(Repost) Mother in Law made me a Sissy Maid by Sissy Karen

[Sissy Ballerina Boy]

Mother in Law made me a sissy maid - Part 3
1/14/2016 33 Comments
 
 The Fitting 
by Sissy Karen

?Part 1  Part 2       

I returned with Mother from the airport and as soon as we got in the house my next ordeal began. Mother ordered me to change into the floral pinafore and then marched me into the lounge room corner, nose to the wall and commanded me to put hands on head. I had failed to finish the ironing before church and now must suffer the consequence. The waiting in this position was so nerve wracking. There was nothing to distract my thoughts, all I could think about was the upcoming punishment. Last time she beat me so hard with the hairbrush I started to cry. Ever since then I had lost the privilege of wearing male clothing in the house and she started calling me Georgie. It was to stay this way until I could learn to take my punishment like a man and not cry. It seemed like hours but was probably only 10 or 15 minutes of nervous anticipation before I heard Mother walk into the room. I was determined not to cry this time.
 
“Right Georgie, over here and bend over the dining table.”
 
I turned around and there was Mother holding a cane! Last time my spanking was with the back of the hairbrush and that was enough to make me cry. My heart sank but I was determined not to cry so I could get out of these girls clothes. As I lay across the table she lifted my pinafore and dropped my panties exposing my bottom.
 
“What is this punishment for Georgie?”
 
I hated having to admit it like this.
 
“For failure to complete the ironing on time Mother.”
 
“And what else?”
 
I was in a tizz and didn’t know the answer. I hesitated, stammered a little and said very nervously,
 
“I don’t know Mother.”
 
And with that a fierce stroke came down right across my bum cheeks,
 
“Ahhhhhhhh” I screamed like a banshee.
 
“That might help you remember! So Georgie, what else are you being punished for?”
 
I hesitated again, my brain going a million miles an hour, but for the life of me I couldn’t recall what else I was supposed to get punished for. Another fierce stroke came down and again I squealed. The pain was intense and I could feel the beginnings of that terrible urge to cry. My eyes began to tear up.  I fought it with all my might. I think after crying for the first time in years the other day, my resistance had lowered. I was on the verge again and the punishment hadn’t started properly yet.
 
“I d.d.d.d don’t know Mother…was it for church?”
 
“No!”
 
Another stroke this time she got me at the top of my thighs and the pain was excruciating! I squealed like a banshee. The tears were really welling up now. I was
 
“I can do this all afternoon until you remember Georgie. Let me ask you again, What else am I going to punish you for?”
 
“Pppplease Mother, I really can’t remember, I am sorry…”
 
“Thwack!”
 
This one got me atop the thighs and absolutely killed, I cried out and that was it, I started crying again.
 
“Ahhhhhhhhh!”
 
“Oh Georgie! Crying already! You really are a sooky girl aren’t you? You will be in dresses for a long I time I fear! And your punishment proper has not even started! Let me ask one more time, Why else are you being punished Georgie?”
 
This was so agonisingly frustrating, I was wracking my brain, trying to remember what else I had been reprimanded for.
 
“Not accepting the grapefruit with gratitude Mother?”
 
“While that is true it is not the answer I was looking for.”
 
She took a big backswing and laid another stroke right over one of the previous strokes. It cut and cut hard. I yelped and started crying again. I felt so ashamed and broken.
 
“I have been more than generous giving you a chance to remember Georgie but it seems you cannot. Not remembering is a sign of disrespect Georgie, it shows you are not taking my teachings seriously enough doesn’t it Georgie.”
 
“Yes Mother….sorry Mother.” My voice was shaky.
 
“You are being punished for not just finishing the ironing on time but also for not doing a thorough enough job!”
 
I couldn’t believe it, surely this was one and the same offence!
 
“I think the answer to this little problem will be to have you sit a little detention, maybe then the message will sink in. Don’t you agree Georgie?”
 
“Yes Mother.”  I was in no state to disagree.
 
“You will write 100 lines : When doing the ironing I work promptly, efficiently and thoroughly. At all times being completely focussed on my task. Understood Georgie?”
 
“Yes Mother.”
 
“You will hand them to me at breakfast tomorrow morning and can start working on them after you have finished all your chores tonight.”
 
“Yes Mother.”
 
It was going to be a long night, followed by an early morning as the ironing was still waiting to be completed. Mother then continued with my official punishment for the offence. 24 searing strokes of the cane. I cried all the way through it. My bum was on fire afterwards and I felt utterly humbled and helpless afterwards. I knew I would have to lift my game under this new regime.
 
“Pants up Georgie, we must be getting to Mrs Grossman’s place for the measuring of your new uniform. Go wash your face and we will get going.”
 
I went to the bathroom and washed away my tears, feeling very sore and sorry for myself. The last thing I felt like was going to get fitted for my maids dress. The feeling of apprehension at the humiliation to follow was gnawing in my stomach. As I drove Mother to Mrs Grossman’s she continued to lecture me on how I had so much ground to make up before I reached an acceptable standard. My bum was on fire and I shifted around in the seat as I drove.
 
We soon arrived and Mrs Grossman greeted Mother enthusiastically giving her a big smile and welcoming us in. Her tone with me was very different and immediately her face scowled as she said in a commanding tone, “This way Georgie.”
 
We were led into her working room and Mrs Grossman offered Mother a cup of tea but did not ask me. She returned with the tea and biscuits for Mother and herself but nothing for me. There were 2 chairs only in the room and I dare not sit down. While the ladies were drinking their tea the conversation turned to my training. I started to blush red with embarrassment especially when Mother said “As long as he cries like a girl when he is being punished he will be dressing in his maids uniform when at home.”
 
“You a woman after my own heart!” exclaimed Mrs Grossman.
 
She opened a book of patterns from a book called “The working girl.” It looked quite old and showed Mother some of the maids dresses she thought may be appropriate. They discussed various uniforms until they found one that Mother approved of.
 
“I quite like this one as a working uniform, the apron needs to be starched when ironed and the pleats are a bit fiddly but it looks good. What do you think Eleanor.”
 
“Yes that looks perfect, she will learn to iron it perfectly won’t you Georgie?”
 
It was the first time I had been spoken to.
 
“Yes Mother.”
 
 Came my meek reply. I caught a glance of the picture with the pattern. It did look like a nightmare to iron. The lower half of the dress had 2 pleats on the front and 2 on the back. The sleeves were quite puffy and had many pleats as well. There was an apron that tied around the back. In the picture it was tied in a perfect bow, which looked hard to attain and a hat as well.
 
“It better be Georgie as there will be consequences if you do not present yourself perfectly for inspections.”
 
“Yes Mother.”  I was beginning to get worried.
 
Mrs Grossman nodded approvingly at Mothers comments then ordered me to strip to my
 panties and come step up onto a step in front of her.
 
I quickly obeyed. I felt so embarrassed standing there in my pink panties under the gaze of both matrons.
 
“Hands in the air girl.” barked Mrs Grossman.
 
I did as I was told and felt so embarrassed and vulnerable before her. She noticed the cane marks on my upper thigh, under my butt cheeks and ran her hand over them, reminding me of the agony.
 
“Look’s like someone’s been a naughty girl Georgie.”
 
“Yes Mrs Grossman.”
 
“And what did you do Georgie to deserve that?”
 
I looked at mother standing there with her arms crossed, a smirk on her face, I could swear she was enjoying my humiliation.
 
“I didn’t complete the ironing on time Mrs Grossman.”
 
“A good maid works hard and stays focussed Georgie.”
 
“Tell Mrs Grossman what else were you punished for Georgie.”
 
“I didn’t do a thorough enough job either Mrs Grossman.”
 
“Oh well Georgie, practice makes perfect. I always have plenty of ironing to do, maybe Eleanor might let you come over for some extra practice!”
 
Both the ladies laughed and I didn’t say anything. After a bit of a chuckle Mother said,
 
“What do you say to Mrs Grossman for her generous offer Georgie?”
 
“Thank you Mrs Grossman.”  That’s all I needed even more ironing! I hoped like hell that they were joking, I had enough on my plate already.
 
I had felt a little tingle of arousal as Mrs Grossman fondled my cut marks. She measured my arms, bust and waist first. When she did my inner thigh, I could feel my arousal get stronger. The back of her hand then rubbed against my panties right were my balls were and I couldn’t help it and became hard. There was no hiding it in the tight panties and Mrs Grossman screamed.”
 
“Ewww, she’s gone all hard.”
 
Mother looked and her face froze over in fury.

[Sissy Ballerina Boy]

“How dare you Georgie!” she screamed at me , walked over to me, grabbed a ruler off the table and started slapping at my bulge. Oh how it hurt, each slap hitting my willy or my balls, quickly causing it to subside.
 
“You are an utter disgrace Georgie, getting all lustful over Mrs Grossman who is simply doing her job. It is oafish, disrespectful and sexist. You are going to be published severely for this.”
 
Mrs Grossman was looking all upset and said,
 
“I am in shock Eleanor, I feel violated, getting all tumescent before me. I have the measurements, I think I may have to ask you both to leave, so I can compose myself.”
 
“Of course Heather, I am so sorry for what Georgie has put you through, you can rest assured that there will be a just punishment for this outrage and we will work out a way he can make it up to you. Once again accept my apologies.”
 
Mother barked at me “get dressed quickly Georgie!”
 
She put her arm around Mrs Grossman to comfort her as I got dressed than grabbed me by the earlobe and marched me out.
 
The drive home was hell. Mother wouldn’t stop berating me.
 
“You have shamed and humiliated me as well as yourself Georgie! So grossly displaying your carnal rage in front of Mrs Grossman! What will Deborah think when I tell her, that you are lusting over other women behind her back! It is a gross betrayal of my daughter and a breaking of your sacred marriage vows! Also it is outright sexual harassment Georgie! I win’t be surprised if Mrs Grossman call the police. You oafish brute! Just when I thought we may be getting somewhere with you. Believe me you are going to regret this!”
 
I couldn’t believe she was going to tell Deborah, I felt so ashamed of myself. Mother had me gripped in fear. I was marched into the house and told to stand in the corner with my hands on my head. I was made to wait what seemed like half an hour or more. I heard Mother enter the room from behind.
 
“Turn around, panties down, Pinafore up!”
 
I lifted my panties down and my frightened little willy was exposed.
 
“Put out your hand Georgie.”
 
Mother than started pouring Tobasco sauce all over my hand.
 
“Now rub that into your willy.”
 
I started to rub and at first it felt nothing, but moments later the heat began to build. Mother kept splashing more sauce on it.
 
“Rub it into the balls too Georgie!” Her voice was cold and angry.
 
“Yes Mother.”
 
Soon it was a burning agony, but she wouldn’t stop. The heat got stronger and stronger and I started sobbing, crouching over. This was hellfire! The heat was excruciating! Tears began to form and roll down my eyes.
 
“That’s it cry like the big girl you really are, you are a fraud as a man. Thinking you can lust over other woman. This is what happens to husbands who are unfaithful!”
 
The torture went on for what seemed like an hour and I was sent back to the corner. Mother returned again.
 
“C’mon out again Georgie and turn around.”
 
My shrivelled red willy was looking like a coc-ktail frankfurt.
 
Mother then started to peg clothes pegs on my willy and balls. Each time one clipped on it hurt like the blazes! But to make it worse she kept moving them around. The releasing of the peg hurt even more than the putting on for some reason. The one on the tip of my willy hurt the most and she began to flick it back and forth with her manicured fingernail. It pinched tighter and tighter as she flicked and eventually slipped off. The relief was massive but she just said,
 
“Oh no, I wasn’t finished, Lets put it back on.” She clipped the peg back on the tip of my willy and the agony was repeated over and over.
 
After that ordeal it was back in the corner again to once more contemplate my predicament and feel sorry for myself. It was another miserable humiliating wait in the corner with my hands on head and my willy aching. It was red as a beet, shrivelled and covered in pinch marks. Mother returned sometime later.
 
“Right Georgie, I just had a long chat with Deborah on the phone and to put it mildly she is utterly disgusted and disappointed in you! Her initial reaction was to file for divorce immediately for this gross act of infidelity. However I persuaded her that there may be one solution to your problem. You see in the early days of my marriage with Deborah’s father I walked into the garage and caught him masturbating over a Playboy magazine. I was rightly infuriated, disgusted and  angry with him for his sinful act of betrayal, just as Deborah is feeling about your sinful act. However a good friend of mine, Mabel White introduced me to the Tollboy chastity device.”
 
She was holding a box in her hands, about the size of a mobile phone box.
 
“Once I had Deborah’s Father locked up and under my control he became a dream husband. I was hoping I wouldn’t have to resort to this with you Georgie but after your performance today you leave me with no option. Luckily I kept his device and now it will be going on you. Hopefully this will do the trick to stem your awful lustful ways. Step over here.”
 
I stepped over and she proceeded to fit the device. My willy was still very sore and the fitting was made extra uncomfortable and when the sensitive spots rubbed on the device it reignited the pain. Once locked, Mother fitted the key on the chain she wore around her neck.
 
“I will be holding the key from now on Georgie. I spoke to Deborah who agrees even when she gets back it is best if I hold it, due to the experience I have in these matters. The only time, and I mean only time you may ask to have it removed is if you are going to be doing something like a doctors appointment where it may have to be shown or if you suspect it may be causing an injury. Otherwise any pleading will result in longer before it is allowed to be removed. If Deborah wants to use your willy, she will have to come to me first.”
 
Her mention of Deborah had me worried, it was awful not to be able to give her my side of the story. I wasn’t lusting after Mrs Grossman, it was just a physical reaction to being touched and I hadn’t had any sexual outlet for days. Thinking of Deborah though made me aroused but my first attempt at an erection was painful as the device crushed it. It was a feeling I was going to get very used to.
 
“OK Georgie, you can make me dinner, than wash up. Then an hour of ironing and an hour of scripture homework before bed. Oh I nearly forgot you detention is due in the morning as well. You can do that after you report to me with your Scripture homework. No dinner for you tonight. Chop Chop!”
 
With that I scurried off to the kitchen. My level of humiliation, misery and submission raised yet another notch.