The Craigslist Killer Pt. 04

Story Info
Confession is Good for the Soul, and the Sex is Great Too.
3.7k words
4.8
7.8k
4

Part 5 of the 5 part series

Updated 09/22/2022
Created 11/02/2014
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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

© 2014 by Thrillerauthor

*

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."

Ron never dressed up as Caroline again.

* * *

A cold front came through after the storm, and the weather had turned bitterly cold. Ron insisted that I wear my sable fur to Dexter Boyd's office, and I was hardly going to argue with him. I might never get to wear it again! I also snatched one of Caroline's Gucci purses, and I must say I made quite a sight as I emerged from Ron's BMW and entered the lobby of a skyscraper on LaSalle Street. Ron drove off -- he told me to call him when I was finished -- and I ignored the stares of some envious women as I rode up in a crowded elevator. The doors opened into the smartly furnished lobby of an exclusive law firm, and after presenting myself to the receptionist, I spotted a copy of the Tribune and sat down in a cushy chair to read it. There I was, on page one, above the fold:

SUSPECT IN HOTEL KILLING ARRESTED

Chicago -- Police arrested a Los Angeles man last night in connection with the November slaying of Greggory Alford at the Intercontinental Hotel. Xxxxx Xxxxxxxx, 32, had just entered an uptown restaurant, dressed as a woman, when he was taken into custody. According to sources within the Chicago Police Department, Xxxxxx was confronted by detectives after Alford was found dead in a hallway near Xxxxxxx's hotel room, but he was dressed as a male and denied any involvement. Subsequent evidence linked Xxxxxx to the killing of Alford, who is believed to have been involved in a number of assaults and burglaries involving transgendered women at Chicago hotels.

A woman approached me, and asked me to follow her. She led me to a small conference room, and offered to take my fur. I was a bit uncomfortable, watching her take it away, until Dexter Boyd greeted me and asked me to sit down. He studied me carefully, then went to work. "Sorry to keep you waiting. I was on the phone with the District Attorney. He's not very happy with me."

"Were you talking about my case?"

"Of course. By the way, how shall I address you?"

"I beg your pardon?"

"According to the police, your name is Xxxxx Xxxxxxx. The reason I asked you to dress as a woman today is that Mr. Xxxxxx is somewhat notorious in Chicago at the moment. But you make an uncommonly attractive woman, and as a blonde, you look nothing like your booking photos. It's obvious to me now that if you stay as you are, you'll have no trouble living a normal life until this matter has been resolved."

"I guess that depends on what you describe as a normal life."

"Point taken. I've represented two transgendered clients over the years. One is a professional athlete from California, who is married to a famous actress. The other was a troubled young man who just graduated from Northwestern as a beautiful young woman. It seems to me that society is redefining normal, every day. So let me ask it another way: who do you want to be?"

"This is the me I want to be," I told him firmly. "Please call me Missy."

"Excellent. Now that the world knows your secret, you don't have to try to hide it anymore. My guess is that's why you lied to the police in the first place?" he asked. I nodded yes. "Now, tell me everything that went down between you and the police. Please leave nothing out." I closed my eyes and played back my nightmare to him. He raised an eyebrow when I told him about the altercations in the holding cell. "Now I know what the D.A. was talking about," he said.

"What do you mean?"

"First, he chewed me out for tricking them into setting a bail that you could easily pay. He still has no idea who was behind it -- I had Ron get a cashiers check through my law firm -- and he never will. Then he launched into me about the beat down you gave some punks at the jail. He wondered how in the name of God you put two of them in the hospital? It proves how dangerous you are, he told me. To which I replied that he just made my case for the defense: any man, even one wearing a dress and high heels, will defend himself if he's attacked."

"When do I have to go back to jail?" I asked him.

"Never. The DA knows that the cops made a mistake by arresting you the way they did, and throwing you into that cell. He says they were really pissed off that you lied to them, and they want to know what happened that night. But they're prepared to reduce the charge against you to involuntary manslaughter, and recommend no jail time, if you give them a complete statement."

"Involuntary manslaughter?"

"That's a felony, and I told the DA that was unacceptable. After some hemming and hawing, he agreed to take it down to a misdemeanor, obstruction of justice. I told him I'd have to talk to my client."

"So you got me off?"

"If you take it. We could go to trial if you want -- imagine what a spectacle that would be -- and I'm sure I could beat the murder charge, but you never know."

"I'll take it."

* * *

Dexter Boyd was some kind of magician. He quietly arranged for my hearing date to be moved up to December 31st, and in an empty courtroom I pled guilty to one count of obstruction of justice. We had carefully crafted a written confession in his office, and there were no reporters present when I was sentenced to five years' probation.

When we got back to the townhouse, Ron assumed that I'd be too shattered to go out, but I surprised him when he asked me what I wanted for dinner. "I'm going take off these scratchy guy clothes, have a nice hot bath and put on something pretty. Then I'm going to treat you to a night on the town. I want to be a girl again! It's New Year's Eve!"

As I soaked in sea of bubbles, I thought back over all that had happened to me over the past two months. My business career was over -- I'd quit over the phone before they had a chance to fire me, and Ron had arranged for all my worldly possessions to be packed up and shipped to Chicago. Most of them would be joining Caroline's trousseau at Goodwill: for better or worse, I was beginning a new life as a wealthy woman, with a man I had fallen deeply in love with.

I took my time getting dressed that night, savoring every sensation as I transformed myself from man to woman for the last time. From now on, I'd be Missy every minute of every day and night, until Ron got tired of me and threw me out! Well, there's no way that's gonna happen, I said to myself as I admired the finished product in the full length mirror on the back of The Closet door: in my red pencil skirt, silky black top and sheer black nylons, I was mistletoe material, and as soon as I was in Ron's arms, my bright red lipstick needed replacing....

I snuggled in my sable on the way to Morton's. Ron laughed off my offer to pick up the tab, and over a long, lovely dinner we talked about all we'd been through together, and all that lay ahead. We sat side-by-side at a romantic booth, and when his hand strayed to my knee between courses, I slid it all the way up my skirt, and felt for him under the tablecloth. He was stiff as a board.

That night, Ron undressed me once again, then I excused myself and surprised him in my white babydoll nightie and stockings. They'd won his heart the day we met on Craigslist, and they won his heart again that night. This time he took the lead, teasing and pleasing me throughout the night, and after each delightful orgasm I went to work on him, sucking and fucking him with wifely abandon. We almost ran out of condoms, and the batteries on our dildos were dead by morning.

At one point, we heard cheering and horns blaring outside as the clock struck midnight, but we were too busy making our own fireworks to care.

EPILOGUE

Ron and I had twelve glorious years together. Although we never married, for all intents and purposes we were man and wife, and we did everything together: season tickets to the opera, Cubs games every summer, all of the wonderful festivals that Chicago is famous for, and of course dinner at Morton's every Saturday night when we were in town. We traveled around the world together, several times (I managed to get a photo ID as Mrs. Right) and I even met Ron's son, which was awkward at first, but became very precious near the end. When the disease finally caught up with him, Ron was very brave, and incredibly considerate towards everyone who cared for him. It took a terrible toll in its final stages, and I don't know how I managed, but I insisted on setting up hospice care for him at the townhouse, and I was with him, holding his hand, when he died.

Ron was a very generous person. Dozens of charities were the recipients of large bequests, and of course his son was extremely well taken care of. Although he had settled with his ex-wife years ago, she was also a substantial beneficiary in his will. Ron left the rest -- half a billion dollars -- to me. I'm still living in the townhouse -- the memories are good here, and I've come to love Chicago. I haven't worn a stitch of male clothing since the day I got sentenced, a lifetime ago. Whether I'll actually transition, or simply stay the way I am, I'll always be a woman, and thanks to Ron, I'll never have to worry about the discrimination and hardships that plague so many of my sisters. Dexter Boyd was right: once my secret life was out to the world, I had no alternative but to own it, and over time I've become a minor celebrity in Chicago society. I go to work every day, immaculately dressed, at a foundation I've set up in Ron's name to provide financial assistance to transgendered women in crisis. It will be his lasting legacy.

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

Well done. It was great way to wrap up the story. Thanks for your work

Share this Story

READ MORE OF THIS SERIES

Similar Stories

T-Girl Disco Hoe T-Girl leaves work as a man and ends up with a man inside.in Transgender & Crossdressers
Dolled Up To Rock 'n' Roll CD gets slutted up for a concert and has some adventures.in Transgender & Crossdressers
The Deviants' Room Four stock-brokers hire a crossdresser for the weekend.in Transgender & Crossdressers
One of the Girls Eric unwittingly takes a job as a shemale porn actor.in Transgender & Crossdressers
Good Little Bitch Pt. 01 College Halloween party dress-up opens new doors.in Transgender & Crossdressers
More Stories