As I write these memoirs, my deeply tanned legs are stretched out before me on a lounge chair on my lanai. My pink toenails provide a nice contrast to the aquamarine sea visible in the distance, framed by swaying palm trees on golden sands. I brush a strand of hair from my forehead, and tug my sundress a few inches towards my knees.
Looking back, it’s hard to believe that a mere month ago, I was a hunted man with a price on his head. How I got from there to here would be a front-page story on every newspaper in America, and would land me in jail if it became known to the authorities. Which explains why I intend to seal these memoirs in bottle and throw them into the sea, for discovery long after I have lived out my life as a beautiful, wealthy woman.
* * *
It all began when Oregon legalized marijuana in 2014. A recent graduate of Oregon State, I landed a job in IT with a start-up which applied for one of the licenses to sell marijuana, and at first it seemed like a legitimate business. However, before long it became clear to me that my employers had been growing and distributing marijuana illegally for years, and their prospects of securing a license became dim after an expose on KOIN, the Portland affiliate of CBS.
Unfortunately, shortly after the negative news story on my company came out, I was observed by our Director of Security having lunch with a college friend, who happened to be an intern at KOIN. He came to the wrong conclusion that I was a snitch, which to the company’s owners justified the death sentence. I learned this by chance when I was working late one night (from my home, thank God) and after I came across some worrying email traffic, I penetrated the CEO’s email address and quickly learned my intended fate: I was to be assassinated the next morning while waiting for my TriMet train!
Stunned at the realization that I had less than twelve hours to live, I tried to survey my options. At first I thought about going straight to the police or the FBI, but I quickly realized that would only confirm my employers’ suspicions and mark me for death sooner or later. No, I had to get far away fast, and with that realization, the germ of an idea came into my mind: these were bad people who had made millions of dollars illegally pushing drugs, so why not relieve them of some of it on my way out the door? It didn’t take me long to hack into their bank accounts, which sure enough I found to be loaded with cash, waiting to be laundered. With a few keystrokes, I transferred three million dollars into my own bank account.
So I’d be rich, if I could afford to spend it. It was early spring, and a news story I’d seen that morning popped into my head: hiker disappears on Mount Hood, intensive search underway. Up on the mountain, it was still winter, with weather conditions that could change drastically from minute to minute, feet of snow still on the ground, and another snowstorm on the way. After a few moments of thought, I tapped out an email to my boss, informing him that I’d decided to take the next day off for a hike on Mount Hood.
One final email before I packed my hiking gear into my car: I told my friend at KOIN to watch his back! Then I loaded up my Subaru and pulled away from my apartment a few minutes after midnight. I drove to Government Camp, paid for a motel room with my credit card, and spent a restless few hours waiting till morning. After breakfast at a local café, again paid for with my credit card, I walked over to the local branch of my bank and shocked the branch manager by withdrawing three million dollars in hundreds. I took my time jamming the bills into an oversized backpack, which weighed over 60 pounds by the time it was full, and headed for the mountain.
I parked my Subaru at the trailhead for a climb that was notoriously treacherous, heaved my backpack onto my back, smashed my cellphone and threw the bits into a ravine, and did the exact opposite of what my pursuers and the authorities would expect: I started hiking down off the mountain. It was a lovely spring day, and I hardly felt the burden on my back as I made my way down towards the road which led to the freeway. When I got close to the highway, I pulled a ski cap low over my ears and forehead, and pulled the collar on my jacket over my chin. With my wraparound sunglasses, my facial features were now extinguished. I stuck out my thumb, and before long I was sitting beside the friendly driver of a logging truck, bound for Idaho.
* * *
Without fake ID, leaving the United States was out of the question, but it’s a big country. As we rolled east, I closed my eyes, and while pretending to sleep to avoid conversation with the driver, I tried to think of the safest way to set myself up with a new identity. Faking my death had been the easy part: when I did not come off the mountain and my car was found at the trailhead, a massive search would undoubtedly ensue, and when no trace was found of me, I’d be chalked up as just another luckless hiker who’d been caught in the blizzard that was bearing down on the Cascades. It wasn’t uncommon for bodies to simply vanish, to be found years later when the snowpack melted.
No, the bigger problem was how to disappear with three million dollars and never be found. As fate would have it, both of my parents had predeceased me in separate automobile accidents, and my only sibling – a sister – had gone bad and run off with a creep somewhere in California. I had a few college friends who might mourn me briefly, but no responsibilities and no ties to speak of.
Where shall I live and who shall I be? Could I make myself unrecognizable and pass through life as a totally different person? Keeping alive and staying out of jail – for surely it was a crime to steal three million dollars, even from drug dealers – depended on it.
* * *
Two days and many trucks later, I found myself on the outskirts of Chicago. I hitched a ride into the city with a traveling salesman, and paid cash for a dreary room at a no-tell motel near O’Hare airport. After sleeping for fifteen hours, I walked to an all-night diner – it was almost dawn – and bought a Chicago Tribune to read while I waited for my bacon and eggs. Sure enough, buried deep in the first section I found this article:
MANHUNT CONTINUES FOR MISSING HIKER
PORTLAND – The U.S. Forest Service and the Oregon State Police have resumed their search for XXXX XXXXXXXXX, who disappeared during a record-setting snowstorm while hiking on Mount Hood. The search was temporarily suspended during the height of the blizzard, which dumped over three feet of fresh snow on the already snow-packed mountain. XXXXXXXX’s car was found at a trailhead leading to a popular hiking trail two days ago, and his cellphone has presumably run down. Volunteers from Sandy and Government Camp are assisting in the manhunt.
I felt badly about the volunteers, and the expenses that the government must be running up, but these feelings quickly vanished when I came across another, shocking story:
NO CLUES IN MURDER OF KOIN INTERN
PORTLAND – Police remain baffled by the cold-blooded killing of Andrew Moffatt, a twenty-two year old intern at KOIN who was shot to death in broad daylight two days ago when he walked out of the station’s broadcast studio in downtown Portland. Moffatt, who was on his way to pick up coffee for fellow staffers, was shot five times in the back, and died on the sidewalk before an ambulance could arrive.
My hands were shaking as I dropped the newspaper. Poor Andy! He didn’t even know about the drug dealers who were after me, and now he was dead. Why couldn’t I have given him a better warning? What did I say to him when I tried to tip him off? “Andy, watch your back, some bad people may be out to get you.” When the cops got ahold of that, would they connect the dots with my disappearance and speculate that I’d been murdered too? My whole life was turning into a nightmare!
One thing was certain: the people who gunned down Andy were looking for me, and if I was foolish enough to go back to Portland to tell the police what I knew, they’d undoubtedly kill me too. There was no choice for me now but to lose myself forever, and with three million dollars in cash I had the means to do it, if only I could figure out how to hide in plain sight for the rest of my life….
My breakfast came, and as I listlessly played with my scrambled eggs, another article in the Tribune caught my eye. It was about Caitlyn Jenner, and how her revelations about her gender transition had become a topic of national conversation. It was an Aha moment: why couldn’t I turn myself into a girl? That was the last thing my killers would suspect, and unbeknownst to them, or anybody else who knew me, I already had some practice: my older sister used to dress me up in her clothes when we were kids, and after she ran off with her loser boyfriend, I used to fool around in her closet when nobody was around. I was fascinated by the way I looked in a dress or skirt, and I loved putting on her nylons, which was a strange turn-on for me….
Until I went off to college, I’d never gone outside the house as a girl. For my first two years, roommates made it impossible for me to even think about crossdressing, but my last two years I lived alone in a small apartment, and I found myself tempted to get back into it. By then my sister had disappeared, and when my mother asked me to help her clear out her closet while I was home for summer break, I surreptitiously stashed a small wardrobe including lingerie and tights, and even some of her makeup, in a large box which I hid until it was time for me to go back to college.
I never shared my secret with anyone, which was easy since I made very few friends. A geek majoring in computer science, I pretty much kept to myself, and the few girls who agreed to go out with me always seemed to have other plans when I asked them out again. So I’d get my kicks dressing up in my sister’s clothes, although I rarely left my apartment like that, and I wondered if I’d really be able to pass as a woman? I was lucky with my physique: 5’8” tall, a mere 145 pounds, a full head of long brown hair and skinny arms and shoulders. Instinctively, I pushed my breakfast plate away as I began to think: you’ll have to lose at least ten pounds to be truly believable as a girl, I told myself, and you’ll have to start putting together a look.
You must think I’d lost my mind. Fooling around in girl’s clothes in my spare time was one thing, but did I really want to live the rest of my life as a woman? Did I even think that I could fool people if I put on some makeup and wore a dress? Maybe not, but at that point, the hassles and humiliation of trying to turn myself into a girl paled in comparison to the fate which awaited me as a man. It might not be the life I wanted, but I’d be alive, and with three million dollars to play with, I could afford a life of luxury if I was able to complete my transformation.
I had a lot of work to do, and for the moment, my flophouse motel would serve as my base of operations. I was a little concerned about leaving my backpack stuffed with millions of dollars in the room, but that was a risk I’d have to take. I removed a few thousand dollars and jammed the backpack between the dust bunnies and cobwebs under the sagging bed. Only a desperate thief would even think about looking there….
I walked a few blocks to the Blue Line, and assembled my thoughts on the way into downtown Chicago. My first stop would be at a large drugstore, then I’d try to find an Internet café, before I could start thinking about hair, clothes and makeup. The train pulled in to the Washington Street station, and I soon found a Walgreens, where I purchased a prepaid Visa credit card in the amount of $500 and a throwaway cellphone.
Then it was off to a FEDEX office store, where I hunkered down at a personal computer and swiped my new Visa card. After a quick scan of the Portland headlines – the hunt for the missing hiker on Mount Hood had been suspended again after another blizzard moved in – I created a new Internet address for myself using an androgynous name: Kim Drake, screenname [email protected]. Next, I scanned the Craigslist pages for Chicago, looking for the cheapest reliable used car that I could find. I spotted a 2007 Ford Focus SE Sedan, asking price $1,950, for sale by owner in Elmwood Park. I sent a message, using my new email address, then turned my attention to creating a fake Illinois driver’s license.
I’m ashamed to say it didn’t take me long. Downloading a sample from the DMV website, I used it as a template, duplicating the multiple typescripts with various fonts, inventing a date of birth and address for Kimberly Drake, sex female, finding a copy of the state seal, uploading an old picture of me with long hair that looked just girly enough, and printing the whole thing on some watermarked paper. Once I signed it in a girlish hand, sealed it between two sheets of laminate and trimmed the edges, it would fool anyone on visual inspection, although it didn’t have a bar code or other security features so it would be useless at an airport. One final touch: a dab of whiteout over the letters FE, to be brushed off later….
Before I left, I checked for email messages at my new account. The owner of the Ford Focus had replied, leaving her phone number and asking me if I was still interested. I called her with my new cellphone immediately, and we made arrangements to meet at a strip mall near her home in half an hour. I flagged down a taxi to Elmwood Park, and killed some time browsing at a Payless shoe store until she showed up with her boyfriend, who was driving another car.
They both looked like meth addicts, and under ordinary circumstances I wouldn’t have had anything to do with them. After a cursory inspection of the beat up Ford, I asked them if they had the pink slip, and the lie which the boyfriend stammered about being unable to find it was so transparent that I was certain that the car was stolen. That didn’t matter to me: my plans were to take it on a one way trip out of Illinois, as soon as possible. The boyfriend launched into a sales pitch, but I cut him off when I handed him two thousand dollars in cash and told them to keep the change. Before they could think of anything else to say, I took the keys and drove off.
Back to my crappy motel, where I parked the car and returned to my room. My stolen millions were still under the bed. I called the front desk to tell them I was checking out, threw my backpack in the trunk and headed for the freeway.
* * *
I drove south, stopping only for gas, for over a thousand miles before I finally pulled over at a luxury hotel on Tampa Bay. No more fleabag motels for me: hotels like this required identification, and my new driver’s license passed easily. Would its owner be able to pass as easily as a woman? Tomorrow would tell, but tonight I spent my last night as a man, drinking a little too much red wine with my steak dinner before I staggered off to bed.
I slept in the next morning, arising just before noon. After a light breakfast, I drove my beater to a nearby “mile of cars” and parked it on the street. With my backpack on my back, I surveyed the lots of the luxury car dealers before I found myself drawn to an Audi S5 convertible. I was inspecting the sticker when a car salesman approached me, probably assuming that I was a kid hitchhiking back to college. Before he could run me off, I told him I wanted to take it for a test drive. He started to laugh, until I told him that I was prepared to pay cash if he could have the car prepped and ready to drive off the lot in an hour. The test drive was a formality – what a machine! We haggled a bit on price, I showed him my fake driver’s license, the paperwork was completed in record time and I drove off the lot with the top down.
My first stop was another Walgreens, where I loaded up on prepaid Visa cards and took the first tentative step in my transformation: an old fashioned double edge razor with plenty of blades, and a mangroomer with a long handle so I could take the hair off my back. I returned to my hotel, and while the mangroomer was charging up, I filled the bathtub with hot suds and patiently shaved my arms, legs and chest. It was a nasty process, and I cut myself several times, but when I was finished, my body was already looking more feminine, and it felt that way too after I smoothed my tender skin with the hotel’s body crème. After I took care of my back with the mangroomer, I dressed myself as a man for the last time, and drove my new Audi to a nearby outlet mall.
I’d made a shopping list at breakfast that morning. If I was going to live as a woman, I was determined to be as pretty as possible, and to try to get away with the same undergarments that real women wore. It was April in South Florida, and soon it would be hotter than hell, and I wasn’t about to bind myself and pad myself for the sake of a few inches. I had a girlish waste, and slim arms and legs, and I’d count on them to help me cross the bar.
I’ve kept my list, and it brings back bittersweet memories every time I look at it. My success in avoiding assassination and imprisonment would come at the price of my manhood:
Skirts
Tops
Sundresses
Shorts or capris
Sandals
Heels and/or flats
Purses
Wallet
Panties
Wonderbras
Pantyhose
Bling: clip earrings, rings, necklaces, watch
Nightgown
Robe, slippers
Makeup: lip gloss, eye liner, eye shadow, brow pencil, blush, foundation and powder
Moisturizer
Nail polish
Cologne
Hairbrush
I scratched pantyhose off my list: this was Florida, and this was for real, not some crossdresser’s fantasy. It was exhausting just thinking about the challenges which lay ahead, but the alternative was an early grave. The sooner I buried the man that I was, and started thinking of myself as a woman, the better my chances of survival. Fortunately, from my days as a closet crossdresser I knew my sizes (the same as my sister’s) so there was no mystery involved. The first step would be the hardest.
* * *
Hours later, I collapsed onto the bed of my hotel room after dragging dozens of shopping bags from my car. What an ordeal! Two skirts and one pair of skimmer shorts, three tops, two sundresses, a couple of wonderbras, several packs of panties, a slip, some cute jeweled sandals, white espadrilles, two pair of strappy heels, three purses, a small pile of fashion jewelry from Claire’s, and a darling nightgown with spaghetti straps and a matching robe. To each of the sales clerks, I’d explained that I was shopping for presents for my girlfriend, and except for the shoe store, they might have believed me. Getting the cosmetics was not as embarrassing as I feared: at a nearby WalMart, I filled a basket with everything I needed and waited for an opening at the self-service checkout line. I got my quota of embarrassment at my last stop: a Supercuts, where I asked the girl to try to recreate the boyish bob that Caitlyn Jenner styled when she was still Bruce…I’m sure the girl saw right through me, but she played along, and every time she asked me a question about which way to go, I went with the more feminine alternative.
From now on, I told myself, it’ll be a lot easier, since you’ll be shopping for yourself as a girl. With a sign of resignation, I pulled the tags off a skirt and top, tore off my guy clothes, and went into the bathroom to shave my face and legs again. After a long, hot bubble bath, I was ready to start in on my makeup. I used to be pretty good at this, using my sister’s hand-me-downs, and I was pleasantly surprised by the natural look I was creating, using the bare minimum of each product.
After I’d filed and polished my nails, I returned to the bedroom to snap on a Wonderbra, which instantly gave me the illusion of female breasts. Next, I slid on a pair of panties, and when I did, for the first time I felt a trace of arousal. Oh oh….down boy, I said to myself as I stepped into my skirt, a billowy confection of eyelet lace which felt delightful against my legs. Those forbidden feelings intensified…not now! I scolded myself while I dropped my sleeveless top over my head, and the wicked sensations momentarily eased while I busied myself tying a bow behind my back. Then I stepped into my espadrilles, which made my feet look so cute!
A glance at myself in the mirror on the back of the closet door took my breath away. For the first time in my life, I liked what I saw…this wasn’t me fooling around in my sister’s clothes, this was the woman I was going to become, living in her soft skin for the rest of my life, in pretty skirts and dresses like this…I didn’t want it to happen, but my body slowly surrendered to a surprise orgasm, flooding my new panties as I whimpered in ecstasy. The feelings were so sweet, and so strong, like nothing I’d ever experienced, and I just gave in to them and let myself ride a wave of intense, exquisite pleasure that went on and on and on….
Then it was over, and I lay flat on my back, staring at the ceiling. Is this what I could expect every time I got dressed in the morning? Surely not – over time, putting on women’s clothing would become second nature to me, otherwise my body would wear itself out! Too bad, I thought ruefully….in truth, I hadn’t had an orgasm in a long time, and a lot of pent-up testosterone just went out of me. Good thing I had plenty of panties! I lifted up my skirt, took off my sodden panties, wiped myself down with a bath towel and put on a fresh pair. This time, my penis tucked obediently between my legs, and I hoped it would behave itself – for a while.
* * *
That afternoon, I went on some errands, my first real outing as a woman. In college, I’d walked around the block a few times after dark, but I was always terrified and never encountered anyone. As a precaution in case I was stopped for some traffic infraction or had an accident, I tucked my real driver’s license in an inside pocket of my new women’s wallet, with my fake license displayed on the outside. And in case I was mugged and lost my purse, I stuck an extra hotel key inside one of my shoes – a girl couldn’t be too careful! I drove carefully, shielding my eyes as I added yet another item to my growing shopping list: sunglasses. It was amazing how many little things a woman needed just to get through the day, and by the time I got back to the hotel, I was beat.
So I stripped off my skirt, top and lingerie and treated myself to another bubble bath. Heaven! After I reapplied my makeup, I decided to put on one of my new sundresses. It was black, with little yarnbows on the shoulders, and it was unlined so I was glad I’d bought a slip to wear under it, which felt sinfully delicious against my skin. After I dropped my dress over my head and strapped on my new heels – that took some getting used to - I put all my girl stuff in a different purse which matched my dress, slung it over my shoulder and walked to the hotel restaurant, a little wobbly in my new heels.
A single woman alone at a fancy restaurant is an oddity, but fortunately I had a very friendly waiter, a young man about my age who was terribly good-looking. He smiled at me when I was seated at one of his tables, and produced my menu with a flourish. What followed was one of the most memorable nights of my life.
I’m sure you’ve noticed that so far there has not been a word of dialogue in these memoirs. That’s not entirely by accident: when I went on the lam, I kept my mouth shut so as not to reveal my identity, and after I made the jump from boy to girl, I’d been very cautious about speaking to anyone, for fear that my voice would be too deep and might give me away.
Anyway Randy – my waiter’s name, according to the tag on his uniform – was naturally charming, and when he told me how much he liked my dress, I started to giggle. Giggle like a girl.
“What’s so funny?”
“I got it at the outlets today for $19.” My female voice came naturally, very soft and sweet, and I started to relax.
“I’ve finally found the perfect girl.”
“Hardly,” I said. What an understatement! I might look, and sound, like a girl, but under my $19 dress….
“No, I mean it. Pretty, smart and sensible. Where have you been all my life?”
Did he really think I was pretty as a girl? “You’re making me blush.”
“Please don’t! It’ll hide your freckles, which I find irresistible.”
My God, he was flirting with me! “You do?”
“Of course. What can I bring you to drink?”
What did a woman drink? “How about a glass of your house Chardonnay?”
“Coming right up.” I tried to compose myself after he left. I’d never been attracted to a man in my life, and now, on my first day as a woman, I felt my pulse racing. When he returned with my glass of wine, I felt a little spike in my panties too.
“Thanks.” I took a sip while he stood patiently beside my table. “This is lovely.”
“The swordfish is excellent tonight.”
“Sold. Can I start with a Caesar salad?”
“Surely. Excellent choice.” He left me to my wine, and I felt a little buzz as it went to my head.
By the time Randy returned with my salad, my glass was almost empty. “So what’s a pretty girl doing here all alone tonight?” he asked.
“Getting quietly bombed. Another glass of your lovely Chardonnay please.”
“Coming right up. Only you have to tell me more when I come back.” Tell him what? That I was really a man? That I was a fugitive, with drug dealers on my tail and millions of dollars in stolen cash in my room? Or how about this: “Do you make it with girls who are really boys?” That would be a show-stopper, all right…maybe he was really gay, and he’d seen through my disguise? Or maybe he was just a straight guy who had a little thing for chicks with dicks?
My Caesar salad was delicious, and as I sipped the remains of my first glass of wine, I allowed myself to revel in my good fortune: I was alive, in a warm, sunny place, with all the money I’d ever need. And I’d turned myself into a girl, a pretty girl who men like Randy found attractive. Still, it was only half a life, and it was going to be a very lonely existence, unless I could find someone to confide in. Was Randy that person? I’d only known him five minutes, and already I was thinking about confiding my innermost secrets to him! What kind of a silly little girl was I turning myself into?
Randy returned with my Chardonnay, and I decided to take a direct approach. No use stringing him along if he was going to freak out when he found out I was a guy. Nobody in the restaurant knew who I was, and I was checking out of the hotel tomorrow, so why not go for it? After all the traumas I’d been through over the past week, what was one more? No doubt the wine was getting to me.
“So Randy,” I asked before he could say anything, “have you noticed anything…special about me?”
“Hmmm…” he said as he stood back and framed my face with his hands. “You have beautiful blue eyes, cute hair, those freckles I’ve already mentioned, and the first thing I noticed when you walked in are those killer legs. Other than that, you’re a dog,” he smiled.
I felt that spike in my panties again! “If I didn’t know any better, I’d suspect that you’re trying to get into my panties tonight.”
“She’s onto me,” he said as he watched me sip my Chardonnay.
“And what if you were to find a secret in those panties?” I looked up at him and studied his face, which had a blank expression. He was working it out…then he broke into a shy smile, and he leaned over and whispered, “If you’re trying to tell me what I think you’re trying to tell me, I think I want to find out.”
* * *
The rest of that evening is a blur, until Randy knocked on the door of my hotel room. I’d taken off my dress and put on my sexy new nightgown, and when Randy came in, I did a nervous twirl for him. “Do you like what you see?” I asked him.
“I want to see your secret,” he said before he lifted my chin and gave me a little kiss.
“In due time,” I answered after I curled up on the bed.
“So have you ever made it with a girl like me?”
“No, never. But since we’re sharing secrets, can I tell you one of mine?”
“Sure.”
“Sometimes I wonder what it would be like…I mean sometimes I think about how I’d look…shit, why is this so hard to say?”
“You wonder what it would be like to dress up as a girl. Believe me, I get it.” He was still standing next to the bed, and I framed his face with my hands, like he’d done to me at the restaurant. “Well, let’s see…you’ve got a cute face, your nose isn’t too big, and with a little makeup I think you’d make a pretty girl. But you’re so tall! Big and strong doesn’t translate into sugar and spice….”
“That’s what I was afraid of. You must think I’m kinda creepy.”
I patted the bed next to me and he sat down awkwardly. “No, I think you’re gorgeous.” I lifted his chin and returned his kiss. It felt nice…no, it felt great, and my penis was raging in my panties. I reached down and felt him through his trousers, and he was hard as a rock. One thing led to another, and before long I had him undressed, and he was tugging my panties down to my knees. I can’t remember who started it, but soon we were kissing each other’s penises, and the sensation of tasting his pre-cum while he sucked on me was like nothing I’d ever experienced, sheer, utter lust that consumed us both as our arousal peaked and we came simultaneously in each other’s mouths, wicked orgasms that felt – and tasted – so damn good!
We lay there together in each other’s arms for quite some time, neither of us saying a word, until Randy finally spoke. “Baby, that was the best I’ve ever had. I guess this makes me gay,” he added.
“Not necessarily. I mean, you definitely just made it with a guy, but I’m a girl too, so I’m not feeling especially gay at the moment. More like a woman who just gave her first blowjob, and kinda liked it. Of course, the fact that you gave me one too made it pretty amazing.”
“So what you’re saying is, we’re both fucked up.”
“Exactly.” He kissed me, a deep, romantic kiss that started me stirring again, and I felt him stiffening too, and we stroked each other for a while until we were both hard again. At first I thought he was going to go down on me again, until he pulled a condom out of his pants pocket on the floor. “This will be a night of firsts,” I said.
“You mean you’ve never made it with a guy before?”
“Sweetheart, I’ve never made it with anybody before.”
“Wow, a virgin. And my first ladyboy. How do you want it?”
“Huh?”
“What position? Missionary? Doggie style? Reverse cowgirl?”
“Goodness…are you sure I’m your first?”
“You’re my first boy. Here, stand up and lean over the bed.” I did as I was told, and he gently pushed me down and stood behind me. “I’ll be gentle,” he said, sensing my apprehension. I felt his penis probing my ass cheeks (which tickled) then he bore down and inserted the tip inside me. I gasped at the shock of penetration, it hurt! But he held me down by the shoulders and kept on driving, in and then out, a bit deeper each time, and I opened my legs a little more and bent my knees as I tried to rock with his rhythm, in and out, in and out, faster and faster until I could sense that he was getting ready to cum. I don’t know when the pain turned to pleasure, but by the time he was ready, I was in a fit of ecstasy from the raw, pure pleasure of having a man inside me, and then he reached around and grabbed my quivering cock, which he stroked tenderly while he exploded inside me, which in turn made me cum too, a mind-bending orgasm that I felt down to my toes as he continued to slide in and out of me, until we were both spent, and we collapsed onto the pool of semen on my bed.
We lay that way forever, it seemed, until Randy’s breathing returned to normal and he rolled off me. “Wow,” was all he said.
“Was it good for you too?”
“Are you kidding? That was the best I’ve ever had. Even if it means I’m gay.”
“But you’re not. Because I’m a girl. Which makes you bi, I guess. And me too.”
“Bi. I like that. Yeah, I like that a lot.”
* * *
After Randy got dressed and left, I tossed and turned for a long time. I’d just had sex, amazing sex, with a man. And I loved it! It was hard to believe that less than 24 hours ago, I didn’t own a stitch of women’s clothing, and now I was not only living as a woman full time, but I’d just had fantastic sex as a woman, in a way I’d never experienced as a man. All of my troubles back in Oregon seemed far, far away….
The next morning, after shaving my legs again in another long, lazy bubble bath (I was becoming addicted) I put on my makeup and dressed myself in my other new sundress, which felt light and lovely against my freshly shaved skin.
I wondered if Randy would be serving breakfast in the restaurant? He was nowhere to be seen, and it occurred to me that I was probably going to be just another one night stand for him, one of his many conquests, with a little twist in my tail. Which was okay, I had no complaints! Although I wished I could see him again to say goodbye. I’d given him my new email address and cellphone number, but chances are he’d tossed them after he left me, probably feeling a little sheepish about making it with a Tgirl, which is what I was. Oh well….
One of my acquisitions when I went out yesterday was a good woman’s suitcase, and I packed it full with my new clothes, shoes, purses, etc. After I did an express checkout over the phone, I walked out of the room where I’d become a woman, tugging my suitcase behind me with my backpack on top of it, all of my men’s clothing already tossed into a hotel dumpster. It was time to get on with my new life.
To be continued….
The long awaited, much anticipated sequel to Misstaken Identity: can a message in a bottle solve a murder?
He woke up early after a sound night’s sleep, his first in memory. There was something about the waves, the sound they made as they rolled onto the broad sandy beach, that always soothed him. That, and the fact that it was thirty degrees cooler than the weather he’d left behind in Salem. Sleeping without air conditioning, with the windows open to the fresh sea air, was better than any sleeping pill.
It had been a frustrating month for Detective Hal Wallace of the Oregon State Police. The fruitless search for a hiker lost on Mount Hood during a freak spring snowstorm, and the unsolved murder of a young intern for a Portland television station, had both bedeviled him, and he was beginning to wonder if it was time for him to look for another line of work. A long weekend on the Oregon coast had been prescribed by his sympathetic supervisor, who offered him the keys to her beach house in Lincoln City, and he’d jumped at the chance to escape the impending heatwave for a few days.
He knew that the crowds would be arriving early as day trippers flocked to the coast to cool off, and a check of the tide table confirmed that low tide was in a few minutes. So he threw on shorts and a hooded sweatshirt and walked across the street to a long, winding staircase that deposited him on the deserted beach. He’d traveled a lot in his youth, and he’d never seen a more stunning coastline than the stretch of Oregon between Cannon Beach and Bandon, where monumental rock formations sprang out of the sea, and massive trees washed up occasionally after a Pacific storm.
Kicking off his flip flops, he started to stroll along the broad beach. He wasn’t looking for anything in particular, perhaps a nice agate or a conch shell to add to his collection, when he spied the bottle, floating a few feet offshore. It looked to be a large wine bottle, with a red top and something white inside. Curious, he stepped into the waves and picked it up. The red top was a glob of old-fashioned sealing wax covering the cork, and inside there appeared to be several sheets of paper, coiled and held together by a rubber band.
The detective in him was naturally intrigued. He stuffed it into the pouch in the front of his sweatshirt. Perhaps he’d open it after he finished his walk along the beach.
* * *
I hated my driver’s license photo!
When I threw my fake license together, I’d settled for an old picture of me as a guy, but with long enough hair to make my sex questionable. Now that I was living full-time as a woman, my vanity was such that I absolutely had to have a better picture on it. Fortunately, I’d saved the template I created in Chicago as a file on my new email server, so after I settled into my condo on Sanibel Island, I posed for a passport photo at drugstore in Fort Meyers, then on to a FEDEX store to create a new license with my smiling face.
Before I left, I surfed the web once again for any news of the missing hiker on Mount Hood (me) or the murdered intern at KOIN who had been my friend. There was nothing to be found, and I figured that the old me was already forgotten, except by the drug lords who knew that I’d stolen three million dollars from their bank account, and probably assumed that I’d faked my death on the mountain.
So far I’d kept one step ahead of them. After I left Tampa, I’d pulled onto the freeway and headed south, exiting at Fort Meyers where I had a bite at a fast food restaurant (a woman dining alone was no big deal at such places) before I continued over the causeway to Sanibel Island. I’d read about Sanibel years before, and it had always fascinated me: an island on the Gulf Coast, it ran east to west, which positioned it to trap a never-ending supply of fantastic seashells on its miles of sandy beaches. It was relatively isolated, and most of the occupants were very rich, living there during the winter months and closing up their homes and condos when the summer heat set in. There was a wide range of hotel accommodations, as well as furnished residences available for short and long term rental, and I was interested in a condo on Middle Gulf Drive that had a view of the Gulf and was a short walk from the beach, if the listing I’d spotted on the Internet was to be believed.
So I pulled into a realtor’s office and presented myself to the pretty young receptionist. “What a lovely dress,” she exclaimed, and I smiled back at her. I was beginning to feel the sisterhood that women instinctively radiated towards one another.
“Thanks, I got it in Tampa yesterday.” Then I whispered, “On sale at the outlets.” She laughed. “I’m interested in this listing.” I handed her the address on a scrap of paper. “Is it still on the market?”
“Let’s find out.” She excused herself, and returned in a few minutes with a stunning realtor, who was probably in her late thirties, but who possessed a perfect figure, and only a few tell-tale lines on her lovely face. But I felt nothing in my panties. Had my night with Ryan tapped me out? Or was I already past the point of no return?
After we introduced ourselves, she invited me to a small conference room. I smoothed my dress as I sat down, crossing my legs self-consciously – this was my first one-on-one encounter lasting more than a few seconds with another woman, and I wondered if she’d penetrate my disguise?
She didn’t. “You’re in luck,” she said. “The owners of that unit just packed up and returned to their home in Pennsylvania. It’s available next week – right now it’s occupied by an elderly couple who’ve been spending this week there for the last several years, I think it’s their anniversary – but after that it’s wide open till June. The minimum rental is one week. It’s a popular unit, so if you’re interested I suggest you move fast.”
“So if I wanted it starting next week and wanted to stay there for a month, what kind of discount would they give me for a 30 day lease?” The weekly rent was a fortune, but the unit was perfect, at the end of an isolated lane so nobody could approach without being seen – I’d surreptitiously checked it out after I drove onto the island. If I could stay there till summer, by then I ought to be able to find something more permanent, assuming I decided to stay in Sanibel.
She got the owners on their cellphone, and after a quick conversation she reported that they were willing to knock a few hundred dollars off the rent. Done!
* * *
Island life definitely agreed with me. After a few weeks, I’d settled into a daily routine: up at dawn for a jog in a sports bra, tank top and running skirt on one of the bike paths that circled the island, and then floor exercises to tighten my abs and butt, followed by a light breakfast on my screened lanai (I’d become hooked on donuts with key lime filling) and my daily feminizing routines (keeping my body shaved and moisturized, my toenails a bright pink and a myriad of other female ablutions) before I put on a woman’s swimsuit to lay out with a fashion magazine (I had so much to learn!) by the small pool next to my condo until it got too hot, then I’d take a dip in the pool, lay out some more and finally, if it was close to low tide, I’d walk to the beach and lose myself in the search for seashells, which were endlessly abundant and gorgeous beyond belief. After I returned to my condo with my treasures, and fixed myself a light lunch on my lanai, I’d take a little siesta during the hottest part of the day, followed by a relaxing bubble bath after I washed and conditioned my hair, then after I dried my hair, I’d put on shorts and a girly tee shirt for my daily bike ride (on a beach cruiser provided by the unit’s owners) to Jerry’s market.
I’d never been much of a cook, but I had a lot of time on my hands, and it seemed so right for me to put on an apron and whip up something special in the kitchen. I did a lot of daydreaming, and I wondered if I’d ever have the chance to make dinner for a boyfriend like Randy? We’d actually exchanged a few emails, and he seemed to enjoy flirting with me, but I was careful not to tell him where I lived, and it was unlikely that I’d ever spend the night with him in Tampa, if his apartment was as bad as he said.
So I kept looking for things that I could do as a single woman. I became a mall rat, driving over the causeway to air conditioned malls where I’d spend hours trying on cute outfits until my closet was jammed with skirts, tops and dresses, not to mention shoes! I bought a set of second-hand women’s golf clubs on Craigslist, a skort, polo shirt and a pair of Lady Footjoys at a golf discount store, and played a few times in the early evening after the heat died down, which was a blast off the ladies tees, but eventually the bugs got to me. One night, out of desperation and loneliness, I put on my shortest skirt and tried my luck at a tribal casino on the mainland, and I even won a few dollars at the slots, but I was afraid to respond to the few guys who tried to hit on me, for fear that they’d kick my ass once they discovered that I was really a guy.
So loneliness aside, I was happy with my new life, and I truly loved being a woman. Life seemed to pass by at a slower pace, and all the little things that a woman has to do to make it through the day filled me with a strange contentment. With every passing day, it became clearer to me that this was the person I was meant to be, and I knew that I could never go back to being a man, even if I didn’t have a price on my head.
During one of my shopping trips, I bought myself a laptop computer, and in addition to trolling the real estate sites for a permanent residence on Sanibel, I spent a lot of time doing research about my old life in Oregon. It seems that I was presumed dead after the search for me had finally been called off (at a cost to the taxpayers of almost a million dollars) and there continued to be no leads into the killing of the KOIN intern. I’ve never had much of a conscience, but maybe there was a way that I could help the police pin Andy’s murder on the goons who wanted to kill me, and correct the ledger on faking my death in the process….
I also spent an hour each day writing these memoirs.
* * *
After he climbed up the stairs from the beach, Detective Wallace made himself coffee in the kitchen of his smartly furnished beach house, before he turned his attention to the bottle. There was definitely a note inside – more like a long letter on several sheets of paper – and after carefully peeling off the sealing wax and popping out the cork, he extracted the contents with the help of a long spoon handle from one of the kitchen drawers. He removed the rubber band, unrolled the missive – it was even longer than he thought – sat down in a comfortable chair, and started to read.
His hands were shaking by the time he got to the second page. Whoever wrote this had just solved the two cases he was working on! It was inadmissible as evidence, but if he could find the mysterious author, and follow up on these leads, he’d be able to put a vicious murderer behind bars, and some badass drug dealers out of business. And he had to admit, there was something fascinating about the person who was telling him all this: a man who had faked his death and decided to turn himself into a woman. It was almost too fantastic to believe. Had he actually gone through with it? Detective Wallace felt himself becoming strangely aroused as he continued to read….
* * *
A few days before my lease expired, I packed up most of my new wardrobe into several large boxes and left them in a storage locker I’d rented in Fort Meyers. Under the layers of female clothing, almost two million dollars in cash was stashed at the bottom of the boxes. I took my time packing my suitcase – it took a lot of thought to make sure I included all the things a woman needed – and before I left I asked my realtor to keep her eye out for a small condo similar to the one I’d been renting.
Then it was time to head north, to Tampa Bay, where a certain someone was waiting for me. A pretty girl in a hot convertible attracts a lot of attention, and I indulged the guys who honked at me by waving gaily back. I wondered if Randy would notice the subtle changes that I’d undergone: my body was a bit thinner and a lot tighter after 200 crunches a day, and bikini lines accented my deep Florida tan. I hadn’t yet taken the plunge with female hormones, but I knew that it was only a matter of time….
I was wearing a nautical dress with matching flats, and I figured if Randy didn’t have an erection when he saw me, he was right about turning gay. I needn’t have worried. He was waiting for me in the restaurant of the hotel where we’d met, looking just as gorgeous as I remembered. Once again, we bantered over the menu like were total strangers, although with enough double-entendres and whispered word play to make our intentions known.
“Has the lady decided on something to drink?”
“Before or after dinner?”
“Naughty girl! Before.”
“A glass of your most expensive Chardonnay.”
“We’re moving up in the world.”
“I haven’t been out in almost a month.”
“Now I know what I’m drinking after dinner.”
I know, it all sounds so silly, but we were giddy at the sight of each other, and I could hardly eat, I was so desperate to have him back in my bed again. For old times’ sake, I’d reserved the same room where he took my virginity, and when he tapped on the door later that evening, I was wearing the same sexy nightgown. I watched with alarm as he tore off his clothes and practically leaped into bed. That night, I think he taught me every position in the Kama Sutra, plus a few others that were more suited to our particular anatomies….
It wasn’t love, it was pure, sweet lust, and after each round, as our bodies slowly built up steam for more, we teased each other back and forth, almost like best friends. In the raw, we both might have been guys, but in my nightgown, with my long hair, tanlines and pink toenails, I looked and felt totally feminine, which seemed to bring out the animal in Randy. I can’t explain the attraction, nor do I understand why he was so attracted to me, but that doesn’t really matter. For the second magical night, we had sex until we wore ourselves out, and when he finally left me shortly before dawn, I felt totally fulfilled.
* * *
The next morning, I headed north, and then northwest, towards Oregon. I tried to steer clear of southern states which had issues with transgendered persons, although after living full time as a woman for over a month, I was entirely confident in my appearance and mannerisms, and never encountered a problem.
The drive took four days, so I had a lot of time to think about what I was going to do. Settling the score with the authorities who spent $867,000 searching for me on Mount Hood (I confirmed the amount searching the Internet) would be the easy part. Pinning Andy’s murder on the bosses at my old company would be much harder. After I disappeared, they must have hired a new IT professional, who’d installed an impregnable firewall which prevented me from accessing their server and downloading evidence of their crimes. But I still had my old email address, and the day I crossed the Oregon border, I sent this message to the CEO from the business center of my hotel in Medford:
I know who killed Andy Moffatt. For a price, I can keep it to myself. Meet me at the top of Cape Kiwanda on Saturday morning at ten with one million dollars in small bills. Come alone.
Of course, once he saw that the email came from me, he’d instantly realize that I’m still alive, and his erroneous suspicion that I was the one who ratted him out to KOIN will be confirmed. I don’t expect him to come with a million dollars, and I don’t expect him to come alone. In fact, I don’t expect him to come at all – no doubt he’ll send the goon who killed Andy. Rather, my plan is to be waiting at Cape Kiwanda as a girl, and to video whoever shows up while he waits for the old me. The video, combined with the fact that he responded to the incriminating email I sent to my old boss, ought to be enough to put them both away.
After I left Medford this morning, I drove up Interstate 5 until I got to the Woodburn outlets. It will be overcast and cool tomorrow on the Oregon coast, and I need something that will keep me warm and won’t stand out. Something casual. Eventually I put together a woodsy outfit consisting of a gray tunic dress, a short black jacket, leggings and a pair of black skimmer flats.
I had one more stop before I drove over the coast range: in Salem, I left a banker’s box containing $867,000 with a security guard at the headquarters of the Oregon State Police, with an anonymous note wishing that the contribution be used to help offset the cost of searching for missing hikers in the Cascades. Then I drove to Lincoln City, a beach town a few miles south of Cape Kiwanda, and checked into a nondescript motel.
Now it’s time for me to put these memoirs into a wine bottle, seal it up tight, and commit it to the waves. I’m no expert, but I’m hoping that if I throw it beyond the breakers at low tide tonight, it’ll catch a current and wind up in Japan some day. By then, maybe I’ll have lived out my life as a woman? Whatever happens to me tomorrow, my conscience will be clear.
* * *
Detective Wallace sprang out of his chair. The little fool! He – or she – had tossed that bottle into the Pacific last night, only twelve hours ago. He knew this, because he was still in the office when the anonymous contribution of over eight hundred thousand dollars was dropped off yesterday afternoon. It had created quite a stir, and everyone was talking about the beautiful woman who delivered it.
What time was it? Shit, it was after 9:30! Less than half an hour until her rendezvous with the vicious killer who’d been eluding him for over a month! What if she was walking into a trap? He grabbed his gun and raced for his unmarked police car. Fortunately, most of the traffic was headed in the other direction, beachgoers on their way to Lincoln City, but he had to turn on his flashers and run a couple of lights as he raced up the Coast Highway.
As he screeched into the parking lot at the Pelican Pub and Brewery, he spotted an Audi S5 convertible with Florida plates. Damn, she was really here! There was a small crowd on the beach, and a few adventurous climbers making their way up the dunes to the top of the cape. Statistically speaking, this was one of the most dangerous places in Oregon, as several times a year hikers would plunge to their deaths into the ocean after ignoring warning signs and fences on their way up. He thought he could make out a man and a woman near the top…she was wearing a gray dress with a black jacket, and the man appeared to be holding something in his hand. A gun.
Detective Wallace had been on the track team at the University of Oregon, not a star by any means, but he’d kept in shape, and he put his head down and raced up the steep slope with a sprinter’s speed. He’d closed to within fifty yards when the assassin saw him, and Wallace dove to the ground as the assassin’s gun swiveled in his direction. Meanwhile the girl seemed to lunge at the assassin, momentarily throwing off his aim, until he pushed her back hard towards the sandstone cliff. It started to give way beneath her feet, and Wallace heard her scream as he rolled into a crouch and pulled out his gun. A bullet whistled past his ear, and when he returned fire, his aim was deadly. The assassin’s head exploded, and his body fell lifelessly over the cliff into the churning Pacific.
Wallace got up and ran towards where he had heard the woman scream. She was dangling over the cliff, her legs kicking futilely in the air as her hands scrabbled helplessly against the crumbling sandstone. He reached down and caught her just in time, grasping one of her hands. “Hang on, Kim. Stop kicking! Just let me pull.” She felt herself being drawn up against the cliff, as if she were ascending to Heaven. When she was up, she collapsed next to him on top of the cliff.
“You saved my life.”
“You saved mine,” he panted. He couldn’t take his eyes off her. She was incredibly beautiful.
“How did you know my name?”
“I read the message in your bottle.”
“But how…”
“It would appear that you’re not an expert on the tides.” His breathing was slowly returning to normal.
Her hands went up to her face. “Then you know….”
“I know. I also know that you’re a hero. Or a heroine, I guess.”
“Who are you?”
He pulled out his badge. “I’m the detective who’s been searching for you for the past month, and trying to figure out who killed Andrew Moffatt.”
“Am I going to jail?”
He laughed. “No, you’re not going to jail, Kim. You’ve already made restitution for the trouble you caused on Mount Hood. And thanks to you, we’ve solved the Moffatt case” – he glanced over the cliff towards the body floating by the rocks – “and after they fell for your clever email, we’re going to be able to put your old friends away for good.”
“But what about the money I stole?”
“I don’t think that will ever be reported, do you? As far as I’m concerned, that was just an intracompany transfer. The state police aren’t in the business of solving crimes that never happened.”
She got unsteadily to her feet. “What happens now?”
“I’ve got some work to do.” He pulled out his cellphone. “And I’m starving. After I phone this in, why don’t we walk down to the Pelican for a bowl of crab chowder? It’s going to be a busy day.”