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Each week, CASSIUS’ resident expert answers sex-related quarantine questions and needs and make sure you don’t get too bored. This week she replies to a letter from a man who wants to know how to make anal sex pleasurable for his girl’s first time.


Hey Tyomi,

My girl and I have been talking about having anal sex for a while, and she’s into it, but a little nervous. She’s concerned that she will sh*t on me (which I don’t mind actually) and that I’m going to hurt her since I’m so big (9-inch d*ck and proud damnit!). How can I help her feel more comfortable about attempting, and what steps do we need to take to make this process easy and feel good?

Signed “Eager and Ready”

Hey Eager and Ready,

The anus has been designed biologically for things to come out of it, not go inside of it, so when you’re having anal sex, remember that you’re playing against the body’s natural way of being. Preparing for anal is easy, and the experience can be pleasurable for both partners. Here are some things that I want you to consider.

1When the rectum is clear, your partner won’t defecate on you or feel anxious about the possibility. Make sure she has a movement a few hours before sex and avoid foods that will cause flatulence and loose stool. If she is okay with using a water enema to clean inside, that’s an option too, but it’s not required.


2 The anus isn’t self-lubricating like the vagina. Make sure to use a copious amount of lubricant, whether it’s water-based, which is best for the body or silicon-based, which lasts longer.


3 There are two muscles (internal and external sphincters) that will try to stop you from entering. She must be able to relax the muscles in order to allow you to enter. Deep breathing and consciously relaxing the anus helps the process.


4The anus stretches, and it’s walls are thinner than the vagina. Take it slow, communicate with her throughout the process, and allow her to control your speed and depth. Using the head of your penis to stimulate the anus before entering is helpful. Start with your finger to get her used to the feeling of stimulation.


5Foreplay will dramatically improve your experience. Give her a full body rub from head to toe, front to back. You can also use oral sex and rimming to help her relax as well. When you turn her over, focus on as much booty stimulation as possible.


Remember that anal sex is an activity that requires your full attention. Be unattached to the outcome of getting in entirely on the first try. Be gentle and patient with her and with yourself. I recommend reading “The Ultimate Guide to Anal Sex for Women” by Tristan Taormino together to further deepen your knowledge about anal.

Have fun, and play safely!

With Love,

Glamazon Tyomi

 Follow our resident sexpert at @GlamazonTyomi.