A Day of Firsts
by Kathryn Nelson
It was one of those hectic work periods where I was putting in 70 to 80 hours a week. You know, when there's no time for anything else in your life except the job. But, thank god the rush was over and it looked like things were going to calm down.
Friday night had come around and I was going home at a decent hour. I even had the whole weekend off and I was ready to celebrate. Well, more like unwind than party.
I live alone in the city. I was fortunate to get a two-bedroom apartment in a rent stabilized building a few years ago. At 24 years old and single, it was a real luxury to have this much room. The rooms are kind of small but, I have my own bedroom and my sister uses the other. I know, I said I live alone, I do. My sister and I are close, real close. In fact, we share everything, including the same body.
I should explain that I feel like I lead a schizophrenic life. Most of the time I'm Peter, the one who works long hours. But, sometimes I'm Polly, my sister, when I need to relax. While my bedroom is kind of grungy and dark, Polly's is bright and frilly. She has an obsession for things that are lacey and pink. Her room is decorated in intense floral patterns with stuffed animals everywhere.
I've been a crossdresser my whole life and since I got out of college, I haven't bought much for myself but, Polly spends quite a bit. Mostly through catalogs and more recently through the Internet. Like I said, at times I feel like two different people who just happen to share the same apartment.
Since Polly hasn't been too active lately, due to my workload, I decided that she should have the whole weekend to herself.
When I got in, I ate some Chinese take out I had picked up on my way home and then began the transformation. Most days I just throw on a nightgown and read in bed but this weekend I needed to take it further.
I ran a warm bath and poured some fragrant bath oil in as I stepped in to the old cast iron tub. I lay there for a while just relaxing my mind before I reached for my Lady Remington razor and began to work on my legs. I have one of those wet/dry models that works well with enough cream to soften the hairs first. I took my time and got all the way up to my crotch being careful to get all of the hair off.
I was really in a relaxed state that contributed to my decision to shave not only under my arms but the hair on my arms too. After doing that, it took very little to convince myself to do my chest and stomach too. I had only done them one other time before and the itching that followed a couple of days later made me miserable. Somehow tonight, I didn't care.
When my bath was finished, I stood up, drained the water and ran the shower. I washed my hair with some strawberry scented shampoo and then used some conditioner. My hair is dark brown and fairly straight. I hadn't gotten it cut in a while so it was around the bottom of my neck but not quite shoulder length yet.
As I stepped out the tub, I wrapped one towel around my waist and took another one out to wrap around my hair and balanced it on my head. I entered my (Polly's) bedroom and decided on wearing an ivory silk chemise with matching tap pants. I took out one of the beauty magazines that I picked up several weeks ago. It was for stylists and described how to cut different women's hairstyles. I opened to the page I had marked earlier and found the picture of a woman with large flowing curls. I skipped the cutting section and went right to the curling instructions. My hair wasn't the same so I had to improvise a bit. I had a set of rollers and used the largest ones I had to try and match the effect. It took me several tries to get it right and when I was satisfied, I applied the setting lotion. Nothing permanent mind you, just something to last the weekend. I had this pink hair cover that came with the rollers I bought, so I put that on to keep everything in place.
With my hair all set, I had to decide on a color for my nails. As I looked over the dozen or so choices, I carefully filed and shaped my fingernails. I would go all out this weekend and put down a base coat first on my fingers. I went with a red in one of the deepest shades I owned. I'm never really sure where I'm headed as I transform myself. It's just whatever hits me at the moment and I only hope that I reach my destination without looking too ridiculous. I did my toes in one coat but decided on two for my fingers. I topped it off with a clear sealer that left them very glossy. I knew this was overkill since it would all come off by the end of the weekend but I didn't care. Maybe I'd even keep the color for my toes on during the week.
It was getting late by then so I decided to call it a night. I made sure my fingers and toes were completely dry and hopped into my bed with some of my favorite stuffed animals. I turned out the light and tried to drift off to sleep. The problem was, I had forgotten how hard it was to sleep with curlers in my hair. I tossed and turned for a while until I got a little more comfortable and slept on and off through the night. I kept waking up to the
sounds of the city twelve floors below so it was mid morning by the time I finally decided to rise.
Waking up as Polly is one of the things I enjoy most in my life. I look around the room and feel that I'm in a totally different place than the way I spend my usual day either working or coping with being Peter. I feel peaceful and very contented. But then I have to get out of bed!
Looking at the sewing machine in the corner, I decided that I really should try to finish that A-line skirt I was making. So for today, I would be Suzy the seamstress. Sewing is not my real forte but, occasionally I get it right and the clothes fit my special shape (no hips or butt).
I first ate a quick breakfast of yogurt and a banana, trying to keep my weight down, but I topped it off with a leftover fortune cookie. When I cracked it open, it told me that I was in for some exciting changes. Right! Spending the day alone in my apartment sewing a skirt was as exciting as things get for me.
As I finished eating, I looked around the place and noticed how dirty it really was. Funny how Peter can easily overlook the filth but now as Polly, it disturbed me. A change for the day was in order.
I went into the bathroom and shaved my face twice till I was happy with it. Then back into the bedroom to sit down in front of the vanity. I went all out with foundation and powder to hide any traces of my beard and lines. I was extra cautious with my eyes, making sure I didn't overdo it. I have a tendency to put on too much liner and mascara that gives me very black eyes. Also, the shadow today was more in the lighter tones and I trimmed my brows with a little more arch to them.
My lips, which take forever to do, were in the same shade of red as my nails. For some reason, I have to have them perfect before I can continue. Pretty silly since they get wiped off and need to be redone the most often.
After I was satisfied with my face, I began to tackle my hair. When I took out the rollers, I realized that the curls were tighter than I desired so it took a while to brush them out. After comparing myself with the magazine picture and making several adjustments, I dowsed it with a half a bottle of hair spray.
Glancing at the clock, I saw that two hours had gone by and I wasn't even dressed yet. Polly the perfectionist was running late again. I headed to the dresser and opened a brand new pair of stockings. They were a designer brand in black with a small diamond shaped pattern down the back. They felt so smooth getting up my legs and I was real careful not to snag them. I attached them to my black lace garter belt and gently adjusted the seams.
I decided to skip the corset I usually wear and instead, opted for a long-line bra. It was a lot more comfortable for the work I needed to get done today. I slipped in my prize possessions, a set of expensive breast forms that gave me a 36C chest. A silk camisole went next to hide the lines of the bra.
Looking through my panty drawer for the right ones was one of the hardest decisions of the day. There were so many choices of styles and colors. I settled on the frilliest pair I owned. They were white with ruffled lace edges all around, almost like petti-pants but shorter. They puffed out the most of anything I owned and would make my skirt stick out more than usual.
I reached into my closet and pulled out a garment bag that was sealed shut. Inside was a black silk French maids dress with a white apron attached. If I'm going to spend the next few hours cleaning the apartment, I was going to do it in style. The dress was very short and I had to keep pulling it down to cover the tops to my stockings. I knew it was a bit small when I bought it through a catalog but I decided to keep it anyway. I little white maids cap came with it that I pinned in my hair.
I put the bag back in the closet and opened the door all the way to look at myself in the full-length mirror. I had surpassed myself from head to toe. I could have stared at myself all afternoon primping in the mirror but sensible Polly took over and grabbed a shoebox off the top shelf. I slipped on a pair of black leather pumps with a slim 3-inch heel. It took me a few minutes of walking around to steady myself before I headed out to clean.
Monique the maid was ready for duty.
With some loud background music playing on my stereo, I tackled the entire place. The kitchen, bathroom and the vacuuming were done and I was dusting the living room when I thought I heard a noise and someone calling hello. I paused for a moment and decided it was the music or someone outside.
I was bending over the coffee table, feather duster in hand when I clearly heard, "Oh, excuse me", come from behind me. I realized someone was in my apartment and had a clear shot of my stocking tops and panties under my short dress. I stood straight up and turned around quickly coming face to face with Chloe. She's my neighbor from across the hall. I was trying to figure out how she got in when I remembered that we exchanged keys once in case one of us was away and had to look in on each other's place.
It took her a second but she looked at me right in the eyes and put her hands on her cheeks. "Oh my god!" she gasped. Her eyes crept all the way down to my pumps and back up to my hair before looking at my face again. She was quite shocked and trying to get some words out but she didn't know what to say.
Meanwhile, I was looking for the right explanation to give her. A thousand different excuses went through my head at that instant but they were all lies. My defense mechanism took over and I decided right there that humor would have to do. I turned slightly sideways and looked down at my rear and legs.
"What's wrong? Are my seams not straight?" I said to Chloe.
A smile crossed her face as she began to relax. She stepped back a bit and then even circled around me to get the full tour.
"Peter, you...you look adorable!" she finally spoke.
I pulled out the hem of my dress on each side delicately with my fingertips and with one foot placed behind me, gave her a quick curtsy. "Thank you madam", I replied in my best phony French accent. That sent her over the top and we both burst out in a fit of giggles.
By the time we stopped laughing, we both needed tissues to dry our eyes. I had to be careful with mine to not smudge my face. Chloe had a hundred questions but overall she took it very well. She was a couple of years older than me and was single also. She told me that she had changed her weekend plans and decided not to visit her parents. I had totally forgotten that she told me this last week and asked me to keep an eye on her place. She said that she wanted to tell me that she would be around and knocked on my door. She heard music and when I didn't answer she used her key to come in. She apologized for the third time for barging in on me but I told her again to forget it.
I actually feel relieved that she knows. It's a secret that only a few pen pals on the web know and they're safe because I've never met them in real life. Chloe asked me what I wear when I go out and I had to admit that I never have left my home dressed up. She seemed a little surprised that she was the first to see me this way.
She asked about my name and I told her that although I was dressed as Monique, I mostly used the name Polly. She mentioned that she had seen packages in the lobby, near the mailboxes in the past with that name and my apartment number on them. She was always a little curious about that but was afraid to ask.
Then came the more personal questions.
"Peter, are you gay?"
"No." I immediately responded. "He worships woman and he's straight".
"And what about your sister here", she said pointing to me.
"Polly has never been with a man or a woman. But, she prefers woman also so, I guess that makes her a lesbian".
Now, I know from previous discussions that Chloe is straight and we have always had a plutonic relationship but the way she was looking at me gave me mixed signals. She asked me to show her my room so; I went in to show her the place that no one but me has seen. At least the place was clean but I was still a bit cautious. She looked around at the bed with the lacy sham, the vanity with more cosmetics than she owned, even the long wigs I had on Styrofoam heads in the corner. She commented that it looked like the room of a teenaged girl and a young one at that. I admitted that I might have gone a little too far with the look but it's what I enjoy. Maybe over time I'll mature a bit more.
I sat on the bed and watched her look around the room with amazement. I didn't notice that my dress was hiked up to my waist and she had complete view of my frilly undies and the bulge that was straining the fabric inside.
"Oh my, I think we should do something. Would you like to change?" she said to me staring right at my crotch. I noticed what she was looking at and stood up to adjust myself. I felt the time was right and excused myself to go to the bathroom to get ready. I never thought about the two of us doing it but, in my current state, I just wanted some much needed relief and jumping in bed with her was better than my usual solo hand job.
In the bathroom, I removed my dress and cap and hung them neatly over the curtain rod. I decided to leave the remaining articles on and do a strip tease in front of her to remove the rest. I wasn't sure what she had in mind but, I pictured her naked in my bed waiting for me.
I slowly entered the room and was surprised to see Chloe, with her back to me, was still dressed and looking through my closet.
"I have a few nightgowns in the top left dresser drawer." I told her thinking it was what she was looking for. She turned around and told me to close my eyes. Ooh, this was getting interesting! She told me to raise my arms up high and I followed her instructions immediately. I felt something very soft flow down my arms and across my chest. She pulled my arms down and arranged something around my neck. I could smell perfume and realized that she had put one of my cashmere sweaters on me. I opened my eyes to see which one it was but she yelled at me to keep them shut.
Next, I felt something over my head and down my sides as she moved my hands out of the way. I heard a zipper go up behind me and then a tight feeling around my waist. She was buttoning a skirt on me and I was getting confused as to why she was dressing me.
She reached her hands under the skirt and up towards my hard member. At last, I thought, some real action. But, her hands continued up to pull the bottom of my sweater straight down and tight around me. I opened my eyes and looked down it what she dressed me in. I had on a red sweater with a cowl neck and my black and red Tartan skirt that fell about four inches above my knee. The color of my sweater matched my nails and lips and the black stockings and heels were perfect too.
I was still a bit puzzled why I was dressed when Chloe left the room. I followed her inside and asked where she was going. "Come on", she said as she opened the front door. I froze at the doorway.
"Chloe, I told you I've never gone out before." I whined.
In one swift motion, she grabbed my arm and pulled me into the hall as she slammed the door behind us. I couldn't move while she headed down the hall toward the elevator. I realized that I had no key, no ID, nothing on me. I could go to the building super but he wouldn't recognize me to let me in. Or, if he did recognize me, I would be thrown out of the place. My only choice was to run after Chloe. She had the key and I needed it.
It wasn't so easy running in my heels and I got to the elevator just as the doors were closing and Chloe headed down. I pushed the down button and waited a few minutes for it to open again. It took all my energy to push the button for the lobby. God, I can't believe I was going out in public and that I might even run into more people I know from the building.
I calmed my self down as best as I could and looking at my reflection in the back of the shiny door, I straightened myself out to my best ability. When the doors opened, I was looking at an older couple on their way in. The woman said good afternoon to me as the man gave me quite a stare and a smile. As they got in and the doors closed, I heard the woman chastise her husband for gawking at me so much.
I made my way out to the street where at least it was warm and sunny for late autumn. I didn't need a coat but I wish I had one to hide my chest. This sweater was fine when I use to stuff my bra to a B-cup but, with these larger breast forms, the front was tight and the effect was not one I was looking for at the moment.
I looked around for Chloe but I didn't find her. Crap, what am I going to do now I thought.
"Hey, Polly. Over here", I heard someone yell. Chloe was sitting in the back of a cab at the taxi stand on the corner calling out to me. I ran up and she scooted over and told me to get in. I quickly hopped in and closed the door as the driver headed uptown. I realized that I wasn't so graceful getting in the cab with my skirt and I'm sure someone got a flash look at my panties as I entered. This was a new experience for me and I was getting a crash course thanks to Chloe.
"What do you think you're doing?" I yelled at her. "Look at me, I can't be out like this. Give me my keys."
"Oh, come on. Where's your sense of adventure?" Chloe responded.
It was then that I became conscious of the driver. He kept staring in his mirror at us; well mainly at me. My deep voice had given me away. I was made, another first! It was then that I wished I had bought the video on how to sound female. I never thought I would need it, who knew?
I kept my mouth shut the rest of the ride but the damage was already done. The cab driver kept looking at me the whole way and smiling. It was his way of indicating that he knew and what a story he had to tell his buddies later. Chloe did her best to get me to talk. She whispered to me that he was a cab driver and probably saw this kind of thing all the time. Maybe he wanted a little action and we could get a free ride out of it? That made me chuckle and I gave up a little smile.
The cab pulled over and Chloe paid him and got out. I carefully exited the cab putting both legs out on the sidewalk together. I had to hurry to catch up with her. No way was I getting left alone again. I grabbed her arm with both of mine and was led into a department store.
"What are we doing here?" I asked quietly to her.
"I need to get an outfit for my company Christmas party and I don't like shopping alone. Come on, loosen up, it'll be fun."
Some fun I thought sarcastically as we headed up the escalator together. I kept trying to stay close to her but she was moving at a good pace. I felt like it was a game of cat and mouse and in my heels, I did my best to keep up. I felt that everyone was staring at me and I tried to keep my head down and out of any ones direct view.
Chloe started looking through the racks of clothes, as I stayed pinned to her side. Finally she turned to me.
"Look, you have great taste in fashion. I've seen your closet and although some of the stuff is a little weird and some a bit childish, I would appreciate you giving me a hand here. Pick your head up and stop worrying what everyone thinks, you'll be a lot better off."
I gave in and started looking through the stuff on my own. I noticed we were in the plus size area which seemed obvious since Chloe was a large women. She was a little taller than me except now in these shoes, I was taller. She also weighed more than me by quite a bit. She told me she was a size 20W and wanted something a little festive for the party.
I found myself relaxing and walking between racks pulling off skirts and blouses in different styles. I know what looks good on me for my body but I wasn't sure about Chloe. There were no mannequins in this department so I looked around at what the shoppers had on. These women all wore pants with big tops to hide their true shapes. I concentrated on that look for Chloe, as I searched some more.
Glancing across the aisle towards the Misses department, a few things caught my eye. I walked over to a rack of dresses and grabbed one on a hanger. I turned towards a nearby mirror and held it up close to me. It was calf length and black from the bottom to just under my breast. At the bust line, it was gray for several inches and white from there up to the jewel neck.
"You're really enjoying this aren't you Polly", Chloe said to me as I jumped a bit from the scare. "But we're here to take care of me first you know".
I blushed a little red and returned the dress to the rack. I apologized and went back to her side of the floor. She had a few things in her hand and headed into the changing room. I hesitated at the doorway, not knowing if she wanted me to go in with her but a quick tug on my arm told me otherwise.
She was not shy at all about changing her clothes in front of me. She removed her sweatshirt and sat down to take off her sneakers. Getting up again, she took off her stirrup pants and threw them on the bench. She had very plain cotton underwear and a white bra that must have been a 46D or larger. She tried on several skirts and dresses but none of them pleased her. She did try a pair of black pants but the top she had was all wrong. I told her to wait there and I ran out to grab a top I saw earlier. It was a beaded red one in a heavy knit that I put over her head and told her to keep on the outside of her pants. She looked in the mirror and liked the reflection she saw back.
I thought we had a winner when she started to complain about the tightness of the pants. I ran out again and returned with a very nice pair of Gabardine slacks in black. These had an elastic waistband with double front pleats and rear darts. These fit her a lot better but they didn't fall exactly right. I slipped out of my heels and kicked them over to her.
"Put these on, I think they'll straighten the look out for you", I said to her.
"They're a little tight on me", she replied once she stepped into them.
"They're supposed to be tight, it's part of the suffering we women must endure."
That got a smile out of her and from the gaze in the mirror; I think she was satisfied with the outfit.
I complemented her on her appearance and even held her hair up and showed her a few things she could do with barrettes and hairpins to get the total effect. I even suggested that she stop at my place before the party and I would do it for her.
"Will you do my nails too?" she asked with a little begging expression.
"Of course, I'll give you the full treatment."
That included her makeup so I recommended we go down to cosmetics and get a few things she would need.
Chloe was excited and she paid for her new clothes and thanked me several times. At the cosmetics counter, I gave her some ideas on what might look good for her skin type and she asked the saleswoman for some samples. The woman saw that Chloe had no makeup on and was only too happy to give her a makeover. She glanced my way and asked if I wanted her to do me but I shook my head no and declined on the offer. The last thing I needed was to have her feel my beard. She gave me a strange look and I knew that I had been made again. I motioned Chloe to speed it up so we could get out of the store.
Chloe wanted to make one more stop before we left. She was looking through the accessories department at handbags when she picked one out and asked my opinion. It was a very plain looking black leather bag with a long shoulder strap and gold clasp. I told her I liked it in an effort to get her to hurray up and leave. To me it was very similar to the one she had with her but I guess a girl can never have too many purses.
With that purchase complete, we were back out on the street. Chloe stopped on the sidewalk and took her new purse out of the shopping bag. She removed the tags and then opened her other bag. She took out my spare keys and dropped them in the new purse and handed it to me.
"Here Polly, I bought this for you. I didn't see one in your room so I guess this is your first."
I was really surprised and declined her offer but she insisted I take it. I put the bag over my shoulder and got a feel for it. She placed the strap over my head and held the bag in front of me close to my waist. She reminded me that in the city, you have to keep it close if you don't want it taken.
Feeling a little playful, I said, "If you're in the mood to buy me things, how about that dress I liked upstairs."
"Yeah right", she replied, "Did you see how much those pants were? I'm on a budget you know and I'm not the clothes horse like you."
I laughed as we strolled downtown looking in the windows of all the shops. It was dark out and my stomach grumbled a bit. I hadn't eaten much that day and I wanted to get home. The problem was that even though I had a key, I had no money for transportation back.
Chloe pulled me into one of the restaurants we passed. I offered to buy but she understood my predicament. As I sat down at the table, I wasn't sure where to put my purse. She showed me how she keeps hers on the back of her chair and I followed her advice. I asked her to order for me so I wouldn't have to speak to the waitress but she refused.
"If you want to eat, you're gonna have to ask her yourself. How are you ever gonna get by on your own if you can't communicate?"
She was right. It was my biggest hurdle and I was still shying away from it. I did order myself but the falsetto voice I used made the waitress suspicious enough to give me a funny look. I sat dejected, as I was sure I was made again. Chloe assured me that it would take some practice and then I would be out all the time on my own. The thought both excited and terrified me.
After we finished dinner, on the way out, Chloe motioned me to join her in the ladies room. I was scared to enter but I did have to go too. She asked me where my purse was and I had to run bag to my chair to get it. The waitress was clearing the table and in seeing me held my bag up as if to acknowledge that it was left there. I gave her a quick, short "Thanks".
"That's alright honey, you'll get use to hanging on to it", she responded with a knowing smile. I was beginning to really hate it when they make me.
I returned to the bathroom and entered one of the stalls. Chloe started to talk to me from the next stall over and we chatted until I heard the door open and the distinctive sound of heels on a tile floor. I finished my business and went to the sink next to Chloe to wash up. Looking at my face in the mirror, I saw that my lipstick was just about gone. My hair was a mess and I asked Chloe for her hairbrush to straighten it out. What disturbed me more, was that my foundation was wearing thin and some of my beard was coming through. I must have been touching my chin a lot because it was the worst there.
I showed Chloe my face and told her that I had to get home right away. She agreed and before we could leave, I heard the toilet flush. An older woman came out of the stall and started to yell at me for masquerading as a woman to sneak peeks in the ladies room. She must have heard me talking to Chloe and was very upset about me treading in her domain. Fortunately, Chloe had already paid the bill so we ran out of there before the woman got the manager.
In the taxi back downtown, Chloe laughed about the incident and told me to chalk it up as another first. I was still shaken up and wondered how many more firsts were in store for me.
Back on our floor of the building, I opened my purse and took out my keys to open the door. I offered to get my wallet and pay Chloe back for dinner. She refused and said it was on her. I asked her if there was something else I could do for her but she said I did enough and thanked me again for the assistance in shopping and she reminded me of my offer to get her ready for the office party.
I was saying goodnight to her when she did ask for one more favor.
"You know Polly, there's nothing you need to do to repay me for dinner but, I think I could really use Monique's help tomorrow cleaning my apartment."
"Oh really", I said with a big grin. "I'll tell her to be there at noon."
I tossed my spare keys across the hall back to her as I entered my apartment and closed the door.
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