Yours Truly, Jackie Dollar 25-01

Yours Truly, Jackie Dollar: The Dillon Matter

by Amanda Sadie Moss

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*Single Ladies rings out*

"Huh, damn, huh? Ah fuck. Jackie Dollar."

"Jackie. It's Mallory Fuchs. Litchfield Casualty. I need you pronto."

"Damn it Mal, I was literally having a very horny dream. I was riding black cock until dawn. What the hell do you need to interrupt me for?"

"I'm sorry my pussy's not good enough, Jackie, but I need you here now. I have a very upset client who holds a large policy on his life and on his 1934 Studebaker Dictator. Supposedly Cary Grant owned this car at one point."

"He's panicked over a 1934 Studebaker? Why do you need me for that? How much is the policy?"

"$250,000, just on the car."

"$250?! The car's not worth that much!"

"Can you get here, Jackie? Please bring some pants." *click*

"Alright, Mal, alright. Fuck."

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Tonight, the transcribed adventures of the femboy with the action packed expense account. America's fabulous freelance insurance investigator......

"Yours Truly, Jackie Dollar."

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Expense account submitted by special investigator Jackie Dollar to the home office of Litchfield Casaulty, Hartford, Connecticut. The following is an account of my expenditures during my investigation of the Dillon matter.

Expense account item 1, $25. Gasoline for my jalopy.

I really didn't want to leave my Irvington, New Jersey bed. I just finished a tough case of someone burning down a brand new school in rural West Virginia to collect an insurance paycheck. That paycheck would've paid his gambling debts. My grandfather dealt with the same in rural Colorado back in the 1950s. Except in that case, there were no gamblers, just three public figures who were massively corrupt. Apparently society hasn't changed that much in the last seventy years, but the outbreak of sports gambling. Jackson Harrison literally was like $4,000,000 in debt from bad sports betting. But that case took a lot out of me, and I spent the last 3 days in bed making up for it. Now Mallory wants me for a new case. She better be paying.

Mallory Fuchs is another descendant of one of my grandfather's colleagues. Her great-uncle, Hillary Fuchs, was once a respected insurance agent. Unfortuntely he went off the deep end and became a criminal before my grandfather had to shoot him. That one hit my grandfather pretty hard. Mallory never met her grand-uncle but knew the stories. Her reference to me and her pussy isn't unusual, considering she and I have had sex on occasion. I'm admittedly a very horny investigator. The last time I saw Mallory, she was in a sequin dress and I was in my sexy bitch outfit. I'm a femboy, not anywhere as masculine as my grandfather Johnny, so I can be a woman or a man depending on the situation. Anyway, I jumped in my car, got gas and raced over to Hartford.

Around 2pm I walked into Mallory Fuchs office. She was barefoot, wearing a light blouse and a kneecap skirt. It was hot in Hartford today and her outfit reflected it. She always put a lot into being sexy. I sat in her leather office chair while she discussed the case with me.

"Mal, you made me drive here over a 1934 Studebaker. There better be a damn good reason and a damn good expense account for it."

"I didn't want to Jackie, but Matthew Remington Dillon wants to talk with you about this. He said someone's been threatening his life over his car. I don't know who, all I know is that someone apparently takes a Studebaker super seriously."

"Apparently. Someone is a bit of a nut. So, you didn't answer this on the phone. Who the hell gave him a $250,000 policy on a car not worth that much money?"

"Our agent in Brooklyn, Mark Quentin. Supposedly the Studebaker was owned by Cary Grant and his improvements to the car make it worth far more than the JD Power value of the car."

"So, is Mr. Dillon coming here or do I need to waste gas going to Brooklyn first?"

"You'll be going there. Mr. Dillon refuses to leave Mark's office until he sees you. Mark's currently very aggravated."

"There better be a good expense account for this. It feels like an utter waste of time over a fanboi of a Studebaker."

"Just do it, Jackie. If necessary, I'll quadruple your expenses. There's the door."

"Fine."

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Expense account item no. 2, $11.19, tolls over the Bronx--Whitestone Bridge.

I jumped back in my car and raced down Interstates 91 and 95 into the Bronx. I jumped on the Bronx--Whitestone Bridge and entered New York City. Eventually, I worked my way down into Brooklyn and found the office of Mark Quentin. Parking six blocks away because it's Brooklyn, I eventually wandered into his office on Avenue U. His secretary showed me into a back office where a gray-haired man with glasses and a thick tuxedo sat in an office chair. Across from him was Mark, who was holding a shot of brandy in his hand. Mark was in his mid-50s, he had a good business suit on and wore a carnation. I am supposed to be here to solve a case and I walked into a party (if only that was true).

Mark got up from his desk and shook my hand. "You must be Jackie Dollar."

"I am. A very tired one, but I've been promised good expenses."

"Well, this is Matthew Remington Dillon. He's mad as hell and utterly refuses to leave my office until I make him comfortable, and I don't mean sexually."

Dillon looked at me with this look on his face like he was skeptical. "This is your best investigator? He looks like a fag."

"We don't hired based on looks and sexuality, Mr. Dillon. We hire based on quality of service and Mr. Dollar is our best investigator. It runs in his family."

"Oh, this is Johnny's grandson? Well, what a failure on his part."

I stepped in. "Look Mr. Dillon, I can walk out of this door right now and still get my gas and tolls quadrupled. Either shut it or tell me why the hell you want me here. You're not exactly Mr. Olympia yourself."

Dillon gave me a very dirty look that said "I hate your faggot ass and I hope you die." That said, he swallowed his saliva and started to explain the problem.

"I own a 1934 Studebaker Dictator. From what I was told when I purchased it, the actor Cary Grant owned it when it was new. I loved Cary Grant's films and I immediately wanted it. You see, Mr. Dollar, I own a chain of fast food restaurants through Nassau and Suffolk Counties, despite being a native of Brooklyn. I was born into money and I don't lack for it. There's only thing that matters in my life: me. Apparently, someone thinks a lot of me too, and not in a good way. I've gotten threatening letters and voicemails the last few weeks about someone wanting my Studebaker and me out of the way."

"Did you call the police?"

"Yes, but the sargeant in charge, Faraday, wanted no part of it, saying I had no evidence that my life was in legitimate danger. I told him where he could shove his illegimate danger and stormed out of the office. I then called Mr. Quentin demanding his best investigator. I want my car and my life protected. $2.5 million lies on it."

"$2.5 million? You have a $2.25 million life insurance policy?"

"Yes. I said, I want the best for myself and only myself. To hell with anyone else. I'm worth far more, I consider it a pittance in comparison. You gonna help me or not, fag?"

"If you keep calling me that, no. I don't like you, but I don't want you dead. You clearly don't care about me, but part of my job is caring about your safety and finding this person. Once that's done, I don't give a damn. Now quit it with the discrimination or I'll just walk out of this office."

Dillon got up from his chair. "You don't have to. I'm leaving. My address is on Dune Road in Westhampton Beach. I better see you before midnight."

Dillon slammed the door shut behind him. I turned back to Mark.

"What a guy. Quite a douchebag. What were you thinking working with him?"

"His money, Jackie. I'm gonna go smoke a cigarette."

That he did. I took my leave and got back in my car. I got on the Sunrise Highway and worked my way to Center Moriches. There I had an early dinner before getting on the road back to Westhapton Beach. I found his house, a 5br mansion on the waterfront of the Atlantic Ocean. It looked like something he would live in, with a heliport in the backyard with tennis courts. I saw a 1934 Studebaker in the front of the house. I noticed something else.

It was on fire.

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There will be another story in our series, the Dillon Matter, next month. Next month, the prized car on fire and the real prize was inside. But who would want this prize? Join us, won't you?

Yours truly,

Jackie Dollar ;)

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So, Jackie Dollar is back. Just like from May–September 2024, we are gonna have a 5-part series of the femboy with the action packed expense account. I get that the target audience is definitely on the older side, but I was glad that some people thought the world of it. I certainly enjoyed writing it. Unlike The Genovese Matter, there's gonna be some serious sex scenes as this is gonna get pretty wild. I apologize in advance if the language gets a little rough as it did here. It's not gonna get better.

-- Amanda Sadie