tagHumor & SatireHarry Dick: Halloween Caper

Harry Dick: Halloween Caper


Harry Dick, Private Investigator, sat in his office watching the evening traffic on 5th Avenue below his window. He was thinking back to the Suckumoff dame's tits and the Family Jewels job he'd cracked for the cops a few weeks before.

"Those were one great pair a knockers," though Harry to himself as a police squad car pulled up in front of the building. Inspector "Boney" Malone stepped out of the car and made his way up the stairs to the building.

Presently, the door to Harry Dick's office opened and "Boney" strode inside. "Ok, you little prick. I got a job that's right up your alley."

"Yeah? Big case, huh?"

"Yeah. Big. You might say that. Get downtown to 1215 Union and see a broad. Her name's Hilda. She'll fill you in. Seems some stuff that got stolen down there. They need it bad. They're having a big Halloween wrestling match tomorrow night. All dame wrestlers too."

"Hmm. Hilda, huh? Swedish dame, right? Sound interesting."

"Yeah. You know the kind. Athletic, blond. You two will get along just fine." Malone snickered then turned and left the office.

Harry leaned even further back in his chair and closed his eyes. He could so Hilda in his mind: tall, maybe 5-10, long, flowing blond hair, giant fun bags just made to be played with, a mouth just perfect to wrap around his Johnson and a Swedish attitude about fucking everyone in sight. "Oh yeah," he thought, "I can handle this."

"I'm ready and willing," smiled Harry's cock from inside Harry's trousers.

An hour later, Harry's 1924 Packard pulled up in front of Rocky's Gym at 1215 Union Street. Harry looked around, patted the nickel platted 38 tucked its holster under the left armpit and pulled open the door. The place smelled like a dirty jock strap that hadn't seen the laundry for years. Moving around the gym, he spied a small office in one corner. He entered the office and saw a large person seated at a desk, bent over some paperwork.

"Hey. I'm looking for Hilda. You seen her?" he said.

The person looked up. It was a woman and she was huge. "Hilda. Dats me. What you want?"

"Uh. Yes. Uh. Inspector Malone sent me down here. I hear you got some problem and..."

"Hey. I ain't fucking that hog," said Harry's cock.

"Ah. You policeman?" Hilda said standing behind the desk. She was fully 6 foot four and 400 pounds. Her large, pendulous boobs hung down to her waist. Harry was horrified by the sight. His wildest dreams of the Nordic Goddess evaporated.

"Oh my God! I'm shriveling!" screamed Harry's cock.

Hilda reached out and grabbed Harry by the lapels and picked him up off the floor. "You kinda skinny for a cop."

"I'm not a cop. I'm a private dick. Now put me down," he squeaked.

"Oh. Private eye. Like dem guys in Mickey Spillane. I tink I like you a lot," she said grinning.

"Um. That's nice. Now please let me down." Hilda set Harry down on the edge of the desk and walked around in front of him.

"You going to help Hilda find her missing stuff?" she asked sweetly while fingering Harry's belt.

"Uh. Yeah. That's why I'm here. Now give me a run down on the what's missing and... um... I'll get out of your way."

"Not so fast, Mr. Private Eye. I hear you guy have really big bran wagers. Is that true?" Again that grin covered Hilda's face.

"Tell her I'm dead. Tell her I have the clap. Tell here anything," whispered Harry's cock.

"Uh. Nope. It's tiny. So small I can hardly find it," Harry murmured. "Tell you what. Here's my card. Just make a list and mail it to me."

"Not so fast Mr. Private Eye. I'm not believing you about your equipment."

"Uh. War wound. It was shot off. Believe me," Harry squirmed.

Harry's pants ripped down the fly beneath Hilda's large hands. She grabbed his cock. "Oh see? It not so small after all," Hilda said, her eyes hungrily staring at Harry's less than impressive, schlong. "I tink it time we see how well it works." Hilda pushed Harry back on her desk as her huge mouth swallowed his cock.

"Oh Shit!" screamed Harry's cock. "I'm wanting you bad, Mr. Private Eye," choked Hilda.

"HELP," screamed Harry.

"No! Anything but this," pleaded Harry's cock.

"I fuck you really good now," whispered Hilda as she hiked up her skirt and leaped onto Harry, burying him under 400 pounds of blubber. Harry's struggles and scream were stifled by the mountain of flesh that crushed him. Just breathing was almost more than he could do. Harry's cock had turned blue from lack of oxygen.

"What wrong?" asked Hilda, "You no hard. You don't like, Hilda?" Hilda lay on top of Harry crying.

"No, baby. I like you just fine. Umm. But I don't do this during office hours. Umm. A long time rule. Not get your fat...Umm... I mean, please let me up," Harry pleaded.

Hilda rolled off to stand behind the desk still crying.

"It's ok, baby. Umm. Maybe another time. Now. Down to business." Harry limped, sagging into a chair. "Okay. What was stolen?"

Hilda sat in her chair. "Oh. All our decorations, Mr. Private Eye," she said shaking her head. "There were garlands for the ropes, a really nice, what you call, Jack-O-Lantern for the entry and some skeletons we were going to hang around the outside of the ring. And the match is tomorrow night," Hilda cried.

"Ok, baby," Harry said trying not to look at Hilda massive boobs and the rolls of flab. "Now, who had access to all this stuff?"

Harry questioned Hilda until he thought he had a place to start. One of the wrestlers, a certain Ms. Ripya Hardon, was planning a Halloween party for after the matches. This seemed like a good place to begin his investigation. "So, where do I find this dame?" he inquired.

"Oh. She live in rooming house on Lincoln Street. I give you address."

Harry took the address and swaggered out to his car. Soon he was on the cross-town expressway headed for the Lincoln address.

He climbed the stairs and pressed the call button next to Ms. Hardon's name. Apartment 3B he noted.

"Ello?" came the response.

"Harry Dick here, Private Eye. I need to talk to you," he announced in his best tough-guy voice.

"Okay. Wait a second."

A buzzer sounded and Harry pushed open the door and climbed the stairs to the third floor. He knocked on the door. Momentarily the door opened and in front of him stood a raven haired bomb shell. She had giant gazongas, long, slender legs, nice, trim ass and a the face of an angel with lips to die for. Best of all, she was butt naked. "I'm Ripya Hardon. What you want?" she asked in a sultry voice.

Harry's cock gave a lurch. "Harry Dick. I wanna ask you some questions. You were at the gym early this morning. Right?"

"Yeah. I go to the gym every morning."

"You didn't see any Halloween decorations, did you?"

"Yeah. I seen um. What about them?" Ripya looked uncomfortable.

"You didn't take them did you?"

"Take them? Yes. They belong to me."

"They belong to you? I thought they belonged to the gym," Harry said scratching his head and leering at the nipples in front of him.

"No. They're mine. The gym borrowed them last year for the annual event. They never gave them back. So I got them this morning for my party." Ripya tried to cover her tits with her arm. It wasn't anywhere big enough.

"Ok. So, why'd you take them without asking?" Harry asked as his eyes drifted downward to Ripya's shaven twat.

"Hey. I told Hilda I wanted them. Just before she fired me. So I took them and left."

"I see. So you aren't working tomorrow night?" Harry thought out loud, his cock reacting to an interesting thought.

"Naw. I'm going to look around for another gym next week. In the meantime I'm throwing a party for my friends tomorrow. You can come if you want."

Harry's cock almost jumped out of his pants. "Right. I got some work to do, but I'll see you tomorrow night, beautiful." Harry winked and turned for the door.

"Oh, by the way. Almost all my friends are women wrestlers. I hope that doesn't bother you," Ripya said shyly.

"If they look anything like you, baby, I'm in pure heaven," Harry smiled then was out the door.

Harry hurried down to his car and drove to the 3rd Avenue precinct. Inside he found Boney Malone. "You fuckwad! You almost got me killed," he said less than casually.

Boney grinned at Harry. "Well. I see you met Hilda and you lived," he said chuckling.

"Yeah. And I solved the case too. There was no theft. The stuff belonged to one of Hilda's wrestlers. She took it home with her," Harry said with a smile, "and here's the best part. I'm going to her party. The place will be filled with hot scrunch. Makes ya jealous, don't it?"

"Dick. You couldn't get laid in a whore house."

"You wanna put some dough down on that, Boney?"

"Okay. I got a saw buck says you're home by nine with your girlfriend, Polly Palm," Boney said laughing.

"You're on, asshole." Harry walked back to his car and drove to his office.

He picked up the phone and dialed the gym.

"Hello?" Hilda answered.

"Harry Dick, here. Look. The stuff you lost ain't lost. The Hardon dame has it and she says it's hers. So I guess you're shit out of luck." Harry quickly hung up the phone. Then he leaned back in his office chair and closed his eyes. Visions of hot, sexy broads danced through his mind. Every one was naked, huge knockers bouncing around as they pleaded for him to screw them. A smile of anticipation crossed Harry's lips.

"Oh yeah. Tomorrow night we are going to get some," crooned Harry's cock. "You better not fuck this one up, asshole."


Harry parked the Packard in front of Ripya's rooming house at 8:30 PM and walked up to the door. He pressed the button next to 3B and waited.

"Ello?" came Ripya's voice.

"Harry Dick here." The buzzer sounded and Harry opened the door and climbed the stairs. The door to 3B was open so Harry went in. The place was in a genuine party mode. Naked women bounded about, tits flying everywhere. Bare asses went by. Harry's cock jumped for joy. Someone handed him a drink.

Around the walls all the missing Halloween decorations were hung. The garlands were strung from high on the walls to the lamp in the middle of the living room. The skeletons hung at the doorways. The Jack-O-Lantern sat on the coffee table filled with what looked like condoms and candy.

"Oh. Mr. Harry Dick," said Ripya. "Hey everyone. This is Harry. He's a Private Eye." Everyone laughed and gathered naked around Harry. He was in heaven.

"Hey, be cool. Don't look too interested," Harry's cock whispered to him.

Harry mingled. As near as he could tell there were fifteen naked pairs of boobs and butts. He didn't see any other men there at all. His cock was getting harder by the minute. On his third drink, Harry struck up a conversation with a tall blond named, Justya Tryme.

"I take it you're a wrestler too. Is that right?" Harry asked as he stared at her rosy nipples.

"Oh yes. All of us are. I'm East Coast Champ, you know," Justya said smiling.

"Oh really? And how did you win that?"

"Silly. You don't win that. We take turns. It's all fake, you know," Justya winked.

"I see. But it looks to me like those are real," Harry said pointing at Justya's fun bags.

"Oh yes. Of course. They haven't invented boob jobs yet. It's 1946, you silly goose."

They both laughed. Harry's arm slid around Justya's shoulders just as Ripya Hardon announced a party game.

"Okay. Listen up people. We only have one guy here. So we have to take turns."

Harry's cock was beginning to hurt.

Holding a bowl high over her head Ripya said to the crowd, "There's a slip of paper with each of your names on it in here. Harry you can do the honors of drawing the first name."

Trembling, Harry reached into the bowl. He unfolded a scrap of paper and read aloud, "Wanda Whip." A brown haired woman in the crowd raised her hand and danced forward screaming, "Me. Me." Wanda grabbed Harry by the hand and dragged him into the bedroom. The crowd followed laughing.

Before he knew it, Harry was standing next to the bed. His clothes had been ripped off him by the crowd. His cock stood at attention, ready.

Wanda took his cock in her hand and stroked it slowly. "You like?" she cooed.

"HELL YES," answered Harry's cock with a dribble of precum.

Wanda pushed Harry back on the bed and licked the head of his cock. "Oh my God," moan Harry.

He hardly noticed when other women took his arms and feet and tied him spread eagle on the bed. Harry was immovable. Harry opened his eyes when Wanda stopped licking.

In front of his face was a huge pair of tongs. "What the fuck?" he screamed. The women all laughed, began kissing and foundling each other as Wanda moved the tongs toward Harry's genitals.


Harry staggered up to his office at 9:30 the next morning. "Horrible night. Ghastly," he grumbled. "How the fuck was I supposed to know they were a bunch of fucking man hating dykes?" His cock had nothing to say. In fact, his cock probably would be able to talk at all for a week while it recovered.

The office door opened as he tried to stuff the key into the lock. There stood Hilda, butt naked. Her sagging tits hung down to her enormous waist. Her furry bush already glistening with wetness.

"Hi, Mr. Private Eye. I was waiting for you all night." Grinning, Hilda grabbed Harry by the arm and dragged him into the office. The door slammed. The screams from Harry and his cock went on for hours.

Report Story

byJenny_Jackson© 11 comments/ 15730 views/ 1 favorites
1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (11 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (11)

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: