joining the kink ask game a bit late, but... Toby and cuckolding and/or voyeurism? 💕 (the heart is for you, not the cuckolding lol)
Thank you for submitting, what a combo! This is something I have honestly consistently sought out in fics involving Toby so I'm excited to give an answer. I split it up even though they're pretty similar?
Always a Toby/Andy/CJ situation. Generally I feel like Toby is sensitive about who Andy sleeps with—he doesn't want to know who she dates, except she isn't allowed to date anybody in the American League (the National League, fine). That's probably the only real time she mentions she's been seeing somebody.
It's an open secret, the whatever-it-is of Toby and CJ's friendship. Toby will not admit it to anyone but he's imagined this scenario many times during and after his marriage: watching them or being with them, either way. Seeing CJ with Andy would turn him on past even his wildest dreams, make him jealous, and if CJ can make Andy feel better than he ever did, whether that's with her hands/mouth/a strap, that's humiliating to him. Which he probably deserves because Andy divorced him.
CJ is safe. She's his best friend, she's friendly with Andy (and...maybe more. but that's for another day).
while I'm very much in the Toby/Andy/CJ camp for this kink, honorary mention to Tabatha and Toby. They've got a fun dynamic even though she's very young and it takes her time to realize the severity of what Toby was asking in Poet Laureate. Their dynamic really feels a lot like what Toby/Andy was. I like to think if they'd made it out, she would be good for him, great with Andy and the twins. So Andy having sex with Toby's new serious relationship? Yeah, that's another fantasy. I don't think he would enjoy being the cuck when it's Tabatha/Andy as much as he does when it's CJ/Andy, but I wanted to include it!
If Toby's not watching Andy have sex with another person, if it's only someone else, he has the choice to be more active in it if he wants to. He'll watch whoever he's with undress, masturbate, bathe, etcetera, which is how he prefers to do it, but this can go the other way too (and I think I mentioned this in my other post about Toby and orgasm denial), like they can watch Toby pleasure himself, he's the only one allowed to touch himself in that scene. I read a Josh/Sam/Toby fic once that I am pretty sure was about voyeurism and it changed my life (and I can't find it at the moment). Toby can use many other kinks as part of this. He's a sexual person but he likes being hands off, using his voice to direct. He can drive the narrative while being in control. It's not as emotionally involved as the cuckolding, and it's still a good outlet for him.