The next morning, Ryan's system greeted him with new updates.
[Daily Missions Refreshed]
[Main Mission: Make a Date with One Active Target – Reward: +1 Confidence, $1,500]
[Bonus Mission: Increase Intimacy Level with a New MILF – Reward: Touch Upgrade II]
[Side Quest: Gym Encounter – Vanessa Progression Pathway Unlocked]
[Hint: Timing is everything. She visits the gym between 10 AM – 11:30 AM.]
Ryan checked the clock. 9:52 AM. Perfect.
He suited up in a new athletic outfit—black compression shirt, navy joggers, and the same charming cologne. He even packed a water bottle and towel to keep up the disguise.
The gym was quiet when he arrived. A few regulars were there, but his eyes locked onto the familiar figure of Vanessa stretching by the mirrors. Tight pink leggings, loose tank top, high ponytail. Stunning.
[Target Detected: Vanessa – Gym Trainer – MILF Status: Confirmed – Flirt Level 1, Trust Level 0.5]
Ryan took a mat beside her again, pretending to stretch casually.
She glanced over. "Well, if it isn't the newbie. Back for more?"
He smiled. "Couldn't stop thinking about your technique."
She laughed, a little louder this time. "Flatterer."
[Flirt Registered – Level 2 Achieved]
They stretched side-by-side, and Ryan matched her tempo. She corrected his posture once, placing her hands on his back. He let the contact linger.
[Touch Registered – Progress: 20%]
After a set of planks and lunges, she stood and offered, "Want to try something more fun? Partner squats?"
"I'm game if you are."
Vanessa stood behind him for support. Her hands found his waist as she guided him through the motion. Their bodies were close, and heat built between them.
[Touch Level Increased – Progress: 45%]
[Trust Level: 1 – Conversation Path Unlocked]
During cooldown, she grabbed her water bottle and leaned on the railing near the treadmills. Ryan approached.
"So, do you train full-time or is this just a passion project?"
"A bit of both," she replied. "I do online coaching too. Fitness is my therapy."
"I can see it. You look amazing."
She raised an eyebrow, amused. "Careful, Ryan. Keep talking like that and I might offer you private lessons."
[Event Triggered: Private Training Offer – Vanessa]
[Mission Progress: 70% – Make a Date Trigger Available]
He leaned casually on the railing beside her. "Then let me make it official. Dinner this weekend?"
She looked him up and down. "You've got guts. Alright. Saturday night. But you better still show up here tomorrow morning, same time."
[Main Mission Complete – Reward Acquired]
[Relationship Status Update – Vanessa: Trust Level 1.5, Flirt Level 2, Intimacy Level 0]
[Side Quest Activated: Vanessa – Bedroom Progression Track]
Before he left, she touched his arm playfully. "Don't make me regret it, rookie."
[Touch Registered – 80% to Bonus Mission Completion]
Back at home, Ryan was high on success. Two MILFs, both paths unlocked, dates lined up, confidence rising.
[New Feature Unlocked: Parallel Pathways – Multiple targets can now be pursued concurrently. Relationship levels remain independent.]
[Upcoming Unlock: Harem Synchronization (3 Targets Required)]
His phone buzzed. A message from Olivia.
Hey… I was thinking about our talk last night. Want to join me for lunch? Just something casual?
Ryan smirked.
[Opportunity Detected – Olivia Side Event Triggered: Daylight Date]
He opened his closet. "Time to multitask."
Ryan picked out a light gray button-down and dark jeans for the casual lunch Olivia had invited him to. He sprayed on cologne, checked his breath, and headed over.
Olivia greeted him in a sundress—blue with tiny white flowers. Her hair was tied loosely behind her, and she looked effortlessly elegant.
"You clean up well," she teased.
"You make it easy to try," Ryan replied.
[Olivia: Flirt Level 3, Trust Level 2.5 – Intimacy Event Proximity: 85%]
She served them a light lunch—grilled chicken wraps, lemonade, and a small chocolate tart for dessert. They ate on the balcony, the warm sun and soft breeze setting a calm, inviting mood.
"I wasn't sure if you'd say yes," Olivia said, sipping her lemonade.
"I'd say yes to you any day," Ryan replied.
[System Notice: Smooth Whisper activated – +20% Flirt Efficiency]
She gave a shy smile. "You're dangerous with that mouth of yours."
Ryan leaned forward. "Only if you let me be."
[Event Triggered: Olivia – Private Touch Opportunity]
As they cleared the table, Olivia brushed past him. Her hand grazed his lower back—a light, deliberate touch.
[Touch Registered – Olivia Intimacy Level: 95%]
They paused, standing close in the narrow kitchen. Her eyes met his. For a heartbeat, time stilled.
Then her phone buzzed.
She glanced at it. "Ah… work emergency. I'm sorry, Ryan. Raincheck?"
"Of course."
But before he left, she leaned in, her lips brushing his ear. "Next time, I won't stop myself."
[Progress Saved – Olivia: Private Bedroom Encounter Available – Schedule via Text or Visit]
Back at his apartment, Ryan grinned. He checked his system panel.
[Milestone Update – Olivia Route: 100% Intimacy Prepped]
[New Mission: Schedule the Night – Olivia]
Before he could relax, a knock came at the door.
It was Vanessa.
She wore a black sports bra and tight joggers. "You skipped today. I thought we had a deal."
"Something came up," Ryan replied, surprised.
She leaned against the doorframe, arms folded. "Then make it up to me."
[Event Triggered: Vanessa – Assertive Path Option]
[Mission Alert: Active Target Conflict – Parallel Timing Encounter]
Vanessa smirked. "Wanna go for a run? Or are you too scared I'll outpace you?"
Ryan stepped out, locking the door. "Let's find out."
They jogged through the neighborhood trail, Vanessa setting a punishing pace. But Ryan kept up. She pushed harder, and he stayed on her heels. Finally, she stopped at a quiet park.
"You're persistent," she said, breathing heavy, sweat glistening on her skin.
"I like chasing things worth catching."
[Flirt Level Up – Vanessa: Level 3 Achieved]
They sat on the bench, cooling down. She pulled her ponytail free, letting her hair fall naturally.
"I like guys who keep promises," she said.
"And I like women who don't mind breaking a few rules."
She gave a sideways glance. "That so?"
Ryan leaned in slightly. "Very."
[Touch Event: Accidental Hand Contact]
She didn't pull away.
[Touch Registered – Vanessa Intimacy Level: 40%]
She stood up, pulling her hair back again. "Same time tomorrow. No excuses."
As she jogged off, Ryan stood watching.
[Vanessa Route: Heat Level Rising – Assertive Encounter Path Developing]
Back in his room, Ryan laid down with a smug grin.
[System Update: Duel Paths Engaged – Olivia (Soft) & Vanessa (Assertive)]
[Special Bonus Mission: Balance the Heat – Keep both MILFs satisfied for 3 days – Reward: Bonus Gacha Spin]
The stakes were rising. And Ryan was ready to play both games.