(See the summary if you don't want to read the whole thing)
I’m a late 20s virgin who’s been on a few dates, k closed a few times, but nothing more. No long term relationships. Matched with this girl on Tinder, age 30-31 in NYC. We texted back and forth quite a bit initially, she seemed very into me (asking a lot of questions). Our first meeting was in NYC late one night at a bar when I was hanging with a couple of friends. We talked, I kinoed, she got touchy feely too, and we made out at a concert around 4 am before she had to head home. Then we didn’t see each other for 3-4 weeks while we were both traveling in Dec/Jan. She would text me things like “you give me butterflies” and “can you come with me so we can cuddle on the plane”. Eventually we just started straight up sexting. She kept complimenting me saying I was hot and smart, etc. Once we were both back in the country, I set up a date for last Saturday.
Day 1: Saturday
Met up for dinner in NYC, I paid per standard protocol. She had arranged for tickets to a play (not Broadway but rather featuring up and coming playwrights) after dinner so we went for that. I kinoed a little during dinner but nothing heavy. Once we started walking we had our arms around each other, I felt up her ass a little which she liked. During the play she was wrapped around my arm and leaning on my shoulder. So far so good. After the play I took her to a Japanese bar/restaurant and a sake bar. While walking around felt up her ass more aggressively, and pulled her into random alcoves to make out. Very receptive to all of this. Hit up a couple more bars (Irish pub, and Coyote Ugly – a lot of desperate dudes in there). Grinded for a while in Coyote Ugly. This girl knew how to work her ass. Eventually we hit 4 AM and I decided to go home (NJ) and pull her along with me. Made out for a while in some random alcove again with heavy petting and groped her in the taxi. She loved it. Gave it my best effort to get her on the PATH train – she came in all the way to the station platform where she surreptitiously put her hands down my underwear. In the end couldn’t get her on the train though.
Day 2: Sunday
Some more texting Sunday morning (reached home at 7 AM) and she said it took all her willpower to not get on the train with me. She also said she thought I would have been more aggressive last night. Eventually just straight up told her to get a train and come visit me. She agreed and showed up around 4 PM. I kept texting how we were gonna fuck and she kept saying no. She shows up at my apartment and is dog tired so jumps straight into my comfy bed. I tried to play it cool and work for a bit but eventually got in with her and made out with heavy petting. I unbuttoned her jeans, ran my hands under her shirt and eventually just got off the bed, grabbed her by the legs, and pulled her remaining clothes off. She still wouldn’t have sex so we proceeded to make out heavily, I fingered and licked her pussy to climax (didn’t know they were so tight), and she sucked my dick (she was almost too good at it, wouldn’t swallow though). This sequence of events happened several more times until Monday afternoon. Had dinner at a Thai place, watched a movie together and went to sleep.
Day 3: Monday
As you probably expect, we did the same stuff again Monday morning and around lunch time. Hard fingering takes some serious hand stamina. Rubbed her clit to climax as well. Girl was shaking and moaning like crazy, eyes rolling back in her head. I had to get some work done so I made it clear we had to part. She still didn’t want to have sex despite my best efforts – making out, licking her tits, fingering her. I tried logical stuff too like how we were 95% of the way there anyway but of course that did jack. Rubbed up on her with my erect dick put her hand on it, still no effect. She said she didn’t want this to be a fling, and that she’d had plenty of flings before and that sex made things ‘complicated’. Major red flag for me. A couple of times I just got out of bed to grab my condom but she wouldn’t have any of it. I got out of bed, showered, and turned decidedly cold to her. She asked if I was mad – I said no, just frustrated. She said it was a ‘frustrating process’, whatever that means. In reality, I was just mad at myself for not being able to push her out of her arbitrary and illogical ‘sex rules’. We had lunch and I dropped her off at the train station. She had previously said she’s busy for the next two weeks and going to a bachelorette party in the Dominican Republic so I wouldn’t see her for the next 3 weeks. She made the bachelorette party sounds pretty tame (the girl getting married is Muslim) but who knows what’ll happen.
Did everything except sex with a 30 y.o. girl from NYC. She refused to have sex because she didn’t want it to be a fling (even though we’d met in December, texted a lot, and she was staying over at my place). She said she’d had plenty of flings before and thought we were more serious. She admitted she loved sex (blamed on her hormones). I don’t see long term potential here, though I never made things clear to her. She said she hadn’t dated recently, but I get the feeling she’s been around the block a few too many times and now wants a ‘nice guy’ since she’s hitting 31 this year.
1) Is texting for 3-4 weeks between meetings bad protocol?
2) Was meeting at an expensive-ish place for dinner and paying for it a bad idea?
3) What could I have done differently to get her over that mental block about putting a dick in a pussy? Apart from ‘be more alpha’. I suppose this also comes down to being somewhat successful (student at a top university) that makes 30 yo women want to withhold sex. Am I destined to fill the beta provider role here?
4) Should I just make it clear that there’s no long term potential? Am I being over judgmental of her sexual past that I admittedly don’t know a lot of details about?
Sorry for the length, and thanks for reading/comments.
EDIT: Thanks everyone for taking the time to read my lengthy account and write up detailed comments. I've taken copious notes and will work to internalize the advice you've given. Thank goodness for TRP.