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Best Pegging Toys for Beginners | First Timer Pegging Toy Buyers Guide

Best Pegging Toys for Beginners | First Timer Pegging Toy Buyers Guide

Last Updated on March 18, 2021

Shopping for the best pegging toys online for the first time is an adventure of its own. Technically, there is no such thing as a sex shop category solely called “toys for pegging” rather, they are a collection of thin dildos, suction cup vibrators, small butt plugs, slender anal probes, dildo, tiny prostate toys and curved anal sex toys.

Now combine this basket full of sex toys and figure out which ones are compatible with a strap on harness, and now you have a pegging sex toys kit. Confused? If you're not well versed in the sexual satisfaction industry like we are, then yes, buying the best beginner pegging toys can be confusing for couples who are searching for information for the first time.

Beginners take note, I've created this online buyers guide to help you select a great combination of items for the first time that will fulfill this new kinky woman on man anal sex fantasy. If you want a definition before you begin, make sure to know what does pegging sex mean. Learn full details and some tips on potions and suggestions for couples to make the experience more enjoyable.

There are 2 Subcategories of Pegging Toys:

  1. Strap On for Pegging
  2. Pegging Dildo

It's simple math, 1+2 = 3. Combine a strap on with a dildo and you made a pegging sex toy. Pegging sex is the act of anal penetration of a man by a woman wearing a strap on dildo harness. It was previously known as role reversal. If she does not wear a strap on, then she is not pegging him. Otherwise, it's just prostate stimulation or anal foreplay for him.

Best Pegging Sex Toy Kits

The easiest (and most popular) way for couples to bring this trend into their bedroom is to purchase a pegging kit. These best selling strap-on dildos include both the harness and the attachment. These are specialized kits made specifically for beginners. The greatest appeal is that the harnesses are beautiful with feminine styling and a custom fit for the included attachment.


Panty Pegging Strap on Kit

Panty Pegging Strap on Kit

Our most luxurious strapon! Panty Pegging Strap on Kit features a lace overlay red satin panty harness with scalloped detailed back and sewn in rubber O ring to support the dildo. Double layers of polyester pad the space between the round base and your skin to make sure your comfort is maintained at all times.

It looks good too, damn good! Capture your inner domina with this stellar collection. Available in both small and size options, regardless of the panty size selected, the silicone dildo size that comes with it is the same.


Sex Mischief Pegging Kit

Sex & Mischief Pegging Kit

Sex & Mischief Pegging Kit includes a pretty little probe with a slight forward curve that naturally touches his prostate. Prostate massage and pegging toys go hand in hand. If you can stimulate his P-Spot in the midst of sex then he'll certainly be back for more.

Beautiful swirled pure silicone dildo is one of the nicest looking probes we have for sale. Simple yet high quality strapon adjusts around the legs and at the hips to assure a great fit, this one easily fits plus size gals; the maximum waist size is 60 inches.


Pegged Harness Kit

Pegged Harness Kit

Our most budget friendly option, Pegged Harness Kit offers excellent value for the dollar. Nicely stitched and finished harness with a shiny PVC front to give it a slight kinky appeal and a dominatrix style look. Body safe, non toxic and non-porous silicone dildo is 5 inches long and barely bigger than his finger. It's a great introductory choice for first timers.

This is the perfect kit for him & her because it saves you the step of shopping for an attachment separately by including a pure silicone dildo for him. Pure silicone is a real selling feature because it's easy to sterilize and hypoallergenic.

The top third curves slight upwards to encourage the shaft to make contact with his prostate gland upon penetration. The mere 7/8 inch width is not intimidating to him, but be sure to add thick butt lube to make that first insertion smooth.


A Few Tips for Him & Her

This trend is already evolving. It is now becoming a little more relaxed as now a woman does not need to wear a strap on, she can simply insert the device into her partner's butt by hand and stimulate the sensitive nerve endings. The definition is evolving a bit as time goes on.

Most partners who shop stick to the original concept and purchase both components: The pegging dildo or vibrator and a separate dildo harness for the attachment.

Before jumping in, review my guide on preparing for anal sex because these plugs & dildos are ideally sized for anal training. You don't necessarily need your lover to be present, you can try these alone during masturbation to get used to the feel of anal penetration. In fact, I recommend you try it yourself first just to be in control of the depth, angle and speed of penetration. The butt cherry is a delicate thing!

10 Best Pegging Toys for Beginners

 
Mini Curved

1. Mini Curved Dildo

This is the quintessential pegging dildo for beginners. Mini Curved does everything right, and nothing wrong. The tiny realistic dildo has a steep curve perfect for pinpoint prostate stimulation and the extra wide base will fit in any size harness ring.

The shaft can bend slightly, but remains stiff enough for anal insertion. The mini size won't scare him and make him pucker up either, this is the smallest of all anal sex appropriate dildos. This is my top rated realistic dildo for pegging first timers.

  • Natural curve made for prostate stimulation
  • Wide base fits into any strap on ring
  • The smallest realistic pegging toy
  • 5 inches long, 3 1/2 inches insertable
 
Temptasia

2. Temptasia

The best pegging toy for first timers because it's less than 1 inch wide, but long enough so he can actually feel it in his butt. Temptasia is a super stylish flexible probe with a heart shaped base that looks feminine yet naughty when fixed to the harness that she wears.

This is a must-have accessory, the pure silicone feels like silk and is non-porous so it's easy to sanitize after use with antibacterial soap or sex toy cleaner. The shaft can bend at any point so as it slides in his butthole it never pokes in a place that won't feel good. It follows the curves and passageways of his rectum and feels great!

  • Seamless smooth probe for easy penetration
  • Heart shaped base has a feminine touch of class
  • The smallest silicone pegging toy
  • 4 1/2 inches long, 3/4 inch across
 
Mini Whopper Anal Dildo

3. Mini Whopper Anal Dildo

Mini Whopper Anal Dildo is the smallest pegging toy with a steady 1 inch length that remains the same from tip to end. The top is shaped like a tiny penis head with a gentle rounded end that pops in easily when well lubricated.

The shaft can bend, but it's not too floppy. If you use a device that is too soft then it will crimp and bend sideways when you insert it. Remember that pressure is needed to ease it into his anus, so a stiffer toy makes it easier.

  • The smallest rubber attachment
  • 5 3/4 inches long, 1 inch diameter
  • Available in white or brown skin tones
  • Large suction cup base fits any O-ring size
 
Booty Teaser

4. Booty Teaser

Although this is a small butt plug, the Booty Teaser makes the best pegging toy for beginners. The thin silicone shaft has a rounded end and thin neck to add a massaging feel to his sphincter while his partner thrusts.

The comfortable thinner neck can bend easily and the silky feeling luxurious silicone surface is a nice quality upgrade compared to the typical rubber anal plug. The anchor shaped base grabs onto the strap on ring and stays in place.

  • Anchor shaped base for external teasing
  • Pure silicone
  • 4 inches long
  • Less than 1 inch diameter
 
Slim Suction Penis

5. Slim Suction Penis

The longest beginner pegging sex toy for sale, the ribbed realistic Slim Suction Penis is also the most popular selection for first timers, but many partners may not realize the flared base fits through a small strap on harness ring.

The slender elongated shaft is floppy, so you'll need 2 hands to insert it into his butt, but once inside he can dictate how deep you should go. The diameter may be a tad wide for a first timer, but if he likes the feel of prostate plugs or anal probes, he'll truly enjoy this ribbed wonder.

  • The longest toy for pegging
  • 2 sizes available
  • Flexible rubber shaft
  • Rounded head for easy insertion
 
4 Inch Whopper

6. 4 Inch Vibrating Whopper

Pegging vibrators are few and far between, but we've hand picked the little 4 Inch Vibrating Whopper, which was originally made for women to be used by partners as a vibrating pegging toy instead. The realistic penis shaped shaft has a stuff enough build to insert far into his ass, yet the shaft is bendable enough to move with your bodies as you change positions.

The intense, super powerful vibration has enough strength to fire his ejaculation across the room, it greatly improves his orgasm, and is a must have small vibrator for couples who like intense couples adult toys.

  • Most powerful vibrating pegging toy
  • Steady stovepipe shaft
  • 4 ¾ inches insertable
  • Available in beige or brown
 
Mr. Skin Mini Dildo

7. Mr. Skin Mini Dildo

The flat circular base stays put in your strap on ring, and the thin head that gradually increases in girth along the shaft offers him a nice, cushy stretch. He can tell you how to deep to go depending on how much he's enjoying the increasing diameter. The small penis head is 1 inch wide and the shaft increases to 1 1/4 inches near the base of the shaft (before the suction cup begins).

Mr. Skin Mini Dildo is made of smooth silky skin like rubber that inserts really comfortably and the curved shaft is flexible so you can move around without poking his rectum. It's the perfect shape with a comfortable texture to make him a happy guy.

  • Silky smoith rubber surface
  • Graduated shaft adds pleasure
  • Flared base fits any strap on ring
  • Available in 3 colors
 
BFF Petite

8. BFF Petite Dildo

We love this shape, it's the quintessential smooth unisex and non-binary anal toy that goes super deep with all the flex to keep it cozy. BFF Petite may be too thick for someone who's never inserted an anal probe before, but if your man has used butt plugs during masturbation or sex in the past, this one shouldn't be too far of an upgrade for him.

The shape is excellent for guys who think pegging is gay, the non-phallic shape won't make him feel strange during sex and the slight upwards curve is ergonomic when you're enjoying strap on anal sex. The cheap price can't be beat either!

  • Non-phallic shape is the most discreet
  • Cheap price
  • Natural curve reaches the prostate
  • Popular size upgrade for men
 
Naughty Plug

9. Naughty Plug

There are 2 sizes of Naughty Plug, so many lovers purchase both and use the small one first then upgrade to the large plug once he's used to the sensation. Using a dildo like this is is also known as “anal training”. It has the standard plug shape, but if you know the purpose of a butt plug you'll understand it's application for this type of sex play.

The anchor base is harness compatible and the thick forward curved tip massages the prostate instantly upon insertion. It's the easiest butt plug to locate the prostate and even though some have thinner tips, the flared end here has larger space to cover inside the body, therefore ensuring the prostate will be touched!

  • Made for the male prostate
  • Comes in 2 sizes for training
  • Wide tip massages deep
  • Premium silicone
 
Anal Training Kit

10. Anal Training Kit

This is a collection that includes all 3 of the dildo butt plugs as shown. All 3 of these are harness compatible, husbands and wives love to use the Anal Training Kit as pegging toys because they shaft are longer, longer toys are easier to use during pegging strap on anal sex.

The jelly soft rubber is super bendable so you can give him a good ramming from behind and it won't hurt his anus. This is a secret accessory that lovers swear by, the size range between small to large is quite vast so this collection is all a couple needs. We think it should take a top spot in your list too.

  • Kit includes 3 harness compatible butt plugs
  • Each toy has a different size & shape
  • Soft & malleable rubber for comfort
  • Available in 3 colors
 

Best Harness For Your Pegging Toy

The Innovation

The Innovation is the best strap on for beginners because it has a high quality luxurious streamlined design at a cheap price to support silicone dildos. Sure we've seen cheaper harnesses for sale, but this one is actually nice and super comfortable for her to wear.

It has a cloth lining and hemmed in ring that has better feminine styling. It can be dressed up a naughty or nice, this is our most versatile harness option and the newest pegging strap on. The thong style back looks ultra sexy and the whole thing can be hand washed.

  • Soft fabric harness
  • Sexy G-string style back
  • Stretchy rubber O-ring sewn into the fabric
  • Fits up to a 50 inch waist
 
TITLE

SX harness is our favorite budget option that is durable and well made. The silky soft straps won't chafe, the imitation leather harness backing has a dark and demure appearance similar to what a dominatrix would wear kin the bedroom. Perfect for acting up your erotic sex fantasy! There is even room up front for her to use a bullet vibe.

Includes 2 rubber O rings allowing more variance in attachment sizes compared to the first option, however most couples who peg choose thin and small attachments so having a large O ring is not an important feature, but versatility is always nice; you never know what the future holds!

  • Most inexpensive option
  • Made to fit small pegging toys
  • Imitation leather harness
  • Fits up to a 48 inch waist
 
Lux Fetish Strap On

Lux Fetish Strap On is a beautiful strap on for women with a velvety fleecy looking lining that comes available in either hot pink or jet black. Long nylon straps adjust in 4 points on the body.

The straps can be extended far longer than any other option easily fitting a XXL size gal. A pouch in the top has enough space to slide a bullet vibrator for extra vibration during play. Low rise is one of the most visually appealing, gals who wear this certainly feel like a sex goddess!

  • Pouch sewn in the top so the wearer can insert her vibrator
  • Velvety harness looks great
  • Includes a removable rubber O ring
  • Fits extra large sizes up to XXL (65 inch waist)
 

More Good Anal Pegging Toys for Beginners:

The following butt toys include small dildos that are well suited for anal insertion. If you wonder what the actual size looks like in relation to the body, these demonstration will give you an accurate idea of what they look like upon entry.

The best pegging toys for men also include the possibility of a dildo that is originally intended for women, but in our experience, they are perfectly suited for guys who want to try backdoor penetration for the first time. Make sure to keep your options open when shopping online for pegging accessories!

All of these dildo and butt plugs can be worn on a strap on harness for first time pegging, but as seen in the video demonstrations, they can be used alone during male masturbation. In fact, it's one of the best ways for guys to get used to the feeling of anal.

Guys go at the pace they choose and as deep or as shallow as they decide. Invite her into the room after you've given yourself a nice introductory lesson on the first timer pegging toys you like best. Before you shop online, make sure to check out the following suggestions that beginners like most:

 
beginner butt plug

Beginner & Intermediate Butt Plug

I think the ordinary, classic shaped butt plug makes the perfect pegging toy for beginners. The flat base always stays inside the harness O-ring and will never slip out. They are stiff enough to insert without too much fumbling, which makes the entire experience easy and fast. Start with the Small size and then introduce him to the Medium size once his rectum has been stretched enough. (Each size option is sold separately.)

 
Mood Blue

Mood Blue

A pegging toy you'll only see here! Why? Normally sold as an anal sex toy only, I've modified it's designated category and moved Mood Blue into my list of best pegging toys for men. It just happens to have the right curve for prostate stimulation and the anchor shaped curved base is permanently held snug in the strap on ring (until you remove thew harness and slide it out from the ring, of course!)

 
jellie anal kit

Jellie Anal Trainer Kit

The perfect pack of soft ribbed anal dildos for those who want to teach the butthole to stretch. Jellie Anal Trainers are super soft with graduated bumps, they squish into the anus oh-so delightfully. The size difference between the small and large is just enough to take that one step further into male anal stretching. The high quality jelly won't leave a tacky mess when mixed with thick anal lube either.

 
anal starter

Anal Starter

Shaped like a small penis with more flexibility than an average anal dildo, Anal Starter is a fine dildo for him, but one thing must be taken into consideration before attaching it to your stapon: The base is flared, but only slightly. It will fall out of an ordinary ring, so take a trip to a hardware store and buy a smaller rubber O ring to snap onto your harness. Then the dildo will fit without an issue. Since it's so soft, you might need a little maneuvering for initial entry, as demonstrated in the video.

 

Conclude with Pegging Sex Toys Lube

As a final note before we conclude, butt lube is an important add-on that improves pleasure and makes the dildo penetration experience more enjoyable. Which one to buy? Thick water based anal sex lube is the best pegging lube.

A viscous gel is less runny that a vaginal lube, and the water based style cleans easily. Make sure to select water based lube only because if you have a silicone pegging toy, silicone lube will melt the surface over time. Add one of the lubricant applicators to reduce mess and make sure the lube doesn't spill out of his anus.

When it comes to anal penetration from any combination of anal toys, lubricant is absolutely the most important aspect to consider. The anus does not lubricate itself like the vagina does and when the partner tries to squeeze a dildo into the tight anus sphincter, it can cause serious discomfort, even tearing the tissue.

The solution to preventing this is to properly use lube. It's such a hot topic that I've even created a completely dedicated blog entry talking about the importance of personal lube and sharing ways to apply it to make anal not hurt. The last thing you want to do is get off on a painful start, especially when partners are involved because we want this new experience to be a good one!



Click to buy pegging dildos & strap ons online.



Mayla Green

Mayla Green has been involved in the sex toy industry since 2004. Working behind the motto “Sex TOYS should be FUN”, Mayla provides unique tips & advice amassed from over a decade of hands on experience with adult products. She also coaches clients how to fully enjoy sexual pleasure and can be seen in major publications & magazines online.

Happily married since 2009, she knows firsthand how the sex life eventually becomes repetitive (which truthfully means boring), so if you're looking to spice things up in the bedroom, Mayla's your gal! Her literary pride & joy is covering topics for established couples needing inspiration to keep lovemaking exciting and fun.

Not in a relationship? Her other focus is teaching women how to properly handle the “little person in the canoe” to experience the best orgasms ever, no partner required! Her creative and innovative tips, techniques and advice is on par with a certified sex therapist or Sexologist, but with an extra advantage from her knowledge of the adult toy business.

View all articles published by Mayla Green exclusively for The Adult Toy Shop sex blog. Mayla Green's Linkedin profile highlights her professional background, experience and training.

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