This story takes place in a land far, far away with different laws. Please don't tell me what is or is not lawful. This is fantasy after all. Not sex story (so far anyway)
I stood in the dock shaking. What had I done? The end-of-term disco should have been just a fun time for everyone. Someone had spiked the punch. We were all over 18 and could legally drink, but the headmaster decided he didn't want unruly behavior.
My friend Mat told me that Janet was wearing very sexy red knickers. He said they were silky with black lace. He said he saw them when she twirled. He knew I had a "thing" for Janet. Normally, I would have just pictured it in my head, but I was on top of the world. I had got a place at a top university and had 3 months of holiday to look forward to.
The alcohol made me do a silly thing. I waited until she bent over the table to cut herself a slice of cake and lifted her tartan skirt high over her back. It was a sight to behold. Her sexy red knickers were framed beautifully by her stockings and suspender belt. Time stood still for me. She was perfect.
Then the screaming and crying started. I was quickly grabbed by a mob of angry young ladies and escorted to the headmaster's study to await the police.
In our small town justice is swift. The council debated if I should be handed over to the courts in the city or if they could keep it a purely local affair. Janet and her parents were consulted and due to my spotless record and charitable works, they decided to keep my trial a town affair.
The JP, the severe-looking Justice Mary Dubois summed up.
"As you are over 18, the act you carried out warrants an adult punishment. You could be looking at 5 to 7 years in prison."
There was a collective gasp and an "Oh no John!" from my mum.
"However. Due to your good standing and the character witnesses who spoke on your behalf, we have decided on an alternative punishment."
I let out my breath. I had felt it freeze in my chest when she said 7 years. My dreams of a good job and prospects would have finished there and then.
"I have discussed this with the victim and her parents and we have come up with a creative solution that satisfies her need for justice..
In the past, we put petty criminals in the stocks for a day or two for the townspeople to ridicule. Shame is a powerful tool. Janet felt shame when you exposed her to her classmates. She wants you to know how that feels.
So, young man. do you agree to the punishment we have decided, or do you want this to go to the city's justice system.?"
I looked at my mother she was nodding vigorously. It was a no brianer. I could handle a bit of shame.
"Yes, your honor."
"When I was a young girl there was a punishment for naughty males called petticoat punishment. This involves forcing them to dress in female clothing. Its intention is to humiliate the 'subject' as a form of punishment.
This court declares that you John Buckingham, will dress as a woman, act as a woman, and work as a woman until the day before you start university.
Furthermore, you will report to Janet's mother Audry Williams, every day to work as an unpaid servant between the hours of 9 AM to 9 PM. "
A roar of laughter went up in court. I was gobsmacked. What could I do? I just had to suffer this for 3 months then put it all behind me.
"As your mother is smaller than you, I would ask the women of the village to donate any clothing they think may fit our new young lady.
You John. have had a lucky escape. I will be checking that you stick strictly to your punishment. Otherwise, I will send you to the city for a more severe punishment.
The sentence is to begin on Monday at 9 AM. Be ready and dressed at Mrs Williams's house. You have the weekend to prepare. "
Janet smirked at me, Her mother looked like a lioness closing in for the kill. She came over as the court slowly emptied.
"You are going to pay for what you did. I'll have you cleaning and scrubbing until you are dead on your pretty little feet."
She stalked away holding her daughter's hand.
At home, my mother made me some hot sweet tea to help with my shock.
"It could have been a lot worse son. You could have been sent to prison."
"But mum, the whole town will laugh at me."
"In 3 months you will be in digs at university. No one there will know."
"Yeah, I suppose you're right."
There was a knock on the door. I listened as Mum answered. It was our neighbor's daughter Sally. She was 20. I had a crush on her.
"I have just brought some of my old clothes. A few dresses and tops. There is also a nighty, a couple of bras and some knickers. I have some shoes too. If they don't fit throw them away."
Sally was just the start. The knocks on the door kept coming. I heard comments like.
"I'm sure he will love wearing these. They are so soft and sexy. My husband used to love me wearing them. "
By the end of the day, I had enough female clothes to fill a charity shop. I was shocked by the amount of underwear. None of it was plain. I think the women got off on the idea I would have to wear their frilly undies.
The JP had made it clear to my mother what was required. I was to be fully shaved, wear makeup, and wear only unmistakenly female clothes. No leggings or trousers.
I spent a miserable weekend while smirking and giggling women, delivered my wardrobe for the coming months.
Sunday morning, Mum ran me a bath filled with scented water and showed me how to shave my sparse body hair. After I dressed in male clothes for the last time. I looked in the spare bedroom.
The room was full of women's clothes. Skirts of all lengths, dresses of all the colours of the rainbow. I opened the drawers. There were sweaters, blouses and soft cotton shirts. The top two drawers contained bras, and knickers of many different shapes and sizes. I held some of them up. Most were soft and silky. Nearly all had frills and lace around the legs and top.
There were other items. Lacy belts with straps hanging down. I recognised these were suspender belts, just like Janet wore the night of the disco. The corner of the room had several pairs of high heels and boots. I stepped into a black pair and wobbled across the room. I was sure I would break my ankle if I wore these.
My heart sank at the thought that I would be doing 12 hours a day of hard labor for Audry Williams wearing these clothes. This was a nightmare. It was due to start tomorrow.
I just wanted to run. How could I go through with this? It seemed like half the women in the town were relishing the thought of me wearing their clothes.
This chapter has some sexual content.
As I walked to the Williams house I dreaded the fresh humiliations that awaited me. It had been a week now, and I was getting used to the feeling of women's clothes. Even at home, my mother made me sleep in a night dress. It was black and plain cotton, but still had a small lace edging. She told me it would be stupid to be caught violating my "parole" while sleeping.
I was growing to appreciate the feel of the clothes. This worried me somewhat. I was a man, how could I enjoy wearing women's clothes? I understood that many were soft and sensuous, but some were uncomfortable. High heels were hard on the feet and the legs, but I noticed how my buttocks tightened while I wore them. As I moved about the house, cleaning, washing and cooking, I could always feel the skirts brushing my thighs. I could feel the suspender straps tugging my stockings. This moved my knickers against my cock. It was almost impossible to keep it tucked between my legs. I lived in fear that Mrs Williams would notice. She would go straight to the judge and get me taken off to prison.
After I arrived, Mrs Williams inspected my outfit. I was wearing a black knee-length skirt, a cream-coloured blouse, black stockings and 3 inch black court shoes.
"Yes, you look like a modern maid. We can do without the costume today. Right follow me" She said.
We went downstairs to the utility room where she pointed a blue plastic basket.
"Right. This is something all women must learn. Machine washing wreaks havoc with your elegant intimates. You must hand wash them. That basket is full of our nicest underthings. You must take care of them."
I blushed. Even though I had been wearing silky underwear for days now, the thought of handling Mrs Williams intimates and Janet's was starting to make me hard.
"Here is what you have to do. Fill the sink with cold water. Delicate items like silk or lace underwear need to be washed in cold water to be absolutely sure that they won’t shrink and that their colours won’t fade. Do you hear me?"
"Yes Mrs Williams." I choked.
"Listen carefully. Add some laundry detergent. Soak and scrub the underwear by hand.. Allow them to soak for a maximum of 30 minutes. Remember to gently scrub the gusset. Did you hear me? If you mess this up, god help you!"
The word "gusset" sent a shiver up my spine. The knickers I was wearing had a soft cotton gusset. They were straining to hold my member between my legs. I just thought of what the gusset of the underwear I had to wash had been touching. I was shocked at what a pervert I was becoming.
I nodded and she continued.
"When you finish, towel dry. Don’t wring out our underwear, it’ll only damage them. Squeeze out the water, roll them in a clean towel, then hang them up on the washing line. After that, go and knock on the granny annex, My mother wants to see you."
Her mother? I knew Janet's grandmother lived with them, but had never seen her. I knew I was in for another scolding.
The underwear I washed was so soft. Much of it was silk. It had names like Fleur of England, Gilda & Pearl and Janet Reger. There were different designs. Some were thongs, some were full. Some were all lace. Why do women need so many variations of underwear? I learned that Mrs Williams was a 36 D cup bra size. Janet was 32 B. As I cleaned the stains from the gussets, I had a strong urge to see what they smelled like. What was happening to me? I was in danger of becoming a real pervert. The urge was very hard to resist. I understood I was curious, but I was worried where this might lead. Was it the immersion into the feminine world that was affecting me?
I was relieved when the job was done. The whole washing line was draped in black, red, peach white silk and lace. It looked like a flag proudly displaying feminine sexuality and power. And I was the one to hoist it.
As I stood at the door of the granny annex, I was curious to see what Janet's grandmother looked like. Was she a pretty as the granddaughter or strikingly powerful like her daughter.
The door opened. I saw a woman who must have been in her late 60s, but looked a little like Raquel Welch. I was expecting a little old lady, but she was stunning.
"You must be Jesse. I'm Donna. Come in and let me look at you."
She dragged me into the well furnished living room and poked and prodded me.
"You do make a lovely girl, don't you? Are you enjoying your clothes?"
"No, I hate it." I lied. Not wanting to admit what I really felt.
She moved her hands down to my waist and caressed my bum through my skirt. I felt the cotton of the skirt slipping against the soft nylon slip and the lace knickers I was wearing. Her perfume was intoxicating. My breathing grew heavy. Her hand moved to the front of my skirt and found my growing bulge.
"There! You are lying. You love being a girl. Not only that, but you are a little prancing sissy aren't you!"
"No I'm not. It's just that you touched me and..." I stammered.
"Well, that means you can't be trusted near the women in this family. I better tell the judge."
"No please don't. It's not fair. I am doing everything that I'm told to do. Please don't."
"I may have an idea. But you must do everything I tell you. Will you?"
"Yes, I promise. " I agreed.
"Follow me then."
We went into her bedroom. On the bed was a heavy looking black garment. It looked like a woman's swimming costume.
"Go to the toilet now if you need to."
I did. My nerves were frayed. I washed my hands and returned to my newest tormentor.
"When I was a young girl, I got a lot of attention from the boys. My mother didn't trust them. Judging from what you did to my granddaughter, things haven't changed. Anyway, do you know what that is?"
She pointed to the bed. I shook my head.
"That is a panty corselette. It gives a woman a nice hourglass shape. Once it is on, it is difficult to get off without help. Take your skirt and blouse off and put it on."
I did as I was told. After I stepped into the tight leg holes, I struggled to pull it up my body. Donna helped me. After the straps were over my shoulders, she started to zip up the back. She tugged and pulled until it was all the way to the top. It felt so heavy. My cock and balls were crushed between my legs. I looked down and saw a smooth front. I looked like a woman down there.
"Normally there is a hook and eye arrangement between your legs in case you need to relieve yourself. My mother came up with the idea of sewing it shut. She knew the only way I could be a naughty girl was to strip off totally. She also knew no man could easily take advantage of me."
"Is that why you told me to use the toilet?"
"Yes. You're stuck in that until someone unzips you. Now all the women in the house are safe from you."
She laughed as I re-dressed, and said.
Go and see my daughter. She is in the master bedroom. She has a little job for you.
Mrs Williams was sitting on the bed. She was wearing knee-length high heel boots, a short skirt and fishnet stockings. I couldn't help but stare at her legs. I had a thing for women in boots, and her legs looked amazing.
She looked amused.
"You like my boots, eh? Good, I want you to clean them."
I knelt down in front of her. My hands trembled as I went to unzip her left boot.
"What do you think you're doing?"
"I... I'm taking them off so I can clean them."
"Oh no. You like them so much, you can use your tongue."
I stopped. I couldn't believe she had just said that. I had recently fantasies of being forced to do humiliating things by beautiful women. I had never felt like this before all this odd punishment. Was I always like this? Or was all this forced crossdressing changing me?
"Well? I'm waiting. Or do you want me to call the judge? "
I knew I couldn't win. Part of me didn't want to. I bent and started to lick the toe of her boot.
She made me lick the soles and the heels of both boots. I felt humiliated, but my cock grew painfully hard trapped in the soft panties and restraining corselette.
"Good girl, now lick all the way to the top."
I obeyed and slowly licked all the way to the top of her right boot. I was breathing heavily as I saw her legs part slightly.
"Keep going girl. All the way to the very top. "
As she said that, she opened her legs wide. I looked up into her eyes. They locked onto mine and she nodded.
"Do as you are told."
I had no choice. That's what I told myself anyway. I had seen pictures of women's pussies before online, like any guy of my age, but this was the real thing. This was a woman I had a perverse crush on.
I wanted to know what she tasted like. Her scent was driving me crazy. I knew about pheromones, but this was a practical demonstration of their power.
She moved forward and our lips met. She grasped my hair and started to grind herself over my nose and mouth. I gasped for breath. All I could smell was her. The taste repulsed and attracted me at the same time. I couldn't pull away and didn't try.
"Now I will teach you how to please a woman. You will thank me for this if you ever make it to uni. You will have girls queuing up for a date if you learn properly."
I couldn't answer. I was fighting to breath as I lapped at her juices. She instructed me for the next 30 minutes until she shuddered and released me.
I was in a huge amount of pain. My cock felt bigger than it had ever been before, but it was firmly trapped.
"Very poor. You are going to need a lot more practice."
I couldn't wait to get home to relieve myself.
Monday morning I woke with a feeling of dread. My mum came into my room at 6.30.
"Come on John. It takes women longer to get ready than men. You'll soon get used to it. Now, shower shave and meet me in the spare room."
After that was done, I walked into the spare room and saw what lay in wait for me.
A pair of smooth black knickers with lace panels at the sides.
"They were the least fussy ones I could find before you moan," Mum said.
I slowly dressed in the soft, unfamiliar clothes.A black bra with lacy cups came next. Mum stuffed them with tights.
"You must have been given 30 odd pairs of tights and stockings. At least you'll be OK if you run a few pairs."
Then she showed me how to put on the barely black tights. These felt absolutely amazing on my shaven legs. I had often heard women complaining about wearing tights. I couldn't understand why.
She had me put on a cream nylon blouse. I had trouble with the buttons as they were the wrong way around. Why are they like that? It was soft and smooth. I never realised that women's clothes could feel so good.
She gave me a black pleated skirt and a pair of low-heeled court shoes to finish off my outfit. Then she sat me down at the dressing table in front of the large mirror.
"Watch carefully. I will do this for the first few days, then you can do your own hair and makeup."
She worked magic on my face. Brushes of powder here and there. Eyeliner, blusher and lipstick. I never knew how much work went into making a girl look pretty. To my horror. That's what I was. She combed my hair into something she called a pixie style, and a pretty teenage girl looked back at me.
"You know John, if I wasn't your mother I would swear you were a girl."
Before I had time to think, she gave me a handbag and rushed me out of the door to walk to the Williams house. I was terrified. The sound of my heels clicking, the zipping noise my legs made as my nylon-covered thighs rubbed together were all foreign to me. I could feel a light breeze blow up my skirt. I felt strangely vulnerable.
A mother pushing a pram came towards me. I was expecting her to laugh and point. She just nodded and said "morning" to me. I was convincing. This may not be as bad as I thought.
The feeling of relief left me when I saw a group of young women standing outside Janet's house. They screamed and surrounded me at the gate. They pulled and pinched me and insulted me.
"Sissy". "Are you wearing my knickers?" "Oh, my boyfriend would love to make you a real woman." "Now you know how the other half lives."
"Who's a pretty boy then?"
I felt a hand grope my bottom. Then Mrs Williams came to my rescue and dragged me inside.
"Good, you made it. Let me lay down a few ground rules. You will obey me and every member of this family at all times. If not, I will tell Justice Mary Dubois that you tried to assault me."
"What! She would never believe you." I said panicking.
"Ha! She is a good friend of mine. Who do you think persuaded her to offer you this punishment? She was all for sending you to the city court."
She let this sink in. What was her motive? I'm sure I wouldn't like it.
"Right, you look very pretty. Much better than I had hoped. BUT you are going to be a servant here, so you need a uniform. Follow me."
I followed her upstairs. She was wearing a tight black skirt and high-heeled leather boots. I found the sight very exciting, watching her bottom move in the tight skirt. Then a thought came into my head. I wondered if her underwear was as frilly as mine. This made me feel a lot less manly..
When we got to the master bedroom, she rummaged in a wardrobe and fished out a maid's dress. It looked like one I had seen some of the women wear at a Halloween party. I had puffy sleeves trimmed with lace and the skirt stood out almost horizontally. It was kept that way by the sewn-in net petticoat.
"You can't expect me to wear that?"
She slapped me hard around the face.
"You listen to me, you little bastard. For what you did to my daughter, I want you to suffer. She cried for hours after. Now you will know what being embarrassed feels like every day for the next 3 months. No strip!"
I was shocked. I did as she said. When I was down to my bra and tights she said.
"No, no, no. What is it with young women today? Ladies wear stockings. Tights are for children."
She got a suspender belt out of her drawer and handed me it along with a pair of seamed black stockings. After a few minutes of instruction. I managed to get the seams straight and she made sure the straps went under my knickers.
For the next 3 hours, she made me vacuum the whole house. I felt ridiculous, but only Mrs Williams saw me. That was until Janet arrived with two of her friends. I turned red as she and her friends cat-called me and made rude comments. Mrs Williams smiled, seeing my embarrassment.
Janet went upstairs, and her mother called out.
"I'll send the maid up with milk and cookies in a few minutes."
Great I thought more teasing. Five years in prison and a ruined life didn't seem that bad now.
I carefully knocked on the door and said. " Your milk and cookies, Miss Williams."
Her friend Sarah opened the door. She was a stunning blond wearing a mini skirt. Her other friend Debbie was a red-haired tomboy. She thought my dress was most amusing. She kept fluffing up my petticoats.
I put the tray down and went to leave.
"Wait a moment, John.. We were just saying we can't call you John. Not a pretty little thing like you. We have decided to call you Jessie. Do you like it?"
What could I say.
"Er yes, er ok Miss. Can I go now?"
"One more thing. Sarah has donated some underwear for you. Look!"
She held up a pink scrap of lace and frills.
"Oh er. Than... thank you."
I went to take it from her and she pulled back.
"Aren't you going to see if they fit.? Girls can change their knickers without showing anything while wearing a skirt. Go on, try them on."
"Umm, no, I'm wearing tights,"
"Don't lie. Mummy hates tights. She would have made you wear stockings the moment she got you into that uniform. Try them of now or I will tell her you flashed us."
What could I do? I slipped my black knickers down and stepped carefully into the pink ones. As I pulled them up snugly, the girls erupted into laughter.
"What? What did I do?" I said,
Sarah touched my arm and said.
"How do they feel? Do they feel a little damp? You know, between your legs."
I did notice that but decided not to say anything.
Sarah turned and gave me a flash of her beautiful bare ass.
They were the ones I was just wearing. Janet bet me she could get you into my knickers within 10 minutes of you walking into the room. I got a little excited at the thought. Sorry."
All three burst into laughter.
I turned beetroot red and went to remove the knickers. "
"Oh no Jesse, You keep them on. Get back downstairs. I'm sure mum has more work for you." Said Janet.
I slowly descended the stairs. The next 3 months were going to be an eternity.