For the dress up suggestions, I still remember that one time you have lost a bet and your crew got to pick up a dress for you to wear-- something cute and colorful, even sent me a holo of you flipping the camera off.
I know dresses are not really your thing, but you also have not protested when you ran into me in the corridor, or when I ended up picking you up to spread you over my desk, giving me easy access to you, just hiking it up? Easy to kiss up your thighs and leave hickeys leading up to you, already hard and leaking after barely few kisses and touches.
I would love to pick out and buy a more fitting dress for you, something short and flowing, show you out, how sweet you can be, maybe even with a fitting lingerie set, a lovely garter belt and silk stockings, no panties because why reduce the access.
I'd love to take you out for a dinner first, see how desperate you can get with me teasing you all evening, and if you'd like, maybe we can add a plug or a different toy into the equation. Make it interesting.
So... when do we go shopping?