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The Case Files of Cindy Masters

Author: 

  • Trapper Jock McIntyre

Organizational: 

  • Title Page

Audience Rating: 

  • Mature Subjects (pg15)
The Case Files of Cindy Masters

The Case Files of Cindy Masters, Dyke Detective: A Chance Encounter Pt2

Author: 

  • Trapper Jock McIntyre

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Fiction

Genre: 

  • Transgender
  • Crossdressing

Character Age: 

  • Mature / Thirty+

TG Themes: 

  • Female to Male
  • Lesbian Romance
  • Lesbian Fantasy

Other Keywords: 

  • lesbian
  • FTM Crossdressing
  • Tomboy
  • Hard-Boiled Detective

Permission: 

  • Posted by author(s)

Masters.jpg
The Case Files of Cindy Masters, Dyke Detective
This Episode: A Chance Encounter - Part Two
by Trapper Jock McIntyre

Masters is the name. Cindy Masters. I'm a detective. I get $50 a day and expenses, $75 if I can get it.

I got to Won Huong-Lo's and ordered a bowl of chop suey. Won was a chubby looking guy with a basket between his legs that resembled a hamster munching on carrot, a sight that made me give thanks for the fact that at least I can pick and choose the contents of my Fruit of the Looms. As I sat there chasing some rice around the plate with my chopsticks, Won came out of the kitchen. A trail of the steamy smell of overcooked chicken followed him.

"Ah, Masters, so nice to have you back in my establishment again," he said with a mouth full of teeth that looked as if they had never learned how to line up in formation.

"Cut the crap, Won, I'm here on business. Your boy over there said that you wouldn't see anyone unless they order a meal. Is this part of your new plan to poison all of San Francisco," I spat.

Won looked at me with disapproval "Pity your attitude there my boi, I always though that you were a person of higher quality"

The chop suey began to congeal in front of me. "Look, fat boy, I need some answers. What do you know about certain articles of antiquity being sold on the black-market?"

"Ah, masters, your turn to cut the crap, for surely you mean the Dexterous Dildo of Denmark," he observed.

The thought of the fake phallus and its appeal yielded an almost Pavlovian response of slickness in my y-fronts. "Alright, so that's what I'm looking for, so what do you know?"

"Masters, my boi, have you forgotten that I don't ever know anything without a gratuity," Won replied with a smirk on his face.

"You are one cheap SOB," I shot back as I tossed a twenty at him.

As he held it up to the light, I snorted at his mistrust. "Don't worry, its real!"

"I hope so. Some of the ones I've been getting lately have been about as genuine as those rubber cocks you stuff in your jockstrap or in certain other mysterious places when you play hide the meatless sausage," he stated with a smirk.

I reached over and grabbed him by the neck and his eyes began to pop out like the nipples on a drag queen's false tits. "My cocks and their hiding places are none of your business buster"

Won began choking "Alright, enough. Seems that I just overheard some discussion back in the weight room trying to sell it off to the highest bidder"

"What about a ransom for it?" I queried as I let him back

"Oh it's gone way past that. This dildo is far too hard to hold onto. The culprits want to get rid of it as soon as possible," he pointed out as he gathered his composure.

The air was getting heavy. I lit a Lucky Strike and I loosened my tie. After taking a long suck on it I tried to stroke him for more information. "And what else?"

"What do mean what else?" he answered. "I've told you all that I know!"

"For that I paid 20 bucks. You ougtha be strung up" as I raised the back of my hand to him to slap him.

Won drew back. "Wait!" he exclaimed as he wiped the sweat from his brow. "There's a man in the weight room. He's making a deal."

I lowered my hand and pushed away the chop suey.

"That's more like it" I leaned forward. "Who's the man?"

"Harry, the Banana, Bowles"

Upon hearing the name, the vaginal wetness I had felt earlier from talk of the dildo dried up like a swimsuit left to hang on a cactus in Death Valley. The hairs on my vagina stood on end in my y-fronts. For the first time in this case I concluded that maybe I should have gone to Fire Island for the winter. The Banana liked his men, and he liked them big. This was one time that I was glad that I had a selection of packie-penises for all seasons in my duffel bag.

I pushed back my chair, grabbed my sack, and turned to head to the gym in the back of the eatery.

"Masters, one thing" Won yelled.

"What" I barked

"You'll need this for protection," he said as he tossed me a packet containing a rubber.

"I squinted at him, what make you think I don't carry my own" I asked.

"Its on the house." He laughed. "Oh and Masters, that'll be $1.25 for the chop suey."

As I walked through the door to gym area, I could smell the musky scent of masculinity. It made me wish I could bottle it and splash it on myself every morning. A cute twinky boy walked along the lockers and the sight of him reminded me of a tomboy-girl I had once bought a strap-on for back in Havana. Approaching a locker I stripped down to my undershirt and y-fronts. Making sure that no one was around, I whipped off my y-fronts. I reached in to my duffle bag and pulled out my jockstrap. Fishing in the pocket on the side of the gym bag, I selected the good old Super Chief Streamliner. Eight inches of ersatz phallic delight all made possible by advances with rubber during the war. As I set my cock on the shelf of my locker, I thanked my self for having saved scraps and planted a victory garden during the conflict.

I quickly pulled the jockstrap up my legs and nestled my not-so-little rubber friend in the pouch, positioning the balls at the bases of my labia, and dressing my new cock to the right. After adjusting the straps of my Bike #10 jockstrap around my ass cheeks, I pulled on my trunks and a t-shirt, followed by my gym shoes. The latch on the locker door wouldn't catch so I closed it and hoped for the best.

As I walked into the weight room, I conspicuously adjusted my willy making sure that The Banana noticed. The atmosphere reminded me of how it must feel to be a hotdog vendor at the ballpark on opening day. I sat down on a weight bench and spread my legs.

----tune in soon for the next chapter in the The Case File of Cindy Masters, Dyke Detective

The Case Files of Cindy Masters, Dyke Detective: A Chance Encounter

Author: 

  • Trapper Jock McIntyre

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Fiction

Genre: 

  • Transgender
  • Crossdressing
  • Mystery or Suspense

Character Age: 

  • Mature / Thirty+

TG Themes: 

  • Female to Male
  • Lesbian Romance
  • Lesbian Fantasy

Other Keywords: 

  • lesbian
  • FTM Crossdressing
  • Tomboy
  • Hard-Boiled Detective

Permission: 

  • Posted by author(s)

Masters.jpg
The Case Files of Cindy Masters, Dyke Detective
This Episode: A Chance Encounter - Part One
by Trapper Jock McIntyre

Masters is the name. Cindy Masters. I'm a detective. I get $50 a day and expenses, $75 if I can get it.

I was sitting in my office trying to figure out how to get lipstick stains out of a silk tie, or preferably onto one, when I heard the clickity-clack of high heels coming down the hallway toward my door. I looked up to see a silhouette through the frosted glass that resembled two letter B's that hadn't learned that in the missionary position you where supposed to face toward each other.

The door creaked opened and having thoughts about what I'd be facing, I reached slowly for the rod I was packing. She entered my office and walked up to me with her hips swaying in a samba that made Xavier Cugat sound like Spike Jones.

"Ms Masters, I suppose." She asked.

I let go of my rod and tapped a cigarette out the pack. As I lit it, I replied, "You suppose right, dollface."

I took a drag from my Lucky Strike and held out the pack for her, "Care for a fag" I offered. As she nodded okay, her dangling earring clanged like wind chimes. As I lit her smoke, she leaned forward and began to tell me her troubles, as if dames like her should have any cares in the world apart from what dress to wear. As she spoke her the sight of her blood red lips led to a throbbing in my jockey y-fronts, with my clit beating out a rhythm like the Morse code for 'LICK ME".

I leaned back in my chair and placed my feet on the desk, my freshly shined wing-tip shoes glistening like licorice jellybeans. As I listened to her voice, my eyes did a mental strip search and I made a mental note to stop at the Piggly-Wiggly to buy cantaloupes on the way home

"I assume you've heard of the Dextrous Dildo of Denmark," she asked.

"Heard of it? I've had dreams of wearing it and using it" I replied. My nipples hardened and tingled against the ace bandage I used to flatten down my breasts as images of the dildo darted in and out of my mind's eye.

Her voice took on the tone of school teacher. "The dildo has been in our family for years, but last night it disappeared from the safe in our library. Our oriental houseboy has also disappeared and we think he may have stolen it for war profiteers in Japan to hold for ransom"

"Write it up and sell it to Paramount. So what does this have to do with me? I take no sides in these petty little post-war disputes," I spat.

"We need to get that dildo back, and our family is willing to pay for it. It leaves a hole in our legacy that must not remain empty, " she remarked in a voice that purred like 47 Packard sedan.

"Listen sister, I know a lot of holes that need filled. Why didn't you report it to cops?" I shot back.

A dark pallor washed over her face. "The cops mustn't know."

I felt a tightening in my y-fronts at those words. I may be a flatfoot and work just this side of the law, but I don't like to be played a sucker, that is unless the suckee is wearing a jockstrap. "Look here, sweet cheeks. I'm going to give it to you straight and hard. Either you spill the load, or you get yourself another boi."

With that her eyes got all misty and those pretty little red lips all pouty. She pulled a hanky out of her purse and dabbed at her eyes.

"We, we, we got a ransom note. They said if we called the cops, they'd kill daddy"

Now it became as clear as glass filled with mineral oil ready to be used for a rubdown. Daddy, as she was called, ran a chain a lady's clubs in Castro, where the girls could stuff dollar bills into the empty jockstrap pouches of the go-go tomboys who perambulated along the stage and for a half a saw buck more traded in the backroom would give a lap-dance to anything in a skirt, or in my case, a three piece suit.

Feeling my resistance drop to below sea level, I offered a deal. "Yeah, alright all ready, stop your blubbering. It'll be a 100 clams to start."

She got up and walked over to my side of the desk. Reaching between her breasts, she pulled out a roll of twenties; counted out 5 Jacksons then stashed the rest back in their nest. Bending down to kiss me, her hand made its way down to my trousers, where she unzipped them and then stashed the currency in the fly of my y-fronts, as she ran one of her long red nails along the lips of my vagina.

My vision cleared and my head stopped spinning like the beacon top of lighthouse leaving me with a clitoral erection I could pound nails with.

"Here's my card. You can call me at Mayfair 2176" she purred. With that she mamboed back to the door as I stared into space.

Recovering my composure, I planned my next move. If anyone knew the oriental black-market, it would be my acquaintance Won Huong-Lo, He ran a gay Chinese restaurant, gym and rub joint just outside of Chinatown. He had a finger in everything behind the scenes and was so cheap that if there was a quarter in San Francisco bay he'd drop his mother in it and tell her to hold her nose and if she came up covered in seaweed he'd dump back in to get fish for sushi while he went to get rice.

Pausing only long enough to stuff a dufflebag with a jockstrap, trunks and a t-shirt so I could make some contacts in the gym, I headed out and hailed a cab.

----tune in soon for the next chapter in the The Case File of Cindy Masters, Dyke Detective


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