Experimenting with a friend, could use some advice

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.

First of all, I would like to say that you have enough of a realization of what's going on than you give yourself credit for.

You aware that the whole pleasure/guilt thing is very much ingrained in you. And you now have the knowledge that, for you, orgasm BY ANY MEANS is resulting in the same reaction for you (albeit to varying degrees).

Are you a bad person for considering this? Absolutely not.

Should you have never done this? Only you and your therapist know what the "right" step is for you. I think you did something that you knew might have terrifying consequences for you....but you did it anyway. And you did it in the most careful, responsible way possible. So, in my honest opinion, you thought it was the right time.

Whether or not you do it again will be your own decision and it will be the right decision for you. Because you have things well under control.

You have experience 3 times with this girl so that must be a huge step for you ...
Maybe what your friend should do is have you massage her from head to toe so you have the control of that you touch and what you don't want to touch have you done a full body massage on her ?

If not try that then when you feel ready take one piece of clothes off her one at a time and over time have her be nude and give her a full body massage.
Then when your ready have her do that with you a full body massage .
Once you feel good about that then try something else ..
I think your obsess with being a virgin like you think your not clean if you go all the way with a girl .

If you don't feel the need to have sex then don't , not everyone wants or needs sex to be in a relationship . Just be honest with people you date and say I'm not into sex .
Maybe you need to fall in love to have that special connection and be married , so you feel clean ?
Could that be it ?
Don't feel like you have to have sex because no one is pushing you your putting that all on you .
Do other things in life that make u happy why let sex be in your way of happiness ?

I appreciate the advice.
I DO obsess over remaining a virgin, it is extremely important to be. To me, sex is something vile, and should I lose my virginity, well, that would about be one of the vilest things I could ever do. This is why the notion of having sexual relations with someone I may come to have feelings for would not make things better, but worse.

Thank you for the reply. I'd certainly like to think I have things under control, but it certainly doesn't feel that way. I shift from regret to shame to acceptance about it on a daily basis. The knowledge that I did things in the safest and most careful way possible is sometimes all that keeps me from beating myself up over it.

I did spend time with my friend the other day, and I brought up the fact that experimenting again had crossed my mind. I told her that I felt incredibly guilty about it, that I felt like a monster for even considering it. But I think it was best to get it out in the open.

Hi Appalachian, despite what you've said I kind of worry that you might get hurt in this if feelings come into play e.g. if for her it's a bit more about helping you and for you it turns into developing real feelings for her which aren't two-way.
But you're pretty smart , so just saying if you could really watch out for the potential of that happening??
And maybe "desensitization"/gradually safely overcoming the fear of/anxiety over........might help, keeping talking with your T about it might point to if it might help you as/if it goes along.
And if you carry on maybe go at your own pace, same "routine", but just taking it a step/two steps (??) further if you're comfortable, each time???
And maybe keep going on working on where/why your value system has come from??? And if it's actually portraying your individuality or something else???
I just get the feeling that you wouldn't be seeing someone else orgasming with someone, loosing their virginity as any sort of a possible issue for them, in any way???
And hey, if you're worrying about what you've done/what you're doing is "shameful", then hopefully the fact that we aren't judging you on that will help with the self-acceptance just a bit??
Just for me, try not to get hurt, hey??!!
Alison

I wonder if you got married and then lost your virginity, would you still feel dirty or would you feel it was ok ?

Do you like blintzes?
Please answer - the question would make sense then.



PS Congrats on having covered that much ground in a relatively short span of time. Also, from what you wrote, you have been impeccably chivalrous in that you made sure that she did not get upset.

Thank you. I don't have *too* many worries on that front, that's part of why I'm feeling so conflicted. We get along great, but there's not anything special here. I think she's a great person, but... no deeper connection.
That's a big part in why I felt so guilty after the last time. I felt like I had somehow taken advantage of her, even though she had made it quite clear that this was something she was OK with. All the same, it felt like something to be guilty about.

No, it would still be a terrible, terrible thing for me. Moreso, even. It is far out of the ordinary I know, but or me, sex is NOT an expression of affection. To me, it is one of the most un-loving things I could ever do.

Is it a riddle? I'm so godawfully bad at riddles I had to look up what that was, and can't say I've ever tried a Blintz!
It was quite a task to make sure she wasn't upset. After all, she is the opposite of me. whereas I see sex as something to be repressed and avoided, she sees it as something to be embraced and accepted. So, when I practically had a full-blown panic attack post-orgasm and said I felt like we shouldn't do this again, she was naturally pretty distraught. But you are right, I can take comfort in knowing that, now matter my feelings up to that point, I did do everything I possibly could to be 'chivalrous' and make sure she did not blame herself or feel bad.


Thank you everyone for your support! I really cannot overstate how much it helps to have somewhere to talk about this.
That said, I have given this an awful lot of thought, and I don't think this is something I want to do again. There are so many factors at work here, and often it's hard to think this way. When my hormones are acting up, it can be hard to think straight, it's difficult to think of anything other than how much I'd like to try doing that kind of thing again.
So I've asked myself the simple question. I'll wake up one morning and look back on my choices. I ask myself, which choice is going to make me smile, and which is going to make me swell with regret? When I think of things this way, the answer is crystal clear: I know that doing things like this again will make me full of regret, but choosing to abstain is going to make me proud of my choices and happy with my decisions.
That's all it's ever come down to really, what choice am I going to feel good about when I wake up in the morning?

Blintz are Russian crepes, and there is a saying that the first one is always a ball of half-cooked dough. There is an objective, physical reason for it - I do not remember exactly what it is since I cannot make crepes (the range in my rental unit is much older than I am and it is an electric range with the uneven burners, so crepe making is completely out), but more or less there is some process that goes on when the butter and dough for the first crepe are on the pan that paves the way for the success with subsequent crepes. The first one is a ball of half-cooked dough but the subsequent ones are thin, round, bubbly crepes everyone loves to eat. Without that first fiasco, the successful crepes cannot see the light of day.

I think that is a great idea that all of us can use in our life
"what choice am I going to feel good about when I wake up in the morning?" I am going to try that in my life ... thank you

Hi Appalachian, you're absolutely right, you need to be doing what feels right for you.
And you know at some point that may change..........but it does sound from what you said, like something you just needed to try.
And hey, while you're deciding you don't want to go there again (and that's absolutely fine!!!) just don't forget to give yourself the credit you're due as well!!!!
Come on it wasn't all bad was it??? And I personally, see some achievement in there!!!
So try to look back on it as you did break down some barriers, but just not right for you, right now???
And keep rolling with the what feels right for you, hey??!!
Alison

Hey all. Thought I'd come in and post an update as there has been a development.

So, my friend and I have spent some time together just hanging out, and it's been great. No awkwardness or anything. I did tell her that the thought of experimenting again had crossed my mind, but we talked no more about it.
Well, today we talked about it. Turns out it was on her mind as well. We sat down and had a long conversation regarding all of our thoughts on our previous "attempt" and our concerns about what could be issues hypothetically going forward.
It was... good to talk about. Even after everything, there was a lot of tension in the air and things left unsaid, so it was certainly not a bad move I think.
To sum it up, we've tentatively agreed to try experimenting again. We sat down and had a very long discussion about what we'd like to change, keep the same, and improve upon from last time. We went through a thorough list of what we were and weren't willing to try, and established an extensive series of concrete rules to adhere to.
I'd be lying if I said I wasn't still very conflicted, scared, and anxious. But a part of me wants to give this another shot, and I feel very confident in just how extensively we have laid out or concerns and ground rules.