Hello all,
Some of you who read this might already know, but for those who don't; I have a history of conflict with my own sexuality. I'm 22 years old, a virgin, and have never had a serious relationship. All of this is by choice, seeing as I have always felt repulsed by my sexual impulses.
Recently, and after many years of struggling on my own, I have been regularly seeing a sex therapist, and these sessions have enabled me to learn and understand a lot more about myself. I've made progress in a lot of areas. I don't beat myself up for indulging in erotic material, I (usually) won't get mad and punish myself after masturbation, etc.

So, a few months ago, I met up with an old acquaintance from high school, and what was shocking was that someway, somehow, we ended up talking about sexual issues. This was surprising to me because this is something I talk to nobody about outside of my Therapists office. My friend was genuinely curious about my sexual challenges, history, etc. And I was in turn comfortable talking with her about these things because she had an extensive history of sexual activity. I didn't think of her negatively for this in the slightest. It was very much a yin-yang kind of effect. I was comfy talking with her about this stuff because I found her history for sexual openness to be the opposite of my own. In turn, she found my resistance to sexuality just as fascinating. We talked about the subject extensively when we occasionally hung out.
And then, before I knew it, we were discussing the possibility of doing some experimenting together. Namely so I could see what it's like. It was bizarre for me, this was something I never would have considered only a few months before. But now here was this opportunity to try some things I'd never experienced before, with a friend I trusted who knew all about this sort of thing and had in fact experimented with people in this way quite a few times before. I was hesitant and scared and nervous as hell and all other sorts of things, but we talked extensively about what we were both comfortable with and what our boundaries were. I wanted to go very slowly, and my only huge 'no-no' was that full-on intercourse be off the table, as it was very important to me that I still be able to think of myself as a virgin.
And, well, then we did it. We meet up and did... stuff. I was, naturally, a mess of nerves. And not just from your usually 'fist encounter' stress. Understand that these sorts of things were things I had sworn to myself earlier in life never to do, and here I was anyway.

After we first met up, I was a wreck for a while. Filled with mixed emotions of regret, worry, anxiety, etc. I didn't quite feel like myself. My aversion to sexuality had in many ways defined me for most of my life, and now more than ever, I felt like that was in flux. Which was quite scary. What was even more frightening was the fact that I had actually enjoyed myself, quite a lot. And a part of me hated myself for that.
So, I scheduled a spur-of-the moment appointment with my T to get all of this off my chest and see what she thought. She was very helpful. She said that she felt that this was a safe, consensual, and helpful way for me to try things out. After all, we did stay within out boundaries, we followed our own rules, and the world hadn't ended!
I digested this for a while and eventually met back up with my friend and we experimented some more. I was a bit more comfortable this go-round. I was much less a shivering puddle of raw anxiety. We both made light of it all, which was great. If this was something I could laugh about, then I could feel much batter about it and about myself. Of course I did have some intense conflicting feelings afterwards, but not quite to the same degree as before.
We continued to hang out and eventually, a couple of weeks ago, we got around to experimenting a third time. This was the time that has me in the most distress and has me coming here to write this. I had told my friend how I felt about all this, shared my gratitude, fears, and concerns. I had also warned her that throughout my life, I have always had an issue with orgasm. I can feel fine about having fantasies, masturbating, etc. But the second I climax, I experience a radical shift in my thinking and my mood. Depending on just how explicit my thoughts or fantasies are, my mood can range from mild depression to flat-out intense self hatred. So that had been one of our 'things', we didn't really know how I would react, and as such, we hadn't brought ourselves to climax in any of our experimentation yet. That changed this time. I'll spare everyone the graphic details. but I did orgasm. And I had one of the worst fall-outs I've ever had I freaked out, there's no other way to put it. It was an immediate shift in self, like I was suddenly waking up from sleepwalking. I was incredibly distressed, ashamed, embarrassed, and angry at myself. "Oh my god," I thought. "What have I done? I can't have done this. This isn't me."
After a few minutes, I calmed down and felt compelled to tell my friend that I didn't want to do this anymore. I told her that I had nothing but gratitude for her willingness to help me in this way, but the feelings I have at orgasm go beyond whims. In that moment, what I feel is certainty. And at that moment, I felt, well, I guess the best way I know to describe it is "honor-bound" to stop this. I just felt so ashamed of myself. This was naturally a bit upsetting to my friend, which in turn only made me feel worse. She felt as though she had ruined sex for me, which I assured her was not the case.
That was the last time I saw her until a few days ago. We got along great, which was good. We talked about it a little, making sure that everyone was ok with what had happened.

Here's the thing though, a part of me wants to try experimenting with her again .
I was ok with what we were doing until that single moment, and in that moment, I felt the need to shut this down. This is a feeling I have dealt with my whole life. I will look at erotic material, orgasm, and tell myself I will never ever look at that sort of thing ever again. I'll purchase a sex toy for personal use, use it, orgasm, feel terrible and get rid of the toy, vowing never to get one again. This is the sort of irrational thought-process that Therapy has helped me with, but in this instance, with another person, it made things feel much more real, and my feelings were consequently much more intense.
So at times I think to myself that I truly enjoyed what we were doing, and would like to try again, taking care around the orgasm side of things. Then, latter, I feel like absolute scum for even considering it, usually directly following orgasm

So that's my situation. I apologize for writing such a huge wall of text, but I honestly don't have many other places to turn to to talk frankly about this. Am I a bad person for even considering this? Should I have never done this to begin with? I just don't know what to think or feel right now. I appreciate all and any thoughts, comments, warnings, or advice I can get.
Thank you.