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….