The Craigslist Killer Chronicles

FLASHBACK

I think I'm in the clear for now. The police have come and gone, and the hotel staff has cleared the hallway outside my room. If I could, I'd try to get some sleep, but after what I've just been through, that would be difficult. So I'll try to write down exactly what happened this week, while it's fresh in my mind, in case my lawyer needs it in the morning.

One thing's for sure: I will never, ever dress up as a woman again.

Who am I trying to kid? I'm trying to describe the most terrifying experience of my life, and I haven't even bothered to take off my torn dress and shredded stockings. So let me rephrase that: I will never, ever dress up as a woman again to meet a stranger from Craigslist.

* * *

CROSSDRESSING COUGAR WILL PURR IF YOU PET HER - T4M

If you're a mature, sophisticated guy who digs a classy woman with a secret in her panties (or has always wondered what it would be like to bed one) this pretty, passable crossdresser will be on the prowl in Chicago next week...I am totally turned on by good-looking guys, and I love to please my man. If you're interested and STD-free, send me a picture of your handsome face and let's echat! Missy

That was the personal I posted under the "casual encounters" section of the Chicago Craigslist site before I left for my business trip. In my real life, I was a corporate executive, and I had several days of meetings which I'd managed to cram into the beginning and end of my week, allowing me two full days to indulge my secret fantasy: unbeknownst to everyone who knows me, I am a closet crossdresser who loves to make it with men. I know how pathetic that must sound, but after many years - and thousands of dollars - of trial and error, I've learned how to transform myself into a very pretty woman, and nothing I've ever experienced can top the excitement of a being on a date as a girl with a handsome man.

So after scheduling my meetings and booking myself into a swank hotel on Michigan Avenue, I packed an extra suitcase for my alter ego. The weather forecast was perfect for fall fashions, with bright crisp days and chilly evenings, and I shaved myself down at my health club the day before my trip. That night, I put up my post on Craigslist, and waited for the deluge.

It didn't take long. As always, all responses were funneled by Craigslist to a coded account which relayed them to the email address which I maintained exclusively for Missy, my female persona. Within minutes, the hits started coming, and it was always amusing to separate the wheat from the chaff. Immediately rejected were any responses which did not attach the picture I demanded. Those which did include digital photos were further screened to eliminate the losers who sent me pictures of their genitals as opposed to their faces - a surprisingly large percentage of them did this, as if I hadn't seen it all before! Then I ruthlessly rejected prospective suitors whom I didn't find attractive, or were semi-literate, or who just struck me as wrong, odd, too young, etc. I should add that my post included a photo of me looking hot in a sexy dress, and the crop of guys who made the cut was encouraging. It's always amazed me how many so-called straight guys have a thing for girls like me, and the Chicago boys who tuned into Craigslist that evening looked very promising, and very eager.

I was immediately attracted to this one:

Hi there,

All i can say is WOW!! your ad is exactly what im

hoping for...

btw i luv your pic! I'm Ron. I'm white, 35

y/o, educated.. MBA in finance, professional with a great

career, refined mature and respectful, live alone and can

host or travel, 6' tall 180 lbs, 7" cut and thick, STD free

and can prove it. I absolutely adore T-girls and love to be

seduced...especially by a cougar with a special surprise. Most of my experience has been limited to mutual oral but im willing

to explore more if so desired. I am real and would love

to hear from you and hopefully get together. I can send more pix

if you are real and interested.

Sincerley,

Ron

ps - got any pics of you with anything skimpier on? : )

Attached to Ron's post was a digital photo of a really cute guy, with a full head of dark hair and sort of Latin features, in a polo shirt standing next to a sailboat. The kind of guys I hang out with as a guy, clean-cut and preppy. After culling through the rest of the responses, I put Ron at the top of the list, and sent this reply:

Hi Ron,

You're cute! I'll be available Wednesdsay and Thursday next week... tell me about yourself, Mister! My email address is

missy4fun@xxxxx.com

.

Missy

ps - here's that picture, skimpy enough for ya?

Attached was a digital photo of me curled up on a hotel bed in a babydoll nightie, matching thong and thigh high stockings, which made me look incredibly hot. I'd learned from past experience not to say too much about myself at first, since a ridiculously high percentage of guys on Craigslist were merely trolling for pictures to pleasure themselves to, and I wanted to establish email contact before going any farther. I was sifting through the rest of my responses when my computer pinged that I had an email. It was from Ron:

Hi Missy,

So you are real! God, you look hot in that nightie!

I'm a straight guy most of the time, divorced with one kid who lives with the ex, first met a tgirl when I was on vacay in Hawaii and never got over it, how long have you been dressing up? I'm free on Wednesday this week, where are you staying?

Ron

Now that I had Ron's email address, I let my hair down a bit:

Hi Ron,

Of course I'm real, silly!

Thanks for taking a chance and responding to me on

Craigslist...needless to say, there have been some wild

responses! I've been fascinated by crossdressing for as

long as I can remember, and once I realized that I am

actually passable as a woman, it's become a big part of

my life.

A bit more about me: I live in SoCal and I'm in

Chicago on business next week, staying at a hotel on the mag mile...so what's your idea of a perfect first date?

Missy

I'd barely had time to check for any new Craigslist responses when my computer pinged again. Another email from Ron! He was hooked, and it was time to reel him in:

Hi Missy,

A California tgirl! Do you have bikini tan lines? ; )

Let's have dinner Wednesday near your hotel, okay?

Ron

A date! As a woman! With a cute guy! Just the thought of it made me tingle downstairs. I decided to tune out the rest of the finalists and zero in on Ron, before he got away:

Hi Ron,

It's a date! Where would you like to take me? Oh, and what will you

be wearing? A girl needs to know these things...I really like the vibe I'm getting from you Ron, here's my cellphone number in case you'd like to chat after I get to Chicago tomorrow: 213xxxxxxx. G'nite,

Missy

It was getting late, and I had an early plane to catch!

* * *

After I checked into my hotel, took care of a few business emails and went through my phone messages, I had half an hour before a dinner meeting with one of our customers. Enough time to unpack and hang up the skirts and dresses I'd selected for the week, stash my shoes and purses in the closet, and tuck my lingerie and stockings into a dresser drawer. The bathroom vanity had a drawer for all of my makeup, and there was just enough time to wash and rinse out my wig and hang it out to dry on the showerhead.

By the time I got back from dinner, I was exhausted, and I had a full day of meetings the next day beginning with a breakfast at eight o'clock. But that didn't stop me from checking the throwaway cellphone that I used exclusively as a woman for messages. Sure enough, there was a voicemail from Ron:

"Hey Cissy, I hope I got the right number, it's Ron. Call me if you wanna talk tonight! My number's 312xxxxxxx. Hope we're still on this week! OK, bye."

I took off my business suit, brushed my teeth and put on a nightgown and panties before I snugged under the covers of the king-sized bed and called him back. He answered on the first ring.

"There you are! Are you in Chicago?" He had a soft, deep voice.

"Yep. How are you?"

"Cool, now that I know you're here. I was starting to worry that maybe you weren't coming."

"Oh ye of little faith!" My female voice wasn't the greatest, but I was getting better at it, especially when I kept it short and sweet.

"So are you a girl right now?"

"Um hmm."

"That is so hot! What are you wearing?"

"Just a nightie and panties."

"Oh God. The one you wore in that picture?"

"Um hmm."

"Oh God. Do you have the nylons on too?"

"Nope. That was just for fun."

"Aren't we having fun right now?"

I felt myself starting to stiffen. "Let me check my panties." A beat. "Oh yes."

"Oh God." I could tell that he was way ahead of me. "Oh God."

"Don't you wanna save yourself for our date?"

"Missy, I can go all night long. Oh God! Ohhhhh..."

"Hello?"

"Oh God, that was so good."

"Sounds like my work is done here," I giggled.

"You are so hot, baby!"

"And we haven't even met."

"Don't worry, we will. Where can I take you for dinner?"

"Hmmmm...there's a nice restaurant at my hotel."

"Where are you staying?"

"The Interconti."

"Perfect, what time?"

"You're the one wearing the pants, you get to decide!"

"Ha! How about seven?"

"Sounds like heaven, a date at seven!"

"Okay Missy, I'll see you then. What are you gonna wear for me?"

"I dunno, either a skirt or a dress. Maybe I'll buy something on Michigan Avenue. How about you?"

"Me? Oh, I'll be in a suit and tie, okay?"

"Sounds very dashing!"

"I can't wait! See ya Wednesday."

"Me too. G'night!"

"Goodnight."

Well, it sounds like I have a red-blooded American boy on my hands, I thought to myself as I turned out the light. Craigslist dates were always iffy: how many of the guys lied about themselves? Sent bogus photos? That's why I always tried to draw them out via emails, and get them to call me so I could hear their voices. But Ron sounded like the real deal. Maybe, just maybe, it'll be more than just a one night stand? I mused as I drifted off to sleep.

* * *

Tuesday was a total bitch. That was the downside of scheduling all of my meetings at the beginning and end of a business trip. Several times during that grinding day, I had to stop my mind from wandering to the delights that lay ahead for me: two glorious days on The Magnificent Mile as a woman, topped off by a dinner date with a cool guy who wanted to get into my panties!

By five o'clock Tuesday evening, I was dragging ass when I got some unexpected good news: my dinner that evening with the CEO and CFO of an important customer had been cancelled so they could race to New York to handle some crisis. Heaven! I was free until Friday morning - sixty uninterrupted hours as Missy!

As soon as I got back to my room, my metamorphosis began. First, a hot, lazy bubblebath in the oversize tub, where I patiently shaved away the stubble which had begun to grow back on my legs. After smoothing myself all over with the hotel's luxury moisturizing crème, I went to work on my face, marveling as always in the gradual transformation from male to female. It wasn't complete until I put on my wig, a collar-length bob with wispy bangs, and I took my time styling it just so. Standing in front of the mirror in a hotel bathrobe, polishing my nails, I was all girl.

A spritz of cologne, then it was back to the bedroom, where I selected a bra, panties and nylons to wear under my dress. That was one of the advantages of staying at a big-city hotel: a girl would fit right in wearing something nice, and I knew that I would blend with the other professional women having dinner downstairs. I almost never got to wear nylons in LA, but for a chilly autumn in Chicago, they would be part of my uniform this week.

What to wear tonight? I finally selected my gray wool jumper, which was unlined, so I put on a full slip before I tugged on my dress and went to work on the buttons and bow. When I was finished, I added some bling and a colorful scarf, stepped into my heels, and sat down on the edge of the bed to organize my purse. Sometimes, the collision of feminine scents and sensations was enough to produce a surprise orgasm before I even finished getting myself dressed, but my body behaved itself tonight, and I was hoping that I'd be able to hold off until my date with Ron tomorrow.

After a last, long inspection of myself in the full length mirror on the back of the closet door, I headed down the hall to the elevator, a pretty woman all alone on a business trip, making her way in a man's world. She smiled at the other passengers on the way down to the lobby, stopped at the concierge station to help herself to a Chicago Tribune, and presented herself to the maître d with a single finger pointed in the air. "One, please."

She was shown to a small table in the crowded restaurant, and a quick glance around the room confirmed that she was one of four single women in business attire, all dining alone tonight. Several of them were playing with their smartphones, and after I ordered a glass of Chardonnay and studied the menu, I took my iPhone out of my purse and scrolled down to Missy's email account to find a message from Ron:

Hi Missy,

Last night was a blast! Do you text? I'll try your cell. Till tomorrow!

Ron

Sure enough, when I retrieved Missy's cellphone from my purse, there was a text from Ron:

Hi Missy, are you a he or a she 2nite?

I wondered whether he was still near his phone. After I ordered a salad and some pasta, I gave him a try:

Right back at ya, I'm all girl now

Wow, in your room?

Nope, the hotel restaurant

OMG, that is so cool, what are you wearing?

Just a dress

Nothing underneath LOL

That's rude! Of course not

What's under your dress?

Bra, panties, slip and nylons

OMG, getting hard again

Down boy!

You are so fucking hot

Don't wear yourself out, mister

The waiter returned with my salad. I ordered another glass of wine and checked my phone. Nothing from Ron. I sipped my wine for a while, reveling in the moment. Here I was, dressed as a woman, getting tipsy on my expense account, getting a guy off. I glanced around the room, catching a few male eyes. If they only knew! I decided to try Ron again:

ru still alive?

Barely that was amazing

u came again?

Totally

ur incorrigible

u made me

I just hope you have something left in the tank tomorrow night

Don't worry

My dinner's here, gotta go

OK, bye

There were no further interruptions that evening. After I finished my dinner, I returned to my room, peeled off my dress and frillies, creamed off my makeup, and put on my nightie. Another crazy day in my crazy life, with two more to go! I wondered what Ron was thinking right now? Would I live up to his fantasies? Would he live up to mine?

* * *

I slept in the next morning, luxuriating under the covers until almost nine. Get up, girl, you've got a busy day ahead! I chided myself. After a quick check of the local news confirmed that today's weather would be crisp and fine, I drew another bubble bath and gave myself a close shave from head to toe.

My makeup was a bit more casual this morning, with pink lip gloss and beige eye shadow instead of my evening red and black. Then it was back to the closet to decide what to wear for a day on one of the great shopping streets in the world. I settled on my black pencil skirt, my pink blouse with a bow, and my gray blazer. My skirt was a little tight, so I started with my black body briefer and sheer black pantyhose. Standing in front of the mirror, tying my bow in my stocking feet, I felt every inch a pretty girl, and after I stepped into my cute but comfy flats, I was off to face the world again.

First, a light breakfast at the Corner Bakery. Idling over a muffin and coffee with yesterday's Tribune, I felt totally at home in my temporary skin. An article in the Metro section caught my eye:

POLICE SEARCH FOR CLUES IN HOTEL SLAYING

Chicago - A transgendered tourist was savagely beaten to death by an unknown assailant in "her" hotel room last night. After guests in a nearby room at the Sheraton complained about a loud altercation, hotel security entered a room registered to a male guest to find his body, partially clad in women's clothing, with multiple stabwounds in his chest, neck and arms. The guest's indentity has not been released pending notification of relatives. A hotel employee informed the Tribune that the safe in the closet had been opened. Chicago police declined to release details about their investigation into the search for the killer.

A chill went down my spine as I wondered how that could happen. Where was the tourist from? Could it have been someone like me? I tried to imagine the shock to my friends and family after receiving a call from the Chicago police, informing them that I'd been found murdered in women's clothing. Well, there was no way I'd ever let a stranger into my room! All the more reason to carefully screen the men I played with, like I had with Ron...still, it was a good reminder to be careful. I was so vulnerable dressed this way, and I shuddered at the thought of being preyed upon by some sicko...

Back outside, I indulged myself with a cigarette as I window-shopped down Michigan Avenue, stealing glances at the smartly dressed women who passed me by, and at my reflection in the storefront windows. One thing I loved about Chicago was the self-confidence of its women, and I felt right at home as I joined them on the sidewalk. My skirt and blazer marked me as a lady lawyer or executive, my dainty shoes were easy to walk in, my legs felt warm and cozy in my stockings, and all was right with the world. The mysterious murder a few blocks from my hotel was already forgotten.

Hours later, laden down with shopping bags, I returned to my room, relieved to find that the housekeepers had already been there. I fished the scissors out of my makeup case and carefully cut the tags off my new dress, a black and tan color blocked sheath that gave me an hourglass figure when I'd tried it on at Carson's.

I'd paid cash for my dress, and I opened the safe in the closet to put the rest of my wad in my man's wallet. Since dinner tonight was in the hotel restaurant, the only thing I'd be carrying in the little clutch purse that I'd bought at a boutique in Water Tower Place was a brush, some lippy, and my room key. And my chickphone, I reminded myself, in case Ron was lost or late!

Another luxurious bubble bath, some extra time to embellish my makeup with nighttime touches, and I was ready to get dressed for my big date. Tonight, if all went well, I'd be inviting Ron up to my room after dinner, so my lingerie was strategically selected: a black Wonderbra that I could wear without breast forms and still have a hint of cleavage, silky black panties, black thigh high stockings, and the lacy black slip that I'd also bought today to wear under my new dress. I hoped that my dress would still look good without the body briefer I'd worn when I tried it on, and I wasn't disappointed: after I stepped into it and zipped myself up in the back, I smiled when I studied my reflection in the mirror.

Looking back at me was a gorgeous girl with a cute figure and terrific legs, and I started to feel that tingle in my panties...not now, I scolded myself, you have a date tonight! Act like a lady! A glance at my delicate women's wristwatch told me it was almost time to go. I retrieved my black stilettos from the closet and eased them on, which made my legs look even better, although I could only take a few mincing steps before the pain started. That's okay girl, you're only going downstairs to the hotel restaurant, I reminded myself. With that, I put my key, lipstick and brush into my little clutch. Oops! I almost forgot my cellphone! I quickly stuffed it into my purse, and I was off.