I have been summoned by
@SW15 and
@Clockwerk50 .
First off, I'm confused...
@CornbreadFed said you got sex and to be happy, but all you did was finger her, right
@Oatmeal31 ?
Anyway, my situation was quite different because I matched with a flight attendant on a dating app and ended up driving a little less than an hour to meet up with her at a bar, stay the night, and f***. She lives there, travels for work, and has a roommate.
Your situation involves a tourist who may or may not be back to visit you and is staying in Chicago alone.
For starters, I'm amazed this went as well as it did; double-texting that you needed to hear her Australian accent again, "darling", "high five", asking a total stranger who is there by herself to get into a car with you, drive more than an hour away, and walk out to a beach at night where you're the only ones there? Holy hell, dude, even as a guy, if a girl offered that to me for a first date, I'd think I was being set up to be murdered.
Second, are you SURE you gave her an O? When it comes to fingering, MOST of the time you can sorta tell if she: A. suddenly clenches super hard on your hand like her vag is gonna break your bones, B. you feel a warm rush in addition to how wet she already was, C. straight up starts squirting, or D. her legs start twitching uncontrollably and the rest of her muscles lock up. THAT'S how you know you got it, otherwise she can get as wet as she wants and scream as much as she likes - she could be faking it, or she could be enjoying the hell out of it, just not necessarily having an O.
Third, when she said "that seems like all you want to do" when it came to the kissing had one of two meanings: A. "that seems like ALL you want to do" means she's disappointed that all you want to do is get physical with her rather than talk, hang out, spend time with her, whatever, or B. "that seems like all YOU want to do" means she's down to go further, you just haven't made the move yet. I'm assuming it was the former, since the way this reads sounds like you didn't end up having sex.
Fourth, "I joke about how she's guarding the castle and I might have to break through the gates with an army"...
...
...I shouldn't have to explain why this is bad, but just to be clear, this is a half-truth in the form of a joke. You're communicating that you're desperate for sex from her, and that you feel like you're trying too hard, joking that you have to try even harder. Don't do that.
Otherwise, I don't think there's too much you did wrong here. It sounds like she was interested, just not interested enough to have sex with a total stranger while traveling. She was down for a little fun, just not too much. Your text messaging and comments like the one above probably painted you as a bit needy, which might've turned her off. You may also be jumping the gun, and she'll end up texting you back later on. She may also be lying and had no intent on visiting again, but wanted to give you a mental fallback so you didn't feel like you HAD to get all the way to sex before she left and never returned.
In the future, I would probably suggest just grabbing drinks with her somewhere nearby. You don't have to go on this whole multi-hour journey to end up sober on a beach with her, where she's wondering if she's about to get murdered. You can just go to a bar, show her you're fun, then go back to one of your places if the night goes well. Here you spent at least 2 hours driving, however many hours at the beach, and the night didn't end in sex - you probably feel like you wasted your time, and I'd agree. I'd save that romantic sh** for date 2 or 3 after you've already smashed and she shows she's worth a little extra effort on your end.