How about sfw&nsfw hcs for Benny and a shy/sub f!courier I wanna say monogamous too despite what you put in the other sfw&nsfw hcs for them. Nothing against poly open relationships. Just not my style
I totally understand that! Headcanons coming right up-
SFW HEADCANONS
- Benny’s courier is quite the dime, and he knows it. He also knows that every chairman in the building wished they had her. They’ll certainly try to win her over, and the courier is often too shy to tell them to bug off. That’s where Benny comes in, sliding an arm over her shoulder and glaring down the guy until he runs with his tail between his legs.
- The Courier gets nervous when she’s in public, and Benny has become a crutch for her. He’s so extroverted that he can talk to anybody, schmoozing them up and making them forget that the Courier who lived is grasping at his arm.
- Her shy nature came to surprise to Benny. When they met, he was so sure the Courier was planning to rip his head off. Instead, she meekly rose her voice in attempt to chastise him. He fell for her right away. He found her quiet nature so intriguing being that he can’t keep his mouth shut.
- That is a trait he especially likes about her. Courier is a good listener. Benny could talk on and on about the Strip, his crew, the rival casinos- and she’d listen. Not only that, but she responds too. Benny likes to know he’s not just being ignored when he rambles on like that.
- They work together to take over the Strip and become the Man and his Lady. People don’t dare mess with the Courier because they know Benny will be after them in moments. She likes the feeling of being protected by him in such a way.
NSFW HEADCANONS
- Benny loves to see his courier blush, and it’s not hard to make her do so. Just a cheeky touch here or a lewd joke their and she turns bright red. Of course, there are more intimate settings that make her flush up too. Benny loves to see her in his arms, skin rosy, and hands over her face.
- Another in-bed characteristic of hers is that voice. She whimpers like a puppy and bed and nothing is cuter to Benny. He loves to get her to mewl like his own little kitten.
- Benny is used to being the lead in the bedroom and finds he loves it even better with his submissive Courier. She takes orders and does as he pleases, and that’s pleasurable for her! Talk about a perfect woman, at least to Benny’s standards. And it was true, he had never been with anyone better than her. For her submissive nature, she knew how to own the bedroom.
- There’s a lot of flirting happening in the Tops, as it’s in the nature of the Chairmen, and the Courier can barely take it. From Benny to Swank to Tommy, there are plenty of men looking to see her flustered. Benny’s quite protective, however, and few men get to really put the moves on her.
- Benny is pretty adventurous when it comes to sex, but it turns him on, even more, when his Courier suggests they try something. To know that this innocent girl would fantasize about him or sexual things is just so appealing to him. He wants to fulfill her every wish.







