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.