Dear Auntie Helga,
Once again, it's time to recount a weekend experience that may be found interesting by you and your readers.
In the past, the Christmas party sets the agenda for the first holiday weekend of the coming year. This year they were able to have it at the office again as the obstructions to having it there last year were gone. For some in the office, it had been quite a while since they'd seen me. Two years on hormones and diet obviously had changed my appearance, which prompted compliments from friends and a few insults from others. I rather expected that from the insecure males. I wore a new Mrs. Clause outfit for the event with a top that was cut low enough to show my boobs were for real. That feeling of knowing where people are staring was for real too.
The party was more or less the usual Christmas office party and come 9 o'clock, most went their separate ways. Claire had her own little conference room party, at which time I had to change into a maid outfit, but leaving on those miserable 4" heels, and clean up the office from the party festivities. At one time, Penny called me in to refresh the drinks they were having. I said my hellos as I've been to most of their homes before. Claire introduced me to a new girl, who gave me a smile, almost a smirk. As I resumed my duties cleaning up from the party, the new girl won the competition for my services during the holiday weekend in February. My preparation for that started a month early.
Claire told me to shave my body starting on New Years. I wasn't going back to male clothes or anything close to that, just a little something that would be put into play come the first holiday weekend. My face, arms and underarms must stay be free of hair though. Up until summer, I'd never worn panties under my pantyhose. However, now that I can remain tucked up and passable down there all day, I do, though they must have a floral print on them. These didn't look very attractive as the weekend got near and hair surrounded them. And with that in mind, Claire gave my behind a stern tanning Tuesdays and Fridays for having body hair. After all, Claire's rules are Claire's rules. It was requested that I wear pants, shirt, tennis shoes, appear as close to male as possible. Thankfully, the jeans didn't reveal male or female, but wearing a guys shirt these days is rather awkward. The rest of my weekend clothing needs, Claire had packed in a suitcase, locked and sent me away with.
When I arrived, "D" as I'll call her, looked rather shocked at the difference in what she saw in December and today on her porch. She showed me in and gave me a quick tour of her condo. It wouldn't take me long to clean for sure. What would 3 days bring? D had me leave my suitcase in her bedroom for reasons I had no idea of, but said "we'll get to your clothing later".
We sat down with some tea and small talk which became a fact finding session for her. She pulled out a piece of paper which when she read from it, sounded like a time-line of what has become my sissy life. Everything from my legs needing these pantyhose, acquiring feminine shape by corsets and hormones, to now being a "sitter" in the bathroom. She'd never heard of a ball board or riding the horse. And while I gave her the details, from love of wearing and doing most everything feminine, to the not so fun aggression Claire and her workmates take out on me. She took in every word with a look of shock. It was obvious she was truly sheltered in life. A few cups of tea later and I'd had to excuse myself. She followed me into the bathroom and watched as I had to drop pants and sit. It's not the first time I had a spectator to watch me the last few months. She shook her head and said "When I moved out on my own, I never had to worry about the toilet seat being left up until I had a boyfriend. This must be a slice of Eden for Claire." She told me to stay there and we'll get the weekend started.
D came back with some contents from my suitcase. My grooming kit and makeup bag. She wanted to watch the entire transformation from male to passable female and she was going to do some of it along with me. First I had to remove all my body hair. She asked that I start with my personal area, cover that up, then call her in. At that point, she watched me shave head to waist, but when in came to shaving my legs, she joined me and shaved hers right along side of me while wearing panties. She watched me doing that very carefully and with fascination. We both went to her bedroom with towels around us in the female wrap style. She had two chairs in front of her vanity. We each took a seat and she gave me my make-up. As we did our own, we talked about my first time shaping my eyebrows, threading vs. plucking vs. waxing. Then we painted our toe nails. Hers was a pearl type color, which I was envious of. My color was a deep red with glitter. A stand out color if ever there was one.
That done, she'd gone to the suitcase again and put out the clothes I was to wear next. The blue maids outfit with blue flowered panties, panty hose and the rhumba bra. But before I got dressed, I had to tuck and tape my package to hide the bulge in the panties. For that, she'd put her phone on a nightstand close to her bed to record it. She wanted to see the process but would watch it as a recording. Perhaps she was too modest to take it in live. Much more timid at this than any of Claire's other workmates that have been in charge of me. Once done, I finished dressing and put on the blue heels. D came back and while she looked me over made comments about my legs again. I was blushing.
I got busy on her place, cleaning, dusting, doing laundry which included ironing her clothes. She had left during the process and brought back lunch for us. As we talked she seemed rather restless. Finally she said "The remaining cleaning can wait, let's go shopping". And with that, she grabbed another one of my outfits, tights, flats and a sweater. I changed and away we went. It was just us shopping. She shopped at random for different things but at one store, she insisted I try on a couple different dresses. She handed one to me and in the room I went. She waited outside to see it on me, and when I presented myself in one, she handed me another to try on. It was rather short and a bit tight fitting, but still rather flattering all things considered.
Once in front of her, she had me turn around as the phone recorded the moment. Then she made a call telling someone (turns out it was Claire) "...it's a bit snug but could be zipped up all the way." As she put the phone in her purse, she said to me "By getting into that dress, you avoided a date with Cassie". It was a size 10, where lately I have been a 12 dieting to get down to a prettier size. I'm much smaller than I was at the beginning of this whole change. Bigger boobs yet smaller waist, arms, thinner legs too.
Back to our shopping...
One of the retail areas we shopped was property that I own. As I told her this, I saw her wheels thinking I'd get outed parading through the stores. I explained they were handled through a property management company, which allows me hands off in the daily activities, but keep a watchful eye on them. Shopping there as a customer, and nobody having a clue who I was in there was a thrill. She did tease me about going back in and introducing me as the owner. I explained again I own the property not the businesses, but it still might have been a bad thing. Maybe just my paranoia.
Throughout the day, I carried all the bags, staying close as she shopped. She was constantly asking about my living like this. Her trip to the "big city" for a job had turned into quite the education. One more shop before going back to her place and it was for shoes. Heels for me that were by no means "sensible shoes".
Once back to her place, that tight new dress I had to model for the camera was handed to me and I was to put on the new shoes. I came out to show the clothes and she told me what the rest of the night would entail... learning to walk. I thought I'd had it down just by being able to walk in heels but not to her standards. Prior to working with Claire, she was an accountant for a modeling agency in a nearby town. And although she had behind the scenes tasks, she was very familiar with the training. Thus, learning to walk was going to be her addition to my being "feminine".
First though, was being recorded as I walked now. It looked rather normal to me but this would be a thing of my past every time I wear heels she said. My new stride was to be one foot swinging slightly in front of the other. Like walking on a beam. And straight posture, head still. My fingers had to be somewhat pointed away from my body. At one point, she'd taken a tennis ball and placed it between my knees. I had to walk but keep the ball in place. It did teach me how to make the hips sway a bit too. This went on for over an hour. Time to show if I could do it without aids. The first few steps, yes but then it slacked into the prior stride. Bringing back the tennis ball, we started at square one. As the night wore on, so did the lessons. After 1am, I'd finally had what she'd called a "Nice gait". She brought me my teddy and I was to sleep on the couch. I was so tired, there was little time between lights out and falling asleep.
Sunday, we'd gone for more shopping. I was wearing heels and the dress purchased yesterday, and D kept a watchful eye on my walk. At one point she said, "you were able to avoid Cassie by fitting into that size 10 you're wearing. Should you not have the right stride today, Cassie would still be glad to meet up with us and give your behind a bit of color." Not wanting Cassie binding me to a chair and giving me strap-on and or swats, I was paying close attention to my stride. So in heels, it's a different walk than in flats and tennis shoes. I learned it well. At least well enough to escape the wrath of Cassie that weekend.
We went back to her place and after putting things away, D handed me some moisturizing cream and sat on her couch in the position Claire takes when it's time for a foot massage. For the rest of the evening, while I pampered her feet, she would go through the notebook and start one of the letters. Then I was to tell of that weekend as best as I could remember. It was validating to her. It also gave her a better insight of some of her workmates. I hope not in a bad way. Monday, it was back into the maids outfit and clean her place as never before. I made sure every corner was perfect.
We went out to dinner, I in another new dress, her in a smart pant suit. She informed me that this was actually the first of two weekends I would be spending with her. This was different. The second will be something she promised worthy of recounting to Aunt Helga. As if all of the weekends I spend under other women's control aren't?
Back at her place, I packed up my suitcase and asked if there was any last minute things D needed. She said all was well and had something for me. She asked me to hold out my left hand. She locked on my charm bracelet, complete with a new charm from her, signifying that she was satisfied with my performance over the weekend. Thankfully!
If that wasn't there, it was going to be hundreds of swats from Claire for sure.
Thank you for your letter Brenda. Your weekend with D sounds delightful, a very typical girlfriend experience, perhaps a safe way for her discover her own feelings about having a willing male to experiment with and she seemed to really enjoy herself.