Chicken out and go to the bar instead
From Create Your Own Story
Ah, forget it. It's not that you don't want to try this, it's just that you'll never get the courage to go looking, even (or especially) if it's with an escort. Feeling a little depressed and unfulfilled, you decide to go to your favorite bar to drink away your funk. Once you arrive at Dennis's you find the place surprisingly quiet. That's fine with you, because it means more attention from Gianna, your favorite bartender. She's a gorgeous Italian immigrant who you've known for awhile. You never pursued her at all, partly because it felt...somehow wrong to pester her at her workplace, and partly because, well, you've been kind of obsessed with shemales lately.
"You look like you need a drink," Gianna says, a little bit more perkily than you feel is warranted.
"Yeah," you answer, "just feeling a little unsatisfied."
"You're not getting any?" she immediately guesses, and you almost spit out your drink. Ah, yes, you had almost forgotten how direct she can be.
"Er, something like that." you admit awkwardly.
She leans over the bar and looks at you expectantly, and you can see more of her modest cleavage now. You sigh and give in a little. "All right, so I might have wanted to get more adventurous, and I sort of lost my nerve. I'm just a bit disappointed that it doesn't seem like it will ever happen, that's all. I'll get over it."
Gianna hums thoughtfully, then says "Maybe you shouldn't have to get over it. Surely there's someone you can trust who can at least help you..."
You are sort of touched that Gianna wants to help you out, even if it is an uncomfortable conversation. "Eh, maybe." you say noncomitally.
"You know," she adds, "I happen to know a few things about...'adventure'" she winks at you. "Maybe I can hook you up?"
You look at her doubtfully. By now, you've consumed a fair bit of liquid courage, and your inhibitions are starting to suffer. Is she...hitting on you? Just trying to give you advice? Hm, why not take her up? Not like you have anything better to do, and you do need some release soon.
"What do you have in mind?" you ask.
She looks around. "Let me close things down here. Not like anyone else is going to show up, right? We should talk somewhere more private."
Do you: