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Bettys Toy Box is a women-owned, family run sex-positive boutique where pleasure meets confidence, offering body-safe toys, real advice, and a playful space to explore what feels good.

Pegging Sets (Harness + Dildo) for Amazing Anal Sex

Does your partner beg to be pegged? Try one of these dildo and harness sets, ready made to introduce both of you to the wonders of anal sex and pegging. Take the guess work out of matching a strap on harness to a dildo with these easy to use, high quality pegging sets. If you're new to pegging and looking for more information to get started Betty suggests checking out A Beginner's Guide to Pegging on the Betty's Buzz blog or Pegging 101 with Tawney, an informative video guide.

  • Our First Hollow Strap-On Dildo + Harness Set - Chocolate

    Original price $21.00 - Original price $21.00
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    $21.00 - $21.00
    Current price $21.00
    In stock

    Explore new pleasures together with Our First Hollow Strap-On Dildo + Harness Set in a rich chocolate tone. Designed for beginners, couples, or men...

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    Original price $21.00 - Original price $21.00
    Original price
    $21.00
    $21.00 - $21.00
    Current price $21.00
  • Our First Hollow Strap-On Dildo + Harness Set - Vanilla

    Original price $21.00 - Original price $21.00
    Original price
    $21.00
    $21.00 - $21.00
    Current price $21.00
    In stock

    Discover new ways to play and stay in the moment with Our First Hollow Strap-On Dildo + Harness Set in a soft vanilla tone. Designed for beginners ...

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    Original price $21.00 - Original price $21.00
    Original price
    $21.00
    $21.00 - $21.00
    Current price $21.00
  • Bend Over Beginner 2 Dildos + Vibrating Strap-on Harness - Purple

    Original price $93.99 - Original price $93.99
    Original price
    $93.99
    $93.99 - $93.99
    Current price $93.99
    In stock

    Betty's bestselling starter kit for anybody wanting to explore pegging or strap-on play. The kit includes an adjustable, machine-washable harness,...

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    Original price $93.99 - Original price $93.99
    Original price
    $93.99
    $93.99 - $93.99
    Current price $93.99
  • Trio Deluxe Advanced Anal Training Kit with 3 Realistic Dildos - Vanilla

    Original price $46.99
    Original price $46.99 - Original price $46.99
    Original price $46.99
    Current price $39.00
    $39.00 - $39.00
    Current price $39.00
    In stock

    This Trio brings a sexy realistic look to a more advanced anal trainer set. Perfect for anybody who loves anal and wants to stretch their boundarie...

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    Original price $46.99
    Original price $46.99 - Original price $46.99
    Original price $46.99
    Current price $39.00
    $39.00 - $39.00
    Current price $39.00
    Save 17% Save %
  • Bend Over Beginner 2 Dildos + Vibrating Strap-on Harness - Black

    Original price $93.99 - Original price $93.99
    Original price
    $93.99
    $93.99 - $93.99
    Current price $93.99
    In stock

    Betty's bestselling starter kit for anybody wanting to explore pegging or strap-on play. The kit includes an adjustable, machine-washable harness, ...

    View full details
    Original price $93.99 - Original price $93.99
    Original price
    $93.99
    $93.99 - $93.99
    Current price $93.99
  • Romp Piccolo First Time Pegging Kit - Strap on Harness + Dildo

    Original price $34.99 - Original price $34.99
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    $34.99
    $34.99 - $34.99
    Current price $34.99
    In stock

    Colorful and so easy to use, the Romp Piccolo kit includes the sleek and silky silicone Piccolo dildo and a comfortable and adjustable strap-on har...

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    Original price $34.99 - Original price $34.99
    Original price
    $34.99
    $34.99 - $34.99
    Current price $34.99
  • New Comer's Strap-on Harness & Dildo Set

    Original price $46.99 - Original price $46.99
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    $46.99
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    Current price $46.99
    In stock

    Whether you're exploring anal or vaginal strap on play, this is a perfect kit for a beginner to penetration. The slender silicone dildo is a great ...

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    Original price $46.99 - Original price $46.99
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    $46.99
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    Current price $46.99
  • Body Dock Two Dildos + Harness Fantasy Strap-on Kit

    Original price $129.99 - Original price $129.99
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    Current price $129.99
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    This is the ultimate fast and simple harness system with two beautiful silicone dildos and the easiest strap-on harness you will ever use.  This un...

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    Original price $129.99 - Original price $129.99
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    $129.99
    $129.99 - $129.99
    Current price $129.99
  • Pop Strap on Dildo & Harness Set in Pink Silicone - 5 inches

    Original price $69.00 - Original price $69.00
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    $69.00 - $69.00
    Current price $69.00
    Low stock

    Come together and play with this fun small strap on dildo set in a bright pink silicone. You're going to love the comfortable harness that includes...

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    Original price $69.00 - Original price $69.00
    Original price
    $69.00
    $69.00 - $69.00
    Current price $69.00

Frequently Asked Questions About Strap-on Play

What is a strap-on?

A strap-on is a wearable setup that typically includes a harness and a dildo. The harness is worn on the body and holds the toy in place for penetrative play. Strap-ons can be used by people of all genders and are available in a variety of styles, fits, and sizes.

How do I choose the right strap-on harness?

The right harness comes down to comfort, fit, and the kind of experience you want. Adjustable waist-and-thigh harnesses are a great place to start because they offer stability and control. Underwear-style harnesses are soft and easy to wear, while thigh harnesses provide alternative positioning options.

Are strap-ons beginner-friendly?

Yes, absolutely. Many strap-ons are designed with beginners in mind. Starting with an adjustable harness and a smaller, body-safe dildo can make the experience feel more comfortable and less overwhelming.

How should a strap-on harness fit?

A harness should feel snug and secure without pinching or restricting movement. The toy should sit firmly against your body with minimal shifting. A good fit makes everything feel more natural and easier to control.

Can any dildo be used with a strap-on harness?

Not all dildos are compatible. Most harnesses are designed to work with dildos that have a flared base, which helps keep the toy secure. It’s always a good idea to check compatibility before choosing your setup.

What size strap-on dildo should I start with?

If you’re new, starting with a smaller or medium-sized dildo is usually the most comfortable option. It’s easier to control and can help both partners ease into the experience. You can always explore larger sizes later.

Are strap-ons only for certain genders or couples?

Not at all. Strap-ons are for anyone—regardless of gender, body type, or relationship style. They can be used for pleasure, exploration, connection, and gender affirmation.

Do I need lubricant when using a strap-on?

Yes, lubricant makes a big difference in comfort and ease. Water-based lubricant is a great all-around option and works well with most toys. Using enough lube helps reduce friction and enhances the experience.

How do I use a strap-on comfortably?

Start with a well-fitted harness, a compatible toy, and plenty of lubricant. Take your time, go slowly, and communicate with your partner. Practicing on your own first can also help you feel more confident.

How do I clean a strap-on harness and dildo?

Clean your toy before and after use with warm water and a gentle cleaner. Silicone toys are non-porous and easy to maintain. Harness care depends on the material, so check the care instructions. Always let everything dry fully before storing.