seemed to have a new phone and bike not long after it all happened, so Ian had a pretty good idea that it was him that sold the photo, or his parents had.

    Due to all the press the story had gotten, Ian and his parents had thought about moving, but with his picture being in the papers and on the news, Ian couldn’t get away from it, so even though there wasn’t much of a court case due to Richard admitting to everything. They stayed where they were and Ian just had to live with the weird looks he would get from everyone, and all the whispering that would happen as he walked into a room.

    Richard was sentenced to seven years in a low risk prison as he needed special care due to his heart condition. Ian wondered if Mistress Anne had anything to do with the sentence Richard got, as the newspapers said the sentence seemed a little light for what had happened, but the story soon got forgotten as more interesting things happened. One being a politician being photographed in the same sort of gear as Ian had been caught in.

    Ian hadn’t spoken to Richard or his sister since that day at the house when Richard was arrested, and he’d never tried to wear any girl’s clothes either. Partly due to it making him feel sick to do so, but also due to his parents now keeping a close eye on him to make sure there wasn’t any long lasting effects from the traumatic events he’s suffered. Well that’s what a group of shrinks had said to his parents after it all happened. Ian had destroyed all the things he had at home in a fit of anger over losing his best friend and Mistress, and what his stupidity had caused.

    Sick of being looked at like a freak, Ian was soon doing any stupid dare others dared him to do. He was now on a path to self destruction as he tried to act super macho and force people to forget about his past as a maid, and see him as a trouble maker. He was hanging around with Peter and the others, but even they soon tried to distance themselves from him the more daring he became.

    Ian was soon getting in trouble with the police, but he would always get let of lightly after they blamed it all on what happened to him, this would just make Ian even angrier with everyone, and force him to do worse things.

    It wasn’t long before Ian was doing drugs and hanging out with the wrong sort of people. His parents tried all they could to get him back on track while blaming the pervert that was now locked up in prison.

    All the time Ian was acting up and getting in trouble, he would always think about Mistress Rachel and how he missed being Isabella and then this would make Ian angry and he would go out and do something stupid to get in trouble.

    Ian’s life finally fell apart a couple of years later when he read in the paper that Richard had died in prison due to complications with his heart. This was the last straw for Ian as he saw it as being his fault Richard had died. Ian was convinced that he’d been the one to kill him, and he couldn’t cope with living this life any longer, so he made his way up onto a bridge that overlooked a river. He’d heard people say that this river had a strong undercurrent, and lots of people had drowned here, so he thought this would be a good place to end his miserable sixteen year old life.

    He’d spent some time typing up a letter explaining what had really happened that day back at the house and then done a second one to leave with his clothes on the bridge for someone to find later. He wanted the world to know that Richard was a wonderful person, and not the monster that the press had made him out to be. So with the true story in the post on its way to a newspaper and the other note left under a small rock with his shoes, jacket and ID, Ian started to climb up onto the railing when he felt a sharp jab in the back of his neck just before the world went dark.

 

To Be Continued Next Tuesday  

 

Story by SaraUK

 

Edited and Posted by SamanthaK

    EDITORS NOTE: Please Comment and/or leave Kudos and let Sara know you like her work please, Any comments on spelling, grammar or the layout of the story please PM me “Samanthak” not Sara. Thank you

Sentenced To Life Part 03

Author: 

  • Sara UK

Caution: 

  • CAUTION: Physical or Emotional Abuse

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Fiction
  • Novel Chapter
  • 17,500 < Novella < 40,000 words

Genre: 

  • Transgender

Character Age: 

  • Teenage or High School
  • College / Twenties

TG Themes: 

  • Femdom / Humiliation

TG Elements: 

  • CAUTION
  • Castration / Male Chastity Devices
  • Chastity Belts
  • Corsets
  • Dominance & Submission / Bondage
  • Maids / French Maids / Servants
  • Retro-clothing / Petticoats / Crinolines

Permission: 

  • Posted by author(s)


 © January 2013


Part Three


Chapter Five: A fate worse than death.

    Ian felt life coming back into focus as he tried to remember what he’d been doing before he fell asleep, then he remembered what he was trying to do and opened his eyes to find himself in a white room, but things soon got weirder when he tried to move his arms and found out he was wearing a straitjacket and the room had padded walls and floor, so trying to kill himself was going to be a waste of time by running into them, and he did try a couple of times.

    He fought to get out the straitjacket for a couple of minutes as he rolled around on the floor, but he soon realised that he was stuck in this thing until someone released him. Ian was also in some pain as he’d become dependent on drugs and was in need of a fix that he knew he would never get, not in this place, where ever this place was.

     “Hello...!” Ian screamed out over and over again until his voice was horse, but no one came to check on him.

    Needing to pee and not being able to stop it, he was soon letting it out, but it never made a mess on the floor and Ian soon realised that he was wearing an adult diaper, so he wasn’t going to be seeing anyone anytime soon and they weren’t going to trust him to use a toilet.

    He couldn’t work out why anyone would want to try and save him when he didn’t want to save himself. Ian knew he must have fallen asleep because when he looked over to the door, he saw that a tray had been slid through a slot at the bottom of the door.

    The tray had two bowls on it, one had water in it and the other had some sort of food that he couldn’t work out what it was, but it looked a little like baby food.

     “I’m not a dog...!” He screamed out, but he was hungry and thirsty, so he bent over and lapped up the food and then did the same with the water before feeling sleepy and drifting off to sleep again.

    When he next woke up, he was wearing a clean diaper, but he was still wearing the straitjacket and was still locked in the padded cell.

    This went on for some time and Ian was in a lot of pain as he basically went through cold turkey to wean him off his dependence on drugs. He found himself wishing for someone to just come into the padded cell and end his pain as the effects of the drugs, or lack of them made him feel worse and worse, but there was no release from it, and he just had to sit in a corner praying for death.

    Ian tried to not eat the food to force his captors to show their faces, but they were able to hold out longer than Ian was and he always ended up eating the baby food and drinking the water before he fell asleep, just to wake with a clean diaper on. He always felt cleaner as well, so he guessed they were removing the straitjacket and washing him as well while he was out.

    Ian had lost all track of time and had given up on ever seeing another living being again when he heard the door being unlocked and then opened. His need for drugs was a thing of the past by this point and he still had no idea how long he’d been locked up for. He was so happy to finally be seeing someone, but that soon turned to fear when he saw who it was stood in the doorway.

    With her hair pulled back into a tight bun on the back of her head and wearing a figure hugging black leather cat suit and holding a cane in her leather covered hand was Mistress Anne, Richard’s sister. She had nothing on her feet except pantyhose or stockings; she walked into the padded cell and looked down at Ian as he cowered in a corner looking worried as he focused on the cane in her hand.

     “Hello my little pet.” Mistress Anne purred softly as she bent down and ran a leather covered finger along his cheek. “I’ve been waiting so long to get my hands on you, and to think you almost managed to get away from me by throwing yourself off that bridge.” She added with a pout.

    Ian found the soft way Mistress Anne was speaking, even more menacing than if she was snarling at him. This cool calm Mistress Anne was being cold and calculated, like she had a plan already set out and Ian wasn’t going to like it. At least if she was shouting at him, she would be acting out of anger, but she was controlled and had a plan worked out.

     “I’m sorry Mistress Anne, I never meant for any of this to happen...” Ian started to explain, but stopped when Mistress placed a finger on his lips and shushed him.

     “I believe you are my little pet, but trust me when I say that you will soon learn the true meaning of the word sorry, and that there are fates far worse than death.” Mistress said in the same soft caring tone, but her eyes said she was anything but caring. “You are dead by the way, well according the rest of the world you are.” Mistress added with a smile like she was happy about that little fact. “Rebecca...!” She called out as she looked over her shoulder towards the door.

    Ian looked at the door expecting to see Rebecca walk in dressed as a maid, but she was soon worried when she saw her enter the room wearing the same outfit as Mistress was wearing.

    Mistress Anne held out her hand and Rebecca placed some newspapers in it. Mistress was soon opening the paper and showing Ian a picture of himself with the headline saying he was dead after throwing himself off a bridge. There was also a piece on his letter that he’d send to the paper explaining what happened and how the police had locked up an innocent man.

    Ian also noticed the date and realised he’d been locked up in this cell for almost two months now and the police had finally given up all hopes of ever finding a body.

     “What is it you plan to do with me?” Ian asked looking nervous now.

    Ian was soon to find out as he was pulled out of the corner and he fell face down in the middle of the room, but before he had time to try and move, Mistress Anne had a foot on his back pinning him down while she took the cane to his backside. Even though he was wearing a diaper, he could still feel each blow rain down on him.

     “You will always refer to me as Mistress Anne, and Rebecca as Lady Rebecca.” Mistress said with each blow she landed on his backside. Just as Ian thought Mistress had finished she landed a blow across the top of his legs that sent a searing pain through him and made him scream out and start to sob as he was finally able to move again, but he couldn’t get his hands free of the straitjacket to do anything about the pain.

     “I’m sorry Mistress Anne, Lady Rebecca.” Ian said through gritted teeth as he made his way back into the corner, like he’d be safe there.

     “Get use to that pain my little pet, you will learn to love it as time goes on.” Mistress purred as she bent over to look Ian in the eyes. “And remember that I own you now, and you will only die when I allow it and grow tired of torturing you for the death of my brother.” Mistress added before she turned and left the room.

    Ian was left in the padded cell with Lady Rebecca. “Stand up and turn to face the wall.” Lady Rebecca said as she pulled something out a bag she had strapped around her waist.

    He struggled to stand without the use of his arms, but he was finally stood and looking worried as he tried to work out what Rebecca had planned for him.

     “Please don’t hit me again Lady Rebecca.” Ian pleaded with her.

     “I won’t be punishing you Bella; that is the sole job of Mistress.” She explained. “I am just going to put some cream on the welts left behind by the cane. This will help to cut down on the scaring.” Rebecca said as she started to dab some cold cream across the two welts that were forming where Mistress just landed the cane across the top of his legs.

     “May I ask a question Lady Rebecca?” Ian asked as he remembered all the training he’d been given by Mistress Rachel all those years ago.

     “Yes you may ask, but I may not give an answer, or an answer that you like.” Rebecca said as she stood up again and turned Ian around to face her.

     “Will I ever be allowed to leave this room and get out of this straitjacket? Lady Rebecca.” He added the last bit when he saw she was waiting for him to say her name to stop anymore punishments being handed out.

     “I think Mistress plans for you to carry on your training and become the maid that Mistress Rachel hoped you would be.” Rebecca explained. “Mistress has already started you on hormones, and she plans to have your breasts enlarged at some point in the future.” She added in a matter of fact way.

     “Don’t I get a say in any of it Lady Rebecca?” Ian asked looking shocked at the news he’d have breasts soon, he’d not given any thought to becoming Isabella again since the trouble that cost Mistress Rachael her life.

     “You’ve just earned yourself five strikes with the cane later in the day.” Rebecca said with a sigh.

     “But what for Lady Rebecca?” He whined.

     “That’s another five.” Rebecca frowned. “You only asked for permission to ask one question, but you asked me two more, so now you will be given ten strokes of the cane at the end of the day.” Rebecca explained before Ian could earn himself anymore.

    Rebecca knew that Mistress was listening in on what was being said, and Rebecca didn’t want to earn a punishment by not reporting any and all violations Ian made.

     “I’m sorry for being rude and asking more than one question then Lady Rebecca, and I will try to remember that in future.” Ian said as he tried to do a curtsy.

     “It looks like you’ve forgotten all that I taught you.” Rebecca said with a small smile when she saw how bad the curtsy was.

    Ian wanted to complain about it being the fault of him being stuck in a straitjacket, but decided it would be best to not say anything and earn even more strikes with the cane later in the day.

    Rebecca finally left the room and Ian felt alone more than ever, and wondered if causing trouble would bring either of them back to spend more time with him, but the pain where Mistress had caned him made him decide against causing trouble.

    Ian felt glad for the first time since being found by Simon and the others that day three years ago, he was glad that he was the one being punished for what happened, but he was scared about becoming Isabella again as he associated everything to do with her with what happened to Mistress Rachel and it all being bad for him to dress that way.

    Mistress Anne and Lady Rebecca arrived in his cell later in the day and he was forced to thank Mistress after every lash across his backside, but he was grateful that Mistress never missed and hit the back of his legs again. Ian wondered if she did that one lash across his legs to let him know just how painful it could be if he made too many mistakes.

    Ian remained in the cell and the straitjacket for another couple of weeks, always falling asleep after his one meal each day and waking to find his diaper changed. So he was shocked to see Lady Rebecca enter his cell one day with a plate of salad and grilled chicken for him, and a knife and fork to eat it with.

     “Good afternoon Bella, and how are you feeling today?” Rebecca asked with a smile. She had never once called him Ian since first entering the room and letting him know who it was that had him locked up.

     “Fine I guess Lady Rebecca, but I’m bored with being stuck in this room all the time without the use of my arms.” Ian said as he tried to move his arms to prove his point.

     “Do you think Mistress and I can trust you if we gave you use of your arms back and let you out of the cell?” Rebecca asked just before she cut up some chicken and some salad and held it up to Ian’s mouth.

    Ian had to nod a yes as he now had a mouth full of food and found it weird to be chewing food instead of lapping it up like he’d been doing for the past couple of months. He’d lost a lot of weight though around his waist, but his chest felt bigger, as did his hips and bottom from what he could feel and see when he looked down at them over his folded arms. He wasn’t stupid and already knew that the hormones Rebecca said he was being given were working to change his body.

     “Mistress will come in and explain the new rules for you, and you will have to agree to them all, if she’s to let you out of here.” Rebecca warned.

     “I’ll do anything to get out of this room Lady Rebecca.” Ian said now he’d finished chewing and swallowing.

     “We’ll see if that is true.” Rebecca said sounding cryptic, but she never said anymore as she carried on feeding Ian in quiet.

    Ian had learned the hard way not to talk unless given a chance to, so he sat and ate each fork full offered to him and then smiled a thank you when Rebecca got to her feet and left the room once he was finished eating.

     “Mistress and I will return later in the day to see if you are willing to do anything to get out of this room.” Rebecca said with a look around his cell before the door was closed and locked with a loud clanking sound that always let Ian know he was never going to kick that door down, even if he did have use of his arms.

    Ian was sat up in a corner of his cell nodding off when he next heard the locks being undone on his cell door and he opened his eyes just in time to see Mistress Anne and Lady Rebecca enter the room. He tried to sit up as best he could, but it wasn’t easy with both arms wrapped around his body in a straitjacket.

     “Hello my little pet, and how are you feeling today?” Mistress asked in her normal soft friendly tone. “Lady Rebecca tells me that you’re ready to get out of this room, is that true?”

     “Yes please Mistress Anne.” Ian replied as he looked up into her eyes and then quickly looked away again when he saw Mistress Rachel looking back at him and he felt a pang of pain over what he caused to happen again. Seeing Mistress Anne was a constant reminder of Mistress Rachel and how he would never get to see her again.

     “Do you promise to do whatever I ask without trouble or question?” Mistress asked as she placed the riding crop she was carrying under his chin and forced him to look up into her eyes, just so she could see the pain he felt in them.

     “Yes I promise Mistress Anne.” Ian said trying to swallow his pain and look braver than he felt over what his future would be like.

     “I want you to fully understand that I own you, and your life is mine to do with as I please, and it is Isabella that will leave this room and be around until such time as I tire of you and decide to end your life at a time of my choosing.” Mistress said in a cold hard tone as she looked Ian in the eyes to let him know she was being deadly serious about what she said. “The person you knew as Ian Phillips died when he jumped from that bridge a little over four months ago.” Mistress added.

     ‘Four months...?’ Ian thought to himself ’It’s been over four months since I was placed in this room...?’ Ian realised that he really had lost all track of time and he found himself wondering if anyone missed him, or mourned his death. He doubted that due to him alienating himself from everyone, even his own parents had given up on him.

     “I’m yours to do with as you wish Mistress Anne.” Ian said as he lowered his head at her feet.

     “Lady Rebecca... Get her dressed and put to work, but keep a very close eye on her and report all the trouble she causes.” Mistress said before she turned and left the room with Ian still kneeling at her feet.

     “Let’s get you on your feet and out of that straitjacket Bella.” Rebecca said as she pulled Ian to his feet and then turned him to face the wall while she undid all the straps at the back and released his arms.

    Ian’s arm’s just fell limp at his sides once the jacket was removed, but he was soon screaming out in pain when he found himself pushed up against the padded wall with his left arm being pushed up his back as Rebecca whispered in his ear.

     “I don’t want any trouble from you Bella, as you can see, I am quite able to overpower you, and Mistress is just waiting to take her riding crop across that cute little bottom of yours, and it won’t be protected by a nice padded diaper after today either.” Rebecca warned.

     “I have no desire to cause trouble Lady Rebecca.” Ian sobbed as he tried to work the pain out of his arm once Rebecca let go of him.

    Ian was shocked when he looked down at his now naked body and saw that he had a small set of breasts and a set of female hips. He wasn’t Ian anymore, but looked more like Isabella now all apart from the thing between his legs, which was locked away in a chrome looking pair of panties which he later found out was a form of chastity belt.

     “That will force you to sit down when using the toilet from now on, and it’s locked in place and Mistress has the only key.” Rebecca informed him when she saw him feeling around for some way to remove it. “You are to think of yourself as Isabella from now on.” Rebecca warned. “Like Mistress said, Ian Phillips is dead.” She added as she stepped out the room and returned with a trolley full of clothing for him to put on, or her, as he was no longer a male called Ian, but a female called Isabella, or whatever else Mistress wanted her to be. Ian had been worried about the fact Mistress kept calling him a pet.

    Isabella looked scared when she saw that Rebecca was going to dress her as a maid, just like she was dressed when Mistress Rachel was arrested and charged with kidnapping and brainwashing Ian into becoming a maid, even though none of it was true.

    Rebecca saw the fear in Isabella’s eyes and knew this was going to be hard on the girl, but it had to be done to get her over this large hurdle and back into the frame of mind Isabella once had.

    She handed Isabella a pair of black pantyhose to put on, and then she stood and waited with a pair of frilly panties while Isabella sat on the floor and struggled to put the pantyhose on with her jelly arms that she wasn’t used to having use of after so long in a straitjacket.

    Isabella was soon in the pantyhose and then she stood up again and took the panties from Rebecca and stepped into them before she took a bra off her and slipped that on and did up the hooks at the back before she seated her small breasts in the cups. This was the weirdest thing Isabella had ever done, but it also felt nice to have her own breasts to do that with.

    Once she had the bra on, she took the maid’s dress from Rebecca and stepped into that before pulling it up her body and slipping her arms through the sleeves and then turning to let Rebecca zip it up at the back. Isabella heard a loud click and knew she’d just been locked into it until such time as she was released, but she had a feeling that her work days from now on would be far worse and longer than any she had while working for Mistress Rachel.

     “How does that feel Bella?” Rebecca asked as she heard Isabella let out a pleasant sounding sigh as she ran her hand over the silky feel of the fabric the dress was made out of.

    Isabella smiled as she looked down and saw her own small breasts through the heart shaped cut out on the maid’s uniform on her chest that allowed people to see a little bit of cleavage.

     “We need to do something with your hair as it looks a mess.” Rebecca said in a scolding tone like it was Isabella’s fault it had gotten so bad. “It is much longer now though, so I should be able to do wonders with it.” Rebecca added with a smile.

    Rebecca led Isabella out of the padded room and then made her sit on a chair that was just outside the room so Isabella could put on the high heels that were sat next to it. Rebecca put her own shoes back on while Isabella put hers on.

    Once Isabella had the shoes on, Rebecca knelt down and added a small lock to each ankle strap so Isabella couldn’t remove them. Rebecca then added a set of ankle cuffs with a short chain connecting them just before she added a second set of cuffs just above Isabella’s knees. Rebecca wasn’t done yet though as she then added a set to Isabella’s elbows with a longer chain running around her back that allowed Isabella to keep her elbows at her side. Rebecca then added a set of wrist cuffs with a shorter chain.

     “I’m adding this next item to help you keep out of trouble until you can learn to not speak out of turn.” Rebecca said with some sorrow in her voice as she picked up a ball gag and held it up to Isabella’s lips.

    Isabella looked scared as she clamped her mouth shut to begin with, but soon relaxed again when she realised she couldn’t stop Lady Rebecca from forcing it in, and that would just earn her some form of punishment.

     “That’s a good girl.” Rebecca said as she pushed the ball into Isabella’s mouth and then did up the strap at the back.

    Rebecca then picked up what looked like a dog collar and placed it around Isabella’s neck, but not before showing Isabella the dog tag that had her name on it, and under that it said that she was the property of Mistress Anne and Lady Rebecca.

    Once Isabella was suitably chained up and put on a lead, Rebecca picked up the other end of the lead and started walking along the long stone hallway with no windows to a set of steps that led up to someplace. Isabella did the best she could to keep up with Lady Rebecca, which wasn’t easy given the small steps she was being forced to take, thanks to the ankle and knee chains slowing her down.

    They finally made it to the top and then Rebecca punched in a code on a keypad and the large heavy looking wooden door clicked open and Rebecca led Isabella out into a very large looking hallway.

    Isabella soon realised that this house was massive compared to the place Mistress Rachel had lived in, but Isabella remembered Mistress Rachel saying that Mistress Anne had bought her the house, so Mistress Anne must be able to afford a bigger place for herself. One look out the first window she saw, told her that she wasn’t even in the UK anymore. The place looked more like a castle up in the mountains some place that was surrounded by more mountains, so even if she was able to get out the place, Isabella could see she had no place to run to, not that she wanted to run away. Isabella knew she had a price to pay for what happened to Mistress Rachel, and now she had been sentenced to life as a maid.

    Rebecca walked Isabella through part of the castle and into what looked like a salon where she sat her in a chair and then locked her in place and pulled the lead behind her someplace and locked that in place so Isabella was left looking up at the ceiling. If she tried to move her head forward, she was choked, so she had no choice but to remain how she was and let Rebecca do her job.

    Isabella was soon having her hair washed, and then Rebecca released her collar chain so she could work on Isabella’s hair as she trimmed it and then placed it in rollers and then stuck her head in a large dryer. While Isabella’s hair was drying, Rebecca set to work on Isabella’s nails as she trimmed them down and then added some false nails over the top and then she added a nice shade of pale pink to them.

     “You look better already Bella.” Rebecca smiled as she took out the rollers once Isabella’s hair was dry. “Now I need to take care of your face and ears.” She added as she set to work pulling out most of Isabella’s eyebrows until there was just a thin arch of hair left.

    Isabella looked worried and tried to get out the chair she was still locked into when she saw Rebecca approaching her with a scary looking gun of some sort.

     “Relax Bella; it’s a piecing gun so I can add some studs to your ears.” Rebecca said in a calming voice.

    Isabella relaxed and let Rebecca place the gun up to her ear; she was soon sporting three studs in each ear after Rebecca seemed to get carried away with the gun.

     “See, that wasn’t so bad, was it?” Rebecca asked with a grin. “Now I’m going to remove your gag, but I don’t want to hear a word out of you, or you will be punished for it.” Rebecca warned as she stepped behind Isabella and undid the strap before pulling the ball out of her mouth.

    Isabella worked her jaw to try and get rid of the stiffness she had from being stuck with the thing wedged in her mouth for the past hour or so, but she never said a word.

    Rebecca set to work on doing Isabella’s makeup to finish off her new look. Isabella found herself wondering what she looked like with her new hairdo and pierced ears. There were no mirrors in the room, so Isabella was forced to wait until Lady Rebecca decided it was time to see the finished results.

     “Are you ready to meet the new you then Bella?” Rebecca asked with a grin when she was finally finished.

    Isabella was just about to answer her when she remembered what Rebecca had said about her not speaking when she removed the ball gag, so she stopped herself and nodded her head up and down instead.

     “Very good Bella, that was a test and you passed it with flying colours.” Rebecca smiled as she unlocked Isabella from the chair and helped her to her feet again.

     ‘Great.’ Isabella thought to herself. ‘I’m going to be tested to see if they can trick me into getting myself punished.’

    Rebecca picked up Isabella’s lead and led her over to a set of mirrors in another room and Isabella was left looking at a pretty looking maid in a black silk uniform. It took her a couple of seconds to realise that it was her she was looking at all locked up in her chains.

     “I look pretty.” Isabella said, not bothered about the punishment she just earned by speaking. “Thank you Lady Rebecca.” She added with tears in her eyes over the fact Mistress Rachel would never get to see how she turned out.

     “Are you ready to go and see Mistress?” Rebecca asked as she picked up the lead again.

    Isabella nodded a yes and then followed Rebecca off in the direction she gathered Mistress Anne could be found. Rebecca led Isabella into a large room where she could see Mistress Anne sat behind a large desk looking over some paperwork and then tapping away on a computer.

     “Well don’t you look a 100% better now?” Mistress asked with a smile. “How do you feel Bella?” Mistress added.

    Isabella wasn’t sure if she was allowed to speak again yet or not, so she just looked at Rebecca to see if she could answer.

     “Well answer Mistress before you earn another punishment.” Rebecca said as she pulled on Isabella’s lead.

     “I feel a 100% better thank you Mistress Anne.” Isabella replied as she tried to do a curtsy, but it was hard with all the cuffs and chains.

     “Please don’t be to hard on Bella for not answering right away Mistress, but I told her not to speak in the salon while I did her makeup, and I hadn’t told her the rule about you always wanting an answer to a question when you ask a question.” Rebecca explained the reason for Isabella’s confusion.

     “So you think I should give you the five lashes I was thinking of giving Isabella then for not answering fast enough?” Mistress asked as she leaned back in her chair and started flexing the riding crop she’d just picked up off the table.

    Rebecca went to say yes, but was stopped when Isabella spoke up in her place. “Please don’t punish Lady Rebecca for my mistakes Mistress Anne, I will accept any punishment my slowness has earned.” Isabella said trying to look brave.

     “Very well then, you will now receive fifteen lashes of the crop for your punishment.” Mistress said as she rose to her feet and walked around her desk to where Isabella was stood next to Rebecca. “You will receive five lashed for each time you spoke out while Lady Rebecca let you look in the mirror, and another five for not answering me fast enough.

    Isabella leaned over as best she could to allow Mistress easier access to her bottom. Rebecca pulled up Isabella’s dress and held it out the way. Isabelle was soon hearing a swishing sound as Mistress struck out at the air with her riding crop, then Isabella heard a swish just before pain exploded across her backside like someone had just placed a red hot poker on it.

     “One... Thank you Mistress Anna.” Isabella got out through gritted teeth.

     “Thank you for what my little pet?” Mistress asked as she stroked a hand over Isabella’s bottom where she just hit her.

     “Thank you for teaching me to be a better maid?” Isabella asked in a tone that made it sound like a question.

     “Are you asking me or telling me?” Mistress asked with an edge of anger in her voice as she leaned down to look Isabella in the eyes as she flexed the crop in her hands.

     “Thank you for teaching me to be a better maid.” Isabella repeated, but sounding more convinced this time.

     “Let us start again then.” Mistress said as she stepped behind Isabella again and started over.

    Isabella counted off all fifteen blows and she had tears streaming down her face from the pain by the time she called out the thank you for the fifteenth blow. She also knew she wouldn’t be sitting down again anytime soon with how on fire her bottom felt right now. Rebecca had been right about it hurting much more without a diaper to cushion the blow any.

     “You’ve made such a mess of all that pretty makeup Lady Rebecca put on you.” Mistress said with a pout as she lifted Isabella’s chin with the crop. “Maybe I should give you another fifteen for doing that alone.” Mistress added as she enjoyed the look of fear in Isabella’s eyes at the very thought of another fifteen lashes of the crop. “But I think we will just let Lady Rebecca take you back to the salon and let you have a go at repairing the damage yourself.” Mistress said as she went back to looking at her computer and paperwork like they had already left the room.

    Isabella let out a wince of pain when Rebecca made her sit in the chair gain and then get locked into it before Rebecca removed the wrist and elbow cuffs, so Isabella could repair her own makeup.

    Rebecca made Isabella redo it half a dozen times before she said she was happy with the results and Isabella was put back in her cuffs before Rebecca released her from the chair and let her up off her tortured backside.

     “I think we should replace this to stop you earning anymore punishment today if we can help it.” Rebecca said as she held up the ball gag again.

    Isabella opened her mouth and let Rebecca place the ball in her mouth before she redid the strap at the back and then led Isabella off in another direction to where Mistresses office was located. Isabella soon found herself in a large kitchen where a couple of woman dressed as cooks were busy working on a meal for Mistress.

     “I’ve brought you some help, use her as you see fit.” Rebecca said before she let go of the lead and just left the room again without giving Isabella a second look.

    Isabella was soon being given things to move around the kitchen from one cook to the other. None of them spoke to her, other than to give an order to her. Once the meal was ready, Isabella was shown where the dining room was and she was set the task of delivering the food to the table for Mistress Ann and Lady Rebecca.

    The head cook wrote something on a piece of paper and put it on a silver try that she’d given Isabella to carry, before she sent her off to Mistresses Office to let her now dinner was ready.

    Isabella reached the office door and saw it was shut, so she knocked and then waited to be told to enter. She heard Lady Rebecca’s voice tell her to enter and she struggled to open the door without dropping the tray as she entered the room and walked over to where Lady Rebecca was sat.

    Rebecca pointed over to Mistress Anne, so Isabella shuffled her way over to Mistresses desk and then waited for her to take the note off the silver tray.

    Mistress carried on working for a couple of minutes before she picked up the note and then waved Isabella from the room again. Isabella made her way back to the dining room to wait for Mistress and Lady Rebecca to arrive.

    Another maid arrived with Mistress and Lady Rebecca, and Isabella was soon being told what to do by this new maid as her silver tray was loaded up with things so she could ferry them back and forth to the kitchen. Isabelle was left with the gag in her mouth all evening, even after she helped to clear the table and the other members of staff sat and ate their evening meal while Isabella was left to stand at the end of the table watching them eat. It all got too much for her as the room started to spin and she blacked out.

    Isabella woke expecting to find herself back in the padded cell, but when she opened her eyes she found herself in a small room with a wardrobe and a bedside table, as well as the bed she was lying in.

     “Don’t try to get up just yet Bella.” Lady Rebecca said as she stopped Isabella from sitting up. “You ended up with a nasty bump on you head when you passed out last night.” She explained.

     “What happened to me and where am I now Lady Rebecca?” Isabella asked as she let out a groan from the pain at the side of her head.

     “This is your new room, and the staff should have sent you to find me or Mistress after you finished helping them in the kitchen and before they ate their dinner.” Rebecca frowned. “Mistress has punished them all for not taking better care of you.” She added.

     “Please don’t punish them for my mistakes; they will just hate me more than they already do.” Isabella whined as she struggled to sit up this time and get out of bed.

     “What are you doing?” Rebecca asked.

     “I need to get ready for work; I don’t deserve any special treatment from anyone, not after everything I’ve done.” Isabella said as she got to her feet and made her way over to the wardrobe where she guessed her uniforms were.

     “And what is it you think you’ve done?” Rebecca asked as she got up and started to help Isabella get ready for work.

     “I killed Mistress Rachel, and now Mistress Anne is punishing me like I should have been punished at the time.” Isabella said as she burst into tears.

    She found herself being hugged by Rebecca as she sobbed for the first time since all the trouble happened back at the house.

     “You never killed Mistress Rachel Bella, her heart just gave out, and she never blamed you once for what happened.” Rebecca explained as she held the sobbing girl in her arms.

     “Then why did she never tell them that I wanted to be her maid and she never once forced me to dress up?” Isabella asked looking confused. “Why didn’t Mistress Anne just let me kill myself that night on the bridge? I’d be better off dead than living like this just waiting for her to finally end my life.” Isabella added in a bitter sounding tone.

     “That is a conversation you will have to have with Mistress at some point, but right now let’s just get you ready for another busy day of work.” Rebecca said as she carried on helping Isabella to get dressed in a clean uniform and cuffs again, but she left out the gag today.

    Isabella was soon dressed and then she let Rebecca lead her out her new room and down a hallway to the kitchen where she could here pots and pans being clanked around, but they all fell quiet when they saw Lady Rebecca and Isabella enter the room with Isabella on her dog lead again. Isabella was worried how they would react to her after being punished for her fainting the night before, but she got a shock when they all rushed around her making sure she was alright before they sorted her out with some egg on toast for her breakfast and a cup of tea.

    Rebecca removed the wrist and elbow cuffs so she could eat her breakfast on her own.

     “How are you feeling this morning Bella?” The maid from the night before asked as she sat at Isabella’s side while she ate her breakfast and realised just how hungry she was. Isabella seemed to remember Mistress calling this maid, Amanda at dinner the evening before.

     “I’m fine thank you for asking Miss Amanda.” Isabella said trying to sound polite between mouthfuls of food.

     “Please just call me Amanda; I’m just a maid like you.” Amanda grinned.

     “I doubt that, I don’t see you wearing all this extra jewellery.” Isabella said as she tugged on the chain hanging from the dog collar around her neck to prove a point.

     “True, but then I’m not a risk like you are to yourself at the minute either.” Amanda pointed out.

     “I’m nothing more than a pet.” Isabella sighed. “Mistress will soon get bored with me and then I will be gone.” She added as she realised that Mistress Anne would soon be sick of looking at her and then she will just do away with her like a sick animal.

    Amanda and the two cooks looked shocked to hear Isabella think so little of herself, but they never said anything, not wanting to argue with her over it.

    Rebecca had gotten up and left the room to go see Mistress and report in on just how little Isabella thought of herself at the minute.

    Isabella finished her breakfast and was soon asking Amanda to place her back in the cuffs so she could start her work.

     “I’m not sure Lady Rebecca will want you back in those restraints Bella.” Amanda tried to argue.

     “I deserve to be locked in them after everything I did, so please put them back on me.” Isabella pleaded.

    Amanda did as she was asked and Isabella was soon locked into the cuffs again as she wandered around helping Amanda clean as best she could with her arms and legs locked together like they were.



Chapter Six: The perfect maid.

    Isabella soon earned her way out of the cuffs and she became good friends with Amanda and the two cooks who were called Clare and Jane. Isabella would help out in the kitchen when she wasn’t helping Amanda to clean the castle. She also thought that she’d been given a couple of tests to see if she would try to escape, but she was finally happy doing what she loved, being a maid. She still got punished every once in a while, but for the most part she was the perfect maid and Mistress Anne had little to do with her.

    It had been just over eight months since Isabella had been let out her cell and put to work and she thought her life was perfect all apart from the guilt she still carried over Mistress Rachel and what Mistress Anne planned to do when she finally grew tired of her.

    Not having seen much of Mistress Anne and Lady Rebecca for the past month due to them being away on business a lot, Isabella was worried when she found Lady Rebecca wanting her to go somewhere with her.

     “Isabella, come with me, Mistress wants a word.” Lady Rebecca said one morning as Isabella was helping Amanda to clean.

    Isabella was worried as Lady Rebecca only ever used her full name when she was in trouble for something. She followed Lady Rebecca to Mistresses office and entered after knocking and waiting for permission to enter.

     “Please come in and take a seat Isabella.” Mistress said in a kind sounding voice as she waved Isabella over to join her on the sofas over near the large window that over looked the valley below the castle.

    Isabella sat down looking nervous as she watched Mistress pour her a cup of tea out and then hand it to her, but she never made herself one, which should have let Isabella know something was wrong.

     “Thank you Mistress.” Isabella said to be polite just before she took a sip from the cup and thought it tasted a little bitter for her taste. She was soon more worried about other things though; as the room started to spin and Isabella remembered Mistress taking the cup out her hands just before she passed out.

    Isabella woke to find herself strapped to a weird looking table with her arms stretched out to the side like she was lying on a cross shaped bed. She started to remember Mistress being nice to her just before she passed out, from some drug Mistress must have given her Isabella worked out.

     “Good you’re finally awake.” Mistress said as her head came into view above her. “I thought I might have killed you before we actually killed you.” Mistress added. “I would have felt bad if I’d gone to all this trouble, just to kill you before we got to use it.” She said with an evil sounding laugh while waving at the room they were in.

    Isabella was suddenly wide awake as she looked around the room and realised that she’d seen a place like this in the movies when they were giving a prisoner a lethal injection. Isabella tried to get loose, but she was strapped down to well for that, she could hardly move at all, and she now noticed the IV’s going into her arms and her bladder suddenly let go of whatever fluid she had left in her body due to her being terrified of what they were about to do to her.

     “Please Mistress, I don’t want to die.” Isabella said in a panic as she struggled to get loose again.

     “But you did when we first caught you, I’m just giving you a little help now, and it will be painless, or so I’m told.” Mistress said with a pout.

     “I’ve changed my mind and I want to live now and serve you as a maid, so please don’t kill me.” Isabella sobbed.

     “When I first found out what you were planning to do, I felt a little happy about you feeling so bad, but then I thought that it was too easy for you, so I wanted to give you something to lose, and over the past eight months I’ve seen how much you’ve come to love being my little pet maid, so now I feel that you have something to lose, so this is the day you finally get your wish to die.” Mistress said with a snarl. Do it now before she whines some more.” She added as she pushed a large red button and Isabella watched as a line of syringes empted and she could feel liquid flowing into her just before she started to feel sleepy. Isabella tried to fight it, but her eyes just got far too heavy for her and she was gone. The last thing Isabella remembered was Mistress being right about it not hurting.

    Isabella thought the afterlife sucked as she could still feel pain and there wasn’t any bright light to head into, just some beeping and the feeling of something heavy and tight compressing her chest. Isabella slowly opened her eyes expecting to see a fiery pit or white fluffy clouds, but all she saw was a posh looking bedroom and Mistress sat reading a magazine with Lady Rebecca sat next to her reading a book.

     “I’m not dead?” Isabella asked in a croaky voice. As she tried to look around the room a little more, but her chest was hurting to much so she gave up and laid her head back on the pillow again.

     “We never planned to kill you silly.” Rebecca giggled as she came over and sat on the edge of the bed. “We just needed you to finally admit to yourself that you wanted to live.” Rebecca started to explain.

     “I’m sorry I put you through all that Bella, and I hope you will want to stay on as my maid once you’ve recovered.” Mistress said as she came over and sat on the bed next to Rebecca.

     “Recovered from what?” Isabella asked.

     “We decided to treat you to a larger set of breasts because the hormones weren’t cutting it in that department and I like my maids to look sexy in their uniforms.” Mistress admitted with a grin.

     “Why would you want me around after what I did to your sister?” Isabella asked with tears in her eyes. “Why would you want to be so nice to me?” She snuffled.

     “I was angry with you for a short time, but as I watched you try to destroy yourself over the guilt you were carrying, I realised that you never would have done anything to hurt my sister, and Rachel made me promise on her deathbed that I would do all I could to help you get over the guilt and then help you to become a maid and the girl you were so desperate to become.” Mistress explained with tears of her own rolling down her cheeks now.

     “Will I still be your little pet?” Isabella asked.

     “You will always be my little pet, but a much loved one that I will always protect.” Mistress promised as she leaned down and kissed Isabella on the forehead. “I do need you to prove that you belong to me though.” Mistress said.

     “Please name it Mistress and I will do it gladly.” Isabella said.

     “I want you to place this around your neck to prove that you belong to me.” Mistress said as she held up a stainless steel collar to go around Isabella’s neck. “Once it’s closed around your neck, it can’t be removed, not even by me.” She warned.

     “I except your terms my Mistress.” Isabella said as she took the collar out of Mistresses hands and placed it around her own neck and closed it with a final click.

     “Now you really are my little pet.” Mistress smiled as she kissed Isabella on the forehead again.

    Isabelle was bed ridden for a couple more days, but she was well looked after by Amanda, and Clare and Jane called in to see her a couple of times. Once she was well enough to work again, Mistress ordered her to only do light duties for a month or two until she was fully healed.

    Isabella was impressed with her larger breasts and she loved to be able to look down and see the large cleavage through the heart shaped gap in her new maid uniforms, even if it did take her some time to get use to the extra weight on her chest, and she couldn’t go without a bra, and she always wore a sports bra to sleep in, as well as a corset now. Mistress had decided to start training Isabella’s waist, so she would look even better in her uniforms.

    Even though Isabella was only a maid, she was still well loved my Mistress and Lady Rebecca, as well as the other staff in the house, and she would travel all over the world with Mistress and Rebecca. Mistress had sorted Isabella out with some new ID in her new name of Isabella.

    Isabella got another surprise a couple of years after getting her breasts done, when Mistress paid for her to have the final surgery to make her a complete woman down below so she no longer needed to wear the chastity device she’d been wearing for the past three years.

    Once she was fully recovered she started to take an interest in the Dom side of her Mistresses business, but she still liked to play the sub in her Mistresses and Lady Rebecca’s games.

    Isabella never bothered to look up Ian’s parent’s as he had died that night on the bridge like Mistress had said, but Isabella had lived on and finally found a place to call home, and she had two loving Mistresses to take care of her. She just wished that Mistress Rachel could have seen how she turned out, but she hoped that maybe she was being watched over from some kinky little part of heaven.

The End.

 

Story by SaraUK

 

Edited and Posted by SamanthaK

    EDITORS NOTE: Please Comment and/or leave Kudos and let Sara know you like her work please, Any comments on spelling, grammar or the layout of the story please PM me “Samanthak” not Sara. Thank you


Source URL:https://bigclosetr.us/topshelf/book/42295/sentenced-life