The Wig Ch. 2

Story Info
Cindy meets her sister's boss.
2.1k words
4.39
109.9k
29

Part 2 of the 3 part series

Updated 10/30/2022
Created 09/26/2001
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"I'm worried about Candy honey," said Cindy into the phone. "I'm going to stay here until she shows up. I might not be home until morning."

"Just remember," said her husband Larry. "Don't give her any more money."

"I won't," replied Cindy hanging up the phone.

After fucking the stranger, Cindy had showered and changed back into her dress. She had returned the wig to it's pedestal. She had laid down in her sister's bed and napped for several hours she was so exhausted from getting the fucking off her life from her sister's drug dealer.

As the hours passed, she became more worried about her sister's whereabouts. The stranger had told her to be at Big Jim's tonight, maybe her sister would show up there?

Cindy rummaged around for a phone book, but couldn't find one. Finally, she called information and asked for an establishment called "Big Jim's." There was one and it had a local number. She called the number, a man answered and she could hear music blaring in the background. Probably a bar, she thought as the man gave her the address.

The address wasn't far from her sister's apartment. It was still in the seedy section of town and Cindy couldn't afford to be seen there so she returned to her sister's bureau and put on the wig. The wig didn't go with her elegant attire so she began rummaging through her sister's clothes, selecting heels, a mini skirt, and a white halter. Things she would ever wear in public without the wig to disguise her. When she put the clothes on, she couldn't believe how much like her sister she looked.

Cindy decided to take a taxi. The driver knew right where Big Jim's was and dropped her off in an alley. She paid him and got out of the cab.

There was a door in the alley that she tried to open, but it was locked. This must be the back entrance to the bar. She was just about to go out on the street to find the main entrance when a voice said, "Whatsa a matter, forgot your key?"

Cindy looked behind her and was surprised to see a pretty young girl pulling a key out of her purse. The girl was dressed similar to herself, kind of a cross between sexy and slutty. She had large breasts like Cindy's, but they were a little too perky to be real.

"Where you been hanging out?" asked the girl as she unlocked the door.

"Around," said Cindy following her in to a dark hall.

"Well you've pissed off a lot of people around here including me," said the girl. "You've better go make things right with Big Jim."

"I'm sorry, I haven't been myself lately."

"Here then," said the girl, "take this." The girl handed her a pill and Cindy swallowed it dry, thinking it was just an aspirin.

The girl had pointed at door that had an office sign stuck to the top. 'Big Jim must be the manager,' thought Cindy. He might know where my sister is.

Cindy clenched her fist and knocked lightly. "Who the fuck is it?" yelled a voice from the office.

"It's Candy," said Cindy.

The door was yanked open and Cindy found herself staring at a greasy little Italian guy. He was probably her height, though she was taller in her heels. The man was probably about fifty with silver streaks in his hair. He had a slight paunch and his shirt was unbuttoned, revealing a very hairy chest and several large gold chains.

"Well, well, well," said Big Jim. "I didn't expect to see your face back here. I thought you ran off to one of the chain clubs." The man grabbed her shoulders and shook her violently. "You're costing me a fortune bitch," he said before pulling her into the office.

"I'm sorry," she said shaking him off. "I haven't been feeling very well."

"Well you do sound kind of funny," he said sitting down. "Tell you what slut, you owe me interest on the money you cost me." He spread his legs, "Time to make a payment."

"What do you mean?" she asked.

"Come suck my cock."

Cindy didn't like that idea too much, but for some reason the thought of blowing two strangers in one day had her pussy gushing.

"Come on slut we don't have all day," said Jim. "There's worse things I could make you do."

Cindy slowly walked towards the man. She was feeling funny again and she wondered what exactly was in the pill the other girl had given her. Her inhibitions were disappearing as she fell to her knees between the spread legs of Big Jim.

"I've been wanting this a long time Candy," said Jim.

Cindy nodded. An impressive bulge was growing under the man's slacks. Her hands were shaking as she unbuckled his belt and pulled it out through the loops. She then unbuttoned his pants and slowly pulled the zipper down.

The man raised his hips long enough for her to pull his pants down around his ankles. When she looked up the tip of a very long cock was sticking out of his briefs. Her eyes widened when she saw it and his briefs quickly joined his pants around his ankles.

His cock stood out proudly from his crotch. It was about ten inches long, even bigger then the man earlier, though Jim wasn't nearly as thick.

"What do you think? Big enough for you?"

"It's beautiful," she said staring at it. Before today, she had only seen her husband's little penis. Now she had seen three and she was starting to feel cheated. Why did she have to get stuck with the small one at home? Cindy grabbed the base. Her fingers barely touched as they encircled it. She brought her head forward and kissed the tip before licking around the head of the man's cock.

"Uppity bitch," said Jim. "Too good to give the boss a blow job. Never thought you'd be sucking my cock did you?"

"If I'd known it was this big," she replied I would have sucked it a long time ago." It jerked at the compliment just as she wrapped her lips around the head. She wondered what her sister would think when she showed up and the boss expected a blow job from her, not to mention her drug dealer wanting to fuck her again.

"Well your lips sure look good wrapped around my big dick," he said as he unbuttoned his shirt and pulled it off.

Cindy's lips were busy slurping on the head of his cock so she didn't answer, she just nodded, which resulted in her bobbing her head over several inches of cock and Big Jim groaned with delight.

She relaxed her throat and began swallowing his cock. The guy earlier had been good practice for her and she easily swallowed eight inches. Jim's ten inch cock provided her with a new challenge and with a little extra effort she pushed down until her nose touched his hairy crotch.

Cindy began bobbing her head rapidly up and down his cock. She tightened her lips and was rewarded by a big groan from Jim as he began bucking his hips, ramming his cock into her mouth.

She heard another groan of satisfaction and was surprised to find that it was coming from deep in her own throat. Why did she enjoy doing this base act? Why did she enjoy being treated like a whore? Why was her belly growling at the thought of swallowing his hot sperm?

"God damn I knew you would be good," said Jim grabbing the sides of her head and fucking her mouth. She felt the wig shift a little as he grabbed it, but it remained on.

Jim's cock was swelling rapidly and with a jerk that she felt deep in her throat he shot his first load directly into her belly. She wanted to taste it, so she pulled her head up and caught his second wad in her mouth, rolling his hot seed around on her tongue before swallowing it. When Jim was finished cumming, he pulled her to her feet and flicked up her halter top so that he could play with her breasts.

"That's odd, your aureola seem bigger then normal," said Jim just before he bent down and sucked a nipple into her mouth.

Cindy moaned and grabbed the back of his head as he sucked on her nipples. One skillful hand was working it's way under her skirt, pushing aside her panties, and fingering her slit until she started humping his hand.

Cindy moaned with frustration when he suddenly stood up and spun her around. Jim roughly forced her down over his desk, mashing her breasts against the wood and her ass was thrust up above her arched back. Cindy felt his cock pushing against her labia and with one powerful push, he thrust his entire cock deep into her pussy where no man had ever gone before. Cindy screamed as his cock triggered a large orgasm.

Jim held his cock buried in her pussy, moving it around slightly. "I''ve decided to collect another interest payment."

"Make me pay," she cried pushing her ass back into his cock. "I love your big cock. Fuck my pussy."

"I can fuck lots of pussys bitch," he said pulling his cock out. "I'm just lubricating my dick up so I can fuck your ass. Not many sluts can take it up the ass like you can."

Cindy's eyes opened wide and as she felt his cock sliding between her ass cheeks, she thought, 'Oh oh."

Cindy felt Jim slide his long cock down her crack until the head was touching her rectum. Never in her wildest dreams had she imagined people did this sort of thing. If she had she would have been thoroughly disgusted with the idea, now she wanted to do whatever would please Big Jim. As the head began pushing against her sphincter, she knew one thing, she was glad he wasn't as thick as the man who had fucked her earlier.

Her sphincter seemed reluctant at first, then it slowly opened for the invader. Cindy gritted her teeth and grabbed the edge of the desk as her ass hole stretched open to the point she thought it would rip apart, then thankfully slowly closed around the head of his cock.

"Gawd damn your tight," said Jim. "This is harder then I thought. You'd better hang on."

Big Jim put his hands on her cheeks and spread her wide open as he began pushing more of his cock in. Cindy had never felt so full and he was only half in. Jim continued his relentless advance deep into her ass and she was surprised to find that her ass was growing accustomed to his cock even before she felt his balls gently slap against her thighs as he buried it to the hilt.

She was breathing heavily from the pressure and Jim gave her a minute to get used to it. Jim began slowly withdrawing his cock until just the head was in, then he pushed it back in. He began a long leisurely fuck of her ass.

"This is the best ass fuck I ever had bitch," said Jim sighing with pleasure. "Your ass is gripping my cock like a vice. It's like your a virgin back here."

"I've never had a cock as big as yours before," said Cindy. She was starting to get into it, liking it even. The only draw back was that her pussy felt neglected.

"You like my big cock don't you?" asked Jim picking up speed.

"Yes, god yes," moaned Cindy. "I love your cock. Fuck my ass." She was squirming around his cock wishing she could get a hand between her legs to finger her pussy.

"Ugh ugh," she grunted. Jim was fucking her ass hard now. It seemed to last forever, probably because he had come earlier. Finally, Jim gave a hard thrust and she felt his cock spurt sperm deep into her ass. The cock spasmed and spit out another large wad and then a third. It was still oozing sperm as it began to shrivel in her ass and he slowly pulled it out.

With a loud smack, Jim brought his hand down on her ass cheek and said, "Hurry up and get changed. You only got a few minutes till your on."

Cindy sighed and stood up, feeling semen squish around in her ass. She didn't know what he was talking about, but she quickly got dressed. As she was heading out the door he called, "I'll be expecting another interest payment every day until you pay me back."

"No problem," she replied picturing the shock on her sister's face when she saw Big Jim again.

See part 3 where Cindy finds out what her sister does for a living.

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AnonymousAnonymousover 6 years ago
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another cocksucking WIMP posting dumb cuck SHIT.

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READ MORE OF THIS SERIES

The Wig Ch. 1 Previous Part
The Wig Series Info

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