A Week as a Woman
© 2017 by Nom de Plume

Sometimes magical, sometimes miserable, a real-life story of my week as a woman

My life is such these days that my time as a woman is restricted to business trips to a large city in a western state, where long hot summers and gray rainy winters are offset by endless autumns and lovely springs. There I maintain a small pied-a-terre with an apartment upstairs, and a downstairs office with its own access to the street. My apartment is in the heart of the city, a few blocks away from a thriving LGBT district with dozens of bustling bistros and nightspots. Business takes me there once or twice a month, and I always try to carve out a few days for my favorite pastime.
Hidden away in a closet under the staircase in the downstairs office, behind piled-up boxes and posters, is a complete woman’s wardrobe – everything from shoes and purses to lady’s golf clubs and a Maria Sharapova tennis racquet, painstakingly compiled over the years. It’s an ensemble for all seasons: summers in sundresses when I’m not lazing by the pool in my two-piece skirtini, falls in knee sox and cute skirts, and flowery dresses in the spring. Winter is – or used to be – my least favorite season, and often (like lots of real women) I won’t even bother to shave, hiding my body hair under long sweaters and tights.
A few weeks ago, a business crisis compelled me to spend a whole week in my hideaway, a week during which I lived 24/7 as a woman. I was lucky to get there: an ice storm was closing in, and I caught the last flight out on Saturday morning before the airport was closed for most of the weekend! When I got to my apartment that afternoon, just before spending a miserable hour with my mangroomer, I switched on the cellphone that I only use when I’m a woman, to find this text from a dear friend:
Can u join us 4 pizza at 6 at Rosettis?
I almost never get to be a girl over the weekend, and the message could have come in weeks ago, but I sent this reply anyway:
2nite?
After lugging several suitcases full of women’s clothing and accessories up from the downstairs closet, and hanging up a selection of skirts, dresses and coats (the forecast was for miserable weather all week) I was just stripping off my male clothing when my cellphone chirped:
Yes, r u here?
I couldn’t believe my good fortune! A girls’ night out! I quickly tapped out a request for directions, confirmed that I’d be there, and went to work on my body hair (ugh) with a song in my heart – tonight I’d be all dressed up, with somewhere to go!

* * *
I will spare the reader a detailed description of the lengths I had to go through to transform myself from man to woman – in the warmer months, when I keep myself shaved down for swimming, it’s a breeze, but the tedious task of removing several months’ growth of fur is not for the faint of heart. Anyway, when I finally emerged from the tub after a delightful bubble bath – my reward to myself for feminizing my body - I moisturized my now tender skin all over, applied my makeup, put on my wig (a collar length bob, which needed a good shampooing, but there was no time for that and besides, it was raining cats and dogs out there) and in no time I was ready to get dressed.
What to wear for a girls’ night out at a suburban pizza joint on a stormy Saturday night? I decided on a ruffled blouse under a black vest, a short skirt which was cute with opaque tights, and ankle boots which were still the rage.
I made sure that I had my fake female drivers’ license in my purse as well as my real, out-of-state license in case I had an accident (always a worry when I’m driving as a woman) before I put on my most expensive female possession, a Jones New York trench coat which has traveled around the world with me, and headed out into the storm. The drive was dreadful, and I forgot to turn on the headlights of my rental car until a nice guy pulled up beside me and blew his horn to get my attention, but eventually I got there, and parked in front of a cool Chicago style pizza restaurant in a suburban strip mall. I dashed in through the driving rain, and immediately spotted my posse: a large table in the center of the restaurant, where six or seven men dressed as women greeted me like a long-lost sister.
I took the remaining empty seat at the table, hung my sopping coat over the back of my chair, and let myself unwind for the first time that day. A few years ago, I might have recoiled at the prospect of being seen in the company of fellow crossdressers – my ego is such that I try to blend into the woodwork when I’m a woman, rather than draw attention to myself – but a good friend helped me get over that, and now I find the whole scene rather amusing. Here we were, obviously men dressed as women – several of the “girls” were well over six feet tall, and a few of them could have been retired NFL linebackers – surrounded by families and couples on dates, who paid absolutely no attention to us. Of course, it helped that we were in a progressive state: if we’d entered a pizza joint deep in the heart of Texas, we probably would have been laughed out of the restaurant, if not worse….
The impresario of our little gathering (the gal who had sent me the text) was seated at the other end of the table, and I found myself seated next to two total strangers. On my left was an androgynously dressed boy, quite good-looking, who in turn was seated next to a tgirl I’d met once before, at a Halloween gathering where she’d been dressed as an angel. She made a beautiful woman, probably the most attractive tgirl I’ve ever seen, but she was preoccupied with her boytoy, so I turned my attention to the lady on my right.
It’s always easy to start a conversation with someone you have something in common with, and I quickly learned that she’d been on hormones for years, which explained her lovely skin and soft, feminine face. She’d recently come out full time at work, which had presented the usual challenges. She hadn’t had any surgeries yet, although I think breast implants were in her immediate future. But what struck me most about her – and several of the other women seated around the table – was that she was enormously overweight. Just having a waistline made me feel downright petite by comparison, and I marveled when she ordered her pizza with extra-thick crust and asked for more blue cheese dressing to go on her salad!
The pizzas presented to the other gals were similarly loaded with extra cheeses and toppings. Why, I had to ask myself, would a guy endure all of the hassles and humiliations of transforming himself into a woman, and not want to watch her weight? If she lost a hundred pounds, she would make a beautiful woman. But who was I to judge? She seemed blissfully happy as a fat girl, and she was in good company as the other women around the table demolished their monstrous pizzas.
Anyway, our waitress was a total sweetheart, and she deftly served my dinky thin crust pizza and two glasses of Chardonnay. By the end of the evening, I’d loosened up, and I thoroughly enjoyed the food and the company. But I was facing a long drive back to my apartment in the unrelenting rain, so after hugs all around, I said my goodbyes and headed for home.

* * *

I slept in Sunday morning, in my pink flannel nightgown, and watched the morning news in bed before I got up to face the world as a woman. The rain had stopped, so after shaving my face, I threw on my leggings, sports bra, jogging skirt and jacket, pulled a visor over an old wig, laced up my sneakers and headed out the door for a long run, determined after last night to keep my girlish figure!
During my run, I checked the marquis in front of a nearby church and determined that there was an 11:30 am service. Going to church dressed as a woman is always a very spiritual experience for me – I don’t know why God made me this way, but I feel very close to him when I enter his house in my preferred gender. So after I got back to my apartment, and suffered through 200 crunches to finish off my workout, I took a nice bath, and dressed myself as a church lady. I’d washed my wig overnight, and I was feeling quite presentable in a knee-length skirt and sweater as I headed out the door after a light breakfast.
It was raining again, but with my trusty trench coat and a mini umbrella, I was able to make it to church with nothing more than wet legs, soaked through my stockings, which only reminded me that I was dressed as a woman. It’s hard to explain, but once I’ve transformed myself and spent a day or so en femme, I get so into my female persona that I can forget that I’m a man. The church was lovely, the other parishioners were very kind and accepting, and I just lost myself in the service. Time seems to move more slowly when I’m a woman – when I’m a guy I can’t wait for a church service to end, but that day I savored the sensation of sitting amongst the other conservatively dressed ladies, although I ducked out a bit early to avoid an awkward greeting from the minister….
How to spend a free Sunday afternoon as a woman? When I scheduled my trip, I’d alerted my boyfriend Bill – who lives a few hours away – that I was going to be in town, in case he could come up with an excuse to come see me. We’ve been dating steadily for over five years now (if seeing each other two or three times a year can be called steady) and I’m manic about the fact that he’s never seen me in the same outfit twice! Anyway Bill sent me an email that morning confirming that he was good for lunch on Wednesday, and I was bound and determined to find a new dress to wear for him. So after I swapped my soaking flats for some comfy Mary Janes, it was back in my rental car for a trip to the mall.
Have you ever fallen in love with a dress? I did that day, after I spotted it hanging all by itself at the end of a rack – it was a beautiful sweater dress by Elle in winter white, with black horizontal stripes offsetting a band of pink across the bodice, and a belt with a cute little bow. I just had to try it on! Into the fitting room, where I pulled off my skirt and top and tried to figure out how to put it on without mussing my hair. There was a little makeup stain on the collar, which must have explained why it was drastically marked down, but I’m an industrious girl and I knew how to get rid of that! I tugged it over my head, smoothed it around my legs and fastened the little belt tight. The moment of truth: so many times a dress which seems perfect just doesn’t drape right, but not this one! Looking back at me in the fitting room mirror was a pretty woman who liked what she saw.
Before I left the store, I scored a chunky necklace, also on sale, which would be perfect with my new dress. When I got home, I took care of that stain, and hung it up in my closet to await my date with Bill.

* * *
Monday morning dawned wet and windy, a powerful storm that showed no signs of letting up. Not a problem for me: today was to be the first of five straight days working almost nonstop in my downstairs office, trying to pull together a business transaction that was to tax me to the fullest. And every minute, from early in the morning till late at night, I would be dressed as a woman!
After pulling a robe over my nightgown and putting on my slippers, I’d sit down at my computer and send out a round of emails to all of the participants, including a difficult seller and a problematic partner, as well as the usual retinue of lawyers and consultants, outlining the things that needed to be accomplished. While waiting for them to wake up and respond, I’d treat myself to a hot bubble bath, and put on a different career girl outfit each day, usually a skirt suit, heels and stockings.
I’d fix myself a light breakfast, and after coffee and a cigarette on my balcony (which was sheltered from the almost constant downpours) I’d head back downstairs and try to keep our transaction from going off the rails. There were a number of seemingly insurmountable problems, compounded by the fact that the seller and our partner truly hated each other! Maybe it was because I was secretly serene in my female clothing, barking orders over the phone while I dangled a high heel off my stockinged foot, but I always managed to keep one step ahead of the endless crises that came up. I’d break to fix myself a light lunch, or duck out to a nearby frozen yogurt shop, then I’d be back at it throughout the day, before I finally took a break late in the afternoon to slip into something casual and do a little shopping.
Then, after more phone calls and emails, I’d take a long, hot bubble bath and change into a dress for dinner. Every night, I’d treat myself to a cocktail and a cigarette on my balcony before putting on an apron and whipping up something for dinner. Then it was back to my computer, where I’d pour over the mountain of documents that had come in during the day, before curling up in my nightgown and falling asleep to a late night television drama.

* * *

After two days of this, I was ready for a break – my date with Bill! The clouds parted on Wednesday, and I was able to go for another long run before I hammered out the morning’s emails in my jogging skirt and leggings. Then, after some tough telephone calls, I went back upstairs and tuned out my business problems. I was a girl with a lunch date at a romantic restaurant, with a handsome man, and nothing was going to stop me!
So I shaved myself closely all over, first with my mangroomer and then in a long, lovely bubble bath, before I moisturized my body and started in on my makeup once again. I took my time, adding a few little flourishes and tricks that make me look younger, before I carefully brushed my wig and slithered into some sexy lingerie, including a new pair of sinfully sheer nude pantyhose that felt delicious against my freshly shaved legs. After I stepped into a white slip with a lacy hem, it was time to put on my new dress. Carefully (remember that makeup stain some other girl had given it?) I pulled it over my head, tugged it down to my knees and fastened the belt. It was just as gorgeous as I remembered! After fastening my new necklace, I stepped into some classy patent leather heels, organized my purse, and waited for a text from Bill.

*

There he was, right on schedule! I put on a light cardigan which matched the stripes in my dress and headed for “our” restaurant, a charming Spanish bistro a block from my apartment. I got there before Bill, so I ducked into the ladies room to make sure that my hair and makeup were perfect. He was just striding into the restaurant when I emerged, and to my surprise he gave me a soft kiss on the lips before he asked the maître d to show us to our table. Bill was always the man in charge, and I fell in line behind him as we were shown to a corner table overlooking the street. I sat down demurely, smoothing my dress under me and crossing my legs with a swish of nylon.
Bill and I have known each other forever – we even went to the same university, although he was several years ahead of me – and we quickly fell into male/female conversation, chattering away about nothing in particular as we surveyed the menu and brought each other up-to-date on what was happening in our lives. He told me how much he liked my dress, which melted me a little bit, and by the time we’d finished our lunch with two glasses of wine, we both knew exactly what was next on the menu! He walked me back to my apartment, I gave him a little kiss while we rode up the elevator to my floor, and after we went inside I kicked off my heels and sat down expectantly on the sofa in my living room.
Bill sat down beside me, and we lost ourselves in a deep, passionate kiss. I’m afraid I was impatient to move the action to my bedroom, but before I got up he teased me about my slip. “Look at you, you’re wearing women’s underwear!” he said as he fondled its lacy hem.
“Um hmm…wait till you see my new nightie.” With that, I excused myself and went into the bathroom, where I tore off my dress and lingerie and slipped into a sexy little babydoll and panties that I’d been saving for the occasion. I even replaced my pantyhose with boy-friendly thigh high stockings before I presented myself to Bill with a little twirl. “Does the gentleman approve?”
Did he! Before long Bill was undressed, and we were romping under the covers. After I stroked him for a while, I put a condom on him, lubed it up and sat on him, face to face, gently rocking back and forth and up and down as he grimaced in ecstasy. Every so often, I’d lean forward and give him a kiss, which he returned in kind, until he asked me to roll over. After I did, he treated me to a wondrous succession of kisses starting in my back, moving down to my butt, then somehow he got under me and repeated the process as he suckled my panties, my tummy and my breasts. By then I was getting pretty hot, and when he removed my panties and took me in his mouth, I was on an ecstatic plateau, which seemed to last forever as he gently sucked on my hardening cock, teasing me with jolts of pure pleasure as he brought me closer and closer, until at last I cried out and came with rush. He milked me tenderly, relishing every drop, and when at last I was done, we lay there for a while before I told him, “Your turn.”
I knew what turned Bill on, and for the umpteenth time I did it to him once again, lubing him up and taking him into my hand, sort of a backhand position which he’d taught me years before, enabling him to slide up and down at his own pace and “fuck your hand” as he called it…we kissed each other while he gradually built up steam, until he started to moan and I knew he was close. When he came, the pleasure he felt was matched by my feelings of complete femininity, from being able to bring my man to a satisfying climax.
As always, after we cleaned up and he put on his clothes, I put my robe over my nightgown and served him coffee. We sat there, contented and happy, as we sipped our coffees and marveled over the incredible relationship that had grown between us. After he finally kissed me goodbye, I took another bubble bath, and reluctantly returned to reality. Well, not complete reality: I was still dressing and living as a woman!

* * *
The next day was the worst of all. Another dark, dreary day with sheets of rain, another succession of unexpected problems, and even the skirt and stockings I was wearing didn’t do any good. By late morning, after another impasse, I decided to change into pants and drive down to inspect the property we were trying to acquire, to see if it had flooded from all the rain. On the way back, I stopped at the market to stock up on food to cook for myself. I missed Bill, my deal was going down the drain, and I was feeling pretty miserable.
The low point came when our sellers made another ridiculous demand, which I knew – from years of experience – that they would drop if we told them no. I told our partner that we were playing a game of chicken, which freaked him out, but in the end he let me have my way. That evening, I told the sellers that they’d just killed the deal, and gave them the night to think about it.

* *
Friday morning, another rotten day, with our deadline fast approaching and our deal in limbo. Another career girl outfit, another breakfast, another day at my computer and on the phone in a skirt and stockings, trying desperately to hold it all together.
The big breakthrough finally came, as I knew it would, when the sellers finally folded an hour before the deadline! All we had to do was sign a harmless side letter signifying nothing, which I rammed down our partner’s throat, and we were done!
That night, I decided to reward myself with dinner at a nearby restaurant. And it was a good thing I did, because no sooner was I all dolled up than all the lights went out in my apartment! Fortunately, I was able to make it out the door in a sexy skirt and top.
It was so lovely, being shown to a table for one and treated like a lady at an elegant restaurant, until all the lights went out at the restaurant too! Fortunately, by then I’d been served my dinner (and a half carafe of wine) and the scene at the bar was getting quite rowdy as I put some cash on the table and made my way out the door and back to my apartment, where the lights were still out from a wicked windstorm.
It may seem trivial, but I was really facing my biggest crisis of the week: could I manage to put all of my female paraphernalia back where it belonged, remove my makeup and nail polish, and transform myself back into a guy in time for my flight first thing in the morning?
I won’t keep you in suspense: working slowly and methodically, and with the aid of some emergency lights that lit my office and apartment with a dim glow, I managed to remove all traces of my week as a woman, put everything back where it belonged, and get a few hours of sleep before the lights finally came back on at around 3:00 in the morning. A quick survey of my office and apartment confirmed that everything was back in its place, and I even found an email from my boss, praising me for the manful job I’d done that week. If he only knew!