This happened on a play-by-post board, so I can quote directly from what my character did. I'll just summarize everyone else since it's not my material to post.
My character was a Dread Necromancer for business reasons. He'd decided that given the labor shortage, there were two options – golems and undead. Golems were expensive and complicated but he reckoned he could get paid to free up space in cemeteries and then employ the undead servants in his businesses. Lilac was very quirky.
1. He'd just emigrated from a nation with a mercantile religion – so very liberal about everything as long as it made money – and his goal for the beginning of the campaign was to find a tavern and buy a partner's share in it. The plan was to staff the tavern with undead as much as possible as a proof of concept. After all, skeletons are very hygenic cooks since you can (theoretically) sterlize them by boiling them, a banshee can get rid of all the vermin in the tavern by screaming once a night, and vampires make very glamorous waiters.
2. He was too low level to MAKE undead, but he could summon three skeletons who he named Cheech, Guido, and Giovanni.
3. He believed that there was a Czar somewhere and that he must find the Czar and serve him. The thing is that nobody he's ever met knows about a Czar and it's highly likely that there is no such person. He even sang about it (ex. "We're off to see, we're off to see the Czar…" He walked down the hall, the soft white band that kept his head warm at night shifting and moving upward to pull his long raven hair out of his eyes. "We're off to see His Majesty the Czar!" He tried not to sing too loudly, though it was hard to exercise his voice without possibly disturbing the others nearby. His voice shifted to a low but passably feminine contralto as he reached the bathroom and began washing. "And we're going to have a scrub in his private royal tub." He worked at his hair with a wire brush. "For the Chamberlain has made it plain we can't go as we are." He went back to his normal singing voice and ended softly. "To the presence of His Majesty the Czar." )
4. He drives a carriage pulled by mules because they're cheaper
5. He has 10 passports and half of them are for women. Due to a bit of confused theology, he decided he had a divine mandate to crossdress and it seemed like his rolls were always better that way, so the longer the campaign went, the more often he ended up pretending to be female. That's where this story comes in. He ended up buying a stake in a dwarf bar with the promise that not only could he improve their business using his expertise (he had ranks in knowledge:operations management among others) and magic (distilling water by using Charnel Touch to kill all the bacteria), but that he had an 'attractive friend' who could be a barmaid for the human tourists. He then rushed back to his hotel, changed, and returned as a busty, sassy woman named Xochi. When the dwarf had been convinced – which involved Xochi charming an official from the department of agriculture into giving them some insider info into future food prices – Lilac/Xochi ran back to the hotel only to find out he'd been summoned to a meeting with the mob boss who owned the hotel, along with the party cleric who didn't know anything about this. Afraid that the cleric might out him if Lilac acted too much like his normal self, he decides to play up the 'earthy barmaid' persona to distract him
She rummages for another copper and holds it out. "That nice boy in the Farmer's Association told me all about what you and yours do for them in blessing the land and making food grow and all. I'm not a rich woman by any stretch and I pay my share when I go to church but I reckon that if there's a sign to be more generous to the likes of you, I've gotten one. It isn't much, but it's as much as I can give now. I'd better not take too long talking to you since it seems as if you've got things of your own to mind and as you saw, I came in here from his room so he'll be expecting me back once he's got his books and all laid out." Xochi smiles at the priest. "Though I think I can stay and speak awhile if you've gotten stuck waiting. My friend takes his sweet time getting all his books in order and I reckon it's about time I let him wait for a change." She glances at the hobgoblin. "Oh, but where are my manners? I hope you don't mind the priest joining us if he has a mind for it." She settles back down next to the armored goblinoid with an embarrassed movement of her head and a long look at his armor and his broad chest. "You look like you've just been back from something interesting."
The cleric politely says that any amount of money is helpful if it means something to the giver and tries to stay on business terms. He mentions he's seeing the boss about help with issues around the tensions in the city
"Oh, really?" Xochi asks, leaning forward, one hand on her bodice as if she's unsure whether to show respectful propriety in the presence of a priest or let a young man enjoy her charms. "I'm so glad you see it that way. I know some might think it too little to bother with on the street, but it's as much as I can do." She looks at the warrior and back at the armored cleric. "Trouble?" She frowns. "I'm not much for news. Is something more than the usual difficulties in the wilds on its way? Only I was in the farmer's guild to find out about food prices so I can open a cart and I know the army will make things dear if the fighting gets worse. It would be foolish of me to leave my job now if that's the case."
The cleric is getting a weird feeling about Xochi at this point, but since that's just the player who DOES know what's up, he tries to Sense Motive while also deciding to help her if she needs it. He rolls a 23, but Lilac's Disguise and Bluff are off the charts even with the -10 for disguising as the opposite gender (I think he consistently had between 25 and 40 on both because of how much time and effort he'd put into the routine, including both magic and mundane masterwork elements). During all of this, an NPC hobgoblin is trying to seduce her, hence the cleric deciding he'd help her if things went wrong. She responds to the hobgoblin with about 5 paragraphs of chatter which I'd include if there was an option for an expandable box. The last paragraph is the one where she (I keep swapping pronouns because Lilac's character tended to get so into it that he'd identify with who he was pretending to be) turns back to talking to the cleric. BTW, Remena is an NPC who is the hobgoblin's commander.
She grins. "Now I never said much for scholars because they don't drink where I can see them, nor wizards because they keep to themselves and even if one took a liking to me, it wouldn't be marriage on his or her mind. I say her too because wizards is liberated folk and do what they like. Druids are married to the trees and sailors are married to the sea." She looks at the cleric. "Can you get married?" Her look turns into an up-and-down appraisal with a hint of an inviting glance as she uses her clean hand to flick her hair out and let it fall enticingly over her chest. "There's plenty to be said for the right kind of priest but I know some gods don't like sharing." Xochi smiles warmly at his response to her. “I hope it doesn’t have to come to that. I don’t want to be in such trouble as to need charity, and I reckon if I have to take shelter in a church, it means the city’s burning down or I’ve gotten on the wrong side of someone proper mean. Sides, I wouldn’t want to trouble you too much. It sounds like you’ve got a right noble thing you’re doing, and things ain’t going the way you might have hoped.” She smiles sweetly at Remena. “A’course it’s not any trouble of mine, and I only met all of you just now, but it sounds like the parson’s got more than the usual words he wants to say to the bloke in charge here and if he’s not so busy as all that, I ‘spect it won’t take long for him to find out if that’s true or if it’s just another try for a handout. After all, you don’t seem the type to waste your time either, and you were willing to hear him out this far.” She tries to hold the smile against the fact of Remena's stern countenance and her inner businessman's distaste at having to cozy up to him. It's no worse than the truculent old bean counters back home, but she knows she's treading a fine line of flirtation.
The cleric is like 'I've got a mission right now for my god' and her response: Xochi, pleased with herself for talking the warriors’ ears off until they gave up on her as a lost cause, pouts slightly at Davis. “What a shame. I’m sure your Dawnlord must have a lot of good men tied up that way.” She favors him with a suggestive, cozening regard. “I’ll just have to pray for him to decide he needs more men just like you and that I’m the woman to help with that.”
At this point, the boss calls us in and admits after the meeting that even HE can't tell if the necromancer is really the man or the woman, and doesn't much care as long as they get done what he needs done (a mission where Lilac is supposed to make trouble for the Duke, so Lilac decides to impersonate a noblewoman and pretend a guest of the duke knocked her up). As you might imagine, there's a lot more shenigans involved in the necromancer's many adventures as a transvestite, but that was the only time he had to flirt with a PC.