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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 own place. In some ways I was glad, we had drifted apart. I worked too much; she went to auditions. I had done all I could to make it work and failed. So that was that then.
A week went by, it was a Friday night, again. 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 started to throw out things from the closet. When I got to my ex girlfriends side, I discovered a stash of her underwear, shoes, 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 spare bed. Standing looking at the mess, I slugged back another vodka and went out around the block to the local Vietnamese restaurant.
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 female office staff. I hated my Job.
I went home with some Vodka, didn’t need the Cranberry Juice. Saturday morning, I woke up in my spare room. Naked, hungover, I stood up and looked at the outfits I had put together from the clothing dumped in there. I am a closet cross-dresser, which I had suppressed for years. What can I say liked women, I also loved men. 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 a tight sports bra, adding some silicone inserts and jiggling till it looked right. Some gel in my hair and I had an androgynous look. Pulled on some Yoga pants and a tight white 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 short 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 cross dressing 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 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. 139 lbs, size 7 shoes dressed in bra rolling stockings up my hairless legs. Garter belt on, then the thong. With a little effort, I pushed my balls up inside me, rolled the penis back and tucked it all away. I had to wear the 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. The outfit needed something else, I took an off-white Pashmina for over my shoulders, grabbed my clutch and I walked to the door, I was ready. A pause and I looked in the hall mirror. There were traces of me there, but what looked back was a woman. This was a big deal, I was going out to an LGBT friendly bar, with a friend. A new friend, a girl like me who Itook had met at the cosmetics counter. She worked the counter and 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. A drink appeared before me, from the Bar, the waitress said. I sipped it, and looked around, no one I knew. The third drink was a bit too much. I grabbed my clutch and went to the washroom. On the way back, I felt the booze kick in. As I half fell and stumbled a huge pair of hands caught me and all I could see were these striking green eyes. Strong hands led me to a booth and sat me down. The Man was huge, he brought 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.
A week Friday morning, I was lounging around in some silk Pj’s, my hair pulled back in a ponytail. Lazy morning, reading on my tablet. HR had told me I had to use my accumulated vacation, or lose it. I had done all my chores, so it was all me time. My mobile phone rings, I picked it up and for some reason said: “Angie speaking.” It was Mr. Green eyes.
“Good Morning, sorry for the intrusion, I felt I needed to check in on you.
“Um thank you, lounging around.” I smiled, how cute.
“Its still early but I called to see if I could take you out for a late lunch today”
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 like one of the fish places downtown, or that new bistro 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, 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 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 clean black bra, the nude inserts, instant cleavage. I tucked my penis a latex gaffe kept it all hidden. I rolled on the Spanx mid thigh pantie, that also boosted my booty, the spandex 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. Makeup was minimal, some grey eye-shadow, and a 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 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 of my tan, and the dark top. I had done them this morning, 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. As I walked to the door, the cell rang,
“Hi, I’m early I’m pulling up.”
“I’ll be right out.” I picked up my dark sunglasses with the full frames, and walked to the door.
Mr. Green eyes was standing, by his car, what a car, Audi Coupe TT.
“Hi, Frank, nice to see you. Close your mouth, Its fly season.”
“Angie you look amazing, stunning, here let me get the door.”
What a nice man, I was getting a little horny, the Spanx was helping.
“So, Frank, do I pass muster?”
Frank was struggling to keep his eyes on the road. He had a smile though, “Yes Angela, you more than pass. You look fantastic.”
The restaurant was an upscale bistro, and of course, we had to run into a friend of Franks. Something in my head clicked, I ran my arm through Frank, as the stranger approached. I was introduced to Harold. All a bit formal, all a bit stiff.
As we walked to our table, I noticed Harold, was on his phone.
Frank, sat back and looked around, I could see myself in the mirror behind him, all I saw was a stunning woman.
Frank, suggested some choices, I ordered a wine and once our drinks served Frank leaned in. The table was at the end, so little chance of anyone overhearing us.
“So this is fun, I know I am a little stiff, I am out of practice, I have thought a lot about you since that night. Tell me something about you?”
I smiled, wiped my lips on the linen napkin and leaned in. “What you see is what you get. I work for the local municipal government, in finance. I’m a single child; both parents are gone. I own my house; I am single. The cross-dressing genie only escaped some months ago after my ex took off. She left some clothes behind,this outfit is all my own. ”
I sipped the wine. Frank looked over to the door then spoke. “I run the family business, Westerly Yards, and my own concern, Hansen Overseas.”
I sat back; this was huge, the Westerly family was serious old money. Cattle, mining, shipping, huge
“Frank, weren’t you married not that long ago?”
Frank coughed, ” It was arranged, yes that happens, she left me after two years, took off with her high school sweetheart. The prenup was ironclad, she got a cheque last month, and I am free. That’s why I was out with some friends celebrating, I got separated from them and ended up in your club. Saw you and was smitten. Truth is I love men and women; please do not take this the wrong way I prefer girls like you.”
I was wringing the napkin, and I know I blushed when there was a shout from the front of the restaurant. I ignored it; Frank had half stood, when two couples were upon us. Introductions were made, and they decided to join us. I was in stealth mode and made small talk. Before I could say too much, Frank jumped in. “Angela, is an accountant, we worked on a project, she saw some things, that my people missed. She is brilliant with numbers. We got to be more than work partners
All I could think was take a breath, and who was this guy, he must have checked me out somehow, with all his money that made sense. The rest of the afternoon was a blur. I know I was too quiet, and I drank a little too much. I wasn’t making a fool of my self. I managed to drink some club soda. The friends were all part of the rich set, no question.
Source: reddit.com/r/Erotica/comments/ad8b78/behind_the_blinds