A Gangster’s MollA Gangster’s Moll


The astute reader will see some apparent inconsistencies between the implied era of the story and other cultural references. C’est la vie!


My name is Dick. I am a dick and I got one. A trifecta, if you will. But I’m getting ahead of myself.

Dick Taggart, Private Investigator. At least that’s what the sign on the door says. Mostly, I track down cheating wives and husbands and some insurance fraud. I have made the news for some high profile cases I helped the police with, but that’s an uneasy alliance on account of the questionable terms on which I left the force.

Life’s been good. I get around, live on my own terms as much as a guy can, and enjoy some pleasures.

That covers my name and occupation. My possession? That’s the subject of this story, if you know what I mean. Well, it kinda starts with that but my heart takes a big glorious tumble in the meantime.


Sometimes, the sun can hit you like a ton of bricks. But not like this dame. She was more like a structure made out of bricks, if you know what I mean.

I’d seen her around town; a couple of speakeasies, a dance hall. Sweetest face you ever laid eyes on and legs you’d never take your eyes off. Always tending to that scumbag too. How’d a babe like that end up as a mob moll, anyway? No matter. Somehow, the dame got my number. And she dialed it hard.

It was a slow, hot day in the office. Rita was filing papers and sorting my overdue bills and I was chasing after bums who weren’t paying me. Rita was a sheba who just happened to be my secretary. She’s a great doll, putting up with a lot of my shenanigans over the last few years and always lookin’ out for me. Pretty good with a pistol too, but she never got her hands on mine. I always had a thing for her, but I ain’t no sheikh and she seemed to have no end of daddies knocking at her door. Plus, we had to work together.

When Rita brought the dame into the office I saw her roll her eyes and wink at me. Rita knew my soft spots and this doll made them all firm up.

“Michelle Matlin, Dick Taggart,” Rita introduced us and left.

Michelle extended her gloved hand and even through the fabric I could sense the suppleness of her skin.

“Mr. Taggart, thank you for seeing me.”

“A pleasure…Mrs.? Matlin.”

“It is ‘Miss’, thank you. But call me Michelle, please.”

She cut a fine form in the pencil skirt, silk blouse and perfectly seamed stockings and my soft spots were being worked over like a mark after payday.

She sat herself down, surprisingly unsure of herself in this setting. She had a sad look in her eyes that’d put Bambi to shame, but she didn’t take them off me.

“Mr. Taggart, I know we’ve seen each other around town. I know what you probably think, but you’d be wrong.”

“Mostly, anyway.”

She just kept dialin’ that number.

“Call me Dick, Michelle.”

Did she just blush a bit?

“Knuckles and I aren’t involved romantically,” she continued. “He’s married and I am his platonic escort. I guess I look good on his arm.” She lifted her shapely right leg over the left.

“He looks after me, gives me a place, but I still work. I just need to accompany him sometimes. Well, frequently.”

A flick of her hair away from her face.

I wasn’t sure I wanted in on this action, but the month had been slower than the afternoon newsboy, so I let her continue.

“I don’t get involved in his business but I see and hear some things. I am getting concerned about a new venture. I think it is very bad and I don’t want to see it continue. A lot of good people are going to get hurt.”

Her full, round hazel eyes pierced into mine, with a glimmer of pleading.

I’m accustomed to having to do all the work with the skirts I chase. Why did it seem like I was the one being worked now?


Michelle Matlin grew up in an average family and lived an average life. She’d had a number of suitors but they failed to keep her interest. She had met Knuckles when she was working part-time as a waitress while in college. Her mistake was asking him for help when she ran into some money problems. This left her beholden to him, at least in his eyes, and that was how she got into the lifestyle she was now immersed in.

Now, it would be a mistake to think she was unhappy about the whole situation. Knuckles’ generosity gave her a great deal of freedom. But, despite her flamboyant lifestyle, Michelle was lonely. Women despised her for being a slut. Men feared the repercussions of crossing Knuckles by approaching his woman.

She had seen Dick at a couple of clubs, even exchanged words casually. He seemed at ease, despite the apparent threat of Knuckles. Even the waitresses at the club were appreciative that he was a solid, standup guy when she made discrete inquiries.

“I don’t know what it is with Rita and

why SHE hasn’t latched onto him.”

Michelle began to think. “Maybe, I can work both my problems with one solution.”


“How do I fit in the picture, isveçbahis toots?” I asked.

She giggled at the vague endearment. “Well, I am wondering if you’d be willing to do some checking and get some evidence if I’m right.”

She reached out and touched my hand. “I really need your help and by everything I can see, you’re a good and solid man. The kind that knows how to look after a lady.”

She blushed again at just how much she’d given away.

I didn’t miss the cue at all and neither did my namesake, evident from the twitch in my trousers. But I kept my cool, barely.

“You’re asking a lot, toots. I’ve tussled with some tough guys and come out on top, but going after Knuckles is another ball game,” I replied.

“Please Dick. I really don’t want to keep up this life and I am getting a bit scared.”

She now stood and came close to me. Was that my heart or hers beating on my chest?

She rested her head on my shoulder and I thought I heard her sniff. Come on! I’m a sucker for a pretty dame any day, let alone a looker like this…plus she’s crying???? I didn’t stand a chance.

“Okay, no promises. What do you have so far?” I asked.

She perked up. “I have a few documents and a picture but I didn’t bring them with me. Can you come by and have a look?”

“I’m free tomorrow afternoon, say 4:00.”

“Oh, that’s perfect! Thank you so much, Dick!” she gushed.


She kissed my cheek.

Never in recorded history has a simple kiss pierced a soul so deeply, not that I read much history.

The slight tack of her lipstick pulled at my cheek as she drew back, leaving her mark.

“Okay, 4:00 tomorrow. Rita will give you my rate schedule on your way out.”

Rate schedule. Right. I was pretty sure this case was going to be pro boner…err…bono.


I hopped in my breezer and drove to the dame’s house.

It was hot just like every day this time of year, but top down was a great feeling. In about 20 minutes I arrived at her digs; way outta my league, for sure. She told me if there was no answer to come to the pool in the back. Now that thought stirred me. I’d only ever seen her in glad rags at the clubs and my office If she was going to be in poolside attire, I wasn’t sure if I’d remember my own name. I took the flask from my suit pocket to get a dose of courage and made my way around back.

The glow and heat of the sun had nothin’ on this woman. Her radiance illuminated even the darkest thoughts in my little mind.

She lay reclined on a chaise, taking in the rays. One knee was bent and pulled up while the other leg stretched out, her feet adorned with elegant mule-type heels. A bikini concealed her feminine assets but not much else. Bangles dangled from her wrist and her hair spilled against the chaise and over her shoulders.

Next to the chaise was a wine bucket dripping with condensation and a bottle chilling. I noticed it hadn’t been out long as the ice was fresh.

Michelle appeared to be sleeping and didn’t rouse as I approached. I stood next to the chaise wondering what to do. My Johnson was directing the moves and I did nothing to rein him in.

Emboldened with liquid courage, I reached in the bucket and grabbed an ice cube. I touched the cube to her neck and the ice almost sizzled and a cold stream ran down to her shoulder.

She let out a firm gasp, but far from flinching, she further opened her neck to me, her eyes still closed. She murmured satisfaction at the sensation of ice melting on skin as I stroked her neck, then throat, then chest with the cold, wet implement.

The water started to dampen her bikini top. As I moved closer in with the cube, the water was still chilly asas it spilled onto her nipples, and they perked up, threatening to bust through the flimsy fabric.

Her eyes stayed closed, daring me to surprise her with any manner of sensation I could think of. I drew a little closer, and teased the ends of her gorgeous hair while continuing with ice cubes over her upper body.

She continued to moan in appreciation and her now bent knees both parted in invitation to me.

I am nothing if not a tease. While tempting, I wasn’t ready yet to just dive in. Some women are worth the trouble and Michelle was showing she wasn’t even just “some women”.

I brought my mouth within breathing distance of her head but no closer. I whispered sweet sexy nothings as I brought an ice cube to her tummy. She shuddered as a stream made its way onto and inside her bikini bottom. Now, though, the lips of her mouth parted and curled into a slight grin of satisfaction. I am a bit of smooth talker with the dames when I want to be and now it seemed I was dialing her number.

She answered that call and suddenly turned her head to mine and locked lips with me. She tasted of the sweet wine she’d been drinking. The fresh flavour left me with the distinct impression that she never was sleeping in the first place. Didn’t matter, I was happy to indulge her. A guy’s gotta do what a guy’s gotta isveçbahis giriş do and I ain’t no chump.

We kissed in almost every way possible in that moment, our mouths relishing this precoital fuck. Our tongues became well acquainted as they danced and explored. Our lips weren’t left out either as they indulged this new relationship.

Then she slowly pushed me away. Looking deeply into my soul, the unbridled intimacy making me even more horny, she asked in a very husky, starving voice, “Would you like some wine…”


The pause and emphasis on my name left no doubt about what Michelle was after and that the situation with Knuckles was the farthest thing from her mind.

“Why don’t you pour me a glass, toots?”

She reached for the bottle, doing nothing about the cold water dripping off of it.

She seemed to forget about the glass though, as she brought the bottle over her sun drenched body. She tipped the neck and let the nectar spill over her tummy, drenching her bikini bottom and mingling with her own nectar.

“Aren’t you gonna drink…”


She did that Dick thing so well.

Standing at the foot of the chaise, I lowered the foot rest. Michelle further parted her smooth shapely legs, straddling the footrest and I knelt between them, starting at the pool of wine in her belly button.

Again she shivered, this time at the touch of my tongue on her skin. Remarkably, she spread her legs even wider as she shimmied her bottom down the lounge, toward me.

The taste of wine on her skin was an aphrodisiac, not that I needed any encouragement. I was definitely immersed in this woman and my namesake soon would be more immersed, if you know what I mean.

I didn’t miss a drop of the wine as I made my way down between her legs. I made a bit of a show of sucking the wine out of her bikini, kinda like the guy in the coffee commercial who squeezed the spilled coffee from the rug.

Michelle giggled, at least until I lapped the wine off her thighs. She gasped again, slumping further down the chaise. I wish I had a view of us like that: legs spread wide, feet propped up on the mules, my head buried between her legs, with her hands on my shoulders.

Oh my, but that girl’s hips had a mind of their own as I started sucking the wine from her lowest regions. She nearly smothered me, driving my face into her, pressing my tongue against her moistness. I nearly lost my load when she lifted her legs to drop them over my shoulders.

After only a short while though, she pushed me back again, lifting her legs straight up and pulling her bathing suit bottom up and off, leaving the mules on.

“My pussy needs my Dick,” she purred.

For the second time that afternoon I nearly lost my load. A pretty dame who talks street between the sheets? Could put that Viagra company outta business.

I tried not to but couldn’t help staring at at one of the seven smooth, plump and juicy wonders of the world. The pouty lips could put a screen starlet to shame. But she snapped me back.

“My pussy isn’t the only thing, though. Why don’t you let me cool Dick off?”

She was really getting jazzy with the dick thing.

She pulled me to the side of the chaise and deftly undid my trousers and I stepped out of them, leaving my shoes and socks behind.

Now, I am not gonna say my Johnson is first in show, but I do know how to use it. Michelle was impressed to say the least, though. She was beaming as she stroked it, then she leaned in to give it the lightest kiss, leaving her mark of lipstick on the tip. I liked this girl’s attention to detail. She might have to come work for me some day.

She then took the wine bottle, tipped it and drizzled me with the sweetness. I was all wet and before I realized, she had me in her mouth as far as she could take me.

“White wine always goes good with cock, or so I’ve heard,” she declared as she came up for air.

She then took a mouthful of wine straight from the bottle, sealed her lips and pressed against the tip of my hard steel. Best intentions as they say, wine spurted down her chin as she engulfed me again. Her mouth was a little dose of heaven on my cock and I was singing a hallelujah chorus.

I was desperately holding back cumming when I nudged her off me. I pulled her up, and kissed deeply as we struggled getting the rest of our clothing off. I stood back to enjoy the view of her now naked breasts, crowned with those perky nipples. I had a slight sheen of sweat and she ran her tongue over my chest.

“I think you need some more wine, Dick,” she murmured with a plea as she pressed close to me.

Luxuriating in Michelle had become my sole focus. As she presented herself to me, we became even more immersed in each other. I guided her back onto the chaise where she resumed the lurid, erotic display of her luscious body. I crouched as I lifted her legs straight against my chest, feeling the luscious, plump wetness of her girl-like pussy against my cock while kissing her legs. isveçbahis yeni giriş Using my tongue, I traced a line down the back of her calf, then thigh. Lingering at her ass for a moment, I kissed, licked and nibbled, deftly avoiding the fortress she so desperately wanted me to invade. I saw a trail of liquid escape between her thighs and over her pussy as she dribbled more wine over her tummy.

A long, light lick from below her pussy to just above her clit.




I drew one of her engorged lips into my mouth.

“Oh GOD!. Pleeeeeease!”

Firm licks from her perineum to her now very hot hole.


Pressing my mouth firmly against her, lavishing her insides with my tongue.


Moving my mouth up to tease, then deeply massage her clitflesh.

Words became motion as Michelle uncontrollably delivered her wanton pussy to me, her legs using my shoulders as support to grind herself against my face.

She held my head tight as she orgasmed. I wanted to fuck her so badly at that moment, but I wouldn’t deny her the pleasure she was going through. She lightened her grip, dropped her legs to the side and pulled me up by the head. She seemed outside herself, kissing and licking all over my face, feeding me her tongue, wrapping her legs around me and pulling my swollen cock against her sweet and wet, freshly-cummed pussy.

The awkwardness of the position didn’t deter me as I started dry-thrusting (as if you could call that ‘dry’) against her. I could envision the head of my cock rubbing against her clit as her lips stroked the length of my shaft. It didn’t take much imagination to feel her pushing me down, eager to have one of those thrusts enter her and fill her with my passion.

“Fuck me, Dick. Please fuck me,” she whimpered as she pulled her heels against my lower back.

Looking into her eyes and mischievously smiling, I resisted.

“Dick. I need you now. Pleeease…,” the whimpering turned more demanding.

“Just what is it you need, toots?,” I teased. Her face went dark with near exasperation.

“I need your fucking cock inside my pussy, you bastard! Fuck me. PLEASE!!” she begged with a combination of lust, anger and delight.

Mmmmm…sweet and street. What a doll.

Remember that wine from when she blew me? That’s what it felt like as the head of my dick pierced her, juices spilling down my balls. She clutched me tight as I entered her and, lucky girl, the angle put her clit right against my pubic bone and she ground hard against me as we embraced face-to-face. We fucked without thrusting as she held me tight. Fingernails digging into my back, rotating her hips against mine, rolling my cock in her pussy. I was like a cheap sex toy and it felt great letting her use me.

Again, she came but this time with barely a murmur and her body gripped tightly to me. The spasming in her pussy and her fingernails on my back brought me to a whole new level of intensity. After she subsided I started a gentle thrust. The gentleness was betrayed by the fire in my eyes as I gave way to the lurking fierceness. I pulled out, stood her up, put the chaise’ cushions on the ground and directed her to her hands and knees.

By this time, she needed that fierceness. Raising her ass to me, she pulled one of her ass cheeks to the side, showing me the way. I entered her again and gripped her waist. The air was filled with a symphony of growls, whimpers and screams.

“oh god oh god oh god”

“Fuck baby!”


Her delicious wetness and tightness soon got the better of me, not to mention the view of her round ass blending into her waist ending with her now tangled flowing hair. I knew I was about to come and she could tell by my thrusts and groans. You never know, but at minimum, “I’m gonna cum baby!” pretty much gave it away.

“Keep thrusting! I want all of you! Cum inside me Dick!”

Both Dicks got the message and my orgasm racked my body and filled hers. I gripped her hips tightly and she responded by pushing back hard against me, milking me and prolonging the whole body assault I was drowning in.

Michelle and I were both left a sweaty, sated mess tangled in each other from toe to soul. I’d had my share of sweaty fun before but my exhaustion here was heightened by just how much I had poured myself into this beautiful creature. My still hard cock inside her pussy, I leaned over her, kissing her back and holding her breasts. She tilted her head towards me and smiled.

“I want a kiss…”


This time, it was not the playful temptress Michelle. The sweet girl I first met was beckoning me to her. I collapsed next to her and we kissed and held each other as long as the relentless sun would allow.


Michelle had me undone. She never played me for anything, other than that which was to both our benefits: such a sweetheart. We were very discrete about our relationship, and it was painful to maintain distance all the time.

You probably figured out that I did the investigation, between other gigs. I found some interesting things, including the fact that buried in all the shenanigans, there was a power play being made against Knuckles.

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