Five Tips when Bottoming for the First Time

Bottoming can be fun for everyone but can feel intimidating to first-timers. Here, I talk about my top five tips to help those exploring it for the first time.

First, let's explore some myths. Anal sex is for everyone. Men, women, gay, straight, pan, genderqueer, young, old, it doesn’t matter. Yet, people think you have to be a certain kind of person to enjoy it. Let's look at three toxic beliefs:

First, it is said that women don’t like anal sex and don’t need to do it because they have a vulva/vagina.

Second, if men put anything in their butt, it automatically means they are gay.

Third, back to vulva owners, they are sluts if they engage in the act.

All of these couldn’t be more false and the only reason we believe these toxic motions is due to poor sex education, purity culture, and sex negativity. So if this is your first time hearing this, let me be the first to tell you that ANAL SEX CAN BE A VERY PLEASURABLE EXPERIENCE FOR ANYONE AND EVERYONE!

Now, let's dive into what I think is important for first-timers.

1. Do it with someone you trust

I think first and foremost, when you are bottoming for the first time, you want to do it with someone you trust. I don’t care if you are a cis gay dude and have been dreaming about bottoming your entire life. This can be an emotional thing the first time around and when we engage in it with someone we feel secure with, that can go a long way in overall enjoyment and wanting to do it again in the future. Anal penetrative sex can be a very vulnerable thing to do. While I am a huge fan of casual sex, when it comes to doing anal sex for the first time, let's find someone we trust.

2. For the love of god, hygiene

For the first go around, shower ahead of time. This will make you feel more comfortable and receptive to intimacy. As humans when we feel clean, it makes us much more excited to get dirty!

3. Pay attention to your diet

There really is no need to douche, as much as people want you to believe there is. The best way to avoid any accidents is to have a healthy diet. A "healthy" diet is what it sounds like: not a ton of alcohol or drugs, fast food, or anything high in fat. If something upsets your stomach, we don't want to have it before we bottom. For instance, I am lactose intolerant but LOVE PIZZA. I would have to pay attention to that if I plan on bottoming that day. But if you really want to douche, you have my blessing, but don’t do it frequently as we have healthy anal bacteria and douching is the number one way to clear all of it out. This will lead to more problems than solutions.

4. Preparation is key

When it comes to preparing for anal play, this can be done with or without a partner. I highly encourage people to penetrate themselves first before they let someone else do it. I would start by rubbing the anus with some lube and then slowly inserting a finger. From there, feel free to use a butt plug or a smaller dildo. When a partner is involved, make sure the rectum is nice and ready. I encourage people to use their tongues, fingers, and toys to help loosen up the other partner. Once your body and mind feel relaxed, you are ready to go.

5. Take it slow

And finally, when you begin, take it very slowly. Use a lot of lube, and breathe. We are trying to open our interior rectum and that can be hard to do. So if we just go and shove, idk, a penis in there, we are going to cause a lot of damage to the area. The slower we go, the more relaxed we become, and that opens us up to experience pleasure. If you experience sharp pains, pull out, breathe, and then try again. Always, always, always, listen to your body. It is never wrong when it comes to anal play.

Final thoughts

Don’t freak out if there is a little blood during or after anal intercourse. Some tearing is expected. This is why we use a lot of lube and go slow. The anus and rectum will heal themselves in time. Anal play can be extremely fun and erotic. Don’t shy away from it just because you heard it will hurt.

Cleveland Sex Therapy is owned by Matt Lachman, a licensed professional clinical counselor and certified sex and relationship therapist who specializes in working with individuals, couples, and polyam folx on their concerns relating to sexuality, intimacy, and overall sexual health. The goal of Cleveland Sex Therapy is to promote inclusivity and nurture sex positivity. For more information, feel free to contact him at