This happened a few days ago. I met with a friend with whom I had done some playful stuff in the past - you know, some kisses, some touches, some... "I'd fuck you, but I don't know if you want to fuck me". She's super shy (and submissive) and I'm fairly shy (I can switch, but I'm submissive 80% of the time). We first met at the gym, where I offer some "support" for new women who want to try the gym, but are slightly afraid or discouraged. Imagine something like a support group, more than a personal trainer.
Our relationship quickly evolved into something more "touchy" and I clearly felt some degree of attraction from her. I'm not over-confident at all, so I promise the signals were there.
If you need a brief physical description, I'm around 5'3'' and 121 lb, athletic, small boobs, big, round ass. She's much smaller than me - maybe 5' and around 100 lb. She has this angelical face, super, super tiny and round boobs (and ass). She is this kind of woman who has never actually done much exercise, and just has a naturally fit and beautiful body, and I believe I didn't have much luck in the genetics roulette, but I do train quite hard.
You could say we're not the perfect match, but we clicked quite quickly and became friends - but let me get to the point.
We both confessed we were into casual nudity, so... Last 2-3 times we've met, we've been naked doing all kind of things - cooking, dancing, watching TV, painting our nails, yoga, exercise... It's hot, and after she leaves I furiously masturbate, but I had NO idea if she liked it, if she wanted more, if... I mean, she didn't look disappointed that nothing else had happened, but... Maybe I just can't read this woman.
Anyway, for some reason I just struggle to go beyond that, you know? I believed I had made more than obvious... Suggestions. But she's the type of girl that always answers with "well, if you want!" or "hahaha, I guess that would be fun" to any of my advances. Or maybe I'm not too bright when I'm horny, go figure.