How to do anal sex and anal play

This may seem like a really lame and/or stupid topic, but trust me, if there’s one thing I’ve learned in my adventures as a sex worker, it’s that people are phenomenally uneducated when it comes to sex. I’ll break it down for you guys. Since there are people out there that are way more well-versed in anal than I am, I welcome any additions to this post.

While you don’t need any toys to enjoy playing with your asshole, it does heighten the experience. Different toys offer different experiences, so choose whatever best fits your needs. For instance, stainless steel butt plugs are really heavy, which can feel really good if you’re doing double penetration. They also can be heated up or cooled down for added sensation. On the other hand, you can also use a simple plug or a vibrating plug that stimulates your prostate (if you’re a dude).

Before You Start, Here’s What NOT to Do…

1. Above all: Don’t use anything that doesn’t have a flared base. This is why you see x-rays of people that have a lightbulb, dildo, cucumber, or any other phallic objects inside their rectums. Unless you want to be a joke to the nearest on-call radiologist, use only toys meant specifically for anal play. Your asshole is like a vacuum. Remember that, remind yourself of it daily: “My ass is like a Dyson.”

2. Don’t use the wrong lube with your toys. Using the wrong lube can lead to your dildo collection turning into the liquefied sex toy version of Fukushima. Don’t believe me? If the scientific method is something you’re into, check out this sex blogger’s dildo experiment . Toxic sex toys are serious business! PS – it’s always OK to use more lube.

3. Don’t expect a giant toy to fit right away. If it hurts, stop, take a break, and try something smaller.

4. Don’t go ass-to-mouth or ass-to-pussy without cleaning up first, or use a condom for one hole.
What You Need:

1. Lube. If you’re using toys as part of your anal play, make sure the lube you buy is compatible with the material that your toy’s made of. For instance, don’t use a silicone-based lube on a toy made of silicone. This will damage the toy (remember dildo Fukushima?). Use a water-based lube (like KY) on silicone toys. Some people actually use coconut oil as lube, too. This is a great idea for women that are prone to BV and yeast infections, as coconut oil has natural antifungal and antibacterial properties.

2. Enema. Some people douche with an enema prior to anal sex. This is totally up to you.

3. Baby Wipes. Just trust me.

4. A toy (or fingers, if you prefer)

5. A towel (optional, but I prefer it)

6. Soap and hot water, for cleanup.

The Good Part:

For the sake of my sanity, I’m going to write this assuming there are two people involved and one is on the receiving end. For beginners or people that haven’t done anal play in a while, I highly recommend starting small and working your way up. Instead of using a dildo right away, start with a butt plug.

1. Have everything you need within arm’s reach.

2. Lube up both your asshole and a plug.

3. Take a deep breath and relax. Don’t tense or clench. It won’t work if the person is tense or clenching. If you’re clenching, it’s going to hurt.

4. Very slowly and gently start to insert the toy. It may feel weird or uncomfortable, like you’re pooping, but it’ll get better within a few seconds. Pitchers, pay attention to your partner’s cues.

5. Once the receiving partner gets used to the sensation (it takes a few minutes), start gently playing with the toy or gently applying pressure to the perineum (the taint).

5. Switch out toys if you want and go back to step 4.

(My) Ideal Positions:

1. Spooning. I prefer to control the speed and force with which someone fucks me in the ass, and this position makes it easy. Once I start moving my hips faster, that means it’s ok to go a little harder and faster.

2. Lying face down on the stomach. This is nice for the same reasons, and it allows for more sensation. Especially if you want to try double penetration. I prefer to start with a pillow under my hips, a dildo in my pussy, and then ease into anal sex following the steps listed above. Plus, it’s easy to gradually transition into doggystyle if your partner wants it.

3. Cowgirl. This one is easier once you’re warmed up. The receiving partner has most control with speed and force, unless the person on the bottom thrusts up (don’t do that, it can hurt. A lot).

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