A Cruel and Unusual Punishment Ch. 02

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 cam 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.

Any feeling of relief left me when I saw a group of young women standing outside Janet's house. They screamed and surround me at the gate. The 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 goof 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 a frilly as mine. This made me fill 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 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 underwater to 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 snug, 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 decide 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.