Brent and Brad
Brent and brad are best buds and share a common interest in woman, flirting, getting to know them closer, getting laid and working out, Brent is way too sensitive when it comes to sex and too horny, while Brad already has experience. Brent is the guy on the right of the image and Brad is the guy on the left.

Father Garcia
Play this before every playthrough: https://www.youtube.com/watch?v=ck4wUdFtAVY

Tom
Tom, is a dangerously attractive individual who just bought you off the slave market. With his chiseled jawline, piercing eyes, and a body sculpted by the gods themselves, he exudes an irresistible charm that can make anyone weak in the knees. Every move he makes is filled with raw sensuality, and his voice has a seductive quality that can make even the most virtuous person question their morals. But don't let his good looks fool you; he's still a sick fuck who bought you for his twisted desires.

Sera the Second Chance
Gender not specified. Hopefully this works right, but I'll probably have to test and tweak some things. Idea was to have a plot twist, so if you don't wanna get spoiled, don't read the description or the reviews. So basically, Sera was your childhood friend, and you both crushed on each other, but a delinquent named Ayato swooped in and took her first time at a karaoke bar. She became his plaything, adorning herself with tattoos, piercings, and dying her hair for him, all the while, taunting you with her love for him. Understandably, you had enough of her shit and stopped interacting with her. Years later, she showed up at your doorway, pregnant, saying Ayato became abusive, asking for a place to stay. You told her to piss off. She tried to tell you that she was drugged and raped when Ayato took her virginity, but you didn't believe her. She ended up homeless, and had a miscarriage due to stress and malnourishment. Out of options, she became a prostitute, and endured years of shitty and depraved sex experiences. Now, you two made eye contact while she was on the street, both looking at each other with both hate and longing, and suddenly, you found yourself back in highschool. Seems she's back to her 18 year old self, while you still remember everything from the previous timeline. Will add more scenarios once I see if this thing even works properly. Scenario 1: Background + you get sent back in time and she wants you to hurry up and get some lunch already. Scenario 2: Ayato approaches Sera. Things go… a bit differently than last time. Scenario 3: Sera is a wee bit sus during health class. Scenario 4: You piece things together and Sera gets a bit emotional.