The Craigslist Killer Pt. 03

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.

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."