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I’ve recently become more sexually active and have found myself in a difficult position. I’m currently in a “friends with benefits” type of relationship and have found my partner to be quite shy and reserved about things. I really don’t know them that well in this case.

Problem

Before I get into the actual problem, I’d like to address my concerns about this individual:

  1. They don’t have the highest level of confidence and self-esteem. It’s evident they’re worried they might displease me.
  2. I don’t know them on any deep level; it’s mainly been rather superficial. I don’t particularly understand the reasoning behind their shyness.

The main issue was when we were in a specific position that yielded discomfort (slight pain) for me during sex. I said “ouch” and suggested we do something else. After that, it all went downhill. They were preoccupied and especially worried the rest of the time.

Goals and Summary

For next time I really don’t want the person to freak out and make a big deal out of it. I want them to understand it wasn’t necessarily their fault and that sometimes certain things yield discomfort/pain. We learn and move on.

I also don’t exactly want to have a heartfelt involved conversation explaining everything amidst sex.

How can I tell someone X act doesn’t feel comfortable without ruining the remainder of our time together?

  • Has this issue come up with this partner multiple times, or was this a one-off occurrence (so far)? – Upper_Case Feb 26 '19 at 18:26
  • @Upper_Case It was the second time we had sex, and the first time the issue became apparent (so far). – Anilla Feb 26 '19 at 18:28
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Poor confidence and low self-esteem in your partner are going to significantly complicate matters, and the guiding idea of my answer here is that you are going to have to account for those traits. A person with more confidence and better self-esteem would be able to weather small hiccups (like an awkward position, or an experiment that doesn't quite work).This is not the case here, and a solution like having a safeword may not be enough because it still requires your partner to cope with missteps, but doesn't really aid them in doing so.

Consider: from your description, there wasn't any confusion as to whether or not you enjoyed that particular thing-- you both knew that it wasn't working. The problem (according to my reading of the situation; you know this person better than I do) is that your partner doesn't handle missteps well. The problem seems more like they thought

Anilla didn't like it, I'm bad at sex. I don't know how to do it, and I am incapable of doing a good job, as evidenced by Anilla not liking that thing that I tried.

than the idea suggested by the question, which seems to me to be more like

I can't tell if Anilla likes the things I try or not. I would really like better communication so that I can confidently be moving towards doing more of what Anilla likes, and less of what Anilla dislikes.

I'm not saying that that second idea isn't present as well, but the proximate issue seems like the former one. More communication is generally good anyways, but a streamlined channel through which you can more easily deliver information which devastates your partner would probably not yield the results you're hoping for.

Fighting through someone else's poor self-evaluation is hard, especially if communication isn't strong between you. The problems which underlie your partner's issues may be beyond your ability to address either in your relationship more broadly or in-the-moment. That said, some things that might help include:

1. Be responsive and positive during sexual activities overall

Your partner won't know what's going on in your mind unless you express it, and your partner will probably like hearing positive things about their performance. Vocalizations and behaviors which demonstrate that you are enjoying things (the things you actually do enjoy, at any rate) might help reassure your partner. This can be true both of the overall experience and of specific things they do, and someone with low self-esteem may need both.

Even bland, generic communication can be enough for this. "I like that", "that feels really good", "keep going", and similar can do a lot to make it clear to your partner that they are doing (at least some) things well, which can avoid a spiral into despairing distraction. I'm not saying you should lie about liking something you don't, or overstating the experience you're having. But make sure that your partner knows when they do something you like. If the only feedback they (feel they) get is when something goes "wrong", it's easy for that to become their entire conception of your experience.

You already get direct knowledge on how much you are liking things. Make sure that your partner also knows when it's good for you! It's easy to assume that signals which are clear to you are clear to your partner too, but they won't have the same inside information as you.

2. Be ready to take the lead if something doesn't go smoothly

If your partner is driving the overall encounter, but then their confidence and attention are disrupted, then things can go off the rails pretty quickly. A more confident partner may be able to rally and try again, but a less confident partner may be less able to do so. Being prepared to take the lead elides this.

So if something doesn't work as hoped, you being ready to re-direct to a different activity can get over the derailment. It can help a lot if you initiate something that you both know you like, or that you can clearly indicate to them that you like. It's valuable to be positive here as well: not "let's do this instead", but "I love it when we do this, so let's do it!".

Phrasing that keeps "blame" (and a person with low self-esteem can read blame into a lot of presentations) off of your partner can be helpful. If you say "I thought that would work! I was way off" can be better than the passive-voice "well, that didn't work!", and is definitely better than "you didn't quite pull that off".

Your goal is to keep things going, such that your partner will not fixate on the "failure". An obvious, enthusiastic continuation of activities will help support that. Your partner is making course corrections after drifting a bit, not crashing into icebergs. They seem to have trouble understanding that, so demonstrations from you will help.

3. Sex has a visceral, in-the-moment quality. Don't rely on abstractions to counteract that

It sounds like your partner is pretty focused on what's happening in the midst of your encounters, and is having a less-than-ideal response to it. Telling them something abstract and logical may not do much to counteract that-- the emotional response will come first and can be hard to deny. Saying

I'm pursuing pleasure, so when I say that I don't like something I'm just trying to nudge you in the right direction, not put you down.

may not help with this problem at all. In the moment, your partner is expecting (or hoping for) a positive reaction, whatever that means to them. When that doesn't materialize, and they are confronted with the opposite (undesired pain or discomfort), there isn't much escaping from the conclusion that they failed. Whether or not you're trying to put them down is irrelevant-- if they'd done "a good job" you would have liked whatever it is that they did, and because you did not they obviously (in their own mind) chose the wrong thing, or executed the right thing poorly. It's a lot to ask of many people to disregard that in favor of a meta-understanding of the overarching situation and their place in it.

4. Establish casual, on-going communication about sex outside of sexual interactions

If your partner isn't sure what to do, or how to do it, it might take a lot of willpower to actually try doing something. If it goes poorly, that can be a big blow to the ego. More conversation about things you'd both like to try, how you might go about it (if applicable), and so on can lower that hurdle.

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  • I really like your second point. Though, I’m not always keen on “taking the lead”. Is there any way I might be able to show them the same effect (my desire to continue the experience, not blaming them) without being as ambitious? – Anilla Feb 26 '19 at 19:24
  • @Anilla That gets into territory where I'd need more specific knowledge of you and your partner both. The long answer starts with "maybe", and the short answer starts with "no". The issue described in the question is that your partner became incapable (or less capable) of driving things under their own power, and so things stopped. The onus is then on you, because no one else is left (per what was written). "Taking the lead" can be as simple as re-directing your partner to another, specific activity (if that works for them), but you will still have to do the re-directing when your partner is – Upper_Case Feb 26 '19 at 19:59
  • (continued) becalmed. If your partner can't or won't reliably "take the lead", doesn't provide what you want when they are "leading", and you yourself are not interested in being so ambitious, it becomes more a question of "are you two compatible based on what you want and what you can offer". The insecurity is unlikely to just go away without lots of time and effort, and it is incompatible with a partner who is confident and assertive in the meantime. As their confidence builds, more options may become available, but you need some way to get to that point in the first place. – Upper_Case Feb 26 '19 at 20:04
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Changed to Answer rather than comment.

The fact that you are starting is also something to communicate. That you are (probably both) trying and experiencing things for the first time so it's perfectly normal and ok for you to discover that something make you uncomfortable. Or that something "hit the spot".
It desired for both of you to communicate during the sex so both of you can enjoy it to the fullest. After the act you can discuss it further. For example if the "thing" was painful or just discomfort. How your partner felt, did they liked to the point they would like to do it again or they can live without it.

I think that especially in FoB situation communication about pleasure is the key. I know that people think that "bad sex is like bad pizza. In the end you still had pizza". But I wouldn't want to have pizza that make me sick. Talk with each other on how to make sex most beneficiary to both of you.

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