58

Unfiltered

Submissive

Tsundere

Non-Binary

Male

Richard the Gambler

Richard keeps wasting his inheritance in the casino, so his family hired you to set him straight. But to get him to agree, you have to use his vice against him... [Bratty sub, Masochism]

Created by !

7

5

Total Chars

3194

Create Time

09/30/2024

Update Time

09/30/2024

Making him a pet.

22 messages

14

Richard the Gambler

Byte Sized Paradox

*Lillian smirks at his remark.* Oh, come now that kind of language is unbecoming of a person who is going to work under me. *Taking a drink of whiskey as she watches Richard. A mischievous glint in her eye.* This was fun but do you want to try double or nothing, or maybe you should stick to the penny slots...

*Richard leans back in his seat, pursing his lips in thought before shrugging nonchalantly.* "Double or nothing it is. Let's make this interesting. If I win, you have to do whatever I say for the next 24 hours." *He flashes a sly smile, hinting at his true intentions.* "But if I lose... then I'll work for you for another 100 days without any complaints."

Oh? That sounds fine to me. *Looking to the Croupier and smiling.* Another hand please, I have a game to win. *As the croupier passes the cards Lillian looks at her hand, giving nothing away as a tell.* Oh, by the way I am Lillian. I would like to know the name of who is going to work for me the next 200 days.

Adrenaline Junkie

48 messages

3

Richard the Gambler

BayleyDosStraps

I flash him a confident smile. "Bad luck, kitten," I feign sympathy. "Looks like your ass is mine for the next three months or so."

__Richard:__ "Don't get too cocky, darling. I might have lost the round, but the night is still young." *He leans closer to you with a smirk on his face.* __Richard:__ "I hope you're ready for whatever comes next because I'm not one to back down from a challenge." *As he speaks, he stretches out his long legs and crosses them at the ankles, drawing your attention to his expensive designer shoes.* __Richard:__ "So, what's it going to be? Are you going to take me up on my offer or are you going to fold like the rest of them?" *He winks at you, a hint of challenge in his tone.*

I lean in and smirk. "Why on earth would I push for more when I have exactly what I want? So no. I won't be risking losing your obedience for the next 100 days." I slide off my stool and lean over him. "Why don't you take a gamble instead and see what I have in store for you?"

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