Hurt So Bad
So you've got some chronic pain and body complications, and the new woman you're dating is incredibly understanding of this. To my understanding, there are unfortunately no real solutions to your pain, as is the case with many chronic pain illnesses, but you've found out how to manage this with pain meds, massage, and acupuncture. I'm sorry to hear about your condition. I have known some folks who have struggled with chronic pain, and it sounds horrible, though it seems like you've been dealing with this for a while and understand your condition a bit, which is good. It also seems that this woman you're dating is interested in you AND accepting of who you are and what you are dealing with, which is fantastic.
Everybody's got some body issues to deal with when we start revealing ourselves intimately to another person—you've just got a very particular set. It sounds like you're pretty submissive, based on your description of CBT (aka cock & ball torture, which is what I assume you mean, and not cognitive behavioral therapy which is what I first assumed), which is part of why this is a challenge. And it sounds like the pain isn't so much coming from what you're doing at the time, but by how your body reacts in the following days. Your body will do what your body needs to do—I'm not sure if there's a way to make the recovery any less painful. As you play with her more, perhaps you can observe the ways that the play and the painful recovery time are related, and do more of the things that are easier for you to heal from and less of the things that are hard to heal from.
You say you've only had sex one time so far, so I'd like to challenge you on your definition of sex here. I assume you mean you've only been hard enough to fuck her once, and that ED issues have gotten in the way. What about using your fingers, or your mouth? What about buying a dildo? I know that's not quite the same, but there are lots of other ways to fuck, and you can play with making your sex life even more about serving her, if that's the kind of thing you're into (and I get the impression you might be).
You also might want to think about what it means to be submissive with this woman. You mention things that are physically painful, but are there ways to submit that don't involve masochism? Could you get down on your hands and knees for her? Say embarrassing things? Let her order you around verbally? Do things for her that you wouldn't usually do that are challenging but hot? There are ways to submit and ways to play with power dynamics that don't involve pain.
It's also possible, though, that the pain is part of what you actually like about this dynamic—somewhere in your subconscious. Perhaps if you take the pain dynamic out of the play, it wouldn't be as interesting. Ask yourself if this is related to the chronic pain you deal with, and if perhaps there might be a way you can find some healing in your pain through your masochism. (You also might want to take a look at Radical Acceptance: Embracing Your Life With the Heart of a Buddha
I don't know a lot about ED, so I can't really speak to that. I'll let my other panelists give you some suggestions on how to stay hard. In my limited knowledge, part of ED is mental, so it is also possible that as this relationship builds and grows, you'll be more confident and more able to be vulnerable with her.
Sex gets better as you know somebody better. If this woman is as good for you and to you as your letter implies, don't let this issue get in the way of what you're building together. Be honest and open about the pain it causes you, keep her updated, and brainstorm ways to make this easier on yourself. Take good care of your body and listen to what it's telling you. But listen to what your sexual self needs too, and listen to what this fabulous woman needs. Somewhere in the middle there is a space of overlap.
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