Dealing with a new partner's sexual experience

For those sensitive to sexuality, the following does contain some - I do believe modest - references to sexual activity as they are at the root of what currently drives me into madness.

I started a relationship a little over a month ago. I had been agonizing over somebody who was not interested and came to the conclusion that there was a person with whom I had been building up a beautiful connection for some time (most of it, i tried to discuss in this thread: I need you guys to point out where I can improve myself). I gave that new contact extra attention and indeed, we had two wonderful months and at some point, a little over a month ago, we kissed. Astonishingly, I haven’t felt anxious at all for months, I was even confident we would become a couple. Being near her gave me so much confidence on all levels.
I think we have a great connection. We kiss often, we cuddle a lot. I had a few sleepovers and though nothing much happened, they were great. We went to bed, cuddled and kissed, the lights went out and it was even harder to not touch each other. In fact, we don’t manage to sleep when we touch each other, we really have to move to the extreme sides of the bed. It is a new experience for the both of us. And still, the last week all this remains merely a silver lining.
Early on we tried to have coitus. It didn’t work but we got through it by talking. We agreed we would wait. All in all, I had a good feeling about the night. The proximity of somebody is what I missed most, so it was for her. I told her that for years I had believed I lost to ability to feel connected to somebody (I explain later why) and that I had never felt so close to somebody. Holding each other gives us both a kind of energy we have never experienced. And we could talk, we managed to find a way out. But this conversation also involved talk about the source of my insecurities (a previous relationship in which I was subjected to pain during sex). Ever since that, there have been a few things she said - out of concern for me probably - that bothered me. We did have a moment - twice - when she reached an orgasm when I was massaging her breasts, she had given me a hint and I picked it up. I have never seen her face so relaxed and content, she was surprised this could happen so early on in a relationship (I will call this our special moment). There is "Normally I take more initiative but with you now, I dont know," it gave me the impression of an extremely experienced woman. Another is "I don't want to put you off, I dont know what to do", while she was carressing my shorts after that special moment (and I wonder if it was an invitation to point her to what I desired at the time). This remark too gave me the feeling that she is extremely experienced.

I think I should elaborate a bit on the source of my insecurities. I started late with a one night stand at 23 and a first relationship that lasted 3 years when I was 25. She was two years younger and I was her first. We explored a lot of thins; we would try out every positions we could think of. We have both been tied to the bed, blindfolded, we experimented with hot wax and ice cubes. On a rational level, I do realize that I am not that inexperienced. That relationship ended shortly after we bought a house together. Sex was on a relative low because of work I had to do around the house, she started to cheat on me and her last comment was that sex with me was boring and always the same (which was probably true these last months, I had other things on my mind).
After that, I was sinle for eight years. Without even a kiss.
I was 36 when I met a woman who was 12 years younger than me. She had had around 80 one night stands and could not stop talking about it. She said she had done all kinds of dominance based experiments and started doing these things to me, unasked. It stopped when I stopped resisting her. It was in those days that the anguish I experienced the last week surfaced for the first time. It lead to a severe depression, I lost my job and I have been struggling to get back to my feet ever since. We did get over it and had five or six years when sex was great and some of these problematic things were repeated and felt safe in the altered context. We never shied away from trying whatever came to mind. Nevertheless, this relationship had a lot more problematic aspects: I lost contact with almost all of my friends, with my entire family and she really undermined my confidence on all levels. We were together for 10 years and the last three years, frequency of sex dropped. I had gone back to university and was struggling with my masterthesis; I remember the last time we had sex, a little over a half year before we broke up, and that she said: "I was ion gto wait until you graduated but it became too pathetic" the day after.
After that, I have been in a psychiatric hospital where I met somebody with whom I was toghether for a year. I never had really strong feelings for her and her past did not bother me at all.

My current girlfriend wanted to talk about my insecurity last week. Opening up about my concern that I percieved her as having so much experience and having done all that a person can imagine was stressful. I am on two tracks here: there is fear that I will never be able to satisfy her. I lack the skill and the experience. I remember saying that I would not match the frequency she would desire, she said she used to like doing it often but that she also had a relationship with somebody who was prestation-driven and it made him insecure and they hardly had sex and that she valued the love and respect in those occasions. For me only the doing-it-often part remained and added to my being intimidated.
The other track is the idea that none of the things I do will ever be special and meaningful to her as everything will be a been-there, done-that experience. She replied it is not about keeping a checklist. She referred to our special moment and that she had indeed experienced this before, but never this way, never with the intensity it had between us. And I do know what kissing after that meant to me, I remember the impact of her carressing my back at that moment and that even these things felt so special so me but I can't believe they can be for her, given all her experience.

Since that conversation, my thoughts have been running out of hand, "counting" ex partners (as I did before with my ex-wife, where my caldulations added up to a number well over a thousand) and agonizing about my skill and the meaninglessness of what I can bring into this relationship sexually.

Wednesday she asked if we could talk. It was the second time she stressed she had never had a one night stand, that she only had sex in relationships that lasted for years (she has been together with the father of her daughter for 19 years, starting when she was 24. It was not a loving relationship in which sex was down to once in a few months because she had to for years). She also said she did know the difference between making love and having sex, from even before her marriage.
She also had noticed that I was guessing and blowing up things. She thought that telling me that her relationships were always lasting years - I do not know when she started, nor a number but that issue seems to be solved for now -. She thought that opening up about her experimental attitude and that she had done exactly these pain-driven things that had bothered me before and that they were a theme in a boudoir photoshoot would help me. She had commented before that these things can be "fun like crazy" with the right person, in the right context and she had noticed what that remark had done to me. For half a day I was more peaceful but now it is worse than ever.
Somehow my anxiety pinned things together: I do now see confirmed that she has done everything one can possibly think of and that her not wanting to compare relationships and not having expectations is a result of that phase - she did name it as such - being so spectacularly great that everything (why else the phososhoot?) she will experience henceforth can only be a disappointment.
What's new, is that I feel left out. I will never be part of the most beautiful part of her life because that lies long behind her.

But for some reason she does not let me go. She keeps supporting me. She stresses this is not my fault. She will have a surgery on September 12th and I will go to her to take care of her. But the situation is weighing on her. She is spontaneous and she has lost that because she does not want to confront me too much. For her, at this moment part of the connection is lost. Not only does she not want me to sleep over for now, she even is reluctant to hug me. It think it is partly out of concern for my well-being and seeing the impact of the situation but at times a hug is what I need most.

I am not sure what to do. I am terrified this will be the end of what started as a beautiful dream (but I do know I did get over similar feelings previously, however hard it was). I want to be special and important to her, but I am scared that I will have to perform sexually to achieve that and I am simply not on that level. At the same time, I am afraid that I will never be confident enough to engage in any sexual actitivy with her and afraid that she will want to see my confidence restored before she wants to (part of what helped me before is that my ex-wife was able to not anticipate on possible emotional disturbance, which eventually gave us a number of experiences that did help me).
And also, if this does end over this, does it mean I will have to accept I can never have a relationship again because this will always bother me?

But for now, I am willing ot try and get over this. I am not sure how. My psychologist stresses the importance of building up our own story but the idea of disappointing her when I am clumsy or just plain boring terrifies me. She doesn't want to for now, nor can she for medical reasons. But I will also disappoint her when doing nothing. At moments I think that accepting this will have to be a sexless relationship would help me, but this will probably not last long.
And also, is it a good idea to talk about my thoughts and feelings with? I think they can be very confronting but on the other hand, I cant' deal with them alone; I have been crying on and off the entire day yesterday. I have been hurting myself.
My therapist is on vacation for two weeks ...

I never think, "oh yesterday or last year my morning cup of coffee was so much better than the one i am having now." I always think the one i am having now is the best.

Why do you live with ghosts?

Why are these people talking about past sexual experiences so much? What’s their end game?

The only thing I care about their experiences if it resulted in children and if they take care of their children. I also want to know if they currently have STD.

She reached an orgasm by you touching her breasts? It’s not possible. Are you sure you didn’t touch something else or she didn’t?

I don’t know why you decided she is so experienced. Based on what? Sure she was married but other than that who knows? Listen, people either click or they don’t. No one worries about disappointments. I’d focus on your connection and not actual sex

Your and hers past experiences need to stay in the past

Oh, it's possible!

Hhhmm I’d think it’s missing sex organ to get you to climax. Interesting

Theres a connecting nerve...

Breastfeeding? I think it’s old wife’s tale. I can’t imagine getting even remotely aroused while breastfeeding.

I don't know nuthin' 'bout birthin' babies!

Google it! Its a thing!

Maybe I should summarize.

Early on, we had an attempt at coitus. We didn't manage, we agreed it was too early. I did talk about my insecurity, stemming in part from my ex-wife who bragged about a lare number of one night stands, bdsm like experiments and subjected me to similar things unasked.

Then there were some casual remarks from her about usally taking more initiative but being unsure what to do with me, about not wanting to shock me as an explanation why she did not take any further initiative. And when the issue of pain that was inflicted during sex, she said this could be fun like crazy. These made me insecure and caused some minor distress that she noticed.

Last Saturday , she wanted to talk about this. And this conversation is a bit of a blur. What I recall is that I expressed my doubts about ever being able to satisfy her. She said at some point that she had times when she loved to do it often but that she also had a relationship with somebody who was very prestation driven and that sex did not occur often but that it was fine because it was an act of love. That is the day I started agonizing about her experience, as opposed to mine (for me, she only said the doing it often part).

Then on Wednesday, she wanted to talk again. That is when she said she liked to experiment, had this experience with pain, had a photoshoot and that it was a phase. Ever since, I am convinced that this episode was so great and overwhelming that all that comes after that can only be a disappointment (me included). That, in my thinking explains why she does not compare relationships, and why she has no expectations except for respect and love.

That is why I started delving in my own past, hoping to find some proof of experience (and I do believe there is). Maybe I should not have written it down so extensively but it was part of my process of trying to convince myself I am not a noob.

We had our moments, in which she stresses an extreme physical response to touch and kissing that she never had before (and the difficulty to let me loose when we go to sleep); about having experienced an orgasm by massaging her breatst before, but never the way it was with me.

But somehow, I cannot believe I will ever be more than good enough. I will so to say never be what she desires, because she had what she desired and it will not come back. In my head she has accepted that she has to settle for less.
I am loving and caring and I know that she experienced little love in her marriage and that even in previous relationships, sex was often without love but I can't believe this is enough.

The last week was difficult. My panic attack, causing me to become distant, and to lose all my empathy, and the obvious distress I was going to did have an impact. I am not sure whether I can discuss the emotions and thoughts I experience with her because she does feel guilty about having caused this.

To my own surprise, it is.

You don’t have to answer but why didn’t you have sex with her? Was it a physical issue?

I think we were just not ready. It was the first time I spent the night, we were together for three days.

From my part, it was stress. We had been cuddling and kissing for hours and I had an erection all the time. When the moment came, I could not maintain it completely. It is not the first time that the first time with somebody does not work for me, somehow I have to accept this.
From her part, she was not, how should I say it, accessible. She wanted to, it was she who asked.

A few days later, she had a blooding and she now knows she needs surgery. She is not allowed to have coitus ever since and until two weeks after the surgery. She has been really under the weather from her antibiotics lately.

All in all that night felt really great. I think we did deal with insecurity in a great manner. I really felt connected to her, a possibility I thought I had lost during my relationship with my ex-wife.

I just saw an ad passing by which had a statement saying that in sexy, it is the first times we remember. It terrifies me.

I am so hoping to find a special place in somebody's life and it feels I never will.

You put too much emphasis on sex. There’s more to a relationship than that.

Date people longer before you decide to be intimate. Build the foundation and deep connections first then everything else will fall into place. I am married and I don’t remember much about first time. Plus first time is kind of awkward.

Focus on other aspects of your relationship. What do two of you like to do?

So you mean to say that, regardless of how great and overwhelming and experience was, if we manage to build up a connection - which I think we already have - that which I think of as they greatest experience she will ever have will not matter?

Could it be that this period will be a nice memory for her, but I do have nice memories too from before I met her. Usually, I don't dwell on them(I tend to focus in the negative), I really had to dig hard to get an idea of what I had done sexually and I only do so because I am looking for proof that I do have something to offer. The only real and video memories I have, are of the smalle things that happend netwerk me and my new girlfriend.

We did decide we tot carried away. We did decide we would wait. It is just that I have this idea that she is extremely experienced and had an episode that was so overwhelming that I have a hard time believing she is not just settling for "not completely disastrous" (that would be me then).
Relationships do strand on sexual frustration ... the idea that I will not have enough to offer terrifies me, precisely because I feel such a dtrong bond with het.

We met dancing tango and are meeting tonight and tomorrow, probably on Thursday and as good as certain on Saturday, despite her having a 15 year old daughterand living 40km away from me (and I live very near to where all the dance things are going on)

I am not sure about orgasming, but breastfeeding per se right after birth sure helps shrink the uterus. It was painful to me, like uterine cramps, but surely very effective. Breastfeeding releases oxytocin which in turn causes uterine contractions.

I have a hard time with some of your sentences which might be translations from French. For instance, what does prestation mean? It is not a word in English. I looked it up in a French dictionary but the meaning does not fit the context of your writing.

Still, I can probably tell you that everything you are writing about is not important. One likes, or dislikes, a person and not the bag of tricks. She likes you. Accept it and forget about the rest. If you cannot, seek individual therapy.

I looked it up and learned a new word, yes it is translated from French but used correctly by OP.

It sounds like you feel insecure in your sexual abilities and concerned that because she is experienced she will judge you less than.

Here’s my opinion on sex FWIW: Sex is good with two people, if they enjoy being with each other and feel satisfied. It doesn’t matter how much experience anyone has had because there is only the current experience happening in the present. Does it feel good?