The Craigslist Killer Chronicles

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.