The Craigslist Killer
© 2014 by Nom de Plume
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’m 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 [email protected].
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.
The same maître d greeted me, and I held up two fingers this time. “Are you expecting someone?” he asked.
“Yes,” I smiled.
“Would you like to be seated now?”
“Yes, thanks.” He escorted me to a small table in the middle of the room, and I glanced over at the romantic booths along the wall. “Would you prefer a booth?” he asked without missing a beat. When I nodded, he led me over to one, and I sat down where I’d be able to see Ron when he came in.
At first, I thought nothing of the fact that Ron was running late. After all, he might be having trouble finding a place to park, or he might have gotten delayed at work. I declined a waiter’s offer to get me something to drink, and sat contentedly in my little booth as the restaurant slowly filled up with businessmen and women, including the occasional loner like myself. I was terribly overdressed to be a woman dining alone, and I did catch a few glances from some of the other diners as they must have wondered about me.
Seven ten, seven fifteen…where was he? I took my cellphone out of my purse, but there were no calls or texts from Ron. The reality finally began to set in as I sat there stewing: another Craigslist wannabe! What a fool I’d been! The too-perfect response to my post, with an obviously bogus photo of a handsome man…the witty email exchanges…our phone chat, which had quickly devolved into phone sex…our texts last night, with me sitting here in a dress, and him getting off again…what a fool I’d been! Ron was probably a nerdy teenager living at home with his parents, or maybe he was a 300 pound goon who got off looking at pictures of tgirls…what a fool I’d been!
I was too embarrassed and depressed to face the prospect of dining alone as a woman again. Summoning as much dignity as I could possess, I got out of my booth, mumbled an apology to the sympathetic maître d, and tottered sadly back to my room. “Fuck!” I swore out loud in my real voice as I kicked off my heels and collapsed onto the bed. “Fuck this fucked up life!” I was starving after skipping lunch to keep my girlish figure, I was depressed and horny after being stood up, and I was furious at myself for falling for Ron’s idiotic games. Morosely, I fired up my notebook computer to see if there were any business emails I needed to deal with, then as an afterthought I switched to Missy’s address, where I found this response to my Craigslist personal:
Hi, just came across your post. It looks very interesting. Are you still in Chicago? Are you going to be here for more than this week? I have to fly out on Thursday and will be gone for a week. Would like to see if we can work out a meeting tonight?? I'll send info if it looks like we may be able to work something out.
Gregg
How long had Gregg’s response been sitting there? There was no picture attached, but he did say he’d send more info if I responded…I suppose it was because I was at my most vulnerable after just getting dumped, but I broke my cardinal rule and sent him this:
Hi Gregg,
Just got your response! Alas, I’m only here this week…send me a picture
and tell me about yourself,
Missy
That’s that, I said to myself. Probably another loser like Ron. I was debating about ordering something from room service when I got Gregg’s reply:
Hi Missy, would love to chat with you :) you look lovely in your dress and I must say you have lovely legs as well.
Do you have IM if so we can chat in real time and see if we can hook up
Oh I do not do drugs, smoke or drink to excess but social drink is always fine
Hope to hear from you soon
Gregg
Hmmm….an Eagle Scout, but still no picture! I glanced at my watch. It was only 8:00. I was trying to decide whether to nag him for a picture again when my instant messenger pinged:
Hey Missy
Hi Gregg
Are you still in town?
Yep
How about dinner tonight?
It’s kinda late
Have you already eaten?
Nope
Come on, my treat
You never sent me your picture
That’s a problem
What’s the problem?
I’m very well known and I won’t send it out over the Internet
Well known?
I’m on TV
Like a newsman?
Yes
Wow, that’s cool
I just got off work and I’m starving
Me too but I never date a guy without a picture first
Let’s meet for a drink and if you don’t like what you see, no harm no foul
I’m not leaving my hotel
I’ll meet you there
What if I find you irresistible?
We can always skip dinner
No way Mister! What kind of girl do you think I am?
Where are you right now?
The Intercontinental
I can be there in ten minutes
At the bar off the lobby?
Yes, on my way
I tried to respond, but he was already gone. Now I’d done it! Broken my cardinal rule! Although after getting scammed by Ron, an emailed picture didn’t seem like quite such a sure thing. What could go wrong? We’d meet at the bar, and if I didn’t like the looks of him, I could blow him off. It was a public place, totally safe for a girl. And the upside was, if he was on TV, he was probably gorgeous! And I was awfully hungry…and horny…before I could stop myself, I was back in my heels and headed out the door.
I emerged from the elevator and made a quick stop in the ladies room to freshen my lipstick and tweak my wig. Didn’t want to get there before him - a single woman alone in a hotel bar might attract unwanted scrutiny. When I’d fussed with myself long enough, I made my way slowly down the marble corridor, clickety clacking in my stilettos, trying to suppress a surge of excitement. Half an hour ago, I’d been a lonely wallflower, and now I was about to meet a mysterious stranger, looking hotter than hell in my new dress. A Chicago celebrity, no less! There he was, standing alone at a corner of the bar, handsome as hell in his blue blazer and repp tie. He looked up and cocked an eyebrow as I approached him.
“You must be Missy.”
“And you must be Gregg.”
He took my arm and led me to a bistro table by the window. I had to hop up into my tall chair, and I could tell that he was staring at my legs as I tugged my dress down towards my knees and crossed them. “Do I pass inspection?” I whispered.
“Oh yeah. One hundred percent. It’s hard to believe.”
“Well, I’ve had a lot of practice,” I said in my girlish voice, which was working for me tonight.
“How long have you been doing this?”
“You mean meeting handsome strangers in hotel bars?”
“No! I mean dressing up as a girl.”
It was always magic for me, talking to a guy on a date, confiding my innermost secrets to the only person in the room who had a clue that I wasn’t the pretty woman I appeared to be. “Since I was twelve,” I told him truthfully.
“Wow. Are you going to go all the way with this?”
He was easy to look at, and easy to talk to, and I found myself opening up to him. “I don’t think so. I mean, don’t think I haven’t thought about it, a lot, but I kind of dig my other life too. The one that pays the bills.”
A waiter appeared, and Gregg asked me what I’d like to drink. “A Cosmo, please,” I said demurely, and after Gregg ordered a Manhattan for himself, the courtship continued.
“What do your friends and family think?”
“They haven’t a clue.”
“You’re kidding, right?”
“Nope. I lead a double life. Should have been a secret agent.”
“Man, I’ll say. How do you manage that?”
“It’s not easy! I’m lucky that I travel a lot, and I’m only Missy when I’m on the road these days.”
“What do you do in your real life?”
“I work for a big company. Hey, I’m doing all the talking! Tell me about you.”
“In a minute. I find you fascinating. Do you only make it with guys?”
“No! I like women too.”
“Are you married?”
“I’m divorced,” I told him truthfully.
“Really! What did your wife think about this?”
“What do you think?”
“I don’t know. Some women might kind of like it.”
“Well, not her. It was really my fault. I never told her, and I’m sure she thought I was cheating on her, which I was, only not the way she thought.”
“I don’t get it.”
“It’s hard to explain,” I sighed. “I dressed up off and on all through high school and college, which I managed to keep a deep, dark secret from everyone. Then, when I got married, I went cold turkey for a while, but…” The waiter returned with our drinks, and I waited until we were alone again. “I just couldn’t stop,” I told him. “Cheers.”
He clinked his glass against mine. “Cheers. Thanks for telling me all that.”
I sipped my Cosmo, which went straight to my head, thanks to my empty stomach. “How about you? Have you ever made it with a girl like me?”
“Yes,” he confided.
“Have you ever tried it yourself? Dressing up, I mean?”
“No,” he answered nervously and a little too quickly.
“Are you gay?”
“Hardly! But for some reason, transgendered girls really turn me on. Like right now,” he added.
I felt the familiar tingling in my panties. “Well, what are we going to do about that?” I asked after I drained my Cosmo.
Gregg took a twenty out of his wallet, placed it on the table, and stood up. “We are going to your room, where I’m going to make love to you right now.”
I got unsteadily to my feet. “But you haven’t fed me yet.”
“We’ll have room service afterwards.”
I loved it when a man took charge. I loved being the passive one on a date. I loved being the girl. “Yes, sir,” I said, hooking my arm into his. When we got to the elevator, we had the cab to ourselves, and after I pushed the button for my floor, I put my arms around his neck and kissed him. He kissed me back, a sweet, tender kiss that lasted until we came to a stop and the doors opened.
He wrapped his arm around my shoulder as we walked to my room. I took my key out of my purse and opened the door. The light in the room was still on, and I was about to kick off my heels when the light went out. Then I felt Gregg’s hand over my mouth. Another hand grasped me savagely around my breasts, tearing my dress. “Don’t scream. Don’t say a word or I’ll break your neck,” he said in a menacing voice. “Tell me the combination to your safe.”
My mind raced. Gregg was the maniac who killed the tgirl at the Sheraton! And I’d let him into my room! Once he got into my safe, he might kill me…even if he just tied me up and left me, I’d be exposed as a transvestite when the police found me. I flailed my arms around wildly, and Gregg loosened his grip for a moment when I kicked him in the shin with a stiletto, then he twisted my head back and I couldn’t breathe. I was going to black out! My fingers brushed against the nightstand, and I felt the scissors which I’d used a few hours earlier to cut the tags off my dress. Without thinking, I picked them up, turned them around, and plunged the open points into Gregg’s side.
He grunted in surprise and loosened his grip again, just enough for me to spin free. In the dim light, I could see him reaching into his jacket, and the glint of a knife. Before he could react, I lunged forward and plunged the scissors into his neck, twisting them as I hurled him backwards onto the floor. I threw myself on top of him and was about to stab him again when I heard a terrible, gurgling sound, as he tried desperately to breathe through his severed windpipe. He thrashed around for a few seconds, his whole body shook for a moment, and then he was still.
I sat back panting for a long time. When I finally got up, I didn’t have to turn on the light to know what had happened. Gregg was dead. I’d killed him. When the police found out, I would become an overnight sensation. That kind of publicity would ruin my career, and make me a national laughingstock.
I got up unsteadily in my heels and turned on the light. Gregg’s body lay in a twisted heap, a wickedly sharp knife still in his hand, but to my surprise there was very little blood, and the room was otherwise undisturbed. I studied the wound below his hideously distorted face. Evidently I’d scored a clean shot directly through his trachea, and when I twisted the scissors I cut it clear across. He was as good as dead before he hit the floor.
I looked down at my torn dress and shredded stockings, which must have gotten ripped during the struggle. I couldn’t process the fact that I had just killed a man, dressed like this. A man who was armed with a knife, who had committed a murder two days ago, and who was about to kill me. I picked up the phone to call the police, but after another look around the room, I put it back down and started to think.
Nobody had seen me enter my room with Gregg. There were witnesses who had seen a pretty woman with Gregg in the bar, but my room was registered to a man. If I could just get Gregg’s body out of my room, and remove any traces of him, what could ever link him to me? Craigslist? Our IM’s? I’d cross that bridge when I came to it…Missy’s email address was untraceable to me, and if I got out of this, I’d get her a new one just to be sure.
I stood over Gregg’s lifeless body and tried to lift him. He weighed a ton! Finally I was able to drag him beside the bed so I wouldn’t have to look at him, then I went into the bathroom to rinse the blood off my scissors. The pretty girl looking back at me in the mirror was bedraggled, but she didn’t look like a murderess. It was almost as if nothing had happened to her. Coolly, she freshened her lipstick, brushed and fluffed her hairdo, and strode back to the murder scene.
A pang in my stomach gave me an idea. There was no way I could carry Gregg out of my room, but I might be able to wheel him out….after checking to make sure that his body was hidden beside the bed, I picked up the phone and asked for room service. After I ordered beef stroganoff and a bottle of red wine, I got down on my hands and knees and carefully studied the floor. There were a few drops of blood, but they were almost invisible against the burgundy carpet, and I would take care of them later.
Gregg’s knife was a bigger problem. It was undoubtedly the same knife he’d used at the Sheraton. I decided to put it back in his jacket pocket. Once the police found him, they might be able to use it to trace him to the Sheraton murder, which would draw their attention away from what happened here. I carefully wiped off my fingerprints first. I also wiped down the light switch that Gregg had touched.
There was a tap on the door. Room service! I went into the bathroom and in my male voice called out, “Come on in!” I heard the door open. “Please just leave it by the door, I’ll take care of your tip at reception.”
“Would you like me to set it up and open your wine, sir?”
“No thanks, just leave it please.” After I was sure the waiter was gone, I went to work: first, I removed the food, wine, cutlery and tablecloth from the room service cart. Next, I dragged Gregg’s body across the floor, lifted him up and leaned him against the cart. With a supreme effort, I was finally able to get him sprawled across the top.
Now for the risky part. It would all depend on luck. As an afterthought, I kicked off my stilettos to give me more speed. Then, with my room key in my hand, I cautiously opened the door and looked up and down the hall. Not a soul to be seen. With a silent prayer, I pulled the room service cart into the hall and began pushing it as fast as it would go, in the opposite direction from the elevator. It swerved wildly under Gregg’s weight, but I was able to keep it moving all the way to the end of the hall. Every second counted: if anyone were to see me trying to dispose of a body, I’d be in far worse trouble than if I’d just notified the police that I’d killed a man in self-defense.
There was a service closet at the end of the hall. I tried the door, but it was locked. So I would just have to dump him here. I rolled Gregg off the cart, and immediately started pushing it back towards my room. I was almost there when I heard the ding of an approaching elevator! Quickly, I unlocked my door, shoved the cart inside and pulled the door shut behind me.
It was only a matter of time before the body was discovered. Although this must sound callous, I was ravenously hungry, and I busied myself resetting the room service cart and opening the bottle of wine. I ate and drank slowly, savoring for the first time my survival from almost certain death. With any luck, when the body was discovered, there would be nothing to connect it to me, to this room. Which reminded me: I took my glass over to the blood spots on the carpet and poured red wine over them. It all blended into a typical room service mess.
Suddenly I heard a commotion in the hall. There was a scream, and somebody shouted. After a few minutes, there were more footsteps, and a muffled conversation. Then a longer delay before the police arrived, their walkie-talkies giving them away. All the while, I huddled behind my locked door, an unwilling witness to the drama taking place. I could hear doors opening and other guests asking questions, and the police and hotel staff instructing them to return to their rooms. Perfect!
Now it has gone quiet. In a few minutes, I’m going to take off this dress, stash all of my female paraphernalia in my suitcase, and collapse into bed. If the police come back, I’ll be the clueless man they expect. Maybe I’ll check into a different hotel tomorrow. Wait, my chickphone is ringing! I fished it out of my purse.
“Hello?”
“Missy, it’s Ron.” I was about to take his head off when he said, “I’m so sorry about tonight! My ex called me while I was on my way to tell me that our son was in the emergency room.”
“I don’t believe you.”
“Look, I don’t blame you! There was no way I could call you. By the time I got to the hospital, he was already in surgery.”
“Is he okay?”
“Yes, thank God. He broke his leg during football practice, and they had to put him under to set it, but he’s going to be fine.”
“Oh, I’m glad. I was really pissed, Ron.”
“Like I said, I don’t blame you. I only hope you’ll give me a chance to make it up to you. How about dinner tomorrow night?”
The Craigslist Killer Part 2
© 2014 by Nom de Plume
“Missy, are you still there? Please don’t hang up on me!”
“I’m here.”
“I really want to see you.”
“I don’t know, Ron…let me sleep on it, okay?”
“Sure, Missy, whatever you say. Can I call you tomorrow?”
“Okay. Bye Ron.” I hung up before he could say goodbye. For a moment, I was actually going to give in to him! It did sound so tempting to just take off my ruined dress, throw on my nightie, and tuck myself into bed, to awaken tomorrow as a woman with a man in her life. But the left side of my brain was screaming at me: get out of these stupid clothes now, before it’s too late!
Which is what I did. First, I poured myself the last of the wine. After I drank it down, I scrubbed off my makeup, removed the polish from my nails, and put my wig back into the plastic container it traveled in. Then, after taking off my dress, lingerie and stockings, I had a long, hot shower, wiping away my last remnants of femininity. A man once more, I wrapped myself in the bathrobe that Missy had used, and quickly went to work stuffing my extra suitcase with all of her shoes, clothing and makeup. I was just giving the room a final inspection when there was a sharp knock on my door.
I put Missy’s suitcase in the closet before I opened it an inch. “Who is it?”
“Chicago Police. May we come in?”
I opened the door to find two plainclothes detectives, both middle-aged men with tired faces. “What’s going on?” I asked them.
“We’re sorry to disturb you,” the taller one said, while his cohort circumnavigated my room with his sharp eyes.
I stood there in my bathrobe, my hair still wet, with a confused expression on my face. “I heard some cops out in the hall a little while ago. What’s going on?” I repeated.
“How long have you been in your room?” the tall one asked.
“I’ve been here all night. What the fuck is going on?” I asked again, sounding angry this time.
“Sorry sir, we’re following up on an investigation into a homicide.”
“A homicide? Here at the hotel?” I asked incredulously.
“Yes. Did you see, or hear, anything unusual this evening?”
“Other than the cops going up and down the hall about a half hour ago, nothing. Who got killed?”
The detective deflected my question. “So you didn’t let anyone in your room?”
“No, other than the room service waiter.” I motioned over to the trolley, which was covered with my half-eaten plate of stroganoff and an empty bottle of wine. The shorter one scribbled something in a notepad.
“And when was that, sir?”
“I don’t know, sometime before the cops showed up. You can probably find out by checking with room service,” I added helpfully. As close to an alibi as I could hope for.
“We will. And there was nothing else unusual tonight? No sounds of a struggle, or anything like that?”
“No. I wish you’d tell me what happened tonight.”
“Sir, we’re just starting our investigation. Sorry to have disturbed you.” The taller one handed me his card. “Please feel free to contact us if you think of anything. Goodnight.”
As soon as they were both out the door, I bolted and chained it shut, and collapsed onto the bed. Thank God I’d moved fast! A glance at the clock on the nightstand told me it was almost ten, and I turned on the local news to wait for any bulletins about a killing at the Intercontinental.
It was the lead story.
* * *
I was up early the next morning. It may seem surprising that I was able to sleep at all, but a bottle of wine and a unisom did the trick. It was a little after six when I presented myself to the front desk and told the girl behind the counter that I was leaving a day early.
“Was everything all right?” she asked.
“Other than the cops waking me up to grill me about a murder at your hotel, no problems.”
“I’m so sorry, sir! It’s been a crazy night….”
“I can imagine.” I slipped her a five dollar bill. “Would you see to it that this gets to the room service waiter who brought me my dinner last night, before all the fun started?”
“Surely. I hope you’ll be back soon,” she said after she handed me back my credit card. I thanked her and lugged my suitcases to the front door, where a doorman quickly summoned a taxi. “Airport, sir?” he asked.
“Yes,” I told him. Then, after the cabbie was underway, I leaned forward and told him, “I must be half asleep. Did I tell him I was going to the airport?”
“Yes, sir. O’Hare or Midway?”
“Neither. Sorry. The Palmer House, please.”
The cabbie shrugged and got into a left turn lane. In a few minutes, I was checking into my new hotel. I’d requested an early check-in, and the Palmer House was ready for me. At a few minutes past seven, I was hanging up my skirts and dresses again, and my chickphone was back on.
I turned on the TV, and found the local news. They lead with the same story as last night:
“Chicago police are tightlipped about two murders which took place at two of the city’s top hotels this week. On Monday night, a man dressed as a woman was found stabbed to death in his room at the Sheraton, and last night, a man was discovered dead in a hallway at the Intercontinental. According to sources at the Sheraton, robbery may have been the motive for the first slaying, but few details have been released about the victim at the Intercontinental. Two hotel guests, a man and a woman from Indiana, reported discovering a body on their way back to their room after dinner last night. The victim was reported to be a well-dressed man about thirty years old with a cut throat.”
I wondered how much more the police had learned, and weren’t saying. They must know Gregg’s identity, assuming he was carrying a wallet with him. How long until they showed his picture to hotel employees, and learned that he was at the lobby bar last night with an attractive brunette? I tried to remember if there were security cameras in the hotel lobby, or the elevator, where I kissed him…the memory of that made me shudder.
Was I really going to let Missy out of the closet again? I was having second thoughts when my chickphone rang.
“Hi Ron,” I said, switching instinctively to my female voice.
“Good morning. I hope it’s not too early.”
“I’ve been up for hours.”
“I haven’t gotten much sleep. Between worrying about my kid, and worrying about us….”
“I have to tell you honestly Ron, that I’d written you off after you stood me up last night.”
“I’m sure you did.”
“And I’m just not sure I feel the same way now, about seeing you I mean.”
“Look, why don’t we meet for coffee this morning. At least give me the opportunity to apologize in person.”
“I’m not sure….” What the heck, I had nothing to do today, and in spite of all I’d been through, my inner woman was yearning to break free again. “I guess.”
“You will? That’s great. I’m tied up till around ten, how about after that?”
“OK. I’ll text you where to meet me.”
“Aren’t you at the Intercontinental?”
“I checked out. It’s a long story.”
“Okay Missy. I’ll wait for your text.”
“Bye.”
* * *
Three hours later, I walked into a Starbucks in the Loop near my hotel. On a whim, I’d decided to dress down this morning, wearing my plaid skirt and knee sox with a short sleeve turtleneck. I looked, and felt, cute. I was deliberately late, and I’d already conditioned myself for another disappointment, but this time I was in for a pleasant surprise. There he was, with his nose buried in his Crane’s Chicago Business. When he looked up and saw me, he quickly pulled back a chair at his table. Because my expectations were so low, I was totally at ease. I sat down, smoothed my skirt, and asked him the same thing I always ask a guy on a first date: “Do I pass inspection?”
“You’re adorable. Cool sox.”
“Thanks,” I smiled. “I’m channeling my inner schoolgirl today.”
“How about me?”
“Huh?”
“Do I pass inspection, Missy?”
“You’re gorgeous. Just like your picture. Though I have to admit, for a while there I was convinced that wasn’t you.”
“Who did you think it was?”
“I dunno, some male model picked out of the air by a creep who wanted to get off looking at my pictures.”
Ron winced. “I guess I had that coming.”
I relented a bit. “Not really. And I’m sorry I didn’t believe you at first, about your son I mean. How’s he doing?”
“He’s pissed off about losing the rest of the season, but his leg should be fine in time for baseball.”
“So are you going to see him again today?”
“I was at the hospital when I called you this morning. He should be home by now, at his mother’s I mean. I’ll check in with her later, and spend some time with him over the weekend. What can I get you?”
“Oh, an Americano please, no cream.” I waited patiently while Ron maneuvered through the stations, glancing at the Chicago Tribune being read by a man at the next table. “Hotel Killings Baffle Police” was the headline. Let’s hope so, I said to myself.
Ron returned with my coffee, and I took off the lid and waited for it to cool down a bit. “What are your plans for today?” he asked me.
“I’m off to the Field Museum to check out the T-Rex.”
“You’re kidding! I would have thought sure you’d be out shopping.”
“I shopped till I dropped yesterday, in fact I bought a new dress to wear for you, before you stood me up.”
“Ouch.”
“Hey, I’m sorry I’m being such a brat! Thanks for the coffee,” I said, taking a dainty sip.
“No apology necessary. Are you into dinosaurs?”
“No! I’m always looking for different things to do as a chick. The last time I was here, I spent hours at the Art Institute. Today, it’s so lovely out, I thought a little walk along the lake would be nice, and I’ve never been to the museum. Then maybe I’ll try to find another dress to wear tonight, if you’re still up for it.”
“Totally. Where are you staying?”
“The Palmer House.”
“Do you like the Opera?”
My heart skipped a beat. “Love it.”
“Since I’m the one wearing the pants,” he said as he squeezed my bare knee under the table, “I’ll pick you up at seven.”
* * *
The wind played with my skirt as I walked along the lake, crunching leaves under my flats. I was only half-kidding when I told Ron about my inner schoolgirl. More and more these days, I seemed to be making up for lost time, seeking out experiences that I’d missed growing up as a boy.
I was lucky that I was slim and short enough to pass easily for a female, and I was always careful to dress to blend in with the women where I happened to be. In LA, I used to spend my occasional free days in summery skirts, sundresses and sandals, but when I was on the road in a big city like Chicago, I loved to dress up. My afternoon in knee sox was a fun diversion, but tonight Ron was taking me to the Opera! My new dress would have been perfect for it…well, I’d just have to buy another one at the Carson’s in the Loop! Tonight, I was going to knock Ron off his feet!
In retrospect, I’m sure my feelings were a reaction to my near-death experience the night before, and my close call in outwitting the Chicago police. I just wanted to escape again, the surest way I knew how, by becoming another person. The person I should have been born. A pretty woman who happened to have a date tonight with a handsome man. At the Opera, no less!
I figured that if Ron was picking me up at seven, we’d be having a late dinner after the curtain, so I found a little bistro in the Loop and ordered a salad and iced tea. While I was waiting, I stepped out to the sidewalk and bought a Sun Times to see if there was anything about tonight’s performance. Instead, I found a drawing of myself, on page three, staring vacantly into space above this article:
SEARCH FOR MYSTERY WOMAN IN HOTEL SLAYINGS
Chicago – Police have released an artist’s conception of an attractive brunette seen with a man shortly before he was found murdered at the Intercontinental on Wednesday. The victim, whose identity has still not been released, is believed to be connected with an earlier slaying of a transgendered woman in her room at the Sheraton this week. According to sources close to the investigation, the mystery woman shared a drink with the man at a hotel bar before they left together. Any witnesses who may have seen the woman or recognize her are asked to contact Chicago Homicide.
A waitress brought my salad, but I’d lost my appetite. I looked around to see if anyone was staring at the mystery brunette, but I only caught a few male eyes which seemed to be more interested in my legs. I reread the article, trying to guess how hot my trail was. The artist’s sketch was reasonably close, and in other circumstances I might have clipped it out as a souvenir, but it was only a vague likeness. Once I switched back to being a guy, I’d be in the clear for sure…if I had any brains, I’d head back to my hotel right now, and do just that!
What really got my attention was the fact that the unnamed victim was being linked to the Sheraton murder. So the cops had found the knife where I’d put it, compared it to the wounds in the crossdresser at the Sheraton, and connected the dots. Which meant that Gregg, or whatever his name was, really was trying to kill me. I’d worried about that, a lot…at least I wasn’t a murderer! Why hadn’t they released his identity?
I picked at my salad while I forced myself to confront the more immediate question. Was I really crazy enough to continue my masquerade as Missy, with the police on the lookout for her? With her picture in the paper, and probably on the news tonight? Would Ron see it and recognize me?
I suppose all those years living a double life were catching up with me. Maybe that explained how I’d managed to be so cool and calculating last night? Well, what was the worst that could happen to me? If the cops did catch up with me, surely my decision to get rid of the body of the man who’d just tried to kill me would seem reasonable. After all, I was afraid of being exposed as a transvestite! And that was the real downside: if I got busted, I’d be outed nationwide, and my life would never be the same.
I paid for my lunch and started to walk down State Street. Decision time! In half a block, I’d be back at the Palmer House, and if I returned to my room and switched back, my secrets would be safe. Or, I could keep walking to Carson’s, find the perfect dress, and be squired by a gorgeous guy to the Opera, a romantic dinner, then back to my room….
* * *
At seven o’clock, I stood nervously outside the grand entrance to the Palmer House. My new dress was a confection of some kind of black stretchy fabric with a midnight blue taffeta skirt. It clung to my padded breasts and cinched waist, and flared into a lacy cloud that rustled against my knees in the cool autumn breeze. I tugged my new pashmina shawl over my bare shoulders. At least my legs were warm enough in my silky stockings, held up precariously by the lacy garter belt I’d splurged on that afternoon.
A BMW coupe pulled up to the curb, and the passenger window opened. “Hey baby, want to go for a ride?” It was Ron! I waited for the doorman to open the door, and sat down as gracefully as I could in the leather bucket seat. “Wow, look at you,” Ron said.
“Does the gentleman approve of my new dress?”
“Are you kidding? You’re a knockout!”
“Thanks,” I blushed, buckling myself in.
“Did you really get it today?” Ron asked as he pulled away.
“Get what?”
“That dress.”
“Yep. First I went to Carson’s, and I tried on a couple of dresses but nothing seemed right, you really don’t know till you try them on, especially when your body is, well you know, so then I went to Marshall Fields, oh I mean Macy’s, I keep forgetting they changed the name, and I just fell in love with this dress!” Ron had the biggest smile on his face. “What’s so funny?” I asked defensively.
“Missy, listening to you talk about shopping for your new dress, you are such a girl! Seriously, if I didn’t know….”
“Well, let’s just pretend that you don’t know, buster! Okay? I just want to be a girl tonight.”
“Don’t worry.” He eased the car through the gears and I sat back contentedly, listening to soft jazz on the stereo. I wondered if Ron was rich? “How was your afternoon?” I asked him.
“Fantastic. A deal I’ve been working on for two years finally closed.”
“Cool, what kind of deal?”
“I sold my business.”
“Wow, what kind of business?”
“I thought you were just a girl tonight,” he chuckled, squeezing my silky knee. Before I could protest, he went on, “I started an Internet company working from home, built it up, and Yahoo bought me out. They want me to stay on as a consultant.”
So he really is rich! I said to myself. Ron pulled into a parking spot in an underground garage, and scooted behind the car to open my door. I could get used to this! I said to myself as he took my hand and helped me out. “Thanks, it isn’t easy sometimes, dressed like this,” I confided.
He kept my hand as we walked through the garage. I had trouble keeping up him in my stilettos, which he must have sensed, because he slowed his pace. “Sorry Missy, I don’t know how you can walk in those heels!”
“One of the dilemmas of being a woman.”
I can’t begin to describe how exciting it was to hold Ron’s hand, dressed to kill, as we emerged from the garage into a crowd of beautifully dressed Opera aficionados. Ron, by the way, was resplendent in a navy blue suit, crisp white shirt and Hermes tie. I was so proud to be the woman holding his hand, and so happy I’d found the perfect dress!
There was a line at the ladies room, but Ron waited patiently while I made my way in. I didn’t have to go, but after walking in the breeze, I wanted to fluff my hair and make sure my stockings were still up. “What a lovely dress,” the woman next to me said, and who was I to disagree with her?
Ron must have had season’s tickets, because as soon as I got out he walked me directly to one of the doors in the cavernous auditorium, where we followed an usher to our seats. I glanced at my program. Don Giovanni! Mozart’s masterpiece about a philandering rogue and the women he wronged….
* * *
The Opera was fabulous. Sitting there in a cloud of taffeta, I totally lost myself in the experience, enthralled by the music, the costumes, the settings…at intermission, Ron escorted me to the bar, where we sipped champagne and chatted about the performance, as if we really were a sophisticated man and woman. After the second act, we waited for the aisles to start clearing before we walked slowly back to Ron’s car, hand in hand once again. We pulled out of the garage, and Ron started driving north. “Where are you taking me?” I asked him.
“I thought we might have dinner at my place, if you’d like.”
A little alarm bell went off in my head. “That would be nice, but it’s an awful lot of trouble for you!”
“Not really. I sort of planned things out this afternoon.” I bit my tongue and decided to roll with it. I really liked Ron, and now I’d get to see how he lived. We rode in silence for a few minutes, before he pulled into the driveway of a to-die-for townhouse on the Gold Coast. It was beautifully furnished and immaculately clean, and the table in the formal dining room had already been set to perfection. Ron opened a bottle of very expensive champagne, and I sipped it while he busied himself in the kitchen. It looked like he’d ordered takeout from an expensive Thai restaurant, and it didn’t take him long to warm it up.
Over a candlelight dinner, Ron and I got to know each other. I told him about my secret life as a kid, dressing up in my older sister’s clothes after she went off to college, and about how I’d struggled for years to suppress my strange desires when I started dating girls. My failed marriage, and the reemergence of my female self as Missy when I was on the road, intrigued him. “Am I the first guy you’ve met on Craigslist?” he asked me.
Now there was a question! “No,” I answered carefully. “There’ve been a few others. It’s really hard, because so many of the guys either aren’t who they say they are, or chicken out at the last minute. I guess that’s why I reacted so badly when you didn’t show up last night.” I took his hand. “Now I feel like a bitch for being so hard on you! I’m really glad you asked me out tonight, Ron.”
“I’m just glad you gave me a second chance. I can’t believe how like a girl you are.”
“I know how lucky I am, to be able to make it as a girl. There are so many guys like me, crossdressers I mean, who could never pass as women. It’s kind of sad for them.”
“Guys like me, you mean.” I choked on a piece of Pad Thai. “Are you all right?” he asked as I gulped down the rest of my champagne.
“I’m fine. Just surprised, that’s all.” Ron looked crestfallen. “I know you must think I’m a total hypocrite, but I just never expected that.”
“Would you like to see me?” Ron asked hopefully as he refilled my glass. “I have some sexy nighties….”
What a buzzkill! One minute, I was a girl on a date with a handsome man, and the next, I was trapped with another crossdresser who wanted to dress up for me. “Ron, this is really hard for me, of all people, but that doesn’t do anything for me.”
I thought he was going to cry. “I’m sorry, Missy. I’m so sorry.” He looked truly pathetic. I imagined him in bed in an XXL nightgown, getting himself off this week while he talked to me and texted me. Just the thought creeped me out. “I know I’ll never be able to pass as a woman, like you,” he went on. “I just thought it might be fun to hang out.”
“You don’t have to apologize, Ron. I’m sure you make a pretty girl,” I added unconvincingly.
“Not like you. I’ve never even tried to go out. Maybe you could help me?”
He just couldn’t take no for an answer! “It’s getting late, and I have an early meeting tomorrow.”
“I’ll call you a cab.”
* * *
Riding back to my hotel, I felt like a total shit. Why couldn’t I have just played along with Ron? Now I knew how the women who discovered that their lovers were crossdressers felt, how turned off they must be to discover that their men wanted to be girls like them. That’s probably what happened to Ron’s marriage.
The cabbie had the radio on, and the news at eleven shocked me: “Police have released the identity of the man found murdered at the Intercontinental last night. Greggory Alford, who had two convictions for robbery and sexual assault, was also a suspect in the murder of a transgendered woman earlier this week. Police now believe that the brunette seen with Alford shortly before his body was discovered was also transgendered.”
I asked the cabbie to pull behind the Palmer House, so I could use a back entrance. If I could only make it to an elevator and get back to my room without being spotted, I might just be able to put the whole nightmare behind me.
The Craigslist Killer Part 3
© 2014 by Nom de Plume
I paid the cabbie and hurried up a few steps to a side entrance to the Palmer House. It was still unlocked, and I let myself in and made my way quickly down a deserted shopping arcade. I was grateful for the solitude, conspicuous as I must have been in my taffeta dress, shawl and stilettos, but I didn’t encounter a soul all the way to a bank of elevators.
My luck ran out when I stepped into a crowded elevator, full of happy revelers on their way to or from a party somewhere in the hotel. I avoided eye contact with a few of the guys who seemed to be taking an interest in me, and noticed that the button for my floor was already lit. So I pushed the button for the next floor, and waited nervously as the waves of happy conversation surrounded me. When I finally got out of the elevator, I walked down the long hallway to the fire stairs, took them down to my floor, and peeked out the door. There was nobody in sight, and I was able to make it down the hall and into my room without incident.
The message light was blinking on my phone on the nightstand! I was sure the Chicago police had tracked me down…nobody else knew I was here, except my secretary, whom I’d called after I changed hotels. With a feeling of dread, I punched the button for messages and prepared myself for the worst: “Mr. xxxxxx, we got a call from the company you were supposed to meet with on Tuesday, and they were hoping that you could stay in Chicago to meet with them on Monday? I checked and it’s okay with the boss, in fact he’s hoping you’ll be able to. Sorry about your weekend! Let me know if you want me to change your flight.”
What a relief! I kicked off my heels and flung myself on the bed, reveling in the sensations of silk and lace against my skin. So I was stuck in Chicago, as a woman! I had one meeting Friday morning as a guy, then I’d be back in skirts and dresses for three whole days….I had a nagging concern that the sooner I cleared out of town the better, what with the cops looking for Gregg’s transgendered killer, but business was business, and I must have been feeling emboldened by my safe return that night.
I fired up my notebook computer and sent an email to my boss and secretary, telling them I’d stay over for the meeting. Then I went to Missy’s account, where I found several more Craigslist responses, and this email from Ron:
Missy,
I’m so sorry about tonight! I don’t know what I was thinking.
I know I’m not in the same league as you, but I guess I was hoping
you could help me. But what I really want you to know is that I was
really attracted to you, and I feel like such an idiot for turning you off
like that. I know you’re leaving Chicago tomorrow, and we’ll probably
never see each other again, but if there’s any way I could have another
chance with you, I promise it will be different next time.
Love,
Ron
Just what I needed! A lovesick crossdresser…who was handsome, classy and rich! What was wrong with me? I stretched out on the bed in my fancy dress and tried to make sense of my situation.
The Chicago police had a very good description of me as a woman, and knew that I’d spent the night on the same floor as the murder victim. Whether they’d tracked me down to the Palmer House was unknown, but I had to assume it was only a matter of time. So the smart play would be to pack up all my female paraphernalia, FEDEX it back to Los Angeles first thing tomorrow morning, and lay low as a man until I left town.
I looked back at my silky legs, girlishly curled over a froth of taffeta. Maybe there was another way….
* * *
Another morning, another early checkout! This time I left my suitcases with the bell captain, promising to retrieve them later in the day. Then it was off to my meeting, a working breakfast in a conference room at a skyscraper on Adams Street. During a dull moment, I typed out this email to Ron on my smartphone:
Ron, Thank you so much for your sweet message, although
I feel that I’m the one who should apologize to you. I just learned that I have to stay over the weekend, so if you want another shot at me, I’d love to try again with you, Missy
The meeting dragged on and on – I’d have missed my flight anyway – and I found myself checking my smartphone surreptitiously under the table. Finally I heard back from Ron:
Missy, I’m so glad you’re still here, of course I want to see you
again! Are you here all weekend? I have to see my son at the ex’s
this afternoon, then I’m free whenever you are. Are you still at
the Palmer House? You’re welcome to stay with me if you’d like,
Ron
That was too easy…I quickly tapped out this reply to Ron:
You’re the best! I’d love to stay with you, are you sure
that’s not too much trouble? What time are you free, oh and what’s your address? I’ll be arriving as a guy, and change when I get there, if that’s okay…
I barely had time to refocus on the business discussion when my smartphone pinged:
Of course that will be wonderful! I’ll be home by four at the latest, the address is xxxxxxx Astor, see you then!
I ignored some annoyed looks from around the table as I responded:
Sounds good, can’t wait!
“Sorry,” I blithely lied to the group. “Had to change my flight. We’re getting a lot done here today!”
* * *
I ate sparingly during the buffet lunch that was hastily provided at the end of our meeting. I’d be back in women’s clothing again in a few hours, and I needed to keep my girlish figure! When I finally escaped, I took a long walk along the Chicago River before I returned to the Palmer House to pick up my bags. As I was leaving the hotel, out of the corner of my eye I spotted a familiar face: one of the two cops who had interviewed me at the Intercontinental was talking to a hotel security guard in the lobby! I turned away and bolted outside before he could see me, and waited nervously until the doorman summoned a cab.
My pulse was returning to normal by the time I got to Ron’s townhouse. He was waiting at the door when I came up the front steps. “Hi,” he said. “I would never have recognized you.”
“Hi back,” I smiled. “Let me do something about that.”
He took one of my bags and led me upstairs to the master bedroom. “Sorry I don’t have a guestroom for you. My son stays here some weekends, although I guess he won’t be back till he gets out of his cast.” I felt very awkward having Ron see me as a guy, and he must have sensed that, because after a brief conversation about his son’s condition, he left me alone and closed the door behind him.
Finally! I put Missy’s suitcase on Ron’s plush king bed and opened it up, removing the only outfit I’d yet to wear in Chicago: my polka dot tieback blouse and my black skirt with crystal pleats. Hesitantly, I peeked into Ron’s oversized walk-in closet, and got a shock: about a third of it was full of suits, slacks and other guy stuff, but the rest was crammed with an amazing array of women’s clothing. Beautiful dresses, long and short…skirts of every kind and color…enough tops to fill a rack at TJ Maxx…shoes of every description, from flats to heels, including several pairs of sexy boots…I was in a daze as I searched for a hanger for my skirt and blouse. After the closet, Ron’s enormous bathroom was almost anticlimactic: a huge marble tub took up an entire wall, with a fabulous selection of bubble baths, creams and lotions along the side. A plush towel and facecloth had been laid out for me on a standing towel rack, and a matching terrycloth bathrobe was hanging nearby.
Stunned, I took off my suit, shirt and tie, and began filling the tub with some of Ron’s scented bath beads. I imagined that Ron wouldn’t have minded if I’d used one of his razors to shave my legs, but I found mine, and gathered up my makeup and other female essentials and set them out by one of the vanity sinks before I lowered myself into a mound of steaming suds. For the first time since my attempted murder, I was able to totally relax as I surrendered to the bliss of a deep, hot bubble bath, soaking my head under water until I couldn’t hold my breath any longer. Then I lazily shaved myself down, luxuriating in the sensation as I contemplated my host’s situation.
Ron may have been a closet crossdresser, but what a closet! There must be tens of thousands of dollars of women’s clothing, shoes and other paraphernalia in there – I was pretty sure I saw several Gucci bags, the real thing, and some Ferragamo shoes. I already knew that he was rich, and that he yearned to share this side of himself with me, but I had so idea of the extent of his obsession. I analyzed his physique from the standpoint of passing as a woman: he was at least six feet tall, and he must weigh close to two hundred pounds. Although I’d only seen him in long sleeves, I could tell that he was very buff, with broad shoulders and manly arms. So his reluctance to go out dressed was understandable, and so sad!
Well, there was no way I intended to spend the weekend cooped up in Ron’s gilded cage. I’d make him take me out, with me as the girl and him as the guy - after all, isn’t that what he asked for in his email? And maybe, during the day, I’d try to teach him a few tricks of the trade, help him try to find something in his closet that would help to disguise his more masculine qualities, although I was no miracle worker. And there was one thing I’d spotted in his closet that I wanted to try on myself….
Half an hour later, wigged and made up, I returned to the bedroom and fished some lingerie and stockings out of my suitcase. It always felt so good to put them on! I was just about to return to The Closet for my outfit when I heard a tap on my door. “Are you decent?” Ron asked.
“No, but come on in.” I struck a Victoria Secret model’s pose as Ron opened the door and peeked in.
“Oh my God, you are so hot! What I’d give to have a body like that.”
“You’re not so bad yourself, Mister. And since you’re gonna be wearing the pants around here, I’d say your body will definitely do.” I walked over to him, stood up on my tiptoes and kissed him lightly on the lips. “There will be some compensations for you, if you’re nice to me….”He pressed himself against me, and I could feel his rock hard member raging against my tummy. “Goodness, maybe I don’t want you to be nice to me.” I looked up at him and closed my eyes, waiting for him to kiss me. He did, a nice kiss, but I could tell that he was distracted by something. “What’s wrong?” I asked him.
“Missy, while I was waiting I turned on the evening news. There’s a picture of a woman the police are looking for, actually they’re saying she’s transgendered, and she’s very pretty, and she looks so like you. It’s about something that happened at the Intercontinental while you were staying there….” I sank down onto the bed in my slip and stockings, trying to think of what to say. “Missy, you don’t have to worry about me. You’re safe here, and you can stay as long as you like. I just need to know what happened. Maybe I can help you?”
How did I deserve such a man? After the way I’d treated him, no less? I started to shake, then I started to cry, a real woman’s tears, as he sat down beside me and hugged me. “I’m so sorry Ron, I shouldn’t have come here. I don’t want you to get involved,” I sobbed.
“Tell me what happened, baby. Just tell me what happened.”
“Okay, I will, but give me a minute to get dressed and do something about my mascara.” Ron slipped out the door, and I went to the bathroom to repair the damage to my face. I was about to put on the outfit I’d hung in the closet when I had an idea: why not show Ron what Gregg had done to me, by putting on my ruined dress? I fished it out of my suitcase and tugged it on. My whole body shuddered when I zipped it up in the back. Actually, I was surprised to see that my dress didn’t look that bad: there was a rip across the bodice, but nothing that a good seamstress couldn’t cure. I found my stilettos to complete the outfit, and hesitantly waked down the long oak staircase.
Ron was waiting for me in the living room, with a bottle of wine and two glasses. He poured one for me, and waited for me to speak after I gulped it down. “What happened to your dress?” he asked.
It just came pouring out, beginning with how bummed I’d been when Ron didn’t show up (he tried to apologize again but I just plowed on) then the sudden flirtation with Gregg, how strong and forceful he’d been, and how grateful I’d been to have another man in my life. I described our meeting in the lobby bar, how handsome Gregg was, and how he was able to get me to reveal intimate details during our brief conversation, and how I got a little drunk and let him walk me to my room. I even told Ron about the elevator kiss, and how I thought Gregg was about to kiss me again when he savagely attacked me once he got into my room.
“What did you do?” he asked in astonishment.
“It was pure instinct. I fumbled around and found a pair of sharp scissors on the nightstand. He was strangling me! But I managed to stab him in the side, and he let go enough for me to get away, and then I went for his throat, I didn’t mean to kill him but that’s what happened.”
“Christ! He died right there in front of you?”
“It was horrible. I was about to call the police, but then I thought about all the publicity, which would ruin my career – can you imagine? Out-of-town executive dressed as a woman kills Craigslist killer? So I thought about it, and I’m really ashamed of this, but I found a way to get his body out of my room and down the hall, and then I checked out of the hotel the next day, but not before I lied to the police when they came knocking on my door. I’m so fucked,” I said, and the tears started again.
Ron took me in his arms and hugged me tight, rubbing my shoulders. “Baby, you did nothing wrong. Okay, maybe you should have told the police what really happened, but after what you’d been through, nobody could blame you for that. What you did was self-defense, anyone can see that, and once you tell the police what really happened, you’ll be in the clear.”
“That’s just it, Ron. I can’t tell them now. Maybe I should have right after it happened, but now that I’ve lied to them, they might never believe me. I could get charged with murder! And even if I don’t, once the story hits the newspapers, I’ll be totally fucked.”
“Okay Missy, let’s try to forget about it for tonight. You’re totally safe here. And this time, you’re going to get a home-cooked meal.” I followed him into the gourmet kitchen, and helped him set the table, but he was clearly in his element. When we finally sat down to dinner, it was as elegant as the last time, a delicious pasta that I’d never had before. After my fourth glass of Chardonnay, I was feeling no pain, and Ron wisely waved me off when I offered to help with the dishes.
When he was done, I followed him up the stairs to the bedroom. No words were said, but I was sure that we were going to spend the night together, in his bed, and I went all out with my babydoll nightie and matching white stockings. I snuggled under the covers and waited for Ron to join me. But when he came to the door, in long pajamas, he only wished me a good night, turned out the light, and disappeared.
* * *
Despite my disappointment, I slept soundly through the night, and was awakened by the smell of bacon and coffee being prepared downstairs in the kitchen. I pulled the robe in the bathroom over my scanty sleepwear, put on my wig and a touch of makeup, and tiptoed down the staircase to the kitchen in my stocking feet. Standing at the sink with her back to me was a large woman, with an apron tied over her shirtdress. She was humming a refrain from Don Giovanni in a deep voice.
Of course the woman was Ron. I didn’t want to embarrass him, although the sight was so ludicrous that it was hard not to laugh. So I just stood there silently, waiting for him to turn around. When he did, he was so startled to see me that he dropped a dish, which shattered on the hardwood floor. I watched as he got down on his knees and started picking up the broken pieces. I stooped down too, gathering my robe around my knees, and began to help him. Our eyes met, and in spite of myself, I started to giggle. Then he started to laugh, a deep man’s belly laugh, and soon we were rolling around on the floor, in our women’s clothing, carried away by the absurdity of it all.
“I didn’t know you were here,” he finally said, a bit sheepishly. “I wanted to surprise you with breakfast in bed.”
“I’m sorry I startled you! What’s your name?”
“Huh?”
“Sweetheart, if we’re gonna be sisters today, you have to have a girl’s name!”
“Would you really like me to do that?”
“Well, I am your guest, and it is your house, and at the moment you definitely don’t look like a Ron. So unless you’re happy with Ronette, I suggest you think up a nice name for yourself, something pretty. Only you can’t use Missy, I’ve taken it already.”
Another belly laugh from my still-to-be-named hostess. “Thank you, Missy, for being so understanding. I’ve always like the name Caroline….”
“Then Caroline it shall be. So tell me, Caroline, are you a fan of fifties TV shows?”
“I don’t know, why?”
“Because in that outfit you’re wearing, you look like a cross between June Cleaver and Harriett Nelson! Honestly, where did you get that dress? And those shoes?”
* * *
For the rest of that morning, we sat at Caroline’s kitchen table, eating a delicious breakfast and chatting away like two sorority girls. Once I’d gotten over the shock of seeing Ron in women’s clothing, I found myself wanting to help Caroline, and I’m sure her head was ready to explode after the umpteenth tip about hair (her wig was way too long for a woman her age) makeup (not too bad, actually) and clothing (tragic, see above). I asked her how she’d managed to accumulate the incredible stash of clothes, shoes and accessories in her closet.
“Online, all of it.”
“Have you tried all of them on?”
“Yes, and about half of them don’t even fit! Or at least they don’t look very good on me. I’m so hopeless, Missy! That’s why I was hoping you could help me.”
“Listen, I totally understand how hard it is to get started. My big breakthrough came when I finally got up the courage to go out shopping as a woman. You really have to try on a dress to see how it drapes, especially when you haven’t got a woman’s body to begin with. There’s been a lot of trial and error for Missy here, believe me.”
“I could never do that!”
“It’s hard at first, but once you get used to it, it’s so much fun! But let’s be honest, Caroline: I’m really lucky with my body. And as pretty as you are as a girl, well, what I’m trying to say is once you put on heels like the ones you’re wearing, you’re going to tower over everybody, and unless we can find something that sort of masks those big shoulders of yours, it’s gonna be awfully tough for Miss Caroline to make it in the big city.”
“I understand, and after seeing you, I totally get that I’ll never be able to pass the way you do. But to tell you the truth, I really liked being the man on your arm the other night. In fact, I was hoping we could do that again, tonight.”
“I’d love it!”
“Except now that you’re a wanted criminal, or witness, or whatever the cops are looking for, won’t that be terribly risky?”
“Not if you let me borrow that killer blonde wig in your closet.”
* * *
I will never forget the excitement of preparing for my first ever Saturday night date. This was no Craigslist one-night stand in the middle of a business trip – it was an honest-to-goodness weekend date with a rich, handsome man who knew my most intimate secrets. Looking back, I didn’t know quite as much about Ron as I should have, which would soon become all too deadly…but that evening, as I shaved my body, made up my face and got ready to dress myself, my heart was full.
One of the things I did learn about Ron – or Caroline – that afternoon is that he/she was very accomplished with a needle and thread, and the little black dress which I’d bought to wear for him on Wednesday was waiting for me in the closet. But first, I tried on Caroline’s gorgeous blonde wig – it was a bob, slightly longer than my brunette look, and the transformation was stunning. I went with my new garterbelt and stockings again, then a bra and panties, my black slip, and finally my new dress. I already knew it looked good on me, but the sight of the blonde in The Closet’s full length mirror took my breath away. I couldn’t take my eyes off her as she stepped into her stilettos and tugged her clingy dress down over her knees. She was a knockout, and she was me!
Ron was himself again, gorgeous in an impeccably tailored gray suit, crisp white shirt and subdued tie. Since we’d spent the entire day indoors chatting away as girls, I didn’t realize that the weather had taken a nasty turn until Ron got his Burberry’s coat out of the hall closet. My dress had cap sleeves, and my pashmina shawl would be no match for the Chicago winds. Not a problem: Ron accompanied me back to The Closet and helped me select a cute black jacket that was a tad big for me, but went perfectly with my dress. Then it was off to Morton’s in his BMW, a few short blocks away. Ron must have been a regular, because as soon as the maître d saw him, we were ushered to a romantic little booth in the crowded restaurant.
Ron’s reputation as a connoisseur of expensive wines preceded him, and the sommelier materialized with a bottle of Sonoma Coutrer. After the uncorking and tasting ritual, we settled into easy conversation about the menu. A waiter appeared with a trolley full of meat and fish samples, even a live lobster, and we each ordered filet mignon with a side of creamed spinach to split. It must be obvious that every detail of that evening is engraved in my mind, including two snippets of conversation that loom large in my memory.
At one point, I asked Ron about what happened to his marriage. I assumed he’d tell me that his wife was freaked out about his dressing as a woman, and left him over it, but that was only part of the story. It seems that Ron had always had a gay streak, which he mostly suppressed over the years, but yielded to from time to time. There is a robust gay community in Chicago called Boys Town, and Ron had discovered the delights of bottoming there.
I wasn’t shocked, because I’d played on the same turf. But I’d always been dressed as a woman, which somehow didn’t seem gay to me. Sitting there in Morton’s, in a beautiful dress, on a date with a handsome man, in my mind I was really a woman, and I’d convinced myself that sex with a man was a natural act.
At another point, we talked about the fix I was in. Ron had learned a bit more about the police investigation. It seemed that the tgirl Gregg killed at the Sheraton - and me - weren’t his only victims: over the past six months, he’d left a trail of transgendered women whom he’d robbed in their hotel rooms. The police speculated that he singled out transgendered women from out of town because he knew that they would be less likely to complain to the police, which would force them to reveal to the world that they were crossdressers trolling for sex with men. I had to agree with them!
Fortunately, the name of the man from Los Angeles who had been interviewed in his room at the Intercontinental the night of the murder had not been picked up by the media, and I was pretty sure that if I resurfaced as a male on Monday and flew back to Los Angeles, my troubles would be behind me.
* * *
After a long, lovely dinner, Ron drove me back to his home. On the way, told him that I hoped he’d feel comfortable staying in his bedroom with me. “I promise I won’t bite,” I teased him.
Ron squeezed my knee once again, and he was delighted to discover a garter clipped to my stocking. “Only if you let me undress you.”
“I think that can be arranged,” I said. By that point, after all the frustrations of the past week, I was incredibly horny, and more than a little drunk, and I was bound and determined to take Ron to bed. When we got back, I asked him to give me a moment, and I closed myself in the bathroom to freshen my makeup. The blonde in the mirror looked pretty and confident.
Ron was waiting for me in bed, his clothes neatly folded on top of the dresser. The lights were turned down low. Without a word, I kicked off my heels, pulled back the covers, and slithered in next to him. He kissed me, a long, lovely kiss, then he reached behind me and started unzipping my dress. I was docile and willing as he gently lifted it over my head, and he caressed my silky slip before he took that off too. He seemed surprised that I wasn’t bound up in Spanx or a body briefer, but after years of dieting, situps and crunches, I did quite well with a padded bra and panties, and the payoff came that night as Ron continued to undress me. While he did, I started to push his hot buttons, nibbling and breathing in his year, teasing his nipples with my long fingernails, and gently stroking his penis. He moaned when I played with him, but he wasn’t getting hard.
Meanwhile Ron was rubbing my legs in my nylons, which was incredibly arousing. I knew that I couldn’t hold out much longer. “What’s wrong, baby?” I whispered in his ear.
“I’m sorry, Missy. I just can’t.” I knew from the night before, when I’d kissed him before dinner, that his body was capable of a rock hard erection, and I wasn’t going to give up on him.
Maybe a little crossdressing would help him? I sat up and slowly unclipped a nylon from its garters. After I took it off, I started rolling it up one of Ron’s legs. He was laying back on the bed, and a look of sheer ecstasy came over his face as I slid it higher and higher. I unclipped my other nylon too, and as I rolled it on him, his penis came to life before my eyes. I’d never seen anything like it: one minute it was soft and tiny, and the next minute it was standing straight up, at full attention, ready and waiting for me to climb aboard.
My condoms were somewhere in my suitcase, but between the two of us, there was plenty of pre-cum to spread around…before Ron knew what was happening, I impaled myself on him, straddling him like a horse, and started riding him up and down, up and down. I was so ready, and he was too. I’d never made love to a guy without protection before, and he felt so hot inside me! When he came, I could feel his jism spurting deep within me, and then I came, a gusher that splashed all over his chest as the sweet waves of pleasure curled my toes.
When we were done, I lifted myself off and snuggled next to him. “Sorry about the mess,” I sighed.
Ron didn’t say anything for some time. When he finally spoke, I thought me might be crying. “Missy, I’m so sorry.”
“Sorry about what? That was the best sex I’ve ever had.”
“Me too, but there’s something I haven’t told you.”
“What, that you want to be a girl? I can live with that….”
“No, that’s not it. I have H.I.V.”
The Craigslist Killer Part 4
© 2014 by Nom de Plume
I lay there in stunned silence, my death sentence ringing in my ears. “I have H.I.V,” Ron just told me. How many times had I warned myself about the dangers of dating on Craigslist? How many guys had I blown off because of the teeniest suspicion that they might not be safe?
How much time did I have?
I bolted out of bed and raced into the bathroom. There was a bidet next to the toilet, and I turned it up full blast and squatted over it, hoping and praying that the jet of ice cold water would somehow cleanse me. The water gradually warmed up, and I played with the controls, keeping it as hot as I could physical stand it, for what seemed like an eternity. When I couldn’t take it any longer, I dried myself off, wrapped the bathrobe around myself, and returned to the bedroom.
Ron was curled up in the fetal position, softly sobbing, “I’m so sorry. Please don’t hate me.” He looked so pitiful, I actually felt sorry for him, in spite of what he’d done to me. After all, I’d been the aggressor, forcing myself on him before he could stop me….
I sat down next to him. “Why the fuck didn’t you tell me?”
“I never wanted to have sex with you, Missy. I just wanted to dress up with you, to be your girlfriend,” he sniffled. “But you were so beautiful…even then, I didn’t think I could, and I didn’t know you were going to, before it was too late. And then…God, it felt so damn good! And it’s been so damn long…but I could have stopped you. I’m so sorry. You trusted me,” he sobbed, “and I should have told you from the very beginning.”
“How long have you had H.I.V.?”
“I found out just over a year ago. Right before my divorce.”
“Did your wife catch it too?”
“No, thank God. That was a whole other nightmare. But she’s been tested several times, and she’s okay.”
A glimmer of hope for me? “How can I get tested?”
“You have to wait at least a month before taking the test to be sure.”
Just what I needed to hear! I’d be in agony till I found out, and if the test results were bad, I’d be a dead man. “How are you doing with it?” I had to ask.
“You mean physically? I’m on a shitload of ridiculously expensive drugs, a cocktail they call it, but so far so good. With any luck, I’ll hang in there like Magic Johnson. But that’s not the hard part.”
“What could be worse?” I asked bitterly.
“The mental part. Trying to live a normal life in front of my son. Trying to meet new people, and not have them run for their lives when they find out. I’d totally given up on having a sex life, until….”
“Until idiot me!” All of a sudden I was mad, steaming. It was like the seven stages of grief were playing out at warp speed. I was sick to my stomach…sick of pretending to be a woman…sick of Ron…sick of my entire fucking life…I staggered back to the bathroom and was violently sick.
I kneeled, naked, on the cold marble floor, retching my guts out. When I was finally done, I walked forlornly back to the bedroom. Ron was nowhere to be seen. In despair, I hurled my wig across the room, threw myself into bed, and collapsed into a restive sleep.
* * *
The next morning, I was up early. I’d slept in my makeup, so my first project was to scrub my face clean, get the polish off my nails, and take a long, hot shower. Then I put on a turtleneck and khakis, and hurriedly stuffed Missy’s suitcase full of all of my women’s clothing and miscellaneous female accessories. I used my cellphone to summon a cab, walked downstairs, and quietly let myself out. There was no sign of Ron.
I told the cabbie to take me to the Intercontinental. Rooms were available, and as soon as I checked in, I walked over to a nearby FEDEX office. They were just opening, and I used a personal credit card to send Missy’s suitcase to my home in Los Angeles. Then it was back to my room, where I ordered a hot breakfast from room service, and spent the rest of the morning scouring the Internet for anything I could find about H.I.V., gay sex, and AIDS.
After several hours of research, I was feeling a little better. Although I was certainly in a high risk category, it was by no means certain that I was infected. The douching I’d instinctively performed moments after having sex with Ron was a definite plus, and there’d been no blood that I could see after my anal intercourse with him. He was on the small side (which is always better as far as I’m concerned) and cut, which also helped. I’d have to wait 30 days before testing myself for the AIDS virus, and I had no idea how I was going to make it that long without losing my sanity, but there was some hope for me.
My other problems paled in comparison, including the manhunt for me by the Chicago police. Checking back into the Intercontinental had been a simple act of misdirection: I reasoned that they’d be unlikely to look for me here, and if they did find me, it would be easier to feign innocence. I’d just lay low through the weekend – the weather was miserable, a wintry mix of rain, sleet and snow, and my luxury room seemed like a pretty safe refuge.
My thoughts turned to Ron. I know it must seem strange, but I was not angry with him. If anything, I felt sorry for him. He was living the nightmare that I feared for myself, with no good outcome. At least he was rich enough to afford the best of medical care, including that cocktail of drugs he told me about. After reading about the medical advances against AIDS that morning, I reasoned that he had a shot at a reasonably decent life, but that wasn’t the life I wanted for me.
* * *
The week before Christmas, back in Los Angeles, I steeled myself as I opened my post office box. There it was, an envelope from the community health organization I’d gone to anonymously a month after my return from Chicago. After an awkward wait in a nasty lobby full of godforsaken men and women, where I filled out a form using a bogus name with my PO box as my address, the H.I.V. test itself was mercifully quick: a quick swab of the roof of my mouth, and I was officially in limbo.
The past 30 days had been like something out of the Twilight Zone. Every time I sneezed, or scratched an itch, I was certain that I was dying of AIDS. Some of my time was put to good use: for the first time in my life, I prepared a will (leaving everything to my ex-wife after a sizeable bequest to my college) and my diet improved, as if by eating right I might ward off the deadly virus. At the office, I threw myself into a miserable project that everyone had been avoiding, earning huge brownie points for my long hours and manic compulsion to finish it. When I returned to my condo late every night, I spent hours tossing and turning, dreaming fitfully about how I was going to spend the few good months remaining before my body was racked by disease.
And I exchanged countless emails with Ron. He’d left me alone while I was in Chicago, but when I got back home I was greeted by the first of many, many messages of apology and encouragement. Having already lived through my nightmare, he was well aware of what I was going through, and his words of support kept me going. In return, I offered him endless tips on how to improve his female fashion sense (“try that black top with a long skirt, black is slimming”) and received dozens of pictures in reply. By the end of the month, he was looking more and more presentable as a biggish, handsome woman, of which there are very many in Chicago – the City of Broad Shoulders has the same gene pool for both sexes.
Missy, meanwhile, had gone cold turkey. I hadn’t even opened her suitcase since FEDEX delivered it. Normally, I was manic about laundering her undies, mounting her wig on a Styrofoam head, and the like. I suppose part of me was denying that I was ever going to dress up as a woman again, and part of me was acknowledging the likely end of my wild sex life. At least I’d had my moments, climaxing in my best ever orgasm with a total stranger from Craigslist, I reminded myself ruefully again and again.
And so my moment of truth finally came, and once I returned to my car in the post office parking lot, I tore open the envelope with trepidation. There was a lot of mumbo-jumbo as I raced through the form, until I found the magic word I’d been praying for: NEGATIVE. I didn’t have H.I.V.! I wasn’t doomed to a horrible death from AIDS! I’d rolled the dice, had unprotected sex with an H.I.V. case, and would live to tell the tale!
I know it must sound callous for me to refer to Ron that way, but one of the things I’d developed over the past month was a gallows sense of humor, which Ron shared. I’d promised him that I’d let him know if he infected me, so I punched his number into my car’s hands-free on the drive back home. “Hi Missy,” he answered.
“Good news, baby. You didn’t kill me.”
“You mean you got your test results?”
“Yep. I’m a negative.”
“Thank God!” I could tell from Ron’s voice that he was genuinely happy for me. “What a load off,” he continued. “I’ve been so worried about you….”
“Listen, Ron, I know you felt guilty about not telling me, but you’re off the hook. No harm, no foul, big boy.” I felt a pang of sadness for him. “If only you were so lucky….” I could tell that he was starting to cry, so I got off the phone as quickly as I could.
I turned on the radio, and every station seemed to be playing Christmas carols. In my angst over my condition, I hadn’t even allowed myself to think about the Holidays, and now that I had my life back, it was too late. My ex-wife was headed back east for a gathering of her extended family (a ritual I always loathed) and my own side of the family was dysfunctional, to say the least.
Maybe I’ll go somewhere, I mused as I pulled into my garage. Hawaii? Europe? I was pondering the pros and cons as I switched on my PC, to find this email from Ron:
Missy, You have no idea how happy I’m feeling right now, knowing that the biggest mistake of my life (well, make that the second biggest LOL) didn’t hurt you. I think you told me several weeks ago that you were making no plans for the Holidays, so I’m taking a chance and attaching a little present – let me know if you can come, I’d love to see you! Ron
Attached was a first class airline ticket to Chicago, departing Christmas Eve and returning New Year’s Day.
The Craigslist Killer Part 5
© 2014 by Nom de Plume
You can scratch “flying pretty” off my bucket list. It was something I’d always longed to try, but never had the cajones to do it. What if someone recognized me? Or a boorish TSA agent called me out in a crowded terminal? Of course, all of the other times when I “packed for two” I was flying on business at company expense, but this trip was purely for pleasure, and anyway a lot of my old hang-ups no longer seemed so important since my brush with death from AIDS.
Packing presented some special challenges: what did a girl wear in Chicago in the middle of the winter? My trench coat, of course, plus pants, boots, and a long skirt or two (preferably in red or green) and something sexy in case Ron asked me out to dinner again at a romantic restaurant…but I’m getting ahead of myself. My immediate challenge was deciding what to wear on the plane!
If I’d been flying coach, I’d have worn pants for sure, but in first class I decided that a skirt might work. Unfortunately, I made the mistake of wearing a very short skirt which I thought would be safe with black tights and calf length boots. It was red plaid, and I thought it was a very cute look for Christmas.
Except I didn’t figure on having to unzip my stupid boots while juggling my coat, purse and suitcase to put everything on a conveyor belt and walk through security in my tights! Oh well, the part I’d dreaded the most – presenting my boarding pass in my male name with my driver’s license picturing the real me – was a big nothing, as if the guy saw it every day. So once I found a chair and put my boots back on, I composed myself in the nearest ladies room and headed straight for the bar. Two vodka tonics later, I proceeded to my gate, where the first class passengers were just boarding.
I had a little buzz on as I waltzed down the jetway, tugging Missy’s suitcase behind me, my coat over my arm, a purse on my shoulder…it was Christmas Eve, and I was flying to the snow! As a pretty woman! To meet a person whom I’d both loved, and hated, with an intensity that I hadn’t felt since the breakup of my marriage. I had no idea whether it would be Ron or Caroline who would be meeting me at O’Hare, and at that moment I really didn’t care. Like me, Ron led two lives, and maybe by helping him cope with the duality of his existence, I might learn some things about myself?
But for the next four hours, the only thing I had to worry about was drinking too much first class booze on the plane! After the ordeal I’d just been through, I was ready to kick back and enjoy life again, in silk and lace for the first time in over a month. What a thrill it had been to open Missy’s suitcase, and busy myself with the mundane tasks of female existence: washing my wig, laundering my lingerie, and rummaging through the back of my closet for my winter wardrobe.
When I stepped onto the plane, I glanced at my boarding pass to locate my seat. 3D, a window seat. Sitting next to me in 3C was one of the most beautiful women I’d ever seen, an LA 10 all the way. A model? An aspiring actress? She looked up and smiled at me after I stowed my suitcase and coat in the overhead bin and sat down as gracefully as I could in my short skirt. “Cute outfit,” she said, “I love your skirt.”
“Thanks,” I smiled back. My experiences in conversing with real women were woefully limited – other than a few short words with cashiers and waitresses, I’d never really spoken to one while I was dressed as one, and I was sure that she must be able to see right through me. But she didn’t seem to notice, or care. Just then a flight attendant appeared, and she frowned as she looked at me. “Mr. Xxxxxx?” she asked hesitantly. “That can’t be right….”
The downside of flying first class! “Oh, he’s my boyfriend,” I lied, thinking fast. “I was sitting back in coach, but he swapped seats with me as a Christmas present.”
“My kind of guy,” she chuckled. “Would you like anything to drink before takeoff?”
“A vodka tonic would be nice,” I replied. The girl seated next to me asked for mineral water, and went back to scrolling through messages on her smartphone. She must have to fight them off, I mused as I settled into my large leather seat. The flight attendant returned with my drink, and I sipped it gratefully as the cabin crew went through the preflight announcements.
The passengers were told to switch off all electronic devices, and my beautiful seatmate turned her attention to me. “Does he have a brother?” she asked.
“Huh?”
“Your boyfriend. He sounds so cool,” she said.
“Oh, him. Yeah, he’s pretty cool,” I said. “As if you need help with men….”
She shot me a quizzical look, and I think it slowly dawned on her. She couldn’t be sure, but she could tell that something wasn’t quite right. So much for my female conversation skills! By this point I was feeling no pain, and I always lost my inhibitions when I drank, so I decided to come clean with her. “Can I tell you a secret?” I asked.
“Sure.”
“I’m not really a girl.” Her eyes widened. “I hope I haven’t shocked you.”
She shook her head. “No, not really. Not in this town. Although I have to say, you really fooled me. Are you transitioning?”
“No! I live a double life. Do you really think I pass as a woman?”
“Oh yeah, you look more like a woman than most women. How long have you been at this?”
I glanced around the cabin to see if any of the other passengers were hanging on every word, but none of them were paying the slightest attention to us, except for one guy two rows up, across the aisle, who kept stealing glances at my seatmate. “Since I hit puberty,” I confided in a hushed voice. “I wish I could stop sometimes, but it feels so damn good, and I love being able to experience life from the other side.”
“I get that,” she said. “A lot of women I know wish they were guys. Personally I dig being a girl, I love the clothes and stuff, and I don’t think I could handle all the macho shit.”
“I know! I hate that too. But being a guy is okay. There are some huge advantages….”
“I’ll say. I wish I could travel anywhere I wanted to, alone I mean, or go for a walk in the middle of the night sometimes, but for girls it’s hard.”
We chatted on like that for quite some time. When our menus were produced, I switched over to white wine, and so did she. She started to catch up with me. “So tell me,” she asked, “do you really have a boyfriend back in coach?”
“No! Although that wasn’t a complete crock. This guy I know bought my ticket, and he’s meeting me at the airport.” For some reason, I felt insanely proud of that. “We’re spending the holidays together,” I added.
“That is so cool! How did you guys meet?” Our dinners were served, and between bites and sips, I told her almost everything, beginning with my Craigslist post (“Omigod, you really went there?”) then our night at the Opera, my discovery of Ron’s crossdressing (“Sounds like your soulmate”) to our big night together (I’d had an awful lot to drink by then) and Ron’s shocking revelation (she was speechless) to the results of my H.I.V. test. Of course I left out the attempted murder and my escape.
When I was done, she was silent for some time. “Wow,” she finally said. “And I thought I had an exciting life. You’re like some kind of superhero, with a secret identity.”
“Not really. I’m just a messed up guy. Anyway, what’s your life like? You must be in fashion or entertainment, right?”
“See, you’re telepathic too. I’ve been modeling since high school, and I’ve gotten a few parts in TV and the movies, but it’s tough.”
“So what brings you to Chicago?”
“Home for Christmas!
* * *
We both dozed off after dinner, and when I woke up she was in the lavatory. I had a small travel kit in my purse, and I took my turn when she was finished. We exchanged knowing female glances as we passed each other in the aisle, and once again the dweeb two rows up couldn’t take his eyes off her, although he paid no attention to me. What am I, chopped liver? I asked myself.
I felt even worse when I surveyed my reflection in the lavatory mirror. My lipstick was gone, my wig was a little tousled, I had the beginnings of a five o’clock shadow, and to top things off I had a splitting headache from all the booze! After I took three aspirin, I brushed my teeth, gargled with a sharp mouthwash, and ran a small electric shaver over the stubble on my face. It took forever to hike up my skirt, pull down my tights and panties and relieve myself in the miniature toilet, but once I’d put myself back together, freshened up my makeup and brushed my hair, I felt like me again – the pretty girl me. On my way back to my seat, I noticed that several of the men, including the dweeb, were checking me out.
The seatbelt sign was on, and we were almost on the ground. My galpal handed me her business card, and told me to call her if I wanted to hang out when we got back to LA. As a guy or a girl? I wondered. But I never had a chance to ask her. As soon as we touched down, she was back on her smartphone, and I barely had a chance to say goodbye before she got off the plane.
Let’s see: purse, suitcase, trench coat. Once I had myself together, I joined the milling throng in the terminal, everybody in a hurry to get home for Christmas. My smartphone buzzed with a message from Ron: he was waiting for me on the curb.
I tapped back a message that I was on my way.
* * *
When I walked out into the Chicago night, a blast of arctic air took my breath away. Even in my tights, my legs were instantly freezing, and I stopped to put on my gloves before I searched for Ron’s BMW. There it was, about a hundred yards away. By the time I reached his car, the frigid air had cleared the fog of alcohol out of my head, and I wasn’t surprised to find Caroline seated behind the wheel. She popped the trunk from the inside, and I stashed my suitcase before I opened my door and sat down beside her.
We stared at each other in silence for some time. As my eyes adjusted to the dim light, I surveyed her appearance with approval. She was wearing “my” blonde wig, which perfectly framed her beautifully made up face, a long tweed skirt and a soft cashmere sweater. “Hi Caroline,” I said at length. “You look sensational.”
“Hi Missy. So do you, as always.”
Suddenly I was overwhelmed with emotion. I reached across the console and took both of her hands. “Thank you so much for flying me here. I’m so happy to see you again,” I sniffled.
“I was afraid you might be mad at me for dressing like this….”
“Sweetheart, after what I’ve been through, it’s gonna take a heck of a lot more than seeing you in a skirt to piss me off.”
The ice was broken, and we chatted away like long-lost girlfriends as Caroline drove through the wintry night. There was snow piled up along the roadside, and flurries filled the night sky. “I can’t remember the last time I had a white Christmas. It’s so beautiful,” I said.
“You’re lucky you didn’t fly in last night. The airport was closed for hours.”
“I can’t believe I’m here. Do you have any plans for tomorrow? With your family, I mean?”
“Yeah, I hope you don’t mind, but I’ve got to slip away – as Ron, of course – tomorrow morning to have brunch with my ex and son.”
“Don’t be silly, I can sleep in!”
I was feeling a little jetlagged by the time we got to Ron’s townhouse, and of course I’d already eaten, so we just sat in the living room and talked over coffee and cookies. “Did you bake these? They’re delicious.”
“No! They’re from a bakery. Are you sure you don’t mind my being away tomorrow morning?”
“Nope, I haven’t had a good night’s sleep since I left Chicago. You might have to wake me when you get back!”
I wasn’t really surprised that Caroline suggested separate bedrooms, after what I’d been through with Ron. She insisted that I take the master again, and as soon as I wiped off my makeup and put on my nightgown, I was dead to the world.
* * *
Christmas morning! I glanced at the clock on the nightstand: it was after nine o’clock. I hadn’t had a sleep like that in ages…Ron must be long gone, not to return for hours, I hoped. I yawned and stretched in my silky nightgown, then took my time making the bed before I draw a hot bubble bath in the oversized tub and treated myself to a long, luxurious soak, shaving my legs and the rest of me. Then it was time to decide what to wear: I’d packed my warmest things, including a blue wool skirt and matching turtleneck sweater, which would be perfect for the tasks I planned. So I dug my white bodybriefer, slip and nude nylons out of my suitcase, took my time putting on my makeup and wig, and slowly dressed myself, reveling in every moment as the silk and lace caressed my skin.
Why do men crossdress? I wondered for the millionth time. Why is it so damn irresistible? It had to be more than the feel and touch of those marvelous fabrics that boys were forbidden to wear…there was something empowering about them, something that only girls could share, that drove me crazy. I’d read every psychological treatise on the subject, and nothing answered the question.
No matter. In the here and now, I was a woman once again, in a totally safe environment, in the home of the man – or was it the woman – who had rocketed to the center of my universe. The least I could do for him – her – was to fix Christmas dinner!
A quick survey of the kitchen the night before had confirmed that Ron, or Caroline, had laid in the provisions for a delightful dinner for two: Cornish game hen, potatoes au gratin, and a green bean casserole from Whole Foods were waiting to be cooked in the gourmet oven. I found a flowered apron in the pantry and went to work.
I was so busy I’d lost track of the time when I felt Ron’s arms gather around me from behind as I hunched over the kitchen counter, cutting some vegetables for the salad. “Merry Christmas,” he said.
I spun around and kissed him. He tried to break away, but I wouldn’t let him, and soon he was as into it as I was, throwing himself into that kiss like there was no tomorrow. When we finally came up for air, he asked, “Are you sure it’s safe for you?”
“Totally. I’ve done my research. You can’t get AIDS from a kiss!”
“What are you doing?”
“Fixing Christmas dinner for my man. Make yourself useful by pouring us some drinks. And prepare yourself for the best Christmas of your life, Mister.”
The rest of that Christmas day is a blur - a delicious, delightful blur of sensations and surprises for the both of us. First, we snuggled on the living room sofa as we sipped one of Ron’s killer cocktails. He seemed very tentative in the touching department, until I gently took his hand and slid it up my skirt. When he caressed my legs through my pantyhose, I felt an electric shock that made me yearn for more…then, the timer buzzed and it was time for Suzy Homemaker to get busy. Soon the table was set and dinner was ready to be served, to the accompaniment of a sublime red wine that Ron opened to breathe.
Before we sat down, I excused myself and raced upstairs to change into the outfit I’d been saving for Christmas dinner. First, I swapped my lingerie from white to black, including a long, lacy slip to wear under a long skirt in a red, green and black plaid. A sheer black blouse and a long scarf with reindeer and holly pulled the whole outfit together. I wished I had some shimmery nylons to complete the look, but they were impossible to find in LA – maybe Chicago women were more festive? – so I went with sheer off-black stockings and a cute pair of patent leather flats with silver bows.
I was struggling with my candy cane pin, trying to fasten it through my scarf, when I heard a tap on the door. “Are you okay in there?” Ron asked.
“Yes, please come in and make yourself useful.”
“Wow,” Ron exclaimed. “You look beautiful! I love that skirt.”
“Thanks,” I blushed. “Can you pin me?” I handed the pin to Ron, and stood close to him as he patiently fiddled with the delicate mechanism and snapped it shut. Then I stood up on my tiptoes and gave him a soft, sweet kiss that he returned in kind. I could feel him hardening as I pressed myself against him, an encouraging sign of things to come that night….
* * *
Dinner was delicious. It was amusing to sit at opposite ends of the long dining room table, like the lord and lady of the manor, making small talk as we savored the moment. Of course, our small talk wasn’t your normal man-and-woman conversation:
“You’ve really raised your game in the girl department,” I remember telling him.
“You’ve been a big help. Have you notice how much stuff I’ve cleared out of my closet? The Goodwill loves me, and God knows I need the deduction this year.”
“So besides meeting me last night, has Miss Caroline ventured into the great outdoors?”
“No, that was my first. Do you really think I’m presentable?”
“Um hmm. That outfit you wore last night is really cute.”
“Do you think I could wear it to go shopping?”
“Sure, can I come too?”
“Oh Missy, that would be a dream come true for me!”
“Seriously, let’s do it! There are always super sales the day after Christmas.”
“What will you wear?”
“Pants! I froze my ass off in my skirt and tights last night.”
“I’m afraid to wear pants, when I’m a girl I mean.”
“I know, it took me a long time to get used to it, but if you find the right pair, and pad your butt, they can be very girly, and in this climate, if you don’t wear pants, you’re gonna stick out like a sore thumb out there.”
“So you’re telling me that I’ll be more likely to pass in pants?”
“This time of year? In Chicago? Totally.”
* * *
After dinner, I helped Ron with the dishes, then we settled on the sofa for coffee and cookies again. There was a perfect Christmas tree in a corner of the room, and I noticed a large package under it, beautifully wrapped with ribbons and bows. As if he was reading my mind, Ron walked over to the tree, and returned with the package. “Merry Christmas, Missy,” he said.
“Oh Ron, I thought the airline ticket was my present!”
“That was for me. This is for you.”
My hands were trembling as I tore off the wrapping. “It’s so pretty, I hate to mess it up,” I said nervously. When I opened the box, I’m sure I gasped: it was a gorgeous, full-length sable coat, which must have cost a fortune. I stood up and wrapped it around myself, luxuriating in the feeling of my first fur. Now I knew why women longed to wear them from time immemorial.
“Now you can wear a dress in the winter,” Ron said.
“I love it! I just love it!” I said as I vamped around the room.
“It may not work in LA, but here in Chicago, women don’t seem to have a hangup about fur,” Ron went on.
“I love Chicago, I love my fur, and I love you.” Did I really just say that? Ron seemed surprised too. “Come upstairs in a few minutes. I have a present for you too.”
I raced up to the bedroom and hung my treasure in the oversized closet – plenty of room in there now. Then, after I got undressed, and freshened my makeup in the bathroom, I dug my sexiest nightgown and some fishnet stockings out of my suitcase and lovingly put them on. There was also a small package in my suitcase, which I placed on the nightstand. I stashed a few other things under the covers, then I curled myself up on the bed and waited for my man.
There was a tentative tap on the bedroom door. “Can I come in?”
“Yes, sir.”
Ron stuck his head in, and frowned. “Missy, please. You’re killing me.”
“Don’t you like what you see?” I purred.
“Yes, dammit, but those days are over for me! Don’t you remember what I almost did to you?”
“I’ll never forget it. But it was still the best sex of my life, and if we’re super-careful….”
He sat down on the edge of the bed. “Missy, be reasonable. I’ve got H.I.V. If I’d told you that upfront, you never would have gone out with me.”
“True. But I’ve learned a few things since then, about myself, and about H.I.V. And about us.”
He started to cry. “Missy, I don’t want to hurt you. Last night was so special. Can’t we just be girlfriends?”
“I want you to tell me the truth, Ron. When we made it last time, with you as they guy, didn’t it feel good to you?”
“It was amazing. You think it was the best sex you ever had? It was even better for me. But we can’t do that again, ever, not even with a condom. I’m not going to have that on my conscience, if something goes wrong,” he sobbed.
I waited until he calmed down, then I handed him his present. “Open it.”
With a sigh, he tore open the package. When he saw what I got for him, he actually laughed. “You’ve got to be kidding.”
It was a long, thin, plastic dildo with a bulbous tip. “It vibrates,” I said hopefully. “See?” I twisted the knob, and it started to hum. “Please, Ron, trust me on this. I’m not going to take any chances with you. Just take your clothes off, and let me work my magic.” Shaking his head, he stood up and stripped down to his shorts. “Lie down,” I commanded him. He did, and after dimming the light, I lubed up his present and lay down beside him. I tugged off his shorts, and went to work on him.
It’s amazing how much sex you can have with an H.I.V. carrier if you’re careful. That night, we barely scratched the surface. While I teased his penis and balls with the dildo, and scruffed one of his nipples with my long fingernails, I kissed him passionately, stopping sometimes to nibble and breathe on his ear. I could tell that he was getting aroused each time his penis twitched, although he wasn’t terribly hard. That wasn’t going to matter: when he was just firm enough, I stopped for a moment to tear open a fruit flavored condom, which I carefully rolled onto him. Then, while I started to suck on him, I gently probed his butt with the dildo, carefully inserting the tip into his ass. He was gasping and moaning as I screwed it higher and higher, and when it was in all the way I twisted the knob all the way to high.
I’ll never forget the feeling of power I had over him at that moment. I glanced up at him once, and his face was contorted in a grimace of pure pleasure. Then I went back to work on the condom, sucking him in synch with the deep thrusts I was making with the dildo. Up and down, in and out…up and down, in and out…faster and faster, again and again, until he cried out in ecstasy, and I felt him throbbing in my mouth as he came and came and came.
When he was finally finished, he let out a deep sigh as tears rolled down his cheeks. “Oh Missy,” he whispered. “I never thought I’d feel like that again. That was so fucking good.”
“See, I told ya. Now it’s my turn.” I reached under the covers and produced a matching dildo. “His and hers,” I told him. After I lubed it up, I held up a condom in each hand. “You were a strawberry,” I said. “Do you feel like banana or orange?”
“What a woman! Make mine banana,” he laughed.
I pushed Ron over and lay back on the same pillows. “I want to feel everything you did.”
“Yes, ma’am.” With that, Ron went to work on me. He proved himself a very patient, attentive lover, and soon I was rocking back and forth as he sucked and pronged my trembling body. He was slower than I was, and very tender, and the twin pleasures were incredibly sublime, taking me to place I’d never been before, an incredible plateau of pure desire. I wanted to stay there forever, but I knew I couldn’t hold out much longer. Finally, I lost myself to a mind-bending orgasm that went on and on and on….
“Was it good for you too?” he asked me.
“Oh baby, that was the best. You’re the best. Did I tell you that I love you?”
“You did, and in case you’re wondering, I love you even more.” We lay there for a long time, cuddling and petting each other, and we fell asleep in each others’ arms.
Sometime during the night, I woke up to feel Ron’s hardening penis pressing against my thigh. I started to play with him, and at first I thought he was still asleep, till I felt him reach over and begin to stroke me. We pleasured each other that way, easy does it, until we both came together, simultaneously orgasms that were indescribably sweet. I was in love.
* * *
The next morning, Ron was up early, and I heard him rummaging through his closet before he disappeared. I got up too, still in my sexy nightgown and fishnets, my wig a tangled disaster. I took my time brushing it out, then I treated myself to yet another long, luxurious bubblebath in the massive tub.
Today we were going to go shopping, as girls, and a glance out the window showed that it was going to be a miserable day, with a mix of rain and snow. Yuck! I put on my black bodybriefer and padded it up, then some knee high stockings, my gray pants, and a tunic top that tied at the waist with a bow, giving me a very girlish look. I put on some comfy flats and went downstairs to find Caroline in the kitchen. She was dressed in the same outfit she’d worn Christmas eve, which made her look very classy and feminine. “Hi baby,” I greeted her.
“Good morning, girlfriend.”
“It’s easier for you – I’m always your girlfriend.”
Caroline fixed French toast, which was delicious. We sat there contentedly, sipping our coffee, making small talk until Caroline said, “You know, I wonder if I’d have started dressing if I hadn’t gotten infected.”
“Haven’t you always been a crossdresser?”
“Not really. I mean, I did it one Halloween, which was a hoot, and once in college for some fraternity ritual, but most of my gay flings were strictly butch. It wasn’t till after I flunked my H.I.V. test that I bought my first dress. Of course, I was really fucked up then, between my hysterical wife and the fear that I was going to die, and I think getting all those clothes was some kind of release for me.”
“Do you know how you caught H.I.V.? I mean, do you know who gave it to you?”
“Oh yes. It was a lovely one night stand with a guy who lied to me and disappeared.”
“How did you meet him?”
“Craigslist.”
“Wow. After all that, to think you went back and found me….”
“It’s addictive. To tell you the truth, I was really looking for the guy who fucked me, to see if he was still a menace out there, but then I found you, and your picture was so cute, and the way you described yourself as a hot cougar really turned me on.”
“Yeah, that was my blue dress. It’s a petite, which I normally can’t wear, but for some reason that one fit me, although it’s a little short. You’ll see when we go shopping today. You may have to try on a dozen dresses to find one that fits just right.”
“I’d love to see you in that dress sometime. Although I’ll be honest, it was that picture you emailed me, of you in that white nightie and stockings, that really nailed me to the wall.”
“Oh dear, I didn’t pack that one this trip! Although something tells me I’ll be back….”
* * *
After breakfast, I put on my trench coat – it was no weather for my new sable – and we were off.
Caroline was a nervous wreck after she parked her BMW at the garage for Water Tower Place. “Do I look all right?” she asked.
“You look great. C’mon, the first steps are the hardest. I’ll be your wingwoman. Now let’s go!”
She looked like she was a wanted criminal as we walked towards the entrance. “Caroline, listen to me: you’ve got to look like you belong here! Stand up straight, that’s better, now stop staring at your feet, and smile! Follow me.”
I hadn’t been clocked as a guy in years, but one of the downsides to going out with other crossdressers is the lowest common denominator rule: the girl who is least passable defines the group. I noticed that several people gave us odd glances as we walked along, but with some prodding and encouragement, Caroline began to act more like a woman, and by the time we got to Macy’s she was looking a little better.
She followed me into the missy department. Although she was marginally a woman’s size, the missy styles are much cuter, and I figured she could wear a size 18 dress, and because a man doesn’t have a woman’s hips, she could probably get away with pants and skirts in size 14.
She stayed close by as I rummaged through the racks of pants, selecting four or five pair that I thought might work for her. Then it was off to the fitting rooms – she panicked momentarily, but once she realized that it was unguarded, she followed me in and I found an open changing booth. “Here, try these on and let me know if any of them look cute. I’ll be right outside.” She had a strained look on her face as I closed the door.
Many minutes passed, and it was a little awkward for me to be standing there alone, but I suppose I looked like a mother waiting for her daughter to try things on. Eventually Caroline tentatively emerged, in a darling pair of khaki pants that hugged her butt and swirled around her ankles. “They’re perfect!” I gushed, and she closed the door again to change back into her skirt.
When she was done, she came out with her arms full of all the pants she’d tried on. “Leave the rejects in the fitting room,” I told her, and I had to take them out of her hands and hang them up on a rack before she followed me back into the store towards a cashier. There was a long line, and we waited patiently until a register was open.
I could tell that Caroline was paralyzed with fear, so I took her pants and paid for them. “Merry Christmas,” I said as I handed the shopping bag to her.
“Let’s leave now. Please!” Caroline implored me, and I didn’t feel like fighting her, so we hastened back to the garage and into her car. When she got behind the wheel, I could tell that she was a nervous wreck.
“Would you like to go someplace for lunch?” I asked, already knowing the answer.
“I’m sorry, Missy, but I’m a little freaked out.”
“No worries, baby. Actually, I’m kind of glad. I mean, I like you as a girl, but I love you as a guy.”
* * *
That evening, Ron asked me if I wanted to go out to dinner at Morton’s again. I could hardly contain my excitement! I’d packed the dress I wore the night Gregg tried to murder me, and my garter belt, stockings and stilettos, and I wore my brunette wig this time. It was still spitting rain outside, and I couldn’t bear to expose my new sable coat to that, so although I’d be cold I decided to go with my trusty pashmina shawl.
We got to the restaurant at a few minutes before seven. Ron dropped me off at the curb, and waited for a valet while I ran inside. I was waiting for him in the lobby when a stranger came up to me. No, it wasn’t a stranger - it was one of the cops who’s interrogated me at the Intercontinental the night I killed Gregg! I froze as he pulled something out of his coat pocket. “Mr. Xxxxxxx? I have a warrant for your arrest.”