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7 Tips to Make Your First Time Bottoming Absolutely Amazing

by | Apr 28, 2024

If there’s one position that reigns supreme: bottoming. It’s a rite of passage for any sexually active man. There’s nothing hotter than the feeling of having your ass filled and stroked while you’re doing the stroking yourself.

However, you might be wondering what to expect when you bottom for the first time. 

While it can be nerve-wracking to think about, there are ways to take your first time bottoming to the next level That starts with getting to know your body, understanding what to expect during anal sex, and learning how to take your partner’s dick the right way.

If you are new to bottoming, HomoCulture has rounded up some of the best tips to help you make your first time bottoming absolutely amazing.

The Celebration of Light fireworks at English Bay in downtown Vancouver.

1. Prepare Yourself Mentally

They say sex is all in the mind, and rightly so in this case. Getting mentally prepared for your first-time bottoming is key to having a good experience. This means taking the time to relax and getting yourself aroused before anything happens. 

This can be done through stimulation with your hands or a partner or through an orgasm-inducing toy such as a dildo. You might also want to experiment with anal masturbation to get used to the sensations and understand what feels good. 

Remember: you want to be aroused and comfortable before taking anyone else’s penis or sex toy inside you.

2. Clean Yourself Beforehand

Hygiene is paramount before engaging in anal sex as it will help avoid making a mess. There are a few aspects that revolve around cleaning yourself out before bottoming:


First, you will need to watch what and when you eat. Consuming a high fiber meal (i.e., fruits and veggies) is highly recommended as it helps in bowel movements, thus keeping you clean down there. 

In the same way, give yourself enough time for food to digest before bottoming. Don’t get down to business moments after a heavy meal, as it could lead to bloating or discomfort. Some 3-4 hours after a meal should be enough for digestion before having sex. 


Anal douching is the act of flushing out one’s rectum with water. It involves using an enema made from medical-grade silicone and is safe and straightforward to use. A disposable enema kit can be acquired at a local pharmacy or drugstore, or you can get a large squeeze bulb with a silicone or plastic nozzle. 

Anal douche till you are clean, but do not overdo it. As much as you want to stay clean down there, ana douching takes a toll on your insides; thus, if done too much, it could leave you open to both STIs and common infections. 

3. Use Lube

When it comes to bottoming, lube is your best friend. It is one of the keys to the first pain-free bottoming experience. The rectum does not self-lubricate hence lube is important for any anal play. You’ll have to use plenty of lube especially if he’s really hung. This will help reduce friction and make the experience more pleasurable for you and your partner. 

When choosing a suitable lube, water-based or silicone-based lubricants are generally recommended as they work well with all types of condoms. And since you’ll have to deal with lube stains on the bedsheets after sex, you can get rid of them through any of these six ways.

4. Wear a Condom

Fine, we know you want to feel the bare sensation and pleasure that comes with barebacking but at least use a condom. As a beginner, you are still trying to master the art of cleaning yourself out, so a condom will come in handy if you, unfortunately, mess up.

Wearing rubber will also help you stay safe from health problems as anal sex comes with high levels of risk for sexually transmitted infections and diseases (STIs/STDs). After all, safe sex is pleasurable sex.

5. Take Things Slow

Do not be in a rush to take that dick. Remember, it is your first time doing it, so your anal sphincter muscles are still tight. Therefore, even the slightest of ramming by the top will have you wailing in pain. Take a deep breath as he slowly inserts that dick in you (and speak up if you feel any sort of discomfort).

Likewise, do not clench your sphincter muscles, as this is what causes pain. If you come across a top who is considerate enough to ease you in during the process, please keep him!

6. Stroke Your Cock.

This is something that many guys forget to do, but it feels super amazing. By stroking your penis as you get penetrated, you’ll help increase the pleasure you feel. Even tops like it when you rub your dick, and it lets them know when you’re ready for them to go harder or faster. 

The amazing thing about this practice is that you end up getting mind-blowing, toe-curling orgasms! It’s pretty much jerking off while having your prostate pounded intensely. Heck, you’ll even wonder what all that anxiety and nervousness was all about.

Also, don’t worry if you aren’t getting a boner when he’s inside you. Blame the anxiety that comes with bottoming for the first time. Don’t panic, though; the hard-on will come with time.    

7. Do Not Force It

If things do not work your way, don’t force it. You might realize that you are not wired to be a bottom — and that is OK. Let your partner know if you are not mentally ready for it or if you want to stop midway through the sex session. 

Perhaps you’ll need to go back to the drawing board and familiarize yourself with anal sex toys to help you get well prepared for the real act. 

Unfortunately, It’s Not All Roses and Unicorns

Bottoming is a huge step for anyone, and it can be daunting to think about all the things that could go wrong. But remember, shit happens. You’re going to make mistakes, and that’s okay. Just relax and try not to be overly self-conscious. Have a sense of humour about it and move on.

Bottom line: relax, prep, and communicate and you’ll be just fine

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Brian Webb

Brian Webb


Brian Webb is the founder and editor-in-chief of HomoCulture, a celebrated content creator, and winner of the prestigious Mr. Gay Canada – People’s Choice award.An avid traveler, Brian attends Pride events, festivals, street fairs, and LGBTQ friendly destinations through the HomoCulture Tour. He has developed a passion for discovering and sharing authentic lived experiences, educating about the LGBTQ community, and using both his photography and storytelling to produce inspiring content.Originally from the beautiful Okanagan Valley in the southern interior of British Columbia, Brian now lives in Vancouver, British Columbia. His personal interests include travel, photography, physical fitness, mixology, drag shows.

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