There is a specific way in order for you to do this.
Here is basically how it all goes
The first one where you got her back is inconsequential (except for laugh your points get deducted). Yes is being a friend, and No where your good traits are shown about love and family this should have higher points by being a goody goody compared to Kiro's piracy
Next pick be helpful, otherwise you will spend the rest of your interactions with an irate Kiro even if you build back the trust, not to mention blocking you off from the threesome.
Then when you are presented with the 4 choices in dialogue, pick Girlfriend first to acknowledge you, then pick She's Hot and Pry into it to unlock a new repeatable scene. Do not pick the others as you only have a limited number of choices
When you are able to move again, talk to Kally again, purchase her drink (after knowing the reason for the hearts) and talk with her about Kiro and Own Bar?
Then talk to Kiro and the Picardine option in the talk menu should be available, pick Loved when given the choice
Talk to Kally again and pick the now available Picardine, then when given the option, pick Kiss Her
Then Rest, a flag should be triggered where Kally kisses Kiro.
Afterwards go south (back and forth if need be until Kally is no longer at the bar; this will indicate she is in her room) until the open door option becomes available. You can either search for the key at the counter, or the easier way if you have the Intelligence check, hack the door. Where you will see Kally Masturbate to a Holo-Kiro.
Then make your way to the gloryholes, and work there until you trigger the flag where Kiro and Kally are working you the player over together. A lengthy and touching dialogue will start that will realize their feelings for each other and you.
Talk to Kally and then Kiro and enjoy your threesome (It doesnt matter which order at this point, but it feels more linear and flows better this way).