Chicago Style Valentines Day

The two young men stood hunched against the bitter wind reading the front page of the Chicago Tribune. Directly below the date--February 13, 1929--was the headline that held their collective interest: CAPONE TO BE IN MIAMI VALENTINE'S DAY.

"It's too fuckin' beautiful," hooted Willy Marks.

"Too good to be fuckin' true," added Jimmy Clark as he folded the paper under his arm. "Let's get outta this wind."

The two walked down the side walk toward a coffee shop, careful to avoid getting mud on their spats. They were nearly identically dressed in snap brim fedoras and long overcoats which covered dark pinstriped suits.

"The boss is gonna love that fat bastard being outta town," said Jimmy.

"Lucky fat bastard," replied Willy. "At least he's outta this wind."

The boss was George "Bugs" Moran, head of the North Side Gang and sworn enemy of Al Capone.

Once inside the coffee shop, Willy and Jimmy doffed their coats and hats and hung them near the door. They slid into the nearest booth as a waitress came up to take their order. She was a pretty girl, too much makeup but a generous bosom.

"What'll ya have, gents?" she said before biting the tip of her pen with sharp looking white teeth. Her red lips formed a perfect O around it.

Willy stretched his arm over the back of his seat and said, with a sly grin, "How 'bout a blowjob?"

The two men cackled at the joke and the girl, spying the grip of Willy snub nosed revolver, joined in cautiously.

"Sorry, hon, that's not on the menu today." she said.

"Oh, what day are they served?" asked Jimmy Clark.

"Yeah. We'll be back," said Willy Marks.

"How about February 29th?" the waitress said with a genuine grin this time.

The men gaffawed.

"But leap year was last year. Means we'll have to wait three more years." said Willy.

"Well, if you come back in three years, blow jobs will be on the menu," she rejoined, with a wink.

Jimmy said, "Fair enough sweetheart. For now, we'll take a couple cups of coffee."

They watched with wide grins as the waitress moved away, swinging her hips perhaps a bit more than necessary. Then they caught each others eyes and arched their bows simultaneously-Barney Google style. The day was going real well except for the fucking weather. Goddamn Chicago wind.

"Things'll go real smooth with Capone outta town," started Willy.

"Shouldn't be a hitch."

"So we meet up at the garage what time?"

"Bugs says 10:30."

"Which garage again?"

"The one at 2212 North Clark."

The waitress delivered two cups of steaming coffee. Both men grinned up at her then eyed her bursting chest. The girl smiled down and threw her shoulders back causing her breasts to thrust out even more before she stepped away to another customer.

Willy and Jimmy watched her backside sway away once more before dumping cream and sugar into their hot coffee.

"Whose the gang?" asked Willy.

"The usual. Jonny May, Frankie and Pete G. Ted and Bugs, acourse."

"That asshole Reinhardt gonna be there?"

"Probably." Jimmy looked out the window. "He always is."

Reinhardt Schwimmer was an eye doctor who got a kick out of hanging out with gangsters. Bugs Moran allowed it because he got off on watching Schwimmer ball his wife, Alice. Jimmy knew this because he was married to Moran's sister, Aggie. And Alice and Aggie shared everything.

Willy said, "I can't believe Bugs got such a deal on that much booze. Shit, it'll be almost a ninety percent markup."

Jimmy nodded and sipped his coffee. "You drivin' Bugs?"

"Usually do."

"I'll be with Frankie and Pete. Probably Jonny and Schwimmer."

Jimmy gazed out the window for a moment. He realized the flirtation with the waitress had gotten him a little worked up. He hesitated only bit before asking, "So...have you thought about it?"

Willy eyed him carefully.

"Well, yeah."

Jimmy could hear in his head his wife's voice as she told him about Moran watching Reinhardt Shwimmer shtup her sister-in-law. He remembered the feel of her mouth on his dick as she made her request.

"She really wants to try it, Willy."

"Why me?"

"You're my best pal. And she likes ya."

"Why tonight?"

Jimmy winked. "Be a great Valentine's Day gift, wouldn't it?"

"Valentine's Day is tomorrow."

"Yeah, but the kids are gone tonight."

Willy watched the waitress bustling about. He'd always found Aggie attractive but never acted on it for obvious reasons. Now this strange proposal Jimmy had been offering for the past few days had him spinning. Not only would Jimmy watch, his wife wanted him to join in. A threesome.

The waitress bent over to clean a table. What a fuckin' ass!

Shit, why not.

"What time you want me to show up?"

Jimmy's face split wide open in a grin.

"How about eight o'clock?"

The two men finished their coffee in a palpable silence.

They tipped the waitress generously before leaving the coffee shop.

******

Willy Marks arrived at the Clarks apartment a few minutes past 8:00pm. He had considered bringing something but for the life of him could figure out what. Flowers didn't seem right. And he knew Jimmy would have plenty of booze.

Jimmy met him at the door dressed in a blue silk robe. Willy could tell he had had a few. He also had the feeling that his friend was naked beneath the robe.

Jimmy led him into the warm living room. Candles lit the way in flickering orange glow.

"Happy Valentine's Day, honey," Jimmy chirped, almost too gleefully.

Aggie was seated on the chaise lounge. She wore only a shiny full slip and a strand of large black pearls. Willy could see the impression of her taut nipples straining against the moist looking fabric. Her dark hair was cut in a Theda Bara style, bangs and short on the sides and back. She gazed at him with a mixture of apprehension and lust. After a rather long sip of her glass of gin, Aggie rose and moved toward the men.

She carefully took her husband's arm and rested her head on his shoulder looking at Willy.

"I'm so glad you decided to do this, Willy," she said, looking at him with half closed eyes.

Willy thought any reply he could make would have been inane so said nothing.

Finally, Jimmy broke the silence: "How 'bout a drink, Will? Aggie, take his hat and coat while I get him a drink."

Jimmy moved to the bar and Aggie received the hat and coat Willy handed her. But before putting them away, she leaned into him and huskily said, "I've been waiting for this for a long time."

She slid her hand under his suit coat and brushed the front of his crotch. Willy Marks manhood popped to attention at her touch.

Smiling, Aggie Clark whirled away and took the clothes to the hall closet.

Jimmy delivered Willy's drink which Willy took a deep swallow of. Jimmy sipped his own gin. Willy looked after where Aggie had gone and turned to Jimmy. "So, how's this gonna work?"

Jimmy sat down on a small sofa and said, "It's her ballpark. Let's let her pitch. Have a seat."

Willy sat down next to Jimmy just as Aggie returned.

When she caught sight of the two men sitting on the sofa, Jimmy Clark's wife's face broke into a broad grin. Then, slowly twisting the long strand of pearls out and around her neck, she moved towards the phonegraph. She selected a record and placed it on the turntable. Then carefully adjusted the needle at the start. A smooth jazz filled the air. Willy didn't recognise it but thought it was some of that great stuff the Negroes were creating.

Aggie danced toward the men, her slightly chunky ass swaying to the beat.

Willy marveled at the movement of her hips and at the bouncing of her pert breasts. He felt his cock come to life in his trousers. Beside him, Jimmy shifted slightly as though he also had experienced a shift of flesh.

Aggie stopped before them and looked for a moment into Willy eyes. Then she knelt before her husband and slowly drew her hands the length of his thighs toward his crotch.

"Alice says she always sucks Bugs's dick before she screws Rienhardt," she said, a slight wickedness glinting in her eyes. She said specifically to Willy, "She says it helps my brother get hard."

She had a firm hold on Jimmy's growing cock.

"Doesn't look like that'll be a problem with you, babe," she smiled.

Aggie spread open skirt of the blue silk robe and Jimmy's long penis stood up toward her.

Although Willy had seen other guys pricks before, pissing in an alley and whatnot, he had never seen one, other than his own, erect. It was dark red and crisscrossed with veins, the purple head breaking through the foreskin as it grew to full length at the urging of Aggie hands.

"So, want me to suck your cock, baby," Aggie crooned. She reached her tongue forward and lightly licked the head.

A deep groan sounded in Jimmy's throat in answer. Willy member was straining against the zipper of his pants.

Aggie took the tip of Jimmy's cock in her succulent mouth. Her red lips clamping down hard on it. Then she released the morsel and licked up and down the shaft, her tongue finding every crevice and hill. Soon, Jimmy's pubic hair was soaked with her saliva.

Willy, not married, had been with girlfriends and a whore or two but never had anyone give him a blowjob like he was witnessing. It was like she was totally in love with her husband's cock. Like every the smell and taste entranced her. Her devotion was complete.

That is until she took about half the big thing in her mouth and looked not at Jimmy, but at Willy. First at the growing tent in his pants, then into his eyes. She stared directly into his eyes while she sucked Jimmy's big prick.

Then she let the cock plop out of her mouth and still stroking it, she said to Willy, "Let me see it." Aggie licked her lips.

Willy looked at Jimmy, who nodded back, then he unzipped his trousers and pulled his cock through the fly. It was rampantly hard. Not as long as Jimmy's but a bit thicker.

A throaty "Ooooh" escaped from Aggie's lips.

Jimmy, who like Willy, had never seen an erect dick before, felt slightly uncomfortable at his own fascination with the thick tube of flesh. His cock got even harder in his wife's hand. One hand now because Aggie had loosed her other hand to gently finger the newcomer.

The mere touch of her fingers forced a drop of pre-come to the tip of Willy cockhead. Aggie gathered it on the pad of her index finger and smeared it all over the knob like head.

It was Willy's turn to take in a breath of air. His prick bobbed up and down in the air, forcing a giggle from both Aggie and Jimmy.

Aggie continued stroking the two cocks, her interest in Willy growing rapidly. Then she asked her husband, "Can I suck his big prick, Jimmy?"

Jimmy, who had become completely speechless, only nodded.

So, still stroking her husband's cock, Aggie Clark brought her sweet mouth to the tip of another man's penis. Willy tensed at the feel of her mouth as it engulfed the cockhead. His hand went to her dark hair, digging into it as she took inch after inch of him into the warm cavern. He thrilled as her tongue flicked at the underside of his shaft. When she started bobbing her head up and down on him, he shuddered at the feel of his impending doom.

But before that came, Aggie broke her suction and dropped his prick from her mouth.

"Nice and thick, Jimmy. Not as long as yours but thicker." She stroked the two hard cocks with simultaneous action.

"Stand up, boys. I want you both to come in my mouth at the same time."

The two men stood. Jimmy opened his robe completely as his hard cock bounced against his flat belly, the head of it reaching his navel. Willy pulled off his suit coat and shucked down his suspenders and opened his trousers, letting them and his drawers drop around his ankles. His cock stood out, straight as an arrow.

Aggie grasped each prick in a hand and gave each one a good suck on the head. Kneeling before them may have seemed like surrender but she knew who was in charge. It was just like Alice had described it.

The spaghetti strap of her gown slipped down over her shoulder to expose one of her breasts. Willy thought it the most beautiful tit he had ever seen. Not overly large but perfect in shape with the long pink nipple jutting upward.

Aggie took turns sucking each cock, trying to divide her time equally as Alice had instructed her. But before very long she had an idea all her own. Pushing the two cockheads together, she engulfed both with her warm mouth and sucked hard.

The two men reached out to steady each other. Since their cocks were melded in her mouth it didn't seem odd to help each other hold on for dear life.

Jimmy's wife looked up at them with brown eyes glossed over in lust. Her own private place was awash in her own fluids. She was nearly delirious with the mere idea of what she was doing. She wanted to get one of them--preferably Willy--inside her pussy. But Alice had been adamant. Suck them off first because their second erections would last longer.

She released them from her lips only to say, "You big dicks ready to come." Alice had tld her to use naughty language.

Both men nodded feverishly. Aggie pulled her slip over her head exposing her compact body. Her breasts bounced delightfully, their pink nipples fully engorged. She left the pearls on, their blackness magnified by her white skin.

"You first Willy."

Then she burst into a slightly giddy laugh.

"Give me yer willie, Willy."

Aggie put his cock in her mouth, then grabbed his ass cheeks. Pulling on his ass, she drove half his prick into her mouth. She let him fall back and the pulled him forward, burying her nose in his pubic hair. She developed a rhythm and Willy put his hands in her hair to urge her onward.

Jimmy watched his wife suck his best friend's cock. He knew he should be feeling differently but, truth be told, he had never been so excited in his life. He stroked his prick while he watched Willy's thick flesh disappear again and again into her waiting mouth.

"Fuck her, Willy," he said. "Fuck her mouth."

Willy was fucking her mouth hard, matching her movements with thrusts of his own. When his head went back and he held her head tightly, Aggie opened her mouth so her husband could see his come land on her tongue. Willy roared as his orgasm arrived.

Jimmy watched as thick ropes of semen spurted from the slit and shot through the air to land on Aggie's writhing mouth muscle. He nearly went over the edge himself before pulling her head to him and driving his rod into her perfect mouth. Aggie held her husband deep in her mouth as he shot his load. Willy, still erupting, stroked his cock, draining it as his come landed on Aggie's cheek, her nose, her breasts. Landed on Jimmy's cock, for Chist's sake. He had never come so much in his life.

Aggie sucked all of the cream from her husband's dick then stood and kissed him with it still in her mouth. Alice had suggested this also. Jimmy pulled back slightly, then relented only to savor the taste. Aggie placed her other arm around Willy neck and kissed him as well. He was in heaven.

Jimmy dove his head into her soft shoulder and neck as he placed a hand on her round bottom. Willy's hand found her other cheek as he kissed her, tasting the semen on her tongue.

Finally, Aggie released her two lovers and thrust her hand between her legs.

"My god, I've gotta come soon," she groaned. Both men massaged her behind and cupped a breast. They lowered their mouths to suckle her long pink nipples.

Aggie touched herself as she submitted to their lovemaking. Then she felt something bump against her hip. She looked down to see that Willy was still hard as a rock.

"Goodness, Jimmy, look. Willy's willie is rarin' to go."

Jimmy looked down and was impressed by the hard prick. His own was at half mast.

Aggie acted quickly. She grabbed Willy by the dick and marched him out of the room, saying, "I think it's time to adjourn to the bedroom. C'mon Jimmy, watch him fuck me."

Her sweet little body jounced and jostled as she lead Willy, who still had his pants around his ankles, down the hallway.

Jimmy grabbed a bottle of gin and a couple glasses and followed directly. By the time he got to the bedroom, Willy had taken off his shirt and kicked off his shoes and pants. He was standing before Aggie who was sitting on the edge of the bed cooing over his erect dong. "So amazing, so hard, so beautiful."

"Aggie, it all because of you. It's never happened to me before."

Jimmy poured a drink as he watched her take the purple knob into her mouth again. He handed the drink to Willy and poured another for himself. They both tossed the drinks down.

Once Aggie was satisfied that Willy was as hard as he could possibly be, she lay back on the bed and spread her legs for him invitingly.

"C'mon, lover. Give me that big dick. Put inside me, baby."

Willy knelt on the bed between her legs. He caressed her moist pussy as its fragrance drifted upward to his nostrils. She smelled of sex, sweet and musky. He took his hard cock in hand and placed the engorged head against her slippery slit.

"I've only ever been with Jimmy, Willy. You will be only the second man to fuck me. Does that please you?"

Willy hoarsely whispered, "More than anything."

"Are you watching, Jimmy? Willy is gonna fill me with his big dick now. Does that please you?"

Jimmy spoke quietly, "More than anything."

"Are you sure, Jimmy? Once he's in me it'll be too late. We won't be able to stop. I won't be able to stop. Are you sure?"

Jimmy took another drink, right out of the bottle. "I'm sure."

"Are you sure you want to fuck me, Willy?"

"YES!"

"Then do it! Fill me with your cock! Make me come while Jimmy watches!"

Willy drove his hardness into her moist place. Aggie lifted her hips to accept him fully, clenching the harpoon tightly within her.

"My god, so full, so deep," she cried.

Willy held himself there as she became accustomed to his girth. She made little jerky adjustments.

Jimmy watched his friend's dick disappear into his wife's cunt and, once again, did not feel what he thought he should. His own cock began to rise in excitement. He moved closer to the bed to show his wife the result of her desires.

Aggie saw Jimmy's erection and grasped it in her hand. It was just what Alice said would happen. "Sweet baby, your almost ready, too. But this is Willy's turn. Come on and fuck me, Willy. Fuck me hard."

And Willy did. He thrust his cock in and out of her with long hard strokes. She accepted him readily meeting each thrust by grinding into him. Her long awaited release was at last at hand.

"Touch me! Touch my body! Both of you! Kiss my tits," she growled.

Willy reached under and grabbed her ass cheeks, squeezing and kneading the soft flesh with his hands. Jimmy bent over and caressed his wife's breasts, taking one long nipple between his teeth the way he knew she liked. He gnawed on it gently.

She loved the fucking she was getting from Willy, but it was Jimmy's teeth biting her nipple that sent Aggie over the edge. Her whole body stiffened. Her head pushed back against the pillow. The cords in her neck stood out. And she let out a wail that probably woke the neighbors.

"OOOOOHHHHMYYFUUCKKINNGGGODDD!!!

The feeling was almost too intense. So much of her being touched and loved. The strange newness of a new lover. The pleasure she was giving her husband whose cock was so hard in her hand. Aggie Clark felt all this as she came and came and came.

The men continued to caress her through her orgasm and as it subsided. Willy remained hard inside her womb. Jimmy nibbled her breasts, eventually working his way up her neck to kiss her full on the mouth. Their tongues probed gently at each other.

Aggie finally broke the kiss and, holding Jimmy to her bosom, looked at Willy.

"I want my husband to fuck me now, Willy"