Real advice from the men who’ve been there
We asked a simple question on Reddit: What’s the one thing you wish you’d known before trying pegging?
Ninety-seven answers. Forty-seven thousand views. Turns out men have a lot to say on the subject — once someone actually asks.
Here’s what they told us.
“I wish I’d done it sooner.”
The most upvoted answer in the entire thread. By a lot.
Men who’d been curious for years described finally trying it and wondering what took them so long. This one isn’t really about technique — it’s about permission. The biggest barrier for most guys isn’t physical. It’s getting out of their own head long enough to try.
If you’re reading this and sitting on the fence, consider this your sign.
Prep is everything — and it starts solo
Multiple men said some version of this: figure out your body before you involve a partner.
Solo play isn’t a consolation prize. It’s how you learn what size works for you, how much lube you actually need, and how to relax when the moment calls for it. Couples who skip this step often have one painful attempt and give up entirely. That’s a shame — because most of the time, the problem isn’t incompatibility. It’s preparation.
Clean out properly too. Confidence in your prep is the difference between being fully present and spending the whole session in your head. Whether that’s a bulb or a full kit is personal. But don’t skip it.
Lube. More than you think. Then more.
This came up in almost every thread. The rule of thumb from the men who’ve been doing this a while: just when you think you’ve used enough, use more.
And applying it on the outside isn’t the whole job. A lube shooter gets it where it actually needs to go — several veterans called it a game-changer.
One more note on compatibility: oil-based lubes break down silicone toys and condoms. Water-based is the safe default. Silicone-based lasts longer but check your toy’s material first.
Start smaller than you think
One commenter put it perfectly: your eyes are wider than your ass.
Start with something realistic. Butt plugs as warm-up aren’t optional — they’re the difference between a good first experience and one that puts you off the whole idea. Go small, go slow, and let your body lead. You’ll get where you want to go faster by not rushing.
One practical tip that came up: longer tends to be better than shorter. Shorter toys slip out. Longer ones stay put.
The push-out technique
This surprised a lot of people in the thread. Bearing down slightly — like you’re trying to push out — relaxes the muscles and actually makes entry easier. It sounds counterintuitive. The body mechanics make sense once you think about it. Worth knowing before your first time.
The emotional side will surprise you
This was one of the most recurring themes — and the least expected.
One commenter described it as something he could not have prepared his brain for: how emotional and intimate it was. The vulnerability of being the receiver created a level of connection with his partner that caught him completely off guard. Multiple men described feeling closer to their partners afterward, describing a deeper bond that changed how they approached their relationship.
One man who’d been doing it since the early 80s said it changed his entire attitude toward sex — making him a better giver because he finally understood what being a receiver was like.
Nobody warns you about this part. But it might be the most important part.
It’s not just physical — your partner matters
Solo play feels good. But several men were clear: having a partner in the mix is a different experience entirely.
As one commenter put it: it’s not only the penetration that feels good, it’s who is doing it. The mental component of being with your partner — the trust, the eye contact, the dynamic — is what takes it to another level. Solo practice teaches you your body. The real thing is something else.
Communicate. Before, during, and after.
One comment just said: “Communication.” Fourteen upvotes. Nothing else needed.
No couple accidentally ends up in a pegging session. It requires an honest conversation before anything happens — about curiosity, about pace, about boundaries. Partners who learn to read each other’s signals get dramatically better over time. But when you’re starting out, say what feels good, say what’s too much, and keep the lube within reach.
Once you try it, you probably won’t want to stop
Several men mentioned this unprompted. One simply said: it’s addictive — try it once and there’s no going back. Others described wanting to progress to larger sizes over time.
There’s no judgment here. Knowing this going in just means you can set realistic expectations — and maybe invest in a good harness sooner rather than later.
The bottom line
The men in this thread aren’t outliers. They’re curious guys who tried something new, prepared (or didn’t), and came out the other side with real wisdom to share.
The themes are consistent: start sooner, prep properly, use more lube than you think, and don’t underestimate the emotional depth of what you’re exploring.
Uncharted territory is only scary until you’re in it.
At Hello Sailor, we carry everything you need to explore with confidence — from quality lubes to beginner-friendly harness kits. Browse the store or head to the Captain’s Log for more guides like this one.