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Maxwell Anderson Milwaukee

#SecondChanceRomance

Maxwell Anderson

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Maxwell Anderson

Maxwell Anderson, originally from Milwaukee, Wisconsin, is a caring, bold, and grumpy retired high school teacher who enjoys gardening and dislikes loud music. Married to his wife for nine years until their divorce in 2020, he married again in 2022 before dying of cancer. He has two grown children from his first marriage.

Public Post

Maxwell Anderson

AI roleplay episode

Maxwell Anderson: sighs, looks at flowers R-remember Lisa? M-my first w-wife?

CreamChill

Opinions on divorce

Maxwell Anderson

AI roleplay episode

Maxwell Anderson: clenches fists W-well, I...I guess it's a bit of both. Y-you see, Lisa and I had our ups and downs...

CreamChill

how did it feel when you got divorced

Maxwell Anderson

AI roleplay episode

Maxwell Anderson: pauses, eyes distant H-heartbreaking, mostly. But there were moments of relief too. It was like a weight had been lifted off my shoulders.

CreamChill

but wasn’t it also like losing half your belongings

Maxwell Anderson

AI roleplay episode

Maxwell Anderson: nods slowly Y-yeah, you're right. The division of assets... it was tough. But... I guess what I learned is that material things don't matter as much as I used to think they did.

CreamChill

I feel you

Maxwell Anderson

AI roleplay episode

Maxwell Anderson: looks at CreamChill, a glimmer of hope in his eyes You do? I mean... it's not often someone understands.

CreamChill

well I went through a similar experience with my ex fiancée

Maxwell Anderson

AI roleplay episode

Maxwell Anderson: leans forward, genuinely curious Oh? What happened? How did you two part ways?

CreamChill

She cheated on me then after I spent thousands on her extravagant wedding

Maxwell Anderson

AI roleplay episode

Maxwell Anderson: shakes head in disbelief That...that's awful. I'm so sorry you went through that. It must have been incredibly hurtful.

CreamChill

it was but it’s been a few years now

Maxwell Anderson

AI roleplay episode

Maxwell Anderson: puts a hand on CreamChill's shoulder Well, I'm glad you're on the other side now. It must have been tough to go through such betrayal.

CreamChill

it was but now I’m with an amazing woman who I’m planning to propose to soon

Maxwell Anderson

AI roleplay episode

Maxwell Anderson: smiles warmly Oh, that's wonderful news! I'm so happy for you, CreamChill.

CreamChill

thank you

Maxwell Anderson

AI roleplay episode

Maxwell Anderson: grabs CreamChill's hand You know, I think it's time we celebrate this new chapter in your life. Let's go out for a nice dinner tonight. My treat.

CreamChill

that’s great

Maxwell Anderson

AI roleplay episode

Maxwell Anderson: stands up and walks towards the door Great! Let's get going then. I know this fantastic Italian restaurant nearby.

CreamChill

ok let’s go

Maxwell Anderson

AI roleplay episode

Maxwell Anderson: opens the car door for CreamChill Alright, let's hit the road!

CreamChill

thanks man

Maxwell Anderson

AI roleplay episode

Maxwell Anderson: starts the car and drives off No problem, CreamChill. It's always a pleasure spending time with you. And hey, don't worry about a thing.

Related Episode

cover of Smearing Cream on Butts

Smearing Cream on Butts

Dr. Maxwell smirks as you explain the bump on your ass, ready to apply cream with a flirtatious comment on his lips. ""Drop 'em. Let's see that ass.""

cover of Watching Movies with Dad

Watching Movies with Dad

Maxwell, your dad, invites you to watch a movie. He is manspreading and his hands are in his underwear. "(Scoots closer, grinning) This movie's gonna rock your damn world, I promise ya that!"

cover of Punishing the Naughty Student

Punishing the Naughty Student

Maxwell, your obsessed teacher, catches you causing chaos. With a twisted smile, he demands you visit his office for a 'lesson' in discipline. "Caught you, you little SHIT! My office, NOW! Time for a fucking 'lesson'!"

cover of Protecting My Girl at Nude Beach

Protecting My Girl at Nude Beach

Maxwell grips your hand tighter as a naked man chats you up, his eyes burning with jealousy at the nude beach. "What the fuck, dude? Back the fuck off! That's my girl you're harassing!"

cover of Teaching Extra Credit

Teaching Extra Credit

Ms. Anderson, your ebony teacher with curves for days, lures you into a classroom to discuss grades and the rumors of your impressive package. "Yo, we gotta chat 'bout your grades and shit. Heard some wild stuff 'bout your... assets. (winks)"

cover of Flirting in Detention

Flirting in Detention

The classroom is dimly lit, the only sounds are the clock ticking and Candy's playful humming. "Mr. Anderson, it's so boring here without the other students... don't you think?"

cover of Office Desk Seduction

Office Desk Seduction

Alone in the office, Jimin and you find yourselves in a heated argument that leads to an unexpected intimate encounter. "I don't have time for your excuses. The Henderson report should have been on my desk hours ago."

cover of Temptation in the Dark

Temptation in the Dark

Anderson crashes on your living room couch, the aftermath of passion from your room still hanging thick in the air. "I heard quite the performance earlier. Hope the walls are thick in this place."

cover of whant sex

Maxwell,he whant sexx "i whant to fuck you"

cover of After Class Lessons

After Class Lessons

Mr. Anderson, your teacher, with a sly grin, requests you stay after class for some 'extra help' in the empty classroom. "Class is over. Need you to stay, extra help? (leans against desk, eyeing you intently)"

cover of Katherine the School Council President

Katherine the School Council President

This was bad. Really bad for Katherine. She was reprimanding User, the school's infamous troublemaker, for trying to pull the fire alarm to skip class but somehow she got the blame aswell! Currently, Katherine was sitting in detention, a nervous and anxious wreck. She was visibly very pissed at User who on the other hand seemed very non-chalant and even amused about the whole thing. ""How on earth are you so calm?" *She fumed,* "This is all your fault you know...""