My Funny Androgyne

What will Donna Mae Trix get her girlfriend for Valentine's Day? Could a cruise be the cure for the wintertime blues? The continuing misadventures of Miss Anne Thrope. * * *

Winter in Chicago is bad enough when you're a businessman who can get away to Palm Beach or Palm Springs. When you have to put on a dress and ride the bus to your cubicle every day, you soon find out that nylons are no match for an Artic blast off Lake Michigan. For a working girl, winter in Chicago is almost unbearable.

Almost. Having a man in my life, even if my special someone was a dominatrix masquerading as a man, was enough to put a spring in my step as I went through the week in my high heels. I lived for Friday nights, when Donna would squire me to dinner and a show before I took her to bed in my little apartment. The weekends were reserved for indoor sports: sleeping till noon, cooking for two, and multiple orgasms.

I loved sex as a guy, but I loved it more as a woman. Just getting ready for a date was an erotic experience: deciding what outfit and lingerie to wear, soaking in a steaming hot bubble bath, smoothing moisturizing crème over my tender body, styling my hair and putting on my makeup. On this particular occasion, I was meeting Donna at the same restaurant where she had rocked my world by showing up as a man, and just like then, she told me to "wear something special." It was Valentine's Day, and I wondered how she had ever gotten a reservation as I cut the tags off my new dress.

My little black dress! When I spied it during my lunch hour, jammed into a FINAL CLEARANCE rack at Talbot's, my heart jumped at the prospect of wearing something so pretty. Now, after slipping on a black teddy and a new pair of ultra-sheer black pantyhose, I was quivering in anticipation as I stepped into my dress. The velvet skirt kissed the tops of my shimmering knees, and the plunging neckline barely covered my bra straps. I could almost hear my tortured penis whimpering in my panties when I nudged my silky feet into a pair of black stilettos.

When I tottered over to the full length mirror to survey the finished product, I was struck by how vulnerable I looked. With blonde hair curling down my bare neck, a hint of cleavage, a satin bow tied around my waist, gossamer legs and spiked heels, I would be easy prey without a man to protect me. How would Donna stand up to a mugger? I wondered as I fastened a velvet choker around my neck. Would she shoot him with her gun full of female hormones?

* * *

After I handed my faux fur to the coat check girl at Lawry's, I felt almost naked in my little black dress. Was it my imagination, or were heads turning throughout the restaurant as the maitre d' escorted me to Donna's table? There she was, looking smashing in a double-breasted navy blue blazer and gray flannel slacks. With her neatly trimmed beard and mustache, she looked like a sea captain as she got up from the table and kissed me on the cheek. She must have been wearing lifts in her Italian loafers, because even in my stilettos I had to stand tiptoe to kiss her back.

We were seated across from each other this time, with a flickering candle between us. Once again, Donna ordered an expensive bottle of champagne, and I waited until we were alone before asking what she got me for Valentine's Day.

"You mean you didn't get anything for me?" she asked in mock surprise.

"I'm the girl," I countered.

"Hmmm, maybe being a guy isn't so great after all."

"You'll get your goodies later on tonight, at my place. Provided you treat me right. No flowers, no candy...you're blowing it, Mister."

Instead of responding, she pulled a beautifully wrapped gift box from under the table and presented it to me with a flourish. "Will you be my Valentine?" she asked.

"The boy is just full of surprises," I said as I tore off the ribbon and wrapping paper. The box was from a boutique on Oak Street. Inside, under layers of tissue paper, was the skimpiest bathing suit I had ever seen.

"And I thought I felt naked in this dress," I said as I held it up against myself. "At least I don't have to worry about wearing it any time soon."

"That's where you're wrong," Donna said. "Take another look inside the box."

I peered under more layers of tissue paper, and spotted an envelope. "What's this?" I asked. "A gift certificate to a tanning salon?"

"Give me a little credit," Donna replied. I opened the envelope, and my heart jumped to my throat. It was a ticket wallet from Royal Caribbean Cruise Lines. Inside was an itinerary for a one week cruise from Port Canaveral to Jamaica, Mexico and Grand Cayman. The departure date was in early March. "We just have enough time to get you a new passport," she said.

A cruise! Days on end lolling on deck chairs in the tropical sun! Excursions to exotic ports of call! Formal dinners in the grand salon in my little black dress! Night after night, fucking our brains out to the rhythm of the waves! It all sounded like a fantastic dream, yet something Donna said was nagging at my subconscious. "Oh, Don, it's wonderful!" I cried. "I'd love to go, but...."

"But what?"

"Do I really need a new passport?"

"Of course you do, Anne. You already have a driver license in your new name, what's the big deal?"

My driver license in the name of Anne Thrope had been issued by court order as part of my punishment in the Metabolean class action settlement. One of the few good things about the Consent Decree which had doomed me to life as a woman for a year was a proviso that my old license would be returned to me once my year was up. "If I apply for a new passport, will I be able to get my old one back?"

I could see the hurt in Donna's eyes as soon as the words were out of my mouth. "Is that what you want?" she asked.

"I don't know...we really haven't talked about it," I stammered. We were so caught up with our new lives, neither one of us wanted to face the reality of what would happen when my year as a woman was over. Once I changed my gender to female in a sworn declaration to the federal government, would I ever be able to go back to being a man? Is that what I really wanted?

"I thought you liked things this way," Donna persisted, taking the initiative like a man.

"I do, Don. But who knows how I'll feel when I have a chance to switch back?"

"I do, because that's what I just did, remember?"

"And how would you feel about having to stay like that forever?"

"Are you kidding? I'll never go back to being a woman if I don't have to."

"See what I mean? What if I feel the same way in September?"

The waiter came to take our orders, and we both pretended to be interested in his recitation of the night's specials. Food was the last thing on our minds, and after we made the default selection of prime rib (King's cut for Donna, Queen's cut for me) we sat in silence, painfully aware of the other happy couples sharing their love in the crowded restaurant. Donna just stared at me, as if saying, "We have such a good thing going, baby. Please don't screw it up."

Part of me wanted to scream, "Please take me on the cruise! Take me anywhere you want to!" Just the thought of escaping from the Chicago winter for a week was enough to make me want to say yes. A whole week without getting up before dawn to wash and style my hair, put on my makeup, gussy myself up in a dress, heels and stockings to freeze my ass off on the way to my bus...what was I thinking? But another part of me was desperately afraid that I was being sucked deeper and deeper towards the point of no return. After all, Donna was a professional dominatrix. How could I be sure that this wasn't just another of her elaborate psychological games, designed to break my will and doom me to a lifetime as a woman?

Our salads came, and we picked at them listlessly. Finally Donna broke the frosty silence. "Do you remember what I promised you on Christmas Eve?"

"You told me that you would go back to being a woman if I went back to being a man."

"Well, the offer still goes. What hurts more than anything is that you won't even consider doing the same for me."

"I'm not sure that's what I really want. Oh Don, I'm so screwed up right now!" I felt tears dripping down my cheeks.

She reached over with her napkin and gently wiped my face. "Your mascara is a mess," she said with a half smile. "I'd go into the ladies room with you, but I don't want to start another Valentine's Day Massacre in Chicago." I tried to laugh through my tears, and she got up and pulled back my chair. I picked up my clutch purse and hurried towards the lounge.

There was a line, of course, and the girl standing in front of me surveyed my face. "Bummer! Breaking up on Valentine's Day?" she asked.

She was cute, short and blonde, the kind of girl I would have lusted after when I was a guy. Now, as I followed her into the ladies room after two women walked out together, I could only sigh at how much my life had changed. Standing side by side in front of the full length mirror, I saw her lift up her skirt to fuss with her panties and hose. In times gone by, I would have wanted to grab her ass. Now I was rummaging through my purse for a tissue to fix my makeup. Is this what the rest of my life was coming to?

"How about some sisterly advice," the girl said.

"I think I can fix it okay."

"I don't mean your mascara, I mean your man. Let me take a wild guess that you're breaking up with him, only you're not one hundred percent sure you're making the right move. Well, he brought you here for Valentine's Day, didn't he? Do you know how many girls would kill for a guy who would put on a coat and tie and take them to a place like this?"

"You don't understand."

"What, you have 'issues' with him? Let me tell you a little story about a guy who was head over heels in love with me, and treated me like a queen. After we started living together, one day I came home early from work and found him parading around our apartment in my panties. So I dumped him, right? Well, get this – today he's married with two kids, living in a mansion in Winnetka, and I'm here on Valentine's Day with a Viagra poster boy who's cheating on his wife. Take it from me – if you find someone who makes you happy, never let him go." Then she was gone, before I could respond.

I felt terribly alone as I stood there, fixing my makeup and brushing my hair. There I was, pretending to be a woman, while the only person I had ever really loved sat waiting for me, pretending to be a man. What if we were the only two people in the world, and we could switch back and forth whenever we wanted to? If we really were soul mates, did it even matter? Suddenly I knew what I had to do. I rushed back into the restaurant, looking around for my new friend and her sugar daddy to thank her, but she was nowhere to be seen. I thought nothing of it at the time.

I returned to our table to find Donna waiting patiently for me. Our dinners had been served, and she waited until I sat down before lifting her fork. "Such a well-mannered gentleman. I guess growing up as a girl was good for you. They're going to be so impressed at the Captain's table."

"Does that mean you'll go on the cruise with me?"

"Of course, silly. As a very wise person once told me, 'If you find someone who makes you happy, never let him go.' If becoming a woman is what it takes to make you stay, then I'll put up with all of the hassles, but you're gonna owe me big time, buddy."

That night was incredible. After we got back to my apartment, Donna slowly undressed me, kissing each new place as my skin was unveiled. Soon all I had on were my teddy, panties and stockings, and she paused to lovingly peel the nylons off my legs before she stripped me bare and went to work with her tongue and fingers. Have you ever experienced simultaneous male and female orgasms? Had your penis sucked while your ass was penetrated until you were racked with spasms of unimaginable ecstasy? Donna did that to me again and again, and when it was over, I would have been content to live out my days as a woman if it meant all my nights would be like that.

* * *

I could hardly believe it when my alarm clock went off at six o'clock the next morning. Donna must have let herself out after I finally fell asleep, and when I dragged my naked body into the bathroom to turn on the shower, I was stunned by my reflection in the mirror. My hair was a tangled mop, my face was streaked with makeup, and there was a vicious hickey halfway up my neck. After I shampooed and conditioned my hair and soaped my tender skin under a hot shower, I dried myself off and went through the now-familiar motions of styling my hair and putting on my makeup. The hickey was still visible despite my efforts to conceal it.

I rummaged through my closet for the knit dress with a turtleneck collar that would hide my hickey. It was very short, but I had no choice. After putting on my lingerie, nylons and dress, I glanced at the clock and saw that I was running late. The stilettos that I'd kicked off on my way into bed lay on the floor where I left them, and without thinking I put them on, dumped the contents of my clutch into a matching purse, pulled on my coat and raced for the door. Normally I stuffed my heels into a shoulder bag and wore long socks and sneakers on the way to work, but there was no time for that today. I fished my scarf and gloves out of my coat pockets on the way to the elevator, and by the time I was out on the sidewalk, I had to sprint in my heels to make the bus. It was barely above zero, and my legs were purple by the time I got to the bus stop. Fortunately, my bus got there at the same time I did, and I was able to grab the last seat as we lurched off.

Another day, another dress, I thought to myself. Life at the office had settled into a surreal routine, in which my former colleagues pretended not to notice that I was dressed as a woman, and my former underlings did their best to accept me as one of their own. I was just firing up my computer when Gladys poked her head into my cubicle. "Big night last night?" she asked.

"I must look like shit."

"Far from it! You have the glow of a woman in love." I felt myself blushing. "I just came in to tell you that Mr. Sharkman's Executive Assistant is off this week, and he wants you to take down the minutes of his weekly staff meeting. It starts in five minutes."

Just what I needed! All of my old direct reports would be in that meeting, along with Dick Sharkman himself, the womanizing creep who had hit on me at the office holiday party. I grabbed my steno pad and made a quick stop at the ladies room to freshen my lipstick and straighten my hair before walking into the lion's den.

"Good morning, Anne," Sharkman said with a thin smile when I entered the crowded conference room and began looking for a seat at the long table. "Why don't you sit here," he said, pointing to a chair against the wall, next to table laden with coffee and muffins. Of course – that way they could look up my dress! I sat down awkwardly, tugging my hem down towards my knees while every man in the room stared at my legs. I crossed them carefully and perched my steno pad on my silky thigh.

"Anne, could you freshen up my coffee, please?" a snotty junior executive asked.

"Me, too," another one said, and then another. I could feel their eyes following me as I stood up and walked over to the coffee table in my stilettos. It was impossible not to walk like a bimbo in those heels, and I could only imagine what they must be thinking about their former boss as he bent over in his short dress to fill their mugs. When I was finished, I returned to my chair, and caught several of them smirking as I crossed my legs and pulled my dress down. Mercifully, Sharkman turned down the lights to make a power point presentation about a new product in development, and the rest of the meeting passed without further mortification.

After the lights came back on and the meeting broke up, I waited for my former colleagues to leave, looking down at my pad and pretending to study my notes. When only Dick Sharkman remained, I got up and headed for the door. "Oh, Anne," he said, "I'm leaving for L.A. first thing tomorrow morning. Could you please have the draft minutes ready for me before you go home tonight?"

I looked down at my scrawls on the steno pad. It would take me hours to decipher my own handwriting and type of something presentable, and I knew Sharkman was just trying to get a rise out of me, but something inside me refused to give him the satisfaction. "Yes, sir," I said. I could feel his eyes boring into my back as I minced out of the room.

Gladys intercepted me on my way back to my cubicle. "How about some lunch?" she asked. "There's a big sale at Marshall Fields if we hurry."

"Sorry, I'm swamped. Mr. Sharkman just dumped the minutes on me – he wants them before he leaves for La-la-land tomorrow."

"I've been there. He'll hang around tonight waiting for you to finish them, and when everybody else has gone home and you're still slaving away, he'll ask you out to dinner."

I was gobsmacked. "You gotta be kidding. Unless you're telling me he's gay."

"Well, not exactly. But I did find out from one of the MIS guys I'm dating that Mr. Sharkman has been visiting some very interesting web sites."

"Omigod. You mean like 'Chicks With Dicks?'"

"Exactly. It seems he has a thing for girlie men."

"Can't he get fired for visiting sites like that on company time?"

"Dear, sweet, innocent Anne...he's an exec, remember? Those rules are only for us peons."

With a shake of my head, I bent over my keyboard and began the tedious process of transcribing my pathetic "shorthand" into some semblance of what went on during the staff meeting. Gladys brought me a bowl of soup and some crackers when she got back from lunch, and I was surprised to see her coat covered with snow. "It's a blizzard outside," she said. "Good thing you don't live in the burbs." I thanked her and returned to my screen. After hearing about the weather, I felt cozy in my little cubicle, and my thoughts drifted to Donna as I kicked off my heels and tucked my legs up under my skirt. The hassles of being a woman seemed a small price to pay for the ecstasy we shared together, and in a few weeks, we'd be basking in the tropical sunshine. I thought of calling her to whisper a few obscenities, but I had no privacy, so I thought the better of it.

The hours flew by as the minutes took shape, and at a few minutes before five, I printed them out and put on my stilettos to take them to Sharkman. Most of the staff had already gone home after the office manager closed the office early on account of the snowstorm, and I encountered no one on my way to my old office. Sharkman was hunched over his computer screen, and he didn't see me when I approached his desk. When he heard me place the minutes in his inbox, he sat up with a start, and I couldn't help but see the image of a girl with an enormous penis on the web site he'd been secretly browsing.

Sharkman tried to act nonchalant as he switched off his computer, no doubt hoping that I hadn't seen what I'd seen. "That was fast work, Anne," he said smoothly as he perused the minutes. "These are excellent." He waved at the expansive windows in the corner office. "It's pretty nasty out there. Can I give you a lift home?"

I weighed the misery of slogging through the snow to wait for a bus in my short dress and high heels against the humiliation of being dropped off at my crummy apartment in Dick Sharkman's company car. What if he hit on me when we got in the car? It would be his word against mine. "No, thanks," I replied. "I can't compete with your virtual girlfriends."

"What do you mean?" he asked nervously.

"I don't think you could give me a hard-on if my life depended on it. And Mr. Sharkman, I'd be careful about those web sites you're visiting on the network server." I spun on my heel and got halfway back to my cubicle before I felt him grab my arm.