He woke up to the sound of the door opening. He checked to see Caroline was covered properly before he turned. It was Max, but there was no need to scare her.
“Hi, Max,” he said, just loud enough to wake Caroline, who opened her eyes, only to close them back to fake sleep, realizing that she was still naked.
"Welcome to the Channing-Black estate," Max said as she walked in with several bags filled with ingredients. "The estate includes a couch, half a kitchen, and a fire escape with a view of another fire escape. I hope you’re satisfied with our hospitality."
“Oh, I am,” he chuckled. “Even though the other hostess wants to fake being asleep.”
Caroline opened her eyes. “Hey, I’m not faking sleep. I’m just … resting my eyes.”
“Well, you needed your rest,” he teased while she blushed, burying herself even deeper into the bed.
Max chuckled, but otherwise didn’t react as she moved to the open kitchen, and started working on setting the stuff.
He adjusted himself so that he was pressing against Caroline’s ass, which was enough to silence her. “Making cupcakes?” he asked.
“Just the prep,” she said. “I bake them in the morning to make sure they are fresh, but handling them early helps.”
He kissed Caroline’s cheek and slipped out of the bed, wrapping a towel around his waist as he walked, happy to display his muscular body. “Let me help. That’s the least I can do for your hospitality,” he offered.
“Hey, don’t mess with my stuff,” she said. “Also, looking at Caroline’s smile, you have already done your part. I have never seen her smiling that big.”
“Oh, that was not a chore, but a joy,” he said, catching Caroline’s gaze while she blushed. “Teaching has its own merits.”
“Teaching?” Max asked. She looked at him, but he just smirked and nodded toward Caroline. “Caroline…”
“Well…” she muttered. “Did you know that a proper orgasm is supposed to leave your legs tingling and unable to move? Because I didn’t.”
That made Max look at him, surprised. “Damn. Maybe I should date more artists if that’s what you’re capable of…”
He chuckled as he approached her. “I can’t guarantee. I would like to believe I’m the exception,” he said, flexing.
“You have no shame, don’t you?” Max said.
“Naturally not,” he responded as he arrived in her kitchen. “Now, let me help. I don’t deal well with nothing to do, and I don’t think you watch me teach your precious roommate.”
“Oh, I disagree. It’ll be better than cable.”
“Max,” Caroline gasped. Max chuckled while Caroline wrapped the sheet around herself and retreated into the bathroom, leaving them alone.
“Now, tell me how I can help you,” he said, even as he pulled out the flour and the large-scale sifter.
“Hey, the last thing I need is for you to make a mess—“ Max started, only to pause when he started to move with perfect precision. Master Cooking was no joke. “Alright. You know how to cook.”
“Grew up on a farm with a crazy uncle and even crazier veteran neighbors,” he said. “Learning how to cook my own desserts was the only way to get something that wasn’t burnt.”
[Achievement complete. Seduce Max Black.
Challenge: Hard]
[+10 Charisma
1 Random Gold Skill
1 Random Gold Reward]
Charisma was a surprising reward, but then, thinking about her whole thing, it made sense. She was beautiful, but she also had a presence about her.
“Wow. An artist who knows how to do actual work. Will wonders never cease?” she said. “Can you do magic?”
He chuckled even as he reached behind her ear, and pulled a coin, then let it dance between his fingers, flicked up, and let it fall down, and disappear. However, just as he did so, he also took a step forward, noticing that she had unzipped the back of her uniform, which allowed him to pull a surprisingly effective trick.
He dropped his towel, deliberately catching it with one hand to keep himself mostly covered, but with her attention on that, he managed to succeed, and actually took her bra, something that even impressed himself by pulling off.
“That was not very impressive, is it?” she said, trying to cover up her reaction to the towel, still not catching what he did, partially due to his smooth trick, partially due to exhaustion making her distracted. “It’s good that you’re not perfect.”
“Oh, are you sure about it?” he asked. “Are you sure you’re not missing something?” he teased, letting her process it before he revealed his reward. Shocked, she patted her chest, only for her eyes to widen.
“Holy hell! You’re good,” she gasped.
“That’s what the girls usually say,” he teased. “Flexible fingers are useful playing the piano, cooking, magic … and let’s just say they had advantages to tingly legs.”
That made Max look both excited and regretful, but she didn’t make a move. “Now, my bra,” she said.
“Hey, I won that fair and square,” he replied and threw it onto the couch.
“You like to push your luck, do you,” she said, but despite saying that, she didn’t say anything when he occasionally brushed her while he helped her prep work.
Soon, Caroline returned, wearing a sexy pale blue nightie that was clearly saved from her rich-person days, and it looked amazing on her. “Oh, you’re so nice helping Max. I tried, but …”
“Let’s just say compared to her cooking, she’s an amazing waitress,” Max completed, and they chuckled. After the prep work finished, Max pulled a bottle of tequila, and three shot glasses.
“Now, to celebrate Caroline’s first real orgasm, let’s drink.”
“Or we can make it fun, and play truth or dare,” he said.
“Really?”
“Hey, it’s a good way to learn about each other, right?” he said.
“We can start as long as you get dressed,” Max said.
“Do I have to?” he said, flexing.
“Yes, Max. Does he have to?” Caroline replied, drooling at the sight of his muscles, even caressing his abs. It was an ego boost, regardless of the source.
“Fine,” Max said, trying to act reluctant, but she wasn’t very successful. “Just let me change. I feel overdressed.” She disappeared, and when she returned, she was wearing an oversized t-shirt, panties, and nothing else.
She looked good.
Caroline and he sat on the couch, and Max pulled a chair.
They spun the bottle. "Caroline, you first. Truth or dare?"
"Truth. Always truth first. Dares are for once we get properly tipsy."
"Fine. What's the most expensive party you've ever thrown?" he started.
Caroline's expression flickered. “My sweet sixteen party. I … I got into a competition with a friend. It probably cost more than this building," she said. “I used to be rich. Real rich.”
“Interesting,” he said.
“Really. No follow-up question?” she said.
“No. You lost your money, but you must have had connections to stay there as long as you sold your pride and accepted to be the mistress for some old guy. Instead, you chose to build a life by actually working. That’s impressive,” he said. “Anything else, I don’t really care that much unless you want to talk about it.”
“Thanks,” Caroline whispered, and even Max nodded, showing that he had passed a test.
They spun the bottle, which pointed at him. “Truth," he said.
"What's the most reckless thing you've done in the last month?" Max asked.
"I used my beat-up Mustang to race a Porsche on the highway,” he said.
“That’s all right,” Max said.
“Wait. Not finished,” he said. “I lost, but the driver turned out to be an undercover federal agent, and I ended up on a date at a shooting range.”
“Really?” Max gasped. “That’s like, the coolest story ever.”
“It was pretty cool,” he admitted.
"How was the date?" Max asked.
He smirked. “That sounds like another question,” he said as he spun the bottle, which pointed to Max.
"Dare. I don't do truth. My secrets will die with me."
He turned to Caroline. “Why don’t you take it," he offered, even as he put his hand on her thigh, caressing her skin. It was quick to turn her giddy.
“Fine,” Caroline said, thinking. “Remove your shirt,” she challenged, her tone suggesting she expected Max to refuse.
A bad call. She might have refused before, but not after he flirted with her quite a bit while cooking. Max grabbed her shirt, pulled it, and revealing her rather amazing chest. Spectacular, magnificent, and divine were the other words that could be used. “Done,” she said smugly.
“Max,” Caroline gulped.
“Hey, you’re the one that gave the challenge,” she said smugly as she leaned back, clearly proud of the show she was putting on.
Caroline paused, then shook her head. "Nope, you’re right,” she chuckled as she rotated the bottle. The bottle pointed at him.
“Come on, coward,” Max declared.
“Fine, dare,” he said.
“Remove your towel,” the predictable dare came. Unpredictably, it came from Caroline, and Max looked. “Hey, I started it, I better own it,” Caroline said, trying to sound confident, but failing spectacularly.
Max said nothing, her attention on his erection. When it was Caroline’s turn, she didn’t even bother asking, and just removed her nightie. Two of them were in panties, and he was naked.
A few quick truths that went mild, then Caroline asked for dare.
"I dare you to sit on my lap,” he dared.
The dare was simple, but one that started to turn the heat on even more. What remained of the ambiguity started to melt. Especially when he put his hand on her thighs, and caressed, the quick jolt of pleasure was enough to remove Caroline’s concerns about what was proper and acceptable while she was looking at her half-naked roommate. She started to use her ass to give a surprisingly elegant lap dance.
[Achievement complete. Convince Caroline to give a sexy lap dance with an audience.
Challenge: Hard]
[+10 Perception
1 Random Gold Skill
1 Random Gold Reward]
He went with the Stat, not stopping the dance.
Max watched without even blinking as she poured herself another glass. The room stayed silent for almost five minutes, then Caroline reached out and grabbed the bottle. She didn’t even spin it. She just pointed it at Max.
“Dare,” Max whispered in a throaty tone.
“Give him a blowjob,” Caroline whispered, her tone equally raspy. Their gazes connected for a moment, then Caroline nodded and left his lap, sitting to his right. Max said nothing as she sat on his left, leaned forward, and captured the crown.
Even without the show allowing him to cheat, he would have known exactly how to treat Max. Roughly, with actual aggression. Not because she needed it like Judith or Gloria, but she genuinely believed she didn’t deserve anything better.
Anything gentle would just spook her. Which was why he grabbed her hair and pushed her down, immediately invading her throat.
Caroline’s eyes opened, but before she could say anything, he kissed her. “Trust me,” he whispered, which was particularly amusing as he continued to invade Max’s throat. Yet, Caroline still looked hesitant, so he pulled Max’s head back.
“Why did you stop?” she asked, breathing deep, her eyes burning with desire.
“I wanted to show the princess here that I know what I am doing,” he said as he pushed her again.
Caroline trembled. “Does it make me a bad lover I can’t do that,” she asked in a small voice.
He chuckled, then kissed her. “No,” he whispered once he pulled back. “It’s not about clearing some kind of kinkiness scale. It’s about doing what each of us wants,” he whispered. He kissed her again, then started drifting lower, and kissed her nipples.
At the same time, he used his empty hand to grab Max’s much larger breasts that still maintained their perfection, and started squeezing hard.
Max moaned happily around his girth even as he pushed her down, confirming his guess that she had a taste toward the rougher side of the spectrum. Which contrasted greatly with the gentle kisses he was landing on Caroline, which was making the moment even more amazing.
The situation got even more impressive when kissed Caroline’s belly while he moved lower, and reached her panties. Any other time, he would have ripped them, but knowing that they were probably the best Caroline had in her current circumstances, with symbolic value, he just slid them down halfway to her knees and let his tongue dance.
Her moans were beautiful, almost as beautiful as the way Max moaned around him. Caroline climaxed first. “Take over for Max,” he whispered to trembling Caroline while he pulled Max back.
“Hey, I was enjoying that,” Max said playfully despite her desperate gasping for air.
“Oh, you’ll enjoy this more,” he said as he grabbed and ripped her panties.
“Hey, I paid five dollars for them—“ she tried to tease, but her words were interrupted by a moan when he slipped two fingers to her core, and his thumb caressing her clit. His fingers slid in and out aggressively, and she lost her words.
“Is she … alright?” Caroline whispered, her voice still trembling from her earlier climax.
“I can stop and ask her, but—“ he started, and Max let out a wordless cry of protest. “She might actually kill us. So, go down and start your work, princess,” he whispered. Caroline might not have appreciated being ordered like that another time, but the post-orgasm glow had a way of loosening such limits.
Max climaxed … hard.
[Achievement complete. Treat Max the way she prefers, with explosive results.
Challenge: Hard]
[+10 Charisma
1 Random Gold Skill
1 Random Gold Reward]
Skills from Max weren’t particularly urgent, and Charisma was one Stat that was lagging behind, so he picked it.
He pulled his hand, letting her recover, but not before putting his dirty fingers to her mouth and making her taste herself. She hummed. “Damn. Caroline wasn’t exaggerating. You know exactly how to play with the female body,” she said. “Your fingers are like jackhammers.”
Caroline raised her head and stopped sucking. “Really, Max. Must you be so crass,” she said, almost reflexively, before she returned to sucking.
They shared an amused glance, but to his surprise, Max actually carried a sense of hesitancy. “Alright, I got mine,” she said with a smug declaration that hid her true feelings, which included a lot of hesitation, grabbed her shirt and walked to her bedroom.
Her generous ass swayed until she slammed the door. Caroline, still around his shaft, didn’t pay much attention to that. Instead, she had a shy expression on her face as she pulled. “Can you … treat me rough as well?” she whispered.
“Are you curious, or do you want to prove something?” he asked.
Max would have hated such a question, but Caroline loved it. She paused, thinking. “A little of both, I suppose,” she said. “I always thought making love to be gentle and kind … but Max seemed to enjoy it and…”
He kissed her temple, which was a surprisingly gentle touch. “Fine. If you have any problem, just tap my thigh three times, alright,” he advised. She nodded, and he grabbed her beautiful blonde hair, pulling hard as he pushed her down.
She froze as his shaft pressed against her throat, but she was quick to relax. He pushed her down, her panicked gags making it even more fun … especially since she determinedly avoided tapping his leg.
He tightened his hold, using her like a sexy toy while she took obediently, though he was careful to manage. However, at the same time, he noticed something interesting from Max’s room, that she had the lights on, but there was no light coming from the keyhole.
Tactical Awareness perk was already paying off.
Also, very naughty from Max, but he didn’t do anything, and let her watch. Meanwhile, he finally reached his limit, and filled Caroline’s mouth. “Don’t spill,” he ordered, watching her struggle to swallow all.
Her clumsiness somehow made it even sexier.
[Achievement complete. Encourage Caroline to learn, after all, it’s never too late.
Challenge: Hard]
[+10 Perception
1 Random Gold Skill
1 Random Gold Reward]
“So,” he said as he flipped her, his supernatural endurance meaning his body quick to react, slipping inside her once again, but he made sure to angle her so that Max got a proper show. “Does it feel good?” he whispered.
“Yes. It’s amazing,” she whispered desperately before burying her face in the pillow.
“Really, the pillow?” he asked.
“I don’t want to disturb Max,” Carolina whimpered.
He spanked her playfully. “Considering where she stopped, I doubt that she doesn’t know what’s going on.”
“Still…” Carolina gasped, but that was all she was able to say as the orgasms started to get overwhelming. He didn’t let her, finally grabbing a bunch of her hair and turning it into a nice pseudo-ponytail that worked wonders as a handle.
After her earlier deepthroat, she was far more obedient in bed, her wanton moans filling the room, her grip tight.
Then, just as she was about to climax, they were interrupted by a knock on the door. “A little silence, please,” the voice said. “Some of us have to wake up early tomorrow.”
The voice was familiar, strangely so, but it wasn’t what he expected. Curious, he slammed into Caroline twice more, hard enough to trigger her climax, then stood up, wrapped his towel around his waist while throwing a nearby cover over Caroline to keep her hidden, then opened the door.
“Sorry about it, Red,” he said while giving the surprisingly short woman on the other side of the door his best smile when he took notice of her familiar face … and the fact that she got stuck looking at his six-pack with shock, followed by a quick dash of desire. “Tell you what, we’ll try to keep it down, how about it?” he said.
“W-well, see that you do,” she stammered, turned her back, and dashed away, leaving him to smile naughtily.
[Achievement complete. Impress Lily Aldrin.
Challenge: Medium]
[+5 Perception
1 Random Silver Skill
1 Random Silver Reward]
He certainly didn’t expect to meet Lily from How I Met Your Mother. Her presence in this apartment also allowed him to understand exactly where in the timeline the story was. The first half of season two, where Lily and Marshall were still broken up.
Interesting, he thought even as he picked Perception, which was always a valuable stat. Then he returned to Caroline, still on the couch, muttering dazed. “So, where were we…”
Caroline moaned.
It was a good night.