Found this thread by accident, but I know exactly what you're talking about.
A couple of years ago, while still at college, I was invited to a party at someone else's place. I went with a close friend of mine who introduced me to a friend of hers who was attending the party as well. The girl in question was very plain looking, quite cute, though: brown hair, surprisingly large breasts (at least that is what I could guess, she wore nothing revealing), that classic girl next door look.
Anyway, we hit it off immediately, talked and flirted a lot over the whole evening. Eventually, my friend left, and because I was living in another city at that time, I invited myself over to that girl's place to which she happily agreed.
We arrived at her place shortly after. She had a roommate who was already asleep, so we went straight to her room, and immediately started making out. She eventually took off her shirt, not her bra, though. We continued making out some more, and eventually my fingers started making their way into her panties. But every time I tried that, she retracted.
Finally, I told her that I'm totally fine with us not having sex that night, to which she replied – to my surprise – that she's definitely up for it, but only if I'd turn off the light on her nightstand first. So, I turned off the light, we made out some more and I finally managed to pull off her panties.
At that point I immediately realized what the issue seemed to be: this girl had some unexpectedly large inner lips/labia minora – which she tried to hide under an unexpectedly large bush. I noticed that she seemed uncomfortable with that, so – to calm her nervousness – I immediately starting going down on her, sucking on her lips, complimenting how beautiful her pussy felt and looked, etc – which she seemed taken by surprise by. She orgasmed verrry quickly, and let me fuck her afterwards.
The next morning, as soon as we were both awake, I immediately started rubbing her pussy lips again and it became very clear that I was the first guy she's been with who wasn't bothered by her large lips. It was really cute how relieved she felt by this.
We've only dated for a few months, but it felt kind of nice that she seemingly gained a lot of confidence because of me. First, I got her to shave her bush and go completely bare, later I even convinced her to go to a party without panties and flash me a couple of times.
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