A Year Ago Ch. 01

I started on this path about a year ago. I was working on my laptop and mistakenly entered a site showing a group of images of beautiful girls, many nearly naked. The images of the girls were all sexy though each was dressed in a bit of lingerie. My scroll went passed over thirty beautiful girls when I stopped. The image of the woman I stared at was different, and due to something a bit odd, arousing. The next image was of two women, a lovely lady with another girl, both with long dirty blonde hair and their legs covered in creamy colored hose held by suspender clasps. The lady was atop the other and the photograph was shot of their bottoms. It wasn't that the lighting or mood of the image was off. It was that the girl on top had a rigid penis and a tight groin, seemingly without testes. I returned to the first image and realized it was a picture of the 'girl' atop the other. This image showed the girl's face, and her body though covered by a lacy chemise was apparent. Her head was slightly turned toward camera, a gorgeous beauty with a smile, her breasts shown in profile.

This idea wasn't foreign to me. I had a college friend who I'd encountered while he was dressed as a girl. At the time I considered the effort Stan put into her outfit as pretty amazing. Her look was convincing, but I just knew it was Stan, only in a dress. But the image in front of me was not leaving me. I thought while I continued to look.

I was finding success with my for fee Malware on-line service. I'd quit my job awhile back to run the systems I created as a business. It was a gamble to leave a good position with salary and benefits and now the site was growing and providing me as a sole owner with more income than I could spend. To my mind I just wouldn't do anything less than at the best effort I possibly could. The work was straightforward now that the systems were coordinated. The time I needed to keep it up was increasingly smaller. It was the accounting; the tracking of clients and payments, resolving difficulties the users encountered that took most of my time. Yet I wasn't busy. Now I was daydreaming, the image of the two women now back on the screen.

I needed something new in my life. I had lived with my girlfriend Lynn for 4 months when she'd suggested I wasn't marrying material. Lynn felt I was bit too focused on my own needs and less interested her fulfillment. The development of the site had consumed so many hours and weeks. At the time this had hurt me but I found she was right in many ways. She'd left me less than a month after I'd quit my position. Nine weeks later I had setup the office for the site at a nearby second floor rental over a Copy Center and things were looking up.

I was quite stimulated by the image of the girls. Not in a sexual way, but it had raised my curiosity. I left my desk, the image still on the screen and went to the bath mirror. Lynn had once said it was tough being with such a 'pretty' man. She wasn't picking on my masculinity, her intent was more about how I looked. Looking at my face I now wondered again what she'd meant. That evening months ago we'd been out with three of her college friends when Cynthia had said something at the Bar.

"Lynn, Michael is so beautiful you could almost call him Michelle." Lynn just turned to look away, passed me, rather than commenting.

I knew I wasn't a hunky guy, but now I considered Cynthia's barb. I pushed my mop of blonde hair back to see all of my face. Then I decided to head to the store. I needed some supplies before I could be certain. Like most things I did I was focused at solving a problem. Today I had nothing on the agenda so I started the old Audi and turned left.

I entered the DrugFair looking about and noticed the cosmetics immediately on the right. Pausing in front of the array of products I thought about the list I read on line. I needed a moisturizer, a bottle of makeup base and mineral powder, an eye color kit, two different mascara products, some blush, three lip-glosses in different tones and a brush kit. I glimpsed a saleswoman coming near; slightly panicked I stood still, head down. She was near me and could see the stuff in my little basket.

"Can I suggest you consider an eyeliner, maybe also a lip liner young man? I think you'll need tweezers to help with those brows as well."

Her comments were sort of helpful but I was nervous. She had read my plan. My blush must have been apparent as I turned to leave, but I stopped. What was I doing? I paused to think, "Any other ideas?"

She was a bit over fifty but pleasant looking and fit. She had been re-stocking an opposite lower shelf. She stood and reached to my shoulder, "Humm, turn into the light."

She moved me about lightly, "You've got a lovely face, great cheeks and skin. Your eyes are your asset. You should get a better grade of eye makeup. Try the L'Oreal set instead. They make a good concealer, here, this one."

I quickly left the store, a bit embarrassed but also surprised that she saw something.

She'd said, "You're going to be beautiful, come back later and show me, ok?" Her tag read Esther.

I realized as a drove home I needed some guidance. YouTube was very helpful. After I'd washed my face i pulled my hair back with my sweatband. Twenty minutes later I was done, well my face was made up but I wasn't happy. I cleaned my face and started over. Two hours and six applications later I had learned the basics and found some color tones I felt helped my look. I was focused, and it was a bit more fun than I thought. I tried to simplify the sequence to minimize the intensity. The results were intriguing. I need to carry this experiment a little further. It was just after Noon when I called a nearby salon.

"Can you fit me in for a styling and coloring?"

After a review of my head the Hairdresser said she would do an andro style, "Think Cara Delevingne but with short hair." The idea I would look like that beautiful model was preposterous.

Around 3pm I returned to the DrugFair and found Esther working in the toy section.

"Excuse me Ma'am, can you show me where the hair products are?" I stood still as she continued to stack the crayons in the children's toy aisle.

Without looking up she said, "Two aisles to the right."

I didn't move and a moment later she turned, "Did you hear me young lady?"

Now she stood and her face showed more than a little surprise, "I'd say you've changed a little," she came to my side and again reached to turn me into the light. "Who did your hair? It's perfect now."

"These are our best line of products for shorter styles Ms," the cute high school girl working the register said.

I left the store with a smile on my face. As I left another man stopped at the door and did a double take. I wondered what the next step would be. Six hours after I'd got this crazy desire I was moving about the world in my jeans and sneakers, a soft gray sweater without a tee shirt, but people weren't questioning my gender. I wouldn't say I looked like a tomboy, more of a relaxed college student.

The stylist had given me some direction. "Until your hair reaches the top of your shoulders you can get by with the generic hair care from your local store. The risk is yours. I'd start using the Aveda line so as it grows out it stays beautiful."

But that stuff was way expensive, twenty-seven dollars for rinse and shampoo? And I needed 'beautiful hair'?

Last year my workout regiment was altered due to a severe muscle injury. Only able to handle low impact drills I had resorted to a new focus on eating nutritional foods that limited my weight gain. Now a year later I had slipped below 135 pounds, eight of those since Lynn moved out, though I was over 68 inches tall. I'd lost over twenty pounds of body fat. Walking aggressively had become my favorite exercise since I found my muscles were better balanced.

When I returned to the house I went to the CPU and started to review different women's clothing sites. After twenty minutes I realized the effort was a waste of time. Boston Proper and VS didn't seem right. I decided to visit Nordstrom. They seemed to have a range for many styles.

Back in the Audi I turned right, 30 minutes later I was in the parking lot. Due to the late afternoon I found a spot near the entrance and quickly I was cautiously reviewing the women's suits. A saleswoman approached. I was still dressed in my Hugo jeans and black sneakers.

"It's a great time to shop, huh? Are you looking for a suit Miss?" I turned toward her voice; she was a good-looking woman about 28 years old, wearing a skirt and blouse. I realized how difficult this was about to become. The hair stylist was curious but didn't pause over my slightly modified male voice. I had gotten away with a near whisper.

"Ahh, I'm just getting started, and I'm a little unsure, Miss . . ." my voice didn't break but sounded a little higher, not too contrived, almost feminine.

She smiled and extended her hand, "Don't worry about a thing, I understand and can be helpful with your search. At this dull hour you've got me as a personal assistant. I'm Cheryl."

I looked into her eyes and relaxed, she hadn't noticed my gender shift. My face was smooth, I needed to shave only every other day, and my face looked pretty good. "I'm Hallie, and I could use a ton of help Cheryl."

I didn't really need a business suit but we started with a well-made, great fitting suit. Cheryl had me visit the tailor and the older woman handled the subtle adjustments. I hadn't shaved my legs since my last cycling club-ride four weeks ago, but I wasn't a hairy guy.

"This is a good fit but I suggest we adjust the hem about a inch, say to here?"

She also adjusted the waist, "You're pretty slim, but your hips are 37 inches. Do you diet or are you normally thin?" The tailor adjusted the fit of the jacket as well.

"The cut helps define you. You have a small chest."

Cheryl returned and she suggested we try some jeans and tops, "I can help you with two or three casual looks Hallie. This pair will accentuate your hips and butt. You know what though, you're in need of some help up top. What size bra are you?"

I was now anxious, "I'm not wearing one, umm, I'm pretty flat Cheryl," she looked at me with a curious expression.

"So Hallie, we need to help you with that ok?"

An hour later I left the fitting room with a special set of small breast forms and a collection of three bras. I left the store still unsure whether Cheryl knew I wasn't a girl. I decided to complete my shopping at the other stores in the adjacent Mall. Though I saw many interesting outfits I just didn't have a clue about my style, and the sizing required a lot of guessing. Returning to the Nordstrom I found Cheryl. She was folding some sweater tops as I approached.

"I can't do this on my own. Can you help me? I am clueless about my sizing, and how to select the appropriate style." She smiled and looked a bit closer.

"Can I ask you a personal question Hallie? I mean I could see you were at a bit of a loss when we selected the suit and the jeans."

I shook my head and looked down to my sneakers. "What woman would go shopping in these shoes, huh?"

"Well, that's correct but it isn't what I was going to ask. I mean, yes those are horrible for trying on clothes. But I was going to ask if you've ever modeled. Your figure is close to perfect and you have a slightly androgynous look. You remind me of someone, recently but from Europe. I recall now, a Brit model named Sarah Whale. Sure you're a bit shorter but you could go with that minimal, not quite girl look."

I just stood there. This lovely girly girl was advising me to look a bit more like a boy. This stirred a thought. Maybe that was what Cynthia was pushing at Lynn. Were she and Cynthia lovers? This thought distracted me for a moment and I had to ask Cheryl, "Excuse me, what did you say?"

"Only that a great pair of heels is the next stop. Come with me Hallie."

Around 8pm I returned home with four large bags. I had bought twenty-one hundred dollars' worth of clothes and some accessories. The four pairs of shoes weren't all tall heels and I had, with Cheryl's help picked three skirts, several tops and two lovely dresses. I was too tried to get more than the simplest of underwear; a packages of bikinis and some thongs, costing less than a twenty. Cheryl had said the outfits would require a concealed look; no panty line as she called it.

I'd worn one of the bras and the silicone enhancers to get the dresses to fit correctly and though reasonably comfortable I want to take it off. I passed the tall mirror in the Hall and saw the new vision Cheryl had helped put together, 'wear this outfit home Hallie'.

I had on a low black slingback heel, a bit more than 2" high, setting off the long leg, nearly black pants with the tight fit across my butt. These were tailored to express my ass cleft. My top was a soft pale white cashmere top without a chemise. The fake tities help create a bit of cleavage accented by the simple single pearl necklace and hoop earring now hanging from my ears. I could see the pink strap of my bra due to wide V neckline of the top. My hair looking amazing since I could, with ten minutes and the right tools, get it back to a boyish style.

I had left the house at 7am as a twenty-six year old man and returned hours later as nearly a girl as could possibly be. There was something 'virtual' about me but mostly it was me, re-imagined, but still me. Could I commit to these changes?

I stared at the image in the mirror of myself for a few minutes. Since then I have been driven to change my existence.

The End of the 1st Phase