How do you help a shy conservative partner genuinely want to explore rather than just go along with things?

Advice
1

Hey, lurker here finally posting because I genuinely need perspectives from people who’ve been through this.

My wife and I have been together over 4 years and just got married recently. She grew up pretty conservative with a controlling mum who knocked her confidence a lot. Now that we’re finally living together without that in the picture, I can see her slowly coming out of her shell in ways she never could before.

When we got together she genuinely thought butt stuff was weird and was pretty vocal about it. I never pushed, just took it slow over the years. Butt slaps first, then she got comfortable with me massaging and worshipping her butt, then rimming which she’s now obsessed with, then playing around the outside of her butthole, and eventually we introduced a plug which she’s now totally comfortable with and enjoys regularly.

The thing about her is she will never initiate or tell me what she wants. She hints and I lead. If I ask her what she wants to try she genuinely says she doesn’t know, and I believe her, she has no frame of reference for what she might enjoy until she’s actually tried it. Everything we’ve done together followed the same pattern without fail. Apprehensive first, then tolerates it, then enjoys it, then loves it. The plug is the perfect example of this.

From day one I’ve made it clear that this goes both ways and that exploration is about both of us, not just what I want from her. I think that framing is a big part of why she trusts me with this stuff when she’d never entertain it otherwise.

As part of where we’ve been heading, I’ve been slowly working toward anal. She’s given me her version of a green light. When I brought it up she giggled and said soon baby which for her is basically a yes. I’ve tried twice when the moment felt right but pulled back both times. Once because I lost my bearings in the moment, and the second time because she had a little jerk reaction when I tried to enter and I second guessed myself even though I knew that was going to happen.

Something I’ve noticed during our sessions is that she gets these rhythmic spasms around her butthole, either during rimming and the massage beforehand or during sex when I do reinsertion motions with the plug. Never both in the same session though. It looks and feels like a pleasure response to me but she doesn’t really have the awareness to identify it herself or know what it means.

I guess my main question is how do you actually help someone like her build real confidence and curiosity around this stuff rather than just going along with things. She’s come a long way but there are still these invisible ceilings from her upbringing that she doesn’t even realise are there.

Specifically wondering:

How did you help a conservative partner move from tolerating new things to actually being curious and wanting to explore?

For anyone who was the apprehensive partner, what actually changed your mindset? Was it something your partner did or said or just time?

How do you get to a place where she starts expressing what she wants rather than always waiting for me to lead?

Any advice on helping her recognise her own pleasure responses and feel confident enough to own them?

Thanks in advance, happy to give more context if needed.

2

You asked 4 questions. I wish I had useful and positive answers for you, for all of them (and question #2 does not apply to me), but instead I will be watching for others to give their opinions and suggestions.

However, I do have some ideas. Sorry for all the words, but IMHO, communication – words – are at the core of everything that will or will not happen.

My experience is with my wife who has tried at times to “become interested” in anal, but it just has not worked out (so far). We are much older, and have been married many times longer, than you and your wife. Sometimes if the interest is not present, it just is not present.

Given that, it seems like the two of you are making what I would call good progress. It is better than no progress at all.

Be patient, be helpful, be kind, be present, be loving, etc. Make possibilities available in a non-pressurized way and let her choose to continue doing what is happening. If she wants to stop, then stop.

From what you describe, I don’t hear the INTERACTIVE communication that I would expect to be happening. For example, ASK “may I touch like this” (and do a tiny amount of that touching). Ask yes/no questions, NOT “how would you like me to do it…” questions, since she apparently currently does not providing GUIDING answers to those. Ask yes/no questions: “May I do…” [yes, no]. Then, if yes, do a LITTLE bit and then ask “May I do more of…” [yes / no], etc.

If you get to the point of beginning to get to the process of penis insertion, that is probably not going to be a “moment”, but instead is a PROCESS. That process might take 20 times (20 different days) – or maybe much more??? or less??? – of progressive, tiny increases in the amount of contact, amount of pushing, etc., etc. ALL BEFORE EVEN what you or I might consider actual insertion. All the while, asking yes/no questions over and over and over again at each small step in the process. “May I do…” “Should I go a little farther…” “Should I stop…” “Should I continue…”

As long as she feels that she REALLY DOES have CONTROL over how far and how fast things progress – even if (according to you) she may not know what she wants or what she will or will not enjoy – she is more likely to be willing to find out what feels good, how she likes things done, etc., etc.

Regarding the “little jerk” that occurred, sure that can be normal for even a highly experienced anal-receiving person. At the same time, it can be an indication of things are going to fast. Given the point from where you are starting, my thinking is that the goal is to progress so slowly (over days, weeks, months) that each little advance will feel natural for her. However, there may always be the point where a “little jerk” occurs. If/when that happens, stop and COMMUNICATE!!! “Are you okay?” “Was I going too quickly?” “May I try again?” (It may take a couple/few minutes for the anal muscles to relax before you can try again.)

These are all yes/no question simply because you have said that she does not / does not know how to express herself (or has difficulty doing so). However, if at any point she says more than yes/no, GENTLY try to guide things into actual conversation. Keep it simple, keep it slow, keep it non-pressurized.

If she ever gets to the point of wanting to do anal sex, that would be wonderful.

But it also HAS TO be okay with you if she never gets to that point.

I assume you did NOT decide to get married so you would have an anal fuck toy. I assume you love her first and that you hope that she will find the enjoyment of anal sex that you hope for. But that you will continue to love her no matter what. Be sure that you are always communicating that and actually doing that. YOUR actions really do speak louder than words.

3

thank you for the response. I should do the interactive questions more often, i think thats a good idea as a start. we don’t really communicate during sex, partly because it takes us out of the moment, although i do listen to her and slow down when she asks.

and you’re right, i love her first and i want to see her grow as a person as well as sexually. thank you for the tips, i’ll start incorporating that into our love making and day to day life.

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4

To me, what you’re asking here is almost impossible to aswer.

My first wife told me, when she was still my girlfriend, that an ex kinda forced himself dry into her asshole. Hurting her. She told me she had sworren then that she would never allow anyone to do that again. I replied to that with “too bad, cause I’ve been fantasizing about anal since I was 15”…

After a few minutes she said “well, maybe then I should reconsider” and she did. And we did anal. About 30 times over 20 years. Only once was enjoyable for her. All the other attemps were purely for me, but she would tell me to hurry. To shoot my load and pull out.

This wasn’t how I imagined anal sex so I stopped asking for it. She was clearly not into it. Sometimes it doesn’t work. It’s nobody’s fault. She was really trying, sometimes asking for it, wanted to make it work. Her body wasn’t cooperative.

I’ve experienced the difference when my current wife and I did our first assfuck. I slid in so easily, she didn’t blink an eye, she just started enjoying my cock up her ass right away. I don’t remember if she moaned the first time I’ve assfucked her. But what I’ll never forget is her saying “why didn’t we do this sooner ?” And when I asked her how many times a week she would want to have her ass fucked, her reaction blew my mind: “let’s try again tomorrow” ! And the next 2 years I assfucked her at least once a day.

She was a whole different woman with an eagerness to be assfucked. She moans, she pants if I jackhammer her asshole. I can use her asshole any way I like and she always enjoys being used.

So why did it not work with the ex ? Who knows, it just didn’t.

So coming from a man who tried to teach a woman to love anal sex for 20 years, I can only say it’s not in your hands. It’s in hers. So comfort her, foremost. A woman who feels 100% secure with you has an easier time to let things happen out of pure lust. Tell her anal sex means a lot to you without making her feel her value will drop if she’s never able to give you anal sex. Pressure makes her spincter clench and that feels uncomfy for her when entering.

If the heart says yes, the ass says yes.

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5

Thank you for the advice, we had a talk and a lot of her reprehension comes from religion.
She was keen to explore more though, although full on anal sex is out of the question.

We had PIV sex with a butt plug and she let me finish in her butt. Afterwards she told me she felt cum going up her butt. I didn’t really prod to much about it cause I didn’t want to make her feel like I was obsessed with the idea rather than her, which I think it’s what you’re saying “without making her feel her value will drop if she’s never able to give you anal sex”.

A few days later, we had some pillow talk and I asked her again about it and if she didn’t like it.
She responded with, I didn’t say it felt bad. I asked a couple more questions, and she told me when it happened, she felt me going in a little and it didn’t hurt. She also said it felt good, but a weird kind of good. I asked if she wanted to me to do it again/more frequently, and she said yes cause it felt hot too.

We definitely managed to progress further, and I’m happy with what we have. Maybe in the future we could get to a point of anal only. One thing to note is that she has a phobia of child birth (we stack multiple birth control options to alleviate the fear), which I think would make her lean towards anal only eventually, especially since she now knows this is an option for her to feel pleasure as well.

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