SWM 123 – AQ – Enjoying anal sex, periods and vacation, aging and orgasms, fantasizing, and condoms for handjobs

Topics include:
The monthly masturbation challenge
How do I make anal sex enjoyable for her?
Periods and vacations and sex
Aging and orgasm struggles
How do I know if I’m in right?
Does fantasizing about my husband make it a shared experience?
Condoms for handjobs
Resources for newlywed virgins

Welcome to another roundup from our Anonymous Questions page.  These questions come with only the context given in the question with no contact information and I post it in our supporter’s forum for discussion when they come in.    Every month or so, I take the questions that are submitted on that page and answer them as best as I can from my experience, knowledge and the discussion of our supporters who weighed in.

These are the questions we received in January and February of this year.  Minus two that I’m going to be answering separately.

Question 1 – The monthly masturbation challenge

Masturbation is not shameful. Why do we have so many unqualified ppl giving advice in society today?

What would make them qualified? Judging from the question, I suppose if they agreed with you? This is what we call confirmation bias, which leads to an echo chamber effect. In short, you only accept, listen to, read, etc., views that already agree with you.

Then, you find a way to downplay, disparage, or call into question the authority of anyone who disagrees with you.

Now, I have many posts where I detail why I think solo masturbation is wrong. You’re, of course, welcome to agree or disagree, but simply stating that it’s not a problem without any reasoning doesn’t really lend any credence to your stance.

So, if you have an actual argument to make, make it, and I’ll happily discuss it.

Question 2 – How do I make anal sex enjoyable for her?

Hi, I would like to explore anal sex with my wife. She likes soft touching on her butt however she says that penetration with my finger is not comfortable. I use plenty of lube and I take plenty of time. I think she would be willing to try anal sex if I would ask her to try it. However I have no desire to stretch her past her comfort zone as I want all of our sex to be mutually enjoyable. As you could probably guess, my penis is significantly larger than my finger. Does anyone have any ideas on how I can graciously progress towards a sensitive attempt at anal sex with my wife? Any feedback will be appreciated! Thanks, 

The short answer is that you should not. If she doesn’t enjoy a finger – she most likely will not enjoy a penis. If you both want to explore in this direction, then I’d suggest working on simply making a finger comfortable and enjoyable. Then try to progress if you get to that point – not before.

Engaging in any sort of anal play requires being relaxed – both physically and mentally. If she’s uncomfortable with the idea, that’s going to manifest in her being physically uncomfortable because she’s going to tense up, and that’s going to hurt.  

Step one is to talk about it and ensure both of you are on board and interested in moving forward. Not just you. If she’s not – well, then maybe look into pegging instead.

Question 3 – Periods and vacations and sex

Hi Jay,

My wife and I are going to be celebrating our 10th anniversary over spring break soon. Getting away for the first time in a long time without any kids! One issue though… if her calendar is correct, part of the time we’re gone she’ll be on her period. I’m sure it has come up before, but do you have any tips for sexual intimacy during one’s period? 

It comes up from time to time – I actually did a survey a while back on period sex, and I wrote a post many years ago about period sex and whether or not it’s lawful.

But I’m not sure we’ve had the question about what to do if it interrupts your vacation. Largely, that depends on your (you and your wife’s) personal views, preferences and comfort with period sex, fluids and blood. So, that requires a conversation if you don’t already know. And a conversation is also a good place to start when trying to figure out “what do we do about this?” Because what you don’t want is for both of you to have mixed expectations about what’s going to happen on that vacation and then be hurt by those expectations not coming to fruition.

Anyway, here are some quick ideas:

  1. Shower sex might be an option – that cleans up any messes as soon as they occur, so it’s easy to deal with.
  2. If you’re okay with a bit of blood but just don’t want to ruin the sheets, put a couple of towels down.
  3. Depending on when it’s supposed to happen, maybe you just skip those days. For example, if you’re gone for a week, maybe it’s just at the start or tail end of the vacation, and you get all the sexy fun before or after.
  4. If you’re okay with anal sex – that’s an option.
  5. You could try a menstrual cup – my wife wrote a post on these.
  6. You can use tampons and stick to external stimulation through mutual masturbation or manual sex.

In short, there are lots of options, depending on your own feelings about the topic. I think couples tend to get locked into this idea that sex has to include intercourse – and it doesn’t. There is a wide range of activities to do and try. You might want to grab Our Sexploration List and fill it out on the trip – that will give you plenty of options to work with.

Question 4 – Aging and orgasm struggles 

I’m not sure how to make sense out of what I’m struggling with. As I’ve gotten older, it takes so much stimulation to climax. Nipple and clitoral. My husband and I are both 61. We have a great marriage physically emotionally and spiritually, meaning we are pretty much on the same page most of the time now that kids are grown up. Sexually he’s very patient with my seemingly never-ending changes. So we really have a lot of fun but honestly it takes so long for me to have a really intense orgasm I usually just settle for small orgasmic waves. I’m usually satisfied but sometimes I wake up in the middle of the night wanting a release, then it’s like a spiritual battle. I don’t want to wake him, and I want sleep. All that being said, is this normal? I wondered if too much stimulation is causing me to be desensitized. I thought about depriving myself for a while and just take care of him for maybe a week or two.

Anyone else deal with this ???

It’s not the first time I’ve heard of it, but I can’t say how prevalent it is. I did pull some of my old survey data and checked on a few things though.

Chart showing the average length of sexual encounters increases as you get older.

The first is that, yes, as you get older (past aged 40 anyways), people claim to have longer sex sessions. It’s not a massive increase, but there is an increase.

As well, those in the 50+ age range seem to spend time engaging in sexual sessions that exceed an hour more often than those who are younger.

So, the short answer is that – yes, I have no doubt others are dealing with this.

As for what to do about it – it’s true that some at this stage of the game start to deprioritize orgasms in favour of pleasure and intimacy. They might choose not to orgasm every time they have sex in order to be assured of a better orgasm next time.  

You might also want to consider investing in a sex toy as that can help achieve a strong orgasm when they’re being difficult. 

We went through some phases where my wife struggled to orgasm, and now we have quite a collection of toys that we rarely use because we’re not struggling with that anymore. But, as we get older, we might turn back towards using them more frequently.

One of our favourites is the Limon by MinnaLife.  Sadly they have stopped manufacturing them, but they still have a bit of stock left, and they’ve heavily discounted them to clear the stock out.  If you go to the site, they’ll list the toy at $136, which was the retail price, but it will discount down to $34 when you checkout, and shipping is free in the US. So, if you’re in the US and in the market for a toy – that’s a good option to get a premium toy at a cheap toy price.

Alternatively, you can try some new sexual activities. Exploring new things tends to ramp up dopamine, which increases orgasmic response. If you don’t know what to try – check out Our Sexploration List.

And lastly – you might want to ask your husband his opinion of being woken up for sex. For myself and many other husbands – we would gladly sacrifice sleep to be woken for such a task. I’m not saying he will be as happy to – but you shouldn’t assume he wouldn’t be.

Question 5 – How do I know if I’m in right?

Topics include:
The monthly masturbation challenge
How do I make anal sex enjoyable for her?
Periods and vacations and sex
Aging and orgasm struggles
How do I know if I’m in right?
Does fantasizing about my husband make it a shared experience?
Condoms for handjobs
Resources for newlywed virgins

This is embarrassing, but how do I know if I am in right?

Turn the light on and look. Or ask your wife. Or both.

Question 6 – Does fantasizing about my husband make it a shared experience?

Just a quick question

I believe that fantasizing brings that person into your experience then wouldn’t fantasizing about my husband if I wanted to masturbate bring him into that experience?

I’m assuming you’re addressing my stance that all sex should include your spouse, and you’re trying to justify solo masturbation by saying you’re fantasizing about your husband.

And I get where you’re coming from here. After all, I would say that if you’re fantasizing about someone else, then you’re committing adultery because you’ve brought them into it. However, that’s true in one sense but not in another. They aren’t committing adultery because you fantasized about them.

In the same way, your husband isn’t there just because you’re fantasizing about him. So, he’s not involved from his perspective, and I believe sex should be a shared experience. He is not participating. You’re only including him in a one-sided sort of way.

Question 7 – Condoms for handjobs

I listened to an old episode on using condoms for hand jobs and want to use condoms. (Episode 82 – Question 3 or Episode 85 – Question 3) Is it something a lot of married Christians do? Worried he will not be happy and say nobody does that. I asked a small group of friends and 1 always uses condoms and the other 2 liked the idea but worried about asking their husbands. Do I tell him all that?

I’m not sure how many Christians do this. I was quite surprised when I got the first question, and that was within the last 6 months, after doing this for over a decade.. Prior to that, I don’t think I’d heard of such a thing in marriage. Usually, one hears about using condoms for handjobs when you’re worried about spreading STIs – which hopefully isn’t a concern in your marriage.

Anyway, I can definitely say that it’s not true that nobody does that. However, I cannot quantify at all how many people do it yet. I’ll have to ask in a survey one day to get a sense of that.  

I guess my question is – why would you want to? If it’s an aversion to ejaculation, then I could definitely see your husband not being happy about that. I think many men would feel personally offended by that as it would feel like a rejection of them.  Other would be okay with it, so long as it meant more sexual intimacy.  Some wouldn’t like the decreased sensitivity.  Other won’t like the barrier to skin on skin contact and the effect on feeling close and connected.

But you’ll have to talk to your husband about it to figure out what his views are.  And just ask what he thinks about it – don’t try to convince him or make him do anything.  Just have a conversation and then decide together.

Question 8 – Resources for newlywed virgins

Resources for virgin newlyweds? 

I keep meaning to start a list of resources for things like this. I asked my supporters, and they recommended Our Sexploration List (of course) and Intended for Pleasure by Ed and Gaye Wheat (which I have not read, so I’m trusting their recommendation). I would say Married Sex by Gary Thomas and Debra Fileta is also a good down-to-basics book.

I have an entire bookshelves that I read years (sometimes decades) ago that I should really go through and write proper reviews of. I have done some – you can check out the book reviews I have done here, but I’ve got many more I have to catch up on or refresh my memory on.

And that’s it for today.  If you have a question of your own, you can submit it on the have a question page, and if you’d like to see them as they come in and be part of the discussion, you can join the forum anonymously as a supporter here..

Looking for more help?


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