CHAPTER 8
FEMINIZATION
Mommy came into Stuart's room. She asked "Stuart, you've been running around the house stark naked for what, months now?"
Stuart blushed at being reminded of his unclothed state and answered, "Yes, Mommy."
"You DO remember your lessons, that nakedness brings humility and service, correct?"
"Yes, Mommy."
"Well, you haven't complained about it, so as a reward I've been shopping online and bought you some clothes."
Stuart's face lit up in delight.
"Really, Mommy? Can I see them?"
"Of course, dearie. Go and fetch Mrs. McGregor, and meet me in the living room "
She had package after package waiting when they arrived.
She started pulling out tissue wrapped bundles.
"We'll start with these."
She unwrapped a pair of sheer, lacy woman's panties.
Stuart's eyes went wide.
"I..I...I can't wear THEM!" he exclaimed.
"Of course you can, and will. This is what you will be wearing every day now. Besides, you know that Mrs. McGregor and my panties get you erect in seconds, right? I mean look at your little peenie right now!"
Stuart blushed a bright red.
She continued unwrapping. Thong panties, bikini panties, hipster panties, brief panties, high cut panties. Lace and satin, plain and fancy, ruffled, even some crotchless panties. Plain white cotton panties, little girl panties with Pooh Bear, Hello Kitty and Mickey Mouse.
Mama held up a pair of pink lace bikini panties. "I think these are my favorite."
Stuart yelled "I'm NOT wearing them!"
Mrs. McGregor stood, grabbed Stuart by the ear and dragged him to Mommy, then forced him over her lap. She wedged his head between her own legs as Mommy started spanking Stuart.
Fifteen minutes later Stuart was a crying, sobbing mass laying at Mommy 's feet. Mrs. McGregor dragged him upright by his ear, facing Mommy.
"Two things, Stuart. You WILL wear what you're ordered to wear. And your erection when I started pulling these panties out gives you away. Doesn't it, Stuart?"
In a whisper Stuart said, "Yes Mommy."
"Good. I forgive you. Now for the rest of your new clothes."
Mommy opened and brought out bras, garter belts, and stockings, and corsets.
"This is cute" Mama said holding up a stocking package. "Crotchless pantyhose. They will leave you completely exposed."
Next she pulled out corsets. There were several types, overbust, underbust, waist trainers, longlines and cinchers, bustiers, in all sorts of materials, satin and mesh, cotton and leather, even brocade.
"The steel boned waist trainer corsets will do an especially good job in shaping your waistline."
The corsets came with a belt Stuart didn't recognize, but soon learned was a locking shackle.
"Now the shapewear, Stuart. And these are called panty girdles. I particularly like this panty shaper, the built in thong lifts and separates your ass cheeks. I also like the long-line girdles. Get one of these on and you can forget about playing with your peenie. Of course this open bottom girdle gives free access to your peenie. And has six garters, too."
"Now, night clothes. I got you two full-length satin nightdresses, several lace and sheer baby dolls, a lacy chemise, a pink satin boys shirt. I just love this, a lace and chiffon peignoir. AND you have a sheer black kimono to wear."
"Oh, and this is lovely" She held up a chemise, sheer white, bell sleeves with lace trim on the arms and a very feminine bow.
"Next I bought you some makeup. This cute little kit contains everything you'll need to make yourself pretty. Let's get started with that, okay?"
"Ah, yes, here are the breast forms for you . You will look much more feminine when you wear these."
"Please, Mistress...not....not..."
"Yes, Stewart. You WILL wear them. They will give you a delicious feminine figure."
"And of course I didn't forget to buy you wigs. Lots of them."
Stuart was wide eyed and shook his head.
"And then we have some really cute aprons for you to wear."
"Let's see. Ah, yes. Open these."
Stuart discovered that she had bought an assortment of chastity devices. And butt plugs.
The piece d'resistance were the high heels.
Shoes of all kinds, pointed toe mary-jane, mary-jane platform, 4 1/2 Inch Heel Black Patent Mary Jane, T-strap, black patent pumps, closed & open-toed wedge, mule, slingback, ankle strap, open toe stilettos, platform wedges and boots, 4 1/2 Heel, Mary Jane Pumps
,
4" Marabou slippers with a puff of fur, Victorian ankle boots and more.
"And these are very convenient for training, Stuart. They're call shoe locks. They go around the shoe and then, viola! they lock, making it impossible for you to remove your shoes. Ingenious, huh?"
"Oh, I forgot. Stockings. Let's try on a pair of your new panties and a pair of stockings, shall we? I'll even let you pick a pair."
He picked the pair of lacy pink briefs Mommy had shown him earlier.
"Step in, honey."
Mommy held them open for Stuart step into. He was naked and trembling, but obeyed. Mama pulled the panties up to his waist, then Mrs. McGregor started stroking his penis and balls and ass.
"Don't they feel good, Stuart?"
"Yes Mommy."
"Your little peenie looks so pretty, all hard and showing so nicely, sweetie. I guess you like your pretty panties."
"Oooff... Governess, that feels so good."
She continued slowly stroking his peenie.
Finally the slave boy gave a shudder and came into his pretty new panties.
"Get cleaned up, I want to see how you look with more of the panties I bought you."
Stuart removed the sopping panties, wiped his penis, then licked the panties crotch clean.
For Stuart's first corseting Mrs. McGregor took Stuart to the Mistress Chapel, bound his hands above his head, then forced his feet into a pair of thigh high pink boots, then ball gagged him.
"That's so you can't complain , child."
The corset, in hot pink vinyl, is wrapped around her waist and then laced up. Mrs. McGregor then had Maid Marta start tightening the laces in order to close the corset in the back. She finally resorts to placing her foot in the middle of Stuart's back and shoving while pulling the laces to finish the job. Stuart is whimpering during this whole process, but the final tugs make him give a gag muffled wail as the two edges meet in the middle of his back.
Mrs. McGregor ties off the laces, then walks around to inspect her handiwork.
"Verra nice, Stuart. You have a nice hourglass figure now. We'll leave you here so you can get used to the feeling of being feminized and corseted."
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For the next five days Stuart went through intense coaching as to how to walk in high heels. Each day the heels got higher and higher.
Mrs. McGregor started by dressing him appropriately, a tightly cinched corset, black fishnet stockings and one of his new wigs. Then she would lead Stuart into the shoe closet. She would place the shoes on Stuart's feet, then use locking shoe straps. His erection was on prominent display while he was being dressed.
She really didn't like him being erect for this training, so she had Stuart pick out a chastity cage, forced him into it and locked it shut.
"I really like the pink silicon chastity cage you chose, Stuart. You'll wear this for the next several days, until your training is completed. Now let's begin."
She had his walk up and down a few times, to get used to the feel of the heels. Placing a book on his head, she had him walk back and forth. For the next few hours she had him practice walking in the heels. Showing him how to walk placing his heel down first and adding a little mincing motion with each step. How to place one foot in front of the other. How to move his hips with each stride. Arms had to be held elbows in, forearms raised, hands held limply. However, if the book fell from his head he has to bend over, hands on a table, for a stripe from Mrs. McGregor's cane. His ass was marked many welts from the cane, but he was eventually able to walk across the room and back without losing the book.
The next day his training continued using the same technique, but now the heels were even higher. As a bonus, Mrs. McGregor had a vibrating butt plug ensconced firmly in his ass. She promised him two stripes of the cane if he lost the book.
The third day she had him dressed, wearing the plug, then something new. Tying Stuart's hands together in the middle of his back, she place a heavy book on his head. Hanging from the book by a string were two nipple clamps. she attached them, then instructed Stuart to start walking. The pain in his nipples was bad, but he was terrified in case he DID lose the book, the pain would be excruciating. And the promised caning was three stripes.
The day's training over, Mrs. McGregor had Stuart kneel on a cushion, a book balanced on his head, another book lying in his hands, arms fully extended. Dropping any of the books earned him another stripe from the cane. Mrs. McGregor finally decided that he was too exhausted to continue, so she had him lean forward, head on the ground, arms extended out and delivered another half dozen with the cane.
Day 4 consisted of Stuart walking up and down a set of stairs, wearing a lovely tight, sheer white dress, almost a hobble skirt. His pink chastity cage was visible through the sheer material. Over and over again. At the beginning of the day Mrs. McGregor allowed the boy to hold onto the banister. Three hours later he was perfectly comfortable walking up and down the steps unsupported. And his rear was crisscrossed with marks from the cane which also showed through the dress.
Day 5 continued the training, but with a twist.
The locking shoes straps were connected with a short chain, forcing him to take even shorter steps, and making the book balancing even more difficult.
At the end of the day the slaves rear was a masterpiece of the art of caning: crisscrossed welts all the way down to the thighs.
Of course interspaced with his shoe training Stuart was forced to don all sorts of feminine underwear, and accouterments.
At the end of the fifth day of Stuart's training Mommy and Mrs. McGregor were talking.
"Margaret, you are a miracle worker. I never expected Stuart to accept being feminized without making a fuss. And he is just so...so..."
"Horney?"
Mommy burst into laughter.
"Exactly. Anyway, I'd like to give you this."
She handed an envelope to Margaret.
"It's a bonus for doing such a good job."
Inside was a check for $100,000.
"Vanna, I never expected this. It's...it's incredible."
"Well, you earned it. Now let's call Stuart in and give him a little treat, too."
