Betty Pearl's Sissy Stories 20.1
Menu => Active Sissy Stories => Topic started by: pollyannauk on September 15, 2021, 01:40:59 PM
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Hi all, This is my very first story so please go gentle with me. I have read so many on this site for a while now and wanted to give it ago myself, so here goes......
I was at home getting ready to go out for another date with Gerald, We going to a nice hotel for lots of hot sex again tonight and I really need this after the week I have had. I have worked so hard to get my sales done this week only for it to fall through at the last minutes, so am really looking forward to getting all dressed up for a lovely evening. I bought myself a whole new outfit especially for this occasion, I bought new black fishnet stockings, red satin bra and matching panties with a nice black dress. I was just in the middle of attaching the stockings to my suspender belt when the phone went. Bloody typical as if these are not hard enough to attach I thought. I quickly ran to grab the phone, having have my suspenders attached and half dangling and noticed it was my mother calling me.
“Hi mum sorry I can’t speak for long I am in the middle of getting ready to go out” I said.
Oh going anywhere nice tonight my mother asked. “I am going out with Gerald again, he taking me to a nice restaurant and then we staying over in a nice 5 star hotel for the weekend so I am in a bit of a rush”
“That sounds lovely dear and how many dates have you been on with him now, do you think he is going to be the one for you to settle down with, have you started any discussions with him yet on what is expected of him dear”. I knew exactly what my mother was getting at and just wasn’t ready for what my mother wanted. “No mother Gerald is not that sort of guy he is just some one to have fun on with the weekends”. “That is totally fine for you as you should go out on dates with men but you know the rules for our family and you need to be married before your 30th birthday which is just over 1 year to go so you better start finding a candidate worthy of marriage soon or you know that great Auntie Glenda will find one for you and I’m sure you much prefer to select your own Husband rather than have one selected one for you”. My mother has been on at me constantly about this but I am just not ready to settle down and get married. “I know mother I just haven’t really put much thought into it and I really need to go and get ready for my date and I am going to be late if I can’t finish getting ready” “Well just think darling if you had a nice sissy husband you would have help getting ready and things would be a lot easier for you and don’t forget you still be able to go out on dates as I would gladly babysit for you but first we just need to find a suitable candidate and get him properly trained before he is introduced to the rest of the family”. “ My mother was right time was running out and I would much rather find my own Husband that having Auntie Glenda finds one for me who know what sort of wimp I will end up with. At least this way I can find someone I love and that loves me even once he realises what is in store for him. “OK mother look I really must go now otherwise I am going to be so late but I will go out next week with a few girl friends and see if I can find a suitable candidate”. Gerald is definitely not going to fit in with the family rules but it would be nice to have someone to properly love me. “OK that is excellent dear I will let Auntie Glenda know that we have had a little chat. Have a great evening and will catch up again next week”.
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Week 1 – 52 weeks to go till I am to be married.
“Hi mother”, Hi Sophie how are you today, have you had a good week” have I had a good week, it been a busy one for sure, work has been so hard and I haven’t touched any of the washing I have piling up, maybe soon I won’t need to do any more washing or Ironing, that be a good thing but Gerald is definitely not going to assist with it that for damn sure. However it would be fun to see him dressed up and doing my washing even just the once.
“It’s been busy mother I had lots going on at work but I did get out with the girls however funny thing happened the other day my car broke down and a young gentlemen stopped to help me and he was awfully polite and seems like a nice guy so I thought maybe this is fate and I offered to take him to dinner next week which he has excepted”
“Oh that sounds fantastic darling. I would love to hear more about it but I am looking after your nephew for the next few weeks as your sister is going on holiday so I’m going be rather busy, I can’t be too long tonight as I left him in the bath alone”.
My sister Fiona is 12 years my senior and has always been my Great Auntie’s favourite, she loved to assist with petticoating my brother Thomas and was always coming up with ways to get him punished or given more corner time. Her own Husband David was only 19 when they married and he has spent many months under the watchful eye of my Auntie Glenda’s and along with their son Frank while he was growing up who once he is old enough will be married to a daughter of one of Auntie Glenda’s close friends just like David was to Fiona.
“I’m sure he will be OK in the bath alone mother he is after all 15”.
“Sophie you know fully well that when a male in this family is to have an early bedtime he is be treated as nothing more than a toddler and I expect you to follow the rules with your new chosen Husband whether you like it or not or you may find yourself over your great Aunt’s knee understood”.
I never was a great fan of the rules for my family, when I used to see poor Thomas going through his early days of training when I was a young girl I would often say I not sure he has done much wrong and often feel sorry for him, I would say this is not going to happen to my husband when I have married or my son but over the years and many a sore bottoms I have learnt that it not as easy as that and my Aunt Glenda will make sure of it. These rules have been in place for many years and is a big tradition in my family and although I like idea of having a submissive husband I not sure I am ready for this but as my mother keeps pointing out time is running out before Aunt Glenda takes over the planning for me.
“I’m sorry mother yes of course. Perhaps you should go and check on Frank”
“Tell you what why don’t you drop me an email after the date and let me know how things go. I won’t tell Auntie Glenda just yet I don’t want to get her hopes up, do you still have the apron your brother in law David left behind”.
Ha the apron he left behind thinking that he wouldn’t need to wear it any more if accidentlyly left it at mine. not realising he was still in his early days of his training, more fool him my sister made sure of that the next apron she bought him was a lot more frillier and covered his whole body not just the bottom half.
“Yes mother I still have it”
“good maybe invite him back for coffee and see if you can get him to wear it for making the drinks. See how it takes it”. Yeah well if he does wear it I think I will get him to do the washing also, save me having to do it next day.
“Will do mother, speak soon love you”.
“speak soon darling I hope it goes well for you, now I best get Frank bathed and put to bed love you.” Put to bed it not even 7pm, many a nights I would see my brother put to bed while Fiona and I would sit up till all hours. He used to complain he could still hear people playing outside but my mother would just say rules are rules in this household and if you don’t like it you welcome to complain to your Great Auntie Glenda. Poor Thomas would soon lay down and go to sleep.
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poor Great Aunts they never get to rest. Depose them and replace them with a rotating council of grand mothers. :) *hides*
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Week 2 – 50 weeks to go till I am to be married.
Hi Mother,
I hope you are doing well and Frank is behaving himself for you.
I had the date and thought it went really well, his name is Mark and he is 21 years old. He is studying for a Health and Social Care Degree. He is an only child who used to live with his Mother and Father till they separated and his Dad left 5 years ago and has not been back in contact. Currently he is sharing a house with a few friends but he has just been recently made redundant so he is looking for another job otherwise he might have to move back with his Mother but this would mean giving up his Degree.
I invited him over for coffee which he was happy to join me for.
As suggested I asked him to make the coffee and for him to wear the apron to protect his trousers to which he did, I even asked him to bring me the apron so I could tie a nice bow for him. I asked him to turn around and then made sure I slowly measured the apron around his waist before tying a nice big floppy bow and then sent him off to make the coffee. Oh Mother he looked so cute, I could picture him already in a lovely satin maids uniform pouring us tea just like Father and Thomas but I don’t want to scare him away yet.
I have invited him around next Saturday to spend the day together, unbeknown to him though I plan to have him doing my washing and ironing and see if he will happy help out with the house work. I am not going to let him going exploring upstairs just yet though. , I want to see I can get him to hang out my washing on the line with his apron still on. I am also going to make sure that I have some underwear ready to wash and see if he will hand-wash this in the utility room, I will set up a camera to watch how he is with my undergarments, how much of an interest he will take, hopefully he will show me exactly what I want to see. I will send you a copy to watch.
I want him Mother I do, he is perfect so polite and If all goes well and he hasn’t found a job soon I am going to invite him over again the following week and discuss about his living arrangements seeing as his saving aren’t going to last forever. I will then sit him down, making sure he still has his apron on and ask him how he feels about me and see what he says. I plan to tell him about our family traditions and that I want a husband but a submissive husband and that if he decides to move in with me to be together that I will be going to sissify him and not just in my household but he would be expected to be a sissy during, family and friends visits and also any family gathering. He can still go to Uni and study wearing male clothing but I expect him to wear his sissy underwear underneath, anyway Mother I am getting ahead of myself and still need to wait to see how he turns out next week, he might not even be suitable.
Take care, love you loads, speak soon.
Sophie.
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Good evening Sophie,
This all sounds wonderful darling, Mark does sound really nice, I can’t wait to meet him and also having the privilege of having him over while you go out although lets not rush things just yet. Like you say lets see how next weekend goes, He sounds like a sensible boy and quite intelligent and I expect he probably helped his mother out with the house chores once his Father left if not even before.
I love the fact you already have Mark wearing an apron but I am going to be sending over a more elaborate one for you which will be perfect for him to complete his house chores wearing. It should hopefully fit. I have attached a picture for you but I will pop it over before next weekend.
If you know his shoesize or can try to guess them I can get Fiona to send you over a pair Of David’s flats to wear also, just wait until he has put the washing out and got mud on his shoes and then say it all you have and you don’t want muddy shoes on your carpets or for his own safely don’t want wearing just his socks. Make sure you have him doing the washing first so you can have him change his shoes as soon as possible. This way you can get an early indication of how submissive he is.
It going to be an interesting conversation with him when you explain your going to sissify him if he wants to become your husband, but I can help you plan for that soon, the last thing you want is for him to run of before you have a chance to lock off his male clothes apart from what he allowed to wear for University. I look forward to hearing how it goes next week, give me a call Sunday. In the meantime I will give Aunt Glenda a call and let her know how things are progressing.
Loves you loads darling.
Mother.
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I'm very sorry not posted any more on this in a while, have been completely snowed under with work, will hope to post more updates a lot quicker soon.
Please enjoy.
Well today has been wonderful Mark came over as planned. I made sure I dressed up nice for him today, wore my black boots, with black tights, nice faux leather black skirt with a white blouse, camisole and bra and put my hair up in a bun. Mark was wearing black jeans and a t shirt but it didn’t take too long to get him into his pinny.
I explained to him that I have a lot of house work to do today but if we get out the way we can relax later and get a take away and then watch something on Netflix. I said to him
“it would be best if you wear the pinny to help me clean and do the washing etc. as it will help protect your clothes, so if you could fetch it from the kitchen then we can make a start”.
Mark didn’t argue and came back with the new pinny saying “this is all I could find”, to which I replied
“ah yes the other one must be in the wash, never mind this will protect your clothes better, turn around so I can help you get it on and tied properly”.
To my surprise Mark didn’t put up any fuss and just let me put him into his new pinny. I wondered if he would be so well behaved when it came to his skirts and dresses, not that I really cared as he is going to be my sissy husband soon whether he likes it not, I just need to take things slowly so as not to scare him away.
Aunt Glenda is not going to allow me access to receive my trust fund, unless I am married and if my husband is proven to be a complete sissy and can show that he is going to obey all our family traditional rules without complaint. These rules have been in place for 100’s of years and even though I don’t fully agree with them I am not going to be losing out on my money. If this means I need to have a sissy for a husband then so be it but I am going to make sure it is one of my choosing.
Once I had Mark dressed into his pinny I asked him
“if he would be a dear and help me put on some washing”
I had already moved the washing basket down to the utility room for him and explained to him
“that if he could sort the dark from the lights and then put on a dark wash, I will be in my office doing some paperwork but just give me a knock on the door once finished, it’s just down to the hall on the left”.
Unbeknown to Mark I was going to watch him on my camera to see how much of a good job he did with the washing and if he took the care that I require from him.
I decided last week that If I am looking to own a sissy of my own soon I should have camera’s installed in my house, so just last week I managed to get a camera setup in every room and also one in the garden but made sure that they were hidden. If things go well today and I manage to talk Mark into moving in I want to watch his every move as his sissificaton is taking place and each time a new outfit or rule is introduced I want to make sure that he is obeying me and not just when in my presence otherwise I will never pass him off as ready before my marriage.
Luckily though I was pleasantly surprised to see he took a lot of care and every so often he would also stop and hold out his apron to gaze at it or feel it all over, Oh this is too perfect I thought any real man would of taken it off and put it back on when leaving the utility room or they would of just said I’m not wearing that full stop but not Mark he was good as gold.
Once he had finished I watched him as he walked out of the utility room and down the corridor to my office and politely knocked on my door.
“it’s open”
I said. Mark popped his head around the door and was just about to speak when I said
“Don’t be shy Mark you can come in”.
As he walked in wearing his apron looking all submissive, I could picture him standing there in a full maids uniform and performing a curtsy for me while waiting further instructions.
“Have you put on a dark wash” I asked.
“Yes” he replied.
“Great thanks Mark, unfortunately I have some more work to do in my office, would you be okay to bring in the washing that is on the line, you will find the basket in the bottom left cupboard of the utility room”.
“Em OK no problem” he said and off he went.
I continued to watch him as he walked away down the corridor and back into the utility room then searched for the washing basket, I thought to myself I am going to need to teach him to walk properly and to bend at the knees with his legs together but for now lets just get him out of the them trainers and into some nice low heeled shoes that will sound so much better on the hardfloor.
I watched him go outside and walk down to the washing line and start taking down the washing, while he was doing this I noticed straight away where I left the sprinkler on earlier the grass was nice and wet and would make sure this would make Mark’s trainers nice and muddy so I can get into the flat heels but what I didn’t account for is that his trousers at the bottom were also muddy too. This is too perfect I thought this must be fate, I will have to get him out of them trousers as well lets just hope his legs are not too hairy, well if my plan works they won’t be for much longer anyway.
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Great start, thanks for the latest installment. I hope he will in time meet his great aunt and show his submissive side. Mature ladies are really my thing!
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I am sorry it has been 3 months nearly 4 since my last post. I can see now why writers don't post for a long time, Work and my personal life has been extremely busy but I will try to post more of this story asap. I do not want to rush this story and have plenty of ideas where to go with it but this ideas will take time, this is not going to be a rushed transformation.
Week 3 – 49 weeks to go till I am to be married
Well today has been wonderful Mark came over as planned. I made sure I dressed up nice for him today, wore my black boots, with black tights, nice faux leather black skirt with a white blouse, camisole and bra and put my hair up in a bun. Mark was wearing black jeans and a t shirt but it didn’t take too long to get him into his pinny.
I explained to him that I have a lot of house work to do today but if we get out the way we can relax later and get a take away and then watch something on Netflix. I said to him
“it would be best if you wear the pinny to help me clean and do the washing etc. as it will help protect your clothes, so if you could fetch it from the kitchen then we can make a start”.
Mark didn’t argue and came back with the new pinny saying “this is all I could find”, to which I replied
“ah yes the other one must be in the wash, never mind this will protect your clothes better, turn around so I can help you get it on and tied properly”.
To my surprise Mark didn’t put up any fuss and just let me put him into his new pinny. I wondered if he would be so well behaved when it came to his skirts and dresses, not that I really cared as he is going to be my sissy husband soon whether he likes it not, I just need to take things slowly so as not to scare him away.
Aunt Glenda is not going to allow me access to receive my trust fund, unless I am married and if my husband is proven to be a complete sissy and can show that he is going to obey all our family traditional rules without complaint. These rules have been in place for many generations and even though I don’t fully agree with them I am not going to be losing out on my money. If this means I need to have a sissy for a husband then so be it but I am going to make sure it is one of my choosing.
Once I had Mark dressed into his pinny I asked him if he would be a dear and help me put on some washing. I had already moved the washing basket down to the utility room for him and explained to him “that if he could sort the dark from the lights and then put on a dark wash, I will be in my office doing some paperwork but just give me a knock on the door once finished, it’s just down to the hall on the left.
Unbeknown to Mark I was going to watch him on my camera to see how much of a good job he did with the washing and see if he took the care that I require from him.
I decided last week that If I am looking to own a sissy of my own soon I should have cameras installed in my house, so just last week I managed to get a camera setup in every room and also one in the garden but made sure that they were hidden. If things go well today and I manage to talk Mark into moving in I want to watch his every move as his sissification is taking place and each time a new outfit or rule is introduced I want to make sure that he is obeying me and not just when in my presence otherwise I will never pass him off as ready before my marriage.
Luckily though I was pleasantly surprised to see he took a lot of care and every so often he would also stop and hold out his apron to gaze at it or feel it all over, Oh this is too perfect I thought any real man would of taken it off and put it back on when leaving the utility room or they would of just said I’m not wearing that full stop but not Mark he was good as gold.
Once he had finished I watched him as he walked out of the utility room and down the corridor to my office and politely knocked on my door.
it’s open I said. Mark popped his head around the door and was just about to speak when I said Don’t be shy Mark you can come in. As he walked in wearing his apron looking all submissive, I could picture him standing there in a full maids uniform and performing a curtsy for me while waiting for further instructions.
I asked Mark if he has put on a wash and then told him unfortunately I have some more work to do in my office, would you be a dear and bring in the washing that is on the line, you will find the basket in the bottom left cupboard of the utility room.
I continued to watch him as he walked away down the corridor and back into the utility room then searched for the washing basket, I thought to myself I am going to need to teach him to walk properly and to bend at the knees with his legs together otherwise I will never be able to pass him off as suitable and get hold of my inheritance but for now I just need to get him out of the them trainers and into some nice low heeled shoes that will sound so much better on the hard floor.
I watched Mark go outside and walk down to the washing line and start taking down the washing, while he was doing this I noticed straight away where I left the sprinkler on earlier the grass was nice and wet and would make sure this would make Mark’s trainers nice and muddy so I can get him into the flat heels but what I didn’t account for is that his trousers at the bottom were also muddy, too. This is too perfect I thought this must be fate, I will have to get him out of them trousers as well lets just hope his legs are not too hairy but for now if they are they will have to do.
As Mark walked back I could see he was a lot muddier than expected, I rushed out of my office to meet him as I didn’t want him to make too much of a mess on my hallway floor although I did wait till he was at least half way up the hall. Stop right there I shouted at him, just look at you, your all muddy. I took the washing basket from him and said I’m sorry it my fault, just look at you. Mark looked down and could see he was caked in mud and just looked up and said he was sorry. Never mind it was really my fault I forgot the sprinkles were on this morning. Here let me help you. I knelt down in front of him and untied his shoes and removed them. Your trousers are very muddy we going to have to remove them too. I don’t have anything to replace them with but don’t worry it quite warm today and if your shy your apron should cover your underwear. As I was saying this I had already started to lift his apron and was starting to unbuckle his belt. He put hands down to stop me but I just told him not to be silly and carried on. I slowly unbuttoned his his trousers and let them fall to the floor then explained that not too worry we can always wash and dry them before it time to go home. I left him standing there in just his apron and t shirt with bare legs showing, I didn’t get a chance to get a full look at his legs but from what I could see now I could tell they were quite wispy and not very hairy at all. While I take the washing up stairs and put it away would you be a deer and give this mud and sweet and then a quick mop over the floor. You will find everything in the utility room cupboard. If you take your muddy trousers and shoes with you once I finished upstairs I will take a look see what we can do with them. Mark agreed and walked off as I did I said and be careful on the hard floor I don’t want you slipping over in just your socks.
I went upstairs and got David’s shoes, I do hope these fit but these will do until I can properly look at his shoe size later. If I know he was going to get his trousers all muddy too I would of asked for a skirt to see how easy I could get him into it, oh well plenty time to plan for that eventually.
I went downstairs and could see Mark was already on the mopping stage and I could see he had a done a really good job of getting rid of all the mud. Once he has finished I praised him on doing such a good job and that I was really pleased. I then explained to him that because I didn’t want him slipping on the floor I found him some shoes upstairs. He did say they are girls shoes but after I had shown him that only had a 2 inch heel and it just me and him here no one is going to know he agreed to wear them even just for his safely.
I asked for him to come into my office as the hallway was quite wet and then I knelt down to help him into them and surprisingly they fitted quite well, As I put his 2nd foot in all I could think about was the fun I was going to have putting him into all sort of different shoes and boots, some with locks into his not to distance future. I asked Mark how they felt and he replied they actually seem quite comfy. I said it will be good for him to practise walking up and down in them for a few minutes in the office, just walk to the end and back while I continue my work then we can a nice well earned break. I sat down and looked over as he actually started walking up and down in the heels, to think it day one of his sissification he doesn’t even know that he has started on this road I have explained anything to him and already he is wearing a frilly apron and 2 inch heel shows and practising to walk. If I can get him to move in then next few months could turn out to be quite exciting for me and very humliating for him.
After a few minutes I told Mark he could stop now and we shall go find something to snack on and have a drink and a little chat.
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A slowly developing story - - -
Without a TITLE ?
Or maybe "My very first story" is a title unique in itself - - - ?
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I love this story, you are a very talented writer. I hope this story continues, lots of weeks to go and lots of ideas and situations to explore, I thing this story could be one of the greatest. Love Marci
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Thank you for your kind comments, lovellace and BabyLock and especially to sissy marci, as It says in the title this is my very first time at writing a story so not sure how it would be received.
Here we go finally a month later another installment, sorry it short and sweet but I do promise not to leave it so long next time, hope you like it.
I led Mark into the kitchen and said to him take a seat at the table and I will make you a sandwich seeing as you have done quite a bit of work already today. As he sat down I noticed that his apron had got all caught up. I turned around and explained to him that when wearing a nice apron you need to make sure that you smooth it out before you sit down otherwise it going to get all bunched up and creased. Mark stood up again and tried to smooth down the apron before sitting again but I wasn’t satisfied and asked him to stand again but this time slowly bring your hands behind you and as you go to sit smooth out the apron. Mark did as he was told so submissively without any complaint what so ever so I made sure I praised him for this, I wanted to say good girl very well done but I didn’t want him getting confused and start asking questions. Instead I told him that was much better, see how it now not all bunched up.
“Tell you what just to make sure that you have it why don’t you do it a few more times while I fetch us something to eat”
I got the butter and cheese and lettuce out of the fridge and the bread from the bread bin and turned to look at Mark slowly sitting down and then smoothing out his apron then getting back up again, still no complaints and still behaving as I need him to be.
I left him to this while I continued to make the sandwiches and then told hiim that he can stop.
“Mark I didn’t expect you keep going all this time but it was good that you did”
I handed Mark his sandwich and sat down opposite him. I then waited for him to take a bite and then decided to ask him some questions.
So tell me Mark how has today been for you, have you been okay being my little house maid doing chores today is this what you expected you would be doing when you came over. Mark went to speak but he was still had food in his mouth, so I said it OK finish your food before answering. I took a bite of my sandwich and then waited.
Mark then finish his mouthful and after swallowing explained that it has been nice being here and to be honest he wasn’t sure what was going to happen today, It’s not often that a lady invites him over for the day and that he understood chores can pile up when busy with work so he was happy to help with them.
I thanked him and said “ it has been a great help and if you wouldn’t mind after lunch I do have a lot more work to do today and would love if you would help out with some more of the chores, then later like I say we can relax together and watch a movie or something, would that be OK with you”
Mark finished another bite of his sandwich and then said “that he would be happy to help me out with them”.
I explained that is great makes me really happy, your like my own little maid. Tell me what are you like at hand-washing and also ironing?
Mark finished his next bite while admiting a little laugh, I asked him what was funny and he said “well I’m not really a maid more of a butler I guess”.
“oh really is that so, do you think a butler would wear such a feminine apron or those 2inch heels” I said while making a joke of it myself.
“well no I guess not” he said,
“To be honest I think it suits you, it looks nice, tell you what finish the last few bites of your sandwich and then stand up so I can take a good look at you. I waited for Mark to finish up and then told him to stand and come over to me. As he stood up I told him to smooth out his apron then push in his chair and then come stand in front of me.
Mark walked over and stood in front of me with his eyes cast down at me, I told him to turn around so I could check on the bow and as expected it has come a bit loose and ruffled up.
“this bow needs redoing it looks all loose” said to him while undoing the bow and tying it again, I then asked for him to turn back around.
“Now take your hands under the apron and loosely bring it out again so it will flounce up a bit better”
I watched Mark while he did this very feminine manoeuvrer and then asked him to walk over to the back of the kitchen and then asked for him to turn around and smooth out the apron again.
“still feeling like you are the butler” I asked while have a little giggle in my voice.
“I guess not” Mark said while having a little giggle himself.
“OK that is enough break time, I have some work to attend to and you my little maid, have some more chores to complete if that is okay with you”
“I guess so”
OK firstly if you wouldn’t mind making me a cuppa tea, and brining to my office, you can make yourself a cuppa tea, coffee or have juice which ever you prefer. Once you have made the drinks the dark wash needs to come out and will be ready for ironing. Are you going to be okay with ironing?
“Yes I learned how to iron when I was younger by my mother”
“OK that is great, OK make the tea, bring it to the office then let me know once you have completed the ironing, you will find the iron and ironing board in the cupboard by the stairs and you can set it up here in the kitchen okay”.
“okay no problem” Mark said.
“brilliant thank you so much for this Mark I really appreciate the help today who knows I might need to hire you as my full time house maid in future now get to work” I said with a giggle.
“Yes miss” mark said jokingly but if only he knew what his future had in store for him.
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I went back to my office and sat down feeling quite pleased with myself and switched the camera over to the kitchen so as I could keep an eye on Mark while he prepared the tea. In such a short time I had made quite a bit of progress with Mark and wondered how soon I could start him properly on his road to sissification. I really don’t want to lose him, he seems perfect for this role just not sure how he is going to react when he finds out exactly what I have planned for him.
I think it time for a quick call to my Mother for some advice.
I waited for Mark to bring my tea, he knocked on the door and I told him he could enter and pop the tea down on the desk for me. I advised him that the hangers were also in the cupboard under the stairs and said if has any problems give me a shout, to which he replied he will do and off he went.
I took a sip of my tea see how it tasted which was really good and then dialled my mother.
“Hi Mother are you free can you speak for a bit”
“Yes Sophie course I can, what’s up”
“Well I have Mark here Mother like I planned”
“oh good, how is it going, did you get him in the pinny and shoes”
“Yes Mother he looks really good and well”
“did he give you any grief at all, when you asked him to wear them”
“No he didn’t give me any grief, in fact I even joked about him being my little house maid while we had lunch to which he said he was more a butler than a maid of course I put him straight about how a butler would not wear such a feminine pinny or 2in heels”
“oh this is wonderful darling, really glad to hear, so where is he now”
“he is currently in the kitchen ironing”
“oh well done, so what else have you had him doing”
“He got the washing from the line, after the sprinklers had been on which is how I got shoes removed as they were quite muddy. he then cleaned the hallway of the mud, put of some more washing, before we had lunch”
“Very good do you have anything planned for the rest of the day/evening”
“well I still have to see how he will react to hand washing some of my lingerie after doing the ironing then I plan on sitting down and watching a movie and order some pizza perhaps”
“this sounds really good, you going to keep him in the pinny and shoes”
“well I was thinking that but only because I don’t really have anything else for him wear”
“Oh, I see”
“His trousers got all muddy earlier too and he had to take them off but I haven’t put them in the wash yet and he hasn’t mentioned it so was hoping could make an excuse that they won’t be ready till morning and could see if I could get him to stay over for the night, In the spare room of course”
“I see, well tell you what I have some of David’s nightwear here for when him and your sister stay over, it’s washed and clean, I could pop it over for you and you could get Mark to wear that later”
“I’m not sure mother, how sissyish is it, I don’t want to spoil things and have him run off in his dirty clothes”
“Well yes it very sissyish, it a cute hot pink baby doll, it has thin straps and lots of lace, it also had a pair of hot pink panties with white polka dots and cute little white socks with hot pink trim and a training bra also in hot pink but not sure you want the bra just yet, everything else will be fine” my mother laughed.
“jeez Louise Mother than all seems a bit over the top, I was hoping for something more on the lines of a plain long nightie perhaps”
“nonsense it quite plain complain to a lot of his other outfits, David does have some plainer ones, but your sister much prefers him kept as frilly as possible nowadays especially when visiting friends or family, perhaps once you get Mark moved in your sister can donate some of David old clothes to get you started before you get him properly measured for his own.
“I’m really not sure Mother, this seems quite a jump from an apron”
“well the panties are more like little shorts so shouldn’t be too hard to get him into them and the baby-doll you can just say it for when you have your niece stays over and unfortunately it all you have, have him take a bath, not a shower, make it a nice bubbly bath, as a sissy he needs to get used to taking them anyway, then while he is in the bath put all of his clothes in the wash so he will have no choice but to wear them, say it all you have and it’s either that or being naked in a towel for the evening, be firm on getting him to wear it if needs be then once he is dressed play on how cute he looks, have fun make him feel relaxed, show him affection, for now you need to gain his trust so as you can move onto the next step, you can worry about how he reacts when it comes to wearing his first skirt, dress or the first time he is to wear a nappy and that you expect him to use it” my mother laughed, a lot harder this time.
“OK I will hopefully he will be done with the ironing soon and then I will send him to the utility room out of sight and then it should be safe for you to pop over and drop them off”
“oh so I won’ t get to meet young Mark today then”
“No mother I don’t want to rush things it might scare him off”
“good point plus I would much rather meet him a nice frilly dress perhaps either in a lovely maids outfit or a nice cute toddler dress with a nappy”
“I tell you what mother, if I can get Mark to agreed to be sissified and become my husband, I will let you meet him in a lovely full satin maids uniform, he can serve us tea then you change him into a toddler outfit”
“and put his nappy on?”
yes you can put his nappy on, you can even bath him, but you need to give me time to get him ready for meeting people”
“OK so lets say 3 weeks from now, if all things work out”
“I,’m not sure Mother will see I will try but not sure if he is going to say yes or not”
“well lets see how well he does with his new nightwear for tonight then, I will come over in an hour or so, I will give you a message beforehand”.
“OK thanks Mother, love you”
“love you too sweetheart”
I hung up the phone and sat back to watch Mark on the camera, I never really had any work that needed doing today but I wanted to see how Mark would react being on his own left to get on with the chores and to be honest this has gone a lot better than expected. I'm not sure how he is going to like his new nightwear tonight but I am looking forward to seeing him dressed later on.
While sitting back nicely relaxed I played the camera from when we had lunch and watched him sitting and standing while smoothing his apron, I saved a clip and also saved a clip of when he had me tie his bow again and sent these over to my Mother via What’s app, asking what she thought.
She replied quickly with a smiley face saying practise, practise, practise, to which I said replied back with another smily face see you soon.
I left the office and went to see Mark, he was still ironing, as I entered the kitchen I asked him “how is my little maid getting on” with a giggle.
“just finished the first 2 blouses miss” he joked.
“OK what a good little maid you are, I am just popping upstairs to sort out a few things, won’t a tick, please carry on, there a good girl” I giggled again.
“very funny” Mark said and laugher also.
I went upstairs into my bedroom and sorted through some of my lingerie, they were all clean already but Mark isn’t to know this, I picked out a few pair of stockings and couple of matching bra, panties sets that Gerald likes in satin, silk and lace, Not sure how he would react if I told him about my families traditions, don’t think be wise to mention, I love it when we sleep together he is so in control but I don’t want a man like that in control of me all the time, just when I demand it, I should give him a call soon I think.
I went into the spare room to check everything was ready for Mark to stay, the The room is self is quite feminine it has a large king size bed with full satin sheets and duvet, pillows, currently in glorious baby pink. The bed has a large headboard in white and the Divan sits quite high of the floor with a baby pink valance going round the bottom. The bedroom it’s self is quite large and the bed is against the back wall, the room is painted pink and has a boarder of a floral pattern going around the top edge. The curtains are pink and the window is quite large that opens out. The carpet is a light grey with grey wardrobes and a grey desk which has large mirror on top, all the drawers and wardrobe are currently bare.
I don’t often have anyone stay other that Frank but if all goes well this will become Marks room, I have another spare room but this is empty and I just use it for storage, however this will be turned into a nursery for Mark to be used for when he has his toddler and baby days but for now this is where I plan to store Mark’s clothes, I will need to put a lock on the door beforehand though, it will need one for when it’s a nursery anyway.
I closed the door and went downstairs to the utility room and placed the items in the washing basket ready for Mark to wash.
I checked for his Jeans and Trainers so hid them in the washing machine for now, I will spring this on Mark later to say that we forgot to wash them and this be good time to get him in the bath and then I can get his t shirt and boxers off as well and get them all washed together ready for the morning.
Now to go see how he is getting on.
“Hi Mark how is it going, nearly done I hope” I asked.
“almost finished hopefully everything is okay for you”
“let me have a look see”
I checked over the ironing and was impressed he had done a really good job.
“this is really well done, I am impressed, your Mother taught you well I see”.
“I am going back to my office to carry on with my work, if you could give me a knock once you are finished, you have done a wonderful job today, really pleased with you”.
I went back to my office and carried on watching Mark iron, so happy he has done a good job as I can’t stand ironing and to not have to do this again soon would be a god send, although I am looking forward to giving him a punishment for any wrong doing even if I have to just be really picky when it comes to the ironing. When I was younger Thomas or my Father would do all my ironing and I did enjoy when Thomas would make mistakes and I was allowed to spank him for it. Fiona was quite horrible though if she found even the slightish mistake she would make him pull them off the hangers and crease them all up again, making sure they all needed doing again. I hopefully won’t need to resort to this though.
Mark eventually came to my office door and knocked to say he has finished the ironing. I went with him to check everything and said how happy I was with everything
“this is a super job Mark, I am so pleased, Now I have one final task for you to complete but I not sure how you going to be with it as you need to be extremely delicate OK, understood”
“OK no problem what you needing”
“I would like for to wash some of my lingerie for me, my bra and panties sets, some stockings, but this will need to be hand washed would you be comfortable washing my things by hand this way. Do you mind”
“i don’t mind if you don’t mind”
“OK I have put everything in the basket in the utility room, please be careful with them”
“I will no problem”
“thanks again Mark”
I went back to the kitchen and made another cuppa then went back to my office to check the camera on watching Mark washing my lingerie, soon he will be washing his own panties like this as well as mine but I was curious as how he would react to being asked to do this, of which he didn’t seem that put off so I am guessing that is Mother has had him do this at home already but I doubt hers would be as pretty as mine. Ha-ha.
I wonder how she is going to feel when she knows what has become of her only son, hopefully she will approve then perhaps she would like to baby sit one night and then at the wedding she could lead him down the isle in all his wedding finery, I think I will wear a nice trouser suit myself but I am getting a head of myself, plenty steps to take before have to worry about introducing Mark as a sissy to his own Mother.
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pollyannauk,
I'm really enjoying your first story.
You are making me wet my diaper in anticipation of what lies ahead for Mark.
I do wear boy clothes when I go out, but I love wearing dresses in the house.
I'm going to change into a fresh diaper, lingerie, housedress, and apron to do the dishes and start preparing dinner.
I'm looking forward to future chapters.
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Lovely story and thank you for the great update. I am so looking forward to see what is in store for Mark, I love the art of gentle feminization by strong smart dominant women and this story is one of the best I have read in a while. Thank you, Love Marci
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Thanks for your kind comments again,
My What’s App pinged to say my Mother was pulling in the drive. I went and met her at the door, made her a cuppa then we went into the office where I showed her the camera with Mark washing my lingerie, Mother was really pleased and then showed me the nightwear she had brought over for Mark to wear. She put the panties on her lap then held up the baby doll for me to see.
“so what do you think” my mother asked.
“Oh that is very cute Mother, Mark is going to look great wearing that”
“I have the socks and I also decided to bring the little training bra as well, have a look at this”
My mother took out the socks and put them on her lap to show me them, they were white with a trim of hot pink and tassels around the top. She then showed me the training bra, which had little straps and a bow on each side of the cups and one in the middle”.
“Oh Mother I love that but I’m not sure I will be able to get Mark to wear that tonight it might be bit of an awkward conversation”
“ You see I was thinking about that earlier, why don’t you get him into the bedroom and when you showing him the nightwear can say to him I have this cute little bra or you can wear this lovely baby-doll and after some playfulness on your behalf saying he has to wear one he is bound to pick the bra over the baby-doll. Then once you have him in the bra, all you need to do is make up some reason for why you would like to see him in the baby-doll as well, then once he is dressed in it, just play on how cute he looks and that you would love for him to keep it on”
“Oh Mother you are very clever”
“Well I have had plenty of years of experience of dealing with sissies over the years and am looking forward to having another potential newbie to play with in the next few weeks too, I do hope things work out for you tonight I really do, I just love breaking in a new sissy” my mother laughed.
“I hope so to Mother, Mark does seem perfect for the role, he hasn’t put up much of a fight yet”
“Oh I almost forgot, I also brought over this cute little hair bow to go with the outfit” My Mother said while reaching into her bag. “Now I don’t expect you to get him to wear this straight away wait till you settled down had a few glasses of wine together then see if he will allow you to put it in his hair”
“Oh that is so cute mother, I love it, I hope Mark does too”
“And I also bought over this satin night cap for him to wear in bed, see if you can get him to wear this later as well, okay, Now I really must be going and surely it nearly time for Mark’s bath, tell me are you going to bath him or let him do it himself this time, because it would be great if you could bath him, in time he is going to be bathed by various people and as part of his training he is going to need to be bathed by other sissies as well, so it will give me an understanding of how submissive he is already is, I’m really looking forward to bathing Mark myself in a few weeks, if everything works out for you and if not I’m sure Aunt Glenda will have a suitable replacement lined up for you, but lets hope it doesn’t come to that okay”
“Mother please, I am trying, I like Mark a lot I just don’t want to push to far so early but I will try, I promise”
“Okay darling no worries, anyway I really must be going but it has been great to see you and please let me know how things go okay”.
I let my mother out then took all the nightwear upstairs and placed it all in the top drawer of the spare room, apart form the hair bow which I hid in my bedroom drawer. I then checked the en-suite bathroom made sure everything was ready for Mark’s bath, I took out a disposal plastic apron that I wear when I give Frank his bath and placed it on the shelf ready then checked I had all the soap and shampoo ready, it was Johnson and Johnson so wouldn’t matter if the soap got in Mark’s eyes perfect for a little sissy. Now everything is ready time to see if Mark will let him me bath him, perhaps a little wine might help him relax a little bit.
I went downstairs and to the utility room and then walked in and asked Mark how he was getting on, he had almost finished and I could see he just one pair of my panties left to do.
“This is really great work Mark, I’m very pleased with you, once you have finished come and see me in the kitchen okay I will go open a bottle of wine for us both”
“Er I have never drunk wine before Miss”
“That is no bother Mark it will be a nice change for you then, come see me when you finished”
“Yes Miss”
Back in the kitchen I got a nice bottle of wine out and two glasses, ready for when Mark returned. I hope this relaxes him enough to bath him, I need to go gentle tonight but hopefully soon he will be on the path of no return, I just need to get him moved in and then I can start putting the steps in place to get him where I need him ready for meeting my mother. I was sat there having a think about Mark is going to look in his nightwear tonight just as he walked in the kitchen.
“Hi Mark, come sit down you have done a wonderful job lets have nice relaxing glass of wine with me then we can pick something to eat from the pizza place”
“I’m not sure Miss I have never really drunk alcohol before”
“That’s OK your an adult today” He won’t be an adult all the time he is living here but he can worry about that later, for now I need to get him relaxed, I want to bath and dress him in that lovely nightwear.
I got up and gave him a hug as I though this would be a great way to check his apron bow, which was looking very pretty.
“why don’t you take a seat and relax, you have done a fantastic job today and you can now sit and have some relaxation time”
“Does that mean I can take off his apron and put back on my jeans”
“Oh god, I totally forgot, shit, shit, shit so sorry” Wait here a minute will you.
I run off pretending to look worried then got to the utility room I quickly grabbed his jeans in the washing machine and dumped them in the sink which thankfully Mark had left the water in the bowl, next time I would expect him to of cleaned everything away but luckily he had left it. I made sure his jeans were soaked then quickly grabbed his trainers and did the same thing. Once they were completely soaked I dumped them in the washing basket now just need to make this believable I thought.
I walked back to the kitchen and looking all apologetic, I walked up to the table and showed Mark his wet Jeans and trainers.
“I am so so sorry Mark, really I am, I put them into soak earlier in the bathroom and totally forgot about them as was in the office working” I lied to him but hopefully said it like it was believable.
“Oh no they are soaked, they will take forever to dry out, I can’t go home wearing them, what can I do”
“I’m really am so sorry Mark, but I tell you what I have a spare room, you can stay here the night if you like, you can have a nice relaxing bath, seeing as you have been on your feel most of the day, then we can order a pizza, watch something on Netflix and chill and I will make sure your clothes and trainers are ready for the morning, how does that sound”.
“Well as long as you don’t mind me staying over, that would be very nice of you, but what will I wear”
“Don’t worry about that I will look for something while you are in the bath okay, I’m sure I have something here you can wear”.
“Well okay but only if you sure”
“Of course I am sure, you have been very helpful today and done so much for me, It been a great help least I can do is let you stay over. Now lets have a glass of wine together and start relaxing after such a busy day for both us, you can even take off the apron if you want okay, If you could just pop these back in the utility room and I will open the wine for us.
“okay, shall I put them in the wash?”
“No it okay I will sort that later, just put them on the side for now”
It worked now time to get some wine down him before moving onto the next phase.
While Mark was in the utility room I opened the bottle of wine and found the pizza menus and left them on the table, I poured myself a glass and then poured out a nice big glass for Mark.
When Mark came back I asked him to come over to me and said I would untie his bow for him, Once the apron was removed Mark was left in just his boxers and t shirt. He looked a little concerned about this but I said “don’t worry it fine, you be getting out of them soon for your bath anyway.
“could I not just have a shower”
“Well you could but you have been working all day and nothing is better to relax that having a nice bath with soothing bubbles, trust me you will feel loads better afterwards, now come take a seat, tell me what you think of the wine”
Mark took a sip and looked a little perplexed and then asked if he could just have some juice instead”.
“how old are you Mark”
“I’m 21 but I thought you knew that already”
“I do, I thought you was an adult as well”
“I am adult”
“so would an adult have juice when in the company of a lady”
“Well maybe, perhaps if they were driving”
“But your not driving tonight are you”
“No I’m not”
“So then you can have a little wine, I like you Mark, really I do, perhaps in time I can see us going further but I need a man that can handle having a little wine with his meal or when relaxing with me is that understood or is that going to be a problem for you”
“No I don’t think so”
“good then have some of your wine please, take it slowly you don’t need to down it but as we are talking I would like for you to sip on your wine OK, can you do that for me”
“Yes OK”
I watched Mark take a sip of his wine and told him that was good. It’s wasn’t a lie as I do like to have company while drinking wine, If things worked out and Mark becomes my sissy husband will be plenty of times for him to have his precious juice, more than likely from a sippy cup too but will be times that I would like to relax with him while drinking alcohol, plus he will be more docile this way and a lot more willing, I hope.
“Tell me Mark have you had many girlfriends at all”
Mark took another sip of his wine then said “No not really, was one girl for a few weeks, I liked her a lot but she said, well it a bit em brassing”
“do go on, don’t worry I won’t judge you”
“Well she said I was too much of a wimp for her she wanted someone more confident and took take control in the relationship”
“And how did that make you feel, be honest it totally okay”
Mark took another sip of his wine and then said “I was hurt as I did like her but then realised it wasn’t meant to be, my mother said to me, not to worry and that I will find someone soon enough”
“Your mother is correct and tell me, hypothetically, would you prefer a relationship where you are in charge or would you prefer it if your Wife was more in control and would be the lead in the relationship”
“I’m not sure possibly”
“OK and how well do you get on with you Mother, do you have a good relationship with her?”
Mark took another sip and then said “Yes I get on really well with her, its just been me and her for a while now since my Dad left us”
“And how about when you were younger did you enjoy when your mother was motherly with you, did you miss that as you grew up”
“A little, I still enjoy the company of my Mother”
“That is good is good when a child has a good relationship with their mother. So hypothetically if you had a relationship with someone how would you feel if your Wife was motherly towards you”
“I’m not sure how you mean”
“do you like me Mark, I mean do you like being with me has today been nice, even though we not spent much time together and you have mostly done chores, have you liked being here, be honest and don’t forget to keep drinking your wine”
Mark took another sip and then said “Well I didn’t know what to expect today but it has been nice and I do like you Miss er Sophie can I call you Sophie now”
Mark took another sip and as I was watching him I thought it now or never, time to see if I can get this boy into his first sissy outfit but first lets see if he will let me bath him.
Right I’m going to get your bath started, I will call you from upstairs when I am ready okay, while I am away have a read through the pizza menu let me know what you fancy, okay”
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Such a sweet story, I love the way she proudly shows Mark off to her mother as they make plans for his further feminization, and the way Mark calls her miss is so sweet. Thank you for this chapter and I so look forward to Marks further service. Love Marci
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Right I’m going to get your bath started, I will call you from upstairs when I am ready okay, while I am away have a read through the pizza menu let me know what you fancy, okay”
I went upstairs and started to fill the bath for Mark, I made sure that the water was not to hot and had plenty of bubbles, the bath smelt of perfume so once he was bathed Mark would too, which is going to be interesting, I wonder if he will mind. I put on the apron on over my head and tied it at the back, I drunk the last of my wine, then went to the stairs and called for Mark.
“Mark honey I am ready for you now, the bath is waiting”
Mark came to the bottom of the stairs and I said to him “come on up sweetie”
As Mark was climbing the stairs I could see the wine has had the desired effect on him, he was walking slightly uneasy on his feet, “Oh deer Mark looks like you may have had a bit too much wine, it has gone straight to your head hasn’t it, come here it okay Mummy will take care of you”
“Mummy”
“Yes sweetie”
“No I mean you want me to call you Mummy”
“Tonight I do yes for now, you remember when we were talking I said hypothetically if you would like your Wife to mother you but didn’t know what I meant, well I am going to show you, come on it will be fun”.
I took Mark by the hand and led him into the spare bedroom, “here sit on the bed while I take off your shoes and socks, I tapped the bed with my hand and said “come on don’t be shy, Mummy is going to take good care of you okay then once you bathed we can have some yummy pizza, did you pick something you liked?”
Mark sat down on the bed as I took off his shoes and socks, “I like Hawaiian pizza please”
“Please Mummy sweetie pie remember, say it again”
Mark looked at me strangely but shyly spoke “Hawaiian pizza please Mummy, but I’m not sure I am hungry right now”
“awww did you over do it on the wine, oppsie, never mind lets have a nice bath then will see if you hungry afterwards we can always get pizza a little later if you prefer, OK raise your arms now sweetie and we can get your t shirt off as well”
I removed his t shirt taking note that he not have much chest hair at all, this is going to be easy to work with I thought.
“OK now lets stand up and then we can take off your boxers”
Mark stood up slowly looking quite uneasy on his feet, maybe I over did it on the wine, but hopefully this will work out well and he will offer up little resistance, I have only 3 weeks preparation to work with and I need him to be ready and willing to act properly like a sissy in front of my mother and allow himself to bathed and dressed by her and not just that I need to introduce him to wearing nappies as well, I hope I haven’t given myself to big a task to work with.
As I went to take down Marks boxers he stopped me and said “I don’t want a bath, I’m tired and just want to sleep, can I have a shower instead or maybe just skip washing all together and just sleep for a bit, that wine has made me feel a bit unwell”
Oh shit this is not good, but I can’t give in now, my trust fund is riding on this and Mark seems perfect for this role, I don’t want some boy given to me who is already trained and going to do everything I want, where is the fun in that. No I am looking forward to seeing his face when I introduce a new rule or outfit to him, I think with the right training he could look really cute and I think it going to be a lot of fun as well having him around, plus I won’t need to do any more chores in the house and If I don’t want him about for a bit, I’m sure my Mother or Sister would like to have him for a while and put him through his paces and if they are busy I’m sure would be other family members or friends of the family that would just love to have a new sissy to train. If he accepts I will need to visit my Sister and see David and Frank. it’s been a while since I have had the privilege of tormenting poor David. I wonder what Fiona will dress them both in, Mother said Fiona likes to keep David dressed as frilly as possible nowadays I wonder what he wears on a daily basis, No this has to work out I have come so far in such a short little time. I would love to be more stern with Mark tonight but that is going to have to wait until his fate has been sealed for now I have to be sweet kind and gentle I can not risk losing him.
“Aww I am sorry to hear that honey bun, the bath should relax you nicely then if you want afterwards you can get into bed for a little nap time and can some yummy pizza later, what do you say hey come on, Mummy promises to be nice and gentle with you, anyway you have working hard all day I thought a nice bath would help you relax plus you must be quite hot and sweaty, come on sweetie its my way of saying thank you for all your hard work today”
I moved his hand away and went to tug down his boxes but he stopped me again.
“What is wrong darling”
“I’m worried you are going to be disappointed”
“How so sweetie and don’t forget to call me Mummy tonight”
“Well I’m not that big you know and my last girlfriend thought it was so small and she said it was one of the reason she broke it off with me, and well I have really enjoyed being here with you, I am going to admit it has been different but I have enjoyed the time with you and don’t want to ruin it now and then I won’t see you again”
As Mark was pouring out his soul to me, I could hear in his voice that he was getting rather upset, I couldn’t tell if it was the submissiveness in him or the wine that gone so badly to his head but thought I need to use this to my advantage and make sure I keep him at ease.
To be perfectly honest though I really couldn’t less how big his sissy stick is, the smaller the better, he is never going to be putting it in me anyway, only place that will be going is in a cage or perhaps another sissy other than panties and nappies of course. He had me wondering how small it was now so time to get these boxes off and see.
“Mark do you trust me, have I been nice to you all day”
“yes but I don’t want to ruin it”
“then if you promise to call me Mummy from now on till I say you can stop, and do everything I say then I can promise you I won’t comment on the size of your little man or be disappointed, no pun intended there sorry” I giggled as I gave him a hug and a kiss on the top of his forehead. “So do you trust me and promise to be good for me and will have no more of this nonsense”
“Yes Mummy”
I so wanted to say good girl but thought this best wait till later for now I just told him “Good boy”.
“OK so lets get these boxes down and then you can soak in the bath for a bit, hopefully it will help you relax OK sweetie pie”
“Yes Mummy”
I took a hold of the waist of his boxers and expected his sissy stick to start popping out over the top but nothing happened, as I took them down further I got to see the little thing for myself, oh this is just too precious I thought it was tiny, no bigger than my thumb, maybe it wasn’t even as big as my thumb. I can’t go to measure it now though, it would upset him but it will need to be measured at some point for his cage, if I can find one that will fit that is. Oh yes this little thing is destined to be kept locked away.
“OK now step out of them for me, that’s good, and now we go get you all clean, now would you like to go potty before you get in the bath, I know you drunk quite a bit so maybe you need a little tinkle, How about you just try for me, OK come with me”. I reached out and took his hand and led him over to the toilet. “Now unfortunately I haven’t got a pedestal mat at this toilet so you will need to sit down to make sure we have no wee wee land on the floor OK” I just wanted to see if he would willingly sit down to pee, as once he has moved in this will be a rule that will be enforced shortly after. He sat down and looked at me nervously. “its OK Mummy wants you to go for a little tinkle as we don’t want you going in the bath by accident do we, just wait it will come”
As I watched him sat there naked on the toilet, I couldn’t help but start to think about that tiny sissy stick of his. His previous girlfriend was correct it will be disappointing for any woman but this couldn’t be any more perfect for me, I wondered if I could get the details from Mark regarding his ex and see I could get her to come round to see him when he is having one of his baby days, she could even possibly be another babysitter for him, it would be good to have a babysitter his own age or even younger perhaps. yes I hope she is younger, I must plan to get them details I think she would agree he is exactly where he belongs. Just then I heard the sound of pee hitting the toilet bowl which took me away from my trance of thought as I looked at Mark. “clever you” I so wanted to say girl again but thought no this will all come in due course no need to rush and spoilt it.
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“all done, okay lets get you in this nice bath, come on, the water is lovely”.
I took Mark by the hand and helped him into the bath. “is the water okay sweetie not too hot or cold”
“No it’s fine” he said shyly.
“remember our promise sweetie, you don’t want Mummy to get annoyed do you. So I ask you again, how is the water sweetie, not to hot or cold I hope”.
“No Mummy, it’s fine”.
“Okay well you be good and have a little soak, while Mummy is going to look for something for to wear this evening, play nice, Mummy will be back soon and will help bath you okay”
“Yes Mummy”
I left Mark in the tub and pretended to go find him something to wear, unbeknown to Mark I had already found something of course. Something extremely sissy for his first outfit, this isn’t what I originally planned for Mark, I planned to break him in gently to his new life but like my Mother said if I can get him to wear this outfit, I shouldn’t have many problems in the future. Up until a few weeks ago I hadn’t really been bothered about finding a guy to become my sissy and husband, okay I often thought about the money from my trust fund but I hadn’t really cared too much for the sissifcation of males other than my family that is. In the pass the men I had dated or had flings with have always been strong and dominant men even in my teenage years, not the sort that were suitable candidates for sissyfication, but now for some reason things seem different and I can’t wait to start training Mark to be my sissy husband. The thought of seeing the poor thing humiliated and dressed up for my own enjoyment and seeing him interact with other people including other sissies was starting to turn me on quite a bit, I had another look over the outfit that Mark was going to be dressed in and decided yes I am going to seal his fate tonight with a view of him moving in early next week, I am not going to let this opportunity pass me by.
I went back to the bathroom and found Mark relaxing almost a sleep in the bath, he has a long day after all, also he had his first real taste of wine so he was quite docile, I decided to not say anything and started to soap his hair, he stirred a bit but said “its okay mummy is here darling, you just relax and let me wash your hair” his hair was quite short on top and a light brown colour, I think I am going to let it grow out a bit so he can have a nice curly hair and perhaps will arrange to have it dyed a nice blond colour, yes I think it will better suited blond, until it ready for perming. I think I will have him wear some wigs in different style this way it will help me make up my mind to be sure.
“Now would you mind standing up for me please sweetheart, careful though I don’t want you to slip” Mark stood up and I directed him to face the wall, I used the sponge to rub down his shoulders then his back and then made sure to massage in lots of soap into his bottom.
“Okay turn around for me slowly darling” this was the bit I was looking forward to I wanted to get a proper good look at that little sissy stick of his, however Mark has already moved his hands to cover it though.
“arms by your sides please darling, don’t be shy remember what we said” Mark moved his arms to his side and I made sure to keep him like that while I took my time lathering up more soap on the sponge. “Now be still for me please, Mummy needs to wash it”.
I washed around his little sissy stick, seeing how tiny it was. I so wanted to laugh would be no tent pole popping out his panties that is for sure, it going to look nice and smooth just like a real girls. I held it at the end by my two fingers while stroking it up and down with the sponge. This started to excite Mark so I decided to use this opportunity to tell him about his outfit tonight.
“Mark honey Mummy is going to get you out the bath soon and dressed for the evening, now please understand the only clothes I could find for you were my nieces for when she stays over, she is a little bit younger than you but they should fit you OK” as I was saying this I was slowly rubbing up and down on his little member.
“I thought seeing as you have been my maid all day it shouldn’t matter to much if you dress again as a young lady tonight, so will you be a good girl for Mummy this evening and wear what I have for you without any complaints” As I was saying this I was constantly rubbing up and down on his member, which was starting to grow, although not so much in length but more in thickness.
“Mark honey please answer me”
“Yes Mummy” he said while getting quite excited in his breathing.
“Yes what darling” I said while speeding up.
“Yes mummy I will wear what you want this evening”
“And you will be a good girl for Mummy and wear everything without complaining”
“Yes Mummy”
“I want to hear you say please sweetie” I could tell Mark was almost on the edge.
“Yes Mummy I will be your good girl tonight and will wear everything without complaining”
I could tell Mark was almost ready to pop.
“so will you be extra good little girl and wear a cute little training bra for Mummy along with your nightie”
“Mummy I not sure I want to wear a bra”
“oh but you said you would wear everything without complaint” as I said this I stopped rubbing him.
“Mummy”
“Say it please sweetie for Mummy” I started to stroke him again slowly this time
“I will wear a bra for you Mummy”
“not just a bra honey a cute little training bra, say I would love to wear a cute little training bra for you tonight mummy with my cute baby doll nightie”
“Mummy er I”
“Say it please darling or Mummy is going to have to stop completely you don’t want that do you”
“No mummy”
“then be a good little girl and say it for Mummy”
Mark went to speak but nothing came out so I stopped playing with him and looked straight into his eyes. “say it honey, last chance”
Mark looked back at me shying then finally broke and said “I would love to wear a cute little training bra for you tonight mummy with my cute baby doll nightie”.
“That's wonderful darling I can’t wait to see you all dressed up, your going to look wonderful, now lets get all this soap off then we can start getting you ready, have you got any more hungry sweetheart”.
I could tell Mark was looking a bit perplexed as I completely stopped playing with him and starting get the shower taps ready, I did plan on letting him c-um in the bath but I thought this can wait till he is fully dressed I want to have a bit more fun with him yet before I let him finish off.
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Oh I think this little naive sissy is about to walk straight into mummy's trap. A life of nappies and frilly knickers seem to await him.
I bet his ex girlfriend will love babysitting him and changing his nappies. Please write more soon.
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Another lovely chapter in the sissification of Mark, I love how supple Mark is and how forceful the women in his life are. Thank you again. Love Marci
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“Okay sweetie, can you kneel down in the bath for me please, and don’t worry if you continue to be a good girl we can play with your thing a little more later, promise”
Mark kneeled down and I showered off all the soap. “Okay now can you pull the plug out for me and then stand up again”.
Mark pulled the plug out stood up and let me shower off all the soap, “okay all done, not only are you nice and clean but you smell all clean too” I’m not sure if Mark noticed but he had a lovely perfumed smell now from all the girlie bubble bath, he must of surely noticed but didn’t say anything.
“Okay step out and mummy will help you with you towel”. Mark stepped out the bath and I wrapped him in the fluffy pink towel.
“okay little one follow me and we shall get you all ready for the evening”
I led Mark back to the bedroom and then started to dry him all over.
“are you hungry yet”
“Not really mummy”
“Are you still feeling sleepy from the wine earlier”
“A little mummy”
“Not to worry darling, how about once you dressed you can have a little nap for a few hours, then Mummy will order pizza for you and you can have it later after nap time okay, how does that sound”
“Em I’m not sure Mummy”
“It wasn’t a request sweetheart I think a little nap will do you good, you have had quite a long day, now are you as excited as I am to get you dressed”
“Em I’m still not sure why I need to wear a bra Mummy”
“it’s not just a normal bra honey it’s a very sweet training bra, it’s more for comfort really and I bet it feels really nice on, trust me plus it will make Mummy very happy indeed if you wear it for me, you are going to wear it for me aren’t you honey, no backing out now please”
“I guess so Mummy”
“let’s hope so, now give me the towel and I want you to walk over to the drawers over there, open the top drawer and take everything out and bring it over to me and place it on the bed okay, off you go” As Mark walked to the drawers I took a seat on the bed, smoothing my skirt out and crossed my legs and sat waiting in anticipation for him to return carrying everything that my Mother brought over earlier today. I watched as Mark opened the drawer and looked inside and then paused just staring. “Come on Mark we haven’t got all day, Mummy want to dress up her little girl for the night, take everything out carefully and bring them over to me, chop chop”. I watched him while smiling thinking to myself, this is wonderful and not long now I will have him dressed in all this lovely sissy clothing and into bed for a nap and it’s not even 6pm, as soon as he is settled I must call my Mother and say how well things have gone, I think she will be really pleased. Mark came over carrying everything carefully and placed them on the bed next to me.
“Excellent, Okay lets get you dressed shall we, right first I think we will start with these lovely hot pink knickers, just look at all the little polka dots, oh yes these are so cute, don’t you think”. I said knickers as I prefer the term knickers for little girls but panties for adults, I just think it sounds better that way and I will be training Mark soon to make sure he knows the difference, knickers will be the term for his little girl outfits and for his more adult wear it will be panties.
“Right OK step into these then please sweetie”
I held out the knickers for Mark and held him as he stepped into them, then pulled them up around his waist. “Now you can’t tell me they don’t feel nice, have a feel all around, what do you think”
I watched Mark as he moved his hands around his knickers and then decided to have a feel myself, I felt around his bottom then around the front and went to feel for his sissy stick, I say stick it was more of a stump I could barely feel anything. “So shall we put your cute little training bra on now” I said while reaching for it on the bed. The training bra was hot pink it had 3 bows on it, one over each cup and one in the middle, with lace frills on the edging and nice little thin bra straps, there is no way he will feel like a man wearing this and soon he will never know what it is like to not wear a bra again as the only time he will be not wearing a bra is when he is in the bath or if I allow it the shower, other than that I want him to be in some form of bra at all times. I remember when Thomas was introduced on his 13th birthday to the wearing of a bra, Fiona and myself bought him some extra special girly ones as presents and Mother made him wear them for us, having him change them each hour through the day, she said it will be good practise as you not only having these ones your sisters are going to donate all there old ones to you too. Thomas looked at Mother as to say why is this happening to me but he knew to keep his mouth shut and just obey otherwise he would be in for spanking over her knee, birthday or no birthday. At end of the day he had a whole drawer full of training bras and from then he was made to wear them everyday, he would wear the plain ones for school and then change as soon as he got home into something more frilly along with a nice skirt or dress to do his homework. I don’t believe he has had a day since that day where he has not worn a bra, he is 25 now and happily married, I haven’t visited for a while but think I should plan to soon. “Okay hold your arms up for Mummy” Mark raised his arms for me to put on his little training bra, I made sure I took my time and lowered it down over his head and arranged the straps so they were in place over his shoulders. “Okay turn around for me please sweetheart, let me check the back” Mark turned and then went to lower his arms. “No darling leave you arms up for a moment please, let mummy check it first”. Mark placed his arms back in the air and I made sure the bra was settled nicely on his back, This bra didn’t have clips or any support and was made of satin with lace edging. It must of felt nice on him. Once I had settled the bra I reached around the front of the cups from the back and felt Mark nipples and then rubbed around in little circles. “Tell Mummy how it feels darling, here place your hands on the cups and rub around with your thumb and finger, does that feel nice, tell Mummy it feels nice” As Mark moved his hands to the bra cups I moved mine to the front of his knickers and starting rubbing his sissy stump. “tell Mummy how much you love your new training bra and knickers sweetheart, say Mummy I love my new training bra and knickers” I said while still rubbing up and down on the front of his knickers. I could tell Mark was starting to get excited again from all the rubbing as his breathing had intensified but other than that he was silent. “Don’t make me ask again little one”. As I said this I started to rub harder and noticed that Mark was also rubbing harder on his nipples, I still hadn’t heard anything from Mark other than his intense breathing so I stopped rubbing his sissy stump then all of a sudden Mark blurted out “ Mummy please don’t stop I love my new training bra and knickers”.
“That wonderful sweetheart, Mummy is so pleased” I started to rub his sissy stump again but slower this time I didn’t want him having a little accident in them. “tell Mummy it makes you feel so girly wearing a bra, say Mummy I feel so girly wearing my new training bra” I picked up a little speed and then heard Mark’s breathing get even more intense as he suddenly said “Mummy I feel so girly wearing my new training bra” And your knickers sweetheart don’t forget about them, say Mummy I love my new training bra and knickers, thank you for letting me wear them”. I could tell Mark was right on the edge but wanted to push him a little further making sure he didn’t c-um. “Say it for Mummy Sweetheart” Marks breathing was so intense he was starting to buckle at the knees as he said “Mummy I love my new training bra and knickers thank you for letting me wear them”. I was so happy I turned Mark around and gave him a kiss on the lips, then kissed him again but for a lot longer. “you have made Mummy so happy sweetheart, I am very pleased, but I would like to have a proper look at you in your underwear before you get your nightie on, I want you to walk over to the wardrobe turn and face me and then say again how much you love your new training bra and knickers and then say thank you for letting me wear them okay” I could tell as he looked at me he was sad that I stopped playing with him. “It okay sweetie if you continue to behave for me and do just I say, I promise before you have your nap, Mummy will help you c-um okay but you must continue to do as I say okay so off you go” As Mark walked off I sat down on the bed again and watched Mark walked over to the other side of the room and waited in anticipation if Mark would say what what I wanted if I wasn’t playing with him at the time. As I watched him I thought he had a cute butt in them knickers I going to enjoy spanking that in due course. Mark turned around and looked at me but stood in silence looking quite shy just how I wanted him, the perfect sissy standing in silence, scared and waiting unsure what to do next. “Okay say it for me then sweetie, don’t be shy its just you and Mummy here, nobody will know”. Although people will know if I want them too as I have 2 cameras in this room, 1 facing the bed and 1 facing the wardrobe and desk area nicely hidden so no one will known about them and they have been recording the whole time when ever motion is detected and I want to capture Mark in his underwear saying how much he loves his girly bra and knickers. “come on sweetie say it for Mummy, you do want to c-um before you go down for nap, I'm not going to wait all day for you|, on 3 okay or Mummy will not let you c-um tonight and we both know you don’t want that, so arms by your sides and with a nice big smile, I want you to say I love my new training bra and knickers, thank you so much for letting me wear them mummy” I paused and then said ”3, 2, 1” but before I got a chance to say go, Mark blurted out “Sophie I can’t do this, please its so embarrassing I agreed to wear this for you please don’t make me say it again”.
Oh my god I couldn’t believe it for the first time today this pathetic excuse of a man has finally decided to stand up to me and he also had the balls to call me Sophie, which is never going to be allowed, its either going to be Mummy, Mistress or Miss Cavendish but never Sophie maybe I will let him call me Sophie later tonight after his nap to put him at ease but once moved in, he will never ever be calling me Sophie. I am happy he has finally decided to fight back, this is a great step and means he not going to be such a push over and I can have a lot more fun with him but just not tonight, tonight I need him to have a great sexual experience and enjoy the moment of wearing such sissy clothing he hasn’t agreed to anything yet and he can still walk away, but I can’t lose him now, no this has to end today the way I planned and no other way. “Aww Mark honey don’t be silly, I think you look very pretty and I am the only one here, I love the way you look, I just want to make sure that you are happy with this too, I don’t want to play like this if you not enjoying this so that is why I want to hear you say it, you don’t want us to stop our little game do you, come on sweetie say the words for Mummy then we can get you fully dressed and we can let you c-um, you would like that wouldn’t you honey to c-um for Mummy darling, come on don’t be shy sweetie, say it for me”. Come on you pathetic little loser say the words so I can get you dressed and into bed and then I go down stairs and watch back the camera and relax with a glass of wine and order dinner, I’m starving. “or would you prefer we finish our little game for the night, which is it Mark, I am getting impatient, what it to be, I will count to 3 then I want to hear the words or we stop and you can go to bed without c-umming, 3, 2, 1 Go” and then just when I thought he wasn’t going to say anything the weak little sissy looked at me and finally broke and said quietly “I love my new training bra and knickers, thank you so much for letting me wear them mummy”. Wonderful but I thought lets humiliate the poor little darling a little more. “oh Mummy is pleased but can you say it louder for Mummy, I want to hear it nice and loud, ready 3, 2, 1, go”. This time he said it straight away and nice and loud, perfect this will sound great on the camera but I think I will get another clip with his nightie on and make it a bit more humiliating. “See that wasn’t so bad was it, I’m not sure what all the fuss was about, now shall we finish getting you dressed come sit on the bed and I will put on your socks”. I stood up and waited for Mark to sit down and then I put on his socks, they were white with lots of lace frills and a hot pink trim. “Right stand up and then put your arms in the air then we can get you in the this lovely nightie, I hope you like it it’s called a baby-doll and it made of shiny crepe satin and just look at the gorgeous ruffles on the bust line and all the delicious lace trim on the hemline, oh and look it also lined in chiffon I bet that is going to feel amazing against your skin, just you wait” I took the baby-doll nightie and carefully lowered it down over my Mark’s arms, then over his head and down his chest and made sure it was seated correctly. “There how does this feel sweetheart, does it feel nice”. “it feels nice but it’s a little heavy Mummy” That will be all the frills darling. Now lets just put on your night cap to protect the pillows from your wet hair and then you be ready for you nap but first you can do my a nice twirl”. I took the nightcap and placed it on Mark head making sure that it looked nice and puffy. “Right I want you to walk over to wardrobe again and this time I want you do a nice twirl for me slowy and when you have finished I want you to say “Oh Mummy I just love my baby-doll nightie it goes so well with my new knickers and training bra I wish I could wear it everyday then I want you to blow me 3 nice kisses, 1 to left, 1 to the right and then 1 to the centre, can you do that for me sweetheart and if do all that for me I promise I will help you c-um, now off you go, and remember your only going to get one shot at this so make sure you say it nice and loud” I gave Mark a little tap on his bottom and pushed him on his way. I watched him get to the wardrobe and turned around and waitied, come you stupid sissy I need evidence to provide to my Mother to give to Auntie Glenda that I am making progress before she decides to assign me some other already trained weakling so you better make this good and something that I can work with. Mark walked over and with only a slight hesitation turned around and said “Oh Mummy I just love my baby-doll nightie it goes so well with my new knickers and training bra I wish I could wear it everyday” he then continued with blowing 3 kisses exactly as I told him too”. “Oh Mark you have made me oh so happy, come here let me give you a big kiss” He did it he actually did it, this is perfect, he needs to work on his speech, it needs to sound more girly and with a lisp and perhaps I should of asked him to curtsy at the end but still plently of time to train him to do that. Mark walked over to me and I gave him a huge hug and big kiss on the lips then asked him to pull down the cover on the bed and go lie down carefully making sure to not to bunch up his baby-doll nightie while I went to the bathroom and got some tissues and some wipes. I came back from the bathroom and found him lying on his back waiting for me. I sat on the bed next to him and placed my hands in his knickers and started to play with him, I wondered how long it will be before he came. “Mark I have been so happy with you today I bet you are quite tired now aren’t you, just relax and Mummy is going to help you drift off to sleep okay” it wasn’t long before his little sissy stump starting getting hard, as it did I started talking to Mark again, “Oh I see you are liking this aren’t you, are you liking being dressed in a cute training bra and polka dots knickers with a baby-doll nightie I bet you feel like such a sissy girl wearing all that satin, tell me Mark are you feeling like a sissy”. As I was saying this I was starting to move faster with my hand and then thought now be a good time to take down his knickers. “Arch your back for me darling so I can take down your knickers”. Mark arched his back and I stopped to take down his knickers to just around his knees, His sissy stump was standing at full attention now and I knew it wasn’t going to be long before he wanted to explode. “Say I love being Mummy sissy girl, say it for me sweetie, or I will stop”. Mark was silent so I slowed down my stroking on him, which did the desired effect as Mark who was breathing heavly now suddently blurted out “I love being Mummy sissy girl”. To which I rewarded him by stroking him faster and faster. “Are you ready to c-um yet sissy girl, make sure you let me know when it going to spurt, I don’t want to make too much of a mess” “Mummy I’m ready to c-um, please let me c-um”. I got the tissues ready and cupped it around his little shaft ready to catch everything. “go on then sissy c-um for Mummy” Mark body jilted and then he almost screamed in ecstasy. “Well done, such a clearly girl, I bet you must be ready for your nap now” I wiped him with the wet wipe and then pulled up his knickers around his waist. “Sleep tight darling, Mummy is so proud of you” I said as I gave him a kiss on the forehead. “I don’t think you will need the cover but you can pull it up if you need to okay, I will order your pizza and will wake you in a few hours, sleep tight darling”. I gave him another kiss on the his forehead and went to bathroom to throw away the tissues and wipes. Such a waste, I really wanted to feed it to him and let him taste his sissy juice but thought that might be a step too far tonight, I also thought about taking his sissy stumb in my mouth and letting him unload and then giving him a big kiss afterwards but I didn’t think he has deserverd that reward just yet, all in good time I thought. As I left the bathroom I was going to remind him if he needed the toilet to make sure to sit down but he was already sound asleep. I looked at my watch it was only 6:40pm, I will leave him there till 9pm I think but keep an eye on him on the camera. I quietly left the room and closed the door making sure not to make too much sound and crept slowly downstairs and went to the utility room and put Mark’s clothes and trainers in the wash then went back up to the kitchen got myself a nice big glass of wine and went to my office to monitor Mark on the camera, he was sound asleep and looked so cute in all his sissy clothing. I took a screengrab of him sleeping and saved it to my desktop, I then watched all the footage of me bathing him and dressing him and saved a few mini clips of him in his underwear where he was refusing to say he loved his girly clothing and when he said he loved them and saved that then also took a clip of him when he was fully dressed where he was blowing kisses and saved that also. I thought I am going to need a bigger hard drive soon to cope with all this footage. I then opened up my What’s app on my computer and sent the still of Mark sleeping over to my Mother with the caption “isn’t he cute??”. I checked Mark was still sleeping and then called the pizza place and ordered dinner.
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Great chapter she seems to have her little sissy heading in the right direction. I wonder if when mummy wakes him up from his nap she might find his knickers damp from having a little accident whilst asleep. Sissy would be embarrassed on being discovered I think.
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Another great chapter! So nice for Mark having the opportunity to develop as a lovely sissy under loving guidance of his caring mistress. Thank you, love Marci
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Dinner ordered and as it was going to be take about 40-45 minutes to arrive, I watched some more clips of Mark and me on the bed, he came quite quickly so either he was really turned on or it was just the fact he never really had his sissy stick played with before either way he best make the most of it as soon I plan to have it nicely locked away.
My mother replied on What’s app with a smiley face saying so cute, can’t wait to play with him, so I sent over a few clips of him over by the wardrobe doing his little dances, replying hopefully tonight you can send the one of him smiling and blowing kisses over to Aunt Glenda as I plan to ask him to move in later on, I will let you know how to goes with a big smiley face.
Oh how very exciting my Mother replied.
The food arrived around 7:30pm so I had my pizza and then decided to wait awhile before I want to wake Mark so I checked he was still asleep and poured myself another glass of wine, I then got his clothes out the wash to dry them and went and had a bath myself. Afterwards I changed into some nice nightwear to keep Mark on the edge, I chose a lovely short black satin nightdress with black stockings and short satin wrap around also in black which I left open with a satin pair of black panties.
It was just coming up to 8:40pm and I could see on the camera Mark looked like he was waking up, I decided it was now or never, I have been wondering how to approach this but it make or break time. Lets go wake him and see.
I approached the bedroom door quietly and then slowly opened the door, Mark was laying almost as I left him the duvet cover was still at the bottom of the bed and I could see him laying in his lovely nightwear, looking like the sissy he should be. I walked over to him and gently sat on the bed next to him and stroked his head on top of his satin nightcap. “Mark Honey, it’s time to wake up, did you have a nice nap-time”
Mark slowly started to open his eyes and looked at me a bit confused. “Mark honey do you remember where you are, we had a little role-play with you as my little girl then you got tired and had a nap”.
“Oh god yeah, sorry what time is it”
“It’s coming up to around 9pm darling are you hungry, would you like to get up and have something to eat and drink?”
“Please that would be nice I am quite hungry now”
“OK come on up then”
As Mark got up out of bed he suddenly realised what we was wearing and looked around all shy and embarrassed.
“oh I totally forgot all about this outfit, can I get changed before eating” he said
“silly you, don’t you remember, I love seeing you dressed this way, it’’s just me and you and your clothes are still drying, don’t worry we don’t need to continue the role-play of you being my little girl for now you can call me Miss Cavendish Okay”
“Em OK”
“Em OK what”
“Sorry yes Miss, Miss Cavendish”
That’s better, now tell you what I will let you wake up have a little wash and then I will meet you downstairs in the kitchen when you ready does that sound good”
“Yes Thank you, er Miss Miss Cavendish”
“Less of the em please”.
“Sorry yes Miss, I mean yes Miss Cavendish”
“better, make sure you get it right, otherwise you can go back to calling me Mummy, Understood”
“Yes Miss, Miss Cavendish, thank you, I will have a wash and meet you in the kitchen”.
I left him alone to gather his thoughts then went to my bedroom and grabbed the hair bow and then went and waited for him in the kitchen.
Mark soon arrived at the kitchen door, still dressed as he was put down for his nap, however his baby-doll nightie had become quite twisted and his sock had fallen down a bit, also his knickers were all out of place, in future I will punishing him for arriving looking like this but today I will just make a mental note of it. “oh dear just look at you” I laughed, “come over here let me sort you out.”
Mark walked slowly over to me, I straighten out his baby-doll then asked him to turn around, while I smoothed out his knickers.
“Okay can you bend down and pull up your socks for me please” As Mark bent over I got a great look at his bottom.
“Perfect, that’s much better, now just one more thing then you can relax for a bit okay”. I spun Mark around and then removed his satin nightcap, he seemed quite pleased about this but his face soon changed as I showed him the hot pink hair bow. “Ah not to worry sweetheart you can have your nightcap back before you go to sleep later but for now I think you will look much better with a nice hair-bow, don’t you think”. Mark looked at me all sullen and said nothing, “I said don’t you think”.
“Yes Miss Cavendish”
“That's better” I attached the hair-bow in his hair just off to the side and gave him a nice hug. “Now you can relax and have your Pizza, feel free to make yourself a drink, I have juice in the fridge or cordial orange is in the cupboard, please be extra careful to not get your baby-doll nightie dirty. You can heat your pizza in the microwave or have it cold, totally up to you. Okay”
“Yes Miss Cavendish, Thank you.”
“Great okay once you are finished please come and meet me in the lounge I would like to have another chat with you.
“Yes Miss Cavendish, thank you”
“good girl, I laughed “now finish up and come see me”
I walked off into the lounge, put on some chilled music on a low volume and sat down on the sofa and waited comfortably for Mark to enter.
Mark arrived at the lounge door about 15 minutes later, “Come in” I said, “here come sit next to me but before you do how about you give me a nice twirl and perhaps you can give me a little curtsy to say thank you for your pizza, you do know how to curtsy don’t you”
“I think so”
“Off you go them”
Mark was in perfect view of the lounge camera and this would be another great opportunity for a clip to send over to my Mother to pass onto Aunt Glenda. He looked at me twirled and then bowed his head and performed a reasonably good curtsy.
“Very well done, was that your first attempt or have you done this before” I gave him a small laugh then said “I was quite impressed, don’t get me wrong it still needs work but for a first time I am very impressed, how about you curtsy to me, then leave the room and come in again in about 10 seconds and performed another curtsy, the time without the twirl and thank me again for dinner, can you do that?”
“Yes Miss Cavendish” Mark curtsied again and left the room, his walking could do with some work but still he seemed to be starting to relax a lot more when asked to do something. About 10 seconds later in he walked, he bowed his head, took hold of his short nightie and performed another curtsy and then thanked for his dinner and stood waiting quietly for me to speak. Another great moment for the camera.
“Well done really well done Mark, now come here sit with me on the sofa” As mark got closer I welcomed him to sit next to me and positioned him so he just off to the side facing me.
“Now Mark there is something we need to discuss, when we first met you explained that you had been made redundant and that you were also not able to afford your boardings so you are currently staying with a friend but that this can only be temporary and also that you might not been able to finish your college course, have I got the all right is that correct?”
“Yes Miss Cavendish that is correct”.
I was pleased he remembered to address me properly and brought his hand into my lap and looked him in the eyes. “Now Mark I have a way I could help resolve this problem but what I am about to tell you might put you off but just hear me out okay, can you do that for me sweetheart”
“Yes Miss Cavendish, of course”
“Good, okay now I come from a family where relationships are the Female Led type of relationship and one of the rules for this is the females in the family should be married by the time the female is the age of 30, If that happens the person will receive a nice trust fund on a monthly basis and this will be enough to live very comfortable. If the female in the family decides to not have a Female Led relationship or does not get to marry before she is 30 then the trust fund will not be released to them and the money will be returned to the trading accounts. Are you with me so far?”
“Yes I think so Miss Cavendish”
“Good now unfortunately there is a lot more rules to this, for instance the males in my family are not treated like males but are they are kept in a petticoated type of lifestyle, meaning the male of the relationship will be kept en femme. Now unfortunately this is not something that can just occur from time to time and needs to be from the minute the person decides to enter the relationship, till death to us part. Now before I let you ask some questions, let me explain a few things. Okay so far”
“Em Yes Miss Cavendish”
“Remember less of the em dear”
“Sorry yes Miss Cavendish”
“Right OK now firstly you can probably tell now why you are dressed the way you are and why also you wore a very feminine pinny earlier on today, the reason for this I have been testing you to see how you react, you see a real manly man Mark would of just of said no to the apron and definitely would not be dressed like you are now, just look at you, are you telling me this is what a real manly man would dress like, no and that is what I like about you, I love your soften side and what I am trying to say is how would you feel about moving in with me and becoming my future petticoated husband?” Mark went to speak but I put my finger to his lips and said “Hold on honey let me finish, If you decide that you would like to spend the rest of your life with me, then you can move in next week, of course you can still go to College and finish your course as I remember you saying you don’t have long left to go on this, but you need to understand that once you have agreed to move in, you will permanently kept dressed en femme, this would mean in my house, even when we have visitors and also when go visit other people, but bear in mind every male whether they be husband or son they will dressing the same as you, so you have nothing to fear, it might be different at the beginning but you will soon adapt to this life style, please also note you will not be dressed so you can pass as a real female, no you will be kept of the look more of a sissy, with outfits ranging of various ages and roles also please note that when you go out along I will permit you to wear male clothing but you must wear the underwear I chose for, meaning you will be expected to go to college with female underwear on, just say Yes or no Miss Cavendish if you understand as I haven’t quite finished”
“Yes Miss Cavendish”
“Good girl, now if you do decide to say yes, please note we shall be often tested that you performing as well as can be before the marriage can take place, this means you need to play the roles perfectly and really get into the character no matter how humiliating this might be, so depending on the outfit you are wearing, will depend how you need to act that day but don’t worry you will receive plenty of training but we go into more detail on that once you have have decided to except my offer, are you with me so far, please remember I still not have finished but I want to know you are listening and understanding all of what I am saying okay”
“Yes Miss Cavendish”
“Good, now I understand that this is a hell of lot to take in but you must admit this weekend has been a lot of fun and we shall be able to have a lot more fun together. If you do say yes, I will pay off any debts that you currently have but please note I will be closing any bank accounts you also have and you will rely on me for money for the foreseeable future, not that you will need much but we will come to some arrangement. You must understand that I am going to need to buy you lots of outfits which is going to cost a vast amount of money , your board and meals are going to be free. I only have less than a year to make this work, so If you do decide to say yes I need to make sure that you don’t change your mind before the wedding and run off so I am going to be quite strict with these next steps if you decide to move in and accept this role, So before we go any further, are you interested in becoming my sweet sissy husband to be, just think no more debts, no more worrying where you going to live and all you need to do is keep dressing up like you are now, you got to admit you had a lot fun before your nap-time earlier, you don’t want that to stop do you, you can speak now”
“I am not sure Miss Cavendish, I must admit I have had a lot of fun being here with you and I don’t want it to stop but I am not sure that I commit to this role you are asking of me, what If I don’t turn out like you expect me too?”
“Oh don’t be silly I don’t expect you to fulfil this role straight away, as I say you will require a full training plan for each role but that will come over time and we can take it slowly at first, before you are introduced to other people dressed similar to how you are now, but it will be a lot of fun, don’t you think. I would so love for you to say yes”
“If I did say yes what would need to happen, you said about next steps what are they?”
“Well yes, so I know you are actually serious and not going to run off on me, I will create a ledger of all the money you owe me for your previous debts, the room and board, food, your clothing and anything else I feel requires to be paid back for instance if I had to pay for anything towards you training this will then billed to you and I would expect payment within 1 month. If you fail to pay off that debt then that is where the next step comes in, now remember we only going to have this in place if you later decide to change your mind”
“What is the next step please Miss Cavendish”
“The next step is before you move in you will email a list of contacts, this will be your Mother, your ex Girlfriend, your best friend, your previous employer and your college Teachers, I would require there email addresses, telephone numbers and also the address, then if you run out on me and refuse to pay me back, any pictures or videos I have of you dressed up, will be sent over to them, but this is only a precaution as you running off on me like this will ruin my life as it will be too late to find a replacement so even though I wouldn’t want to do this I have to cover my own back, now I know this sounds harsh but I will stand to lose a lot of money so this is just a like having an insurance policy, but you wouldn’t want to run off on me, would you, come here stand in front of me”
I felt like I was losing him and I as have laid all my cards on the table now time to help get him to agree. Mark stood up and stood in front of me.
“Now tell me does this outfit feel nice, is it better than sleeping in boxers, I bet the baby doll felt lovely didn’t it and what about these knickers, are you sure you don’t want to wear these any more” As I was saying this I started rubbing the front of his knickers and could see he was starting to get hard already. “shall we take down your knickers and see how your little man feels about moving in and having the opportunity of a lifetime to be kept dressed as a pretty petticoated husband, are you getting exciting honey, tell me you want me to let you c-um don’t you, just like earlier, would you like to c-um again for me”
“Please Miss Cavendish, I would love that”
“Oh really so does that mean you are going to except my offer”
“I’m not sure Miss Cavendish”
“Well I am not sure if I want to let you c-um tonight then”
“Please Miss Cavendish, please let me c-um”
“Well Please Mark say yes to moving in with me, what do say” As I said this I was rubbing harder through his knickers and could tell it wouldn’t be long before he is finished.
“Mark honey, what do to say would you like to dress up like this all the time and play with you Mistress, Mummy”
“Please Miss Cavendish let me c-um, I promise to be good and think about you offer” he said while almost buckling at the knees. I stopped playing with him and thought now it time to get serious.
“OK I tell you what I will let you c-um then you are to curtsy and say thank you for allowing me to let you c-um, then you are to leave the room and go up stairs and sit on your bed and have a think, I will wait down here and you have 20 minutes from the time you leave the room to make your decision. If you decide yes, then you will come down with the list of contacts I asked for, I will accept just the email addresses and phone numbers for now, you will enter the lounge curtsy and say please Miss Cavendish can you train me to be your petticoated sissy husband and hand me the list, you will then pose for some pictures on my camera and this will seal the deal if you decide no, then you will remove the baby doll nightie and training bra and come down in just your knickers and socks and say sorry Miss Cavendish this is not for me and then you can go up to bed and sleep till morning and then leave quietly in the morning and we shall never speak again. Please note though if you say yes and then change your mind I will be sending the pictures we take over to all the list of contacts as you will have broken our agreement, understood, now would you still like to c-um”, I said while taking down his knickers.
“Yes please Miss Cavendish please let me c-um, please” he said pleadingly.
“Okay but remember what I said, you will find some paper and a pen on the desk in the room”
I took hold of little manhood and made sure I gave him such a good show, I started to kiss the end and put the tip in my mouth, I then started licking the end of his sissy stick and tickle him under his balls, this was enough for him and as I cupped the end he spurted straight into my hand.
“Okay pull up your knickers girl, I have kept my end of the bargain, you know what you need to do”
Mark pulled up his knickers and then looked at me with a big smile on his face and said “Thank you Miss Cavendish for letting me c-um and then did a curtsy and left the room”.
I waited for him to go upstairs and checked how much c-um he left this time, it was quite sticky, I so wish I could of fed it back to him, but I didn’t want to spoilt the moment just when I am so close to getting him to move in, all of this will come in due course, I went and washed my hands in the sink and sat and waited for him in the lounge, I could of just checked the cameras but decided to leave it as a surprise.
About 15 minutes later I heard Mark coming down the stairs, as he reached the door I could see he was still dressed in his full nightwear he entered the lounge and dropped a really good curtsy maybe he practised this upstairs in the mirror, I will check the camera later and see, he then said, “please Miss Cavendish can you train me to be your petticoated sissy husband” he then curtsied again and handed me his phone will a the list of contacts on.
“Oh Mark you have made me so happy, please stand properly so I can take a picture of you in all your glorious nightwear” Mark stood I took some pictures of him and then made a note of all the contacts I gave him a huge hug and said now I think it time you were back in bed please, go to the kitchen and fetch your nightcap and come back and ask for me to help you put it on and don’t forget to curtsy” I helped Mark with his nightcap and sent him off to bed telling him it was way pass his bed time and that I will wake him in the morning. I then went and edited the clip of Mark asking to be trained and sent this on to Mother, will the caption he said yes. I then decided it was time for me to sleep it was only 11pm but I had one hell of a day, phase one is finally complete, phase 2 is going to be very interesting.
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I loved it please don't keep us waiting to long for phase two.
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Another great chapter, I so look forward to each instalment anl learning what is in store for Mark. Thank you, Love Marci
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Very sorry to anyone that has been waiting for the next part has taken so long, Life has been quite hectic lately, hopefully the next part won't take me so long.
Phase 2: Start
Mark left around 10am the next morning, I made sure before he left that he remembered exactly what he promised and said that I expect to him to arrive on Tuesday at 9am and to not be late, or be a no show or I will sending on the pictures I have. Marked promised he will be back and then I gave him a kiss goodbye and a little spank on his bottom as I walked him to the door.
Once Mark had left I called my Sister,, we had a long catch up and I explained about Mark and she said she was only too willing to help me out with some starter clothes and said it would be good for me to go over and visit on the Monday late afternoon that way Frank would be home from School. It has been quite a few years since I had visited Fiona but I was looking forward to seeing David and Frank, I wondered how they both would have been dressed. Fiona explained that she will sort out all of David clothes that she didn’t feel were suited for him any more, and as they are not going to be needed for Frank in the future she would be only too willing to donate them on the condition that she can take an active role in Mark’s training. I said that won’t be an issue but wondered how comes she didn’t need them for Frank, I guess I can ask her on Monday.
Week 4 – 48 weeks to go till I am to be married
As planned I went over to My Sister’s house at 4pm, My sister lives in a lovely house, much nicely than mine, It not very big, only has 3 bedroom the same as mine, but it located in a nice area of Chigwall, Essex and has it own gated area with a long gravel driveway, with grass either side. I drove up to the gate and pressed the intercom, “Hello how may I help you” said a young girls voice.
“Hi its Aunt Sophie”
“You are expected, please drive up to house and come to the front door, thank you” came the girls voice again, sounding very young, feminine and polite.
Once the gate opened I drove up the driveway and parked the car, then walked to the front door, as I got closer to the door it was opened by a lovely looking maid, dressed in what looked like a satin maids uniform with the skirt held out by petticoats not to wide but just enough so they bounced a little, the maid was wearing high heels about 5 inches and stockings, They were also wearing a full pinafore apron with frills on the top of the shoulders and on top of her head was a maids head dress with ribbons and streams that went down to the top of her back in white satin. I realised then this was Frank, he has a little page boy wig on but I could tell under the light make-up it was him. “Hello Auntie, Mother is waiting for you in the lounge, please follow me” Frank then curtsied and waited for me to follow him, he was looking amazing, I thought as I watched his petticoats and skirts bouncing nicely as he walked, which was perfect, he walked with such grace and femininity. We reached the door of the lounge and Frank knocked quietly on the door, I heard Fiona say Enter and Frank opened the door, entered and curtsied to her, “Mother, Auntie Sophie is here for you” and then he curtsied again. He then turned around and dropped another curtsey to me.
“May I take you coat Auntie”.
“Why thank you, yes you may” I undid my coat and handed it to him, he then dropped another curtsy and said “Thank you Auntie” Frank then curtsied again to Fiona as he left the room and shut the door behind him.
I gave Fiona a hug and kiss and then took a seat on the sofa.
“Well that was very formal but you didn’t need to worry about that for just me visiting, it was lovely though, he was perfect, I can see you have trained him well”
“He is coming along very nicely indeed it going to be a shame for when he leaves me”
“Leaves how do you mean”
“I will explain in a minute, would you like a drink at all?”
“I would love a cup of tea”
“No problem”
Fiona then picked up a bell, kinda like an old school bell but a lot smaller, and gave it a gentle shake, just afterwards there was a knock at the door and Fiona said for them to enter. A few seconds later Frank entered the room, he curtsied to Fiona and then myself.
“we would like some tea please”
“Yes Mother”
Frank then curtsied to us both again and left the room, closing the door.
“So tell me then how do you mean, leaves”
“Well Frank will be sixteen next month and is going to be moving out to live with his new owner, he doesn’t know who it is yet, he just knows that its’ someone from his school, I am having a party for his birthday and they will be coming to collect him at the end of day. speaking of which you will need to come along with Mark, Mother sent me the videos, he looks quite shy but such a cutie, I am looking forward to having him over my lap for a spanking, have you spanked him yet at all?”
“No I haven’t not yet, I wanted to but I didn’t want to rush things”
“Well a sissy must have regular spankings, even if they have been good as gold, it is good for the them so make sure you have a regular routine with Mark set up as soon as possible”
“I will do, well I plan too once have got him settled in with me”
“OK make sure you do this on the first night he is with you and explain you will be doing this every night, no matter how good a sissy he has been. Now the party is going in about 6 weeks, it would be great if you could both make it, of course if you do, Mark will need to have a lovely dress fit for a 6 year old, I can give you the details of a lovely dress maker who doesn’t live to far from here if you want, she has made lot of outfits for “David and Frank, including the maids outfit Frank is wearing today”.
That would be lovely, is it okay to take Mark along with me to see her”
“Of course you can, she is a friend of the family so not a problem, have you taken Mark anywhere sissified yet?”
“No not yet”
“Well once you feel he is ready, you will need to bring him over for a visit before the party of course, I can have fun being the strict Auntie” Fiona laughed and then I laughed too, just then the door was knocked on.
“Enter” said Fiona.
In walked Frank, he dropped a curtsy to both of us, expertly while holding the tea on the tray. He hadn’t just bought a tea in a mug but had a full tea set, with cups and sauces, As we carried on talking about Mark, Frank made the tea, making sure to not spill anything, he expertly made the tea, pouring from the teapot without spilling a drop he then curtsied to both of us and left the room and shut the door.
“he so well behaved” I said.
“he is but he is due his afternoon spanking before David comes home, would you like to do the honours today perhaps”
“Really, I would love that”
“Of course”
Fiona then rung the bell again and few seconds later the door was knocked on again.
“Enter please”
Again Frank came in and curtsied to both of us and waited demurely with his head bound for his next instructions.
“You have been very well behaved today Francine, I am very pleased, however you know the time is coming up to 5pm and what does that mean”
“Time for my daily spanking Mother” Frank, said and then curtsied.
“It it indeed but seeing as we have a guest, I think it only right that your Auntie Sophie gives your spanking today, understood”
“Yes Mother” Frank answered and dropped another curtsy.
“Sophie over to you, please deal with Francine how you feel fit, I am just going grab the bags I sorted out for you, Francine you will do exactly as your Auntie says, it that understood”
“Yes Mother” Francine then dropped another curtsy as Fiona then got up and left the room”
I looked over at the poor boy, looking just like Thomas did when it was time for his daily spanking, knowing that poor lad is going to be kept at the beck and call of his new Mistress soon and I thought I am going to enjoy this moment.
“Lift your skirt and petticoats for me Francine I want to see your panties”
Frank then curtsied, said yes Auntie and then lifted his petticoats and skirts and showed me his panties, they were white with lots of lace frills around them”
“such cute panties for a cute sissy, put your hands on your head please” Frank curtsied again and then placed his hands on his head.
“walk over to me and stand in front of please, no need to for you to curtsy”
Frank walked over to me and once he got near I lifted his skirts and then took hold of his panties, and started to take them down, I could see that his sissy stick was locked in a pink chastity device.
“Tell me Francine, how long have you been in chastity for now”
“since I was 14 Auntie”
“When was the last time you was released”
“Mother lets me be released once a month, but has said it will up to my new Mistress on how often I will be released in the future”
“Very much so, do you have any idea who it is”, I asked while stroking up and down his stocking legs as I settled his panties around his knees”
“No, all I know is it is someone from my school, that is all Mother has told me”
“now I want you come lay over my lap, nice and gently please, there’s a good girl”
Frank laid over my lap and I lifted up his skirt and petticoat and started to rub my hand over his bottom, which was so smooth.
“Such a sissy smooth bottom you have Francine, not very manly at all is it?” I laughed
“No Auntie”
I gave him some gentle spanks, nothing hard and continued to ask him questions, “you have been very well behaved today, and you look wonderful, now tell me the truth darling, do you enjoy being sissified?”
“When I was little boy Auntie it never bothered me, in fact I quite liked to get dressed up for Mummy but as I got older and wanted to play football outside with the other boys and Mummy would make me stay in doors and dress me up all pretty and have me play with my dolls or have me painting or colouring I got quite upset but Mummy would explain to me that is not the life for me and that I have been born into a family that treats boys differently and over time I would understand”
“Your Mummy is correct darling, and you got to admit you look lovely today and is it so bad to be a wear a skirt or a dress” I said while continuing to spank the poor boy, nothing hard just a nice soft spanking to warm up his bottom.
“Well I don’t mind wearing skirts or dresses so much they are just clothes and I have worn them for years now but I don’t enjoy having to wear a bra especially as Mummy makes me wear one all the time now, everywhere I go, even for when at school” As Frank said this I moved my hand away from his bottom and played with the bra strap on his back and traced the lines, giving it a little pull through his dress.
“But as you know darling all sissies wear bras’ it part of being a sissy, isn’t it, us Women have to wear them all the time, we don’t have a choice, so I think it’s only fair, don’t you, A sissy should never be without a bra if you ask me, day or night they should be wearing some sort of bra that is what my Mother used to always say” I said while continuing to spank him.
“That is what mummy always say to me too”
“And I’m sure your new Mistress will say the same thing too, whoever she is”
“I bet your wearing a lovely bra now, why don’t you stand up and lets remove your dress and you can show me”
“Yes Auntie”
Frank stood up and smoothed down his dress and petticoats and then I asked him to turn around so I could help him with the zip, I took his dress down to his waist and rested it on his petticoats, then traced my hands across his bra straps and gave it another pull again, I then turned him around so I could see it from the front, His bra was white with lots of lace and it had a little bow in the middle with padded breast inserts which I cupped with my hand. “Oh yes I was right, it’s very pretty, you are a very lucky sissy, is this the type of bra you wear all the time nowadays” I said while still feeling around the cups of his bra and giving them a little squeeze.
“Well mostly when I am home, I have similar ones for school or when going out but they don’t have the extra breast inserts like these, I also have some that have a lot more frills and bows for when mummy wants me to dress up as a little girl”
“I see, I would love to see you in one of them someday soon, perhaps you could dress as a little girl and come over and play together with my soon to be husband” as I was saying this I started to pull down his dress and petticoats and left him standing in just his bra, stockings and shoes.
“Auntie Is your husband going to be a sissy too like me, Daddy and Uncle Thomas”
“Yes Francine he is going to be just like you all, a cute prissy sissy” As I said this I traced my fingers on the inside of his stocking legs and up to his waist and around and back down.
“Do you mind if I ask if he knows what you have planned for him Auntie.”
“Well he knows that that I plan to sissify him as per our family traditions but he doesn’t know exactly what this involves overtime he will though soon enough” Just at that point the door opened and in walked Fiona who looked quite shocked to see Frank undressed.
“And what has gone on here, Francine you know you are not allowed to remove your dress without my permission What do you have to say for yourself young lady?”
Frank looked at Fiona with his head bowed down and spoke all apologetic, “I am sorry Mummy, but Auntie Sophie wanted me to remove it so she could take a closer look at my bra”
“That’s correct” I interjected, “It’s my fault I didn’t know I'm sorry”
“That only because Francine didn’t bother to tell you, which she should of done, I am not happy about this Francine and we shall deal with this later once your Aunt has gone home but for now I would like you to go upstairs and change into your school dress to complete your homework”
“Yes Mother” Franked dropped a curtsey as best as he could in his underwear then went to leave the room carrying his dress”
“Where do you think you are going young lady” Fiona snapped.
“Sorry Mummy you said to go and change into my school dress for my homework” Frank curtsies and looked at him Mother with fear.
“I did but you know damn well we do not go around walking around the house in our underwear, now get dressed properly then you can leave the room and be quick about it, really”
“Yes Mother” Frank curtsied and then started to put back on his dress and petticoats.
“I’m sorry Fiona it really was my fault, please don’t punish him later” I said looking over at the poor boy who never chose this lifestyle but was born into just like poor Thomas unlike Mark and David who actually had a choice about this style of life.
“Nonsense I will hear no more about this, Francine knows the rules and knows that punishments follow for any rule breaking, I expect you to make sure that you take the same stance with your new husband, you can not have a sissy disobey you no matter what reason they have for why, rules are rules, I guess I am going to have to start locking on your dresses again just like when you refused to wear them, is that so”
“No Mother I am sorry, really I am” Frank said while curtsying.
“You can save you pleading and grovelling for later my girl, now hurry and get out of here, you can stay in your room now till I am ready to deal with you is that understood”
“Yes Mummy” Frank said and curtsied again as he left the room.
“Really Fiona it was my fault” I said as Frank left.
“Sophie I said earlier it was his fault, he knows the rules and that is all there is too it, I do not want to hear another word about this, is this understood”
I remembered now why I haven’t visited my Sister in a while, even Mother has said she was too strict and I honestly thought that she was almost going to bend me over her knee and give me a spanking for disobeying her if I said anything else about it, so decided best to leave it.
“Sorry Fiona I won’t mention it again”
Not a problem” Fiona said. “now would you like to have a look at what I have for Mark before David comes home from work.
“Yes Please that would be a great and thank you for this”
Fiona showed me the contents of each bag, there was a bag for skirts, some dresses, formal ones like someone would wear for working in an office in various colours, a bag with some bra’s. There was some training bra’s and some with boob inserts and she had included a spare set of inserts as well. There was also another bag for younger girl dresses, these were not frilly and quite plain but Fiona explained she still wanted to keep the frillier ones for David and that I should take Mark along to her dressmaker friend as soon as possible to get him measured up for his own, also included were a couple of school dresses,
Once we had looked through the bags, Fiona looked at me all serious and said “Now you know David will be home very soon and I have discussed with Mother we are not sure you are quite ready to take on a sissy of your own so we both think it will good for you to prove this to us, once David arrives home I will explain to him that you are going to get him ready tonight, then I want you to take him up to the nursery, undress him, give him his bath and then you are going to get him ready, I want you to put him on the changing table and insert his butt plug which has a tube to inflate you are to squeeze this 3 times, but make sure you give it a good squeeze then you can remove the tube, before putting putting on his nappies are you understanding so far” My Sister was always so bossy to me, god only knows what she will be like with Mark when she gets her hands on him. “Yes Fiona I can do this, I know I have not been so active in this side of the family but I am ready now to be an active part of our family traditions again”
“Good I am glad to hear it, so I have David wear a disposable with a soaker in and then on top of that you will put on a towelling nappy with the nappy pins and then on top of that 2 pair of plastic pants, you will then dress him in the clothes I have left out and then bring him downstairs to the kitchen for his tea, you will find everything on the cot for you, once you have undressed him, give him his dummy, he knows he is not to take this out unless I give permission so please make sure this stays in and he drops it at all let me know, understood”.
“Yes Fiona I understand” I definitely haven’t missed this, she seems so polite when I came round earlier now she back to normal self, I Didn’t think it would last for long.
“Good now I am going to run his bath, while I am gone can you place everything back in the bags thank you, I will be back in a moment”
As Fiona left I placed the clothing back in the bags and then sat down on the Sofa and waited for Fiona.
About 10 minutes later, Fiona appeared with David dressed in his business suit, I didn’t even hear the doorbell go, surely she doesn’t let him have a key, Mark is never having a key to my house, he will knock and wait for me to allow him to enter I thought.
“Right Sophie, I have explained to Davina that you are going to be charge of his nightly routine tonight and that he is to be on his best behaviour, Off you go and I will meet you both in the kitchen. Thank you”
I really was getting sick of my Sister being so controlling of me like this, but I guess this is just how she is and if I want my hands on my trust fund I best do as she says and keep her happy.
“Yes Fiona no problem, Davina I guess you best come with me please” I almost wanted to drop her a curtsy myself but thought no best not push it, she would never see the funny side of it.
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From the rules near the top of our index page at,
http://buffalobetties.net/storytime/index.php?topic=30.0
"Story Part Sizes - Parts can be no more than about 8.5k in size. For standard browser text, that's about 2 screens worth here, or about enough to fill 6-8 of those little text boxes you type or paste your part into. It won't be a strict limit. A little over won't matter. Over-sized parts make oversized data packets which can be lost or corrupted during backing it up, archiving, repairs, or retrieving it. Many servers won't even accept oversize data packets, so would make it difficult if we have to move it or us to another server."
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From the rules near the top of our index page at,
http://buffalobetties.net/storytime/index.php?topic=30.0
"Story Part Sizes - Parts can be no more than about 8.5k in size. For standard browser text, that's about 2 screens worth here, or about enough to fill 6-8 of those little text boxes you type or paste your part into. It won't be a strict limit. A little over won't matter. Over-sized parts make oversized data packets which can be lost or corrupted during backing it up, archiving, repairs, or retrieving it. Many servers won't even accept oversize data packets, so would make it difficult if we have to move it or us to another server."
Hi Betty, sorry about that, at a suggestion maybe put a character limit on how many can type as it hard to keep a note of how much is too much.
I don't think many people are interested in this story anyway, so probably won't post any more and maybe try a different site
If you need me to modify any of the post sizes, let me know
Thanks.
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The story is developing - but the chapters parts are getting longer - maybe a simple breaking the
chapter parts in two or three sub-parts will full fill the limits - or simply after a page (4-5 paragraphs)
continue on a new date time posting - it is easy to wait for the next posting be it right away or a day
later. There aren't many story writers these days would hate to lose you !
And best wishes for the Holidays !
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It’s a very nice first story. Please continue!
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Yes the story is very good keep it up. I also agree you could make the chapters smaller but if possible with your busy schedule upload the chapters a little closer together please and thank you
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Thanks all for the kind comments, I can make the parts smaller if that is what people want.
Thank you for taking the time to read and please feel free to comment if you are enjoying the story or not, it helps motivate me for the next part.
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I love this story, please continue!! Love Marci
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I held out my hand for David to take and walked with him up the stairs. As I got to the top of the landing I could see a door marked nursery with girly babyish writing on a wooden sign. I unlocked the door and then went inside, what I found was quite amazing. The walls were painted pink with a fairy boarder going around the middle of the wall. The carpet was also pink, on one side of the room was a large wardrobe which had mirrors on the doors a number of shelf's which looked piled high with plastics pants, nappies and various baby toys. On the other side of the room was a generous size cot which held restraints and had high sides and also looked like had a locking top that could be attached that effectively would act as a cage for the impending victim and next to that was a large size Rocking horse, which had a saddle that you could attach a dil-do too and above on the wall was various different sizes ones that I guessed were used for that purpose. On the other side of the room was a changing table with straps attached. Also dotted around the walls were photos in various sizes of sissies in full baby dress while sat either on the rocking horse or in the cot. I told David to get undressed while I took a good look at the photos, most of them were of David and Frank but I could also see a few of Thomas and some other people I did not know, some were of adult men and some were boys. “Who are all these other photos of Davinda?” I asked.
“Mistress often babysits for other sissies and whenever somebody spend time in the nursery, Mistress always makes sure that a photo is taken of them for the wall. I noticed as David was getting undressed that he had on a Basque attached to stockings under his business suit, “Does Fiona have you were them all the time under your suit?” I asked.
“it’s not always a Basque and stockings but I do have to wear some form of lingerie underneath every day Mistress”.
I decided to take a nose in the wardrobe and found it stocked with so many dresses and petticoats and could see a number of boxes that contained other baby items such as bonnets, mittens and booties,. “Do you have a favourite to wear? I laughed at David while I flicked through all the dresses, I took a few of them out to get a better look and starting picturing Mark wearing something similar, I can’t wait to see his face when I tell him that at least twice a week he is going to be wearing full baby wear and eventually going to be sleeping in his own nursery, speaking of which I must ask Fiona where she acquired the cot and rocking horse from.
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Thank you for the update looks like things can and will get interesting
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Message to the author, BabyLock.
This is a very good story and I for one would love to read how it continues.
If you are choosing not to continue this story on this site then can you please advise of where your story is being continued ?
Thankyou.
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With Fiona's instructions firmly in mind, I assumed control of David's nightly routine with a newfound sense of authority. First, I reached for the dummy off the shelf and popped it in his mouth, ensuring he understood the gravity of disobedience. He accepted it with a resigned nod, the rubber teat was quite large and completely filled his mouth.
Following the ritual of his bath, I led David to the on en-suite bathroom where the bath Fiona had prepared awaited, the bath had lots of soapy bubbles and had a very strong smell of raspberry, As I helped him step in the bath I couldn't help but notice the mix of resignation and anticipation in his demeanor. With gentle hands, I lathered him up, he skin was smooth all over and I took extra attention to wash his bottom, moving the sponge inside and giving it a good poke. His sissy stick was locked away tightly in a enclosed chastity device with just as few little holes showing in the tight metal, which I lifted carefully and washed underneath. all the while I was bathing him I made little comments about his life and how he must love being a little sissy as he has no fight what so ever, no real man would allow this I laughed.
Once he was clean, we proceeded to the changing table, with meticulous care, I laid him down on his stomach and then took the lube and the inflatable butt plug, I inserted it then ensured it expanded inside him with 3 firm squeezes as per Fiona's instructions. David squirmed uncomfortably but didn't scream out at all, I gave it another little squeeze and laughed saying this will be our little secret ok and then laughed some more.
With the plug securely in place, I turned him over and began the process of layering his nappies, I started with the disposable diaper and placed the large soft soaker inside and then had him lift his bottom as I placed it on him, on top of that, I added a toweling nappy, securing it in place with the required nappy pins. Finally, I pulled on two pairs of plastic pants, their snug fit ensuring hopefully no leaks would escape, I wondered how much of a wetter David was.
Turning my attention to his clothing, I helped David stand up and then went to the cot where Fiona had left out a satin top almost like a training bra but it was very juvenile looking and covered in lace, it was pastel blue with baby pink lace. I helped him into it and made sure it was set right. Next was a short satin frilly dress which had built in petticoats and the dress was lined with plastic, the dressed matched the colour of the top. As I helped him into it, I couldn't help but listen to all the crinkly plastic from the lining, after that was a matching pair of rhumba panties also lined with Satin which I pulled over the big bulge of his nappy, noticing that it was quite wide and he couldn't close his legs fully. Next was matching booties that were padded out and mittens that were also quite thickly padded and followed by a large matching bonnet that once I put it on him and straighten it out I could see that he view was quite restricted and he could only see forward. I took the opportunity to fluff out his dress and puff up the sleeves as I was doing this I could hear the loud crinkling of his outfit which made me smile thinking I must get Mark into something like this very soon. Lastly on the cot bed was a set of blue leather reins with pink lace edging but what surprised me was the tiny little bells dotted around the reins, they also had a padlock and leash that looped over both sides.
Smiling I shock them out and placed them over his head and locked them around his waist and then attached the lock and looped over the leash.
Satisfied that he was now ready, I took the leash of his reins and told him to start walking, as he walked he made so much noise what with the bells and the plastic lining on everything I couldn't help laugh saying you wont be going anywhere without somebody noticing will you. I carefully held his reins and led him downstairs to the kitchen where Fiona was waiting for us. With each step I felt a surge of pride knowing I had executed Fiona's instructions meticulously and as we entered the kitchen I wondered what she would say.
Normal updates should hopefully resume regularly again now and I will try to keep the parts shorter as mentioned. sorry for the long delay.
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As I entered the Kitchen Fiona was waiting for us, she came over and said lets take a look at how you did then, she started at the top with his bonnet and straighten it a bit more, she then fluffed out his dress and checked his reins commenting that these could of been a bit tighter, she stretched out his rhumba panties and checked inside his nappy commenting that at least his butt plug feels nice and secure, over all not a bad effort, however you took quite some time and it almost past his bedtime but over all I am satisfied. She then took hold of his reins and looked at David and said ok I think you should thank your Auntie Sophie for getting you ready, don't you. David looked at me and performed a curtsey in the best possible way he could in his current stats, his loud crinkling of plastic and bells making lots of noise I could barely hear him say thank you through his large dummy. Fiona said very well go get in your high chair and wait for Mummy as she unclipped his leash from his reins. I watched David waddle over to the other side of the kitchen where a large wooden high chair was in white with pink padding with the front tray open, it was quite surreal but I thought I must get something similar for Mark, looks like I got a lot of spending coming up but it will all worth it to get my trust fund.
Fiona speaking caught me from my gazing at David as she said that although it been nice seeing me its time for me to go, she said she will keep in touch and be on hand to help with Mark and will look forward to meeting him soon. She then walked with me to hallway and called for Francise to come and say good bye, Frank appeared at the top of the stairs but the maids uniform was gone and he was now dressed in a green gingham school dress with little white socks and black flat shoes, he came down and gave me a kiss good bye then Fiona helped me with the bags to my car and wished me a safe journey.
Once I arrived home and settled I sorted through all the bags, I created a nice little outfit for Mark to wear on his first day, nothing too adventurous I wanted his first day to be quite relaxing for him, It's going to be his first time properly dressed as my sissy and I wanted to make him feel right at home. I selected a faux leather skirt, it was mid thigh length, a white blouse that was quite plain but see through, a black bra with built in inserts and pair of black satin panties and black tights with some 2 inch heel shoes the same ones he wore the other day. I decided I won't bother with a camisole as I wanted him to keep seeing his bra through the blouse I also didn't pick any makeup but thought it might be fun to add some every so often though the day.
With his outfit sorted I decided to take a shower then off to bed as Mark was due to arrive at 9am tomorrow I wanted to be fresh and ready, I just hope he decides to turn up I mean he has too otherwise his pictures will be sent to everyone, well only time will tell not long now I thought as settled into bed.