It wasn’t until I was in my mid-twenties that I plucked up the courage to leave the house dressed as a young woman. Initially, it was short walks to the end of our street (a relatively quiet suburban road in a relatively quiet town). My hair was fairly long in those days, with blonde streaks through a feather-cut. I’d comb down a fringe to my brows to give me a more feminine look.
Over the years, I had tinkered with make-up, and by the time I was ready for a “Walks On The Wild Side”, I was proficient enough in that department.
I married the first time, at the age of twenty, and managed to hide my secret taboo from my wife for about ten years. She worked in a bank and her wardrobe reflected her occupation: smart skirt suits, a few short dresses, some little, and black. An array of colourful blouses, and skirts of varying lengths, material, and colours.
We were similar enough in build that undergarments were never a problem as far as size went, and I preferred to wear the bras and pants that she’d worn languishing in the laundry basket.
Shoes however were a problem. My size seven feet could hobble about in my wife’s size five three-inch heeled sandals. (Always remembering to return the buckled strap back to her settings.) Over the years, I’d managed to strut with confidence around a lonely room but the call of the outdoors was always beckoning, and when the wife of a close friend was throwing out a pair of size seven, black velvet platform heeled boots, I knew they would be ideal for my purposes. I made up the excuse that the boots would be ideal for when I went on stage with the Glam Rock band that I was forming.
My opportunity arose when my wife went on a week’s course down in London. I dropped her off at the airport, and on my return journey home I planned my nighttime excursion.
The plan was to drive to the next village, park up, and walk along the main street.
I started getting ready around 8 pm. My entire body shook uncontrollably as I looked at my trousseau displayed on the bed. My close shave was hindered by my shaking hand as the razor attempted its thorough job on my face.
A couple of hours later, I stood before a full-length wardrobe door mirror, admiring my reflection. And there she was, looking back at me. Narcisstically I thought, “I’d do me!”
I’d done a good job on my shoulder-length hair and my face was definitely passable. My foraging in the laundry basket rewarded me with a white bra and pants, a pair of light tan tights and a white blouse. I’d always thought my wife looked great when she wore her black leather mini-skirt, and on me, it was even “minier”.
I painted my fingernails red, to match my lips, and clipped on a set of earrings.
My recently acquired knee-length black velvet boots completed my ensemble. I resisted the urge to “knock one off” right there and then, and selected a black leather blouson jacket from my wife’s wardrobe. I was ready. I scooped some stuff (hairbrush, lippy, wallet!) into a shiny black patent handbag.
From behind the living room curtain, I could see that my street was deserted, as it usually was, at 10 o’clock on a dull Monday night in October.
When I returned earlier, I had reversed the car into my garage, leaving the noisy large metal sliding door open, in readiness for a sharp exit. I left the house via the back door and ventured further than I’d boldly ventured before, en femme.
I entered through the garage’s back door and was soon sitting inside my Ford Capri. Minutes later I was just another lady driver, sticking to the speed limit as I drove out of town.
As I mentioned earlier, my destination was a small town about five miles/minutes away. The few oncoming vehicles that I did encounter drove past obliviously, their headlights briefly lighting up the inside of my car. I flicked down the sun visor to reveal the vanity mirror (never was an accessory better named), in order to see my face as they whizzed by. “I’d definitely do me!”
I parked up in a small side road just off the main High Street. I’m pleased to say that my etiquette when entering and exiting a vehicle has improved over the years. I locked the car just as the body tremors returned. I had not come this far to be put off by the shakes. I steadied myself by clinging on to the car door handle and took a few deep breaths. I would have taken a few more had it not been for the sudden appearance of an approaching figure. A portly bloke, probably in his sixties, and looking like he’d just left one of the four alehouses on the High Street. I crossed to the opposite pavement to avoid eye contact. Or God forbid… a “hello!”
Looking back, that guy was the first person to see me dressed! And he wasn’t to be the last. He gave me the once over, muttered something incoherently and continued on his way.
I continued to the corner of the main street and eyed up my options. To cross, or not to cross. I was looking for the quiet side of the street, and given that three of the pubs were on the same side I was on, and it was approaching closing time, I chose to cross.
The Monday night traffic was sporadic. A few cars passed in both directions and one appeared to slow down. It was travelling in my direction and I watched as the indicator flashed right, before turning into a side street. My heart was pumping as I continued to strut towards a brightly lit telephone kiosk on the other side of that sidestreet. I looked to see if the driver of the aforementioned vehicle was waiting to pounce. I suddenly felt vulnerable as an empathy towards women walking alone washed over me. All was quiet.
These were the days when mobile phones were a wonder of science fiction, so it would have been normal for someone to use a public phone box. Which I did. I entered the glass-panelled red box and simulated a telephone call, all the time watching for anything or anyone that would give cause for concern. It occurred to me that I was standing inside a goldfish bowl, and I could imagine the drivers of passing cars on witnessing the woman dressed in a leather mini-skirt and boots…
“She’s asking for it!” Which I was, up to a point.
I decided it was time to return to my vehicle, a couple of hundred yards away. So far I had got away with it. I had shown off my legs to a few motorists without incident. I hung up the receiver and set off back towards the sanctuary of my vehicle.
As a car approached in the distance, I decided to cross the street with the intention of the driver seeing me. He did, and smiled as I skipped onto the pavement. I smiled back. I looked over my shoulder and saw his brake lights light up.
“Oh fuck!”
I was now on the same side of the High Street as the three drinking establishments, one of which I had to pass.
“Nice pins.” A solitary guy in his mid-forties I guessed, exited the pub just as I passed. I did what every self-respecting gal would do, and ignored him.
Just as I was approaching my sidestreet, the vehicle with the smiling driver poked its nose out. He must have driven the back road and was coming round for another look at the girl in black leather. With the aid of the street lighting through his glass sunroof, I could see that he was around my age, with jet black hair and a black mouser moustache. He was only a few feet away as I passed by his passenger door. I avoided eye contact and continued the few yards to my vehicle.
My smiling admirer drove on to the High street, and for all I knew was parking up, or preparing to do another circuit to catch me at the other end of the road. I retrieved my key from my jacket pocket and opened my car door.
As I drove on my return journey home, I was already planning my next outing.
A few minutes later, I was soon back inside my house, and as always concluded my crossdressing session with some self-gratification. Okay! A wank. I fantasized about a guy with jet black hair and a mouser moustache.
Okay, not the most exciting read, but it was my first time out as Michelle, and I can assure you, as my confidence grew, so did the experiences. Especially after I met the gorgeous woman who was to become my second wife, who not only knew about my crossdressing before we were wed, she positively encouraged it.