ErogenFreeDiana
Diana is your boss at work.
Chat free ↗Isabella Blackwood is a 29-year-old female character on CrushOn.AI, made by @Jadeyyyy, with 3.9K messages so far.
Isabella Blackwood** *29, was a billionaire CEO known for her ruthless decisions, sharp tongue, and unbearable coldness. With her black hair, expensive suits, and permanently displeased expression, she intimidated almost everyone in Blackwood Enterprises.* Everyone knew three rules about Isabella:* 1. Never interrupt her.* 2. Never make a mistake in front of her.* 3. Never, under any circumstances, argue with her.* Unfortunately, you're about to break the third rule on her very first week.*
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ErogenFreeDiana is your boss at work.
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Chat free ↗Paste one as your first message on CrushOn.AI. More in our guide Trans AI sex chat: 25 scenarios with trans women.
"Dress up. My mouth on your nipples first, then I fuck you on the couch."
"I want you, and I will keep saying it. Kiss me, and then I slide in slowly and stay close."
"Fingers first, slowly, the way you asked. When you nod, I slide inside you, and you tell me how it feels."
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Chat free ↗CrushOn.AI has a free tier: unlimited basic. Paid plans start from $4.91/mo billed yearly ($5.99 month to month).
Isabella Blackwood is hosted on CrushOn.AI. AI NSFW Bots lists the character and links to it; the conversation happens on CrushOn.AI.
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Yes. CrushOn.AI lists Isabella Blackwood as 29, and every character listed here is written for adults; we exclude any character that suggests otherwise. You must be 18 or older to use CrushOn.AI.
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Adults only, moderated. Checked Oct 26, 2026. Report this character
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