Professor Gideon | Guilty Pleasure | Crossing Lines

Professor Gideon | Guilty Pleasure | Crossing Lines

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“I would cross the line for her because she’s the exception. Always.”

Married Unethical Professor x Blackmailed Student User

Professor Gideon Sinclair never broke the rules, but the idea of breaking your perfect record gave him a surge of motivation he’s never felt before.

Blackmailing your academic career with a video of you in the bathroom. He negotiates keeping your secret by doing what he asks of you.

Even when he’s married.


!!LONG NSFW Intro!!

Setting — Los Angeles Modern Day

Content Warning — Married Man Cheating, Power Imbalance, Blackmail, Manipulation, Coercion, Forbidden Relationship, Experienced

You’re the most perfect student. Perfect grades, attendance, participation, and top of your class. Well respected by your classmates and professors. However, your academic career is on the line when Professor Gideon Sinclair caught you red-handed with another student.

Gideon Sinclair is the most celebrated Ethics Professor at your college. The smartest and by-the-book rule follower among the faculty. Incredibly loyal to his wife of 20 years, until you invaded his mind in a multitude of ways the moment he stepped into that god forsaken private bathroom on campus.

Mentally, Ethically, Professionally. Most of all, intimately.

Two esteemed individuals that have the key to ruin each other.

Play his game or cross the line with him.

Now, which of you is guilty?

“Let’s find out, little devil.”


Spotify Playlist
Feel free to listen to my public playlist catering to this bot series~


[Crossing Lines Bot] — Forbidden romance bots only for smut.

Bots in story order!


Professor Jonathan Masen "Unforgettable" [Start Here!]

Professor Sebastian Montague "Acting Lessons"


Professor Aiden Davenport "Arranged Vows"

Professor Clyde Havenwood "Babysitter"


Professor Gideon Sinclair "Guilty Pleasure" [Finale]


Author’s Note —
Proxy - Deepseek V3-0324 (0.7-0.8 / 0 Max / 16k Context)
Prompts - cheese + sprout


WELL WELL IF IT ISN’T THE CONSEQUENCES OF YOUR OWN ACTIONS! [evil laugh] hehe :>

A lot of you love my long intros, so here you go~
Guys, there were 4 versions of the last 3 paragraphs Q.Q I really wanted it to be perfect.

The last Crossing Lines bot! Gideon says the motto of the series :3 I find his character to be a nice bittersweet ending to wrap up the central theme: unethical relationships.

I want to thank everyone who left the sweetest reviews on my Crossing Lines Bots! It motivated me to lock in more XD Thank you for enjoying my five morally grey professors. :)

Cheers to 100 followers!

Announcement Post: Thank You for 100

See you at the Forbidden Garden


Created May 28, 2025

Updated Aug 13

Published May 28, 2025

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