Risky Obsession Ch. 10

"It's a thousand, sweetie," said the dark-haired, busty woman as she put her makeup on in the dimly lit hotel room downtown. Frank sprawled out on the bed typing out a message on his phone.

She stopped and turned to him. "A thousand," she said sternly. Frank finally looked up. "You really think I'm not good for it?" he asked.

She frowned before returning to her eye liner. "You'd be surprised at the types of clients I deal with daily."

Frank returned to his phone. "I can only imagine." He was completely naked on the bed. His cock rested in its flaccid state, having just cum a moment earlier. This was his normal routine. Sex with a hooker in a hotel room when he was traveling on business. Tonight it was Scarlet. If it wasn't a hooker, it'd be some random bartender or waitress he picks up. This was his life now. There was nothing about it that he was particularly proud of.

Suddenly, there was a knock on the door. Scarlet turned to Frank, excited. "That's him!"

Frank nodded in the direction of the door, indicating he'd like Scarlet to get it. He returned to his phone, uninterested.

"Hey you!" she called out as she opened the door. In it, stood a tall black man wearing a full suit with no tie. "Hello, precious," the man said in a deep voice. He took her hand and kissed it as she led him into the hotel room.

"This is Frank. Frank, this is Leon."

"How you doin', Frank?" Leon asked, extending his hand to shake. Frank looked up briefly, nodding in Leon's direction, but still immersed in his phone.

"Alright then," said Leon, unaffected by Frank's coldness. To him, it didn't matter. He was there for one reason. To fuck a beautiful escort and get paid to do it. "Do you have something to drink?" he asked Scarlet.

"Mmm hmm," she said as she opened the minifridge and took out a bottle of champagne. She poured three glasses, handing one to Leon and one to Frank.

"Thank you, ma'am," said Leon.

Frank quietly stood up from the bed and took his seat at a chair in the corner. He sipped his champagne while playing with his cock.

"Don't mind Frank," said Scarlet, smiling in his direction. "We just had sex. He's still recovering." She winked as she looked at his soft penis.

"Very funny," Frank said. "So here's the deal, Leon. You're going to have sex with Scarlet. I'm gonna watch from over here. I may join in. I may not. You'll get three hundred."

"Fine by me, Mr. Frank," said Leon.

"Don't use my name anymore."

"Sure thing."

Frank eyed Leon from head to toe. "You're tall," he said.

"I told you he was tall, dark and handsome," Scarlet said as she reached up on her tippy toes to kiss Leon.

"How big is your cock?" Frank asked, wasting no time.

"Eight and a half. Maybe nine," Leon said with confidence.

Frank nodded. "That's good. I'd like you to talk dirty during this. I'd like you to remind me how small I am. Poke fun at me. Tell me I'm less of a man."

Leon was all too familiar with this dynamic. He had done it many times, mostly with married couples. A few times with escorts and customers. "Whatever you'd like," he agreed.

"Alright, Leon. Go ahead and get started. Let's see this thing," Frank said as he propped his feet up on an opposite chair and sipped his champagne.

Leon smiled as he began to slowly undress. Scarlet stood by in anticipation, legs crossed, with one hand holding up her elbow. She sipped her champagne excitedly. For her outfit, she opted for her stripper outfit. A low-cut shirt with a miniskirt, leggings and a crop top. Her dark hair was half in a bun, half down.

Leon was extremely muscular and fit. Both Scarlet and Frank watched as he revealed each portion of his tightly toned body. Eventually, he stood before them in nothing but tight-fitting light gray boxer briefs. The outline of his soft cock was visibly squished across his right thigh. It looked to be enormous.

"Mmmmm," said Scarlet as she approached him and felt his hard abs. Her fingers ran down his body to his briefs, lightly tracing the outline of his penis. "You're so packed in there, huh?"

Leon bent over and kissed her, helping himself to handfuls of her big breasts. He then moved to her rear, squeezing her ass. Scarlet moaned softly. As Leon explored her body more and more intimately, he began to grow a sizable erection. After several minutes of heavy petting, Scarlet pulled their lips apart and looked down. She gasped. "Oh my Lord, look at this," she said as she felt his hard cock over his boxer briefs. "You're massive."

Leon didn't say anything. He turned to Frank who was playing with his own cock. "You see that?" he taunted. "Should I show her what I got?"

Frank nodded, in a trance as he watched. "Take it out," he said.

Leon stepped back so both could see clearly. He slowly lowered his boxer briefs, revealing inch by inch of his thick cock. It seemed to go on forever as he revealed the long and sturdy shaft. Finally, it freed itself and bounced up heavily.

"Fuck," Scarlet whispered. "That's so hot," she said as she grabbed it and began to stroke. "Your cock is so big," she said.

"You like it?" Leon asked as he lifted her face up by the chin. She smiled up at him. "I love it," she said before looking back down at his substantial member.

Frank continued to watch. He rubbed his cock as it began to strengthen. The scene unfolding before him was one he was very accustomed to. In his experience with escorts, the addition of a bigger man into the equation was something Frank treated himself to once and again. Not to say he was incapable of pleasing Scarlet (he had moments ago,) but something about watching a woman worship and be fucked by a bigger man was always pleasing for Frank.

Scarlet sat on the edge of the bed as Leon stood in front of her. She grabbed his cock with both hands and slowly stroked it. "It's so big and thick. God I just want to taste it."

"Not yet," said Frank. They each looked over to him to see he was jerking off. "Spit on it first. Stroke it. Get him really hard."

Frank was the boss. Scarlet did as she was told and began to stroke Leon's meaty pole. He groaned in delight. Her tiny hands struggled to cover all available territory, but the sensations still were more than enough for Leon. "Mmmm girl, you doin fine," he said. "You keep that up."

"You're so fucking hard," she said. "It's like concrete or something," Scarlet giggled as she looked up at Leon. He smiled down at her.

After a few minutes of a handjob, Scarlet turned to Frank. He stared deeply at them as he masturbated. Scarlet smiled sweetly. "Frank, honey? Can I please suck this cock?"

Frank said nothing, but nodded slightly, granting her permission. Without hesitation, Scarlet devoured as much as she could of the big cock. Leon's head shot back in pleasure as he moaned. Scarlet jerked the lower portion of his long shaft with one hand while sucking the head and a few inches with fervor.

"Ohh fuck," Leon said. "Fuck, that's good. She's good," he said, turning his head. Frank was busy masturbating feverishly. He only stopped to moisten his palm with his mouth before getting right back to work.

"You can only wish you could have a cock this big," said Leon in his first display of playing the role Frank requested. "Can only wish, little man."

Scarlet softly squeezed Leon's big balls as she sucked him dry. She was able to get nearly half his cock inside her mouth. "You're doin fine, girl," Leon said as he closed his eyes and looked up. "So fine."

As she pulled his cock out of her mouth, she gasped for air. "Oh my God! You're so big!" She pulled and tugged at his cock, covered in her saliva. She turned to Frank and smiled. He was stone-faced, jerking off as he watched her handle Leon. He solemnly nodded indicating it was time.

Scarlet laid back down on the bed and spread her legs. Leon looked down and licked his lips while he stroked his rock hard cock. "You ready for this baby?" he asked. Scarlet nodded. She was more than ready. "Just be gentle," she reminded him.

Leon climbed onto the bed and positioned himself between her legs. His cock rested on her belly, stretching across her abs. She playfully petted it, somewhat nervously trying to delay penetration.

Frank joined them on the bed. He laid next to Scarlet, clutching his cock. "Are you ready?" he asked her. "Yes!!" Scarlet squealed, half excited, but half nervous.

Frank nodded to Leon. He then resumed jerking off while Leon pressed his cockhead up against Scarlet's bright pink snatch. He licked his fingers and rubbed it on his cock. He then gracefully pushed forward as his massive cock began to fill her up.

"Ohhhh fuck," Scarlet said as she leaned forward and watched Leon ease himself in. "You're so fucking huge," she whispered. "Look at that."

Frank watched too as he feasted on her boob. He sucked at her nipple feverishly while he watched Leon work his way into her inch by inch. He fucked her like a true gentleman, an inch in, half inch out, another inch in, another half inch out. Frank watched with both envy and admiration, often longing to know what it must feel like to have such a big penis.

In no time, Leon struck a rhythm. He was penetrating the petite Scarlet with ease now. In long and smooth strokes, he pushed his cock to depths rarely felt by the experienced escort. She was in heaven as she clutched the sheets, Frank, her legs, Leon's arms... whatever she could get her hands on. After only five or ten minutes, she was already cumming.

"Ohhhhhh God! You're so good! Fuck me! Fuck me!" she screamed out, unconcerned with being heard in the busy hotel.

Frank switched between watching Leon's cock penetrate her to watching her facial reactions. He pumped away at his cock, making sure to take long breaks so as not to ejaculate too quickly. After all, he paid for this.

Leon was already breaking a sweat. His tight muscles were glistening, providing plenty of visual stimulation for Scarlet as she watched him work. Despite his aggressive fucking, he was nowhere near finishing. For the next thirty minutes, Leon fucked her missionary, doggy, on her side, reverse cowgirl, and finally back to missionary for the finale.

Frank knelt next to Scarlet, aiming his penis at her breasts, while Leon neared orgasm between her legs. "You ready baby?" he asked. Scarlet nodded. Leon looked up at Frank who also acknowledged he too was ready.

"Ohhhhh fuck!" Leon moaned as he pulled his big cock out just in time to drop out a thick load onto Scarlet's belly. She watched with excitement as bright white cum dripped out his cock head, forming a puddle on her stomach. While she watched him cum, she got smacked in the face with another thick load from Frank.

"Argghhhh!" Frank shouted. He was more of a shooter than Leon, easily caking Scarlet's face, neck, and breasts with his copious seed. Both men moaned in pleasure as they spread their cum all over Scarlet who giggled sexily while watching them orgasm.

"Oh fuck!" Leon said as he stroked the last drop out. Frank too had resigned with his hands on his hips, panting while the last drop of cum dripped out his cock.

"My goodness," Scarlet said, laughing. "You guys are like synchronized shooters!"

Leon smiled at her. "Let me get you cleaned up baby."

Scarlet dropped her head back down on the sheets and closed her eyes. "I'm gonna need a wheelchair, guys!" she joked. Frank was already cleaning up and getting his clothes on. He reached for his phone to see there was one text message.

Cynthia.

"We need to talk when you get home."

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Amy stared out the window of Charlie's car. She was speechless. She didn't know if she should cry, shout, or laugh. She was both angry, saddened, and embarrassed all at once.

How could she not have realized her boyfriend was having an affair with his stepmother? She had been around the two of them often enough. Sure, Cynthia was dropdead gorgeous and fairly young. What man wouldn't be attracted to her? But for it to be her own stepson, and Amy's boyfriend... well, that was another whole thing.

"You alright?" Charlie asked.

"This is just such bullshit," she said. "He told me he loved me."

Charlie couldn't disagree. He felt awful for Amy. And he felt betrayed by his two best friends for keeping such a secret from him.

Amy turned to Charlie. She had tears forming in her eyes. He could see the hurt she was feeling. "We need to get back at them."

"Get back at them?"

"Yes. Fuck them. I'm gonna tell everyone about this."

Charlie shook his head. "No, Amy. C'mon. You can't do that. People's lives could get destroyed. There has to be another way."

"Whether you're with me or not, I'm gonna out them all."

Charlie hesitated. There seemed to be no way to stop Amy from whatever she planned to do. He hoped she wasn't going to do anything drastic, but feared she was on a mission now. "What if no one believes you?" he asked, desperately trying to discourage her.

"I'll catch them. I'll film them doing whatever it is they do and then I'll have proof."

Charlie shook his head. "Amy, I think they're all done. I really do. At least she's done with Kevin. She told Peter."

"So I'll catch her with Peter. Either way, I'm gonna get this woman in trouble. She ruined everything."

Charlie sighed as he looked out the window. There was no stopping her. But he feared letting her go it alone. "I'll help you."

She turned to him. "You will?"

"I can't let you get hurt. Who knows with them. And Frank too. It's a dangerous situation I feel."

Amy reached over and kissed Charlie on the cheek. "Why can't all guys be as sweet as you?" she asked before kissing him again, this time, placing her hand on his thigh. She rubbed it while looking up at him smiling. "You're the best," she said.

Charlie tentatively nodded. He was very unsure of what he was about to do. It was not an ideal situation. He couldn't help but feel angry about what happened, but to out them all seemed like it was going too far. Tremendous guilt occupied his conscience.

But that guilt quickly faded once he felt Amy's hand travel further up his thigh, landing squarely on his crotch. He began to harden.

"What do we have here?" she asked cutely. "Someone saying hi to me?"

Charlie's arousal took over. He leaned back in the car seat and spread his legs. "Sure seems that way, doesn't it?"

Amy happily reached for his belt buckle, carefully unfastening it. Next, she unzipped his pants and spread his fly. In no time, Charlie's hard cock was exposed and Amy wasted no time taking hold of it. "Nice," she said to herself as she gazed at Charlie's penis for the first time. She felt wet with her own arousal.

Amy licked her hands and went to work. She stroked his cock, smoothly glazing it up and down. His five inch shaft was just big enough for one hand to do the work. Amy rested her other hand on Charlie's hard abs to feel his breathing increase. "You have such a nice penis," she told him. "It's beautiful."

Charlie's arousal grew. Despite feeling wrong about what he agreed to do, he was now in the moment and enjoying a handjob from a very attractive girl. What could it hurt?

After several minutes, Charlie started to moan. He spread his legs further and grabbed Amy's back with his fingertips. "You close?" she asked.

"Yes," he nodded. "I'm gonna cum."

His semen shot out onto his shirt. Amy quickly lifted his shirt with her free hand after the first shot so that the ensuing loads landed on his stomach. "Yessss," she whispered quietly as his cum spread across his belly. "Shoot it out," she said lovingly.

"Damn," Charlie said as he came down from his orgasm. "That was unexpected."

"It's the least I could do," Amy responded as she wiped the cum from her hand onto Charlie's stomach. He pulled his shirt down before pulling his pants back up.

As Charlie drove her home, he looked over at her during a red light. She smiled sweetly and turned her head. Charlie thought she was beautiful. Seemingly devious, but strikingly attractive. He found it charming how she gave him a handjob like it was nothing. He sensed she may be starting to like him. He certainly liked her.

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It was another week before the opportunity arose. The plan was for Charlie to alert Amy once he had an indication Peter and Cynthia would be meeting again. The same applied to Kevin, but as Charlie had correctly assumed, that fling was no longer.

Charlie knew it was time when Peter abruptly left the bar they and another couple of friends were sitting at. It was immediately obvious what was happening. Peter got a text on his phone and wrote back in a hurry. He then awkwardly looked around the bar for a few moments before announcing he was leaving to help his father with something.

Once he left, Charlie worked on his own excuse. Unfortunately, he was no better at lying and decided to go with the 'I'm tired' approach. Luckily, his other two friends were unphased and waved him goodbye as if it was nothing.

He called Amy and, before long, they were in the car headed to the Riley household.

"I can't believe we're doing this!" Amy said as she excitedly squeezed Charlie's arm. "This is so crazy!"

Charlie forced a grin. "Yeah," he said tentatively. "You sure you wanna do this? There's no going back," he warned.

"Let's nail them," she said. "I want to get back at her. I need to get back at her." Amy had a certain evilness to her, but mixed with a bubbly sweetness. Charlie didn't know what he thought of her. One thing was for certain though, he wanted to fuck the living daylights out of her when this was all over.

The house was mostly dark except for the kitchen lights. They parked down the street and decided to sneak around the back patio, near the pool. From there, they could get a decent view into the house without getting caught.

"They're in the kitchen!" Amy said.

"Shhh!" Charlie quickly fired back. "We need to be quiet. Here, follow me."

Charlie led Amy to a spot in the backyard where they could each stand on a storage container. Above, there was a window where they could see almost all of the kitchen. Charlie and Kevin used to use the window to make sure the coast was clear before they lit up joints as kids in the backyard. Tonight, it was serving a much different purpose.

"Holy shit," Amy whispered as they peered into the house. What they saw inside shocked them both. Right there, standing in the kitchen was a completely naked Peter. He leaned against the counter top chatting with Cynthia. He held a glass of wine in his hand. He was telling a story in a very animated way. So much so that he was waving his hands a lot.

"Oh my gosh," Amy said as she stared. Charlie knew exactly what she was looking at. Peter's soft penis was on full display, dangling well past his large testicles, swaying back and forth as Peter told his story. It was surely a sight to be seen.

"Is he kidding?" Amy asked, turning to Charlie for the first time.

"No... he's blessed," Charlie agreed. Even he was impressed having seen Peter for the third time.

"It's like a third arm!" Amy called out, a bit louder this time. Charlie responded with another shoosh. The last thing he needed now was to get caught before they even did what they needed to do.

Suddenly, Cynthia appeared in view. She too was naked. She stood in front of Peter, blocking their view of him. Her ass, firm and round, faced the two as they peered into the window. As she stood on her tippy toes to kiss Peter, she lightly grazed her ass with her hand.

"Holy shit," said Charlie. Amy giggled. It was his turn to marvel at something.

"I have to admit. She keeps things together for being forty."

"Thirty-nine," Charlie corrected her.

Cynthia then put her hands in front of her. She started kissing Peter's chest. Peter put his wine glass down and looked towards their crotch area. Cynthia was using both hands to pleasure him. He then turned his head up and closed his eyes, clearly experiencing great pleasure.