The Challenge Ch. 02: Voyeurism Games

"So I let him. It was in good fun, he was otherwise a nice guy, and it never escalated. One evening the captain caught him red handed, or 'butt-handed' if you know what I mean," she playfully jabbed Vernon's side and then continued resting her head against his shoulder.

"Oh yeah? Then what happened?" Vernon asked.

Nicole sat up, "He was fired on the spot!" She kissed her son on the cheek and stood up to make her way to her bedroom. "Goodnight Vernie. Oh by the way, I've really enjoyed hanging out with you more this past week. You're my favorite person!"

He had to force the guilt caused by her comment away; he had a task to complete. This would be last night of attempting to film her naked. If he failed again, that was it. No more sneaking around and peeping in her room. He waited a few seconds before bolting off the couch, not bothering to put on a coat, and raced outside to the gap between her bedroom window and the shrubbery. He was in such a hurry he nearly left his phone on the kitchen table.

Quickly crouching down in the gap between the shrubs and his mother's bedroom window, he held his iPhone into position. Then he saw it. Rather, he saw her. She was still clothed and her back was to him, but he was finally able to see something. With her back to him, she slid off her sweatshirt, and unhooked her bra. He could see her large breasts sway as they were released from their prison. He shook his head hoping she wouldn't turn around, but knew she would. Then he watched as she slid her sweatpants down. He glanced away as her black thong was visible showing her meaty butt cheeks. Vernon wasn't looking directly at the phone, but he could tell in his peripheral vision that she was sliding her thong down. It's black color no longer on top of her skin. He glanced at his phone, briefly catching her muscular cheeks, and then as quickly as he glanced, he looked away to the side again. He saw more movement in his peripheral vision and then glanced at the phone again. He nearly gasped for air when he accidently saw her large breasts on display. She was unfolding some clothes she laid out on the bed and holding them up to her body, as if she were confirming their correct sizing.

A wave of guilt came over Vernon as he watched his mother hold what looked like a dress up to her body, covering her nudity. She folded the article of clothing, placing it on the bed, and picked up her cell phone. She was standing there nude again, checking texts or perhaps a missed call. Vernon glanced at her breasts again, and then quickly looked to the side. He saw movement again. She had turned around to place her phone on the bed side table. Another glance and he saw those marvelous glutes once more, another wave of guilt as he glanced away. He closed his eyes, shaking his head in disgust at himself, and then opening them to see nothing on his phone. The light in the room was off. He mother was either in bed, or in her bathroom with the door closed.

Moving back inside, Vernon went straight to his room, closing the door behind him. "I just made $1000," he said to himself, feeling less than joyous over his accomplishment. He felt guilt, but also something else that he couldn't quite put his finger on just yet.

Chapter 5

Vernon sat in Bob's home office again the next morning. Bob was uploading footage to his laptop. He had already watched it on the phone twice.

"This is great work, Vernon!"

"Thanks," he sighed.

Bob wrote and handed him a check for a thousand dollars. "Ready for the next challenge?"

"Next challenge?"

"Oh yes, we're not done here. There's more fun to be had here."

"Alright," Vernon replied, thinking maybe more nude footage or perhaps stealing some of her underwear to give to the old perverted Bob.

"I want video footage of her showering. I will give you $5000 for this."

"Showering?!? Are you serious?"

"Quite. You can sneak in her room or if the bathroom is large enough, hide in there, whatever you want."

Vernon thought for a moment that this challenge might actually be easier than his first one. His mother gets up at 4am most mornings. She goes to work out and is back home by 6 am. Vernon doesn't have to be up for school until 7 am. All he would have to do is be awake when she returns home from the gym, listen for the sound of her shower, and then go grab some footage – in theory. She has a glass shower stall so there's no shower curtain to deal with.

"Alright, sure." Vernon grunted.

"Excellent! The footage can be her getting into the shower, or shortly after she's already done so. I want the footage to show her entire shower session up until she turns the water off and if you can manage, until she wraps a towel around her." Bob explained.

Vernon shook his head as more guilt overcame him for something he hadn't done yet. "Fine."

He missed his opportunity Monday morning because he overslept. That evening he prepared dinner for the two of them. He cooked spaghetti, as it was simple enough, and he knew she liked it.

"What do I owe the honor of this wonderful young man cooking for me?" Nicole playfully asked, hugging Vernon tightly. Resting his head on her shoulder, he glanced down to her large protruding, yoga pant covered butt. Visions of it popped into his head from the brief glance he had of it the other night. The reason for the dinner was his attempt to make himself feel better for his actions; but he couldn't tell her that.

"I don't know, just felt like helping out some." He replied.

"Well it is much appreciated," his mother replied, kissing him on the cheek as she made her way to their couch. She patted the couch cushion next to her, "sit."

Vernon did as he was told. Nicole rose to her knees on the cushion. Reaching behind her, she appeared to be pulling the tight yoga pants out of her buttcrack. Afterward, she moved Vernon's arm to the side and collapsed into him, wrapping her arms around him on the couch. He instinctively patted her back.

"Remember this weekend I'll be away. I have to go take some more pictures with the magazine, alright? So no crazy parties," his mother joked.

"Don't worry I won't." Vernon's plan was to actually take his mother's car to get the rattling issue fixed. He didn't mention that to her though.

They sat on the couch for another hour, chatting about random things. She asked her son about school work and if he was still trying to figure out his plans after high school. He asked her questions about her fitness routines and scary situations on the job. He almost forgot about his second attempt to capture her showering.

Vernon went to bed earlier than normal that night. He didn't want to oversleep again.

Five thirty am came quick, too quick. Vernon couldn't remember the last time he had gotten up that early. He was nearly asleep again when he heard his mother come home from the gym at around 5:45. His eyes shot open and listened for her shower to start. Around five minutes passed and he heard it. He quietly got out of bed, grabbed his phone, and snuck down the hallway to her room. Her bedroom door was cracked, but he could see light coming from her bathroom door perpendicular to it. He held his breath and slowly pushed her door open. Luckily it didn't creak or crack. He saw her bathroom door was completely open. Moving into her room, he crouched down on her carpeted floor some unknown reason. Feeling silly, he stood back up, inching his way to the bathroom door.

He heard something and froze. It was a sweet sound, one that almost made him smile if it wasn't for the perverted and shameful act he was attempting to do. His mother was casually humming to herself in the bathroom. It reminded him of when should would do that in the car with him in the morning when she took him to school. He felt like crap.

His thoughts were interrupted when he saw movement in the bathroom. Looking up to the large mirror on the wall Vernon could see his mother's reflection. She still had a top on, a white sports bra, but nothing else. He looked away when he saw her naked bottom. He then brought his phone up to capture footage. She turned around and slid her top off, the mirror reflecting everything perfectly. He glanced again at her gorgeous backside, but again looked away after a few seconds. He watched her test the water and hop into the shower, closing the glass door behind her. Every few seconds he would look to his phone and see his mother soap up her breasts, or scrub her stomach, or bend down to run soap over her thick, juicy, thighs. Each glance lasted a second longer. When she turned around and pressed her butt up against the glass door, Vernon caught himself staring, unable to look away from it.

Nicole turning off the water caused Vernon to come out of his trance. He stopped recording when she stepped out of the shower and closed the door behind her. He backed out of her room slowly, closing her door back to the way it was, then tip-toeing back to his room as quickly as he could. He'd done it. He lay there in bed for the next 30 minutes wide awake, replaying the image of her butt up against the glass in his head. He dared not watch the footage again, but somewhere inside him, he really, really wanted to.

By 6:15 am his mother was gone and he was alone. He ate some breakfast, went to school, and tried not to think about what he had done and seen. Unfortunately, her juicy ass danced throughout his mind for most of the day. On his way home he stopped by Bob's house.

"Wonderful! She's gorgeous!" Bob exclaimed while watching the footage after loading it to his laptop. Vernon sat across from him, looking downward.

"Mmm, lovely. Thank you so much. Here's the promised check of $5000, all for you pal!" Bob slid it across his desk.

"Ready for the next challenge? Good," Bob said, not giving Vernon a chance to answer.

"Masturbation. We all do it. Men and women alike. I will pay you $10,000 for video footage of this perfectly, shapely woman, pleasuring herself in whatever manner she loves most."

Vernon didn't move and didn't blink, staring blankly at Bob. After, what could've been 10 seconds of a blank stare, Vernon flatly asked, "What?"

"Mmhmm, I want a video of her masturbating." Bob reiterated nonchalantly.

"Um, what?"_

"Vernon, come on now, you're 18. Not an old man like me, certainly you heard me."

Vernon didn't know what to say, shaking his head, he gulped hard. "I, I, uh, I can't do that. That's, that's just, no way."

"I told you my little challenges would increase in difficulty each time didn't I? This will be an exciting escalation for me! You too."

Bob's voice lowered and a mischievous little smile came across his face, "Just imagine hiding in a closet or peeping around the corner at her, she'd never know!"

"But that's way too private an activity. That's too wrong. I can't disrespect her like that."

Bob paused a moment, "Isn't your mom's washer and dryer about to break any day now?"

"How did you –"

"I'm sure 10 grand would easily buy some new appliances right? I'm sure you could get a top of the line matching set for less than half that."

Vernon was speechless. How did this man know about the old clothes washer and dryer that his mom was having a difficult time with? Did she tell him? Did someone else? Vernon felt trapped.

"How did you know about that?" He asked, gritting his teeth.

"Heard it through the grapevine." Bob casually tossed that little nugget to Vernon.

Vernon remained silent. He wondered if his mother knew Bob better than she let on. He wondered if Bob was still active in the company he formerly owned; perhaps he had been chatting with someone about it. Vernon frowned in anger when he thought of another paranoid-induced possibility, but quickly reminded himself Bob had never been to his home – or so he thought.

Bob didn't know everything. He didn't know the refrigerator was just as old and struggled to keep food fresh for very long. He didn't know that his mother made squat as a police officer. He didn't know about her car issues.

Vernon stood and nodded his head. He slowly walked out of Bob's office, having no idea how he would ever manage to capture footage of his mother pleasuring herself. Changing in and out of clothes or taking a shower was one thing, but spying on someone while they masturbated was a much lower level of disrespect and perversion. Vernon knowing this and admitting to himself that he would attempt such a thing made his head hurt.

Chapter 6

The next 3 days were horrible for him. Vernon avoided his mother as best he could, he had trouble sleeping, and he had trouble eating. Nicole asked him if he felt bad, he lied saying he was tired. Depositing that $5000 check into the new savings account he set up didn't make him feel any better.

Saturday morning arrived and Vernon asked his mom if she needed a ride. He lied saying that he had some errands to run so he would gladly drop her off at the studio and come pick her up later that evening when she was done with the photo shoot. Smiling sweetly, she accepted his kind gesture. They chatted on the way there like nothing was wrong and Vernon felt slight relief from guilt. After Vernon dropped her off in his car, he sped back home and got in her car.

Six long, mind numbing, hours later his mother's car was finally finished. He barely paid attention to the mechanic as he droned on about which belt was loose, which bearing was missing, which gasket needed replacing. He wanted out of there, he was annoyed and miserable.

Vernon went home and got in his car again. He didn't want his mother to know he had spent nearly $500 on getting her car tuned up. She would demand to know where he got the money.

When he arrived at the nearby location to pick her up, he couldn't help but smile, noticing how jovial she was. He started feeling a little better, thinking that maybe she was happy to see him. When she grabbed his hand, trailing her fingers across it and talking about her day on the way home, he forgot about the newest challenge from Bob.

Later that evening, he heard a knock at his bedroom door. He had showered and was putting some socks on while sitting on his bed. "Come in."

"Hi there Vernie. I was thinking we could find a movie on TV to watch," his mother suggested.

"Yeah, that'd be great mom, I'd love that," Vernon replied. There was relief in his voice. He had decided in the shower that he didn't need to film her. No one was forcing him. He was done.

Nicole threw her arms around him, snuggling close on the couch, kissing his cheek. "Love my little Vernie," she said, resting her head on his shoulder. He raised his arm, placing it around his mother, holding her close to him on the couch.

The movie was quite boring and Vernon had trouble keeping his eyes open. Leaning his head back on the couch with a slight smile on his face, he ran his hand up and down his mother's side. She was so warm and soft in his arm. The guilt and anxiety slowly washed away. He smiled when he pictured her beautiful backside in the shower. He stirred when he felt her move to grab a pillow to place on his lap. Watching her stretch out on the couch and lay her head in his lap, he casually trailed his fingers across her hip. She was wearing more tight yoga pants. They were grey in color and hugged her butt tight, going into the crack.

Vernon was staring at her, unaware that he was salivating, and unaware that his cock was hard. He replayed footage of her nude ass in head, while his finger lightly trailed back and forth on her hip and thigh. She was oblivious as she rested her head on his lap, her eyes toward the movie.

"It's perfect," Vernon said to himself. His mother stirred and for an instant he thought she heard the voice in his head compliment her.

"Ok, well that movie was kinda bland wasn't it?" Nicole asked, sitting up and getting off the couch.

Standing a couple feet in front of him, facing away, she fumbled with the remote to turn off the TV. Vernon stared at her butt. His cock twitched as he watched her reach back to pull her yoga pants out of her asscrack.

"Alright, there we go. I'm heading to bed," she said, placing the remote on the coffee table. "I had another wonderful evening with you, but I'm exhausted. It was a long day."

Vernon flashed a goofy smile as she kissed his cheek, blushing as she headed to her bedroom. Without removing the smile from his face, he stood and made his way to his own bedroom. Closing the door behind him, he stripped naked, grabbed his phone, and proceed to watch the shower video three times. On the fourth time, he paused the footage right before her butt smashed up against the glass door. He had a perfect view of it in all its perfection; soaking and dripping wet from the shower.

He nearly passed out from the orgasm brought on by his own hand. "That's it, that's all this will amount too. No more," he thought. Sleep found him in a few minutes.

The next morning he felt well rested and energized. Vernon opened his eyes, reaching next to the bed for his phone; he watched the first footage of his mother undressing. He didn't glance away this time. Watching it twice, pausing on the ass shots, he stroked his cock to erection.

Wrapping a towel around his naked body, he headed to the bathroom, his phone still in his hand. He passed his mother in the hallway; she let out a playful whistle at his nearly nude body. Still smiling as he reached his bathroom, he closed the door behind him. He then continued stroking his cock as he navigated to the part of the first video where his mother turned around to face the window and then paused it. He stood admiring her nude, hourglass figure. "How often does she do it?" he asked himself.

A few minutes later he stood in the shower letting the warm water wash over him, idly stroking his cock. "Everyone does it," he said to himself, watching his hand grab and stroke his hard-on while images of her perfect body flashed his in head. "it's no big deal. It'll be $10,000."

Just before he ejaculated again, he pictured her smiling back at him while she drove two fingers into her waiting pussy. He had just convinced himself of undertaking the next challenge.

Chapter 7

The decision to attempt to capture his mother pleasuring herself was reversed and overturned several times during the next week. Waves of guilt flood him, followed by relief when Vernon again decided to not film it. Lying awake in bed at night, looking to his phone, he struggled, determined not to watch the footage he already had. Usually, though, he ended up watching it and jacking off shortly before going to sleep. One morning he tried to see her in the shower again, but he almost got caught when she walked out of the bathroom as she waited for the water to heat up.

One night he even slipped outside to see if he could see into her bedroom again. The light was on, but she wasn't in view. He felt like an idiot and went back inside, satisfying himself with the footage he already had.

He had to think; he had to come up with a plan to watch and film her masturbating. A week before Valentine's Day Vernon figured it out. It was so simple he felt even more stupid for not thinking of it sooner.

Pacing back and forth in his room, Vernon perfected his plan. He had to join his mother for another movie night in a few minutes. She really seemed to relish in the increased quality time they were spending with each other over the last few weeks. Vernon gestured with his hand as he talked to himself in his head. He rehearsed telling his mother a lie that may plant a seed. He practiced a few more lines, satisfied that his seed planting plan may work; he left his room to join her in the living room on the couch. He was excitedly nervous, but felt confident.

"Ah, those nice yoga pants again?" Vernon chuckled at his mother, watching her stand at the coffee table and flip through channels on the TV.