The Stories Your Mother Never Told You — Part 2.

From the dusty journals provided by one of my guests, I have selected a series of entries that disclose the sordid feminization of one poor and unsuspecting young holiday visitor. These distressing entries are provided for educational purposes and as far as I can see must have been written in about 1955. MM

The following day Jack enjoyed the sunny morning, but as is not unusual at that time of year, a small squall came in off the sea in the afternoon.

“Jack, come inside,” his aunt called as the first drops of rain spattered on the windows.

“I want to play outside,” he protested, but Aunt Magdalene insisted.

“I have a different game for you to play today,” she said. “Let’s play dress up.”

Jack was eager to please, but at first not really interested in this game. As he walked up the stairs, he wondered how long it would take for the squall to blow through.

Jack entered Magdalene’s bedroom to find her standing by the wardrobe, with her back to him. She had tossed a blouse onto the bed, and wore no skirt. She stood in nylons and her underwear, back to Jack, looking through her wardrobe.

“Jack, darling, what do you think of this slip. It’s very silky, isn’t it. Here — feel it.”

Jack tried to look away but found his eyes kept drifting back toward Aunt Magdalene. He’d never seen his mother or anyone else for that matter looking like this, and felt embarrassed.

“Goodness, Jack. You’ve gone beet red!” said Magdalene. “There’s no need to be embarrassed. You’re just a little boy! You help me choose and don’t be so silly.”

Jack touched the silky fabric. He felt uncomfortable, but was aware that he liked the feeling. How strange it all seemed. Auntie Magdalene’s chest was much bigger than mommy’s, and the way she leaned over him made him almost breathless.

“Jack, hand me that brush,” she said. “Oh, won’t you brush my hair for me?”

Magdalene sat before the mirror and Jack stood close behind her. “That’s it,” she said. “Just use long slow strokes.”

As he worked she encouraged him saying, “Oh Jack, that’s very good. You could be a hair dresser when you’re big. Don’t you love long hair. I think you’d look nice with long flowing hair, don’t you?”

Jack found himself stiffening in ways he’d never felt before, and had to admit he was enjoying himself.

“Oh, Jack. You’re really very good. Now, won’t you help me into this dress,” she said at length stepping into a long dress she had set aside.

“Just do up the fasteners for me. What a good fellow you are,” she said.

Jack loved to watch Auntie. He found that it was ok to see her in her small clothes, as he thought of them. In fact, he liked to.

+++

It was just a couple of days until the ladies returned for their drinks party. Magdalene decided that if she was going to do this, young Jack had better have a trial run first.

“Jack, we’re going into town today, but I want to play a practical joke on one of my friends. I want her to think my niece is in town. I’m going to dress you up and I want you to be a good little actor and pretend. Does that sound fun?”

“Well, I guess,” he said reluctantly.

“Oh, come on. This is going to be wonderful,” she said. “Come on up to my room and talk to me while I dress.”

Magdalene chatted busily as she chose some clothes for herself and began changing in front of Jack. She kept her girdle and panties on, but pulled on some nylons and a suspender belt.

“Let me show you how these work, young man. You never know when this kind of thing comes in handy!” She guided his hands over the garments and fastened the nylons in place. Kneeling beside her, he copied her and looked up at his auntie.

“Now, I am going to put a little make up on you, not much mind; and I’ve got some clothes for dress up.”

Magdalene pulled the clothes she’d bought from a smart box and laid them out. The frilly panties were most prominently displayed.

Jack looked at them, flushed red. “But…”

“Come along, Jack. Get those silly things off. Let’s hurry along. I’ve even got some sunglasses for you!”

“But I want some clothes like yours!”

Aunt Magdalene gasped in surprise. “You mean the nylons? With the suspender belt?”

“Yes.”

“Well, I can try and find some,” she said laughing.

“That would be wonderful.”

As Magdalene fastened the bra, slipped a smart blouse on Jack and pulled the dress up to his waist, she said how very pretty he looked. In that moment he felt as happy as he’d ever felt.

Aunt Magdalene was looking at his groin. “Well, I don’t know what to do about that!” she said. Never mind, she thought. Time would sort it out, and besides, he’d be sitting in the car when outside anyway.

+++

The drive to town was uneventful. The hood on the old Chevy was down, and the sun whipped through Magdalene’s hair. She wore big black sunglasses, and Jack’s matched perfectly.

“While we’re out you should probably stay in the car. I’ll probably call you ‘Jaqueline’ if anyone asks, ok?”

“I like that name,” replied Jack.

At the gas station a young man came over and filled the tank. He didn’t give the little ‘girl’ a second glass, but fawned over Aunt Magdalene, who wore a blouse that was generously open. The young man polished her windscreen, wiped down the chrome door handles and shined up the mirrors.

“One of these days,” she said to Jack as they pulled away, “You’ll learn how powerful a little attention to your clothing can be.”

In town ‘Jaqueline’ remained in the car. Auntie Magdalene shopped in the haberdashery once more, this time returning with more underwear, probably the wrong size, but nothing she couldn’t adjust. She was having so much fun, should could hardly remember being so happy.

As they flew back along the highway, Magdalene told Jaqueline to wave at any young boys he saw.

“Look for the teenagers. They love it,” she said.

As he waved at a car the big Chevy raced two teenager waved eagerly back, smiling and chattering. Jack felt wonderful. No teenager had ever paid him any attention. This really was fun.

By the time they reached the house Jack felt wonderful, and decided he definitely liked this game.

+++

On Monday morning Magdalene decided to try to curl Jacks hair. It wasn’t really long enough but if nothing else, Jack loved the attention. In the background the radio played, and Magdalena sang along.

“Let’s try these lovely new clothes,” she said. “You’re going to look so lovely when the ladies arrive.” She said.

“But won’t they think it strange that I’m dressed like a girl?”

“Oh, no!” Said Aunti Magdalene. “They’ll think how very clever you are. I know they’re going to love you. I want you to stay upstairs though until I call you down. Then, you must walk slowly down. Do it exactly as I told you.”

“You were walking in heels. I don’t have heels.”

“Well, if you do very well, I might just try and buy you some. Let’s see how you do.”

Jack was silent a moment. He was enjoying himself enormously. And now that Aunty Magdalene had showed him how to wear the complicated clothes she’d spent so much time adjusting, he felt magnificent.

“I do like heels.” He was staring at his feet.

“Jack… or should I say Jaqueline… I know what you did last night.”

Jack was silent.

“I found my shoes out of order. I know you’ve been going into my closet and trying them.”

“I’m sorry. I didn’t mean to,” stammered Jack. Would she smack him, the way mommy sometimes did?

“Jaqueline, it’s quite alright. I don’t mind. You can take any of my clothes you wish, as long as you leave them clean and tidy afterwards. Really, Jaqueline. It’s ok.”

Jack felt a wave of relief and realized Aunty Magdalene really was wonderful.

+++

Her voice drifted up from downstairs.

“You can come down now, darling.”

That was his cue. He took a last look in the mirror. His cheeks were a little red, but that was to be expected. He looked so pretty in the skirt and blouse.

He slowly stepped down each stair, just as Auntie Magdalene had taught him. He kept his gaze level, without a trace of self consciousness. There were six women below looking up at him and as he descended he realised they were staring at him in amazement.

One reached for her drink and gulped it down clumsily, saying “Remarkable!”

“Oh, Jack,” said another. “You’re amazing.”

“It’s Jaqueline,” he said lightly. Another round of gasps.

“Good heavens,” said one of the younger women. “This is extraordinary. Come and let me look at you.”

Jack walked up to her, looking her in the eye as his auntie had told him to. The woman looked him up and down, and then leaned forward and kissed him firmly on the lips. It didn’t feel like when mommy kissed him.

Beside her another woman stared. “Goodness,” she said, and touched his hand. She pulled him closer, and she, too, leaned over and kissed him.

He didn’t really like the kissing, but the impression he’d left on Magdalene’s friends was clearly a good one. One by one each of the ladies gave him a hug and a kiss and he felt wonderful.

“Jaqueline,” said Aunt Magdalene. “None of the girls here have any secrets. I wonder if you could just show them your lovely undergarments. Would you mind?”

“No,” Jack replied. “They’re beautiful.”

Slowly unbuttoning the blouse, Jack discarded it, and then unclipped the waist fasteners on the skirt. As he stepped from the clothes a beautiful little corset and nylon set was revealed. The ladies gushed, and touched and stroked Jack, and to his horror he noticed his panties gradually growing out of shape.

“Now, Jaqueline, you sit by me here,” said Magdalene. She tactfully draped the blouse over him to provide a little modesty. Then she rose and refreshed the drinks.

“What a clever little girl Jaqueline is,” they all agreed.

And that was the start of a series of summer holidays unlike those shared by many of Jacks friends. Of course, what happened in California was no one’s business but Aunty Magdalene’s and his. And he felt wonderful about it.

Be sure to join me and follow me on Medium — https://fionadobson22.medium.com/membership