Chapter 3: Michele’s Story

The four Wrens of Collins Division woke at ‘call the hands’ at 0640. Doris had got out of bed at 0600 to prepare breakfast and was in the galley. She’d tried her best to do her makeup and dress like a Wren but she still looked like a ‘scranbag’; not that it mattered, in the steam filled, greasy kitchen. Her hair was matted and her makeup ran as she sweated over breakfast.

Michele, Polly and Mary shaved and took their time applying makeup, pulling on and brushing their wigs and dressing in their Wrens uniforms.

“Ok girls; let’s get breakfast. Try not to upset Spike or get the other Leading Recruits offside,” Michele said faffing around her charges and making sure they met her standards.

In the café, the Wrens sat at their table and ate their breakfast; very aware that the four Leading Recruits were looking at them critically. Michele kept her two Wrens engaged but she noticed that both Mary and Polly were preening and glancing across at the boys table.

“You two need to be careful,” Michele said.

“What on earth do you mean?” Polly asked.

“You know what I mean. You like it that the guys find you attractive. You don’t know where this might lead to, we still have the best part of six weeks to go,” Michele said.

“Oh come on Michele; it’s just a jolly! We look great dressed as Wrens thanks to your help but it’s just another way for the Leading Recruits to intimidate us. At least now they seem to appreciate us and don’t treat us like shit!” Polly replied.

“Yeah ... Well just be careful,” Michele said.

Polly and Mary gave Michele an insolent look and glanced over to the men’s table and were happy to see that Jimmy, Jean and Billy were furtively glancing their way. Polly wriggled in her seat and smoothed her skirt ensuring her stocking-tops were on display and was rewarded with a gasp when the boys saw her thighs. Mary pushed out her breasts and ran her hand though her hair and was rewarded with a smile.

“Just be careful!” Michele snapped again and stood up and left the table.

She went back to the block and made a brew and sat outside smoking a cigarette, drinking her tea. She was worried about her friends who had now become her charges; were they really that naive? Polly seemed very taken with crossdressing as a Wren, she obviously enjoyed the attention, and Mary was similarly engrossed with her female persona and happy to be an object of devotion rather than derision. Doris was not happy dressing as a Wren and Michele wondered if it was genuine disgust at having to dress as the opposite sex or whether she was pissed that she really didn’t look that good dressed as a Wren because of her weight.

She glanced at her watch and saw it was 0805 and time to turn too. HMS Chelmsford was ‘out of routine’ during the ROP, flag Charlie flying from the yard, indicating that the ceremony of colours and sunset was in abeyance. Normally both watches of the hands mustered on parade and reported for duty followed the hoisting of the White Ensign at 0800. Today Michele flicked her cigarette butt into the spit-kid, put her cigarettes and lighter into her pockets and made her way over to the administration building and the regulating office.

Leading Recruit Jones sat with his feet up at the Regulator’s desk, his spit-polished boots resting on the edge of the desk as he smoked a cigarette and sipped tea. He deliberately did not acknowledge Michele as she entered the office, removed her jacket and hung it on a peg, and sat behind the desk where the Wren Writer usually sat to type out Daily Orders, watchbills and various Memoranda.

However he did notice that once again she smoothed the seat of skirt and crossed her legs at the ankles; very ladylike peculiarities. The silence was icy and neither of them wanted to recount what had happened when Spike has spanked her last night.

“Get your pad and come over here Wren Nyland and I’ll dictate Daily Orders for tomorrow,” Spike said.

Michele picked up her steno pad and sat on a chair in front of Leading Recruit Jones, acutely aware of his gaze on her pretty face, her body and on her legs as she crossed them and smoothed down her skirt. Her right knee crossed over her left and she unconsciously rocked her right leg and dangled her shoe.

“Ok enough bullshit Michele. You know too much about dressing like a lady, makeup, clothes, wigs, the whole lot. And your mannerisms and voice; you can’t learn them in two days. What’s the story?” Spike stared at her.

Michele just sat, head down staring at the floor, dreading being here alone with Leading Recruit Jones. She raised her head and looked at him defiantly but there were tears forming in the corners of her eyes.

“You know you’re going to tell me; even if I have to spank it out of you,” Spike winked at her but Michele saw the cold malice behind the wink and shivered.

“Ok. This is my story,” Michele began...

Michael was born late in his parent’s marriage, an accident that occurred when his mom was in her mid-thirties. He had four older sisters who pretty much raised him in their mother’s absence as she was businesswoman who thought her child raising days were behind her. His sisters had no compunction in getting around the house partially clothed in his presence. They regularly turned up for breakfast dressed only in slip, bra, panties and hose. Their makeup would already be applied and they would eat their breakfast dressed only in lingerie. His sisters noticed his fascination with how they were dressed and teased him. They made him wear panties and slips to bed instead of pajamas.

They often held him down and put makeup on him, teasing out his long curly locks, dressing him in their lingerie and dresses, skirts, blouses, and heels. By the time Michael entered his early teens his sisters had married and left home but his predilection to crossdress was ingrained.

The feel of the sleek fabric of stockings, panties, bras, slips and suspenders on his skin was like nothing he had ever experienced in his short life. The flick of a hem, the sense of his skirt or dress against his thighs, flicking his fringe out of his eyes, wearing high-heels making his buttocks and legs taught and shapely. The taste of lipstick and smell of perfume, the reflection of his heavily made up face in mirror; it was all indescribably arousing to him.

In his late teens, Michael was left alone most of the time; his sisters having married and moved out and his parents away on business he had the place to himself a lot of time. He acquired all the requisites he needed to crossdress and spent hours and sometimes days dressed as a woman, luxuriating in feeling feminine. He often masturbated whilst dressed; but it was more about the comfort he felt whilst dressed enfemme than the sexuality.

His life changed forever not long after his nineteenth birthday. Michele was dressed enfemme as usual on a rainy Saturday afternoon and was sitting quietly engrossed reading a fashion magazine. She never even heard the front door unlock nor the footsteps of her Uncle Bill and was shocked beyond speech when she looked up to see him standing over her.

“Oh my god!” Michele clasped a hand to her mouth in surprise.

“Oh my god! Is that you Michael?” Bill looked astounded.

“What are you doing here?” Michele asked.

“Your dad asked me to drop in and make sure you were ok; he and your mom have been away for over a week and were worried about you,” Bill replied.

“And you couldn’t call first! You couldn’t knock! For fuck sake Uncle Bill!” Michele began to whimper.

“Look we need to talk about this Michael,” Bill demanded.

“This isn’t about me, it’s about you,” Bill went on.

He sat down next to his nephew.

“It’s Michele,” Michele sobbed.

“When I’m dressed I’m Michele,” she explained.

“Ok Michele; do you want to explain?” Bill asked.

“Are you going to tell mom and dad?” Michele asked.

“Tell me about it first Michele,” Bill said placing a soothing hand on her shoulder.

Michele told her uncle about how his sisters dressed him as a girl and about how she had come to love dressing as a girl and did so at every opportunity.