Weekend at Diane's-Part I by Anna V. Hedge (avhedge@yahoo.com) Copyright 2005
You, Jim Tompson, had been working with Diane for just over 2 years. The official title of your job was "assistant" but everyone knew that it was just a fancy name for "secretary." Everyone in the office knew that you were the only male assistant although you enjoyed the conversations with the rest of the "assistants" by the coffee pot. Plus, you loved your job. The pay was good and working with Diane was great fun. Diane was a beautiful mid-30's year old senior executive at the company, which explains why she was able to pay you what she did. Besides being a great person to talk with, her fashion taste was wonderful thus allowing you to daydream about how her clothes would look on you.
Diane did not know that you had been a closeted crossdresser since you "borrowed" your mothers pantyhose back in 2nd grade. 20 years later your wardrobe had expanded exponentially, but even though you had thought about transitioning to living as a woman full time, the societal pressures were too much for you to actually do it. Even so, you had taken great pains to look as androgynous as possible; your body, except for your head, was perfectly shaved and moisturized; your hair was wonderfully kept in a pony tail and had several times started a conversation amongst the other "assistants" as to whether you had the best hair of the bunch of them; your eyebrows were smartly shaped so as to look feminine yet not too much as not to arise suspicions from the male section of society and your face grew no facial hair after several electrolysis sessions; and your body was kept in wonderful shape by a stringent diet and exercise regimen that accentuated all your feminine body parts without giving you bulk.
You had been wearing womanly clothing, in particular boy-short panties and pantyhose, to the office since about the first month you joined the company. There are just few things that are as enjoyable as the silky feeling of sheer hose and panties hugging your body all day long. For this Monday morning, you decided to stick solely to the micro-fiber stretchy bright pink boy-short panties accompanied with your recently done French-tip toe nails. On top of your attire you put on your drab suit, although at least you got to enjoy your freshly shaved legs rubbing against the soft cotton of your slacks.
The work day went by as usual, starting with a conversation over coffee first thing in the morning to establish Diane's schedule for the week. She showed up that morning wearing a stellar black-pinstriped suit, accompanied by killer pumps, a cream silk shirt, pearl necklace, and her hair and makeup done fashionably but without calling too much attention to herself. After setting up her schedule you talked about your respective weekends, with Diane mentioning she had gone out on a date on Saturday night that went, yet once more, horribly. You finished with a little company gossip and off you went. On the way out of her office, you caught your shoe on the edge of the Persian carpet adorning the floor and spilled the paperwork you were carrying. You bent over and picked the stash of papers, apologized for the mistake, and off you went.
Right about the time when you were about to take off for home, Diane asked you to go into her office. She had a funny look about herself, as if she was examining you, and then she asked you:
"I have a sort of personal question to ask you Jim, if you don't mind?"
Had it been anyone else I would have worried, but being Diane, and being it that we talked casually a lot, I replied:
"What's up?"
"So, when you dropped all those papers earlier today I noticed that you were...were...how should we say, wearing women's underpants..."
My faced turned bright red and I started to think of how to explain this. I could say I lost a bet to some friends this weekend or that I was just curious how they felt, but it was just the one time and...
"The thing is," she continued "I have noticed that you wearing panties a lot, and well I was wondering whether you could explain this to me?"
"Well...hmmm...I am not sure how to explain this."
"Look Jim, I am not mad. I have been thinking about asking you about it for a long time, but I just never got around to it."
With that, I told Diane my long-lasting relationship with women's clothing and even went as far as talking about my flirtations with a psychiatrist and the possibility of transitioning full time. As I ended she said:
"Well, I suspected that something similar to that was going on. I mean, you aren't exactly the manliest looking person around. I just had thought that you were a drag queen and were doing a show or something around town on weekends." She said with a smile.
Relieved I said: "No. Sorry. No show or drag queen thing."
"Well, I tell you what. Why don't you come over for dinner to my place on Saturday night? I sure could use a relaxing time with another girl."
Did she just ask me to come over for dinner dressed as Anna? "Well," I replied "I guess we could do that."
"That settles it then. 7:30 on Saturday it is."
The rest of the week went by in a flash. Between me thinking about how the Saturday night would turn out, what I should wear, and Diane dropping hints about my how good my ass would look in this and that as I was leaving her office, time flew by to the point where by the time I realized what was about to happen I was getting ready for dinner.
Saturday morning and afternoon I spent it in the bath, doing my nails and deciding what to wear. Diane had asked when the last time I had gone out as a girl was, and upon finding out it had been 2 years, suggested that I wear whatever I felt like wearing. She had even suggested me coming over to her place to get ready there, but I told her I would just dress up at home.
For the evening I ended up settling with a nice pair of matching pink, silk bra (pushup and padded) and boy-cut panties, tan-shear pantyhose, a flat black skirt that fell right above my knees, a tight short-sleeve t-shirt, and black Mary Janes. I had actually gone into a salon to have my nails done, so they were styling a beautiful French tip. The girls at the salon looked at me weird, but after I explained that I was going to some weird party, it seemed to help. I put on a pair of studs on each ear and a faux pearl necklace and a couple of silver rings for jewelry. My hair, medium length and dark brown, was accompanied by light foundation with a touch of light gray eye-shadow, mascara, blush and a deep purple lip-stick and lip liner.
I checked myself once more in the mirror, threw a couple of necessary items in my purse and off I went into the night. I felt a slightly cool breeze creep up my skirt, but the feeling of my thighs rubbing against each other accompanied by the hose made this whole experience worth it. As I hopped in the car I noticed a pair of guys walking by on their way to their apartment eyeing me. They looked more wanting than anything else, so I took it as a positive sign and with that I set off to Diane's.
The 45 minute drive went flawless except for me having to stop for gas and getting used to driving with heels. The guy at the pump opposite me kept staring at me, but nothing became of that. I parked by Diane's garage door, checked my hair and makeup once more, locked the car, and walked towards the entrance. As I hit the bell, I hear a pair of heels walking towards the door, followed by the turning of the doorknob, and the door opening.
As the inside of the house was revealed to myself, I noticed not only Diane holding the door with a huge smile and saying "Welcome," but also a group of 5 women from work standing in her living room all waiting for me.
To be continued....