A Year Ago Ch. 02

This is an evolving story of sensual investigation. Please review the first Phase...

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I awoke the next morning around 7am and lying in bed considered yesterday's events. Before bed I wandered the Web reviewing the blog, chat and discussion sites where dressing was prominent. I was shocked how many of the people posted images of themselves, many too raunchy for my taste. I didn't feel I was alone with the new interest, just not quite as off as some. Could this become more than a casual sideline for me? There seemed to be a great number of males involved with acting out their desires. I was more than a little committed with dressing having spent nearly $2,400 dollars on the styling and clothes.

The alternative sites where the 'girls' seemed to respect themselves and women in general were less common. The ribald seemed to dominate the imaginations of most. I figured I was like most, trying at an illusion. I wondered if I could step further. Was this dressing a bit freaky or was there something deeper driving my interest? Could I enjoy living as a woman? Then I realized I wasn't done shopping. Cheryl had mentioned hose but I had distracted her with a question regarding my 4" heels and we hadn't completed the selection. I ran my hand over the stubble growing on my legs. I couldn't go out without some pantyhose. I decided to shave my legs.

After my shower I was applying some lipstick when I realized that I needed to shave my face as well. Going out with lipstick and an apparent beard would be a circus act. I would need to develop a new morning regiment. That is, if I intended to actually be presentable during the workday, but for who? I rarely had visitors and infrequently went out during the day. But right now I needed some pantyhose so I got in the Audi.

Back at the DrugFair I found a rack with the L'eggs, but which ones? What was a medium, and was I in need of support? Not wanting to not run into Esther I was nervous, but I lingered trying to review the packages. I then panicked, grabbed two Silken Mists, nude and suntan large, and moved to the checkout. It was early and the store was quiet as I exited. Once back in the car I realized there was no reason to run out. I looked ok; a woman out for an early errand before work.

Returning home I spent sometime deciding which dress to wear today. Selecting the outfit took more time than I'd considered. I put on a new bra with the falsies and a bikini, slipped the dress over my head and re-settled and styled my hair. With the light make up my face was not right, but the problem was not mascara or blush. The dress looked terrible. It was bunched up around my hips. My legs looked great in the simple hose and the medium heels. I realized I didn't have a slip. I pulled the material a bit to get it to look ok, but I'd need some other garments. I fixed my face and grabbed my cooling coffee and started the cpu.

I discovered two on-line sites offering a range of products, lingerie and stocking, one with free shipping. The search didn't end with pantyhose. Soon I was in full lingerie mode and stopped. Was I ready to begin a 'collection'? The cart had over fifteen items; hose, panties, three slips or what were called chemises, and one delicate set including a suspender, bra and thong. The pause allowed me to review another page, shapewear. I was carrying some weight in my tummy, maybe this waist cincher would be necessary. The images showed a good result and now the cart had over twenty items, since I added several more suspenders and stockings.

I'd planned to work from home today and just await the Brown truck delivery tomorrow. Just stay quiet and see how things went. I needn't worry about anything; I was trying to see if I could adjust to the affect the new clothes caused. I looked at my fingers. The nails needed attention, either as I typically maintained them, or as a woman would. I didn't have a nail file but in my tool kit there was one that might work. Being careful I shaped the 1/8" long ends and softened the edges. I didn't have a polish; again to the DrugFair?

The next afternoon I enjoyed opening all of the fine garments and revising my drawer layout. Shifting the stuff was easy, but organizing the garments was new to me. The top was now for my girl stuff. I quickly removed my tight low-rise bootcut jeans and the red top and slipped the nude tone satin chemise on. Opening one of the Wolford packages of hose to discover an error. The package had the sheer hose I ordered but also a pair of nude suspender pantyhose. It took a few minutes to figure how to get the unusual hose on. I now put on my dress from yesterday and it hung perfectly. A call interrupted my investigations and I didn't get all of the items unpacked until the evening. I wondered if I could now safely venture out in a dress.

After completing my work agenda for the day I returned to the bedroom and the new garments. As I unwrapped each item I became more aware how I was consciously changing myself. Each walk past the mirror stirred my realization that I'd spent most of the day in heels and a dress. Having a face on was causing a distraction; there was a girl, I mean a young lady in my home. But I was still a rough guy in a dress, moving about, a bit of a klutz, rather than a woman. This thought caused me to pause. A woman moves more carefully about the world. I could get along just as I was, but I considered the alternatives. Dressing was only part of this experiment. I'd convinced myself that my voice wasn't an issue. Being bruised was one thing, tearing an $18 dollar pair of tights was another matter; a found the term was 'ladder'. I needed more than a blouse and falsies to become what I seemed to desire.

I stepped back to the room I used as an office and spent a thirty minutes checking out a site focused on female expression and deportment. I'd also reviewed a Website video suggesting how a woman should walk in heels. With the simple suggestions I practiced around the house, sitting, standing and walking. The mirror helped me see how my subtle movements were so off base. After an hour I sat down and considered my next move.

I wanted to enjoy the evening weather so considered my options. Maybe a stop at the new wine bar down in the Village center might give me some confidence in my appearance and manner. After an hour the mirror just was too biased. There was a little risk, someone might see through the disguise. I grabbed my wallet, ahh. Now I needed another accessory. I could stop at a nearby luggage shop before the bar.

I loved the new silky hose on my shaved legs but the suspender was going to take time to adjust to. Each shorten step in my black pumps reminded me that I was wear stockings, somewhat distracting, yet nice as well. I'd pushed my makeup to slightly deeper tones and hoped I didn't look over the top. This was much more effort than I thought previously. I had donned the earrings and necklace to finish my look. I probably would buy some other jewelry soon.

The lady at the bag shop was helpful and didn't seem to see the true guy, but I was working to keep that dude under wraps. I purchased a small simple Coach bag, a women's wallet, and a Swatch. She had to help me with the clasp. I was a little nervous as she held my wrist.

"You have such fine features dear, I wish may hands looked this good. I like the natural finish of your nails. The red leather accents your black dress so nicely. And the camel bag is a good selection. Shall I remove the stuffing and tag?"

I decided to park across the Green so I could practice the speed and length of my gait. The varied surface of the walkways required focus. The concrete and stone were ok, but the path across the Green was dense gravel. Each step had to be considered. Entering the bar I saw it was nearly empty. The bar girl didn't give me a second look which calmed my heart rate and she smiled as she asked for my selection. The Pinot was pleasant and I chatted with a couple about the neighborhood while seated looking out to the Green. A single gentleman came in but seemed to be waiting for someone. I finished the glass and considered taking a longer walk about the Green. I needed more practice to help break in the 3½" tall shoes. It was a nice evening, my heels clicking on the bluestone as I moved around the outer ring of the large Green. The surfaces were easier to deal with than the gravel as I practiced my new walk.

"Excuse me Miss, do you know where Tony's Bistro is?" a young man called from a car along side the curb.

I looked about to get my bearings, "You might have just passed the street, off to the left back about 300 yards," he smiled and thanked me, then drove off in the wrong direction. A moment later he came by slowly and stopped again, now heading the correct way.

"Thanks for the help. Could I buy you a drink Miss, if you have a few minutes? My meeting doesn't start until 7:30 and I . . "

I cut him off, "I appreciate your offer sir, but I've got to get back, Thanks." And I turned at the block where the Audi was parked. I wondered if how I'd spoken had sounded to manly, '300 hundred yards' seemed very specific. I lived in a small Village but the Green attracted quite a few people to the nearly twenty small restaurants.

He moved off a little slowly, maybe checking me out as I got in and started the car. My first adventure seems to have gone off without a hitch. I enjoyed the flirting and the walk. I was surprised how these heels weren't a bother. Cheryl had said the money would be well spent, $425 for a pair of shoes? The affect on my posture was a good thing and I liked seeing my reflection in the storefront as I'd walked past. Window-shopping hadn't been important before.

I now understood the term 'passing' that I read about on-line. Esther and Cheryl weren't playing me. I could dress and look sufficiently womanly. It was a good day, I'd been dressed and acting this new role for the entire day. At a traffic light I checked my face, I still needed to practice with the tones and powders. My face looked too shiny.

Back home I did some Site maintenance and then found a sexy site with pictures of transwomen that weren't racy and under dressed. I search those words 'under dressed' and a site video with two beautiful women making love popped up. While I had dressed as a woman for three days, this was my first time thinking of my new activity in a sexual frame. Maybe I would slipped my dress off and play for a while.

The two women were shown in lingerie, one in a silvery white, the other is black, each removing some garments and than re-dressing. This seemed so sexy to me and I moved to select the items I might wear. Removing the dress I went to the mirror, the heels pushed my bottom high and my calves looked remarkable in the taut hose. I lifted the hem of the chemise and adjusted the fit of the garters off of the suspender. Turning to look at my back I could see the image of the women in the video touching each other, but I was distracted by the small tuff of hair on my lower back. I needed to consider shaving or some other method. Maybe I should get a removal cream?

Returning to the mirrored view of my butt, I adjusted the thong and the re-positioned the garter straps on the hose seeing how the two girls had accomplished theirs. I was a little stiff as they played. I turned to review how the chemise looked hanging over my bra. I needed to loss more tummy flab. I went to drawer and picked out one of the two waist cinchers I had received. The nude one was a simple tube with ten hooks. It was a challenge to attach the garment but it did as advertised, with the chemise back on I saw a waistline. The exercise regiment would trim my waist over the next month. Until then I planned to use the cincher. Together with my wide hips the definition of a waist made me feel better. Comfort be damn!

I turned back to watch the girls, there lovemaking had moved along. The blonde in black was vigorously licking the other sexy girl. The one in silver was a real beauty. The world for porn actors wasn't too bad if this girl could enjoy herself and make a living. Her head was back, off the edge of the bed, and she was coming. I felt my panty and started to lightly tap atop my tucked mound similar to how the girl was in the video. I moment later I'd soaked my thong, the orgasm rising surprisingly quick. Today's near constant stimulation was enough to cause me to come. I hadn't touched my penis!

To be continued,

This could be quite an adventure for, Hallie? But she hadn't committed to a name as of yet. We'll see what she decides. Maybe it will be Charlotte, or Vickie, shoot why not Sara? It can't be Madeline, Tess or Louisa.

Thank you for reading! Maddy