I had come home to find my girlfriend of 2 years packing her suitcases. She looked up at me and said “Sorry. I left you a letter. It is better this way No Fuss No Muss. “
She had some auditions lined up in LA. She would send me an email with her address once she got her place. So that was that then. About a week went by; it was a Friday night. Work had sucked all week. I came home with a bottle of cheap vodka and some cranberry juice and started drinking. Sometime in the evening, I had begun to throw out things from the closet. When I got to the set of baskets on my ex’s side, I discovered a stash of her underwear, shoes, and some dresses folded up in bags. In the chest of drawers, there was more of her stuff. I threw most of it on the bed in the spare room. I went into the en-suite and found a bunch of cosmetics and hair products. They too went on the couch. I slugged back another vodka and went out around the block, for Vietnamese food.
Another week went by, and work seemed to suck even more. My boss was inept, he could not read the financial statements I presented. The HR manager was always asking me questions about our mainly female office staff. I hated my Job. I went home with some Vodka, didn’t need the Cranberry Juice. Sometime on Saturday morning, I woke up in my spare room, naked, hungover, surrounded by outfits I had put together from the abandoned clothing I had dumped in there. I was a closet cross-dresser, which I had suppressed for years, along with my bi-sexual tendencies. What can I say liked women, but I also loved men, and the thought of a man or men doing things to me was a pretty much recurring masturbation fantasy. I stood looking at the outfits, and my resolve crumbled. I tried on a pair of boy shorts and a tight sports bra. Some gel in my hair and I had an androgynous look. Pulled on some Nike leggings, a white sports T and the look was complete. No DPL on my ass, which shaped right up, some white ankle socks and a pair of Nike trainers, all set. Took the wind shell and fixed my too long hair under a Pink ball cap I rooted around in the cosmetics mess and found a pink lip gloss. I walked around the apartment. The reflections in the windows screamed woman. Did I confess I have been crossdressing on and off since I was 12? Many purges, many self-recriminations. Screw it; I had to try. I grabbed my keys, and phone, down the elevator, and ran slash walked to the park. I was out of shape. I managed just over a mile running; then I walked for an hour. No One called me out, a couple of guys whistled. I went home with a smile.
For a couple of months, I kept it up, I stopped the Junk food, ate more veggies, and worked on getting my make up right. So here I am five feet seven. 133 lbs, size seven shoes, dressed in a bra rolling stockings up my hairless legs. Garter belt on, then the thong. With a little effort, I pushed my balls up inside me, pushed my limp penis back and tucked it all away. I had to wear silicone inserts to get my breasts to look right; I had got to the point where I could fake cleavage. The skirt was a petticoat with four layers of tulle, a white silk chemise covered by a tight v neck sweater in pink. I slipped on some 3” heels with a strap, an off-white Pashmina over my shoulders, grabbed my clutch and I walked to the door, and I was ready. A pause and I looked in the hall mirror. There were traces of me there, reflected back was a woman. This was a big deal, I was going out to an LGBTQ friendly bar, with a friend. A new friend, a girl like me who I had met at the cosmetics counter. She had given me a few makeovers and lots of advice; tonight, was a coming out of sorts. It was Friday night, and I was going to my first girl’s night out.
The club was busy, Cassie dragged me in, to meet her friends. They had a booth in the back. No sooner than I had sat down, I was introduced and listened to the gossip. It seemed that Cassie and I had hit the genetic jackpot, we could pass as women. Brenda was a drag Queen, Betty was very Butch, and working on her look. Caroline was a boy in a dress and didn’t care. All in all, a good bunch.
A few drinks later and more than a few dances I had sat down at the now empty booth for a rest. Suddenly a glass appeared before me, from the Bar, the waitress said. I sipped it and looked around, no one I knew. The third Martini was a bit too much. I grabbed my clutch and went to the washroom. On the way back, I felt the drinks kick in. As I half fell and stumbled a massive pair of hands caught me and all I could see were these striking green eyes. I was led to a side table and carefully sat. The Man was massive, he bought club soda, and suggested I drink it. When I felt semi-normal the man stood and offered me a hand, we danced for what seemed like hours. I know he kissed me a few times. He took my hand and led me back to my friends. He bought a round for the table and left; it was only later I found his card in my clutch.
Two weeks later, a Saturday morning, I was lounging around in some silk Pj’s, my hair pulled back in a ponytail. Lazy morning, reading my tablet. HR had told me I had to use my accumulated vacation, or I might lose it. I had done all my chores, so it was all me time. My mobile phone rings, I just picked it up and for some reason said: “Angie speaking.” It was Mr. Green eyes.
“Good Morning, sorry for the intrusion, I just felt I needed to check in on you.
“Um thank you, just lounging around.” I smiled, how cute.
“Its still early but I was wondering If I could take you out for dinner tomorrow night,”
Didn’t see this coming at all.
“That sounds fun, get all dressed up and take me to the Country club?” there was silence.
“Well, I was thinking of more along the lines of one of the fish places downtown, or that new restaurant on the North Shore. Sorry, this comes off cold, I haven’t dated for a while.”
I coughed, “Um truth time here, this sounds amazing, just one detail, you do know I am a male, who cross-dresses as a woman?”
There was a pause, a slight cough “yes that’s why I called you, first you can pull it off, and second, I want to get to know you. So why don’t you get all ready to go, and I’ll be round in say 3 hours, and we can go finds a lunch spot, and get better acquainted?”
“Well, I like a man who takes charge, Frank, so 3 hours it is. Do you have a pen, I’ll give you my address?”
Where does the time go? I had a second shower, ran some dry shampoo thru my hair, and brushed it out. It worked, and my hair fell below my shoulders. I found a cute black bra, the nude inserts, instant cleavage. My penis was tucked and locked in with a latex gaffe; then I rolled on the Spanx mid-thigh pantie that also boosted my booty, the Spanx Cami held me all in. In the spare room, I put on a black silk T-Shirt then pulled a grey, black silk and merino hoodie over it. I rolled on some washed out skinny blue jeans. Thank God, I had been dieting, the jeans were tight, but I fit them. I pulled on my black leather wedge boots and grabbed the matching purse. With my summer tan, i could get away with makeup minimal makeup, a little contouring, some grey eyeshadow, and nude lipstick, followed by a spray of Lancôme Climat. I slipped the silver studs out of my ears and put in some small silver hoops. I grabbed my chunky emerald ring for my right hand and just four silver bangles for my left wrist. I still had my Rolex on my left wrist. I stopped for a second and took a deep breath. As I stood in the hallway, I noticed the painted nails on my hand, the perfect red, setting off my tan, and the dark top. I had done them this morning, just for fun. I shook my head and smiled, picked up a grey pashmina found my clutch, cash, and phone, tissues, and lipstick, all in the bag. Just as I walked to the door, the cell rang,
“Hi, I’m early I’m just pulling in.”
“I’ll be right out.”