Not Sure How To Proceed With Older Woman

I met this lady through work. She started a few months after me and for her first 2 weeks there we would take the bus home together. She would always blush and laugh and always wanted to talk to me. At first, I wasn't into it at all. Shes ~15 years older than me (20/35) and at first I wasnt physically attracted to her.

Conversation and humour flowed between us easily and always. I opened up to her about the state of my life. I told her how I was distancing myself from my friends, as I was rejecting their substance fueled, party lifestyle, I told her about my relationship history (none!) and my relationship with my family, to which she deeply related to.

She mentioned hanging out quite a bit at the start, but by the time I suggested I come over 'for wine', she hadn't brought it up in a while. So I go over, expecting nothing. I don't mean I didn't have expectations, I mean that I expected we would not become romantically involved. I expected this because I thought I would prevent such occurrences.

As soon as she opened the door to her condo all my defences vanished and she became an extremely beautiful girl. I'll never forget the words she said that paved the smooth runway for us to make out. "So do girls your age find it weird that your a virgin?" "Yea, I think so. They usually don't believe me or think I'm a bit of a loser." "Well girls my age think it's really intriguing. What if I wanted to take it?" heart pounding, not sure what to say "Lets go bang!" "hahaha.. So that's never worked on a girl your age?" "I've never said that before..." "So what, are you just, like, waiting for a girl to pounce?" "I'm waiting for you to pounce." I close her patio door, which she has told me not to several times "I'm gonna kill you" she says. "I'm going to kiss you". awesome make out times "Pretty smooth for a virgin" she says as we end the night.

That was ~3 months ago. We've never had sex. We've only done anything involving those organs once. (The second time we hung out) and it freaked her out so I never pushed for it again. Whenever we hang out it's like a magical sensual journey and we do it all without touching that area (on either of us). It's pretty awesome.

We've 'ended it' twice now. The first time was my doing. She kept getting anxious the day after we'd hang out (usually a friday), and she'd get migraines all weekend. We'd talk and talk about how someday she'll be 40 and I'll be 25. About how if only I was older. She humoursly summed up our situation "It's like theres a flag on the play". I jokingly suggested she enter a cryogenic chamber on her last period before menopause so as to preserve an egg. So I said we should just be friends, because although I was "winning the battle" against her future based focus and anxiety, I was tired of fighting (maybe I gave up too soon!?).

Eventually we go to a work function and she gives me a ride home. Obviously she comes inside and we start a more intense relationship using the word "dating".

This time it ends in tears the day after I said "I love you". Again, I ended it, as I was freaking out.

We've just kinda started up again, really organic like, we were just both kinda sad about it so she was just like "come over" and I did...

The reason it's so hard for me is this:

I love her personality and I'm really sexually attracted to her, but I worry about the distant future (~2-5 years from now). Things like having kids and travelling just don't make sense to me. I think I could totally date this girl for 1 or 2 years, but I can't imagine myself wanting to like have a kid and buy a house and "settle down" within that time. I am afraid of having a 1 or 2 year relationship with her because ending it might crush her. It might crush me too, but I'm young and have time to kill. I don't want to 'waste' these vital years of hers. The real kicker is that I still have an interest in younger girls around me. I would love for her to be my first time, as well, but she needs a "real" relationship for that to happen. I worry about not finding a girl as affectionate, nurturing and quant as her. My history of failure with women makes me attached to her. I think I want her to find an awesome man her age, and I the same, but I just worry about what could have been, and I still wish that she could have at least been my first time... We're supposed to hang out today for my birthday being friday (we got together briefly on friday), and I'm not sure what to do