Sissy’s Debut -- Pt 5

Maid Joy

I had finally decided to focus on some sort of administrative MOS. While filing and forms were a part of what I did now, there were a lot of other things that you needed to know to survive in an office situation.

I felt like a living cliché. A man who wants to be a woman, joined the Army, now studying to be a secretary. Yeah, puts a whole different spin on the “office couch.”

Reading over the regulations for the Admin MOSes, I found most of them required typing skills. I pulled out a laptop that I had received several months ago (a Christmas present from my mother). I did some web searches for typing tutorials and practice and time tests and so on. I decided to devote two hours every day to just practicing typing.

I soon found out that it was much harder to type on the laptop keyboard than on a normal keyboard. So I resolved to get a full sized keyboard and mouse to hook into the laptop for practice later.

I bookmarked those pages and started looking around the Internet. I knew that a lot of the traffic would be monitored by the Spooks, but I didn’t care. It was highly unlikely that the sites I was going to would be questionable. No one would object to a macho guy looking at pictures of girls in bikinis or in really cute outfits. Most of the porn sites were blocked, but catalogs and so on weren’t.

In the process of looking around, I found a lot of stories online. Stories about guys like me who wanted to be girls and more. I copied a lot of URLs into shortcuts and finally encrypted them all so that if my computer was searched, they wouldn’t be found. Renaming the resulting encrypted file and changing the extension so that it looked like a system file, further disguised it.

It might seem that I was being paranoid, but honestly, my big fear was being discovered having an interest in transsexuals and being ostracized by everyone I knew. I had heard of others who had been discovered to have interests that weren’t considered Army “normal”. Their lives were made a living hell until they were kicked out or forced to resign.

The way things were going, it appeared that I would be leaving the Army after all.

***

Karen had finished up with a session and decided to relax for a bit. She couldn’t wait for Sissy to come back. She wanted Sissy to shine her boots to that eye blinding shine that must be some sort of Army secret.

She made some plans to go shopping tomorrow so that she could see the kinds of things that Sissy would look good in. There had been several emails exchanged, mostly talking about fashions and things that Sissy liked.

Some were totally inappropriate. No matter how much padding she had on, she would not look good in a denim miniskirt and midriff top. There were other things that would cause problems, mostly because of the maturity factor. Club gear may be nice and look good on her, but when added to her body style now it would look like an old hooker trying to look 13.

Then there was starlet fashion. Lord have mercy, but Sissy had some very skewed ideas of appropriate clothes. At least she didn’t want to look like a supermodel, but gowns that would ordinarily be seen on the red carpet for the Oscars wouldn’t really look good on Sissy either — she just didn’t have the boobage to carry it.

Other than those fashion crimes it was surprising that Sissy had such a good taste. It was probably going to take a weekend to show her the proper way to express that style. Classic lines, conservative, earth tones with jewel accents would be really nice on her.

She took her boots off and loosened her corset until it was comfortable, and started making notes for the next weekend Sissy was available.

***

“Today we are going to go shopping. I have a pretty good idea as to what will look good on you, but now we actually have to buy things.”

She had me wear a nice dress that would be appropriate for anything from a high tea to a garden party. The blouse was kind of mannish, but the large sleeves and the full cut down to the wrists covered everything. She had me shave the area from about mid chest up to my neck; no one needs hair there.

Foundation garments came next. There was a padded girdle to actually gave me shape, along with a corset that made the lines smooth, the cups on the corset made it look like I had breasts instead of pectorals.

Now, don’t get me wrong, I was very proud of how my body looked. I had spent a lot of time developing and training it so that I could do what I needed and wanted it to do. I liked the way sweat felt after exertion and the knowledge that it was clean sweat. A real guy thing, I know.

She was suggesting that we go out to get clothes for me while I was in drag. If she hadn’t ordered it I never would have done it.

She showed me the way to pull opaque tights up my legs to cover the hair on my legs. Actually, we had to pull on three pairs so that it was smooth and fashionable. A tea length skirt with a nice half-slip completed the ensemble. She placed a pair of three inch heels on the floor for me to step into.

Makeup, wig, hair styling, earrings, necklaces (one just a simple chain and the other a heavier chain with a locket), three rings (all nice and sparkly), and finally bracelets and a watch. She pulled out a beautiful belt that was made of golden discs, laying like they were scales. She expanded it and put it around my waist, making sure that it was centered.

“Perfume and a purse is all that’s left. Any preference to the scent you will soon have on?” She handed me a couple bottles of perfume for me to smell. I recognized some names, but I had no clue what they were. Finally I found a scent that was nice and what I thought would be nice with my own scent. It was labeled “Shalimar Light”, and it had a nice jasmine scent. I loved it.

She sprayed a bit in the air and had me step into the mist. It drifted down over me and I felt so girly now.

I found that I had goose bumps.

Mistress pulled the contents of my pockets out and put them in a purse that matched the shoes and the skirt. My wallet, money, cell phone and the all-important pager were deposited into the ultimate symbol of womanhood. Mistress then proceeded to grab a few cosmetics and put them into the purse as well.

“Ready to make your debut? From here on out, there’s no hiding anymore. I’ll let you get away with not dressing up a for long periods of time, but from here on out, you are a woman.” Her eyes were misty. She took my hand. “Come on Sissy. We are going to outfit you from top to bottom.”

She walked out the door with her purse, still holding my hand. I had no choice but to follow her.

***

When we got to the mall and I felt like a whole butterfly convention had taken up residence in my guts. Nervous didn’t begin to describe how I felt. Terror on a scale that I had never felt before would be closer.

I was terrified of the ridicule from people who saw me. I didn’t feel that I could ever pass for a girl, and having others make fun of me for that was the worst thing in the world.

But Mistress dragged me into the Mall, and I didn’t have much choice. I was hyper aware. It was worse than the first time we did Night Ops. It felt as though my skin had been sanded. It seemed I could feel not only people looking at me, but their emotions and their very breath.

It was almost an out of body experience.

I didn’t look at anyone in particular, and I had to fight to keep my gaze up and in front of me, but I could see people around me looking at us. There were many who looked directly at me while passing, and there were others who looked at Mistress.

I could hear my heart in my ears. If I held my hand out, it would be shaking like an Aspen Leaf in a high wind.

There were some who looked at me and had an appraising look, and they were the girls. I can understand that, they were comparing me to them. Honestly, I was doing that as well. It didn’t matter that they were genetic girls, I was still doing this anyhow.

Then there were the men. Most of them just looked at me and kept looking, up and down my body, boobs and legs, sometimes the ass. Their eyes felt like their grubby hands groping me. It was not a sensation I enjoyed.

I wondered idly if this is what other girls felt like when I looked at them. If so, I would have to think about how I related to them in the future. That’s probably one reason that I couldn’t keep a girl.

Then there were others. One or two of the people looking at me would look at me, then do a double take, then smile and go back to what they were doing. It happened too many times to be coincidence. My heart plummeted into my shoes. I don’t remember much of the shopping trip. There were highlights, but most of it was a dizzying montage of me trying on various clothes, changing, shoes, purses and dresses.

***

Dragging Sissy out into the world was relatively easy, she wanted to be seen. Just like any other girl that I knew, she wanted attention. I honestly thought I would have to fight her more.

I kept a stream of chatter going so she was distracted from what was happening. I didn’t count on her ability to multi-task however. I tried to retrieve her attention, but it wasn’t any good. She was much better at surveillance than I was.

I saw her chin come up as she noticed people looking at her and noticing an attractive girl. But I also saw those who made her. It made my heart sink, but it was something that she would have to deal with.

I kept her going and kept her attention on me.

The nearest store was the Victoria’s Secret. I knew a couple people in here and their discretion could be counted on no matter what.

I spotted one as I came in. “Jamie, I need your help. This is Sissy and we need to get her everything.”

Jamie came over and quickly appraised Sissy. I knew that she probably spotted Sissy’s genetic sex, and that didn’t faze her at all. She smiled and took Sissy by the hand.

“Sissy, it’s wonderful to meet you. You and I have a lot in common already and I’ll be more than pleased to help you today.”

I knew that Sissy was in good hands now.