The Craigslist Killer Chronicles

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."

* * *

That night was like something out of a horror movie - the most horrendous experience of my life, and that includes Gregg's attempt to murder me.

It began with the cops whisking me out of Morton's through the kitchen door, so I didn't even have a chance to tell Ron what was happening. I was worried sick about what he must be thinking when he entered the restaurant to find me gone, but that was swiftly replaced by genuine fear for myself when my hands were cuffed behind me. I was frog-marched into the back seat of a police car, and the cop who arrested me started to drone my rights: "You have the right to remain silent," I remember him saying, and I did.

Once he was finished, he started grilling me about the night of Gregg's murder. "You told us you spent the night in your room," he told me, "but that wasn't exactly true, was it? How long have you known Mr. Alford?" That totally threw me - how much did the police know? What did they suspect? "Leaving your lipstick on that wine glass wasn't very smart," he went on, trying to make me talk. I just sat there beside him in the back seat, staring straight ahead at the metal grate on the seatback.

"First degree murder," a cop in the front seat observed, "that's gonna get you life in prison if you don't cooperate. If you play ball with us, we'll do everything we can to help you."

"You shouldn't have lied to us that night," the cop beside me jumped in. "That makes you look guilty as hell." The classic good cop, bad cop routine, playing out in a real-life, terrible nightmare. I kept my mouth shut all the way to the police station, where I was escorted roughly out of the car, through the door and down a long, dark hall.

I honestly don't remember everything that happened to me that night, but some of it is seared in my memory. After I was lined up for my booking photo, one of the cops tore off my wig, and the pictures of me in tears with a man's made-up face were on the front page of every newspaper in Chicago the next morning. The worst was yet to come: after I was booked, I was taken down another long, dark hall to a holding cell, which was occupied by half a dozen enormous men who greeted me with evil eyes. I cowered in a corner, shaking in my little black dress and heels, as they sized me up.

"You hot, baby," one of them said as he approached me. "What you got under that dress?" He lifted the hem and smiled. "Whoo-ee, looka that, you got panties on too." I tugged down my dress and backed away from him. "Man, that's some high class hooker," he said to the group. "Me first."

He tried to reach under my dress again, and without thinking I kicked him as hard as I could in the testicles with the pointy toe of a stiletto. He roared in agony and fell to the floor as the other prisoners gathered around. "Fuck you, fairy," one of them screamed. He grabbed me by the shoulders and forced me back against the wall. I punched him as hard as I could in the nose, breaking it, and a torrent of blood ran down his face as he cursed at me.

I was squaring off against the next hoodlum when a guard came to the door and shouted at the men to back off. Evidently the powers-that-be decided that I was valuable property, because I was taken to a smaller cell, where I spent the rest of that night alone, in abject fear and misery.

* * *

Early the next morning, I was rousted out of my cell, and after a horrible breakfast which I couldn't touch, I was mercifully given an orange jumpsuit to put on. I scrubbed off as much of my makeup as possible, and waited for what seemed an eternity until a guard told me it was time for my arraignment and bail hearing. I assumed that some public defender would be representing me, and I looked sullenly around the crowded courtroom - the media had obviously been tipped off - until I saw Ron, sitting in the back row, giving me a quick thumbs up. A surge of hope rushed through me, although I was humiliated for him to see me that way.

A bored-looking judge eventually took the bench, and my case was the first one on the calendar. A very young woman stood up and identified herself as my attorney. She was with a law firm in Chicago, which puzzled me, until I got a wink from Ron. She stood beside me as I pled not guilty. Then a deputy district attorney gravely pronounced that I was charged with a capital offense, and added that I was a high flight risk since I'd fled to Los Angeles after the murder. He demanded that bail be set at a ridiculous ten million dollars.

My attorney said nothing. "So ordered," the judge said, and he set a date in February for motions to be filed. With that, I was taken back to my cell, in a complete state of shock. Ten million dollars! There was no way I was getting out of jail until my trial, which would be months away. Why didn't my attorney put up a fight? I assumed that Ron had retained her. Couldn't he have found someone who knew what she was doing?

Suddenly my cell door opened and a guard handed me a bag filled with my dress, heels and undies. "Get dressed," he sneered. "You made bail." Under his baleful eye, I took off my jumpsuit and tugged on my panties, dress and shoes, leaving my slip and stockings behind. My wig was nowhere to be found. Not quite believing what was happening, I was taken before some munchkin who "out-processed" me and handed me back my purse. My child lawyer was waiting for me, and she led me down yet another long, dark hall and out into an alley, where a limousine was idling.

Ron was sitting in the back seat next to an impeccably dressed black man. After I got in, my child attorney closed the door and we sped off. I was still in a state of shock, and the black man studied me with an appraising eye for some time before he spoke. "You probably have some questions about what just happened," he said at length.

"I'm just so glad to be out of there! Ron, I hope you didn't just put up ten million to spring me?"

"Missy, it's time you knew a few things about me. I told you I sold my business last month. What I didn't tell you was that it sold for over a billion dollars. Even after Uncle Sam gets through with me, there will be plenty enough left. So your bail today was nothing, really."

"But the D.A. didn't know that," the black man said. "If they'd known you had a friend like Ron, they'd have pressed the judge to hold you for no bail, and you'd have been in jail until your trial, which given the current backlog in Chicago, might have been over a year. And they didn't know that I was involved, because if they had, they would have smelled a rat. Which is why I sent our greenest associate to represent you."

"Who the hell are you?" I asked him.

"My name is Dexter Boyd," he chuckled.

"Only the most brilliant criminal defense attorney in Chicago," Ron broke in. "I called him last night once I discovered what happened to you."

"What happens now?" I asked.

"We're taking you back to Ron's home. Take a good shower and get some sleep. This afternoon, I want to meet with you in my office. As a woman."

* * *

Once we were back at the townhouse, and Dexter Boyd's limousine drove off, I collapsed into Ron's arms, sobbing uncontrollably. Ron gently guided me upstairs to the master bedroom and closed the door. I collapsed onto the king sized bed and immediately fell asleep.

Later, I took off my dress and indulged in a long, hot bath before I dressed for my appointment with Dexter Boyd. For some reason, he wanted to see me as Missy, and I went through the makeup routine by rote before I tried to figure out what to wear. Certainly not one of my prissy Christmissy outfits! I finally decided on the blue sweater and skirt I'd worn to fix Christmas dinner, with nude nylons and blue kitten heels I'd packed to wear with them.

My faithful wig was somewhere at the Cook County Jail, but Ron's blonde wig was available, and I was beginning to feel like myself again after I put it on. Ron smiled approvingly when I came downstairs, and he started to fix lunch in the kitchen while I took him through my experiences the night before, leaving nothing out. "My God," he said when I was through, "you're lucky you didn't get yourself killed in that cell."

"It was a horror, Ron. I'm sure they thought I was some kind of high-priced tranny hooker. And the booking! I was so ashamed to have to stand there, without my wig, in a dress, getting my picture taken by those goons." The Chicago Tribune lay open on the kitchen table. "Shit, what happens when that picture makes it to LA? I'm gonna get canned for sure."

"The law in California is good, Missy. They can't discriminate against you for crossdressing."

"Give me a break, Ron. I'm up for murder one! And you don't know my company - the Chairman is a right-wing nut. They'll figure out some way to cut me loose."

"So what?"

"What do you mean, so what?"

"Missy, in case you've forgotten, I've fallen head over heels in love with you. You don't have to worry about working, ever again."

"Ron, you don't have to say that. I'm not exactly a prize catch. Will you wait for me while I spend a lifetime behind bars?"

He embraced me, and I hugged him back, tears running down my cheeks. "What a pair we make! An H.I.V. case and a jailbird," I sniffled.

"Missy, Missy. You're not going to spend any more time in jail, not if Dexter Boyd has anything to say about it. He's the best, and you've never been in trouble before, have you?"

"No! That's what makes this all so bizarre. One minute you're a law-abiding citizen, and the next..." I started to cry again.

"I totally blame myself for what happened last night."

"What do you mean?"

"Dexter thinks the cops were hoping you'd return to Chicago so they could question you, and they must have been tipped off by the airline when you came back. Then they saw us yesterday at the mall, and got a warrant by the time we went out to dinner. When they saw you again in the same dress you wore that night, they moved in."

"I guess it was going to happen sooner or later, Ron. I'm so sorry I got you caught up in all this!"

"Don't worry about me, sweetheart. The cops never saw you with me, only Caroline."

"Poor Caroline!"

He laughed. "That shopping trip was a real eye-opener for me. I felt like a total fraud, and you were so natural, so confident out there...dressing up filled some need for me, at a very difficult time, until I met you. I'm much more turned on when I see you as a beautiful woman, knowing that you made yourself into her, just for me."