The 10 Best Pegging Strap On Sex Toys in 2019, Side-by-Side Comparison Chart

best pegging strap on sex toys cover

After more than 60 hours of research, reviewing over 150 strap on dildos, harnesses, strapless strapons on pegging toy kits, we've uncovered the 10 best toys that worked across hundreds of couples. We crowdsourced a ton of pegging enthusiast and sex toy expert opinions. The Tantus Beginner's Kit (comes with harness + 2 dildos) was the best bang for the buck for most couples. 

Then the one of the rare strapless strapons that worked was Fun Factory Share (though some preferred ShareVibe with vibrations). The best hands-down most loved harness was Spareparts Joque that won in all comfort and satisfaction departments.


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tantus beginner harness dildo kit

Tantus Beginner's Kit
The best strapon kit

Tantus combo kit comes with 2 different size dildos, 2 O-rings, a bullet vibrator and a good enough harness. It's a great first buy for new pegging fans as you don't need to worry about dildo/ring/harness incompatibilities. Plus, bullet let's you experience vibrations on cheap to see if you like them at all.

Our Pick

Silicone dildos are great quality and will be always handy, even when you upgrade to higher quality harness.

They will always be a part of your warming up ritual. This kit was the most loved as it simplifies the first tough pegging decision. 

For intermediate couples Tantus has another kit with bigger and longer dildos for $90.


best budget strapon dildo plus harness kit

Lovehoney Strapon Kit
The starter's choice

This is the cheapest, yet quality kit which has a high quality, 7" length dildo and a harness. It might be a bit too big if you're new, so you might have to use a smaller butt plug or finger first. The defined head and angle gives a nice P-spot or G-spot stimulation.

Budget Pick

If you're "strapped" for budget and really aren't sure if you will enjoy this pegging play at all, it may be smart to go with the most basic kit.

It comes with one dildo + one harness - the most budget quality pick that's out there.


Your Introduction To Strapon Sex Toys

If you're new to pegging, it can be insanely difficult to filter out strap on sex toys that are actually good for you.

There are so many choices are that if you're not careful you'll end up wasting lots of time, money, and might get burned with bad pegging experience never to try again…

Even with pegging strapon toys, there are so many variations to consider:

  • strapless strapons
  • strap-on dildos
  • harnesses for strapons
  • O rings for harnesses (metal or rubber?)
  • strap-on dildo and harness kits
  • double dildos

How the hell an average person can navigate this minefield without breaking the bank?

Not to worry, after hours upon hours of research, consulting with other pegging experts and crowdsourcing hundreds of pegging enthusiast opinions in this guide you'll get easy choices and easy answers.

  • For example, the overall best choice for new peggers will be Tantus strap-on 6-piece harness kit for $80.
  • Then, if you're attracted to strapless strapons it will be invaluable for you to learn that the same brand Tantus Feeldoe, Realdoe that are heavily marketed actually gave terrible experience to most couples. They are rigid, rough… not what you want.

If in past you blamed Kegels for not being able to hold the other end, know that strapless strapons are NOT supposed to be used without harness..!

Yeah, strapless strapons are attractive because they give pleasure to women, they often vibrate and sound cheaper than buying strap-on and harness.

But that's again a lie. A marketing trick.

The only strapless strapon that MOST couples had great experience was Fun Factory ShareVibe toy.

And still, you should get a quality harness (like Spareparts Joque) with it that will allow you to relax and enjoy to experience than worry about logistics.

But for most first-time peggers, you should actually just buy a lot cheaper and smaller strapon + harness kit…

Pegging itself has a quite steep learning curve as surely she has never done thrusting, doesn't know how it feels to have a penis, and how to use it the good way.

Strapless strapons will be great for experienced peggers, as it adds an extra layer of fun (AFTER YOU NAILED THE BASICS)

Yes, with the other end the woman will feel the thrusting… she can do the thrusting in the way that's pleasurable for her, instead of the other person 😉

Anyway, that's the ramble, let's jump in:


best pegging toys and strapon tips

What You Should Know About Pegging Toys?

Remember, this is a new skill you're learning.

Your man probably isn't used to having things up his ass and submitting to his woman.

Same way for woman it's a new world — to learn how to thrust, to fuck…

To remember to always keep it wet with a lube (Sliquid Silk is most loved across pegging enthusiasts) and dominate him.

There's a lot to take in at first.

Which is why you should simplify on your pegging toys initially.

Go with basics — just get a good harness and strapon. Or better yet a working kit.

Go small, go comfortable — forget about strapless first.


Decide Together On The Size, Angle & Style Strapon Dildo

Which size to go with is probably the most important decision.

best strap on dildo sizes angles overview

If unsure go slimmer, it's better to keep wanting more than experience pain and ruin the experience.

As for the length, keep in mind that you'll lose about 1" of length when the strapon dildo is in the harness.

Then you need to think about the shape (realistic, fantasy type) and angle.

Size and shape preferences are very individual. 

Some love ridges, some don't.

Some love girth, while others care more about the length and angle.

Most dildos are angled for P-spot stimulation, but you might wanna go for a smaller curve if you're new.

vibrating butt plug for pegging play

Also using a silicone butt plug (vibrating if you like it) before might be a great idea. It takes anal sphincters to relax and if you open them up before, later you can go straight to play. 

And while we're at it, if you're worried about cleanliness regime, you might wanna check this prostate orgasm guide.


Strap On Kit Will Be The Best Choice If You're New To Pegging

Truth is, in the beginning, you don't know yet what you like.

What if you don't enjoy pegging?

Which is why it's best to go for a medium-quality, medium price kit with interchangeable dildos, O-rings and harness that all fit together.

This will let you experience pegging and give a glimpse of how it feels.

Even if you decide to upgrade later, those beginner dildos will be great for warmup, so not all was wasted.


Strapless Strapons Mostly Disappoint (They're Overrated)

You'll hear me stressing this fact.

best strapless strapons compared side by side

Yes, they can be incredible IF you know what you're doing. The tactile feedback you will experience can be bonding and pleasurable.

But first, you need to learn how to fuck, how it feels suddenly having a penis, how to satisfy your partner in a way that's good for him.

Strapless strapons have a slight learning curve. You will need to experiment with various positions and angles. 

The experience is far from seamless.

So yeah, before you can enjoy it, it will suck first…even with a high-quality strapless toy.

And if you have an illusion about using the toy without a harness, forget about it.

The only pegging position where this thing will stay in without harness is if you keep your legs together, but where’s fun in there?

Don't get it as a beginner, get it as an upgrade when you've learned the basics of pegging first. 

Then strapless strapons can be amazing and you indeed might get lots of pleasure from the internal bulb while giving joy at the same time.

You've been warned.


A Good Harness Will Make Or Break Your Pegging Experience

Initially, you'll be fine with cheaper harnesses that come in the strapon kits, but if pegging becomes a regular play you'll quickly notice that your vulva can hurt over longer time.

That flat base of a dildo will keep pushing on your pelvic bone, pussy and that's no Bueno.

It's important that harness has comfortable padding and it fits like a glove. 

You need to be able to tighten it so it doesn't move around. You want to focus on the experience, not adjusting the harness.

The second issue is skin irritation if the harness isn't tightened well enough or is not made from quality material.

A quality harness like Spareparts Joque is pricey, but you will absolutely not regret that investment if you're regular to pegging.

Also, when picking harness consider whether it's for you only or you want to share it. This will affect the sizes, and you shouldn't get a Leather harness as you cannot sanitize it.


What Are The Best Strap On Sex Toys in 2019?, Side-by-Side Comparison Chart

This was a tougher chart to create as there are four strapon categories that must be mentioned:

best strap on dildos and harnesses compared in chart

Though while there are four categories, choices are very easy:

  • Best Strapon Kits — just pick one, and you'll have a good first experience. You'll get harness and dildos that fit in there. Great if you just want to have a good starting experience without reading much.
  • Best harnesses — if you enjoy pegging a good harness is MUST HAVE. With a good harness, you can mix and match between different dildos and strapless strapons. Good harness like Spareparts Joque will work with all the dildos that have a flat base and will hold even the heaviest fantasy dildos. The same can be said about the leather Aslan Jaguar piece.
  • Best Strapless Stapon Dildos — this section is short. Why? Because most strapless strapons suck. People buy it to save money and have a pleasure for women, but most of them fall short. They are too rough, too big, too rigid. There are only two strapless strapons that gave a good experience to people, yet know that you MUST HAVE a harness to use them. No amount of Kegels will help, ass sphincters will always win in strength over pelvic muscles.
  • Best Strapon Dildos — this is admittedly the weakest recommendation section. Why? Because there are simply too many great dildos and every person has different preferences. Just know that with a good harness you'll be able to use any dildo with a flat base (suction cup works too) for pegging, and let's leave it at that. The ones included are simply the pegging dildos that MOST couples had the best experience with.

best strap on kits for pegging

Now when you understand the categories, let's take a quick look at each item so you understand exactly why it made it in the chart and who it will be good for:

  • Overall Best : Tantus Beginner's Strapon Kit— Tantus makes the highest quality and affordable kit for first-time peggers. If you know you want to try pegging, want to experience quality silicone dildos that FIT in the harness + has a vibrator to play with, this is the choice. #1 recommendation if you don't yet know if you'll be serious with pegging, but are confident enough that you'll like it to spend for quality starter option.
  • Budget Choice ⭐: Lovehoney Strapon Kit — this is the cheapest option that is still okayish to recommend. It has a quality silicone dildo, and while harness could be better made, for $40 it's a great deal. This is a good choice if you're not even sure if you like pegging yet. Try fucking with dildo, try walking around the house — use it as practice/testing strapon.
  • Upgrade Combo : Spareparts Joque + Fun Factory Sharevibe — now this is for couples who want the most comfort, pleasure, absolutely the best that sexual wellness has to offer to peggers. Spareparts harness will serve for years, it's easy to clean, compatible with all pegging toys and dildos with a flat base. Then Funfanctory Sharevibe strapless strapon has awesome vibrations, dildo itself is soft and ergonomic to guarantee you get to focus on the process, not logistics.
best strap on dildos and harnesses compared in chart
  • Sportsheets Chantilly harness — if you want something not scary (pegging is scary enough) and love the looks of it — this is quality harness for most beginner strapon dildos.
  • Aslan Jaguar harness — leather just looks freaking awesome and feels great on the skin. This harness will hold the heaviest dildos, the only precaution is that you will need to take extra care to maintain it in good quality. For example, compared to Spareparts Joque you cannot just throw leather harness in a washing machine.
  • Fuze Tango— this is the second most loved strapless strapon dildo. Fuze has it's famous ridges on the dildo so as you're pegging ridges rub against the clit. It doesn't come with a vibrator but has space for a bullet vibe, and the dildo itself is more realistic which might be a thing you like (or not).
  • Tantus Charmer — this dildo is very effective in stimulating man's prostate. It's small enough to feel good for pegging newbies but big enough to be enjoyed.
  • Vixen Mustang — if you're looking for the highest realism this dual-density dildo feels the closest to a real penis. It has two layers of silicone — inner and outer which gives that skin kind of feel. It's pricey, but if you can afford it, you'll never regret the investment.
  • Fuze Velvet— finally, this is a strapon dildo that has ridges on the base giving the pussy nice stimulation during the pegging intercourse. If you don't like strapless strapons, yet want to still feel something, this could be the way. This dildo works with harnesses, just make sure you have the right O ring to support it. They come in many sizes — Harmony is for beginners and Wilde dildos are their bigger models.

The Best Strap On + Harness Kit

In the spreadsheet, I showed Tantus and Lovehoney kit.

This one has a third one (in the middle), it's just a bigger dildo version of Tantus kit shown side-by-side for easy comparison:

best strapon harness combo kit compared

If you're looking to simplify things in beginning a strapon + harness kit is a must.

You just don't need to worry if O-rings or dildos will fit the harness.

Later you can always invest in a quality SpareParts Joque, and strapon dildos will fit in there.

Even later you can keep upgrading to bigger size dildos, strapless strapons…or add a quality We-Vibe tango vibrator for the harness pouch and pussy stimulation.

…or if you absolutely know you love pegging, I say — buy once and buy quality.

Sure, you can use any of these beginner's kits to get an idea of what pegging is like, but most couples go pretty quickly to something more comfortable and better made.

So why waste your money?

You could just test if you like anal stimulation with a simple dildo or butt plug (very cheap test - consider a tail butt plug for those that love some style), enjoy that, and then save your money to buy a quality harness and go with it.

Anyhoo, that's the ramble, the decision is up to you.

I'm here to give you clear, quality choices and suggest:


Overall Best: Tantus Strapon Beginner's Kit — $79.99

This is the most loved and recommended starter kit by pegging enthusiasts.

tantus vibrating strapon harness kit

It's the best bang for the buck. You get the highest quality angled dildos, yet they are small enough to not scare off newbies.

These kits come in black or purple color.

tantus strapon kits for first time pegging specs

The only difference between kits is the dildo specs.

If you're more experienced, you might want the bigger kit for $89.99.

For the beginner's kit, the smallest dildo is pretty much the same size as a finger.

Great for warmup. And then bigger dildo is perfect for actual pegging and anal play.

For a man, it might be helpful to use the smallest dildo to get used to anal play.

And for a woman, use this kit for your own training too — walk around with it, get used to having a penis as a body part. This training will be invaluable to make actual play enjoyable.

Dildos are the highest quality part of this kit, and you'll use them for ages, even if it's a warmup so that enough makes a good investment.

They are so smooth and sleek that they basically slip inside of you thanks to their incredible design.

Here’s a super helpful video showing off the smaller Tantus kit:

The harness itself is comfortable enough, while not great, it does the job.

Note: Alternatively you can buy quality harness like Spareparts Joque and Tantus dildos that come as a kit separately — Silk Small or Silk Medium (or even large).

It holds in place and can be easily adjusted to the slimmest and curviest of people.

Some people didn't like the pad and used just the harness and O-ring. This gives the benefit of feeling the flat base on the vulva and giving access to play with the clit.

The vibrator itself is low quality and quite big so don't expect the most comfort. But it WILL give an idea and let you learn if you like vibrations at all.

If you do, then later you can simply upgrade to a slimmer and higher quality vibrator or look at vibrating strapless strapon.

Some people also use a vibrating cock ring for this purpose.

Learn more about the benefits of using a vibrating cock ring.

You have plenty of choices.


Budget Choice: Lovehoney Strapon Kit — $39.99

This is a simpler kit that comes with three silicone O-rings, one bigger dildo — 7" long and the head shape is more realistic than the Tantus kit.

lovehoney strap on kit for pegging sex

The harness itself is quite similar in quality — while it won't be able to hold heavier toys, it definitely will hold small to medium-sized dildos.

Plus, it's comfortable and very adjustable.

Not 10/10 harness, but practical and usable.

lovehoney anal pegging strapon kit specs

Note that dildo itself is quite long, yet not too girthy. It might be too much for newbies.

Other thing is that it's angled which is great for P-spot, but it's too pokey for G-spot.

A tip is to turn the dildo on the harness when changing positions, so it's always pointing towards the P-spot.

Here's video showing how the kit looks and how to use it in action:


Upgrade Combo: Spareparts Joque ($130)+ Funfactory Sharevibe ($130)

We'll take a deeper look at both of these items further down the guide, but this is the ultimate pegging kit if you want the best and can afford it.

best harness with strapless strapon sex toy

Yes, you can match the strapless strapon with the cheaper Tantus or Lovehoney harness kit, but my job is to show the most comfortable and effective pegging toys.

fun factory strapless and spareparts harness specs

As for the harnesses, you will not find a pegging expert who doesn't swear on Spareparts harness. You buy it once and it will serve forever. It's that good.

It uses Velcro straps around the waist that makes it super easy to put on, and take off. It will adjust to all sizes with ease (again, thanks to Velcro)

There is space for bullet vibes, you can remove the pad for strapless strapon. You can change O-rings and upgrade to the biggest dildos and Spareparts will hold it with ease and your comfort.

As for FunFactory ShareVibe… this is how all strapless strapons were supposed to feel. If you didn't know most of the strapless strapons fall short and 99% of cases first-time peggers are deeply disappointed.

Strapless dildo pokes their cervix on the other side…and simply doesn't hold, no matter how much Kegels ladies do.

ShareVibe is a rare exception, though be warned it's not a beginner's toy.

Yes, the insertable end gives her more sensations, but it also complicates the logistics. Now not only you need to think about good way of thrusting, but you also need to think about your sensations too.

It might be overwhelming if you're new. But it might be just what you need if you are an experienced pegger.

This video guide is really recommended so you understand the pros and cons of all things Strap-on sex-related:


What Is The Best Strap On Harness?

Now that we've established that you absolutely need a harness to operate anything strapon or strapless dildo related, what are your best options?

best strapon harness for pegging

Well, either you go cheap for the combo kit…

Or you go for extreme comfort or extreme sexiness.

  • Spareparts Joque Hardwear Harness($130) (Our Pick) — as already mentioned before this is the most loved comfort harness by experienced pegging couples. It's easy to clean, easy to use, and it's made from high-quality poly-spandex to provide breathability. It simply does everything that you would expect a quality harness to do. The only downside? It's pricey.
  • Sportsheets Chantilly Lace Harness ($45) —this harness wins in the sexiness department. It looks incredible and laced corset on the back just adds to hotness. The Sportsheets brand is well-known in the sexual wellness market with its quality BDSM toys. The only downsides are that laces are long so you'll need to figure out what to do with excess material. Then the metal poppers where O-ring and strapon go in is very hard to open. Certainly not the dealbreaker though.
  • Aslan Jaguar Leather Harness ($95)— if your kink is leather, then it doesn't get better than Aslan harnesses. It's gonna be the toughest, badass harness you'll ever own. Secure hold, soft material. Only downside? It's pain to clean and care for it. No way on 100% disinfecting this thing, no throwing in the washing machine.

Here’s a side-by-side comparison of each harness:

best harnesses compared side by side review

Sure, there are a lot more choices, for example, there are underpants you can simply wear and use as a harness.

Or…there are also specific Vac-U-lock toy type harness.

Watch this helpful and fun video explaining the secrets of harnesses, they feature Sportsheets Chantilly harness in there too:


What Is The Best Strapless Strapon?

Okay, this is usually the section that initially got couples the most excited about pegging, but after testing the strapless toys they were frustrated.

Not you.

You must know that strapless strapons are advanced pegging toys, and you really shouldn't start with them.

The first problem is that vaginal muscles are no match for anal sphincters, and your insertion point is the only point of balance.

It's gonna poke your cervix…and whatever else…as you try to figure out how to fuck for the first time.

Compare it with a harness that lets you push whatever way you like.

The second problem is that strapless strapon is marketed as a sexy toy for her pleasure.

I mean, strapless toys look awesome — suddenly her nice pussy has a penis… it looks sexy as hell.

woman wearing strapless strapon

Then, after a disappointing session ladies always blame their weak kegel muscles.

But is it true? Nope.

Kegels might help if you just focus on contracting them with legs closed, but that's not how thrusting is done.

You cannot contract Kegels and thrust at the same time. Plus, if the pussy gets wet…which it will, strapless strapon will just pop out.

This is why you almost always need a harness.

Finally, the most strapless strapons fall short — they are either too bulky, made from a too rigid material (yep, looking at you Tantus Feeldoe, Realdoe), or simply not ergonomic.

So please, if you're a woman who's reluctant about pegging — don't complicate things for yourself…!

best strapless strapon dildos reviewed and compared

The only strapless strapons that ladies have ever enjoyed (while using harness) are:

  • Fun Factory ShareVibe (Our Pick)— the toy itself looks and feels great to touch. There are two options — vibrating and non-vibrating. The vibrator is good, just noisy. If it's an issue for you, go for $106 non-vibrating Fun Factory Share. Keep in mind that not all positions will be enjoyable, that the G-spot curve is quite steep, to the point it can be painful in some angles. You lay down and your partner riding you is the most recommended choice.
  • Fuze Tango — this strapless strapon has few things going for it. You can easily adjust the angle and bulb that goes in the vagina has a friendlier angle. But then it also has a bigger dildo than FunFactory. There are four different color choices and there is space for bullet vibrator insertion too.
fuze tango fun factory share vibe strapless strapon specs

To conclude… it's tricky to get strapless strapon work right. When it works, it's incredible…BUT…

In 90% of cases, you'll be better served with simple strapon dildo and good harness (especially as a beginner pegger).

If you worry about her pleasure then simply get a good bullet vibe or simply do some facesitting to take a break from pegging.

And in the end, pegging is about dominating the partner, changing the roles.

Don't get too stuck up on her pleasure.

Which is why…check out the strapon dildos instead.

With good harness they will work GUARANTEED:


What Is The Best Strapon Dildo?

While this is the most exciting strapon section, it's also the hardest to define the best strapon because everyone likes different things.

Which is why here are four different choices for different purposes.

best strap on dildos reviewed and compared

But know that you can use ANY dildo with a flat base for a strapon.

So yes, all your suction cup, flared base dildos will work… 🙂

And if you don't find anything to your liking here's a huge silicone dildo with suction cup portfolio.

Just always look for body-safe (usually: silicone) materials and you'll be fine.

best strapon dildos specs tantus

Okay, but here's the rundown to explain why each dildo made it to the chart:

  • Tantus Charmer ( For Intermediate )— this is a good medium size strapon dildo with a delicious P-spot angle and ridges. It may be too big for complete beginners but will be perfect for intermediate peggers. While it's not massively huge, it will feel filling due to the ridges. You cannot go wrong with this one. Or alternatively, you can buy Tantus Silk small beginner dildos that were mentioned as the top choice in the harness kit.
  • Vixen Mustang (Most Realistic)—this dildo is for pros who will appreciate the dual density feel and impeccable quality. Dual-density dildos have two layers: a softer outer layer for enhanced comfort and a more solid inner core for functionality. It's mainly made for comfort, but also mimics the feel of a real dick. The rainbow color, the insane realism. It's one of those toys that will make a great long-term investment to your toolbox, but yes, it's pricey. If it's too expensive yet you crave realism, consider this $70 Tantus Cush dual-density dildo as an alternative.
  • Fuze Velvet (Great For Beginners)— Fuze makes great strapon toys and this squishy dildo feels almost like dual-density… It's a perfect toy for beginners to pegging — it's soft enough to be flexible, yet rigid enough to hold the pressure. Finally, those ridges add a unique touch. And yes…there is a place for a bullet vibrator that you can add later.
  • Mr.Hankey's Toys (Extreme Sizes)— okay, this is an honorary mention, because 90% of people are not size-queens or kings. But if you are…then you must check out these guys. They make insane size, insane quality realistic and fantasy dragon dildos. Maybe you cannot fit them yet, but hey — you must have goals right?

Just so you understand what I mean when I say extreme sizes, here's a video of Mr. Hankey's dragon dildos:

And overall their Youtube channel is a must check out if you're considering their bigger toys 😉

mr hankey extreme sex toy youtube channel

In the end, you know best what size you can handle. As long as you avoid the “eyes bigger than hole” dilemma you'll be fine.


What Are The Best Pegging Positions?

best pegging sex positions demonstrated

This depends on your goals:

  • do you want to please yourself while doing it?
  • do you want him to lead, or you want to dominate him?
  • do you want to be able to reach his cock?
  • if you're using strapless strapon — then this will automatically limit many positions, a missionary with her on the bottom works the best.

The best domination position is a doggy style as it exposes butt nicely and rates high in hotness and visuals for the lady.

woman pegging the man anally with strapon toy

Plus, still, he or you can manage to access the cock with some practice.

Missionary still rules. Both ways.

With his legs lifted up, it gives easy access to butt. A precaution though is to protect the balls, that thrusting can easily leave with sore balls 😉

She can lay down and the man can be leading the charge. The same can be done in the doggy position though.

It's recommended to let the receiving end control the speed of insertion initially. With strap on it's impossible to feel how tight, how slidey or dry it is there.

You don't have nerve endings on strapon like a penis has, so you cannot feel what you're doing.

So prepare for a lot of back and forth communication which will lead to a deeper connection than ever.

Here are few more positions from other pegging enthusiasts:


“I like a missionary for the intimacy and the kissing, and the position you mentioned (doggy at the edge of the bed) so she can really pound the life out of me.

I’ve never orgasmed from it but I’ve come really close twice now and both those times were in that position.”

Source: s_e_x_throwaway


“I love putting him on his back not using the full length and sucking his cock at the same time.

The combination of movements drives him crazy.”


“My favorites for pegging my husband are him bent over the bed because I love the view of watching my fake cock sliding in and out.

I also love to grab his hips and really pound him in that position.

Him laying flat on his stomach and me laying on top of him.

This position is very sensual.”

Source: Pegger46


“Bent over the bed, with bonus points for hair pulling.”


woman sharing real pegging story

A Real Pegging Experience Story For Inspiration

Let's conclude with a story from a Reddit forum sharing the sexy details of how a positive pegging experience can look like:


“Just tried pegging my boyfriend for the first time and it went INCREDIBLE.”

“Little background, been with my boyfriend for almost 7 months.

Despite the age gap (I’m 23, he’s 35), the two of us click with an absolutely insatiable sexual chemistry, along with being almost instant best friends.

I know, I know, it’s gross and you want to barf at how stereotypical it sounds.

But it’s kind of new for me. I don’t have the best or healthiest relationship history.

He’s honestly been the best all-around partner I’ve ever had.

We’ve been pretty sexually adventurous from the start, and it didn’t take long for me to suggest switching.

I had started noticing that he had some blatant submissive qualities but he had absolutely no idea that that’s what it was.

It took a little convincing and a lot of wine.

Our first real switch play session brought both of us to our knees, pun intended.

I got to use a hitachi for the first time, he got to have his ass fingered for the first time — it was a good weekend.

About a week afterward, I asked him if he’d ever considered pegging, and the next day we started looking at strapons.

I really did my research and chose what I thought was:

  • a good beginner dildo (and a bigger one, both for me to use on myself now and if he decided he wanted to size up later)
  • a comfortable harness (and in practice, successes on both fronts)
  • as well as water-based lube, because both dildos are silicone.

Last night, I stayed up late doing reading about pegging because I have literally never gotten to this point in a switch relationship.

I’ve dated people who have expressed interest, but the relationship has almost always ended (no connection to the whole pegging thing) before we got to it.

I was fucking nervous.

I really didn’t want to hurt him, or fuck up his psyche, or go too fast …

I was a wreck.

But I did my homework, watched a lot of videos, saw a lot of pictures I didn’t know were allowed on the internet and went to bed feeling less nervous.

Today was the day.

I was ecstatic to be able to play with him like that.

Took my time, warmed him up with a ton of foreplay and oral, bent him over and spanked him, rubbed his shoulders and back, fingered him gently and worked up to a few fingers

… and took the plunge.

It was incredible, and I have to say, I liked it a whole hell of a lot more than I thought I would.

After all, was said and done, he collapsed into my arms and we had a breathless talk about what had just happened, how he felt, where he was at mentally, what he needed from me, and we passed out for a little bit.”

Source: troublecalling


woman kissing a man before pegging sex

Bringing It All Together

I hope after reading this guide you'll make better purchasing decisions.

Remember, that pegging is a new skill and practice makes perfect.

Walk around in these toys, get a feel of them.

Stroke that strapon dildo as you would real dick. It will give you a better feel of the material and you just might have fun with it.

Believe me, you'll feel empowered!

In the end, your choice will depend on your specific needs.

If he's excited about pegging and loves prostate play already, you won't need to convince him of trying new things and going naughty fast.

However, if he's open, yet hesitant the safer and sexier you make the experience the better it will be.

Also, in case you're a lesbian couple, your size preferences will be much different if you play vaginally or anally.

Finally, don't make it all about the strap-on! Make it part of the experience, but it doesn't need to be all of it!

Foreplay and afterplay, can add so much more to it..!

If there are any questions or suggestions left, let them know down below:

Happy pegging!

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