Just stuff I like with added comments

date night idea:

leave the key at home. you won't be needing it.

take him out on the town, caged of course. get a hotel room for the night. one with a view 😏...

let his anticipation build all night by saying things that let him know what is going to happen when you two get back to the hotel room. make him feel wooed. start with small things like,

I can't wait to get you back to the hotel...

i've got a big night planned for you later.

hope you're in the mood later for some fun.

treat him like the woman on the date. pay for the food/drinks, open the door for him, order for him, etc.

smack his ass when he walks pas you

as the night progresses and (if you drink) as the alcohol starts to flow, say more explicit things

as soon as we get back to the hotel i want you naked and your tongue between my legs.

i can't wait for you to go down on me.

I'm going to be doing the fucking tonight and you'll be my bitch.

order him girly drinks and tell him that if he's going to get fucked like a girl tonight that he better start drinking like one now.

hope your ass is ready

wonder if anyone will see me pegging you when i "accidentally" leave the window open.

do you think you could cum from anal? let's find out!

get him back to the room and command him to get naked or command him to get dressed if you want him in something sexy.

take command. tell him he's the bitch tonight. make him go down on you until you're ready to move on.

make him get down on his knees to put your strap-on on you and secure it tight. don't let him stand back up. make him lubricate it too by giving you a wet blow job. joke that his saliva is all the lube he will be getting unless he does a realistic job (it won't be, but joke that it is). tell him to suck your strap-on like he wishes you would suck his dick.

once you're done with that, bend him over the bed. start slow and peg him gentle. slowly progress to more aggressive fucking.

stand him up and push him toward the window (if there is one) and peg him in the window. tell him to enjoy the view. laugh and wave as if someone saw him.

having trouble thinking of what to do next? just ask yourself what he would do to you in the same situation. do that.

be dominate. be confident. this will be a date night you will both remember forever.