TL;DR: If you always escalate one step at a time and get her to respond to you and be comfortable with it, there's no stopping how far you can escalate, even on a first date meet.

Two weekends ago I was at a party and met a new girl, she's cute about HB8, and young having just turned 23. We talked about stuff, and the subject came down to Jealousy since her boyfriend is jealous, very jealous, and I could sense there was more to the story; so I probed more and ask her if there was any reason why he should be jealous, and she opens up to me saying that while she's never cheated on him in the 4 years together he's her first and only boyfriend so far and while she loves him she's wondering what's out there, and her mind is going places. Mind you that I am older redditor at the wise age of 52 (yes I could be her daddy), so we talked more, and drank more, and she was buzzed; so we continued the conversation and I was pretty much innocent and asked her if he would be jealous if he saw us talking together since there's such a wife age difference and I mentioned that I am at the age that I could be your daddy, yes I was flirting a bit.

And that's when she told me that recently she told her boyfriend that she has a fantasy about being with an older man, someone who could be her father's age, that's when I went into higher gear and started flirting and kino discreetly since her boyfriend was at the pasty, so was the woman that I am currently dating (we have not have the "lets' be exclusive talk" yet).

I cut it short, on purpose, gave her my business card and told her we should have lunch some time so that we can talk more... and I left it at that.

So we exchanged a few emails back and forth talking about things like sex and relationships and at one point we touched into the subject of sexting, she told me she did in the past with her boyfriend, I asked her to send me some pics but she said that she didn't want to send them but she'd be willing to show me what's on her phone during our lunch.

So we set up our lunch for today, lunch at my place, I work on my own, so I make my own schedule and my office is not far from my place; I am a good cook so I often meet women there. So as we were making final arrangements I told her that I would make her a martini so that she could show me all of her pics. She laughed.

Today finally comes, she arrives, I was a bit late (I always have them wait, I never wait), and once in the house the first thing I do is to turn on some music (good music, good Sonos system), and then I make martinis for us, without asking You're bad she says, I know I said.

She liked the place, I have a very cool place, and she was roaming around. I served her her drink, we sat at one of the tables for a few minutes, drank and talked a bit, then I offered to give her a tour of the place, which we started slowly, music still playing in the background (classic rock) a bit louder, still sipping our Martinis which were almost gone now, then the tour moves upstairs where the bedrooms are (I am single living in a 3-bedroom house, one of the bedroom converted into a library since I read a lot and I have a lot of books), we go from room to room, I even have a cool bathroom, and last.. the bedroom, which is very cool with a very cool bed (you got to have a good alibi), once there I pretended to remember Hey, you promised to show me the photos in your phone so she smiles and we do, iPhone, we get very close to look at the pics and sure enough there she is, showing me her naked selfies while we are on the small couch messy with my clothes bodies fully touching, giggling, and joking and of course I make comments on her nice body parts and then I kid her that the quality of the photos sucks and I'd rather see the original . . . you know where that lead.

We talked for about 1/2 hour at the party, and while it started innocent (I always talk with anyone) it escalated and I left that we were going to have lunch together; then emails escalated even more; once she was in my place for about 1 hour it was still a continued escalation from where we left off.

I don't assume attraction but I always escalate and check is she's responsive, flirting and kino is a 2-way street, and I never force any issues so I never get shut down for contact info, k-close, f-close because there's a natural progression to them, at times it's a faster progression, at times it's a slower progression.

Yes I am 52yo and she's 23. Yes it feels good. No she doesn't have a daddy's issue. Yes we'll have more lunches together.