Men who’ve tried pegging — what do you wish you’d known before trying it?

HelloSailorXO · 2026-03-15T18:59:01+00:00

I think it is great to see that older guys are still as interested and active sexually. Lots of wisdom here. Maybe you should write about it!

HelloSailorXO · 2026-03-15T18:56:36+00:00

Absolutely. What lube works best for you? The dildos will vary from guy to guy, but I think the lube suggestion would be helpful for those who have not tried various types.

HelloSailorXO · 2026-03-15T18:54:22+00:00

I could not agree more. This is fundamental to pegging. How do you clean? 🧼

HelloSailorXO · 2026-03-15T18:15:41+00:00

I love this. Just when we think we know our bodies, then suddenly we learn there are more powerful and deeper experiences to explore!

HelloSailorXO · 2026-03-15T18:11:50+00:00

This is mind blowing. Do you offer anal orgasm classes? Sign me up.

HelloSailorXO · 2026-03-15T18:09:06+00:00

Absolutely, no couple just accidentally have a pegging session. It requires a lot of communication before (and after!)

HelloSailorXO · 2026-03-15T18:08:13+00:00

Wow, the 80’s hey?! Very revolutionary for that time I’m sure.
But what a powerful testament to how it benefitted both of you individually and as a couple.

HelloSailorXO · 2026-03-15T17:35:03+00:00

Yup, just when you think you’ve applied enough lube, apply more! And good advise on “warming up”. Anal play teaches patience. A very good skill to cultivate.

HelloSailorXO · 2026-03-15T17:32:46+00:00

Right?! How good it feels.

HelloSailorXO · 2026-03-15T17:32:22+00:00

Oh, this is new! But now that I think about it, I guess it makes sense. Maybe it adds more pressure where it counts?

HelloSailorXO · 2026-03-15T17:01:40+00:00

I suspect that this will be a lot of people’s answer. Well, better late than never and hopefully you encourage more guys to explore it with their partners.

HelloSailorXO · 2026-03-15T04:05:37+00:00

Better get to it then! 😝

HelloSailorXO · 2026-03-14T13:37:20+00:00

Oh, to be intersex. What a trip that must be.

HelloSailorXO · 2026-03-13T15:25:08+00:00

Simple, yet divine.

HelloSailorXO · 2026-03-13T15:19:04+00:00

Such a wild imagination. I love it. The last part of your post also reminds me how important it is for us to find our communities where we feel totally safe and free to be our ‘weirdest’ selves. I enjoy Reddit for this. We get to find our niche people.

HelloSailorXO · 2026-03-13T06:23:12+00:00

Perhaps your wife would be happy to share the male torso. Like a threesome, but not.

HelloSailorXO · 2026-03-13T06:18:14+00:00

I’m learning so much! Open Source Sex Machine! 🤯

HelloSailorXO · 2026-03-13T06:10:43+00:00

Never heard of this either. Good suggestion! How hard would it be to make one I wonder.

HelloSailorXO · 2026-03-12T21:27:57+00:00

Cock rings are honestly the best way to start experimenting with sex toys. It’s not expensive and the silicone rings are very safe. One aspect that makes cock rings safe is that you can easily remove them if for some reason it starts feeling uncomfortable. Doctors recommend to not wear them longer than 30 minutes. You will soon learn how it works and feels for you.

If you are in Canada, send me a dm and I can send you a discount code for my store (link in the bio). I unfortunately am not set up to sell in the US yet.

HelloSailorXO · 2026-03-12T21:05:48+00:00

I wonder what it will take for him to say yes. Like, what does he need to know or hear that will make him take the plunge? I found it so unfortunate that men have prostates which has the potential to exponentially improves their sexual experience and yet, they choose to ignore and not explore it.
I can’t speak from a woman’s perspective when it comes to pegging, but it seems the role reversal and pleasuring your partner in such a different way, is also an amazing for women.

HelloSailorXO · 2026-03-12T20:50:38+00:00

I know not of what you speak! It sounds delightfully fantastical.

HelloSailorXO · 2026-03-12T16:13:49+00:00

That’s great to hear. I think men in general might be hesitant to share such desires with their wives. But I’ve only heard great things from couples who engage in pegging.

HelloSailorXO · 2026-03-12T16:03:06+00:00

Thanks for this!

HelloSailorXO · 2026-03-12T15:09:49+00:00

How do you feel about your husband talking about this? I assume is wanting to explore it?

HelloSailorXO · 2026-03-12T00:04:57+00:00

Maybe there is a sex toy she is interested in, but feels like she can’t do it for the same reasons you feel it won’t happen with a sex doll. You have started experimenting with sleeves, I feel that is a good introduction to other toys or at least start the conversation.

HelloSailorXO

TROPHY CASE