Vanilla Swingers – A swinger podcast for newbies, by newbies in the lifestyle
Pegging is one of those things people whisper about like it’s a political scandal or a celebrity sex tape. But once you strip away the taboo, you’re left with something pretty simple – anatomy, pleasure, connection, and a whole lot of lube. Men have prostates. Prostates feel amazing when stimulated (Leo would not know). And a strap-on is just a tool that lets you play conductor to his personal symphony of “oh my god why didn’t we do this sooner?”
Now, full disclosure – pegging isn’t currently on my personal bingo card. Unless… a certain thirst trap happens to wander into my bedroom and says, “Teach me femdom.” In that case? I’m strapping in so fast the harness might start smoking. But for the rest of you, this guide will take you from curious to confident.
Don’t forget to check out more newbie swinger advice in our Vanilla Swingers podcast.
Let’s get this out of the way – pegging has nothing to do with sexuality and everything to do with pleasure. The prostate is basically a built-in orgasm button, and when stimulated properly, it can deliver sensations that make a regular orgasm feel like a warm-up lap. This isn’t about dominance, humiliation, or proving anything – it’s about exploring a part of the body designed to bring joy.
Not only that, but pegging can deepen trust and intimacy between partners. There’s a vulnerability to letting someone touch you in a new way. There’s power in learning how to guide someone into pleasure they didn’t even know was possible. And honestly? There’s something deliciously fun about reversing the roles for a night and watching your man discover his hidden superpowers.
Your first strap-on should be gentle, not terrifying. Too many beginners buy something massive because the packaging was “cute” or because Amazon suggested it at checkout. No. Absolutely not. You want small, smooth, and friendly. Think “starter penis,” not “alien warlord.” Silicone dildos are the gold standard – firm, body-safe, and easy to clean.
As for harnesses, avoid the $9.99 elastic ones that come with questionable stitching and a prayer. A good harness should feel like underwear: stable, comfortable, and confidence-building. Nylon is secure, silicone is comfy, and leather is a vibe, but not necessary for beginners. When the harness fits well, you stop thinking about the gear and start thinking about the pleasure. That’s where the magic happens.
Pegging is 60% confidence, 30% communication, and 10% lube – just kidding, it’s like 80% lube. The more the merrier. Water-based lubes are great, silicone lubes last forever, and oil-based lubes are banned from this conversation entirely.
Anal play requires relaxation. If your partner clenches tighter than TSA security, nothing is going in. A warm shower helps. Deep breathing helps. Dirty talk? Shockingly effective. And patience is the secret sauce. Ease in with a fingertip, a small plug, or a slim toy. Let the body adjust at its own pace. Pegging is not a race – it’s a very sexy yoga class for two.
No one goes straight from “never touched” to “strap it on, coach” in one night. Starting with fingers or small anal toys gives your partner a chance to understand what sensations they enjoy and what they don’t. A single well-lubed finger can be a revelation. A small plug can help someone get used to fullness. And using toys together builds trust before bringing in the harness.
Once your partner is relaxed enough to crave more, that’s when the strap-on becomes your new favorite accessory. Patience builds anticipation. Anticipation builds arousal. Arousal makes everything easier and hotter. It’s like sexual physics.
Doggy-style is the classic starting point for a reason – the angle is great, the access is perfect, and your partner can relax while you explore. But don’t sleep on missionary pegging – lying on his back with legs up lets you see his face, check in on his comfort, and create a deeper connection. Spoon-style pegging is perfect for beginners who want something soft, slow, and intimate.
The goal isn’t to look like porn. The goal is to find the position where you both feel grounded, safe, balanced, and turned on. If you’re laughing half the time? Even better. Pegging is supposed to be fun.
A shocking number of men are terrified to enjoy anal pleasure because they think it threatens their masculinity. Let’s be clear – masculinity does not come from which direction pleasure enters your body. Pegging doesn’t make a man less straight, less dominant, or less anything. It makes him more self-aware, more open, more curious, and—let’s be honest—more fun.
There’s nothing sexier than a man who isn’t scared of his own anatomy. That’s grown-man energy.
Look, not every kink is meant for everybody. If pegging isn’t on your radar or your partner’s, that doesn’t make you vanilla, boring, closed-minded, or failing Sex Olympics. It just means it’s not your flavor. And that’s fine. You do you, they do they. There are a thousand ways to be a great lover, and none of them require a harness unless you want one. Pegging is simply one of those things you may see on Feeld profiles, hear whispered in Bliss playrooms (yes I did). It’s an option, not an obligation. Curiosity is cool. Interest is cool. Disinterest is also cool. Zero pressure, zero shame, just grown adults choosing their own adventure.
So strap in, baby. Or strap on. Your call.
Find all of this and more on this episode of our top-rated swingers podcast for new couples to the lifestyle, the Vanilla Swingers podcast!
Pegging: When a woman straps on and gives her male partner the business – power, penetration, and prostate pleasure all in one delicious role-reversal. It’s kinky, it’s intimate, and in the lifestyle it’s way more common than guys admit. Peg him once and suddenly he’s VERY interested in buying nicer lube.
Femdom: When a woman takes the reins – commanding, teasing, controlling, and calling every sexy shot. Femdom flips the script so she leads the play, while her partner submits, obeys, or worships accordingly. Think stiletto heels, confidence, and “yes ma’am” energy.
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