Crystal's StorySite storysite.org
by Caroline Richards
Mistress Helen took me by the hand as She pushed the doorbell. It was about 3.00pm on Saturday, and a large, blonde and beautifully proportioned woman came to the door and greeted my Mistress warmly. This was Mistress Helga and I was to stay with Her for the next month until the day of my 18th birthday. Mistress Helga was a professional Mistress in her mid 30s who specialised in teaching boys to be little girls very little girls and, as She had known my Mistress for some time, She was more than happy to take me in and look after me if that is the right term.
i was brought here so I could consider my future and decide in what style I wanted to live the rest of my life. So this was to be an important month because the decision that I made would live with me forever.
Mistress Helga chatted to Mistress Helen for a few minutes and then they kissed each other goodbye before She took me inside and closed the door.
"Take off all of your clothes in the room across the hall immediately and wait for me on your knees Sissy", She said.
I walked into the room shaking with nervous tension and immediately stripped off all of my clothes and put them in the basket provided. I wondered how long it might be before I dressed in boys clothes again. I was 511" tall and about 180 pounds and reasonably well built. my cock was about 7" when erect so there was little doubt I was a healthy growing young man. Did I want to be that way for the rest of my life? I didnt yet know the answer to that question.
Mistress Helga came into the room after nearly an hour had passed during which time I stayed on my knees, with all sorts of thoughts going through my mind.
"Good to see you have obeyed me Sissy and stayed on your knees. I have been observing you on video for the last hour and I like what I see. I think you have a strong submissive streak that will help both of us to provide you with a wonderful Sissy-like environment over the next month. Now crawl over here and place yourself over my knees so I can give you the first of your spankings for the day. Regular spankings will be part of the daily routine from now on to help me reinforce that you are a submissive little Sissy."
Mistress was dressed entirely in leather and She had her hair pulled back into a ponytail that sat high on Her head. Her large breasts bulged from the top of Her tight leather halter-top, and She wore a leather skirt that left Her midriff exposed. Thigh boots with 4" heels and a broad leather studded collar completed the picture. She was tall and powerful and Her looks were very striking, and I trembled as I did as I was told and lay down across her knees and waited for my punishment to begin. I could smell her female scent mixed with her perfume and the aroma was delicious. I could not help myself and my cock began to grow erect. Mistress noticed this immediately and said that my cock was something that obviously needed to be better controlled than it was. I shuddered to think what She meant by that, but my thoughts shifted to other things entirely as the paddle She had in Her right hand came down hard on my left buttock. I flinched and groaned a little before She started to smack each buttock in turn. After 20 strokes on each buttock I lost count and started to squirm and groan as each blow landed on my increasingly sore bottom.
"Lie still Sissy and take your punishment. This is something you need to accept as part of your transition, even if it is very unlikely that you will ever get used to being spanked like this."
When She had finished I was almost in tears and my bottom was sorer than it had ever been.
"On your knees again Sissy and wait for me."
Mistress left the room briefly and came back in with a bag of implements. She took out a steel collar and locked it around my neck before attaching a 4 long chain leash to it with a padlock. She then locked a set of steel shackles on my legs. The connecting chain was only 18" long so I had very little capacity to walk quickly. She then led me out of the room and downstairs into Her basement where there were two main rooms. The first was Her dungeon and She led me inside before locking me in a low cage. It was about 6 long, 3wide and 3 high. I had to crawl to get in it and then She closed and padlocked the door without saying a thing. She left leaving only a dull light burning so I could just make out the rest of the facilities contained within the dungeon. Perhaps surprisingly, I had never seen inside such a place before and my mind was in turmoil as I examined the array of whips, chains, gags, benches and racks set up within the room. What had I let myself in for? The decision to come here was my own but, having arrived, the understanding was that I would be kept here for the full month no matter what happened. I was in the cage without food or water for hours and I eventually fell asleep with my bottom still throbbing from the first really severe spanking of my life.
I assume it was next morning when Mistress Helga came back into the dungeon. She released me from the cage and allowed me a drink of water before letting me go to the toilet and then have a shower in the bathroom connected to the dungeon.. However, She did not release me from my collar or shackles. When I came out of the bathroom I felt much better and Mistress gave me a plate of cereal to eat. I was ravenous and said "thankyou Mistress" as she handed it to me.
"Today will be a big day for you Sissy, and we have lots of work to do. But before we start it is important that you understand the rules of this house, and that any breach of those rules will lead to severe punishment in addition to your regular spanking."
Mistress outlined the rules to me which were that I referred to Her as Mistress Helga at all times, that I never spoke without permission and that I was to get down onto my knees and bow my head until it touched the floor whenever I came into Her presence. I was to remain that way until given permission to move.
She asked me if I understood these rules and I replied that "Yes, I do". This was the first of what were to be many mistakes over the next month.
"Sissy, didnt I just tell you that you are to address me as Mistress Helga at all times. Over my knee Sissy. Quickly girl." I moved as quickly as my shackles would allow and I received another severe spanking at the end of which I was blubbering like a baby. my bottom was so sore.
Mistress then led me to a frame in the dungeon and She locked me in a spreadeagled fashion to it.
"Part of being a Sissy is having your capacity to ejaculate under strict control. You will only obtain sexual relief with my permission, and the way in which I intend to achieve that is have you locked in a chastity belt for long periods. You will be freed from it only when you have pleased me with your efforts and at those times I will also allow you to cum. Punishment and reward are essential elements in training a good Sissy." She then went to a cupboard and got out a box in which was packed my chastity belt.
"Your Mistress was able to give me your precise measurements so this should fit you perfectly first time dear."
Mistress Helga attached a string to my cock and then rubbed baby oil into it before sliding it into a stainless steel tube, using the string to pull my cock through the tube. The tube was then locked behind my cock and balls so it could not possibly slip off me. The end of the tube had a slit around the circumference so another tube could be pushed inside it to form a sort of extension.
"You will need to be able to pee properly with this on Sissy and this catheter will help you to do that."
She gently inserted the catheter into my body through the head of my cock. A small hollow metal tube shaped a bit like the head of my cock and the beginning of my shaft was next. She squeezed gently until the head of my cock was inside the head-shaped portion of this new piece and allowed the catheter to pass through the small pee hole in the end. The piece was then inserted into the slit in the main tube and I could see that it was designed to accommodate the expansion and contraction of my cock. The two sections would slide together and apart as required. Two tiny chains attached to the sides of each section ensured that they were unable to separate when my cock became erect. Mistress then used a small tool to warm and expand the exposed end of the catheter and fold it back over the head of the tube where it locked into place as it contracted around the beginning of the narrower section covering my shaft.
"Every good Sissy also needs her arse completely filled dear", said Mistress Helga as She inserted an expandable butt plug deep inside me.
It had a keyed lock that opened a flange inside my rectum ensuring that I could not possibly remove it by myself. Finally, a stainless steel front plate which clipped on to the tube and made sure I could not get near my cock was locked in to place with flexible steel belts around my waist and passing between my legs and locking in the small of my back. The belt fitted perfectly and it seemed to be comfortable although time would tell.
"Lets see if this works shall we Sissy", said Mistress Helga as She pumped up the inflatable butt plug.
i could feel it expanding deep inside me and eventually that caused my cock to want to become erect. My cock filled the tube and I could feel the two components of the tube slide apart a little as my cock increased in length. I felt so helpless and yet in a strange way so comfortable.
"Well what do you say Sissy?"
"Thankyou very much Mistress Helga", I said as She started to release me from my locked position.
After I was released Mistress attached the leash to my collar again and led me around the dungeon to see if I could walk freely with my chastity belt in place. The belt was reasonably comfortable although very tight against my skin and there was no way that I would be able to access my cock at any stage while it was in place. Mistress Helga was obviously very pleased with the fitting.
"Follow me dear", She said, while leading me into the adjoining room that proved to be a fully equipped nursery. A wall of cupboards contained a complete array of baby clothes and nappies and toys and other implements designed to make a babys life as comfortable as possible. In the corner was a full-length cot although it was effectively a cage on legs with bedding placed inside. The mattress had a plastic covering to protect it from moisture.
"This is where you live when you are not with me receiving training Sissy and now get up onto the changing table and lie on your back."
i did as I was told as quickly as possible because another spanking would have been unbearable. Mistress then raised my legs and slid a thick nappy under my bottom. She then powdered my bottom and pinned the nappy firmly into place. A pretty pair of transparent pink plastic panties was next and they fitted snugly around my waist and my legs.
"There you are Sissy. You are looking more like the baby you are to be for the next month already. I do not intend to change you frequently so you will just have to put up with wet nappies for a lot of the time. If you dont want to soil your nappies you will learn to use the potty when I release you from your cot each morning. Do you understand me Sissy?"
"Yes Mistress Helga", I said quickly to avoid punishment.
Next came a full-length cotton body suit that zipped up the back. It was pink with white frills at the end of the sleeves and around the ankles. Woollen booties on my feet and mittens on my hands were followed with a pink and white bonnet that Mistress tied gently under my chin.
"Nearly finished Sissy, just a few more bits and pieces and we can go upstairs and relax for a while."
Mistress then placed what looked like a white frilly tutu around my waist. It made me look very much like a baby girl. A very large dummy was pinned to the breast of my body suit and, lastly, bracelets and anklets put on each leg and arm. These bracelets tinkled as I moved and Mistress said they were important because it meant She could always hear where I was if I was left alone for a short time.
Mistress then removed the leash from my steel collar and opened a new cupboard to reveal a pink plastic baby harness made to fit me. Mistress Helen had obviously given Mistress Helga all of my measurements.
"Hold out your arms Sissy while I slip this on you dear," She said.
i quickly did as I was told and Mistress put my arms through the harness and buckled it around my neck as well as between my shoulder blades and around my waist.
"Now follow me Sissy, and because you are a baby girl you are to crawl not walk."
i followed Mistress out of my new bedroom and crawled, my little bells tinkling, with some difficulty because my feet were still shackled, upstairs to her lounge room where She put me into a playpen that She had set up near one wall. A long chain was then locked from my collar to a ring set into the wall. I was to remain in the playpen for the rest of the day as Mistress went about Her business. Although it was a Sunday She took many phone calls to set up appointments in Her dungeon over the next few days. Mistress told me that under no circumstance was I to try and stand up and that I was to practice dressing and undressing the five dolls She had put in the playpen for me.
"Keep your dummy in your mouth at all times as well Sissy dear, learning to suck properly is an important part of your training."
"Yes Mistress Helga", I said quietly.
She left me alone for what must have been three or four hours and I did as best I could in dressing and undressing the dolls. Finally She came into the room with a babys bottle and a plate of warm baby food. After putting a pretty bib on me She fed me slowly with a spoon and then told me to lie on my back and drink the bottle of baby formula that She had prepared. It was warm and sweet - quite nice really. I finished it quickly and Mistress, seeing I was so thirsty, prepared another one for me straight away.
"You have been a very good girl so far sweetie, so you can have a sleep if you like."
i was very tired and I said I would like to have a sleep, so Mistress got me a knitted woollen blanket from Her room and put it over me as I lay down. I was so warm a cosy I must have gone to sleep immediately and when I woke the room was dark and I needed to pee badly. Mistress must have heard my little bells when I stirred because She came in almost immediately to see if I was all right.
"May I have permission to speak Mistress", I said.
"Yes dear, what is it?"
"i need to pee very badly Mistress, may I go to the toilet."
"Of course you cant you silly girl. You have not been potty trained so you will just have to pee in your nappy."
i had no choice and the warm fluid flowed out of the catheter and began to spread through my nappy. Mistress seemed very pleased at all of this and said that peeing in ones nappy was something all good babies did and it was nothing to be ashamed of.
An hour or so later I was fed again and I must admit to looking forward to being able to suck on my bottle and swallow that lovely warm sweet fluid. The only problem was I had to pee myself again very soon after.
About 8.00pm Mistress led me back downstairs, changed my nappy and plastic pants and put me in a full-length mauve nightie before locking me in my cot for the night. My shackles and collar came off but they were to be put back on me before I was released in the morning.
This routine went on for a week. I received a spanking each morning before being allowed to bathe and go to the toilet, after which I was put back into my nappies and baby clothes and led upstairs to my playpen. I was left alone for extended periods as Mistress dealt with her regular customers, but I didnt mind too much as it gave me time to think seriously about my future. That was, after all, the reason I was here.
On the next Saturday my routine started out much the same, except that Mistress told me that I had been such a good baby all week that She would take my chastity belt off for the rest of the day. That evening before putting me to bed in my cot, She led me into Her bedroom and told me to crawl up on her bed and wait for Her. She went into the bathroom to change and came out dressed in a long flowing black negligee through which I could see her full and naked breasts. She then sat next to me and picked up the phone on Her bedside table.
"You can come in now Serena," She said, and soon after a middle- aged but good-looking woman with large breasts pushing out the pink nightie she was wearing came into the room. I could clearly see Her large nipples through the flimsy nightie and the sight made my cock start to become erect in anticipation.
"Serena, this is Sissy. she has been a good little girl all week and I am sure she would like to get close to you."
Serena too sat next to me and before I knew what was going on she had taken my head in her right hand and drawn it close to her breast. With her left hand she untied the front of her nightie and then gently lifted her right breast to my mouth and pushed her nipple deep inside me.
"Suck me gently Sissy", She said, and as I did so warm fluid began to flow into my mouth. It was beautiful and I felt loved and wanted and very, very submissive all at the same time. Serena breast-fed me for about half an hour during which time I wet my nappies. But no one cared and the feeling of being wet and on Her breast heightened my pleasure. She was aroused by this I am sure because her nipples became very hard. Mistress Helga then slipped Her hand inside my nappy and rubbed me gently until I orgasmed while I was still sucking Serenas beautiful breasts. The sensations I had felt in the last hour or so were wonderful and I was so grateful I snuggled into each woman to thank them. They both smiled at me, and then Serena changed my nappy before I was allowed to go to bed that night lying between these two beautiful women.
On the next day my routine was back to normal with the chastity belt back in place for at least the next week. Mistress Helga was very strict and when I slipped up a couple of times I got very severe spankings in addition to my regular morning spankings. Serena came to see me twice more and I really enjoyed being on her breast, but I think Mistress Helga was just a little jealous that She could not provide me with milk from Her breasts.
Finally, the four weeks finished, and my Mistress came to pick me up on the Saturday morning. Mistress Helga had given me one last spanking and then allowed me to dress in my male clothes again. She gave Mistress Helen a bag with "a few things that might be useful later on" and Mistress took me by the hand and led me to the car. Tomorrow was decision day.
Chapter 2 The Beginning
i was having a miserable time at school. Just 14 years old, two older boys and two older girls were bullying me unmercifully almost every day. Why me? As far as I knew I had done nothing to upset them, but they took it out on me both physically and emotionally. I fought back when I could, but it just made matters worse. The teasing and taunting by the two girls was the worst of all, because I couldnt even respond by fighting them as I had done a couple of times with the boys. As usual, the teachers were no help, because they were never in a position to witness the treatment that I was receiving. After one particularly bad day I was extremely upset by the time I got home and I guess that is why things developed as they did.
Mum and I lived alone and had done so for as long as I could remember because my father left before my first birthday. Mum had lots of friends, but She never remarried and did not seem to be all that interested in any relationship with another man. She now worked in a beauty salon for a lady named Elizabeth who was also single with a 12-year-old daughter. I didnt really know them, having only seen them on a couple of occasions when I went to where Mum worked after school.
Mum was now 32 years old and still very attractive. She had been only 18 when I was born and perhaps that had been the problem with Her marriage, but She never wanted to talk about those days.
She worked late on Fridays and on this evening it was 8.00pm before She came in the door. I had already done my usual tasks around the house., including most of the cleaning, because it was important to help given Mum was working full time. We ate dinner together, but I didnt want to talk much and I guess my anger and hurt at the way I had been treated at school was starting to show in the way I behaved towards Her. It was unfair of me, because Mum was always very good to me and I loved her as much as any teenager will admit to loving their Mother.
We sat together watching TV after dinner and after a while Mum asked me what was wrong. Initially I said that nothing was wrong but, of course, She could see I was lying and kept asking me questions until I told Her that I was miserable at school and wanted to leave because I was being bullied. On making this admission I burst into tears, which seemed to shock Mum at first, because it was unusual for me to be so upset.
i then went upstairs to bed and shut the door. I was so miserable, and after a while Mum came into my bedroom to see that I was still crying. She sat down next to me but seemed unsure of how to respond to my distress. Eventually She suggested that I come into Her bedroom and talk to Her while She got ready for bed. I agreed and I sat on Her bed while She went into Her bathroom and changed into Her nightie with a pink and white negligee over the top.
When She came out She said, "Come and sit next to me darling. I want to see if I can help you forget your troubles at least for a little while. I hate to see my darling boy so upset."
i couldnt stop crying, but I shifted over and sat next to Her and almost immediately I felt a little better. She put Her arm around me and pulled me gently closer to Her and then lay my head on Her breast. She smelled wonderful and the silky feel of Her negligee on my face and the softness of Her breast had an immediate effect.
"How is that darling? Does that make mummys boy feel better?", She said, smiling down at me as I continued to snuggle into Her breast. I had to admit that it did and I mumbled something to that effect. I rather shyly put my arms around Her and gave Her a hug something I dont think I had done for years, and I felt very close to Her and said so.
After about five minutes I had settled down a lot and it was then that I noticed my cock was becoming erect. How embarrassing was that? But as with most boys of my age it had a life of its own at times and, if anything, it became harder still as I continued to rest my head on Mums breast. Finally, Mum also became aware of what was happening and She said something to the effect that She understood, it was all right and that I was not to worry.
She leant down and kissed me gently on the forehead and the smell of Her and Her gentle touch nearly made me explode. Then, almost without me being aware, She undid the lace at the front of Her negligee exposing Her lacy pink nightie. With one hand holding my head She used Her other hand to push Her nightie down and expose Her left breast, which She cupped in Her hand, before gently guiding my mouth to Her nipple.
"Here you are honey", She said. "Suck on my nipple just as if you are my little baby again and it will help to make all your troubles disappear for a while at least."
i couldnt believe this was happening and it was like being in a dream as I felt Her now erect nipple push into my mouth. Almost by reflex I began to suck gently and I immediately began to relax and feel warm and cosy. I am sure Mum liked it as well because I could hear Her breathing come in short sharp bursts and her body move slowly as She kept using Her hand to hold my head tight against Her.
Eventually She lay down on Her bed and pulled me down beside Her, with her nipple still inside my mouth. She talked to me quietly, soothing me, and at the same time moved Her free hand inside my pyjamas and over my erect cock. It was too much for me, and I came in great spurts inside my pyjamas and over the sheets. I had never felt like that in my life before and I wanted to move quickly away, but Mum continued to hold me tightly and insisted that I remained lying beside Her for some time while She continued to whisper to me and caress me.
Eventually She let me move away from Her and we sat together and talked about all sorts of things. I felt a lot better and thanked Her for being so good to me. She asked if being so close to Her embarrassed me and I said that it didnt. In fact I really enjoyed being close to her in that way.
"Darling, I think that what we did tonight was wonderful and if things ever get you so upset again remember that your Mummy is here for you, and will look after you. I think the only thing we need to do next time, assuming you think there should be a next time, is take steps to stop so much mess getting all over the bed clothes. Do you agree?" I agreed and then She said, "Now, clean up and then come back to bed with me, because I want to snuggle in to my darling boy all night."
i woke next morning quite early after having a wonderful nights sleep lying close to my beautiful mother. It was Saturday, and I was in a junior football team that had a match in a few hours so I needed to hurry. I went downstairs and made breakfast and then brought it into Her bedroom. She woke when I came back into the room and I gave Her the breakfast on a tray not knowing what to say. It didnt matter as She took the tray from me, smiled, said good morning and then kissed me. "I love you sweetie", She said. "i love you too, Mummy."
Chapter 3 Back in Nappies
The memory of that night stayed with me throughout the next week at school, which was just as miserable as the last. I often ended up crying myself to sleep during that week because the bullying was becoming unbearable. My schoolwork was suffering as a result, not that I was ever much of a student. I tried hard but learning didnt come easily.
When Friday night came around I did my housework and waited for Mum to come home. She was late as usual because Fridays were the busiest day at the salon. Mum asked me how school had been that day and I told Her that it had been as miserable as ever. I suppose I expected Her to then say or do something like the previous Friday, but She simply listened carefully and told me that I would need to persevere, although She was willing to go and see the teachers if I thought that would help. I said no to that idea very quickly because I knew it would just make things worse when those bullying me found out.
Finally, I could take it no longer and I had to say something.
"Would it be all right if I came and sat next to you Mum?", I said rather nervously.
She smiled at me before answering "Of course dear. Come over here and sit down near my feet and tell Mummy all about your feelings." She was in Her own chair and so it was not possible to sit next to Her properly. I moved over and sat at Her feet and She put Her hand on my head and pulled it close to Her.
"What did you want to talk about darling", She said.
i stumbled looking for the right words and finally said, "Can can I sleep in Your room tonight Mummy like we did last week, or dont You want me too?" This wasnt easy.
She thought for a moment and then said, "If you really want to you can, but I need to know that it is something that you really want to do. I do not want you to feel as though you are being pushed, and you will need to explain why you think I should allow you. If you do sleep in my room tonight we will also need to do something to prevent the mess that you made all over the sheets last week."
i blushed at the memory and then tried to explain my feelings and my need to be with Her because I loved Her and because my life was hell at school right now. Finding the right words was difficult and Mum listened quietly for a few minutes as words tumbled out of my mouth.
Finally, she looked down at me smiling and said that it would be all right and that I could sleep in Her bed tonight if I wished.
After a while we went upstairs and I changed into my pyjamas before knocking on Mums bedroom door to see if it was okay for me to come in now. Mum said that it was and I opened the door and walked in. She was sitting on the bed looking absolutely beautiful. She had tied pink ribbons in Her shoulder length blonde hair and She still had some makeup on. For some reason She still had on a bra and panties because I could see them through a very sheer black satin negligee that I had never seen before. Perhaps She had bought it during the week. I guess I looked a little stunned at seeing Her this way and I looked down at the floor very quickly.
"No need to be shy with your Mother dear. Come over here and give me a kiss."
i did as I was told and I kissed Her gently on the cheek before She returned my kiss by gently touching Her pink lips to my mouth. I immediately began to get hard and it was rather obvious in my pyjamas.
"Now we agreed we would need to do something to prevent the mess of last week, so take off your pyjama pants and lie on the floor for me darling while I get your nappies from the drawer."
Nappies? She must be joking I thought, but She wasnt. I hesitated to do what I had been told and Mum looked at me carefully.
"Honey, we need to do this if you are to stay the night in my bed. If you dont want to wear nappies that is fine, and I will understand, but you will need to sleep in your own bed."
i was trapped by my emotions. Could I suffer the embarrassment of wearing nappies so I could sleep close to my Mother again? "Okay, Mum, I suppose it will be all right", I said finally and without a great deal of conviction.
"Well then, do as I have told you and get your pyjama pants off and lie on the floor."
i did as I was told, and lay down with my bottom bare and my cock erect. Mum got a large fluffy cloth nappy out of the drawer, slid it underneath my bottom and then pinned it on me with two large safety pins. Next came a pair of transparent pink plastic panties that I suppose were necessary if Her bed was to remain dry. How did I feel? Ridiculous on the one hand and warm and snug on the other. I suppose as long as no one but my Mother knew that She had put me in nappies it would be okay.
"Stand up and let me look at you darling? Mmmm I thought so. Your pyjamas wont fit back on over the nappy. We need to do something else. I have a nightie that I no longer use that you can wear if you want too."
i had gone this far so what the heck. I said that would be okay and Mum took off my pyjama top and slipped a sweet smelling pink nightie of Hers over my head. It had long sleeves and came down nearly to my ankles. There were lace ties around each wrist and a lace tie that closed the nightie at the front. It was really comfortable I had to admit, especially compared with my old scratchy pyjamas.
Mum told me to turn off the light and then get into bed. She lay down next to me and then asked me to reach inside her negligee and remove Her bra. I fumbled for a bit and Mum said, with a laugh, that I needed a lot more practice. When it was off She pulled me to Her and guided my mouth to Her breast as She had done last week. The feelings I had for her then were indescribable. My cock was rock hard and I could smell her perfume and feel her nipple deep inside my mouth. As I sucked gently on Her nipple Mum slid Her hand inside my nappy and I could feel her long red fingernails stroke my belly before she began to stroke my cock. I came almost immediately and I could feel Mum hold me tightly to her as my body shuddered with passion. She held me for a long time before starting to stroke my cock again. It was not long before I came again and this time it was even better. I knew my cum was all over Mums hand but She obviously didnt care. As we lay together She talked to me quietly and told me that she loved me and that everything would be okay.
As She talked to me She withdrew Her hand and put her fingers to my lips. I could taste the cum on her fingers before She whispered to me that She would like me to lick her fingers clean. I hesitated only briefly before allowing her to push each finger into my mouth one at a time. I licked them carefully and lovingly.
i slept soundly for the rest of the night, and awoke to see that Mum was dressed and sitting on the edge of the bed.
"How are you this morning my darling?", She said as I sat up and gave Her a hug. I couldnt have been better.
"You look so pretty in your nightie, perhaps you would like to stay dressed that way for a while darling. I know there is no football today, and I thought you might like to spend the day as my little baby girl. We would have all day to do things to please each other."
Was She for real? Baby girl. Is that how She thought of me? But I had to admit the thought did excite me. My mother had opened up a whole new world for me, but She was also not doing anything without my agreement. I knew if I said no that nothing more would be said.
However, almost without knowing it, I said "Yes Mummy, I would like to do that with you."
Chapter 4 Baby Girl
It was a cold, wet and miserable Saturday so Mum told me to stay in bed for a while as She got a few things ready for the day. She came back after half an hour or so and told me to get up and go to the toilet while She ran a bath for me. I usually showered, and a bath was unusual, but it felt really good for a change. Mum put in some bath salts to make the water smell nice and then left me to wash myself.
"Call out when you are ready to get out dear and I will come in and help you."
i did as I was told and Mum came in with a big new fluffy towel and helped me to dry myself, before wrapping the towel around me and taking my hand and leading me downstairs to the lounge room. She had set out a blanket in front of the heater and there was a bag of clothes and other things nearby.
"Lie down on your back honey and lets see if we can get you dressed properly."
i did as I was told and I must admit it felt really strange to be lying naked on my back in front of my beautiful Mother. While I was in the bath She had really got quite dressed up, and She had on a lovely flowing blue short-sleeved dress with high heels. A gold necklace and earrings set off Her lovely blonde hair, which was tied into a ponytail high on Her head. She looked simply gorgeous, especially with Her pink gloss lipstick and other makeup. She almost never wore makeup at home, but I began to hope that She would do so more often.
Mummy pulled a large nappy from the bag and pinned it on me after powdering my bottom and smoothing it over me with Her hands. New soft pink transparent plastic panties were next, and then She took out a very pretty pink and white baby doll nightie out of the bag. It was so frilly and beautiful that I gasped.
"Do you like this darling", She said. "I bought it during the week especially for you because I was hoping that you would agree to be my baby girl for the day. Here, sit up and let me put this on you."
i did as I was told and Mummy slipped the nightie over my head and let it fall down to just above the bottom of my pink plastic panties. It had laces to tie at the front of the neck and around my waist, and it felt so exciting against my skin that I started to become erect in my nappy.
Next was a pair of pink woollen booties that Mummy tied on with the laces around my ankles, and then a rather tight fitting pink and white woollen cardigan, which Mummy said was necessary to keep me warm. Finally, She brushed my hair and then made two very short pigtails before tying a pink ribbon to each one.
"We probably need to let your hair grow a little more Sissy if we are to do this properly next time. What do you think?"
i didnt know what to say. I really liked this although I was very nervous.
"We dont need it so long that people will notice, but I do want to be able to give your hair a little more style in future. That would be all right wouldnt it darling?"
"Yes Mummy", I said finally. I suppose there was no problem as long as all this was just between the two of us.
"And are you happy to be called Sissy when you are being my daughter?", She said. "You are not really a girl, yet, and I dont think a girls name would be appropriate. Sissy seems to suit the circumstances, dont you think?"
By this stage I couldnt think anything really, so I mumbled that it would be okay to call me Sissy when I was being a girl. When I think back this was a really defining moment in my life because I had accepted that I would continue to be a Sissy for my Mother, at least some of the time.
We were both quiet for a few minutes and Mum sat next to me and pulled my head into Her lap. I relaxed and eventually put my arms around Her and gave Her a hug. I loved Her so much and I did really want to be the best little girl for Her that I could be.
Mummy left me alone for a little while, and when She came back She put a bib around my neck and then gave me a drink of milk from a babies bottle. It was warm and sweet and Mummy held my head in one hand while She placed the teat of the bottle in my mouth with Her other hand. "Suck it for me Sissy", She said. "Suck it and enjoy."
Next, She fed me mashed vegetable with a spoon and finally gave me another bottle of milk. I was warm and full and so content. Mummy wiped my face clean and then kissed me full on the lips. I became very aroused and so did Mummy because She forced my mouth open with Her tongue and pushed it deep inside me. I couldnt help myself, and I sucked on Her tongue as She continued to probe my mouth. I put my hand on Her breast and She took it and placed it down the front of Her dress and helped me place it inside Her bra so I could massage Her erect nipples.
"Does Sissy like being a girl, and being able to play with Her Mummy?", She said.
"Yes Mummy I do", I said without hesitation.
"Thats good dear, because I think we can have some wonderful times together dont you?"
Without waiting for an answer, and with her tongue back inside my mouth, She guided my free hand up inside Her dress and then inside Her panties, which were now soaking wet. She held my fingers near Her pussy and then gently guided my forefinger inside Her.
"A good Sissy will make sure her Mummy feels good honey. Be gentle but see if you can make me love you even more."
i probed gently inside Her soaking pussy and I could feel her move against me before She came with a gentle moan.
"Stay inside me dear, I am not finished yet."
She came again and again over the next few minutes as I massaged Her very gently. Finally, we lay together for some time before I went to sleep with my head in Her lap. When I woke Mummy looked down at me and smiled and gave me a kiss, but She didnt say a word. Eventually I told Her that I needed to go to the toilet, but She gently held me down and told me that as her Sissy I would need to pee in my nappy. I resisted for a while, but eventually had to pee and it flooded into my nappy as Mummy held me close to Her. I should have been embarrassed but I wasnt. It felt so good to do exactly as Mummy told me.
She left me in my wet nappy while She went to get some other items from her bedroom.
"I also bought you some nail polish Sissy that I thought we would use on your fingers and toes. It is pearl colour so it wont be too noticeable but you and I will know you have it on wont we darling."
So She painted my nails and I began to feel more like a little girl than ever before.
Chapter 5 Growing Up
Over the next couple of years my life changed dramatically as I was often dressed, and taught to behave, as a girl when I was at home with my Mother. My school life improved because I no longer worried about the bullying and I became very close to my Mother.
On the day after She first dressed me as a baby girl, Mummy had to go out to lunch with Elizabeth, the lady who owned the beauty salon where She worked. I was resigned to spending the day as a boy again until Mum asked me if I would like Her to dress me as a baby girl again and let me stay that way until She returned home later that afternoon. I was now so sexually excited by what had occurred the previous day that I said yes almost without hesitation. Mummy smiled at me and said it would be a good experience for me to be on my own dressed as a baby girl for a while. It would allow me to think about my life and how it might proceed from now on.
She dressed me in the same clothes I had on the previous day, but this time She also decided to put a very glossy pink long-life lipstick on me. It tasted very creamy and She told me to make sure that I had a full coat of lipstick on when She came home. She left the lipstick with me after showing me how to put it on without making too much of a mess.
i was then put to bed in my own room where I found that Mummy had put a fitted plastic under-sheet on my bed to keep it dry. She told me that under no circumstances was I to leave the room unless there was an emergency and to reinforce this She taped a plastic sheet over the doorway after She left the room. It was like a seal because I could obviously get it off, but there was no way I could put it back without Her knowing that I had left the room. In addition, the safety pins that She used to hold my nappy in place were covered in a special adhesive tape. I could take my nappy off, but there was no way I could pretend to Mummy that I had not done so. Finally, She fed me a big bottle of juice before She left, and gave me another one to drink while She was away, before pinning a large dummy on my nightie and then putting it in my mouth.
"Now you be a good little girl Sissy and stay in bed until Mummy gets home. I expect to find a wet nappy when I get back."
i spent the next four hours lying in bed dressed as a baby and I must admit to loving every minute of it. I wet myself twice during that time and I was a soaking wet little baby girl when Mummy came home about 4.00pm.
"What a good little girl you have been Sissy. Let me change you and then I think I will put you into bed for the night. I know it is early but little girls need their beauty sleep dont they honey."
"Yes Mummy", I said as She put me in a clean nappy and cuddled me close as I got back into bed for the night.
School the next day was fine because I was so looking forward to going home to see Mummy that evening. When I got home there was a note from Mummy saying that She would be late tonight and could I vacuum the house, do a load of washing and start to prepare the dinner. I did all of this eagerly because I knew it would help and please Her.
After dinner, Mummy asked me to sit on the floor next to Her feet while She talked to me about my new interests. It became clear that She would only continue with helping me to be a girl at home sometimes if I really wanted to continue. I would have to ask Her each time I wanted to dress as a girl and She would decide how I would dress and look on each occasion. She would also only agree to help me if I started to take responsibility for all the housework and if I showed Her total obedience at all times. It would also be necessary for me to wear a nappy and a nightie to bed every night of the week no matter what.
i suppose I didnt think too much about any of this because my desire to be dressed as a girl at times was overwhelming. It should have been obvious that I was committing myself, when I was at home at least, to a very new and different submissive lifestyle.
"Well, do you agree with all of this honey?"
"Yes Mummy, I do agree. I want to do this and I want to be able to be close to You like we were in Your bed the other night."
"Good dear, all that will be possible if you do as I tell you from now on. This will be our little secret, for the time being at least", She said. "But we will need to get you some new clothes. Well go shopping together next weekend."
On the following Saturday we went shopping together in a huge department store a few miles away. We went in into the area where womens clothes were sold and Mum talked to me quietly about the sort of clothes we might buy on this first outing given that I was just starting out on my new life. Eventually She decided I should have a lovely pink bra and panty set and a lovely white and blue cotton dress. She also bought some makeup that I could use and finally a pair of clip on gold earrings and a gold necklace. Mum knew what size clothes would fit me so there was no need for a shop assistant, and all of the purchases were completed without anyone possibly knowing that what Mum had bought was really for me.
When we got home, Mum told me to have a bath while She laid my new clothes out on my bed.
"I will wait for you downstairs darling. Get dressed in your new clothes when you have finished your bath and come down to see me."
Until now, Mum had always been there to help me get dressed in my baby clothes, but I suppose She thought it was time I started to learn to do some things for myself. It took me some time to adjust and fit the bra because I had never worn one before. My new beautiful pink panties slid easily up my legs and the feel of them against my cock was delicious. The blue dress also fitted me perfectly and Mum had left out a pair of white socks with frilly tops that I put on as well. Unfortunately I didnt have any girls shoes to wear.
i walked downstairs very slowly, somewhat embarrassed, but also enjoying the feel of these new clothes against my skin and especially the movement of the dress against my bare legs.
Mum heard me coming and She walked to the bottom of the stairs and watched me come down the last few steps. When I got to the bottom, She took me by the hand and led me into the lounge room without saying a word. She sat down and then motioned for me to stand in front of Her with my hands clasped in front of me.
"My oh my, how wonderful my little Sissy looks", She said before asking me to turn around so She could see me from all angles.
"We obviously need to get you some more clothes as well as some shoes in the near future, but you are starting to look like a lovely little girl Sissy arent you?"
"i suppose so Mummy", I said with my head bowed.
Over the next few weeks I spent quite a bit of time on the weekends dressed as either a baby or a little girl. Mum bought me a pair of black low-heeled shoes and another bra and panty set, but She said it was too soon for me to wear stockings and high heels. She would allow me to wear those things only when I had really proved to Her that I was happy to continue learning to be a girl for a long time to come.
My worst moment occurred when Mum had gone out with Elizabeth again for lunch and I was dressed in my baby clothes and confined to my room with the door sealed in the usual manner. I normally had to wet my nappy during these times but, until now, had not needed to do any more than that. On this day, however, I had to make a choice of disobeying my Mother or soiling my nappies. Eventually, I decided it was important to obey my Mothers rules so I pooed my nappies after about two hours alone. Mum did not get home until late and so I had to remain in my wet and soiled nappies for about three hours.
"Did my baby girl poo Her nappies?" She said as She entered my room after undoing the seal on the door.
"Yes Mummy, im sorry but I couldnt wait to go any longer, and You told me I could not leave the room."
To my surprise, Mum was very pleased with me. It seems I had done the right thing.
During this period I started to do virtually all the housework even if Mum was home. One evening when I was washing the dishes Mum came in and handed me a very long apron that was clearly designed for a girl. She told me to put my arms through and then She tied it behind my neck and around my waist. I wore it from then on whenever I was doing my housework chores.
Mummy was very good to me but She started to become quite strict about my behaviour and my attitude to Her when I was at home and dressed as a girl. It became very clear that I needed to be much more submissive if She was to continue to allow me to dress as a girl when I was home and buy me new clothes and accessories.
"Come on Sissy, suck on my nipple very gently now and look after Your Mistress." I clung to Her and my pink coloured mouth surrounded Her wonderful nipple as I sucked and licked while at the same time rubbing my fingers over Her moist pussy. I loved to do this for Her and the pleasure it gave to both of us was enormous.
"You will be good for your Mistress wont you Sissy", She said.
"Yes Mistress", I replied.
It seemed so natural to call Her Mistress. She was clearly controlling the direction of my life even though I had previously agreed to go down this path.
When I turned 15 my Mistress arranged for us to go away on holidays together for a month. She had rented a house in a remote location a few hours away by car. During this time I was dressed as a girl all day every day. Mistress spent a lot of time with me teaching me how to walk and behave like a girl and as a reward for my efforts She bought me a very pretty one-piece bathing suit. There was a pool at the house and for the first time I went outside dressed as a girl, even if I was still not all that convincing. We swam together and I rubbed sun cream all over Her, and we kissed and cuddled near the pool in the warm sun. I have never forgotten this holiday, because it really meant something to me to be with my Mistress as a full time girl.
i suppose that during this period the hardest thing for me to learn was that Mistress was to be in control of all of my sexual activity. It was made clear to me early on that I was not to masturbate without permission, but this was almost impossible. I regularly masturbated while I was in my bed in my wet nappies, and although I am sure my Mistress knew I was doing this She did not take any severe action to prevent this activity for a number of months. The final straw was when She walked into my room unexpectedly one morning and could see that I was stroking my cock. For the first time since all of this began She became extremely angry. She said I had breached Her trust and that I would pay for my error. She then left the room and nothing more was said until I was sitting at Her feet on the next Friday night.
i asked Her if I could sleep with Her that night and She said yes but there would be new controls placed upon me from Saturday morning. If I agreed to cooperate with Her we would spend the night together, otherwise I would have to sleep on my own all the time from now on. Of course I agreed. I was too far committed to my relationship with my Mistress to say otherwise.
Our Friday night together was fantastic and I thought that maybe I would be forgiven. How wrong I was.
The next morning She dressed me in my little girls clothes and then told me to wait for Her in the spare room next to my bedroom. I was there for about an hour before She came back in.
"On your knees quickly Sissy", She said. I did as I was told while staring at Her. I couldnt believe this was my Mother. She was encased in black leather and had on very high heel black leather boots. Her beautiful hair was tied in a ponytail sitting high on Her head and in Her hand She carried a small whip like those used by jockeys.
Without saying another word She reached down and pulled down my panties and pushed my head to the floor. My bottom was now completely exposed. She locked my head between Her legs and the smell of Her leather boots was almost overpowering. And then it began. She used the whip on me until I started to cry and begged Her to stop, but She ignored me and continued for at least another 10 minutes. At the end I was a blubbering mess and a pool of tears had formed on the wooden floor beneath me.
Then, again without a word, She left the room only to come back a few minutes later with a collar and chain I was to wear for the rest of the weekend. She locked the steel collar around my neck, attached the chain and made me crawl into my bedroom. She removed my clothes and put me in a clean nappy and plastic pants and nightie and then put me back into bed. The chain was locked on to the bed frame. Finally She used another pair of steel cuffs to lock my hands together and then attach them to a ring on the collar.
"You will learn Sissy that being disobedient means severe punishment from now on. Until now I have been very lenient with you because I believe that you have been doing your best. However, the probation period is over and you will learn, I hope, to obey me at all times."
i was locked in my bed that way for the entire weekend, with my Mistress only coming to see me to change my nappies or give me a drink and some food.
On the next weekend my punishment for my earlier misdemeanour was extended. After being dressed as a baby girl for some hours, and with a wet nappy, my Mistress made me lie on my back before She undid my nappy and began to stroke my cock. She was dressed in Her leather outfit again and so I came in great spurts all over my stomach. Mistress then got a small spoon from the kitchen and scooped it up.
"Here Sissy, drink this down and do it quickly or I will have to whip you again as I did last week."
i did as I was told without hesitation, and being forced to eat my own cum became a regular part of my training from that time on, as did a regular spanking or whipping. I only had myself to blame.
Chapter 6 Life After School
By the time I turned 16 my life was very dramatically different from two years previously. I was still a boy away from home and, although I did not have many friends, I did at least have some activities away from my home duties.
But when I was at home I was always expected to dress and behave as a little girl. my Mistress was very strict but also very loving and my relationship with Her was strong. I was still regularly punished, and on occasions the punishment was very severe when I didnt do things exactly as they were supposed to be done, but I began to accept these punishments as part of my new life.
i was now also chained to my bed each night, and I learnt to sleep with my hands cuffed and locked to my steel collar. Mistress said that this would be necessary for some time to come because of my breach of Her trust many months ago.
Soon after turning 16 there were a few momentous events in my life. Firstly, I left school. I was a poor student and I agreed with my Mistress that it would be better if I started to earn some money. As it happened Her friend Elizabeth offered me a job three days a week helping to deliver goods to and from Her salon where She also ran a mail order business for beauty products. I couldnt drive but I assisted another woman who worked there.
Then, a few weeks later, Mistress told me we were shifting to a town a couple of hours away by car. She had come into quite a bit of money from an inheritance from her Mother who died a few months ago. We rarely saw Her as She lived on the other side of the country and I think relationships with my Mistress were strained anyhow. So within a few weeks we had shifted into a new house and Mistress had also purchased a beauty salon of Her own near where we lived. The house was enormous with two living wings and I thought it was ridiculous to buy something so large. That was until I found out that Elizabeth and Her daughter Karen were to move in with us. I couldnt believe this when Mistress told me. I hated Karen because She had always gone out of Her way to be nasty to me, but whats more, my secret relationship with my Mistress looked like it had come to an end.
We talked about the situation one Friday night about a week before the others were to move in, and Mistress explained that, yes, it would not be possible to continue our relationship in secret. Elizabeth and Karen would have to be told, and She was willing to do that if I wanted to continue dressing as a little girl much of the time. She assured me that both of them would not share our secret with others. I was in turmoil, because I wanted desperately to continue, but I was also petrified about someone other than my Mistress knowing my secrets. In the end I agreed and looking back now I really had no choice. My relationship with my Mistress was the dominant factor in my life and I could not possibly live without it continuing.
They moved in the next week by which time Mistress had already told then of my secrets and desire to dress and behave as a girl. My Mistress had already told me that I was to refer to them as Mistress Elizabeth and Mistress Karen, even though Mistress Karen was younger than me, if I wanted them to accept my behaviour.
Things went well for a few weeks. I continued to wear my lovely girly apron when doing the housework and I was able to dress as a girl around the house on most weekends. Mistress still kept me in little girls clothes and, because I was still growing, She occasionally took me out to buy me a new dress or a pair of shoes. She still used very little makeup and I wore socks rather than stockings. I longed to wear more exotic womens clothes but it did not look as though I would be allowed to in the near future at least.
At night I was still restrained in bed and wore nappies and a nightie. I had a new bed with a metal frame and a number of anchor points that could be used to attach further restraints if Mistress thought that was ever necessary. There was also an anchor point on each wall and one in the ceiling. There was also a very small metal locking cage in one corner, but She told me it would only be used if I had been really naughty.
i now worked at Mistresss beauty salon doing the same sort of work that I did at the salon Mistress Elizabeth used to run. Mistress Elizabeth was now working at this salon also so I saw a lot of Her as well as my Mistress. I still had plenty of time off to do the housework which was more demanding than ever because I now had a much bigger house to clean, and more clothes to wash and iron. It was clear to me that I was to do everything, even having to clean up Mistress Karens room and make Her bed each morning.
Having to do these things for someone I did not like eventually led me into trouble. I had made Her bed one Saturday morning and was still picking up Her clothes and putting them away when She came back into Her room to get dressed for the day.
"My goodness, you are slow Sissy", She said. "You will need to improve your performance or I will make sure that you are punished by your Mistress for not doing your work properly."
i took real exception to this. I worked hard but nothing I did seemed to satisfy Her and so told Her that She was a little bitch and She could clean Her own room in future. I knew as soon as I said it I was in real trouble but it was too late to take it back. So I left and went into my bedroom and shut the door.
A short time later my Mistress came in with a stern look on Her face.
"Get undressed now Sissy, take everything off and stand in the middle of the room."
i did as I was told but I also tried to explain what had happened so Mistress would see that it was not all my fault. She took no notice of my pleadings and simply locked my collar around my neck and attached it with a chain to the ceiling anchor point. The chain was very short and I had very little room to move. The beating that followed was the worst I had ever experienced.
"You must learn to treat all of your Mistresses with respect Sissy, as well as give them total obedience. I thought that you were learning these things but it appears there is a long way to go. As you know, Mistress Elizabeth and I will be away all of next week, so Mistress Karen will need to look after you. I am sure that you can look forward to a very difficult week."
My Mistress was right. The next week was the most difficult of my life. Mistress Karen beat me hard and often and then locked me in my little cage for hours on end. She really seemed to enjoy punishing me and I couldnt help but think that She had deliberately provoked me knowing that Mistress Helen and Mistress Elizabeth would be away for a week. I was not allowed to dress at all except She made me wear my nappies and plastic panties when I was in the cage and when I was locked into bed for the night.
The week finally ended and life returned to something like normal although it was at least two weeks before the bruising on my bottom disappeared. And then Mistress Karen left to go to college to study fashion design. She came home infrequently over the next year and I avoided Her as much as it was possible when She was home.
My life with my Mistress eventually returned to some sort of normality. I worked hard to recover my position but I was still not allowed to sleep in my Mistresss bed. This privilege had stopped after I had abused Mistress Karen. This left me incredibly sexually frustrated and even though I was not allowed to masturbate I couldnt help myself. One night I was able to relieve myself by lying on my stomach in bed and simply rubbing my fully erect cock into my soaking wet nappies. It was bliss and I did this for a few nights before the inevitable happened and I was caught when Mistress inspected my nappies on removal one morning.
"I see you have been masturbating without permission Sissy. You should know better and I will soon put a stop to that sort of behaviour."
Mistress instituted new arrangements to secure me when I was in bed. A leather harness was placed around my waist with belts around the top of each thigh and straps running from the belt around my waist to the thigh belts. Now when I was put to bed I also was forced to lie on my back all night when straps from this harness were connected to the side rails of the bed preventing me from turning over. The final humiliation was the leather hood that Mistress also now locked on me every night. It had only very small holes for my nostrils and a small opening for my mouth but no holes for my eyes. Mistress told me that I would be kept this way when I was in my bed from now on. I would get erect every night but there was no way I could relieve myself and Mistress knew it.
i continued to work three days each week, but Mistress told me that my pay had to be put in a joint bank account where both of our signatures would be required to make a withdrawal. I was heading towards 17 years of age and I owned nothing and my Mistress effectively controlled the money I was earning.
Finally, after about six months I was allowed back in my Mistresss bed. As I suckled at Her breast Mistress stroked me to orgasm and, as in the past, collected my cum on Her fingers and fed it into my mouth. I licked her fingers tenderly and thanked Her for allowing me to cum again.
"Be a good Sissy for me and anything is possible darling", She said. "I think it is probably also time that Mistress Elizabeth looked after you occasionally at night. Would you like that my darling?"
"Yes I would Mistress if that is what you would like me to do."
The year ended better than it started and things were looking up until I learnt that Mistress Karen was coming home for a few weeks.
Chapter 7 Mistress Karen
Mistress Karen was to come home for two weeks on a Friday evening. After the two weeks She was to go back to college for three months to complete Her course, and then, as far as I knew, She would be home again for good after that time. Her intention was to open a fashion shop and operate it in conjunction with the beauty salon owned by my Mistress.
That She was coming home was difficult enough for me to accept, but then Mistress Helen told me that She and Mistress Elizabeth would use the opportunity to go away for a couple of weeks on holiday, and Mistress Karen had volunteered to look after me during that time.
i was already in bed and restrained in the usual way when She arrived home on the Friday evening. My usual bedtime was 8.00pm because I could normally complete all my daily housework duties by then, although sometimes, if I had been very good, I was allowed to stay up until 9.00pm on Saturday nights.
i had probably been in bed for about an hour when I became aware that Mistress Helen and someone else, who I assumed was Mistress Karen, had come into my bedroom. The leather hood, that I was now required to wear at all times while in my own bed, made it impossible to see but it also made it difficult to hear things unless the sounds were very close.
"Mistress Karen is here to say hello Sissy. I will leave you alone together so Mistress Karen can tell you Her expectations of the next fortnight", said Mistress Helen.
After Mistress Helen left the room, Mistress Karen sat on the edge of the bed and as She did so I flinched. My memories of our last encounter were still very strong and, frankly, I was frightened of what might happen to me over the next two weeks.
"Lie still Sissy or I will give you a spanking right now."
i lay as quietly as possible but it was difficult because in my anxiety I was gasping for air.
Mistress Karen said nothing for what seemed like ages but was probably only a couple of minutes.
"you and I are going to have a good time over the next two weeks Sissy as long as you show me the respect I deserve as a Mistress and you are absolutely obedient. I will be very hard on you if you do not meet these standards but I believe that you will do your best for me. Is that right Sissy?"
i guess I had no choice but to agree if I wanted to continue to behave as a Sissy when I was home. I could always leave home and start a new life elsewhere but the reality is I didnt want to do that. It was just that Mistress Karen really scared me.
"i will do my best for you Mistress", I said after a few seconds.
"Good girl Sissy, I am pleased with your attitude towards me. I think we will have a very interesting time together."
As She said this, I felt Her hand move under the sheet and then inside my nappies. She grasped my cock as She bent over me and kissed me lightly on my lips although that was not easy because of the leather hood. Unfortunately my instinctive reaction was to draw my legs up towards my chest to try and protect myself. For my mistake I received five severe slaps on each thigh.
"im sorry Mistress, it was not deliberate", I said to try and minimise the damage.
"That may be the case dear, but it was inexcusable and I intend to see that it cannot happen again."
She left the room briefly and came back soon after with a set of cuffs linked by a short length of chain to go around my ankles and another short length of chain to attach to the anchor point at the end of the bed. After She put them on me I could barely move at all once I was in bed and there was no way I could pull my legs up as I had done before.
"I talked to Mistress Helen about this issue Sissy, and She agrees with me that you need to be more tightly restrained when you are in bed. Expect the wearing of ankle cuffs to become a permanent feature of your life when you are in bed from now on."
Then Mistress Karen really surprised me by once again putting Her hand inside my nappies while kissing me on the lips. I could smell her perfume and feel Her power over me growing as She stroked my cock. I became erect very quickly and then reached orgasm as She licked my lips with Her tongue.
"My my, isnt Sissy growing up. Her clitty is much bigger than the last time I saw it and it obviously is capable of producing a lot of cum. Here, can you smell it Sissy?"
With that She inserted a cum-soaked finger in my mouth and I licked it clean for Her. I must admit that being close to Her in this way was very exciting for me, and some of the bad thoughts associated with our last time together began to disappear.
After a while She pulled my nappies and plastic panties back into place before kissing me goodnight and telling me She would see me in the morning.
"Goodnight Mistress", I said, wondering what would happen to me tomorrow.
She came back into my room the next morning with a babys bottle full of my usual breakfast juice. It was sweet and I needed it desperately after having a very uncomfortable night in my new restrained position. She guided the teat through the space in my leather hood and into my mouth as She lifted my head slightly with Her hand.
"Here we are baby. Be a good girl and drink this all up for me."
i drank eagerly and soon felt better as the warm fluid flowed into me and I could feel Mistress Karen really close to me. I started to feel cosy and warm and comfortable except I had been in bed so long I really needed to pee. I think I started to squirm so much that Mistress finally asked me what was wrong. I told Her that I needed to go to the toilet and She said She expected me to wet my nappies before I got out of bed anyway. I soon flooded my nappies and then I lay back on the bed as Mistress first unlocked and then unlaced my hood before slipping it off me.
Mistress was still sitting on the edge of the bed and She was stunningly beautiful. I couldnt believe that this was the same Mistress I had last seen so long ago. Although She was a little younger than me She looked very grown up, with a full and shapely figure that was contained in a full-length tight leather dress with long sleeves. It had a v-neck and I could see the swell of Her breasts. She wore a studded leather collar and striking makeup. She was the most beautiful woman I had ever seen.
"Hello Sissy, its good to see you again. Are you pleased to see me too?"
What could I say? Despite my earlier anxiety about seeing Her again, everything had been OK so far.
"Yes Mistress, I am pleased to see you again."
She kissed me on the lips and then released me from my other restraints, before telling me to get up and have a shower. When I was finished I was to wait for Her in my bedroom but not get dressed in my usual little girl clothes. She had some other clothes that She thought I should wear for the day.
I showered and waited for Her in my room for a while before She came in and put a locking leather collar on me and with a leash led me into the spare bedroom.
"Your Mistress and I have agreed that it is time we started to get you used to wearing some new clothes Sissy. So I have bought you two new dresses and some new underwear and shoes that you will wear all day today and tomorrow. On Monday you will be back to wearing your usual clothes because I know that you will have a lot of housework to do."
Mistress first brought out a small pink lacy bag that She tied on me to hold my balls. Next came a pair of pink and white long-legged panties that had a small opening in the front through which She pushed my cock and balls to leave them dangling free outside the panties. The panty legs came down to mid thigh and there were pink ribbons around each leg that She tied to make sure the legs of the panties could not ride up. The waist on the panties was fairly high and I became erect almost as soon as She had put me in them.
A long-line lacy pink and white bra was next. It was beautiful and it left only a small gap to the top of my panties. She placed a garter on my left thigh and then made me put on long white socks that also had little pink ribbons at the top that were tied to keep them above my calves.
Then a beautiful pair of pink shoes with what seemed to be a two-inch heel. They had straps to go around my ankles and they were the highest heels I had been allowed to wear so far in the time I had been dressing as a girl. I already felt very sexy and excited but there was more to come.
Mistress slid a little gold ring over my cock and then, using a tiny Allen key, reduced the diameter of the ring so that it locked into place behind the head of my cock. It had a short fine chain attached to it and at the end of the chain was a bell that tinkled every time I moved.
"Sit down Sissy while I brush your hair."
i sat down on the chair in front of the dressing table and Mistress Karen spent about ten minutes brushing my hair before using pins and ribbons to give me a beautiful little girl look. my hair was still reasonably short but it was long enough for Mistress to be very pleased with the result.
She put on a little makeup and used a really glossy pink lipstick that set off my hair and really looked pretty with the underwear I had on. She also dabbed a little perfume behind each ear and on the inside of each wrist.
Finally, She told me to stand up and from the wardrobe She got the most gorgeous dress I had seen in my life. It was white and lacy and frilly with pink ribbons around the hem, each cuff the waist and the neckline. It was full length and it flared beautifully to the floor because of the many layers of lace that had been used.
"I see that you like your new dress Sissy. I thought you would but before I put it on you there is one last thing to do."
She opened a drawer to reveal two breast forms that She slid into the cups of my lovely lacy bra.
"They are only small at this stage Sissy because I still want you to be a little girl, but they will give you the beginning of a nice figure for a young girl. Perhaps you will have larger breasts when you grow up."
She made me step into the dress and then zipped it up at the back. She was right because my new breasts could just be made out underneath my dress. I was in heaven. I love dressing as a little girl and had done so for some time, but what Mistress had done to me made me feel more like a girl than ever before. She made we walk around the room and the feel of the dress on my legs made me feel very sexy. As I walked the little bell attached to my cock tinkled all the time and the sound seemed to be telling the world that here was a beautiful and new little girl.
"May I have permission to speak Mistress", I said.
"Yes Sissy, what is it you want to say?"
"Mistress, thank you for being so kind to me. I love this dress and the other things you have given me."
Mistress was pleased with my response and She kissed me on the lips lightly before picking up the leash attached to my collar and leading me downstairs.
i spent the rest of the day dressed this way. I made Mistress some lunch and made sure that I looked after Her in every possible way. In turn She gave me a lot of instructions about how to walk and sit and behave more like a little girl. I was learning all the time and I tried really hard to please Her, not because I was afraid of Her but because I really wanted to look after Her and make Her happy.
That night I was back in bed at 9.00pm and restrained as usual. I received my regular punishment on most Sunday mornings, so before getting dressed the next day, Mistress gave me quite a severe spanking just as Mistress Helen would have done if She had been home. I was then dressed in the second new dress Mistress Karen had bought for me. It was similar to the first, but the trimming was blue instead of pink. I loved it too.
On Sunday night before I went to bed, and while I was still fully dressed, Mistress made me kneel at Her feet. She told me to hold up my dress and while She looked directly into my eyes She stroked my cock. The little bell still attached to the cock ring tinkled furiously as I came over and over into Her hand.
"Thats for being such a good girl for the last two days Sissy. You have been very sweet and you really do look very pretty. It is a pity that only I can see you. Perhaps one day we will correct that. Now off to bed girl. I will be up in a few minutes to put your restraints on."
i nearly ran up the stairs, and that night I had wonderful dreams of my time with Mistress Karen.
i worked hard around the house all week and I did not get to dress in my new clothes again until the next weekend. The following Friday, Mistress Helen and Mistress Elizabeth returned home and, before I knew it, Mistress Karen had left to go back to finish college.
Chapter 8 A New Owner?
i was continually getting into trouble with both Mistress Helen and Mistress Elizabeth. Nothing I did was right. My housework was sloppy, I ironed creases in the wrong places and I had not cleaned the showers as well as I should have. Spankings, apart from my regular Sunday punishment, became more frequent and Mistress Helen in particular became really severe on me.
For the first time in my life She used a whip other than the riding whip She had used some time ago to try and bring me into line. It left marks on my backside and legs that took nearly a month to go away. I think Mistress Helen was a little upset that it had come to this and She tried to get me to talk about what had gone wrong. Initially, I refused which just made things worse.
Then one morning after I was released from my bed, She sat me down again and insisted that I tell Her why I was so distracted and performing so badly as their slave around the house.
i eventually burst into tears, and as much as I didnt want too, told Her that I missed being with Mistress Karen. I thought this would make Mistress Helen very angry because I was, after all, her slave. But She smiled and said She thought it must have been something like that. She also said that She was willing to consider transferring ownership of me to Mistress Karen if Mistress Karen would agree, and She would talk to her soon. In our discussion it became clear to me that Mistress Helen and Mistress Elizabeth really loved each other and would like the opportunity to spend more time together. Their holidays away together suddenly made sense to me.
i think Mistress Elizabeth felt really sorry for me in some ways although She never said anything. One day when She was looking after me at home, She told me to sit down on the floor next to Her and She then pulled my head close to Her thighs and told me that I was really a good little girl at heart and that She could tell right from the beginning that I really liked Mistress Karen.
"You are such a good little girl, that I think you should get really close to Her by worshipping where She came into the world."
i was lost initially. What was she talking about? But She then stood up in front of me and lifted Her leather miniskirt a little higher on Her hips. She had on a leather g-string and She told me to take it off Her. I did as I was told immediately to avoid any punishment, and then Mistress Elizabeth stepped towards me and pushed Her pussy close to my face.
"I dont think our little girl has had the privilege of worshipping the pussies of her Mistresses yet has she darling Sissy? Well, I want you to worship mine now and you will do it properly or I will whip you like Mistress Helen whipped you last week."
i moved my face to Her pussy and started to use my tongue to lick Her.
"I want your tongue inside me girl. Quickly."
i did as I was told and I pushed hard inside Her and tasted Her beautiful female juices. I was hard instantly and I began to lick and lap and suck and kiss Her pussy with great passion. She squirmed on my face and pushed my head deeper into Her crotch by putting both hands behind my head.
Eventually She came again and again with my tongue still deep inside Her. It was beautiful to be this close to her and to know that this is where Mistress Karen came into the world.
"Stroke yourself Sissy."
i pulled down my panties and stroked until I came in spurts all over the floor between Her legs as She came one final time.
Then, without a word, She put Her g-string back on, pulled down Her miniskirt and pushed my head to the floor.
"Clean this up with your tongue Sissy. Thats a good girl."
i licked my own cum from the floor feeling my usual mixture of sexual excitement and humiliation. My Mistresses had certainly changed my behaviour dramatically since that first day at the age of 14.
When Mistress Helen came home I was told to come and sit on the floor between them while they talked about the events of the last couple of days.
Mistress Elizabeth described to my Mistress how I had performed at my first attempt at pussy worship. I blushed when She described my attention to Her pussy in some detail, and She said that I showed a great deal of promise. It seemed that pussy worship was something I would be working on during the next stage of my sissification.
Mistress Helen then told me that She had spoken to Mistress Karen who would be delighted to take over ownership of me, but there were some conditions that I needed to consider very carefully before committing myself.
First, Mistress Karen was not really interested in a part time sissy. I would have to accept that I would eventually be treated as a sissy full time, and that this would mean I would have to be seen and accepted as a sissy by people other than my present three Mistresses. Secondly, I would have to work more to ensure that I contributed to my own keep, especially as I would need an extensive new wardrobe. Mistress would decide where and when I worked. Finally, if Mistress Karen came to own me She would want me to consider hormone therapy because She believed a real sissy needed real breasts. She did say that any decision on this matter would be up to me and it was something we could discuss at leisure sometime in the future. I had thought about this possibility before and I was apprehensive. I really quite liked being a boy who dressed and behaved as a girl and it was something I would not agree to lightly.
"If these conditions are likely to be acceptable to you I will tell Mistress Karen. However, Mistress doesnt want to rush things and thinks that it would be good for you to think about this for a while. I agreed with Her that a period in which you could contemplate your decision was essential, and I have therefore arranged for you to visit a friend of mine for a month beginning next week. Mistress Helga has been a friend for a long time and She will provide you with the right environment in which to make a decision. Do you agree to do this Sissy?"
"Yes Mistress, I do."
And that was it. Mistress would take me to Mistress Helgas place next Saturday.
Chapter 9 Decision Time
We arrived home from Mistress Helgas about lunchtime on Saturday, and on the way home Mistress Helen told me that Mistress Karen would be home that evening to hear of my decision.
If I was going to agree to Her conditions then I would need to present myself to Her in accordance with the instructions that Mistress Karen had typed out and given to Mistress Helen to pass on to me.
"You are to spend the rest of the day until 8.00pm in your room Sissy. If you are going to agree to be Mistress Karens slave girl, then follow these instructions precisely. You will need these things that Mistress Helga gave me, but it is quite possible that you will need some assistance to prepare. Mistress Elizabeth and I will check with you in an hour to see if you want us to help."
My mind was made up before I left Mistress Helgas. I had no choice but to agree to the conditions and become Mistress Karens slave girl. My time with Her a few months ago was still fresh in my mind and I had a deep-seated need to be submissive to Her and be Her loving Sissy and slave girl.
When Mistress Helen came up an hour later I got onto my knees and waited for Her to speak to me. I then asked Her if She and Mistress Elizabeth would help to prepare me. She said yes with a wonderful smile on Her face.
"i love you Mummy, sorry, Mistress Helen", I said.
"I love you too my darling Sissy."
i found that Mistress Helga had packed my chastity belt and the locking butt plug, both of which my instructions said I was to wear this evening. Mistress Karen said I was to wear my pink and white dress, but She had provided me with a new panty and bra set and a suspender belt and for the first time I was going to be allowed to wear stockings. The final joy was a brand new pair of white ankle boots with 3" heels. They were beautiful and I could hardly wait to put them on.
"Before we start getting you ready for your transfer to Mistress Karen, there are some things that I need to tell you Sissy."
i started to worry. Were the conditions of my transfer to become more onerous? That was not to be the case, but the story Mistress Helen told me did explain a lot of things that I had never understood before. It seems that Mummy and Mistress Elizabeth had become close friends after my father left home. After the divorce they discovered that they shared an interest in female domination and eventually they both joined a group of women across the country that pursued this interest with great purpose. My Mother was very concerned that I might grow up to be like my father, but She soon saw that would not be the case and in fact She saw a submissive side to me that would make me a promising candidate. So, at an early age Mistress Helen and Mistress Elizabeth agreed they would see if I could be feminised and eventually put into a form of slavery to serve women in the group. They were both determined, however, to lead me down the path, but not force me. When I was 12 years old they agreed to begin the program in a very subtle way but it was when I was 14 that the trigger to start my conversion in earnest arose because of my distress at school. Mistress Karen knew of these plans because Her mother, Mistress Elizabeth, was keen for Her to become a Mistress and have control over Her own life rather than have some horrible man control Her. I listened carefully as I remained on my knees before Her. It was also clear that the final stage, that I was now entering, would not have happened if I had grown too much more. But at 511" Mistress said I would still be able to present myself as a lovely girl.
"I would not have done this if it was obvious that you were not interested but, thankfully, you were. That is how we are where we are today Sissy. Nothing you can say now can alter what will happen later today, but is there anything you wish to say dear."
Perhaps Mistress expected me to be upset, but the reality was that I was increasingly accepting of my new role in life and it was true that I had effectively made the decisions myself that had led me to today.
"Mistress, I just want to say thankyou for telling me and thankyou for looking after me so well. I love You and I will always love You. I am very happy that You did what you did."
She smiled and then kissed me before telling me to undress so She could help me to prepare.
My butt plug was locked in place first followed by my chastity belt. Mistress Helen seemed to have no trouble in putting it on me and it seemed like She had done something similar before. Next came a new long line bra that was really quite tight around my chest. A pair of white fishnet stockings followed a new pair of long legged panties and the suspender belt. This was my first time in stockings and I could feel my cock swell inside the tube of the chastity belt. I groaned with pleasure and Mistress looked at me with delight.
"I love to see my Sissy enjoying herself darling," She said as She stroked my hair.
The same small breast forms were put into my bra and She said that in the near future I would be getting a pair that could be glued to my chest for long periods. The ankle boots were next and I found that they had a strap around my ankle with a little lock to ensure that I could not remove them by myself. Mistress then did my hair beautifully using hairspray to hold it in place, and applied some new makeup that gave prominence to my eyes with very long false eyelashes. My nails had extensions glued on them and this time they were painted a pink colour to match my dress. I had only ever worn pearl coloured nail polish before with my little girls clothes, and my nails were also kept quite short until now. Perfume on my wrists, behind my ears and near the top of each thigh made me feel sweet and delicious. My cock remained swollen in its restraint.
"Mistress Karen wants to make sure you walk like a girl tonight darling. It is an area where you need to do a lot more work and so She has told me to put this long and narrow petticoat on you to restrict your movement."
Next came my dress and again I shuddered with pleasure as I felt it around my legs and the tightness across my breasts as Mistress pulled the zip up my back.
"Nearly there dear. These clip-on earrings and this gold choker will set you off very nicely. Now, have a look at yourself in the mirror."
What I saw was more than passable. I would never be the most beautiful girl in the world, but there is no doubt that with some more work on my deportment and grooming I would be able to pass outside.
Mistress took me by the hand and led me around the room so I could find my balance in the new boots. It was difficult at first, but being hobbled by the petticoat made me take small steps and that seemed to help.
At last I was ready and all that was required was the order from Mistress Karen to come down to greet Her.
The order came after about an hour during which time I practiced walking and the curtsey that I was told to use in my greeting to Mistress Karen. Mistress Karen led me downstairs now
with a narrow gold metal collar locked above my gold choker. The leash was also metal and gold in colour.
i entered the room and curtseyed as I had been told and then I lifted my dress and knelt in front of Mistress Karen. I became aware there were others in the room and I looked around to see Mistress Helga and Mistress Serena as well as Mistress Helen and Mistress Elizabeth. They were all stunningly dressed in provocative leather outfits and they all wore long boots with very high heels.
"Concentrate on me Sissy. Thats why you are here. You just earned yourself an extra punishment session in the next week. What do you say to that?
"Thank you Mistress."
"Good girl. Now I understand you have accepted my conditions, so you need to sign this contract to transfer ownership of your life to me."
i signed a very large document without reading any of it, and then Mistress took my right hand and put a ring on me to signify Her ownership of me. It was a simple ceremony but I felt very glad I had committed myself to Her. I was then asked to serve everybody a drink and as I did so they each complimented me on how I looked. I was in heaven.
It also was explained to me that Mistress Helga and Mistress Serena would be moving in with us in the next week, and that renovations would construct a dungeon in the cellar for Mistress Helga to work from. Mistress Karen was to move into Mistress Helens room next to me and Mistress Helen and Mistress Elizabeth were to share a room in the other wing of the house. I was also told by my new Mistress that Mistress Serena would be in charge of the house and would be making sure that I did all my duties correctly.
After a couple of hours Mistress told me to go to bed. She also said that I had been such a good girl that Mistress Serena would spend the night with me. I went up to bed and put on my nappies, plastic panties and nightie. I had also learned to put on my leg restraints and my waist harness and then my collar, so I was already in bed and in bondage when Mistress Serena came in.
"As a special treat Sissy, your Mistress says I can leave your hood off for tonight and your hands free. That should ensure that you and I have a marvellous evening and I will also be with you all day tomorrow. Your Mistress is busy with some other things tomorrow and you will be in Her charge from Monday morning."
To my surprise Mistress then put a large fluffy nappy on and soft pink plastic panties under a transparent pink nightie. She slipped into bed next to me and gave me a big kiss and cuddle.
"How would Sissy like a drink to settle her down for the night sweetie?" She said, and without waiting for a reply fed Her right nipple into my mouth. I sucked as I had learnt at Mistress Helgas and Her sweet warm milk began to flow into my mouth. I was in heaven as She continued to feed me for the next 15 minutes or so.
"There, there does baby feel better"
i felt wonderful and I hugged and kissed Her before we lay in each others arms and went to sleep.
In the morning I was soaked through and so was Mistress Serena, but when we woke up She told me that I would be staying in bed for a while and She then took my hand and drew it down to Her nappy.
"Make me feel good Sissy, and then perhaps I will give you another drink."
i put my hand inside Her nappy and it was warm and wet , and I gently inserted my fingers into Her pussy. She squirmed with delight as I pushed deep inside Her and eventually She came over and over again before stripping off Her wet nappy and straddling my face.
"Mistress Elizabeth tells me that you are learning to eat pussy Sissy. I want you to practice on me."
i did as I was told and I licked and lapped Her pussy bringing Her to orgasm several more times. I was learning to love serving my Mistresses in this way.
Mistress then opened Her maternity bra and fed me again from each breast.
"I want my Sissy to poo her nappies while I am feeding Her", She said. It is very important that you realise that you are my helpless little baby for the rest of the day darling, so dirty your nappies for me as quickly as you can."
Again, I had no choice to do but as I was told, and I filled my nappies as Her milk continued to flow into my mouth.
i was to remain in my dirty nappies for nearly two hours as Mistress Serena lay next to me and talked to me about being a good baby and how much She and the other Mistresses loved seeing me learn to be a girl. She then let me up and I washed before She put me back in baby clothes and a baby harness and made me crawl downstairs into the lounge room. Mistress Karen was out, but Mistress Helen and Mistress Elizabeth were both there and I spent the afternoon with them dressed as a lovely little baby girl.
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