The Craigslist Killer

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

The same maître d greeted me, and I held up two fingers this time. "Are you expecting someone?" he asked.

"Yes," I smiled.

"Would you like to be seated now?"

"Yes, thanks." He escorted me to a small table in the middle of the room, and I glanced over at the romantic booths along the wall. "Would you prefer a booth?" he asked without missing a beat. When I nodded, he led me over to one, and I sat down where I'd be able to see Ron when he came in.

At first, I thought nothing of the fact that Ron was running late. After all, he might be having trouble finding a place to park, or he might have gotten delayed at work. I declined a waiter's offer to get me something to drink, and sat contentedly in my little booth as the restaurant slowly filled up with businessmen and women, including the occasional loner like myself. I was terribly overdressed to be a woman dining alone, and I did catch a few glances from some of the other diners as they must have wondered about me.

Seven ten, seven fifteen...where was he? I took my cellphone out of my purse, but there were no calls or texts from Ron. The reality finally began to set in as I sat there stewing: another Craigslist wannabe! What a fool I'd been! The too-perfect response to my post, with an obviously bogus photo of a handsome man...the witty email exchanges...our phone chat, which had quickly devolved into phone sex...our texts last night, with me sitting here in a dress, and him getting off again...what a fool I'd been! Ron was probably a nerdy teenager living at home with his parents, or maybe he was a 300 pound goon who got off looking at pictures of tgirls...what a fool I'd been!

I was too embarrassed and depressed to face the prospect of dining alone as a woman again. Summoning as much dignity as I could possess, I got out of my booth, mumbled an apology to the sympathetic maître d, and tottered sadly back to my room. "Fuck!" I swore out loud in my real voice as I kicked off my heels and collapsed onto the bed. "Fuck this fucked up life!" I was starving after skipping lunch to keep my girlish figure, I was depressed and horny after being stood up, and I was furious at myself for falling for Ron's idiotic games. Morosely, I fired up my notebook computer to see if there were any business emails I needed to deal with, then as an afterthought I switched to Missy's address, where I found this response to my Craigslist personal:

Hi, just came across your post. It looks very interesting. Are you still in Chicago? Are you going to be here for more than this week? I have to fly out on Thursday and will be gone for a week. Would like to see if we can work out a meeting tonight?? I'll send info if it looks like we may be able to work something out. Gregg

How long had Gregg's response been sitting there? There was no picture attached, but he did say he'd send more info if I responded...I suppose it was because I was at my most vulnerable after just getting dumped, but I broke my cardinal rule and sent him this:

Hi Gregg,

Just got your response! Alas, I'm only here this week...send me a picture

and tell me about yourself,

Missy

That's that, I said to myself. Probably another loser like Ron. I was debating about ordering something from room service when I got Gregg's reply:

Hi Missy, would love to chat with you :)  you look lovely in your dress and I must say you have lovely legs as well.

Do you have IM if so we can chat in real time and see if we can hook up

Oh I do not do drugs, smoke or drink to excess but social drink is always fine

Hope to hear from you soon

Gregg

Hmmm....an Eagle Scout, but still no picture! I glanced at my watch. It was only 8:00. I was trying to decide whether to nag him for a picture again when my instant messenger pinged:

Hey Missy

Hi Gregg

Are you still in town?

Yep

How about dinner tonight?

It's kinda late

Have you already eaten?

Nope

Come on, my treat

You never sent me your picture

That's a problem

What's the problem?

I'm very well known and I won't send it out over the Internet

Well known?

I'm on TV

Like a newsman?

Yes

Wow, that's cool

I just got off work and I'm starving

Me too but I never date a guy without a picture first

Let's meet for a drink and if you don't like what you see, no harm no foul

I'm not leaving my hotel

I'll meet you there

What if I find you irresistible?

We can always skip dinner

No way Mister! What kind of girl do you think I am?

Where are you right now?

The Intercontinental

I can be there in ten minutes

At the bar off the lobby?

Yes, on my way

I tried to respond, but he was already gone. Now I'd done it! Broken my cardinal rule! Although after getting scammed by Ron, an emailed picture didn't seem like quite such a sure thing. What could go wrong? We'd meet at the bar, and if I didn't like the looks of him, I could blow him off. It was a public place, totally safe for a girl. And the upside was, if he was on TV, he was probably gorgeous! And I was awfully hungry...and horny...before I could stop myself, I was back in my heels and headed out the door.

I emerged from the elevator and made a quick stop in the ladies room to freshen my lipstick and tweak my wig. Didn't want to get there before him - a single woman alone in a hotel bar might attract unwanted scrutiny. When I'd fussed with myself long enough, I made my way slowly down the marble corridor, clickety clacking in my stilettos, trying to suppress a surge of excitement. Half an hour ago, I'd been a lonely wallflower, and now I was about to meet a mysterious stranger, looking hotter than hell in my new dress. A Chicago celebrity, no less! There he was, standing alone at a corner of the bar, handsome as hell in his blue blazer and repp tie. He looked up and cocked an eyebrow as I approached him.

"You must be Missy."

"And you must be Gregg."

He took my arm and led me to a bistro table by the window. I had to hop up into my tall chair, and I could tell that he was staring at my legs as I tugged my dress down towards my knees and crossed them. "Do I pass inspection?" I whispered.

"Oh yeah. One hundred percent. It's hard to believe."

"Well, I've had a lot of practice," I said in my girlish voice, which was working for me tonight.

"How long have you been doing this?"

"You mean meeting handsome strangers in hotel bars?"

"No! I mean dressing up as a girl."

It was always magic for me, talking to a guy on a date, confiding my innermost secrets to the only person in the room who had a clue that I wasn't the pretty woman I appeared to be. "Since I was twelve," I told him truthfully.

"Wow. Are you going to go all the way with this?"

He was easy to look at, and easy to talk to, and I found myself opening up to him. "I don't think so. I mean, don't think I haven't thought about it, a lot, but I kind of dig my other life too. The one that pays the bills."

A waiter appeared, and Gregg asked me what I'd like to drink. "A Cosmo, please," I said demurely, and after Gregg ordered a Manhattan for himself, the courtship continued.

"What do your friends and family think?"

"They haven't a clue."

"You're kidding, right?"

"Nope. I lead a double life. Should have been a secret agent."

"Man, I'll say. How do you manage that?"

"It's not easy! I'm lucky that I travel a lot, and I'm only Missy when I'm on the road these days."

"What do you do in your real life?"

"I work for a big company. Hey, I'm doing all the talking! Tell me about you."

"In a minute. I find you fascinating. Do you only make it with guys?"

"No! I like women too."

"Are you married?"

"I'm divorced," I told him truthfully.

"Really! What did your wife think about this?"

"What do you think?"

"I don't know. Some women might kind of like it."

"Well, not her. It was really my fault. I never told her, and I'm sure she thought I was cheating on her, which I was, only not the way she thought."

"I don't get it."

"It's hard to explain," I sighed. "I dressed up off and on all through high school and college, which I managed to keep a deep, dark secret from everyone. Then, when I got married, I went cold turkey for a while, but..." The waiter returned with our drinks, and I waited until we were alone again. "I just couldn't stop," I told him. "Cheers."

He clinked his glass against mine. "Cheers. Thanks for telling me all that."

I sipped my Cosmo, which went straight to my head, thanks to my empty stomach. "How about you? Have you ever made it with a girl like me?"

"Yes," he confided.

"Have you ever tried it yourself? Dressing up, I mean?"

"No," he answered nervously and a little too quickly.

"Are you gay?"

"Hardly! But for some reason, transgendered girls really turn me on. Like right now," he added.

I felt the familiar tingling in my panties. "Well, what are we going to do about that?" I asked after I drained my Cosmo.

Gregg took a twenty out of his wallet, placed it on the table, and stood up. "We are going to your room, where I'm going to make love to you right now."

I got unsteadily to my feet. "But you haven't fed me yet."

"We'll have room service afterwards."

I loved it when a man took charge. I loved being the passive one on a date. I loved being the girl. "Yes, sir," I said, hooking my arm into his. When we got to the elevator, we had the cab to ourselves, and after I pushed the button for my floor, I put my arms around his neck and kissed him. He kissed me back, a sweet, tender kiss that lasted until we came to a stop and the doors opened.

He wrapped his arm around my shoulder as we walked to my room. I took my key out of my purse and opened the door. The light in the room was still on, and I was about to kick off my heels when the light went out. Then I felt Gregg's hand over my mouth. Another hand grasped me savagely around my breasts, tearing my dress. "Don't scream. Don't say a word or I'll break your neck," he said in a menacing voice. "Tell me the combination to your safe."

My mind raced. Gregg was the maniac who killed the tgirl at the Sheraton! And I'd let him into my room! Once he got into my safe, he might kill me...even if he just tied me up and left me, I'd be exposed as a transvestite when the police found me. I flailed my arms around wildly, and Gregg loosened his grip for a moment when I kicked him in the shin with a stiletto, then he twisted my head back and I couldn't breathe. I was going to black out! My fingers brushed against the nightstand, and I felt the scissors which I'd used a few hours earlier to cut the tags off my dress. Without thinking, I picked them up, turned them around, and plunged the open points into Gregg's side.

He grunted in surprise and loosened his grip again, just enough for me to spin free. In the dim light, I could see him reaching into his jacket, and the glint of a knife. Before he could react, I lunged forward and plunged the scissors into his neck, twisting them as I hurled him backwards onto the floor. I threw myself on top of him and was about to stab him again when I heard a terrible, gurgling sound, as he tried desperately to breathe through his severed windpipe. He thrashed around for a few seconds, his whole body shook for a moment, and then he was still.

I sat back panting for a long time. When I finally got up, I didn't have to turn on the light to know what had happened. Gregg was dead. I'd killed him. When the police found out, I would become an overnight sensation. That kind of publicity would ruin my career, and make me a national laughingstock.

I got up unsteadily in my heels and turned on the light. Gregg's body lay in a twisted heap, a wickedly sharp knife still in his hand, but to my surprise there was very little blood, and the room was otherwise undisturbed. I studied the wound below his hideously distorted face. Evidently I'd scored a clean shot directly through his trachea, and when I twisted the scissors I cut it clear across. He was as good as dead before he hit the floor.

I looked down at my torn dress and shredded stockings, which must have gotten ripped during the struggle. I couldn't process the fact that I had just killed a man, dressed like this. A man who was armed with a knife, who had committed a murder two days ago, and who was about to kill me. I picked up the phone to call the police, but after another look around the room, I put it back down and started to think.

Nobody had seen me enter my room with Gregg. There were witnesses who had seen a pretty woman with Gregg in the bar, but my room was registered to a man. If I could just get Gregg's body out of my room, and remove any traces of him, what could ever link him to me? Craigslist? Our IM's? I'd cross that bridge when I came to it...Missy's email address was untraceable to me, and if I got out of this, I'd get her a new one just to be sure.

I stood over Gregg's lifeless body and tried to lift him. He weighed a ton! Finally I was able to drag him beside the bed so I wouldn't have to look at him, then I went into the bathroom to rinse the blood off my scissors. The pretty girl looking back at me in the mirror was bedraggled, but she didn't look like a murderess. It was almost as if nothing had happened to her. Coolly, she freshened her lipstick, brushed and fluffed her hairdo, and strode back to the murder scene.

A pang in my stomach gave me an idea. There was no way I could carry Gregg out of my room, but I might be able to wheel him out....after checking to make sure that his body was hidden beside the bed, I picked up the phone and asked for room service. After I ordered beef stroganoff and a bottle of red wine, I got down on my hands and knees and carefully studied the floor. There were a few drops of blood, but they were almost invisible against the burgundy carpet, and I would take care of them later.

Gregg's knife was a bigger problem. It was undoubtedly the same knife he'd used at the Sheraton. I decided to put it back in his jacket pocket. Once the police found him, they might be able to use it to trace him to the Sheraton murder, which would draw their attention away from what happened here. I carefully wiped off my fingerprints first. I also wiped down the light switch that Gregg had touched.

There was a tap on the door. Room service! I went into the bathroom and in my male voice called out, "Come on in!" I heard the door open. "Please just leave it by the door, I'll take care of your tip at reception."

"Would you like me to set it up and open your wine, sir?"

"No thanks, just leave it please." After I was sure the waiter was gone, I went to work: first, I removed the food, wine, cutlery and tablecloth from the room service cart. Next, I dragged Gregg's body across the floor, lifted him up and leaned him against the cart. With a supreme effort, I was finally able to get him sprawled across the top.

Now for the risky part. It would all depend on luck. As an afterthought, I kicked off my stilettos to give me more speed. Then, with my room key in my hand, I cautiously opened the door and looked up and down the hall. Not a soul to be seen. With a silent prayer, I pulled the room service cart into the hall and began pushing it as fast as it would go, in the opposite direction from the elevator. It swerved wildly under Gregg's weight, but I was able to keep it moving all the way to the end of the hall. Every second counted: if anyone were to see me trying to dispose of a body, I'd be in far worse trouble than if I'd just notified the police that I'd killed a man in self-defense.

There was a service closet at the end of the hall. I tried the door, but it was locked. So I would just have to dump him here. I rolled Gregg off the cart, and immediately started pushing it back towards my room. I was almost there when I heard the ding of an approaching elevator! Quickly, I unlocked my door, shoved the cart inside and pulled the door shut behind me.

It was only a matter of time before the body was discovered. Although this must sound callous, I was ravenously hungry, and I busied myself resetting the room service cart and opening the bottle of wine. I ate and drank slowly, savoring for the first time my survival from almost certain death. With any luck, when the body was discovered, there would be nothing to connect it to me, to this room. Which reminded me: I took my glass over to the blood spots on the carpet and poured red wine over them. It all blended into a typical room service mess.

Suddenly I heard a commotion in the hall. There was a scream, and somebody shouted. After a few minutes, there were more footsteps, and a muffled conversation. Then a longer delay before the police arrived, their walkie-talkies giving them away. All the while, I huddled behind my locked door, an unwilling witness to the drama taking place. I could hear doors opening and other guests asking questions, and the police and hotel staff instructing them to return to their rooms. Perfect!

Now it has gone quiet. In a few minutes, I'm going to take off this dress, stash all of my female paraphernalia in my suitcase, and collapse into bed. If the police come back, I'll be the clueless man they expect. Maybe I'll check into a different hotel tomorrow. Wait, my chickphone is ringing! I fished it out of my purse.

"Hello?"

"Missy, it's Ron." I was about to take his head off when he said, "I'm so sorry about tonight! My ex called me while I was on my way to tell me that our son was in the emergency room."

"I don't believe you."

"Look, I don't blame you! There was no way I could call you. By the time I got to the hospital, he was already in surgery."

"Is he okay?"

"Yes, thank God. He broke his leg during football practice, and they had to put him under to set it, but he's going to be fine."

"Oh, I'm glad. I was really pissed, Ron."

"Like I said, I don't blame you. I only hope you'll give me a chance to make it up to you. How about dinner tomorrow night?"

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
RebeccaCherieRebeccaCherieover 9 years ago
Wow.

Different, exciting. I sometimes imagine a man grabbing me like that while I am dressed !!!! Your story was thrilling.

Xxxxx

Rebecca

HeisenhugHeisenhugover 9 years ago

Not what I'd normally call erotica, but still worth the read

AnonymousAnonymousover 9 years ago

not bad at all something with a twist i give it 5 stars

AnonymousAnonymousover 9 years ago
Great read!

Not my usual type of story, but very well written and exciting.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Southern Hospitality Milfy seductress does all she can to score the boy next door.in Transgender & Crossdressers
My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
Big Tranny, Little Bed Sharing a bed brings two friends together.in Transgender & Crossdressers
Bitch Maker Ch. 01 Kinky shemale finds a man to be her maid.in Transgender & Crossdressers
A Debt to be Paid Chris comes up short on the rent.in Transgender & Crossdressers
More Stories