• Darkside Magazine

The Ins and Outs of Anal Sex

The very lovely Jessica Savage – the 'Kink' in website Kinkandthekitty.com – gives us the lowdown on playing safely when entering the back door...




I am an anal enthusiast. I was fortunate enough to be introduced to it by an experienced booty lover. I was the ripe age of 18 and dating a wonderfully kinky, older couple. As we were conversing, it came up that I was a virgin when it came to my backdoor. It took a moderate amount of convincing, but with his busty wife on my left and a sultry playmate on my right, I succumbed to the curiosity.

“With a lot of lube and even more patience, he penetrated my rectal rose. And to my surprise and delight, it felt amazing!”

He firmly grabbed my ass and pulled it off the couch. Our lovely ass-istants gently held my legs back. One sucked on my nipples, and the other stimulated my clit as he knelt in front of me at an optimal anal height. With a lot of lube and even more patience, he penetrated my rectal rose. And to both my surprise and delight, it felt amazing and eventually, I squirt all over him!


My experience was obviously not ordinary for most players. I'm excited to share this article because most of the inquiries I receive are for anal advice. I also know several people who refuse to engage because their first time was a painful tragedy. In this article, I'm going to tell you what to expect and how to do it and also give you toy and lube recommendations, butt first, Im going to provide you with an anatomy lesson because part of proper preparation is education.


1. Know Your Anatomy

When it comes to butts, we're all the same. The anus is the short tube located at the end of the rectum and is surrounded by two sets of muscles known as the internal and external sphincters. The external sphincter can move voluntarily while the internal sphincter typically cannot. These two muscle groups hold the anus open and closed and contain numerous nerve endings that will give you essential information about whether what you are experiencing is painful or pleasurable. The anus is one of the most sensitive areas of the entire body. Interconnected with these muscles are the pubococcygeus or PC muscles that help form the pelvic floor, and contract during an orgasm. The anus does not expand from arousal, like a vagina, but it can stretch, so it is essential to train, warm-up, and go slow with penetration to avoid tears.


The rectum is located behind the anus at the end of the digestive tract and is typically 4-6 inches long. This chamber holds feces before evacuation but usually is free of more significant amounts of fecal matter. When it comes to anal play, the difference between males and females is access to the prostate through the rectal walls. The prostate gland is a walnut-sized gland located between the bladder and the penis and is often called the male G-Spot.


2. Use Lube

I cannot stress the importance of good lube enough. Because the lining of the anus is so thin, lube will help avoid any tears. Apply a decent amount and expect to reapply. When looking for an anal lube, I prefer something silicone, especially if using a condom. Oil can erode latex, causing condoms to break. But remember not to use your silicone lube on silicone toys. There are also water based lubes out there, but they aren't the best for anal as they dry out quickly and can be absorbed into the body. You want something with a slip that isn't sticky and made for longevity.


3. No Numbing Creams or Numbing Lubes

Never use numbing cream during anal. It's crucial to feel when things are getting painful. Numbing lube will increase the likelihood of tearing and complications.


4. Self Exploration

One of the best ways to prepare for anal sex is to explore your ass yourself! It's necessary to understand your own body and what feels pleasurable to you and will help you relax when playing with a partner by knowing what to expect. Before making love to your bud, trim your nails, and clean under them. The shower is a great place to start. Using body wash, try rubbing the outside, pressing on it, and even pushing in a finger or two. Find out what feels good to you.


5. Training

When you're feeling a little braver, introduce toys. Anal beads are one of the best because they slowly increase in diameter. My favorite anal toy is a beaded glass dildo like this one, but you can also get strings that start at a smaller dimension, like this. Remember to always pull them out sloooooowly. In addition to beads, plugs are a great way to begin training. Anal training kits are available with multiple sizes of plugs and can be worn for extended periods.


6. Shit Happens

Just like period sex, a little poop isn't something to make into a big deal. If you are worried about getting shit on your dick, then you shouldn't be having anal sex. Anal is a whole lot of fun, so try to get over it, and if you just can't, then it's alright to abstain too. Put a towel down ahead of time and be prepared to have a little clean-up after. There is no reason for either party to be embarrassed. You may feel like you need to shit, but you probably won't. You can penetrate 5-7 inches before reaching the sigmoid colon, where your waste is stored.


7. You May Bleed a Little

Even with training, warming up, a slow pace and good lube, you may still experience some small tears in the anal lining. A small amount is normal and shouldn't cause concern. If it is painful and you are bleeding a lot, medical attention may be needed.


8. Enema

There are ways to avoid a potentially messy situation ahead of time. But remember that unless you need to evacuate your bowels, your rectum is mostly free of shit. If you're thinking, "But when I douche, lots of poop comes out!" That is because when you force fluid into the anus, it pushes past the rectum into the sigmoid colon. But, If you still feel the need, or want to incorporate it into your BDSM play, use an enema bulb, with water only and use light pressure. You dont need to force all of the water into your anus. As one article said, "you only need to clean a few inches, not your entire gut."


9. Clean Your Body

For most of us, there is hair located around the anus. Rimming is most pleasurable for me when the person has groomed their hair. If you decide to leave it give it a good cleaning and make sure there is no fecal matter hanging on. Use a washcloth with soap and warm water to clean between the wrinkles of the anus and use your finger to clean just inside.


10. Ask Permission

As with everything, consent is king. NEVER try to force your cock in someone's asshole without asking for their permission first!


11. Use Condoms

I'm blown away by the younger generations' desire to ditch the condoms, but unless you're fluid bonded with a primary partner, wrap it up! The possibility of anal tears can increase the likelihood of STDs/STIs like HIV and HPV.


12. Warm Up

You've explored on your own; now it's time to introduce a partner! Pull out your high-quality lube and start with activities like rimming and fingering and move on to toys. It's important to gently stretch your starfish in preparation for penetration.


13. Position

The best positions for anal are on the stomach, doggy, and missionary, and for most people, that is the order of least to most painful. I also enjoy being on top, because it puts me in full control, though gravity can have an impact on your ability to go slow. My favorite position for anal is on my back with my legs up. It allows me the best positioning for clitoral stimulation, is the most likely to make me orgasm or squirt, and my partner can see my face and hands making my body language more readable.


14. Stimulation

It can help increase pleasure and relaxation to arouse other parts of your body during anal sex. I prefer to stimulate myself, rather than have my partner do it because I know exactly what feels good during the first crucial moments of anal sex.


15. Breathe and Relax

You can practice ahead of time by closing your eyes and clenching your sphincter, tightening it then relaxing it. Breathe into it, focus, and try to relax more. Or as they say in meditations "sink deeper." This is so important when experiencing penetration. The more you relax and breathe, the easier it will be for your body to accept a cock!


16. Go Slow!

No matter the power dynamic, when it comes to anal, the bottom is always in control. Bottoms, be verbal! You need to let your top know when to stop and when you are ready for more. My top always allows me to be in control, and as a result, I love anal with Him. If you aren't verbal, you can use your hand as a signal - up for stop, down for more. When I have Him stop, I take a moment to breathe and relax before I take more. The first few inches are the anus and are the most difficult to get through. In addition, the head is the largest part of the penis, so once it passes into the rectum, you are pretty much good to go! If my lining tears or is scratched by nail, its almost impossible for me to continue that day.


17. Enjoy!

This should be fun! Part of enjoying it physically is enjoying it mentally. Get turned on by it. Don't just do it for your partner, do it for you. Forget the taboos and plow forward.


I hope this article inspires you to give anal a try or even become good little butt sluts! Anal sex can be incredibly pleasurable, but if for whatever reason you decide its not for you, that's ok too. Even though I love it, some nights I'm just not in the mood, or my brain is but my body isn't. Listen to yourself.


Your Kinky Kitty,


Jessica RAVAGE



288 views
Subscribe to our mailing list and keep up to date with Darkside!
  • YouTube
  • Black Facebook Icon
  • Black Instagram Icon
  • Black Pinterest Icon
  • Black Twitter Icon
  • Black Facebook Icon
  • Black Instagram Icon
  • Black Pinterest Icon
  • Black Twitter Icon