The Challenge Ch. 02: Voyeurism Games

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Author’s note: This is another Challenge story. It’s kind of a sequel but not really. The events in the story are happening during the same time frame as the first Challenge story. You don’t have to read the first one, but it may help since they share a few of the same characters. I would suggest reading the first Challenge story, and then read this one. You’ll recognize some of the character cameos when they occur.

I wrote what turns me on. There is a LOT of voyeurism, big butts, a little bit of interracial and group sex, and one very manipulative, perverse old man.

Editing thanks go to Todger65.

2: Voyeurism Games

Chapter 1

Vernon parked his beat up, black Subaru Legacy in the side parking area of a long driveway. Getting out of his car, the 18 year old exhaled into the cold January weather, seeing his breath. Closing the door, he made his way inside the massive home of his employer, Bob.

Bob had called him to see if he could clear out some fallen branches following a recent ice storm. Vernon was happy to help. Usually he only made extra cash from doing yard work for Bob during the warmer months of the year. He genuinely liked the old man too, listening and laughing to his stories during breaks. Vernon felt he was paid way too much for simple yard work, but has been graciously helping out Bob since he was 14.

Making his way up the stairs leading to the front door, he saw a woman exit Bob’s house. She looked familiar but couldn’t place where he had seen her. She was gorgeous, with shoulder length, dirty blonde hair. Something was a bit off about her, she looked distressed. It was as though someone had just asked her to perform an unpleasant or difficult task – like seducing her son for a large sum of money perhaps.

Vernon nodded and smiled as they walked past each other. The woman surprised him by speaking up.

“Hi, you’re Vernon right?” The woman asked, attempting to hide whatever issue caused her to be distraught.

“Oh, um, yes ma’am.” Vernon replied.

“I thought you were. I’m Ray’s mom, Julie.” She said, offering a polite smile.

“Oh, oh yes, I remember now. I thought you looked familiar.”

“It’s ok, I don’t think you’ve seen me enough to recollect that. Anyway, how is your mom? I think I last spoke with her when I ran into her a month or so ago at the mall. I was doing some Christmas shopping.”

“She’s doing ok. A little busy lately.”

“Great.” The two women weren’t close, but friendly acquaintances who would carry on and chat for several minutes when they occasionally saw each other out or at high school events. “So you’re here to do some yard work? I thought you and Ray were at a sleep over last night at your friend’s house.”

“Yes ma’am. I left early to get started on clearing up some of the tree limbs here.”

“Ah, well try not to freeze out here,” Julie chuckled. “Anyway I better get going. Take care!”

Vernon nodded, smiling to Julie, turning to watch her make her way down the steps. Ray had a hot mom indeed. He wondered how she knew Bob or why she was there, but forgot about his curiosity within minutes.

Vernon made his way into the vestibule of Bob’s large home. He was greeted by the old, jolly-looking man. He had a small white beard that made Vernon think of Santa Claus – if he were on vacation that is.

“Hey pal! Come on in!” Bob greeted Vernon as he entered his home. He always seemed to be in a good mood.

“Good morning, sir.” Vernon smiled back, shaking Bob’s extended hand. “I don’t normally see you during the winter.”

“I know, I know! This crazy weather eh? Anyway, follow me and I’ll show you what I’d like you to clean up,” Bob explained, motioning for Vernon to follow him.

After Bob briefly explained where he wanted the fallen limbs and debris put he told Vernon to join him inside when he had finished, for a chat and perhaps some hot chocolate. Vernon, slightly confused and curious, agreed and went about his way, cleaning up a small section of Bob’s large backyard.

Forty-five minutes later, Vernon found himself sitting in Bob’s office, waiting for his hot chocolate to cool.

“There you go, pal.” Bob entered the room, handing Vernon a 20 dollar bill. “Not bad for 40 minutes of moving some dead limbs around eh?”

“Heh, no sir. Thank you.” Vernon chuckled and replied.

“No thank you! Anyway, I wanted to chat with you about the possibility of earning some extra money that doesn’t involve yard work.”

“Oh, ok, well that sounds great sir.”

“You just had a birthday recently didn’t you?” Bob asked, sitting back in his chair.

“Yes, I turned 18 last week.”

“Ha! I knew it was in January. I may be old, but I’m not senile yet!”

Vernon chuckled again, “No sir.”

There was a brief pause, while Vernon sipped his hot chocolate. “So the extra money. Since you’re an adult now, I will speak to you as one.” Bob said standing and walking to his bookshelf. He rummaged through some magazines, finding the one he was bahis firmaları looking for, then plopped it on his desk in front of Vernon before sitting back down. It was a magazine called “Elite” and had a picture of a souped up Mustang on the cover. It had custom rims and a custom paint job.

“You’re familiar with that magazine aren’t you?” Bob asked. Vernon nodded, looking toward the old man across from him.

“Magazines are usually marketed toward demographics. Old ladies, teenage guys like you, do-it-yourself house repairers, film buffs, teeny bop music lovers, and then guys that like technology, computers, new gadgets, and so on – guys like me to be honest.” Bob explained.

“That magazine is marketed toward African-American males in the 18-35 age brackets. It covers music, movies, sports and athletes, cars, and women that marketing surveys and research have deduced black men may like. Now, is there truth in it or is it a stereotype? I don’t know and I don’t care.” Bob explained, reaching across to grab the magazine, casually flipping through its pages.

“I recently sold the publishing company that publishes this magazine and a slew of others – marketed to many different demographics. It’s one of several companies I owned,” Bob continued slowly, flipping through the pages.

“There’s usually a section in the magazine –and I’ll find it in a minute – that features a few photos of lovely women; women in bikinis posing with cars, or bikes, or on the beach and so on. There’s one gal that has caught my eye. She’s a local model that’s been featured in a few photos over the past four or five years. I know she’s only doing this modeling work on the side. She’s one of these girls that supposedly black men like; curvy, voluptuous, thick in certain places, if you know what I’m referring to. Ah there she is.” Bob found the page, admiring the model he was looking at. He glanced to Vernon sitting across from him.

“Hmm, the same blue eyes.” Bob said to a now very confused, but curious, Vernon. He managed a weak smile and kept listening to the old man.

“This particular woman is one I’d love to get to know more intimately. She’s gorgeous,” Bob said, turning his head looking at an image of this woman in the magazine.

“I know I could easily invite her over, or take her out to a nice dinner. But that’s boring. Where’s the fun? Where’s the thrill in that? I’d rather play games. I’m old; it keeps me on my toes and entertains me. I like to have fun! I see something I want, I don’t want to just swoop in and take it, I want to cherish the chase, and savor the meal before I eat it.” He looked to Vernon’s awkward smile.

“Ok, so I’m not sure what you want me to do. I’m a little confused.” Vernon said.

Bob chuckled, sliding the open magazine back over to Vernon. A curvaceous, buxom blonde, in a tiny bikini and red high heels was facing him. She had her hands on her flared hips and was standing in front of a cool looking street bike; one that was most likely used in racing events. Vernon looked down at the picture on the page, still confused, furrowed his forehead and shook his head.

Looking back up at Bob, Vernon asked, “You want me to introduce you to my mom?”

Chapter 2

Vernon sat in Bob’s office with a confused look on his face. He thought about his situation, “Why would he pay me to introduce him to my mom? Didn’t they already sort of know each other since she’s posed for pictures in his magazines? Maybe they didn’t, maybe big shots like him didn’t have anything to do with most of his employees.”

Before Vernon could asked the questions running through his mind out loud, Bob spoke up. “Introduce me to her? Well, somewhat, but not in the manner you’re probably thinking.”

“Alright, what does the earning extra money have to do with this?” Vernon asked.

Bob chuckled, standing to walk to his window. “I told you I like to play games. I like to have fun. I don’t want to just meet your mother, I’d rather observe her, watch her, I’d rather smell my meal, taking in its scent before I,” he paused turning back to face Vernon, “devour it.”

Vernon felt a little uncomfortable when he heard Bob say “devour it.” He may not be very experienced with the ladies, but immediately caught on to any accidental or intentional innuendo. Bob made his way to the edge of his desk, sitting next to Vernon. “I’m willing you pay you handsomely for a series of tasks that I ask you to do. Think of them as challenges. It’ll be a little game we can play. At first these challenges will be somewhat small, and in time, their difficulty will increase.”

“Alright, what does this have to do with her?” Vernon asked, nodding in the direction of the open magazine.

“Good question,” Bob resumed sitting across from Vernon in his large chair. “I’ll get straight to it. Your first challenge is to obtain video footage of your mother nude.”

“What?!? Are you joking?”

“No I’m not. I’m not joking at all. I want you to film her changing out of her clothes and into new ones, kaçak iddaa or perhaps stripping to take a shower, and so on. I will pay you $1000 for this footage.” Bob explained.

Vernon’s mouth hung open. There was a long pause before he spoke up, “I don’t even know how I’d go about getting that footage. I mean, what do you want me to do? Hide in her closet or under the bed or something? She’d kill me if she caught me!”

Bob shrugged, “That’s up to you.” He reached into his top desk draw pulling out a small box and then handed it to Vernon. “Here, use that.”

Vernon opened it to reveal an iPhone 5. “I’m sure you can figure out how to take video footage with that can’t you?” Bob said, winking at the teenager.

“So 1000 bucks for some footage of her nude; that’s the first challenge in this little series of ours. Think you can handle that?”

Vernon thought for a moment, feeling uneasy about what Bob was asking him to do. “I don’t know, that’s invading her privacy. I don’t really want to see her naked. I guess I could film it and look away, but still, it just doesn’t seem right. She might catch me.”

“Right. Well I tell you what, take that iPhone with you, it’s all yours. If you get an opportunity to take footage of her nude, then do so. If not, then don’t. Or if you decide would rather not do any of this, keep the iPhone anyway and I’ll see you in the Spring to mow my lawn.”

Vernon sighed, looking down to the phone. He put it back in its box and stood. “I guess I could try to. This isn’t a joke or anything is it? Why can’t you just come by the house for dinner or something?”

“What’s the fun in that?” Bob countered. “I’m a perverted old fool who wants to have some fun.”

“Alright, I’ll see what I can do.”

He said goodbye to Bob, confused and shocked, he left the house and headed home. He thought about how a $1000 would be nice. He wondered if it would be enough to get the rattling noise in his mother’s car checked out and repaired. He hated the idea of spying on his mom though. It all felt so weird and deceitful.

Vernon pulled into the driveway of his small home and sat in his car, pondering his options. “I could just hide in her big closet with the door cracked. She’d be putting on pajamas tonight. How would I sneak into her room if she’s going to go change though? I’d have to beat her there, which wouldn’t be possible without her being suspicious. She’d see me go into her room. Maybe I could try adjusting the window shade so I could see into the room from outside. ” He sighed again, realizing that might be the best strategy.

“I’d be a peeping tom on my own poor mother. What a jerk I’d be. I guess I’ll hold up the phone to the window and try not to look directly at her. It’s worth a shot and it’s for 1000 big ones.”

Chapter 3

Vernon sat in his room a little later, continuing to strategize. He’d wait for his mom to leave the house to go grocery shopping – something she does every Saturday, and sometimes on Sunday afternoon – then he’d run some tests by making sure the drapes to her bedroom window were slightly cracked and afforded him a view inside the room from outside. He would crouch in front of the window, holding the iPhone, and then attempt to capture footage of her naked. He wouldn’t look directly at her, but sort of glance to the screen to make sure he was facing the phone where it needed to face in order to capture something on video.

“Hi Vernie,” His mother, Nicole cheerfully said, startling from his trance. She was standing in his door way, smiling at him. Vernon hated his name, but never minded that his mother called him “Vernie.” Perhaps, he thought, she liked it better than “Vernon” – the name of a grandfather that died before he was born.

“Oh hey mom,” Glancing toward her he nodded his head slightly.

“Have a fun time at the sleepover?”

“Yeah it was ok.” Vernon diverted his eyes to his desk, standing to pretend he was going to organize some school papers.

“Good! How was the yard work this morning? Hope you didn’t freeze anything important off,” Nicole joked, now standing behind him, wrapping her arms around his torso for a warm hug.

“Heh, nah I didn’t.” He wanted to turn around and hug her, but felt shame for something he hadn’t done yet.

“You alright?” his mother asked.

“Yeah I think I’ll just take a nap,” he replied, moving away from her, ending her embrace from behind, sitting on his mattress. He yawned and stretched his arms a bit. It was for show and he realized it probably looked fake. However, he was legitimately tired and would take a nap, but not until after his preparations were complete.

“Ok, I think that’s a good idea.” Nicole told her son, directly in front of him, messing up his blonde hair. He jerked his head to the side a little, to avoid her fingers. She chuckled and bent slightly to hug him. She was only 5’2″ so she didn’t have to bend far to let her arms drape around his shoulders, pushing his head into her t-shirt covered abdomen. “Come on, you aren’t kaçak bahis too tired to hug back!”

Vernon sighed, hoisting his arms up, in his seated position, letting them land on her wide hips. His hands rested at the small of her back, right above the meaty swell of her massively muscular backside. He thought about the magazine images he saw earlier, thinking that there’s a chance he may see her naked later. He pushed those thoughts of his head. She ended the hug. Vernon let his hands drop, his fingers slightly grazing a pajama pants covered butt cheek. He instantly blushed. Nicole messed up his hair again, not noticing it, apparently.

“I love you Vernie, take a nice long nap. That’s really sweet of you to help Bob out.” Nicole called out to him as she left his room.

Vernon sighed, shaking his head, he thought, “You won’t think I’m that sweet if you knew what I agreed to do for some extra money.”

About 15 minutes later, his mother pulled out of their driveway, her car making the same rattling noise it had been for the last few weeks.

Vernon immediately headed toward his mother’s bedroom and checked out her window situation. He pulled the drapes apart maybe three inches. He used his new iPhone as a reference. He pulled them back a little more, thinking that four inches or so should be enough to allow him to capture footage from outside. Her room wasn’t all that big. She would mostly likely be in his phone’s field of vision. He wondered if the open drapes were too noticeable. Sunlight was creeping in through them, but he was going to wait until night time to try this. Perhaps she wouldn’t notice the drapes allowing more sunlight to creep because she would be in there at night. The only problem he may run into is the drapes being closed again by her. He tried to recall if she ever messed with drapes at all. He knew that she usually got up in the morning before the sun rises. So since she didn’t sleep late, perhaps she would have no need to double check if they were closed all the way or not. He did that in his room so he could sleep a little later without sunlight waking him, but only on Saturday and Sundays. His mother got up went to the gym almost daily, arriving back at home as the sun was rising.

Vernon left her room, grabbed his coat, put on some shoes and headed outside. The window to her bedroom was on front of the house, to the right of the front door. There was a small row of bushes that had lost their leaves for the winter in front of it. Luckily there was roughly an 18 inch gap between the bushes and the window. Vernon could easily slide his thin frame back there. Crouching may be an issue, but if he discovered that twisting his body would allow him to hide in that gap without banging up against the bushes and possibly making noise. Looking to his feet he saw dead leaves from the shrubs and promptly cleared as much of those out as possible. He didn’t want the crunching of dead leaves to alert her to a peeping tom outside her window. “Someone like me,” he sighed again, attempting to not focus on the guilt.

With the leaves cleared out of the gap, save for a small amount of leaves right next to the front steps which he could easily hop over – Vernon didn’t want his mother to notice leaves had been cleared back there – he went inside and took a nap. He was exhausted, having spent most the night playing video games with his friends at the sleep over.

Chapter 4

Vernon imagined himself keeping a journal of his attempts at completing this challenge. He never would of course, but he imagined the spreadsheet or word document would like similar to this:

Night 1 – first attempt to video her nude, failure. Light was off in her room or she changed in bathroom

Night 2 – 2nd attempt, failure. Light was on in room, didn’t see her.

Night3 – 3rd attempt, see above.

Night4 – saw clothing land on bed, nothing else. Failure.

Night5 – same as second attempt

Night6 – same as 4th attempt except saw shadow movement in her room.

Vernon laughed at his poor luck. He was able to perfectly sneak outside and crouch in front of her window without making a sound or being detected. He made sure to spend more time with his mother so he could be fully aware of her going to bed, or going to her room to change. They would sit and chat or watch TV or a movie together. The guilt slowly went away and he thoroughly enjoyed spending time with her. He would listen as she talked about her job as a police officer.

“So, since you’re the only lady on the crew, have any of the dudes tried to, you know, flirt or uh, get with you?” Vernon asked his mother, sitting on the couch with his arm around as she curled up into his side. The past few days found her at his side, happily snuggling with him.

Nicole let out a loud laugh, “No! Well actually.”

“Actually? What happened mom?” Vernon asked with a bit of concern in his voice.

“Oh it was nothing. It was several months ago. There was one guy that, well, he had a habit of grabbing my butt.”


“Yeah, it wasn’t too big a deal to me. It’s just a butt, you know?”

Vernon nodded, attempting to smile, wondering if he’d ever earn that $1000 by capturing her butt on video, “Uh yeah.”

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