The Craigslist Killer Pt. 02

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."