A How-To Guide to Bottoming for the First Time

Engaging in anal sex for the first time, or the first time in a while, might feel uncomfortable without preparation. Preparation is a must, especially if you are the person receiving, or bottoming.

"Essentially, bottoming describes being the receiving partner when having sex through the anal cavity," explained Anthony Angeloni, P.A.-C., a board-certified physician assistant at Maze Men's Sexual & Reproductive Health in New York.

The topic is equally applicable to all genders, but here we focus on men having sex with men or men looking to explore anal pleasure.

It's important to begin by exploring your body and understanding your own anatomy, according to Martha Tara Lee, D.H.S., a relationship counselor and clinical sexologist with Eros Coaching, Singapore.

"Knowing your body and what feels good can help you better understand what to expect during anal sex," Lee said, adding that it's especially true with bottoming.

How to prepare to be a bottom and enjoy it

One of the main aspects of preparing to bottom is anal dilation, which refers to stretching the anorectal canal to prepare for anal sex, Angeloni explained. Since you are working with muscle tissue, Angeloni described it a bit like making a one-way street into a two-way road.

"There are men that can certainly just go for anal sex with no problems, but there are others who are unable to bottom easily," he said. "It can take some training for that muscle, just like you would train any other muscle at the gym."

This training can include using either specifically designed dilators or your fingers to get more comfortable with what you will feel during normal anal intercourse as a receptive partner.

Dilators

Some anal dilators are smooth and straight. They are typically used for medical purposes, but anal dilators used for pleasure are slightly different, said Lyndsey Murray, M.S., a certified sex therapist and the owner of Relationship Matters Therapy in Hurst, Texas.

"What I would recommend, especially if you are new to anal sex or bottoming, would be a dilator made out of silicone," she said. "It will shape to your body easier, and start out with the shortest dilator you can get when it comes to length."

Make sure the dilator has a flared base, too, so it has a stopping point, according to Murray. You don't want it to go too far in and then not be able to get it out.

Ensure your dilator is silicone—no PVC or PVC materials—because products made from PVC can become toxic or harbor bacteria over time, according to Angeloni. Anal dilators usually come in a set of different sizes.

"So start with the smallest dilator and work your way up," Angeloni advised.

Leed added that dilators can come in different shapes: tapered, ribbed and curved. Some anal dilators also have vibration settings for added pleasure.

Fingers

If you don't fancy trying a dilator, it is possible to explore anal sex using your fingers.

"Using one's fingers as part of anal sex can be a great way to explore the sensations and pleasure that can be experienced through anal stimulation," Lee said.

With the finger dilation method, you can use your index finger to stretch your anal sphincter over time. It can be a pleasurable way to massage the anus and lead to relaxation before intercourse. It might not stretch the walls of your anorectal canal as much as a specific dilator, but it can still stimulate the muscles to relax.

Murray outlined a few tips before using your fingers:

• Ensure your nails are cut, filed and clean.
• Start with external anal play before inserting your finger.
• Don't just go in and out. Experiment with moving your finger in different directions and explore a bit to see what your partner might enjoy the best.

Top tips for successful bottoming

The experts offered several other tips to make the bottoming experience better:

Be generous with lubrication

"Lube is essential for comfortable and enjoyable anal sex," Lee explained.

Make sure to use a water-based lube that is specifically designed for anal sex. You do have to be careful with some of the silicone lubricants, Angeloni said. Silicone-based lubes can react with silicone toys because of the reactivity of the chemicals.

"But water-based lubes are generally safer with most dilator sets, so you don't have to worry about cross-reactivity between the sets and the lube," he said.

Communication is key

"Talk to your partner about what you are feeling and what you want during anal sex. This will help ensure that both of you are on the same page and enjoying the experience," Lee said.

No type of sex should be painful. Angeloni stressed the goal is for both parties to enjoy it.

"It can be very nerve-wracking and frightening for people to get started with anal intercourse, so taking it slow and keeping open communication between partners is essential," he added.

Communicate with your sexual partner(s) before, during and after anal sex.

Think about practicalities

Murray advised following a diet high in fiber because it leaves less residue when engaging in anal sex. Fiber also makes it easier for you to empty your bowels. Completely emptying your bowels with each bowel movement can make anal sex more comfortable and leave less residue.

In addition, some people like anal sex to be completely clean, so they choose to wash their butt prior to anal sex. Just using a wet cloth or washing with soap and warm water is all the cleaning you need. However, some people might want to wash internally with an anal douche or enema. It really is a personal choice.

Be safe

No matter what type of sex you have, make it safer sex. Lee advised it's essential to practice safer anal sex, including using condoms to reduce the risk of sexually transmitted infections (STIs) and lubrication to reduce the risk of injury.

"Remember that the goal is to have fun and experience pleasure," Murray said. "When trying bottoming, have the mindset that it's supposed to be enjoyable, and take time to experiment and to find what is enjoyable to you within anal sex."