A Bonus Weekend
Setup: Protagonist is a hard-working analyst, usually buried in analysis and possibilities. Originally I was thinking of the protagonist as a man, but now I'm also thinking of a woman option, so see farther down for that idea. Somewhat shy and geekish, he has just completed work and assisted with a presentation to a major customer at a conference on a resort type area. His boss is very pleased with the young man, and wants to reward him. Knowing that he doesn't have much of a life outside of work, he decides to give him a special bonus: "I'd like you to take a weekend vacation here now that the meeting is done. I know you're interested in history, so I've hired a local tourist guide to show you the sights. You can tell me all about it when you get back up to Chicago. No objections now - you've earned it and you need some time to decompress." Little does our geeky hero know, the tourist guide is a rather special one. One that his boss has enjoyed before. Pricey in that besides a weekend-long tour of the sun-bathed islands, the guide also offers rather more intimate services. Her job is help bring him out of his shell, show him a good time around the place, and send him back home singularly relaxed.
Style: Slow, visual start as the hero is picked up at his hotel by the attractive "guide". He probably spends a lot of time just chatting with her, and keeps getting tempting chances to glance down her top or up her skirt, slowly getting him more interested. She seems unaware at first, and perhaps makes it easy for him to think that it is her open friendly nature or perhaps the local island culture that makes her have such little personal space and body-baring clothes and behavior. Maybe a trip to a old fortress, a boardwalk, a beach, etc until eventually things progress to be a little more personal.
Possible problems: Could be too passive for the player of the male character, since other than chatting with her his primary actions would be trying to sneak peeks at her or marvel at other local sights (women or otherwise). Would require a player interested in that style, or a change to the scenario to make him more active. As many of you may know, the whole "sneaking peeks" and description-heavy approach is one I mention in my On/Offs and in another post recently.
Gender swapping: Another option would be to have the protagonist be female, probably with the boss also then female. The guide could be male, and just working to draw the shy straight girl out of her shell. Or perhaps the boss is les or bi and suspects her employee might be too, and has engineered this as a test prior to trying something herself (sequel!), with a female guide who will try to confirm the employee's orientation.
I could see enjoying either role - the employee or the guide. Actually I could see myself enjoying playing a male role as the employee with a female guide, as I've had a bit of a hankering to play a guy recently.