Hi Devilsdoughnut
Yes I can relate to your situation very well. I masturbated a lot since I was a child. Probably bec of CSA issues. I was taught it was very filthy, dirty habit so every time I did, it brought pleasure & then great sorrow. I would always masturbate in the prone position, but looking back I'd only get a clitoris orgasm.
When I got into oral sex I experienced a totally different orgasm relating to my g spot, like a full body orgasm. I didn't really start to have these till I was very comfortable w/my partner & he explored more of what felt good & I was comfortable w/it. I think your mind & psychological state has a great deal to do w/ producing an orgasm. If its not there, then its much harder. Yes that feeling of being uninhibited I think has to be there. Just exploring can be very useful. I used to think during it, "gee when is it going to happen? is he getting frustrated? Will he stop soon? Will I not orgasm tonite?" That's just too much pressure. Now my thinking is, " I love this & this person wants to please me & wants to do this to me. I deserve it & I'm gong to enjoy every moment of it. I don't wanto orgasm until the last possible moment."
A really good vibrator can be helpful. One w/multiple settings & speeds so you can control the intensity. I think if you give yourself some time to explore w/it & tell yourself you don't have to orgasm, your free to feel what's there w/no pressure. Once comfortable you can share it w/your partner so they could possibly use it on you for an orgasm or in combination w/oral sex.
Most of all your sexual experiences are growing as you get older. My orgasms from 20 yrs ago are nothing to what they are now so things do get better w/age & your body keeps changing as your hormones change. Don't pressure yourself so much to produce an orgasm every time. Having that in the back of your head can be a major downer when you should be focusing on what makes you feel good & going w/it.
I wish you the best of luck. Relax & enjoy!