The Craigslist Killer Chronicles

"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."

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.

* * *

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.