So I have a LOT of difficulty having an orgasm. Even on my own now apparently, but I've always had a lot of difficulty with a partner. It's actually gotten worse since I got a vibrator since orgasms via a vibrator HURT. I mean, it feels better up to that point, but I get too anxious when I approach climax to actually have an orgasm. I've been switching back to my hand the last couple times of tried and used the vibrator for penetration and I can at least stand it that way. It's still not very satisfying since I pretty have to go back to the one position I can comfortably orgasm in and it's like all the training I've been doing on my body to orgasm in different positions has been for naught.

And even worse than this is what my inability to orgasm seems to have done to my partner. He's never been confident sexually and had issues with ED and premature ejaculation since he first started having sex. To add to that, his partners discouraged him from exploring his sexuality at all and at least one of them left him because he wasn't "good enough" in bed. He's 32 now and I'm the longest term partner he's ever had by a long shot and we've only been together for 6 months. I'm the first he's ever really experimented with and he's more comfortable talking about things he likes with me than ever before. But, he still freezes up if I ask him "what would you like to try?" He just responds that he doesn't know. If I ask him if we can try a position outside of the two we always do, his response is "let's just stick with what we know". Every time we try a new position, he can't figure out how to penetrate me and loses his erection.

The last time we had sex, he kept being unable to penetrate me (he wasn't hard enough) and eventually came trying to get himself hard again for like the third or fourth time. Naturally, he's devastated, but I'm unsure how to help. Especially since my own issues are likely getting in the way.

Just so you guys know, he's healthy and is able to get hard and last a long time when he masturbates. He also claims that he's apparently only turned on by the anticipation of intercourse and not by the act itself and that's why he loses his erection. It also doesn't help that he insists on buying condoms that are difficult for me to put on and insists that I always be the one that puts it on him. I don't mind putting it on, but I'd rather have condoms that I can easily put on correctly and not struggle with, leading him to go soft.

And he is stressed, but he's always going to be stressed. It's the career field we're in. Not to mention, a lot of his stress now is his own fault and the fault of his advisor for having take 15 hours of graduate level classes this semester.

So, my questions are:

1. How do I convince him that my lack of an orgasm isn't his fault (he's been blamed before or at least felt like he was being blamed) and that I'm not going to leave him over this (again, it's happened before)? I've expressed this to him before, but words are not going to be enough.

2. How do I help him explore his sexuality and help him get to the point where when I ask him what he wants to try that he can say "I want to try X" instead of "I don't know"?

3. How do I explore how to get an orgasm without the added pressure of knowing that me not getting an orgasm from him (the only times I've had an orgasm with him present, I've been masturbating even though I tell him that he helped me reach it) makes him feel worse about himself?

I really want to go to a sex therapist, but we can't during the school year because of lack of time and we might not during the summer because he's trying really hard to get a job that will take him out of the state, if not overseas. I've tried to get him to at least apply to local jobs but his excuses were he didn't want to compete with me (we work in the same field) and that he doesn't have time to even think about filling out applications. So, we'll probably have to solve all of this without a sex therapist or with just me going to a sex therapist on my own, which won't help his anxieties over sex and subsequent ED and premature ejaculation.