I don't want it to be too tight, that I'd feel like I was hurting her, but
The last girl I was hooking up with, had an incredible 10 body, the only chick I've been with who had fake tits (amazing), and she was really tall with loooong, athletic legs.
The first time we did it, we were laying in bed in missionary. I like for the girl to reach down and put me in. But she was so tense, that I wouldn't fit, it was actually kind of painful for me. At first I was like "WTF, I don't fit!", but I kind of grinded my head around the outside of her vagina, and I could feel her getting so wet, her thighs were soaked, she must have loosened up and relaxed, I put my head in and broke past that initial barrier, and slid my full length into her, she made the sexiest fucking gasp when I went fully into her. And then, my dick fit like a glove, better than I've fit in any girl, it was the perfect amount of tightness, and I started long-stroking her, while she gasped and whispered dirty things into my ear.
And almost every time we did it after that, it was the same process. I wouldn't fit, it would bend my dick in a painful way, she'd say something like "Your dick is too big, baby!" Which is always a sexy, ego-stroking thing to hear. But I'd work it around for a minute, fucking her with just the head, until she opened up. I liked to use that to tease her, once I felt she was ready, I'd slowly slide in and out just an inch or so, until she was begging for it and soaking wet, and then slide in balls deep. I always loved the way she reacted when I put it fully in, the gasp she would make.
It wasn't that I was too big, it was that she was so tense at the beginning, but I liked to let her think it was my "big cock".
But basing off the beginning of the sex, when she would be too tightened up, I don't think I would like a girl who was that tight all the time, I'd just feel like I was hurting her, and it would be painful for me, too.