I can't have pleasurable sex

I've returned to this site with more sexual confusion, so buckle up because I'm definitely a little strange when it comes to these things.

On my first post here I summarized that I am a young female who is almost exclusively attracted to other females. This isn't really a problem for me, but my gender identity hang ups make it so I feel like I should have a penis and generally be masculine. So sex without a penis is already an issue for me- as silly as it sounds. But that's just the background information.

I've recently decided to date a girl I enjoy being around. I don't do relationships, but I decided to try one out. I bring this up because that means I will be having more sexual experiences in the future, and it's brought up some weird quirks of mine that I'd like to get sorted out.

First of all, I cannot stand penetration. It isn't incredibly painful for me, and I've never bled or anything. It just feels like nothing, or if something, uncomfortable. I do not get any sexual pleasure from it, and sometimes it just kills my mood and I want to stop and go to sleep. My only explanations for this are:

1.) Previous negative experiences. The last girl I was with penetrated me with her fingers and it hurt like hell. She scratched me from the inside, and it really didn't even end there. She called me a "pussy" for not being able to take it and pretty much berated me from then on. I've only had one other incident where something of substantial girth went into me, and that was an electric toothbrush. (blah I know) Still with the same girl. I didn't want to chicken out, and it hurt a small bit, but was just generally not arousing. She tried to convince me I orgasmed when I had no such experience.

2.) I never learned to correctly. I didn't figure out until late middle school that stuff was supposed to go in there. I was too afraid to do it until highschool, and received no sex ed or advice other than smutty books and movies.

3.) My aforementioned gender issues. While it was an exciting thought to have penetrative sex, it never felt good beyond a fantasy. Sometimes it just feels absolutely wrong, like my body was not designed to do this, and that it shouldn't be happening. That nothing should go 'in' there, only 'out'.

Those are my main reasons for penetrative sex or masturbation discomfort, but I also cant get much over the other kind. I've tried external stuff but that doesn't work either. I just eventually get bored and tired after hours of trying and give up. Really the only thing the gives me any sort of pleasure is friction, with my clothes on. And not even that does much, because I really am not sure if I've ever climaxed from it before. It just ends up hurting my body so I have to stop eventually, or the mood passes.

I've recently started taking progesterone because of a significant imbalance, as well as other vitamins. Could it be I'm so depressed I can't feel sexual pleasure properly? Will the progesterone help? I'm honestly very confused and would like some kind of satisfaction or at least an answer in my life. Are there any conditions related to this?

Thanks for reading and feel free to ask questions and comment below, I'd really love every ones input.

Hi

After reading I was wondering if you’ve been cleared by a physician? It would help you check that box that everything is good to go physically IMO. That’s the route I took straight away when I started having issues. Mine is nerve related, but I can attest to sometimes being in the sex situation and feeling nothing when my partner is “hot and bothered”.
Please keep us updated
Josh

I am hetero, but, I have never, and I do mean never, got any pleasure from penetration sex. I have only orgasmed from fingers or tongue, I would put up with penetration to keep the guy interested, but i never craved it for pleasure. If you are not turned on, then you will not be lubricated, and any sort of penetration will be painful, and definitely not enjoyable. I used to masturbate a lot when I was by myself, and consequently my body got used to responding to that sort of stimulation, so I lubricated quickly, consequently penetration was not painful, like it used to be.