Petticoated

Petticoated.

I knew I'd lost it the moment the car's wheel skidded into the curb. I knew that I had lost a lot more than the car, the first of the losses was the issue of my career, ten years of learning and effort, that was gone. The car belonged to my mother, and she could be mean, the loss of liberty she would impose wasn't much of an issue though; not when I knew I was going to be in hospital for a long time.

Mom had never been the suburban housewife type. She had ridden super bikes in races before I was born and never lost the love of speed she had. Her car was a Maclaren 570S, and she loved it. I knew she was going to go apeshit as I ran out of reflexes and talent, going around a corner very fast, with the river on the outside.

Even as the car screwed around in the air losing parts in slow motion while at the same being very fast, I knew this was going to be bad for me when I got out of hospital. I hit the water dimly aware that a lot was hurting and the windshield was ripped away as the car skipped like a stone. This meant the car was going to sink very quickly when it hit the water again and I was well strapped in. Feeling relief that I was dead instead of having to face mom, the water hit me like a full body punch and I replayed all my sins as consciousness slipped away.

She still needed to hear about me dying the whole school baseball team purple with gentian violet when I put it into the shower heads. A mental image rose in my mind as they needed to play a championship game in orange uniforms while dyed purple. More relief flooded my mind to know that they weren't going to get me. I was not that lucky.

The river was low, I nearly made it across too, and a woman was walking her dog on the other bank. She called emergency services and dived in, got my seat belt loose, and my head above water before I tried breathing it. The disappointment I felt seeing the helicopter hovering overhead while other people did stuff in the water around me was surprising, then I blacked out. I woke up in hospital knowing there was hell to pay, looking around I saw mom's face, and wished for almost anything else. She was staring at me, her mouth a thin pale line, her eyes cold. She was speaking to someone else.

"Take him! I've tried!" She snapped.

"How long?" I croaked.

"As long as it takes!" Mom snapped.

"If you're interested, Craig, you turned eighteen yesterday." Another woman said.

That meant I had been out for three days. I looked around, unable to turn my head. Another woman came into view, her eyes were better to look into than Mom's, and they were still not friendly.

"Your mother has had enough of your bad conduct; you turned eighteen which means I can have you legally. You will be with me until she is satisfied."

I turned my eyes to the ceiling again, this was going to be bad. The car had been the last in a series of things I had done starting when I was twelve. The first thing had been me breaking into a freight rail yard on a Sunday afternoon. I had built myself a train using a small tractor they used to pull light freight around on trailers and I was riding it along the railway line when the cops got hold of me. My reason, when they asked me, was that I wanted to go on holiday again.

The one a week before the crash had been an issue with my girlfriend, well she was ex immediately after it. She had cheated on me (with a baseball player) so I took her to a movie to break up. I took two bite size candy bars into the movie with us and felt her up while it was going, her bad judgment was that she liked to wear white tops. She walked out of the theater and got laughed at with a large brown spot on each breast where the chocolate in my palms had melted. That one had not blown over yet when I crashed Mom's car.

I wondered how much it would help if I reminded mom that I had also done a lot of good in that time. I caught her bookkeeper stealing money from her business by catching him paying for Amazon vouchers out of the marketing account. I was a straight A student too, amazing but true, nobody believed that I had done it honestly, but I had. I faded to sleep as medication kicked in, hearing them talk about ambulances and medi-lift aircraft and needing to find the right person for me.

I woke up in a new room, the ceiling was different. I reviewed: I had been in hospital for two weeks, supervised every second I was awake. No bones had broken, just a few dislocations and a lot of bruises. I had received physio, especially on my neck. In all that time I didn't see mom once, only the people supervising me, usually a woman who looked as if she could go toe to toe with a silverback gorilla, and win. I was not restrained to the bed, a first in two weeks. I had a headache but that was minor. I looked around the room to get where I was.

It was pink. Everything was frilly and soft; except for the low post on a pedestal, that was black, hard, and forbidding. There was a dressing table, a closed wardrobe, a full length mirror, and two doors. I could see a hint of a lounge suite, if I turned my head as far as it could, I seemed to be in some sort of apartment. Of the two doors I could see, one door was probably a bathroom, the other was the way out. I needed the bathroom so I flipped the covers aside and staggered to the door nearest me. It was what I needed most urgently but I had to pause. The toilet had a fabric cover, even the seat was covered. Then I got a nasty surprise.

My penis was locked up. The cage was stainless steel, the piece over my penis was just a bent pipe with a domed cap and a slit to let urine out. There was no way I could pee standing up without peeing on myself, so I sat down. I shuddered with relief as I peed without being supervised for the first time in two weeks.

"Oh! Well done!" A woman said enthusiastically from the door; "Most males make a mess the first time."

"Uh, where am I?"

"Mistress Avelyn's Finishing School for Young Sissies. Have you finished? Remember to wipe!"

I looked down, a drop of urine hung from the domed cap of the tube encasing my penis. I took some paper and dried it up.

"Who are you?"

"Ah, come to our room so that I can explain."

It was not a request. I stood up, flushed, and followed her. After three paces I laughed because I was covering my genitals, there was no point, she had seen them already. Keeping my hands by my side by conscious thought I went back into the room.

"This letter is for you." She said pleasantly, handing me the envelope.

It was from Mom:

Craig, I have had enough. You refuse to be an almost decent human being. You use whatever you wish, as you wish without consideration for the value of what you destroy. You refuse to change your actions when spoken to, you refuse to change your actions when threatened, and I have not been able to punish you severely enough.

For that reason, I got in touch with an old friend, Mistress Avelyn. She is an education and disciplinary expert who is somewhat controversial for her ways. You will be in her school until you demonstrate that you have changed your attitude TO HER SATISFACTION.

Should you resist, or escape, do not come home to me, flee because I will hunt you down. Your trust fund is stopped, your shares in my company held in trust, and your future is paused. I advise you to comply and do as you're told.

This could be goodbye for now, or farewell forever, you choose.

I blinked at the letter a few times.

"Unzip me!" The woman ordered turning her back and showing a long zipper down her back.

I was still processing the letter and reached out to pull the zipper down. The woman shrugged and her dress fell off. There was more underneath, a lot more, most of it black and shiny. For the first time, I saw a dominatrix, and she was mine. She turned around and regarded me then took my hand and led me to the pedestal.

"On your knees, your hips against the drum. Now bend over it. Well done, give me your hand."

I let her have it and she closed a handcuff restraint around it. I was still wondering what was going on when she took my other hand and locked it up. My ankles were locked up before I knew what was going on. She checked everything then opened a box between my hands and took a leather strap out.

"You are now Cindy and I am your mistress. I am Mistress Nikki. Say my name."

"Nikki."

The strap came down hard and fast on my ass. I jerked and tried to rub the sting.

"No, never Nikki. I am always Mistress, the Nikki distinguishes me from the other mistresses."

"Mistress Nikki."

"Well done Cindy. Now I am going to give you a reason to cry for losing your mommy."

She struck again, this time harder. I jerked, struggled, cried out, nothing stopped the lashes coming. I thought about the mild spankings and the psychological approaches that had not had any effect on me. I had known I was wild, and I had delighted in being out of line many times, now I was in a situation where the right words were no help and Mom's money would not buy forgiveness. It was clearly Mom's money that had me here and this was happening because she wanted it to. I started crying, lying still and letting the lashes hit me.

"There, there, Cindy, it's fine to cry." Mistress Nikki said consolingly, stopping the lashes suddenly.

She undid my hands and feet then hugged me and led me away from the pedestal. My ass hurt like hell, but that faded quickly as Mistress Nikki consoled me. When I sniffed deeply and shuddered, She told me to go to the bathroom and was my face, then she could explain how we would carry on.

"This is my bed Cindy, you will only be allowed in it if I order you into it. I know you woke up in it, but that was just a welcoming courtesy. Your bed is on the floor, next to my bed, there's a blanket and a mat under it."

"Yes Mistress."

"Very good Cindy! Now, you will make my bed every morning, and you will help me dress for the day. Then you will clean our place before breakfast, and dress. These are your uniforms."

She opened a small wardrobe I had not seen, at the head side of her bed in an alcove between two buttresses that strengthened it, and showed me that it was stuffed with female clothes. Her wardrobe was the bigger one.

"On school days, you will wear your school uniform, on weekends you will not, but you will only be allowed to dress as you like as long as you conform to the school dress code. On weekends you will wash our clothes in the laundry, you will press them and you will put them away. Are we clear?"

"Yes Mistress."

"Good, now we need to get you dressed for lunch. I am not unreasonable, I will teach you and we have a few days before school starts to get you into the routine. Open your wardrobe, the first item is a slip, you don't need a bra yet."

She took me through getting dressed explaining the dress code for leisure time which was far from comfortable. It included a corset (to be worn properly at all times), panties, a garter belt, stockings (Mistress said I would shave my legs, armpits, and pubic hair that night), and high heeled shoes. They weren't stilettos but that would come, she said. I also needed to wear two petticoats, a full one and a skirt, under my dress. Then I wore my dress, full length with a tight bodice. Mistress Nikki picked a light blue dress saying that she liked it and that I wasn't a sissy yet so pink was not quite right. Before going out she locked leg irons on me saying that all the flight risk sissies need to be wearing iron when outside their rooms.

"We'll handle makeup and dressing me tomorrow. For now you are fit to have lunch. After lunch I will take you for your medical exam, then I will present you to Mistress Avelyn for your orientation. Oh, I almost forgot, your collar and lead."

Learning to walk in high heels at Mistress Nikki's pace while taking short steps because the leg irons would not allow longer took a lot of my attention as she led me through the school to the dining hall holding the leash clipped to a collar around my neck, but not all of it, and I paid attention to how we went. The dining room was basically empty, only mistresses occupied the staff table and two more guys like me were serving their mistresses. They had been there longer and operated without instructions as they fetched the plates, put them down for the mistresses and waited until dismissed to go and eat at a smaller table in the corner. No introductions were made and Mistress made it clear that I was to serve her only.

I had paid attention to the other two and delivered the plate from the right while taking a plate away from the left. She smiled at me approvingly and told me to eat while the staff chatted about the coming term. I felt pretty proud of myself as I ate and took the hint from the other two to not speak. I finished my food quickly and went to the counter to fetch Mistress a cup of coffee, not knowing how she took it, I put a cup on a small tray with milk and sugar before presenting it to her.

"Thank you Cindy! That was thoughtful, but we have to leave now." She said with a fantastic and genuinely warm smile.

The medical exam was done by a matron who took no crap. She ordered me to undress then set about checking me out, nodding approvingly that Mistress Nikki had already used her strap on me. She felt my testicles and pursed her lips.

"Cindy's testicles are not full, not worth milking now. Will you be bringing him back for his milking?" She asked my Mistress.

"No, I'll drain them Matron."

"Very well, give them another few days; when Cindy is dripping and in pain, milking will be easier, and you'll find a very compliant sissy at the end of it. Cindy, get on the bed."

I got on a bed and the matron put my feet into stirrups then restrained my ankles with straps. She worked some controls and my legs were spread with my knees beside my body. She spread some cold gel and pushed something into my rectum, my body resisted but her firm pressure on the instrument had it sliding into me very soon. Then it opened, stretching my sphincter. I was intensely aware that Mistress could see right into my ass as both heads bent down to look. I was blushing furiously at being this exposed and powerless, it meant nothing to the Matron

"Hmm, nice clean colon. His prostate is normal, he's a virgin... take care with his first pegging, take it easy so that Cindy likes it."

"I'll take that into account matron."

"Other than the recovering injuries he came in with, Cindy is healthy and fit." She said moving controls again.

With my feet released, Mistress told me to get dressed while the matron wrote a report and discussed what could be done.

"Bring Cindy tomorrow for breasts. Do you prefer the cage or should we do a procedure for a nice profile with less effort?"

"I believe that more effort would be good for Cindy right now. Let me see if she copes with the routines first."

I was deeply relieved to hear Mistress say that. Breasts were one thing, getting my balls cut to look good in a dress was something completely different. The two carried on talking for a few minutes while I dressed. I was also looking at windows, where I could spot cameras, and the front door if possible. I still had no clue where we were or what direction we faced, but I had decided that I would figure a way out.

Mistress inspected me when I said I was ready and nodded. She took the lead and took me to Mistress Avery. That turned out to be the second woman I had seen with Mom. She stared at me with no emotion in her eyes and indicated that I should turn around. I did and she pursed her lips considering for a full thirty seconds before she said anything, then she started by reading.

"You have been sentenced to an indeterminate term of rehabilitation detention by your mother, lasting no longer than three years. Should you fail to acquire civilized habits, she will disinherit you and we will release you to find your own way. You will not be permitted any contact outside this school while resident here. Any contact the outside world has with you will come through your Mistress. You will be evaluated as to whether you have accepted civilized norms every three months. You have been given to Mistress Nikki at your mother's request and you are responsible to her in all things and at all times, you will serve her and obey her. Mistress Nikki will be responsible for your education, your punishment, your health. Should she be unable to discipline you, I will. I may choose to have you neutered, your mother has signed the documents for that, although that is a last resort. Do you have any questions?"

"Uh, what comes before getting my balls cut off?"

"Hmm. I would suggest that you first experience your Mistress in her full wrath before tempting mine. Where she ends, I begin. Any other questions?"

"There were seventy five seats in the dining hall, nine staff excluding you, the kitchen, and the matron. I don't believe there are seventy five people serving the same punishment as I am."

Mistress Avery raised an eyebrow; "No, there are not. We have seventy five students who are boarding students, here willingly to help their transition to female or sent by their mistresses to learn how to serve well. We have more day students who come to be feminized for their dominant partner's pleasure. It is only the incorrigible who are attached to a Mistress; no doubt you saw the other two here at the moment."

"Are there subjects to learn and pass?"

"There are subjects, yes, and classes. You will have no tests though, not that you can study for. You will be evaluated on how you assimilate the classes into your behavior and conduct constantly and reviewed every three months upon which we will send a report to your mother. Should she deem you to be untrainable, we will castrate you so that you are at least docile. Then, should you request and your mother agrees, transition you to female. In that event she will find you a husband and we will condition you to be a subservient wife to him."

"What if I ask for a dominant wife?"

Mistress Avery blinked, the rest of her expression didn't change but that question had her floored. She had not expected that or even contemplated that I would ask it. I took a perverse pleasure in knowing that she did not think of everything. I had no illusion that she was a brutal bitch to stay away from but she could be out thought and I was confident I could do it again.

"Mistress Nikki is your dominant wife." She said after the slightest pause. "You are a reflection of her, Cindy. Should you displease the mistresses teaching here, they will inform her and she will attend to that before it becomes my problem because I evaluate her by your conduct."

I considered, and felt sorry for Mistress Nikki. Mistress Avery was not finished though.

"You need to understand a few things Cindy. The first is that your mother loves you and this is a desperate, last ditch effort on her part. She called us because we guarantee results and your presence here is subject to a few conditions. The first is that your inheritance will pass to your mistress should you escape because it will be a huge emotional blow to her, she is sharing her home with you and more. The next condition is that she administrates your income while you are here. Effectively, you are paying her to make you a responsible human being. The third condition is that she is practically your wife with full power of attorney of your affairs while you are here. Serve her well, Cindy, because everything you get here will come from her. Should she wish to continue being your dominant wife when you leave, you are welcome to ask her, and that will be for her to decide."

I bought the part about Mistress Nikki getting my allowance and being my wife. I did not buy that Mom had sent me here because she loved me. She sent me because either she would kill me or the baseball team would, it was her anti crime initiative. I was not so sure about the inheritance passing to Mistress Nikki, but that was possible given how angry Mom had been. Regardless, I was in the shit and the one person I had to keep happy was Mistress Nikki, for now.