Anal sex entered the mainstream and brought sex toys along for the ride.

According to a 2017 survey, 35% of millennial women (age 22-38) engage in anal sex “at least some of the time.” Women are warming to the pleasures of anal, but it’s not guaranteed.

As the saying goes: “No assholes in the asshole.”

Ladies will only give you the backdoor pass if they think you’ll warm them up and fuck them right. Getting plugged in the keister can be uncomfortable, after all.

Enter the sex toy. A charmed tool that lets you both encourage and deliver amazing anal sex.

The benefits of sex toys during anal sex are threefold:

  • Prepare your partner by stretching her anus
  • Stimulate her vagina or clitoris while fucking her ass
  • Double penetrate her because its fun

Sex toys help you to ensure that your partner’s first time with anal sex is a great time. If you make the experience both comfortable and orgasmic, you’ll be free to access her taboo-ty hole anytime you like.

1. Your Fingers

Nothing feels better than skin on skin. Your fingers are the softest, most agile, and most responsive sex toy at your disposal.

Fingers allow you to:

  • Stretch the anus before penile penetration
  • Stimulate the clitoris and vagina to bring about orgasm

The index finger is the go-to for anal foreplay. Inserting a digit lets you stretch the anal sphincter, or the opening to anal cavity, at a controlled pace.

To begin, apply a liberal amount of water-based lubricant to your finger.

And before you begin to probe your partner’s ass, massage her brown button. Swirling a finger around her butthole will help to relax both her body and her mind.

Insert your finger slowly because “there can be too much friction with that in-and-out sensation because the anus is squeezing and increasing the pressure. That friction can be uncomfortable, even when there’s plenty of lubricant,” says Charlie Glickman, a trained sex coach.

The slower you go, the less friction and discomfort there will be. Once you’ve breached the butthole, pause and check in with your partner. If she’s okay, push in toward the first knuckle. Pull out a bit, then push inward again, maybe up to the second or third knuckle.

Your angle of entry is important. Pressing upward, downward, or to one side can scrape the anal lining and cause pain. Aim to go straight in.

Using the Fingers for Clitoral and Vaginal Stimulation During Anal Sex

Once your cock is in her tush, you can use your free hands to stimulate her clitoris and vagina.

Fact is, most women need clitoral stimulation to reach vaginal orgasm. Anal orgasms are also real, so aspire to giving your partner either or both.

If you’re in doggy style, rotate your wrist like you’re holding a tennis racquet. Then plug your forefingers into her vagina and bring your thumb to her clitoris. Now you can apply pressure to the G-spot with your forefingers as you work your thumb over the clit.

As you thrust in and pull outward, vary the pressure and movement across the G-spot and the clitoris. Your partner may prefer you to brush her clit lightly, or to really finger her G-spot. Ask what feels best.

Try to synchronize your hips with your handiwork in a way that will bring on the fireworks.

Visit School of Squirt for more information on anal fingering.

2. Butt Plugs

The nerve endings in the anus are located in the sphincter, not the anal cavity. This means that all pleasure and pain originates from the area of entry, or “just the tip.”

Butt plugs are great for beginners because the tapered shape allows for easy insertion and minimal discomfort.

Finding the right size is key. Fortunately, a butt plug kit lets your woman start small and graduate to a larger size.

“To prepare a bottom for sex play, start with fingers, tongue, or a very small sex toy designed for butt play,” says clinical sexologist Dr. Nancy Sutton Pierce. “An option is to purchase a butt plug kit that uses several plugs, of graduating sizes, just for this training.”

The weighted sensation of a butt plug in the anus is quite pleasurable. If used during vaginal intercourse, the butt plug will feel like a warm magnet in your partner’s rectum that follows your cock as it moves.

To further enhance her sensations, glass butt plugs can be heated in the microwave or cooled in the refrigerator. You can also buy a vibrating butt plug to spark new levels of enjoyment.

Don’t be surprised if your lady wants to rock her plug in the office for some all-day naughty excitement.

3. The Vibrating Dildo

The vibrating dildo is a versatile tool.

When you’re starting out, a vibrator is a great for buttplay. “Simply place the head against the anal opening but don’t insert. Glide the toy in a circle around the opening. External anal vibrations add completely new sensations. Alternate between the vibe and your finger to really tease,” says sexologist Dr. Jill McDevitt.

Once your partners is comfortable with anal intercourse, a penis-shaped vibrator can be used for double penetration. Filling her pussy and her ass simultaneously – choose your hole – will make her feel intimate, sexy, and dirty all once.

Since the tissue between the vagina and the rectum is so thin, anal penetration can stimulate the front wall of the vagina, also known as the G-spot. Turning the vibrator to her vagina and clitoris will also help her climax.

“Bunny” vibrators are ideal for granting an orgasm. Seen below, the vibrating shaft curves upward to rev her G-spot while the “ears” at front gently activate the clitoris.

Remember that anal sex isn’t just doggy style. If your woman lays on her side, you’ll have easier access to both her vagina and her clit. Reacharounds are tough, you know?

5. Anal Beads

The pleasure of anal sex comes from pulling out rather than pushing inward.

This is why anal beads are such a dynamite sex toy. You insert the beads into your partner’s ass, then withdraw them as your partner nears climax. This will 10x her orgasm by making the sensations radiate throughout her entire body.

“But do this slowly,” says Sammi Cole of Lovehoney sex toys. “You aren’t starting a lawnmower.”

Anal beads come in all sizes, so they’re also well-suited to anal play. Grab a set of graduated anal beads and use them to dilate your partner’s butt prior to sex. Seen below, this sex toy starts very small and then gets to about an inch in diameter.

Ultimately, your choice of sex toy will depend on your partner’s comfort level, your shared familiarity, and how kinky you feel together.


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