Cindy's Last Striptease Ch. 03

"They left the company after we went bankrupt," Vic said.

"Well," Cindy grunted, "who are your partners now?"

Vic paused, and said, "there are none. I run Skinema now." He walked away, leaving the door ajar.

Cindy cursed. Vic clearly didn't want it known that he was the sole shot-caller at Skinema now, and Cindy had no one to blame for the avalanche of stipulations being laid upon her but him. Once he'd left out the back door, Alyson entered the bathroom, carrying a white robe.

"Cindy? Here's a robe for you when you're finished. I'll be upstairs picking out your outfit."

Alyson laid the robe on the bathroom counter. Cindy nodded in thanks, and Alyson shut the door behind her.

* * * * *

Claire didn't know for sure if she even wanted to talk to Derek today. She'd been ignoring his text messages all morning, most of them wanting to confirm their scheduled hookup at her home that day. Her plan to stay home from school had failed, and now that she was back in the hellish wasteland known as Taylor High School, she remembered why she'd considered bailing on him on the first place. She needed to hear only one "hey, it's Cream Pie Claire!" from a passing student in the hallway before she'd made up her mind. Derek would not be getting any pussy today.

Derek meanwhile, hadn't yet heard the rumors that he'd supposedly ejaculated in his girlfriend's panties, and had assumed her lack of replies was due to a non-working phone, and skated by the Wingrove home at quarter to nine like they had planned. He skidded his skateboard under the hedges lining the Wingrove's driveway, and hopped onto the front porch and rang the doorbell.

When Claire didn't answer the door, he knocked. No one came to the door.

It wasn't like her to avoid him like this. She had no reason to be mad at him. Wanting to exhaust all options, Derek turned the doorknob. To his surprise, the door was unlocked. He walked inside.

The house appeared to be empty.

"Claire?" he called out. He heard nothing.

He peeked in the living room and saw several large cases siting unattended. They looked to be lighting kits that a professional film crew would use. He shrugged. They hadn't been there the last time he was in the house.

Derek crept up the stairs and walked to Claire's bedroom.

"Claire?" he called again. Her room was empty.

He could hear talking and commotion coming from outside. He walked into the master bedroom and peeked out the back window.

There, in the middle of the backyard, was a shiny blue Corvette Stingray parked on the grass. Nearby was what appeared to be a film crew setting up a camera and light reflectors. He spotted Claire's mother, wearing a white bathrobe, talking to one of the crew members. He saw no sign of Claire anywhere.

Confused, he crept out of the bedroom. His walking was interrupted by the sound of a toilet flush, and someone emerging from the nearby bathroom. A short blonde girl, not much older than he was, stepped out of the bathroom and looked at him. She saw the confusion on his face and apologized.

"I'm sorry!" Kayleigh said. "I heard you ring the bell, but I was in the bathroom. You're the masseur, right?"

He froze in place. He wasn't sure whether to run or explain who he was.

"Yeah," Derek said. "That's me."

He slapped himself, internally, when he realized what he was doing.

"I'll let her know."

Before Derek could react, Kayleigh opened the bedroom window.

"Cindy! Time for your massage!" she called out.

Derek took a step backwards, but was too frightened to move any further. He hadn't had time to think before Claire's mother had come up the stairs and into the bedroom.

"Wow! Vic wasn't kidding. You are young!" was all she said when she saw him.

At that moment, Derek thanked himself for deciding not to take up Claire's offer to meet her parents the week before. He wasn't sure he would ever do so now.

Kayleigh walked out of the bedroom and shut the door behind her.

"So," Cindy began, "I hope Vic told you that I've had an anal massage before, and I like it done my way. I'll provide the gloves and oil, okay?"

Derek swallowed.

"Yeah. He told me that."

Derek watched her retrieve a pair of rubber gloves and a jar of organic extra virgin coconut oil from her dresser drawer. He wondered if she was wearing anything underneath her robe, and how much of her he might see when she removed it. He stared at her long legs, from the floor all the way up under her robe, and his heart pounded at the thought of where those stunning legs led.

She handed him the gloves and oil.

"This is the only stuff that works for me. Go ahead and do your thing."

He would have turned around if she'd asked, but Cindy didn't give him a chance. Before he could say a word, she removed her robe, and the answer of whether she was wearing anything underneath was answered. Derek could see all of her, every inch of her body, and she showed not a shred of modesty as she stood naked in front of her daughter's boyfriend.

Derek stopped cold, and stared at the gorgeous woman's body, dumbfounded. He was not expecting a woman her age to have breasts as large and perky as hers, or legs and abs so firm and toned. His penis swelled as he studied her delicate curves while she folded the robe and laid it onto her dresser.

Cindy was used to being naked around men, and the thought of covering any part of herself in front of him hadn't even occurred to her. She simply crawled across the bed and laid face down, and folded her arms under her face.

"Break me in slowly, please," Cindy said. "I haven't had anything in there in over twenty years. Today I'm doing my first anal scene and I want to be ready."

Derek's eyes went wide. Finally, it made sense.

Holy shit, he thought to himself. Holy shit, I'm on a porn set. Claire's mom does porn! And she thinks I'm her asshole masseur! Calm down, Derek, calm down!

His hands were shaking as he slipped on the rubber gloves, and opened up the jar of coconut oil. He stuck his index finger into the gooey white oil and stirred it.

"So, uh, does your family know you do this?" he asked. He wondered briefly if Claire knew about her mother's adult film career. If so, he could understand why she wouldn't tell him.

"No. Not even my husband. I quit the industry twenty years ago. Damn contract I signed forced me to come back. I pray to God they never find out."

"Well, uh, your secret's safe with me," Derek said. He walked to the side of the bed with a glob of oil on the tip of his gloved finger.

He stared down at her bottom, and damn, she had a nice ass! He could see where Claire had gotten hers. Derek remembered popping Claire's cherry on her bed in just the other room a few weeks earlier. Claire had ridden him reverse cowgirl style and he'd gotten a nice close-up look at the teen girl's round cheeks and the tight little hole between them every time she bounced. He wondered if her mother's hole was as sexy as hers.

Derek used his middle, ring, and pinky fingers on each hand to pull Cindy's butt cheeks apart, took a peek between them and confirmed that yes, mother's anus was indeed just as tight and sexy as her daughter's. Tight, pink, and clean.

He plunged his slippery index finger into Cindy's rear hole, and he felt her body go tense. She gasped, and her sphincter muscles constricted around his finger.

"Sorry!" she said. "I'm just not used to this. Give me a moment."

"It's okay."

Slowly, she let out her breath, and her sphincter relaxed. Feeling his finger go free, he twisted it around in a corkscrew motion.

"Gently, gently!" Cindy corrected.

"Sorry about that," Derek said.

Gently, he turned his finger, softly applying pressure to her anal muscles.

"That's it," Cindy said softly. "Just like that."

Derek carefully twisted his finger the way she liked, before slowly pulling it out and sliding it in again.

"This okay?" Derek asked.

Cindy waited a moment to answer.

"It's just fine," she said. "Just do it gradually. I'm not used to this."

"Not a problem."

The doorbell rang, and Cindy and Derek both went still.

"Ah, dang it. Who could that be?" Cindy asked.

Derek's heart raced. He knew exactly who it was.

Hearing the doorbell from outside, Alyson hurried into the house through the back door and made her way to the front. She peeked out the window, and upon seeing a familiar face, opened the front door.

"Hi Lonny! What are you doing here?" she asked.

"I'm here for the massage, girl! Where's the lucky starlet?" the masseur asked.

Alyson looked at him, confused.

"She's already upstairs with someone."

Lonny tsked.

"Are you kidding me right now? He double-booked me again?"

"Looks like it," Alyson said, wincing.

"Well, you tell Vic that he and I are square now!"

With that, Lonny huffed and stomped off the front porch. Alyson closed the front door.

Upstairs, Derek waited ten seconds before speaking.

"Whoever that was, it sounds like they're gone now."

"Thank God," Cindy said. "Yesterday my neighbor rang my doorbell while I was mid-coitus. Can't believe Vic's making me film in my own house. I'll never forgive him for this."

Derek silently praised his good fortune as he kept sliding his finger in and out of his girlfriend's mother's anus. When her breathing became slower and steadier, he worked up the pressure a bit higher.

"Ooh, you're good at this," Cindy said, flexing her legs. She arched her bottom, so that Derek could slip his finger in deeper.

"Thanks," he said. "Um, do you think you can handle another finger?"

Cindy thought for a moment.

"I think you'd better. This actor they've got me with- he's got, he's got- a nine-inch cock."

Derek chuckled to himself.

"Which, between you and me, I'm not complaining. Yesterday he fucked me so hard I could barely walk. Wish my husband could do that."

Derek smirked, and suppressed a laugh. He looked at the framed photo of Stuart resting on the nearby dresser and thought to himself, chump.

"Your husband, is he, uh, a principal or something?" Even before meeting Claire, Derek had recognized the tie-wearing, curly-haired dork from his childhood.

"Sure is. Green Meadow Elementary."

"I thought he looked familiar," Derek said. He remembered throwing rotten apples at his Honda several years earlier.

"He might look even more familiar in a few months. He's running for mayor. Can you believe it?" Cindy said with disgust.

"Mayor? And his wife does porn?"

Cindy sighed.

"He just told me yesterday. Apparently he's been thinking about it for awhile. This could ruin my chance of keeping my past out of the public light. I wish he hadn't been so thoughtless. He knew I used to be a burlesque dancer, too. It's his own fault really, if this blows up in his face."

Derek chuckled. "Well, maybe. I hope everything works out, Mrs. Wingrove."

He crossed his index and middle fingers, and slid them both into her anus at once. Cindy sighed deeply. He twisted his wrist to the left and right and kneaded her tight sphincter muscles.

Cindy let out a long sigh, and as she gradually relaxed her muscles, another confession escaped from her lips.

"Today, Vic wants Simon to fuck me in the ass in my husband's Corvette. And to be honest with you, I'm looking the hell forward to it."

Derek suppressed another giggle and continued twisting his fingers between her tight cheeks.

Cindy moaned. "I just, I just wanted to be a good example to my children. And look at me now. Look at me."

"You don't look so bad to me," Derek said. He let his eyes wander up and down Cindy's naked body.

"I just hope my daughter stays a virgin until marriage. I don't want her to end up like me."

Derek bit his lips hard, trying to keep a straight face.

"I'm sure she will be," he said assuringly. He looked at the framed family photo on the wall. "She looks like a very- uh, proper and well-behaved young lady."

He hoped he sounded like a mature adult with that phrasing.

"She's a bit of a trouble-maker that one. I've caught her taking nudes to sext to boys at her school."

"That one? I'm shocked! Children these days. They grow up so fast." Derek clucked his tongue three times.

Truthfully, Derek had seen some of those photos, including some that weren't meant for him.

"And this morning, I had to drive her to school because she wouldn't get ready. I think she was deliberately trying to miss the bus!"

"Really?" Derek asked. "But you did get her to school?"

"Well, yes," Cindy said.

That was news to Derek. He wasn't sure where Claire was today.

He continued kneading Cindy's anus until his fingers were able to comfortably slide inside with minimal squirming from his patient.

"Well, ready for three fingers?" he asked.

Cindy lifted her pelvis off the bed and pulled her knees forward, so her bottom was pointed straight up in the air.

"Go for it. Get me ready for that thundercock," she said, giggling.

Derek scooped some more coconut oil onto his fingers and buried them into Cindy's anus. She seethed briefly, but let out a sigh once Derek started working her.

"Oh, that's where it's at," she said softly. She relaxed and let him work his fingers inside her. "You know, I used to take it in the ass all the time when I was a burlesque dancer."

"Really?" Derek asked. "I'd love to hear more about that."

"I was such a slut!" she said, giggling.

"Wouldn't have guessed." He meant that. His first impression of Claire's mother was the complete opposite as that of the woman whose butt hole he was penetrating now.

Cindy regaled to him a memory she had about a night that Nocturnal Desires had hosted a bachelor party. The guests had showed up with the groom wearing a blindfold, and upon realizing where his buddies had brought him, he insisted that he would not be partaking in any activity that might violate his upcoming wedding vows.

Of course, the guys had paid the dancers generously to entice and tease the hapless groom until he succumbed to their temptations. Sexy Cindy took turns with another girl sitting on his lap and flirting with him relentlessly, encouraging him as he fondled their bodies, yet he'd declined every invitation they'd offered him to join them upstairs. It wasn't until Cindy had whispered three magic words in his ear, I do anal, that Faithful Freddie agreed to accompany his temptress to the VIP suite.

As it happened, the other twelve party guests wanted in on the action, and Cindy was the only girl working that night who offered back door access. She spent the remainder of the six-hour party on all fours taking dick in the ass- one, after another, after another. Her very first date with Stuart was the following night, and her bottom was excruciatingly sore the entire evening.

"And he wanted anal too, right?" Derek asked, smirking.

"Oh, no, not Stu. The guy's a puritan," Cindy corrected. "Thank God, I couldn't have taken any more for a week." Cindy reckoned she might feel the same after today's shoot.

Derek continued fingering her, working her firmly but delicately, and listening to her sighs to guide his intensity. It was surprisingly enjoyable getting inside a woman's ass this way. He decided to try it with some other girls sometime. He wondered if Claire might be down for a good butt hole fingering. He was willing to bet that the inside of his girlfriend's tight little ass felt amazing.

He kneaded her for several more minutes, enjoying the soft moans and sighs she let out whenever he rubbed her just the right way.

"Ooh, I really needed this. Thank you, Lonny," Cindy said.

"My pleasure," Derek replied. He then froze, realizing his tone and phrasing sounded a bit too excited.

There was a knock at the bedroom door.

"Uh, who is it?" Derek called.

"Cindy? Vic says your massage is over," Alyson said. "He wants to see you in your wardrobe."

Cindy turned her head to look at Derek.

"Over already?" the faux masseur asked. "Hope you're ready for that thundercock!"

Cindy laughed.

"My fanny's been through worse. I'll manage." She turned to the door. "Come on in, Alyson. You've seen me naked before."

Alyson opened the bedroom door and entered carrying a number of outfits for her. She lowered her eyes to avert her gaze away from Cindy's bottom. Derek removed his fingers from between the housewife's buttocks and peeled off his gloves.

"I'll just get going, I guess," the high-schooler said, awkwardly.

He casually excused himself from the bedroom and hurried out of the house. He pumped his fist in celebration the moment he stepped out onto the front porch, and swiped his skateboard out from under the hedges. He winked at Alyson, who watched him from the upstairs window quizzically as he hopped onto his skateboard and glided down the sidewalk.

* * * * *

Cindy tried on a number of her swimsuits, including the bikini she wore on her trip to Hawaii the previous spring. She modeled each one for Alyson, who shook her head in disapproval.

"Too tame. We need to get you into something naughtier."

"This is all I've got. Soccer moms don't have many 'naughty' clothes."

Alyson searched through her wardrobe case. She fished out a tiny black thong.

"Try this on," she said.

Cindy took the skimpy swimsuit and slid her legs through the holes. She pulled it up over her hips and turned to show her behind to the wardrobe girl.

"Looks good!" Alyson remarked. She gave Cindy's bottom a playful smack, making her firm cheeks give a slight jiggle.

"What about the top? None of the bras you had fit me."

"That could be a problem," Alyson said. She examined the matching top for the thong Cindy had on, then lowered it. "Tell you what... do you have any white t-shirts?"

"Yeah, a few."

"Go grab the smallest one, please."

Cindy went to her closet and sorted through her many shirts hanging inside. She fished out every white t-shirt and laid them on the bed. Alyson looked through them and picked out the smallest.

"Ooh, this one's been through the wash a lot!" Cindy remarked, and pulled the shrunken t-shirt over her head.

Alyson examined her front and back side, and got an idea. She lifted the hem up to reveal Cindy's belly, and pulled the material back, making the shirt hug the contours of the homemaker's breasts tightly. Alyson tied the extra material into a knot, converting the shirt into a makeshift crop top.

"Now THAT looks pretty sexy!" the wardrobe girl marveled.

Cindy examined herself in the mirror. She had to admit, she didn't look bad. She flexed her legs and admired her ass. She attempted to make her elbows touch behind her back, and noted that her nipples protruded through the front of her shirt very noticeably.

"I think you just need something for your bottom. Got any shorts?" Alyson asked.

Cindy looked through her closet and took out a pair of tan khakis.

"Oh, you'll need something a lot shorter than that! I'm thinking Daisy Dukes!"

"You'll have to check my daughter's closet for shorts like that!" Cindy said.

Alyson bit her lip nervously. As far as she knew, Cindy was still unaware that Claire's bedroom was exactly where her lingerie from Wednesday's shoot had come from.

"Cindy!" Bud called from downstairs. "We need you out here!"

"Go on out," Alyson said. "I'll work on something for you to wear."

Cindy made her way downstairs, and stepped out onto the back porch where the crew was set up.

"Woo! Lookin' good!" Vic marveled when he saw the blonde housewife step outside.

Cindy ran her fingers through her hair and modeled for the crew.

"All right Cindy, can you stand by the car, please?" Jeff asked.

Cindy stood next to her husband's Corvette, which was now parked in the middle of the yard. She glanced at the two neighboring yards. Indeed, fences blocked the view from both neighbors' houses, but it would not be difficult to peek over should either of her neighbors get curious about the noise.