I am 36 years old. I have never had an orgasm, nor do I ever masturbate, I just never really had the desire.
I am very attracted to the partners I've had and really enjoyed being close to them and having sex. But I have never orgasmed. I enjoy penetration, not so much having oral because it has never done much for me. I don't know whether it matters, but I haven't had a relationship last longer than 6 months. I also have an anxious attachment when I'm in a relationship and have low self esteem in general, although I feel I look after myself as best I can.
As I said, when I was young going through puberty, I never masturbated, never had the desire. As an adult, I don't either. Although I've tried with fingers I feel nothing.
I wanted to try and become a better version of myself and felt that it would be great to achieve orgasm for my future partner (currently chronically single) and myself to experience what it is like. I have had a partner who wanted me to 'squirt' for him. And I have had a couple of partners ask how to know when I've finished. And that makes me feel awkward because I don't finish and I feel like I disappoint them.
I recently bought a sex toy for the first time. It is a clitoris stimulator. Applied lots of lube, sat comfortably on my sofa, used the toy. It made me squirm and felt ticklish/uncomfortable, it wasn't a pleasant feeling. I suppose part of me feels that at least there must be something there, because it was only in a specific spot where I felt anything. Perhaps that wasn't the toy for me?
Might be worth noting that I have been on antidepressants since the age of 18 so I don't know whether that has had any impact, but even before then, I didn't have any urge for sex or masturbation. But I do fancy men and enjoy flirting and getting close to them, so I am not sure if I am asexual or not, which has sometimes crossed my mind.
Basically I feel so sad about the whole thing and actually believe it might be part of the reason why so many of my relationships have failed because I've always felt like I'm rubbish in the bedroom because I can't please my partner by showing I enjoy them. Which makes me feel worse. I've tried drinking beforehand to loosen me up, nothing works.
I am not sure if I should try another toy, go to a therapist, or if anyone has been in the same position and can give me hope!