The Private Transvestite Detective (or the Undercover Dick)

by

Caution: This Humor Sex Story contains strong sexual content, including Ma/Fa, Ma/Ma, NonConsensual, Coercion, TransGender, CrossDressing, Humor, Cheating, Cuckold, Oral Sex, Anal Sex, Leg Fetish, .

Desc: Humor Sex Story: A little transvestite humour; a story in the genre of The Maltese Falcon, only the heroine has a surprise under her skirt.

With apologies to the writers of the various movies from which I borrowed some inspiration (and a few good lines).

Chapter 1

It was late Friday afternoon and I sat behind my desk smoking a cigarette, leaning back in my chair with my high-heels resting on yesterday's newspaper. I contemplated my red-painted toenails through the gauzy nylon of my fully-fashioned stockings. They were overdue for a touch-up, and so was I.

The fading light feebly outlined the sign painted on the glass panel of my office door. It read: ycnegA evitceteD etavirP- snolyN elehciM.

A shadow darkened the glass panel and I leaned forward and filled a glass with scotch.

It was Darleen my part-time secretary and receptionist. Darleen was supporting a five-year-old kid and a forty-year-old husband who drank more than she made. She spent four hours a day, three days a week typing, filing and answering my phone. She also spent five minutes a day, three days a week on her knees under my desk. It was a good arrangement; she needed the cash and I needed the relief.

"You have a visitor; it's a Mrs Silvia Fellatrix," Darleen announced as she opened the door.

"Pretty?" I asked.

"Prettier than me, but then I'm easier." Darleen relied.

I knew that Mrs Fellatrix was trouble as soon as she walked into my office. She was all class; she was the type of woman who could give a guy a hard-on with a flick of her skirt.

She flicked her skirt and I adjusted myself under my desk as I sat up and took a swig of my drink.

"Take a load off?" I motioned to the chair in front of my desk.

"No thanks, I just had this dress dry-cleaned," she replied and nestled her scrumptious buttocks into the offered seat.

"Is that a gun in your skirt or are you just happy to see me?" she asked, nodding in the direction of my crotch.

"Well both actually," I answered, pulling the derringer from where I had it hidden away in my garter.

Mrs Fellatrix reached out and took a smoke from the packet on my desk. She looked me in the eyes and flashed me a brilliant smile.

"Shall we get down to business?" she purred.

"I thought you just had your dress dry-cleaned," I retorted.

"I'm a woman who likes a man dressed like woman to behave like a gentleman," she sighed.

"I need your help; my husband is missing and so is my most valued family heirloom. It's a statuette called the Golden Cockerel," she stated.

"The bastard waited for me to go away before he absconded with it. He's off somewhere with some tranny whore living the high life and kicking up her heels!" she finished.

"Hang on doll; I resemble that remark; let's get to the facts. You've been away?" I inquired.

"The Islands," she replied.

"Virgin or Caribbean?"

"Let's just say I'm back from the Caribbean," she smiled.

"And this Golden Cockerel is worth a lot of dough?" I asked.

"Yeah; and I'll compensate you generously if you return it to me," she added.

"What about your husband?" I asked.

"I'm not giving him any compensation; that'll have to come out of your end," she retorted.

"I mean what do you want me to do about him?"

This woman was either very smart and playing dumb, or very dumb and playing smart, or she could be very smart whilst pretending to be very dumb and playing smart.

"If he gets in the way; do what you have to," Mrs Fellatrix smirked, "I just want my Cock back!"

"Ok," I said, "I know what that's like. I'll take the case.

"But why out of all the transvestite detective agencies in all the towns in all the world did you have to walk into mine? I asked.

"Because yours is the only one," she answered.

"And as I said, my husband has proclivity for transvestites; so you should be able to find him easily enough."

It made sense to me now. While she was away her husband had stolen the Golden Cockerel and taken it on the lam with some low-life tranny.

"Tell me, who was it he left you for? Was this his first tranny, or were there others in between? Or aren't you the kind who tells?" I asked.

"There have been plenty before this one; all tarts and harlots the lot. But this time he's taken up with a real sleaze-bag; she's had more pricks in her than a second-hand dartboard!" she spat.

"Her names Lizzie Swallows and she works in bar down near the docks; the kind that gets full of seamen. That's the bar, not Lizzie," she clarified her statement.

"I don't think I know it," I drawled, drawing on my cigarette and taking another pull at my drink.

"That's funny," said Mrs Fellatrix, "that's where I found your business card; also your name is scratched into the back of the men's-room door along with your home and office phone numbers," she countered.

"Ok, ok, I might have been there once or twice for a quick swallow err drink." I stumbled.

"Anyway the Cock. I'll get right on it." I said.

"I would prefer if it you took care of my case before attending to your own pleasure," she smiled.

She threw a fist full of fifties and a black and white photograph of Lizzie Swallows on my desk and stood up and walked to the door. Her ass wiggled like two ferrets trying to get out of a sack.

"Call me when you find the Golden Cockerel; as for my husband, I don't care if I never see him again; if you know what I mean," she finished and closed the door behind her.


Chapter 2

I had been home to change. I decided that if Mr Fellatrix had a fondness for slutty trannies, I would pander to his desires so that hopefully I could get close enough to him to get my hands on the Cock.

Of course it was difficult for a classy girl like me to find the type of slutty clothing that might attract a man such as Mr Fellatrix but after spending thirty seconds surveying my wardrobe I picked out something that might work.

I was dressed in a red leather micro-miniskirt, sheer white blouse, cherry-red five-inch high-heels, black seamed stockings and a blonde wig. My makeup was heavier than a doctor's wallet on payday.

I looked up at the sign hanging over the sleazy bar: 'The Tented Skirt'. It was not the sort of place that you would ever find me in.

"Hi Michele," the bartender and the dozen or so sailors sitting at the bar sang out as I entered.

I sauntered up to the bar and looked around.

"You got time for a stiff one?" the bartender asked.

"No thanks, I'll just have a drink," I replied.

At the end of the bar a cheap transvestite hooker held a cocktail in one hand and a sailor's cock in the other.

"I'll have what she's having," I gestured to the bartender.

"I don't think she's finished with it," he replied sarcastically.

"The drink you idiot!" I corrected him.

"One 'dirty cock-sucking cowboy' coming up," he smiled.

"Ever since 'Brokeback Mountain' us girls have to fight off competition from the closet cowboy queens," I retorted.

"Save the comedy Michele, as a comedienne, you make a great detective," he rejoined.

I took my drink and wiggled my pert ass over to a booth. As I walked to the booth I could feel a pair of eyes glued to my ass. Removing the fake novelty eyes from the rear of my skirt I vowed to remind Darleen that her practical jokes needed to cease forthwith.

Sitting down I took out the picture of Lizzie Swallows and scanned the gloomy bar looking for any sign of her and Mr Fellatrix.

I saw her sitting in a booth across from where I was sitting. You could tell she was a cheap slut by the way she dressed; she wore a red micro-miniskirt and matching red high-heels. Who else but a floozy would wear an outfit like that to an establishment like this.

She was arguing with a guy who was sitting in the corner of the booth. As I watched them, she suddenly stood up, slapped him across the face and stormed out. I knew that I wouldn't get another chance like this so I sauntered over to where Mr Fellatrix was seated nursing his drink.

"Hello," I said, batting my eyelashes at him.

"Won't you join me in a little drink? What's your pleasure?" he asked.

"What you have there looks good," I replied.

"I know ... but I thought we'd have a drink first," he responded.

I sat next to him in the booth, ensuring that my leg occasionally rubbed against his. I opened my purse and extracted a Virginia Slim; Darleen had commented only yesterday that I should switch to Camels, as they were more reflective of my figure.

"Aren't you going to light my fire?" I asked seductively.

"Certainly," he replied lighting my cigarette, "I was just looking over your kindling."

"I'm Michele," I offered my hand and he kissed it like a gentleman.

I actually prefer it when men kiss it like it was a ladies hand.

"I'm William Fellatrix; have we met before? Maybe in church?" he inquired.

"I don't go to church; kneeling wrinkles my nylons," I replied.

The waitress bought over two drinks and placed them on the table. Mr Fellatrix paid for the drinks and gave her a generous tip.

"Work hard and be kind to your mother," he said; and then turned away from the waitress and back to me.

"So what sort of a woman are you?" he asked me as he sipped his 'Tom Collins'.

"I'm a woman who likes talking to a man who likes to talk," I answered sucking on the cowboy (a situation very familiar to me).

"I should have ordered a 'salty dog'," I went on, "These cowboys are filling me up." (another situation very familiar to me).

"Funny you should bring up dogs; I have just split up with my girlfriend," he said sarcastically.

.... There is more of this story ...

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