Chapter 5

Sunday went by almost too quickly for my tastes. It was humiliating torment, and yet as it was my first experience with what I will call “Domestic Discipline,” I was savoring every moment. There was so much I could learn from Francine.

I hung her hosiery to her exacting standards out in the backyard. Francine attached the wooden clothespins to my nipples and other body parts. It was painful, but it reminded me that I wasn’t there for my pleasure – I was there for hers!

(Short vignette about the two girls from next door asking him questions? Why are you doing that? What are you outside naked for? I am not naked; I have on a cock cage and a butt plug.)

That evening my mother-in-law taught me another lesson. Francine dressed me as a woman. She made it clear that I was not going to PASS as a woman. “You are not a woman. You will never be a woman. Women have power, command respect, and are a treasure. You are a turd.”

“Then may I ask why you want me dressed as one, Ma’am?” I inquired politely.

“If I want you to know why you are doing something, I WILL tell you. You must learn patience, Jasper. You must also learn what women must go through to look pretty for the likes of you. We do some things that men never notice or appreciate.”

There was an entire process before I was permitted to put on a single stitch of clothing. It involved washing me thoroughly with the garden hose and then powdering and lotioning my skin. Francine expected me to give myself a pedicure and a manicure. She showed me how to apply fingernail polish and a top coat of gloss to my toes and fingernails.

Then we started with makeup she used three different pencils and brushes just for my eyes. I learned the difference between lip gloss, lipstick, and lip liner. She applied blush, set my hair with curls, and extended my eyelashes.

I was not permitted to dress until I was prim, proper, powdered, and perfumed. “The four P’s” as Francine called it.

I had the butt plug, cock cage, and collar when she showed me the outfit I would be wearing out of the house. I knew it would be feminine, but I had no idea I’d be wearing a formal lavender evening gown with long white gloves. They were the kind Aubrey Hepburn wore in “Breakfast at Tiffany’s”

Every thing about the taffeta dress was about glamour and elegance.

Yet, I felt it was intended as a cruel mockery of my manhood – what was left of it. I saw how my face was painted in the mirror, and I made a decent looking woman – albeit not a fully convincing one.

She wouldn’t let me put that on until I had on proper undergarments. These included pantyhose, white cotton panties, and a bustier style bra which cinched my waistline so that I appeared top-heavy and curvy like a woman. I had to suck my stomach in.

“It hurts to look this good, dear” Francine smirked as she admired me in the frilly-girly undergarments. “You seem like a natural. Do you wear Kim’s clothes?”

“No Ma’am,” I replied truthfully. I was taken aback that she assumed that I was a cross-dresser. I suppose I was now.

“Don’t get all uppity. You wear the clothes well, like a natural. This isn’t your first time in panties,” France observed. I was quite flattered. She asked me rather accusingly if I wore her granddaughter’s clothes and I blanched at the sheer thought.

“When I was little, I put on my mother’s makeup, and tried to dress up like a girl once, but I got in trouble,” I admitted. It was a very embarrassing thought. I remember my father spanking me pretty hard for violating my mother’s makeup drawer and experimenting with her things. It seemed perfectly innocent, but Francine read a lot more into it my admission.

“I am not a cross-dresser if that is what you think, Ma’am,” I said.

“You will be after this. If I am going to be seen with you in public, it will not be in those awful jeans. They looked like they had not been washed in jeans. Now, let’s get you some tits.”

She had me follow her into the kitchen. I was thankful I didn’t have to crawl. Francine gave me two chicken cutlets to put into my bra. She explained that tissues can work but the chicken gives the impression that there is some “jiggle to my wiggle.”

Francine had a grand time playing dress up with me. The final touches including the lavender dress, pink hat, white gloves and patent leather shoes with five inch heels. She held up the heels and had me suck them like they were a dick to clean them. “I have heels longer than your penis. Do you realize how pathetic you are?”

“Yes Ma’am,” I blushed.

She finished my ensemble with a matching white purse, a bedazzled choker to accent my pink collar and some fake earrings that dangled like small disco balls from my ears.

Francine instructed me on how to walk in heels. I was not supposed to step or stumble. I was expected to glide gracefully across the floor while wiggling my ass and jiggling my tits. She wasn’t entirely satisfied, but then she expects nothing less than perfection. I spent a long time learning to push my tits out and hold my shoulders back like a ‘proper lady.

I will admit that despite the tedious nature of taking over an hour to prepare to leave the house and all the effort that went into just trying to carry myself like a woman – I actually enjoyed the exercise. It gave me a whole new perspective on why the women of my house always take much longer than Freddy and I to get ready. They want to look good for themselves and others – and the process is tedious and time consuming. I was ready to thank Francine, but she didn’t like it when I spoke without first being spoken to, and she was prepared to leave the house.

She took me outside to her car and handed me her keys. I was surprised she trusted me to drive her vintage 1978 Lincoln Continental. The car was full of curves that matched her voluptuous figure. I smiled as I was looking forward to taking it for a spin.

That is when I heard the older Gentleman from the mornings suntan episode. Her neighbor was watering his hedges. “Hello Mrs. Walker, you two look lovely today.”

“Oh thank you, Mr. Johnson,” Francine turned on her heel to face him. She presented me as if I were her protégé’. I felt inclined to curtsy, and so I did.

“Hi, you both look so beautiful. Where are you going?”

Francine answered that we were going to a cotillion event for the Red Hat Society. I imagined it was some sort of fancy ball for debutantes.

“Is this one of your granddaughters I hear so much about?” Mr. Johnson regarded me with curiosity. I didn’t know what to say, but he was clearly talking to me.

“Speak up,” Francine snickered and prodded me to answer.

“No sir, I am her son-in-law,” I don’t know why but I tried to speak in a higher pitch like a woman and failed miserably at it. I can’t quite describe Mr. Johnsons facial expression but imagine the intersection point between horror, disgust, and surprise and you will probably find it there.

“Come along, we don’t want to be late,” Francine could barely contain her laughter as she walked me to the car. I immediately opened the driver’s seat and sat down. “Are you forgetting something?”

It took me a moment to realize that Francine expected me to open her car door and she planned to sit in the back of the car. “You make Kim open her own doors?”

“I usually open them if I am first through the door, but I’ve never opened her car door, Ma’am”

Francine rolled her eyes and said that would have to change. It was a small thing and one I wouldn’t feel humiliated about doing. It may add a few minutes to getting everyone in the car to go somewhere. I felt that was perfectly reasonable as I held open the door for my mother-in-law.

Once we were driving down the road, she told me the directions to take and commented on the interaction with her neighbor. “Is that pathetic voice you did for Mr. Johnson what you think women sound like?”

“No, Ma’am, I just wasn’t sure what I should say.”

“You did the right thing by telling the truth. I was surprised you were capable of that,” Francine offered a left-handed compliment. She told me that she had a gift for me that would help at the cotillion.

“Thank you Ma’am,” I immediately sounded grateful. Francine told me to look in my purse and take it out when we were stopped at a stop sign. Inside was a small, chubby, life-like dick shaped dildo.

“Suck on that while you drive,” she instructed.

I was very hesitant. There was no window tinting available and it was still light out. Anyone would be able to see me sucking a dildo. I didn’t argue though.

“Take it deeper, to the back of your throat,” Francine gave me tips on how to fit the entire thing in my mouth. I tried to imagine it was a delicious Italian sausage that I was enjoying. I almost didn’t notice the man leering and honking his horn when he saw me going down on the dildo at a traffic light.

He was extremely happy he caught me until I looked right at him, and he realized that I was not a woman at all. He drove away angry. I was completely mortified, but Francine wanted me to continue even more. I assumed this exercise was just to amuse her, but she had another reason.

When we arrived at the ball, she made me take the entire dildo into my mouth – down my throat. I had to stick it in two or three times. Then she said “Smile” and added “breathe through your nose, piggy.”

I did so and she insisted I close my teeth. “Good, if anyone talks to you, all you will do is smile and nod. There will be no funny voices here, Rich Little.”

I hadn’t heard a reference to the famous impressionist in years. I smiled at that, and she led me into the main hall of a posh country club.

The cotillion consisted of about 30 older women in red hats. They were mostly eating finger sandwiches and gossiping amongst each other. I had the distinct impression that there was a lot of silent feuding and internal politics between these women. The majority of them seemed like women with extremely strong personalities, but none were quite as attractive as Francine.

There were approximately half that number of younger women in pink hats. Most of them were quite stunning and were dressed much as I was. I believed I was passing for one of them in part because I blended in with the other pink-hat girls. The practice walking in heels was paying off, and I tried not to clip-clop my feet on the brocaded Italian tiles in the courtyard as we made our way to the main hall.

Inside the main hall, there were also men. Most of them reminded me of Mr. Drysdale, the banker from the Beverly Hillbillies. They were dressed in Tuxedos and looked rather dashing. They ranged in age, but most of them were about Francine’s age.

They kept to themselves at first. There was a DJ playing cocktail music. I think the song was George Benson’s Breezin’ when I made my interest. I expected silverware to drop and shocked faces, but no one seemed to see through the feminine illusion I was wearing. I kept a huge smile on my face – what choice did I have?

I wanted desperately to gag and spit the dildo back out. Instead, Francine kept me in the spotlight by squiring me around. She introduced me as “Justine” and said I would be visiting her every weekend. She did not call me a family member though.

The first time someone asked me to dance, I nearly spit out the dildo. Francine offered my hand to the gentlemen, and he led me out to the dance floor. I am not a very good dancer, and I was incredibly nervous that I’d blow it.

He looked about my age, and he clearly had no idea I was a man. The first song was Madonna’s “Like a Virgin,” and I did my best “wedding bop” where I swivel my hips and move my hands in time with the music but don’t move around too much. He actually mirrored my dance steps, and I kept a big smile on my face.

I wondered if dancing with a man-made me gay? I was dressed as a woman and literally had a four-inch long dildo in my mouth. I tried not to think about it because my cock was fighting hard to escape the cage it was in. I was thankful (for once) that I couldn’t get hard and blow my disguise.

The song was probably three minutes, but it felt like thirty minutes. I was grateful when it ended and started to leave the dance floor. Ready for the World’s “Love you Down” came on next. This is a slow song, and the man wasn’t finished with me. He held me close and put his arm around my back just above my buttocks.

I could smell the martini and olive on his breath. I could smell his masculine cologne as well – it seemed offensive to me. He was breathing down my neck, and he was basically hugging me tight while we glided around the dance floor to some old forgotten 80’s ballad.

I don’t think the word ‘humiliation’ quite covers what I was feeling. Intense humiliation doesn’t either. You know that feeling when you feel like you just want to jump out of your skin and be someone/somewhere else and never think about what you are doing again? Double that and multiply it by total emasculation and you might be close to the word I am seeking to describe how I was feeling.

I could feel his heartbeat against mine. “You have a nice ass,” he whispered in my ear.

I nodded politely that I agreed.

He took that as a sign he could move his hand down my dress to rest his palm on my butt. I could have moved his hand, but I didn’t want to cause a scene. He tried to take my hand and put it on his cock while we danced. I didn’t let him, and he laughed “Oh, you won’t do that until I take you to dinner?”

I shook my head no and smiled. Add men exist to serve women – but you are no man Jasper – you are less than that, do you know that? It is why I like you. I think I’ll permit you to come back next weekend. You must practice all week. I don’t want your daughters seeing your little cock cage or butt plug. However, you can walk around your house in panties and heels - they suit you.

I waited politely for my wife to pick me up, but made no mention of whether I would return next weekend as requested. I knew she expected it – but surely my wife would never make me return? I’d have to tell her what happened this weekend! I was ashamed and hoped Kim would probably never believe it.