Darkest Before the Dawn Ch. 06

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He challenges his landlady's BF to a contest winner gets her.
9k words
4.41
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Part 6 of the 6 part series

Updated 06/08/2023
Created 01/20/2017
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Crepuscolo got off the bus near Dawn's house, she was his landlady, and also a... he didn't know the word? Webcam mistress? Online pornstar? He recently helped her with creating some content, and it went poorly, very poorly. Apparently all he needed was a brisk breeze to make him achieve orgasm.

He saw the house as he made his way up the street, his mind wandered to recent problems. That very day he was at the home of a classmate, Sabryna; and even had sex with her! It happened during a football game watched by her whole family, the two of them were able to do it without anyone noticing!

Crepuscolo turned the door knob, wondering how he was able to get up to so much mischief, and yet feel like shit.

A cold gust greeted him as he stepped thorough the doorway, stopping him instantly. Dawn turned to pornography because she was broke. The housing bubble did in her real estate business, leaving her destitute. Since then she kept her Florida home cool, but certainly not cold.

Next he heard faint voices in Spanish, causing concern to fill him. The sounds came from the backyard; moving slowly he went to find the source.

Looking through the sliding door, he saw two men dressed in dust covered plaid shirts and jeans. They were filling the pool, they looked up waving and smiling when they saw him.

"Crepuscolo." Dawn said from behind, startling him.

"Uh hello Ms Morgan." He mumbled.

"I see you've noticed some changes?" She asked.

Crepuscolo looked around, and realized that several lights were on. Dawn only had three working light bulbs in the house at any given time, one in each bedroom, and one in the bathroom. All to save money on hydro.

"Yeah, a couple." He replied, confused. "How?"

"Those videos we made..." She started to say as Crepuscolo blushed. "They were very, um popular."

"Really?" He said wide-eyed.

"Yes." She said matter-of-factly. "When my usual buyers weren't paying, I found a very secure website where people could pay for a viewing."

Dawn loved to slip in real estate jargon in everyday conversation. Crepuscolo's mouth fell open at her words. He couldn't imagine anyone paying to watch those videos.

She put a hand on the bottom of his jaw and closed his mouth as she spoke.

"Buyers can only view the listing once, then have to pay to watch it again. They also can't download it." She said.

"So..." He said still puzzled.

"So I even blocked whole countries and states, such as Florida and Quebec." She said beaming as she spoke.

"Wow!" Was all he could manage to say.

"You're wondering how much did it make over the weekend?" Dawn asked.

Crepuscolo nodded.

"It's been a steady increase." She said. "Our customers appreciate that our listings are... um unique."

He just stared in amazement at Dawn, looking her in the eyes, then looking down at her breasts and body. She wore a large men's shirt, which covered her bountiful chest, she also had on a pair of blue jeans.

"I know what you're thinking." She said smiling and putting a hand on his shoulder. "You don't have to work for me any more. I've put out a tender for a replacement!"

Crepuscolo did his best to cover his disappointment. Although he might be dating Sabryna, he liked the idea of daily blowjobs.

"Don't be upset," Dawn said noticing his concern and hugging him. "You have school, and basketball. You don't have time for making movies."

"Yeah." Crepuscolo said defeatedly.

"Besides," She continued to say, letting him go. "I'm still paying your parents, even without you working for me. I've already made a small cheque out to them."

He looked at her, surprised again, but also wanting another hug.

"Don't worry! I told them it was a delayed dividend." She said. "So look surprised when they tell you!"

She slapped him on the arm, then walked away, leaving him more confused then before.

The week passed quickly. He didn't see Sabryna at school, she must have been avoiding him, but now that Dawn was making money, he finally had money for Bus fare. So he didn't mind the cold shoulder.

Before the week was through, Dawn had found her stunt cock. He was a giant juice-monkey, and Ex-Marine. Despite what would be a reputation for being slow, Kirk was a decent fellow who trying to rediscover himself after multiple tours in Iraq.

Crepuscolo was initially jealous, but warmed to him. Kirk convinced Dawn to buy some old work-out equipment, which the two of them used almost daily to pumped iron together. In a few weeks, he even moved in; eventually Dawn were dating as well as generating content together.

Dawn gave Crepuscolo a free login to the site, to see his videos, but it also gave him access to their content. In the three weeks since Kirk appeared on the scene, the content they put together was rather large. It wasn't as popular as his work, but now with a growing library, the cash flowed in steadily.

Each night after his shower, and before he went to sleep, Crepuscolo would Jerk off to everything they posted. He didn't think he was obsessed, but he often would watch the entire collection twice. He even started sleeping in the nude so he could wake up at any time and 'crank one out' to her videos.

Crepuscolo couldn't believe how much of a whore Dawn had become! Real estate was her first profession, but pornography had replaced it! She did it all, cumshots, facials, and creampies. They fucked in her bed, on the sofas, the hallways, even in the pool!

There were videos of them wrestling, others had her pretending to be babysitter. It was a perverts dream and Crepuscolo's private stash.

Dawn drew the line with anal, Kirk was six foot tall and packed seven inches of manhood, with a girth that would 'split her in two!' As she would often say in her videos.

All seemed good at this point, Crepuscolo's grades were up, his playing stats were steady, and Dawn had a job again. They also had constant requests from their 'fans' if you could call them that. They obviously wanted anal, but they also wanted to see him back in the videos, or both he and Kirk tag-teaming Dawn, or just the two of them without her.

The cracks in this golden age came from Kirk. He had seen a great deal overseas, things that he couldn't talk about, but instead he relived in his dreams from time to time. Crepuscolo didn't know about the tossing and turning, or the sleepless nights, but he did hear the screams, the crying mixed with unspeakable sounds that came from Dawn's room.

Prayer and pornography helped him a great deal he said, but it wasn't a cure by far. Crepuscolo did find a solution for himself. When Kirk's cries began, he'd open the curtain, put in his ear plugs then head back to sleep, the sunrise would wake him.

Dawn however had no such luxury. She had come to admire Kirk for his strength and stamina by day, and tried her best to comfort him at night with little success. She often would retire to the sofa downstairs, however one night she was particularly exhausted.

"Crepuscolo?" She whispered into his darkened room.

He had his ear plugs in and was fast asleep. In the background Kirk could be heard calling in a nine-liner at full volume. She stumbled into the room exhausted, found his bed in the dark, and crawled under the covers.

In the morning Crepuscolo awoke to find himself on his back with Dawn's head on his chest. He wore just a pair of boxers; she seemed to be wearing one of Kirk's shirts, with nothing else on. His erection wasn't touching her, but it was oozing fluid.

"Ms Morgan?" He said quietly.

She looked up at him with her deep brown eyes, blinked several times before speaking. "I hope you don't mind?"

"Uh, did we?" He asked still confused.

"No silly!" She said patting him on the cheek. "Kirk had a bad night."

"Oh yeah? He did." He replied, then felt dumb for saying it.

He chastised himself for not saying something more clever or in-depth. However by the time he thought of something she stood up to leave the room saying a quick thanks. He stared at the doorway for a few minutes before he took care of his aching problem.

The rest of the week he would wake in frustration when he saw she wasn't there. He loved holding her in his arms, and schemed of ways to get her back in his bed.

He thought for a moment about causing Kirk some trauma, but gave up on that quickly. He wanted Kirk's woman, not his soul. His next idea was best. He'd forgo any clothing when he slept, he figured that Dawn wouldn't care provided that he was quiet. Lastly, he'd Jerk-off only once before bed to ensure he was as viral as possible!

This plan to came to nothing, Kirk slept like a baby for the next several weeks, meaning no visits from Dawn. Crepuscolo gave up on his silly ideas of getting Dawn to sleep with him.

One morning when Dawn, and Kirk gave him a ride to school. They were headed to the coast to shoot some outdoor content. He wanted to join them, but Dawn wouldn't hear it, 'school first' she said.

The drive to school was uneventful save for an auto accident they drove by. A car had flipped on its roof; however everyone was fine as they stood around talking on cell phones near the wreck. Crepuscolo had forgotten all about it by the time he reached his first class; however it was a powerful trigger for Kirk.

He did catch a glimpse of Sabryna in the hallway that morning, however by the time he fought his way through the crowd, she was gone.

That night Dawn's room roared with the sounds of a man re-living an IED strike. Crepuscolo, stripped off his clothes, put in his ear plugs as he said a prayer for his friend before he fell asleep.

When Dawn crept into his room later, he was once again oblivious to her presence. When he awoke, he was on his side, with her breasts pressed against his back. Pulling out his ear plug, he could feel Dawn's breath on the back of his neck.

"Thank-you." She said with a kiss between his shoulder blades.

"Uh, anytime." He mumbled, but she had gotten up and left; he didn't even see what she wore.

Frustrated he came up with his best plan yet. When Kirk started his bad dreams, he wouldn't put in the ear plugs, instead he'd wait for Dawn. He also put his back to the wall, to ensure that he'd be the big spoon this time.

Crepuscolo awoke startled, Kirk was calling in a fire mission loud enough to be heard over a helicopter. He placed his back against the wall, waiting for her to appear. Seconds turned to minutes, finally Kirk quieted down. Frustrated Crepuscolo closed his eyes to give into sleep.

When he awoke Dawn was in his arms! He had one hand on her stomach, the other was under her neck, laying flat on the bed. His face was buried in her tick brown hair; the aroma of fruity shampoo filled his nose.

"This must be a dream!" He thought to himself.

Not wanting to waste this opportunity, he moved his hands with the slow patience of a man not wanting to make a mistake. Dawn was clad in one of Kirk's dress shirts, that went down to her ass. Her smooth legs pressed against his; her feet were on top of his.

His hands finally came to rest on her breasts, his hips instinctively pushed forward, his erection stabbing into her shirt.

"I see that someone is wide awake?" She said jokingly.

Crepuscolo didn't let go, but he did stop jamming his spear into her rear.

"Uh, yeah a little bit." He said before regretting his words.

Dawn laughed but didn't get up, Crepuscolo counted that as a good sign.

"I'm going back to sleep," she said. "I want you to hold me tightly without trying to have sex with me. Can you do that?"

"I can try..." He said honestly.

"Good." She said going silent.

He could tell that she had fallen back to sleep. Unsure how to proceed, he held her breasts, which felt like two large baseball's soft to the touch. Her nipples were initially erect, but then relaxed.

Like a kid left in a toy store, he didn't know what he wanted to play with first. Should he open her shirt, to tug on her nipples? Squeeze her breasts, or stick a finger between her legs?

Once he finished his mental menu, he remembered that she wanted to be held, and not groped up like a passed out prom date. His personal dilemma ragged in his mind, debate upon debate. He still had his palms clutching her chest, yet he couldn't bring himself to do anything else.

"Crepuscolo," Dawn finally said waking once again. "Thank-you."

She escaped his grasp easily, and when she was kneeling over him, kissed his lips, repeating her thanks. She then left the room.

"Shit!" He said, feeling that he spoiled the opportunity.

Later that day, Crepuscolo had a special exercise session with Kirk. After repeated requests from their fans, the two men were doing a 'scene' together. Dawn had set up several webcams to record it all from several different angles.

Arriving at the back yard Crepuscolo could see Kirk by the exercise equipment wearing only a pair of shorts, and rubbing baby oil into his skin. Dawn stood inside waiting for him.

"What took you so long?" She asked worried.

"I was... I'm a bit nervous." He said in a worried tone.

"Don't be." She said putting a hand on his arm. "You've done this before many times."

"Not quite like this." He replied.

"Perhaps this will make you more comfortable?" She said handing him a black and purple Mexican wrestler's mask.

"What's this?" He said with a laugh.

"It's to cover your face." Dawn smiled as she spoke. "Who knows where you'll be after you graduate."

"Yeah, you're right." Crepuscolo said donning the disguise.

It was tight, but neither did it interfere with his vision, nor his ability to speak. He finally felt the courage to go outside. Dawn put up an arm to stop him.

"Lose the shirt." She said sternly.

"Yes ma'am." He replied, and pulled it off.

Dawn looked outside at Kirk, he was double checking webcams; she then ran a hand down his chest, then stomach.

"Thank-you again for being there for me." She whispered.

"Anytime." He felt stupid as he said the words. It sounded like he was deadly alien hunter in a jungle.

"You look kinda cute in that mask." Dawn seemed to be leaning in for a kiss when Kirk spoke up and waved with a thumbs up.

Crepuscolo blushed under the mask, took a deep breath and spoke. "I'm ready."

"Good!" She said with a smile. "I'll be in here, working on the computer; out of sight of the cameras, and making sure everything goes smoothly."

He nodded his understanding. Dawn handed him a small plastic bottle and said. "You'll need this."

He took what he understood to be a bottle of baby oil, squirted a blob into his hand and rubbed it into his chest. Dawn stepped aside to let him out, giving him a pat on the bottom as he walked by.

"OK Big K, I'm ready!" He said loudly, using Kirk's stage name. "What do you want to do first."

"I think a good warm up, with some stretching would be a good idea before the main event." He bellowed back from the other side of the pool.

The two men then engaged in jumping jack's, push-ups, and stretches together. The hot Florida sun shown through the netting that covered the pool and small backyard; it glistened off their sweaty muscular bodies.

Crepuscolo was tall, lean and athletic, with skin the colour of mahogany. His short black hair, and strong east African features a striking contrast to Kirk. Who was more stocky, muscular and heavily tanned, with long brown wavy hair.

"Do you feel limber now?" Kirk asked.

"I sure do!" He replied his chest stuck out.

"Good!" Kirk replied, clapping Crepuscolo on the shoulder.

"So how do you want to do this old man?" He said grinning.

"How about a run first?" Kirk asked.

"Sounds good!" He said walking over to one of the two treadmills. "Can I have your walker if I win?"

"This 'race' will turn into a chase if you keep that up." He said chiding his friend.

The two men then agreed to a five kilometre race with bragging rights going to the man who finished first. Nineteen years in the Marines, meant several thousand forced marches, and runs. However with a six kilometre run one way to school racing against the clock, Crepuscolo knew he would have the edge in this contest.

Kirk set his treadmill at a steady pace, he planned on expending his energy on the last leg, when he could overtake his opponent. Crepuscolo, lacking the knowledge of many years, and multiple runs; went full out as fast as he could.

"Maybe we should be racing for Dawn's honour?" Crepuscolo shouted to Kirk. "Winner takes all!"

In the other room Dawn switched between cameras on the computer, trying to put together a video for her 'buyers'. When she heard Crepuscolo's words, she first laughed loudly, than stopped when she realized that he may mean it.

Outside the two men were dripping in sweat. The eyelets of Crepuscolo's mask kept it from going in his eyes, but he could feel the heat multiplied by wearing it on his head. All around the bottom of his head covering, sweat poured out; it was hot and uncomfortable, but the privacy it gave him was well worth it.

He suspected that hundreds of perverts were holding their cocks and waiting for the outcome of the race. He wanted to win, not just to put on a good show, but also to get Kirk's consent to have sex with Dawn, even if he had to beat him to get it.

Kirk had common sense to put his hair in a scrunchie; he hadn't sweat like this since his time in Iraq. His mind wandered off to Operation Rolling Thunder, when his HUMV broke down and he had to run for cover.

"Stay in the moment." He whispered to himself.

Crepuscolo called out each kilometre he passed. Kirk could see he was lagging significantly, and increased the speed on his treadmill. He was surprised how fast he was without his helmet, rifle and gear.

"Come on old man!" Crepuscolo shouted.

Kirk kept quiet as he focused on his strides. He knew that Crepuscolo's ancestors hailed from that region of Africa that included some of the fastest runners in the world, but he also knew with that mask on he'd hit a wall. When that happened, he'd over-take him.

Crepuscolo didn't think he was a showman until today. He was playing up to the crowd that was watching closely. He turned up his incline to allow Kirk the opportunity to catch up, but he had no intention of letting him win. When they were both around the four kilometre mark, he would level out, then force himself to go faster than before.

He planned on calling out each hundred metre, but the mask was much too hot for that. His brain felt cooked under the leather, the only relief he knew was winning, followed by a swim.

Kirk said something in military-lingo, like FNG, or the like. Crepuscolo laughed, but could do little else, he knew that Kirk would be in hot water with that foul mouth. Dawn was many things; real estate agent, pornstar, whore, and possibly a swinger; but she was also a god-fearing woman of the south, who wouldn't abide a curse word under her roof.

With a victory roar, Crepuscolo crossed the five kilometre mark, slammed to stop button and cannonballed into the pool. Kirk kept going until he too finish.

Speaking loudly to Kirk Crepuscolo chanted. "I won! She's mine! All mine!"

Kirk laughed loudly, he knew that Dawn was a prize, but not one that could be won.

"That was just the first round." He replied.

"Oh?" Crepuscolo said in exaggerated motions.

"We still have more events." Kirk said smiling.

"If it's a water fight, then I have you beat!" Crepuscolo said splashing Kirk with water.

Dawn watched the two men splash and wrestled in the pool, and couldn't believe the high viewership they were getting for the un-edited version of the video. She didn't think there would be so much demand for two men horsing around in the pool, but there it was.

Dawn was dressed in a Navy blue bathing suite with a baby blue sarong wrapped over. With her legs parted, she pulled her bottom aside to strum along with the video. She had finally discovered what the enchantment of two men really was.