Violet's Flashback: Meeting Toby

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~6ish years ago~

It was day three in holding when Toby visited, all decked out in a designer suit with a posh leather briefcase. "You must be hella expensive," I snorted, glancing down at my tattered orange jumpsuit as the guard closed the door behind me.

Toby plopped the briefcase onto the metal table, opening it and motioning for me to sit in front of him. "I am," he said without glancing up from gathering folders and paperwork. "Molly, however, gets the friends and family discount, which is why I'm here instead of an actual lawyer."

I stopped pacing to look at him with a cocked eyebrow. "You ain't a lawyer? The fuck are you then?"

"A trial scientist."

"Whatever the fuck that is..."

Now he made eye contact, intense enough to make my stomach drop, then closed his briefcase and deposited it onto the floor. He tossed the folders onto the table now, brown eyes still locked with mine. "Molly warned me you'd be difficult," then shook his head. "I'm the person who's getting you out of this mess." Pen in hand, he clicked it and opened to a blank page in his yellow tablet. "Tell me everything, in as much detail as possible, no lies or omitting information. Everything is relevant and will come out one way or another."

"You know I've been workin' with a lawyer the last couple of months and know all that shit by now," I sneered.

He didn't respond, only waited for my story.

That's how it was the first few times I met with him: my snarky comments, his silence until I complied with his requests, some curiosity about each other (since I suspected he was into the lifestyle, even though nobody had blatantly said so), but not getting too personal. Eventually the judge agreed to place me under house arrest until trial.

Toby kept a close eye on me, calling or visiting almost daily to make sure I was following the conditions of my release (also to flirt with Vic, but I hadn't realized it at the time). Sometimes he met me at school and we walked home together, sharing stories from childhood or failed friendships. That's how we started getting real chummy, blurring the lines between friends and professionals.

You know how the doc is – he'll let everyone else talk and never verbally contribute to the conversation. Ha, that's what makes him a good shrink I guess. But I like to ask questions, sometimes "too personal" (whatever that means), and I've been told that I don't know when to stop.

Despite directly asking him a hundred times if he's into spanking, I never got a direct answer. I guess I like talking about myself too much. I described punishments I'd received over the last year in dramaticized detail, trying to engage him in conversation about it. Always ended up in some kind of psychoanalysis of me, unrelated to spanking.

He did share other tidbits about himself with me, though. Like he's from a dysfunctional family, took care of his lil sis a lot, which is sorta how he first related to Vic.

Actually he and Vic instantly connected. They met before Toby came to see me in jail, introduced in person by Molly. When I saw the two of them together, I realized why Toby was so invested in me — he empathized with Vic. He had to take care of his sis in the same way Vic cared for me. He'd experienced the same fears and anger and love. He swooped in for Vic, just like he'd wished someone had done for him (I can do some psychoanalyzing of my own now, too).

It was a few days before my trial when I finally just asked him to give me a spanking.

His response? "This is a strictly professional relationship, Violeta."

I furrowed my brows. "Is it? You're in my crib, you know my fam, we see each other practically everyday. Sounds to me like you're a..." I gasped for effect, "friend!"

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