Hey guys, this is going to be a handful, so I'll try to be as brief as possible, and break it down into dotpoints with some context.
1)Building up the courage of having sex in general. Admittedly, I'm one of those girls whos a huge flirt, all bark no bite when the moment comes. Whenever it's a new guy, it's difficult for me to be 100% comfortable (even if i've known them for months), and build up the courage/trust within them for/during the activity. Some nights it ends up being talking for hours until the guy is over the talking (so am I) and then he initiates – phew. What's the best way of building up the courage for a girl to initiate more, besides "with experience comes confidence"?
Also I obviously want it as much as the guy does, but by the time we're both in the bedroom, suddenly my shyness and fear completely overrides my arousal. I think every time it's with a new guy, I would only slowly get comfortable by the third interaction, but I want to build it up that (ideally) first session I am aroused and not all dried up due to shyness and fear.
2) Similar to 1), is my lack of experience. I'm always wanting to learn and get better, but I think after a handful of tries, I kinda feel like I give up and cut off fwb (nicely) and need to have space to think. Don't get me wrong, I've fortunately made guys finish for the most part, so I feel like I'm somewhat on the right track (but I've yet to finish with a guy). But I have so minimal experience being on top and riding. I know the guy doesn't always want to do all the work, and I don't expect it either. But learning how to ride kind of confuses me because I feel incredibly awkward trying to bounce or grind. I just need to know how to position my hips, knees, and feet better.
I also tend to gag really easily for the most part too, which ends up with me tearing up when giving head (but I still commit!). I've tried the whole brush your tongue with your toothbrush, curling your fingers over your thumb, practice with putting some pressure in the back of your tongue, but I still tend to gag quite easily. I'm not sure if there is some other technique that I've missed, or it just comes with giving oral more often.
3) I realised that I don't really feel a lot of pleasure through penetration. I kind of grew up with flicking the bean and never strayed from it, I didn't really do penetration, with a man or dildo until way later in life. Like I do like it when I'm doing it solo, but I think it only adds about 20% more pleasure to the experience. And I can't really climax through just penetration I realised. I've tried, but I end up feeling unfulfilled and needing to finish by both pentration and rubbing the clit. This doesn't sound too bad I think, but sometimes I feel when a guy is thrusting inside me I end up feeling some discomfort rather than pleasure. When I do it myself, it just feels right. I have noticed I do prefer it when the thrusting isn't as hard, and it's in shorter strokes, but how exactly do you word it like that to a guy, that he can understand it with full clarity?