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.