Pegging How-To: Beginner Tips

When my husband expressed he was interested in pegging (strap-on sex where a male or person with a prostate receives a dildo anally), it was like a whole new world. I had so many questions. How does it work? What do I use??? Sexy and…kinda kinky. For me, it was like uncharted territory, exploring a new country. Flash-forward 5 years and 2 strap-on sex partners later…

Let me guide you through pleasure vs. possible pitfalls with pegging! This Pegging 101 intro will cover all of: (1) My top picks for pegging gear, including harnesses and anal lubricants; (2) Beginner anal training tips (how to expand his butt safely); (3) First pegging dildo recommendations, all body-safe silicone; (4) Making sure you’re both getting pleasure from strap-on sex; and (5) If you’re not both onboard yet, ideas for how to talk to your partner about pegging.

Beginner Pegging Sex Toys: Top Picks

First milestone: getting over the fact that having something inside your rectum feels weird the first time or two you try it. I promise, it gets better if you stretch safely. That’s why I recommend anal-prep gear first, including really helpful tools like a lube shooter. (Dry ass = discomfort with penetration!)

Pegging Gear Pt. 1: Anal Prep.

• Lube launchers. A.k.a. Lube injectors, shooters, or applicators. These hollow tubes will slick the rectum up, after you insert them 2-3 inches inside the anus and use the plunger to push the lube inside. Nonporous plastic launchers are safest: for one, the 3-loop design of the b-Vibe Lube Applicator kit (3 launchers) is easy to stick your fingers into and push down, to eject lube while your other hand is busy.
• Beginner plug set: If the pegging-receiver doesn’t have previous anal experience. The Mood Naughty Kit has 3 plugs that (1) start super-small, (2) work up to beginner-intermediate size by the biggest one, and (3) have a canoe base, so your ass cheeks don’t get chafed (round bases will chafe!) if you’re walking around with the plugs in. It’s best spend at least 2 weeks moving from the small, to the medium, to the large plug, with breaks in between (i.e., give your butt a rest about every other day). Start with wearing the small plug for about half an hour; work up to 1–2 hours with the large plug inside. Then you may be ready for some thrusting. 😉
• LUBE LUBE LUBE. I strongly prefer hybrid lubricants for anal: they’re thicker, they coat better and last longer than water-based lubes, but are still easy enough to wash off silicone dildos & plugs.
• Or get an all-in-one prep kit: This Lux Active set includes 3 tapered silicone plugs, a plastic lube launcher, storage bag, and a so-so bullet vibe (for buzzing the perineum or frenulum of the penis as you plug).¹ The Lux Active plugs do have round bases, but with strong suction cups. The butt plugs have less drop-off between the widest plug diameter and the plug’s neck below, so they don’t lock into place as securely as the Mood Naughty Kit. My good friend Travis finds their round bases less comfy to sit on, but he enjoys how they move up and down inside his ass when he walks around and clenches his anus (does kegels). He says this feels GREAT and makes him produce “so much precum.”

Pegging Gear Pt. 2: Harness & Dildo!

• A harness. It’s essential!² I like the Temptasia Briefs ($16.99!) (=better clit stimulation for me, read why here) and the Spareparts Joque (=sturdier, supports the dildo a bit better).
• A starter dildo. For this one, it’s tough to pick just one right answer, but a good first pegging dildo should be preferably (a) 1.25 inches diameter or less; and (b) not too textured, keep it simple. Browse top choices here: first, Neo Elite 6 Inch Tapered ($23.99; dual-density, comfortable feel, small tip); Ergo Mini ($31.99; dual-density, slightly wider head, light prostate stimulation); or the silkiest feel, Strap-On-Me Dual-Density Bendable ($59.99 or $69.99 for small vs. medium respectively; silky 3-layer silicone; bends for different angles of penetration). Read a detailed first anal dildo comparison below🔗.
• For (her) pleasure too: A small vibrator. The harness wearer should be having fun as well! I know I like vibration and/or being filled vaginally when I strap it on: so I wear only harnesses with a vibrator pouch to support a toy for my enjoyment. The Essential Bullet is a great first pick; or go with the Intense Travel Vibe for a bit stronger grrrr.

Step 1: Anal Training

First tip. Don’t jump straight into anal thrusting.

You’ll want to warm up over a period of several weeks to a month. Employ small plugs, mini-dildos, or fingers before you start receiving full-on anal sex. This is important because the anus is naturally closed, surrounded by the sphincter muscles (two sets of muscular bands). Since they are muscles, you can work them out; train them like any muscle group. You can teach them to stretch, safely.

Like with a hard-core workout, you can tear things if you go too hard too fast. So it’s important to not overdo it. What that really means is: you wanna listen to your body and stop if you feel actual pain signals (rather than a slight weirdness as your sphincter muscles & anal canal are getting opened up). Especially when you’re just taking your first anal plugs, the butt plug may feel foreign, unusual, because it’s just something that your brain is getting used to.

Start with a small anal plug, then move up in roughly quarter-inch steps: 0.25 inches more diameter between one plug and the next one. It is possible to train yourself using fingers as well. Especially if you have a willing partner, then that route will be easier. (Even though fingers don’t get you used to keeping toys inside your butt, like longer pegging sessions will involve.) One finger should be simple to start with; then move up, with ample lube.

A good beginner butt plug set is key here, as as good lubricant. See the 3 Mood Naughty plugs, below:

Second tip. Plugging + kegels too?

So, I seriously believe everyone (who doesn’t have chronic pain from penetration, like vaginismus) should try kegels. These clenches strengthen the pelvic floor muscles, from ass to the genitals. That means they can help you have stronger orgasms. Kegels were developed for women postpartum, because they help with not peeing on oneself while sneezing or coughing; but they’re great for improving anal play as well. “Kegeling” can also improve control over erections.

Doing kegels while plugged can make the butt plug move up and down a bit, like little tiny thrusts; and helps with control when moving toward prostate orgasm. This exercise intensifies the buildup toward orgasm.

Step 2: First-Time Pegging Sex

Your first pegging session will be a whole new experience. But don’t be nervous! Remember that this is all good clean fun, and be sure to talk to your partner during the act. The more verbal communication about whether this feels good for them, the better. (Moaning with pleasure is also a valid response!)

Tip #1. Make it special. Get in the mood by having a nice dinner, or hanging out and spending some time together even if it’s watching some TV together. That way you’re both relaxed and on the same page.

This is in sharp contrast to my first pegging session, which felt rushed! Don’t be like me here, have a free evening where you and your partner can relax and be mellow for a sexy new experiment.

Tip #2. How will the strap-on come out?

Two approaches for putting on the strap-on, depending on your relationship. Pick: 

• Like putting on a dramatically sexy show? Have the femme partner figure out how the harness fits & how to get the dildo in its hole. She’ll strap it on, walk out, and show her partner the new dildo-decked look. 
• Like figuring things out together as a pair? If the receiver wants to be in on the whole process (maybe it excites him to watch the strapping-on), you’ll both take the harness & dildo out of their packaging. Discover together how the setup works.

Tip #3. Get LUBED.

A lube launcher is really recommendable because the inside of the rectum will not be slicked up unless you shoot lube up in. If you apply lube to the toy, that’s not bad, but you’ll need to apply more and it’s more likely to ooooze out the butt instead of actually padding the thrusting.

Tip #4. Work that tip in, nice and slow.

So the beginning of the butt is the tightest part! You’ve got the anus, surrounded by inner & outer sphincter muscles that keep it closed. The anorectal ring separates that first couple inches of opening from the rectum.

And the opening “ring” area feels great when teased. Gently!

First, you gotta get it in… Use your hand to insert the very tip of the dildo.

Then… wiggle the thin dildo tip right inside. Go sloooow and know that you are making your partner’s ass feel what it’s never felt before. You can even hold the dildo’s mid-shaft in your hand and move it in small circles, like dildo rimming.

Hopefully, you’ll hear them breathing faster and moaning a little already. Are they ready for more? They better say so, and then you’re on to…

Tip #5. Start thrusting, with short strokes.

So you’re in. How to thrust? Lean forward slightly, move your hips back and forth… but not too fast. Let your partner get used to the feeling, let them get a sense of what feels good versus what hurts.

That may take some time, at least several sessions: as they get used to the anal motion.

Tip #6. Reposition if needed.

Finding the right positioning will probably take some exploration! You may need to adjust how the dildo base sits on the harness-wearer’s pubic mound; may need to put more pillows under the receiver’s butt for better access, etc., etc.

Find your comfort zone, and keep playing. Body positioning is the toughest aspect of pegging, IMO: “anal doggy” is the easiest starter position, so the receiver is on their elbows & knees, with the giver coming in from behind. Only tip there: If you’re using a prostate-seeking dildo, you’ll need to turn it to curve downward, not upward!

Anal missionary is possible too, if the anal-receiver does wanna be in total control of the depth of penetration. Only downside: Their legs will be getting more of a workout, and many guys have the urge to lie back and not move when anal orgasms begin, so they don’t want to keep riding.

Tip #7. Penis play too!

As the session progresses—especially a first pegging session—it’s smart to add penis stimulation into the mix. “Finishing” by stroking to ejaculation makes sense as you get used to anal thrusting. (Because it’s good to work up to longer sessions, rather than diving right in and expecting to shoot streams hands-free immediately.)

And you’re not weird if you can’t have a pure prostate orgasm. Some people can, some people just cannot—similar to how it is with G-spot orgasms, where the majority of people with clits need that stimulation too.

Tip #8. Don’t be afraid to stay “stop.”

Either one of you may want to stop or slow down, whether it’s to relube or because the thrusting feels too fast, etc. Keep your lines of communication going! That’s how everyone will get the most out of the first pegging session.

Fun for Both Partners?

In general, I strongly recommend that the strap-on harness wearer have some kind of extra stimulation to enjoy while pegging her/their partner. Wearing a harness just doesn’t provide direct stimulation—though the act of being in control, or watching my partner’s pleasure vicariously, has been appealing to me before. But… it’s not overwhelmingly orgasmic, not unless I’ve got toys going on myself.

See my Double Pleasure Strap-On Sex guide for full list of ways a harness-wearer might cum while strapping on. I’m the biggest fan of a G squeeze vaginal plug for when I want to be penetrated at the same time as I’m fucking my partner (it’s so filling); and I also really really love the strength of the small & affordable Intense Travel Vibe, slotted into the Temptasia Briefs harness below,³ vibrating under my clit and labia.

“Strapless” strap-on dildos are the solution that I’ve seen people suggest first, most often. I personally think it’s gimmicky and borderline lying to call these toys “strapless,” since wearing on without a supportive harness is tricky, and likely uncomfortable if you do it for more than a few minutes. But! I do think vibrating “strapless” double dildos can be nice: like the good vibes, 3 motors, and remote control of the very-flexible (=better fit!!!) Strap-On-Me Vibrating, but inside the Temptasia Briefs for support.

More on Pegging Dildo Choices

Oooh, the dildo matters! You want a toy that’s not too large, to be more comfortable your first times. (And that’s made of body-safe silicone, so it doesn’t harbor bacteria like PVC and “jelly” toys do.) This usually means a toy that’s 1 inch to 1.25 inches maximum diameter. My top picks:

1. Neo Elite 6 Inch Tapered (dual-density) or Avant D15 (soft silicone, pretty colors). Why? Because it’s an easy 1-inch diameter to start: slips in easily, then moves to 1.25 inches (still not wide). The dual density version is super-soft outside, over a firm core for stability; while the pastel version is pretty soft, still comfortable, and I’ve used it for very successful results for a guy who’d never been pegged: he came so hard 10 minutes in, stroking himself. Couldn’t wait till the next time. (The dual-density version was released later!)
2. Strap-On-Me Dual Density Bendable. Super-soft feel overall too, but posable. The small size is very small; the medium size is pictured above, and still pretty slender. Read about my experience here. I think it’s the most luxurious option for first-time pegging.
3. Avant Ergo Mini (dual-density) or Avant D16 (soft silicone, pretty colors). Another toy shape (like #1) that’s available in either dual-density silicone or just medium-soft silicone/pretty colors. At just over 1.3 inches but soft, it’s takeable with warmup. It has a ridge that can pull, lightly, on the prostate: a little more in the Avant D16’s firmer (but not hard, 10A) density.

PROSTATE DILDO PICKS:

Woohooo, prostate play! The “male G-spot” can be a magical zone. Once you’ve had a few pegging sessions, and you’re at a more “intermediate” level of anal training, then these prostate dildos will be fantastic. (I consider “intermediate” being able to take an average-girth, 1.5-inch diameter dildo with minimal warmup, and no pain.)

The Neo Elite 7.5 Inch with Balls realistic dildo is a well-liked choice; popular for prostate as well as G-spot. See what my colleague All Male Sex Toys has to say about its 5.5 inches insertable length here. It’s an affordable dual-density toy; an excellent price for the 2-layer platinum silicone contruction. The 7.5 Inch with Balls’ protruding ridge can really tug the spot, and it’s suction cupped.

Want more P-spot massage? I designed the Peg’Em triple-density dildo to have 5 ripples, pulling in a row as the dildo moves in and out. The prostate (like the G-spot) responds to (1) inward pressure, so it’s got a protruding ridge + forward curve; (2) and downward motion, so the extra waves under the main “head” keep contact for longer on every downstroke, as Peg’Em’s shaft segues outward toward the anus. Peg’Em’s got a squishy dual-density feel (super-soft 00-30 Shore silicone inside) but with an extra “skin” layer on top, so it’s not sticky like VixSkin dildos can get! It is handmade, certified skin-safe platinum silicone, with Electric Blue pigment.

And, for the most serious pressure tool: The Njoy Pure Wand is the prostate toy par excellence. You’ll understand why when you feel the weight of this steel dildo’s curved bulbs inside your body. It’s intense. On how to use the Pure Wand for prostate here.

Or, just looks amazing: Dildolls Utopia looks stunning, and is a solid toy. Streamlined, semi-soft, a gentle ridge. I say, pair it with a Magic Wand on the penis head or under the balls for more stimulation. (Though I will say, that’s problematic sometimes because I’m always wanting to steal the Magic Wand R and use it on my clit 😂 That’s a classic sex toy for a reason!)

Let’s Talk about Pegging

How do you begin pegging with your partner? First is obviously talking with them about whether they’re down for a new kind of sex play.

To have fun pegging, you need to be free of two underlying assumptions: which someone may not even realize that they believe. These are: (1) that anal sex is dirty or gross, and (2) that “real men” don’t take it up the ass. (That belief is a form of toxic masculinity).

Avenues & example questions for easing toward pegging, and a healthy discussion with your significant other:

• Explore anal plugs & anal play together, both of you. “I love your ass, I’d like to play with it more…Have you been interested in anal?” Or “I’d love to see that ass with a little plug peeking out…” If they express an interest, say you’re interested too, and maybe “I hear having your anus filled can feel incredible, I wonder if I should check out a plug too.”
• Rimming/ “finger-rimming”: The easiest way to move into anal is one well-lubed finger. Groping their butt during your “normal” sexy time, perhaps; then asking if you could tease their asshole with your finger / or would they would do that for you, it could be fun! For anyone who’s feeling well, it’s basically impossible to not get turned on when your asshole is circled, outside, lightly with a finger.
• “I saw this porn clip”: This one’s a possibility if your partner likes watching porn with you. “This guy was getting railed from behind and came all over…”
• Dominance: “Have you ever wanted to fuck me like you own me?” Some women do like being in charge in bed: you may know if that’s the case with your partner; or simply ask them if they’d like to be in control. Orgasm control, post-orgasmic “torture” (where the penis is stimulated after a first orgasm), and femdom type scenarios are associated with pegging for some couples.
• Intellectual approach: “I’m super curious about prostate stimulation, have you heard what the prostate does?” Learn about the pleasure points inside your butt, and how they connect to pleasure & fertility. The prostate is best-researched: It contributes ≈30% of semen volume, and people who have had their prostate removed cannot ejaculate.

Like in any conversation about new territory, it’s important to let the other person know you care about their perspective and their pleasure. Praising them, listening to them, and expressing desire for them in words are all markers of a healthy, sustainable relationship. If either person doesn’t feel respected, valued, or desired enough, there will be issues.

Of course, not everyone will be into strap-on sex; it may be too exotic or non-standard for traditionally minded folks.

I consider myself open to new perspectives and generally curious to learn: but the oddest part of pegging was the first time I strapped on a silicone dick. Because it’s a role-reversal. Knowing that I was the penetrator, for the first time ever—that was both weird and super-interesting at the same time. And it was an adjustment! Wearing a dick has become less odd to me with time, and now it’s just an occassional part of the fact that I love making my intimate partners satisfied.

What’s your story, and how will / how has strap-on sex changed it?

NOTES

1. This anal trainer kit also has a douche bulb/enema with “backflow prevention.” It’s a silicone bulb, which is hygienic. Some people feel the need to douche between anal play; however, it’s not necessary, and you may be able to time your anal to begin about 3 hours after the last time you pooped. Douching does wipe out the normal anal bacteria, which isn’t the best for health reasons, as good bacteria aid in keeping the immune system in top condition.
2. Read about why I think “strapless” strap-ons are BS here; a harness makes those double dildos much more usable.
3. Not all harnesses will have a place to put a vibrator, which is why I like Temptasia Briefs or the Packer Gear Brief, and the Spareparts Joque’s pouch is fine for holding a bullet vibrator too, just a little more open.