Three Perfect Days

United Airlines has a running series in their Hemispheres magazine, featuring a different destination every month: how to spend three perfect days in New York, London, Buenos Aires, wherever. Although no travel to exotic locales was involved, I just spent three perfect days in the western city where I maintain a small apartment for excursions into my secret life as a woman. I wouldn't have traded them for an all-expenses-paid trip to anywhere in the world!

I arrived late on the afternoon on a Monday, and as soon as I'd lugged all the suitcases jammed with female paraphernalia from a hidden storage area to my upstairs bedroom, selected the outfits I planned to wear, and hung them up in the closet, it was into the bathroom for the hated drudgery of removing all of my body hair. The weather was supposed to be lovely - sunny and a bit cooler than usual for May (it was that awkward interval before Memorial Day when proper ladies were not permitted to break out their white shoes and purses) which wasn't about to bother me: I had plenty of spring fashions to choose from, and I might even get to wear nylons if it was cool in the morning or evening! Most women would find that puzzling, but ever since I was a little boy, I've always loved to wear them...

My outfit of choice that first evening was a denim skirt paired with brightly patterned top, blue topsiders and a matching denim purse. After I tugged on a light cardigan (and yes, I yielded to temptation and slipped into a pair of pantyhose, which feel so good against freshly shaved legs) it was off to a nearby market for some produce. Then it was back to my apartment, where I blended margaritas, mixed a salad and whipped up a delightful Mexican dinner (from freezer to microwave) life was good!

After a cigarette on my balcony, I went downstairs to the office to send an email to Bill, my longtime male lover. We've been seeing each other for over seven years now, not as often as we'd like, which only makes our occasional trysts more intense. Over the years, we've created little nicknames for each other, as well as for our respective body parts - see if you can guess what part of me Carina refers to:

Bill Darling,

Little Carina is safely tucked away in silk and lace, under my denim skirt. She's resigned to spending the next day and a half being a good little girl, although I did feel her beginning to get a little naughty when I dressed myself this evening, I was able to snuff her in the bud, telling her to behave and save herself for the man she loves after two margaritas and a nice Mexican dinner (cooked by me!) all is well here in xxxxxxxxxx. It's so wonderful knowing that we'll be back in each other's arms on Wednesday!

Love,

Me

It was cool enough to sleep with the windows open, and so after putting on a cotton nightgown, I painted my toenails a shocking pink and snuggled under the covers, soon dozing off to an old tv show.

* * *

Day One dawned crisp and sunny. I put on my running skirt and a jacket and spent a wretched half hour sweeping off my terrace and scrubbing my outdoor grill, which hadn't been used in over six months. After a long jog, it was into the tub to shave off my last remnants of maleness (Carina and friends excluded!) and put on a blue and white wrap dress, heels and stockings for my morning as a working girl in the downstairs office.

I had twelve years of files to organize, something I've been putting off forever, but doing it as a woman helped to compensate for the drudgery of the task. At around 4:00, I changed into a khaki skirt and knee sox and waited for my oldest crossdressing friend to arrive from out of town for a much-anticipated girls' night out.

I hadn't seen her in well over a year, and I knew we'd have a lot of catching up to do, although little did I realize the extent of the changes to her life! After she parked in the underground garage and settled in, we were off to a nearby coffee shop for some girl talk. Now the last time I'd seen her, she was deeply closeted from her friends and family, although she went out frequently to a nearby, gay-friendly city. In short order, I learned that (1) she'd come out of the closet and announced that she was transitioning to a woman, (2) she was taking female hormones, and (3) she'd had her testicles removed!

She has always been very presentable and convincing as a pretty woman, and she's been blessed with a full head of hair which she can style into a very feminine look, so I can't say that I was shocked by her revelations. Not in this day and age! I just sat there and listened as she recounted some of the challenges of dealing with her family, which she was working through in a patient and methodical fashion. Then it was time for fast changes into sexy dresses for our prowl about town, first to a wine bar, then a fabulous restaurant, and finally a late night espresso at my favorite bistro, all within walking distance in heels.

Outings with her are always a bit surreal. She is totally uninhibited with strangers, striking up conversations with straight men and women as if they were long lost friends. But she is so genuine, and so obviously interested in what the other person has to say, that I have never seen her experience a negative reaction. Sometimes I feel like a bit of a wallflower while she works the room, but it's a small price to pay for being in the presence of a beautiful and unique human being.

When we finally returned to my apartment, she crashed on my sofa and I went straight to bed. As I drifted off, it occurred to me that the highlight of the evening was when a woman seated at the table next to us at the wine bar caught my eye (my friend later said that she'd been staring at me for a long time) and said hesitantly, "I just have to ask you, where did you get your dress?" I had to think for a moment before I replied, slightly embarrassed, "I got it at Ross."

* * *

Day Two I was up early, concerned about the logistics of getting dressed with another woman in my little apartment! She was still fast asleep, so I slipped out for another jog in my running skirt just as the sun was coming up, then I beat her into the bathroom for a quick shower before I put on my makeup and a peasant skirt and top.

I tiptoed downstairs and did some work on my computer until I finally heard her stirring. Then it was off to a coffee shop for a light breakfast, and back to my apartment for some more girl talk centered on all of the recent changes in her life, and the changes yet to come. I had assumed that by now she was living 24/7 as a woman, but she surprised me when she said that she still wasn't ready. "I don't get it," I said. "You've told everyone you know, you're on hormones, you've had your balls removed, what's holding you back? I mean, if I was in your shoes, I'd never put on a stitch of guy clothes again, ever."

She went on and on about how she still needed to accumulate enough casual women's clothing to allow her to dress up each and every day, for every situation, but I still didn't get it. Sure, most of her outfits were designed for nights on the town, but how tough could it be to put together a couple of skirts and tops, just to get started? She had a washer and dryer in her condo, so she could get by until she filled her closet. Shopping for everyday girl stuff would be so much fun! Why would she ever want to dress up as a guy again?

"I'm scared," she finally confessed. That brought me up short: my friend was light years ahead of me in the journey towards womanhood, and something was holding her back. But I knew better than to press, so the conversation drifted on to other topics.

After I finally shooed her out the door, I had to get busy preparing for my date with Bill, who was taking me out to lunch at that same little bistro. First I had to clean up after my galpal, then it was time for me to shave all over once again, douche myself, luxuriate for a little while in a steaming bubble bath, moisturize my body, put on my makeup and change into the new dress I'd been saving to wear for Bill. It's a color blocked sheath which gives me the illusion of an hourglass figure, and I was hoping that I could get away with wearing nothing but a Wonderbra, slip and panties underneath, with no padding. I also indulged myself with some very expensive thigh high stockings (Bill loves them, as most men do) and a cute pair of nude flats.

Bill called to tell me he'd been delayed, and I spent some more time in my downstairs office. Sitting there at my computer, it felt so nice crossing and re-crossing my legs in those sheer stockings, I could hardly complain! Finally he called again to tell me he was free for our date. I pulled on a cardigan which matched my dress, grabbed my purse and tripped down the stairs. Bill was waiting for me at the curb, and after I hopped into his car I helped him find a parking space in my garage.

I know this will sound somewhat strange, but after seven years, we've gotten totally used to our roles as man and mistress. I love how he treats me like a lady, and I adore doing little things for him that I know a man appreciates. I would have been surprised and disappointed if he hadn't complimented me on my new dress, and as always, I blushed when he told me how pretty I looked. Of course, I told him right back that he was looking particularly dashing as I took his arm while he walked me to the restaurant.

As a writer of fiction, I know how important dialogue is to keep a story alive and real, and I'd love to fill these pages with an exact transcript of our conversation over lunch and wine, but to be quite honest I hardly remember a word of it. We were just a man and a woman, chit chatting about nothing in particular - I remember that he sounded off about President Trump, whom he loathes, and I'm sure I filled him in on the latest antics of my business partners (he finds it terribly amusing that I've concealed my secret life from them for years) but nothing memorable was said, and after he picked up the check (as always - it's nice having an old fashioned boyfriend) he walked me back to my apartment.

My excitement was growing, and I'm sure his was too: two male libidos, one concealed in female guise, rediscovering their youth through wicked, kinky love. As soon as I closed and locked the door, I took off my cardigan, kicked off my shoes and sat down primly on the sofa, like a high school girl on her first date. He sat down beside me and moved in for a kiss, which I returned in kind. Kissing a guy who really knows how to kiss a girl is a wonderful feeling, and as always I sort of sat back and let him take command. His hands began to roam, caressing my legs in my silky stockings, and for a while I was content just to let him play with me while I fondled his growing erection through his trousers.

By then we were both getting pretty hot. I stood up and let him unzip my dress - having a guy unzip your dress from behind while he nuzzles the back of your neck is one of the sexiest things ever! After I stepped out of my dress, there was more foreplay on the sofa, me in my satiny slip and stockings, while I patiently helped him to get undressed. Then on to the bedroom, where at first I thought he was going to try to make love to me in my lingerie! Eventually he cooled off just long enough for me to remove my slip, then he unclasped my bra before I excused myself for a quick trip to the bathroom so I could slip into a babydoll nightie. My panties and stockings were still on too.

Then it was time for a good old roll in the hay! I think one of the reasons Bill finds me sexually interesting and attractive is the fact that my androgynous body is always wrapped in a feminine package. How many women will put on thigh high stockings and a sexy nightie for their man every time they make love? If they did, I'm sure there would be less mistresses in the world! Bill teased me about my panties - they were very cute, with a little bow on the front - before he tugged them down and began to play with his "Carina." At some point he asked me very politely if I wouldn't mind sucking him for a while, which I did with pleasure.

At our age, the fucking is part of the foreplay: when Bill told me it was time, I rolled a condom on him, lathered it up with KY, and eased myself down on him - or should I say, eased him up into me - while he lay back on the bed. He likes it this way, so he can play with Carina while I ride him like a cowgirl. I actually prefer the reverse cowgirl, because he fits into me a bit better that way, so after a while I turned around and we fucked like that for a good long time.

When we both knew it was time, I splayed out on the sheets and he took me into his mouth. Bill is one of the all-time great cocksuckers, and once again he gave me a blowjob which curled my toes in my nylons! Laying back in a sexy nightgown and stockings while man sucks me to orgasm is indescribably delicious, and when I finally came, Bill licked down every drop. I felt like the luckiest girl in the world.

Then it was Bill's turn, a little ritual we've perfected over the past seven years: I lube him up with Astro Glide and grasp his penis in a backhand, while the nails on my other hand (they're very long) scruff his nipples, and we lock into a deep, soulful kiss. Bill takes his time, sliding in and out, in and out, very slowly, very tenderly...he's not a young man, but he still has what it takes, or maybe it's because he's with me? When I finally felt him pulsing in my hand, it made me feel so wonderful to know that I'd aroused my man to orgasm!

Afterwards, I remember shrieking when I saw myself in the mirror. "What have you done to me? I look like I'm wearing a fright wig!" I brushed it out and pulled on a robe over my nightgown while Bill got dressed, then we savored our last few moments together over coffee and tiramisu. I love that man!

Then he was gone, and I realized that my three days as a woman were only half over. The rest of my stay would be - quite literally - an anticlimax! But I've always enjoyed my own company when I'm a woman, and I was actually looking forward to a little "me" time. So I went straight into the tub for a blissful bubble bath, where I reveled in the feeling of my soft, shaved skin, and the memory of the delights I'd just enjoyed in bed. When I was starting to get waterlogged, I dried myself off, reapplied my makeup (a little softer and simpler now that I was a single girl again) and put on one of my "go to" spring outfits, a tie-back blouse with blue flowers over a flouncy black skirt and pretty flats.

Tonight I was going to treat myself to a full-screen showing of an old black and white movie I've always adored: Sunset Boulevard was being featured at a suburban cinema complex courtesy of TCM. I often go to the movies as a woman - it can be a bit awkward on a Saturday night, but a single woman doesn't attract undue attention during the middle of the week. When I can go to a picture with a transgender theme - like The Danish Girl, which I saw one rainy afternoon as a woman - it's even more special.

I had some time to kill, so I went to a nearby Walmart where I scored some cologne (Revlon's Fire and Ice, I love it) water and a jar of hot fudge, followed by shoe and purse shopping at Payless and Ross (nothing was quite right) and finally bought some files at Staples for my office project. By then it was time for the move, and for the next two hours I was one of those "wonderful people in the dark" Norma Desmond reached out to...

It was getting late by the time I drove back to my apartment, but not too late for me to fire up my newly-cleaned grill and cook a steak for dinner! I relaxed with a gin and tonic and a cigarette while it was cooking, then sat down to eat my delicious steak with a green salad and a glass of Merlot. A hot fudge sundae finished my second day as a woman.

* * *

Day Three dawned sunny and lovely, the summer weather had returned at

last and it promised to be pool day! I was out the door in my jogging skirt in no time - I recently discovered that I can go out with zero makeup as long as I wear sunglasses, with a cheap old wig tucked under a visor, and nobody bats an eye as I pass them by.

I ran for a long time, then did 200 crunches to keep my girlish figure before I indulged in another bubble bath. The drudgery of shaving off all my body hair was done for this trip, but I was planning to go to the pool, so I just shaved my legs and underarms before I dried myself off, put on some makeup, and decided what to wear for a morning in the office: a sheer (almost see-through) white blouse and an electric blue skirt that I'd found on sale at Macy's, with blue kitten heels and (for the hell of it) suntan nylons.

I watched TV with my ½ grapefruit, English muffin and coffee, had a cigarette on the balcony, changed into flats and stripped the sheets off the bed which Bill had wrecked the night before. After they went into the washing machine, I headed back downstairs to the office for more drudgery. The files I'd bought the night before were perfect, and a few hours later my office looked like a secretary had been working there forever! By then my sheets were out of the dryer, so I went back upstairs to make up the bed. A woman's work is never done!

A glance at my watch told me it was almost noon, so I peeled off my nylons, scooted down to the yogurt shop around the corner for a light lunch, and returned to prepare for a conference call with my business partners at 1:00. Those who have read "A Week as a Woman" know that I've had a sometimes difficult relationship with the people who pay me, but these days things were pretty mellow. I did have one nagging issue that I'd been unable to get them to focus on: a real estate transaction that would require me to return (as a woman) if I could steer them to the right decision. A made a few phone calls to the principals before the meeting, and to make a long story short, they agreed completely, and I knew I'd be back in dresses soon! The conference call was uneventful, and by 2:00 I was ready to head for the pool

There's something about laying out in a chaise lounge in a woman's swimsuit that totally turns me on. After I settled myself a few yards away from two twenty-somethings who were gabbing away nonstop (there was much to be learned about being a girl from just listening to such conversations) I smoothed Hawaiian Tropic Dark Tanning Oil over my legs, closed my eyes, and laid back on my towel, drifting off to sweet memories of the preceding two days. When I started to get sweaty, I waltzed over to the ladder and tentatively stuck my toe into the pool, which was freezing! Too early in the year, I supposed, but the jacuzzi beckoned, so I turned on the jets and eased myself into the swirling hot water, moving from jet to jet until I found the perfect spot.

When I returned to my chaise lounge, I stretched out on my tummy, and rubbed my oiled wet legs against each other - heaven! I stayed at the pool for a long time, until after the chatterboxes left, before I returned to my apartment and selected my outfit for the night's final act: dinner as a single woman at an Italian restaurant.

One last bubble bath, before I dressed myself for dinner in a black tieback blouse, a longish, swirling skirt and strappy heels. I enjoyed a gin and tonic before I walked the two blocks to the restaurant. I was seated almost immediately, and a charming young waiter treated me like a lady as I enjoyed a half carafe of Merlot and a wonderful pasta dinner - like any girl, I asked for a takeout container to take half of it home! Then I took off my skirt and top, creamed off my makeup, stripped the polish off my fingers and toes, and packed away most - but not all - of my female finery, before I put on a nightgown and crawled into bed.