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You can buy anal training kits specially designed for this. This is because the rectum doesn’t self-lubricate, so you’ll need some extra help. Read a book, scroll TikTok, or find your high school enemy on LinkedIn. They do this by numbing the area. If I had to pick one thing that’s a wish, not a grievance, it would be for the tank top to be somewhat more breathable material and cut a little differently at the bottom.

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"The sooner you stop," Dr. Goldstein says, "the lower the risk of complications or injuries". This is more likely if you’re new to bottoming, haven’t bottomed in a while or if your partner is bigger than you’re used to. And it doesn’t have to be.

Depending on your partner’s size, you will probably need some preparation.

Enter, Freddie!

In general, start small before slowly progressing in size.

Pain is useful. Want to learn more? These are ones that give the bottom more control over how fast or deep you go.

Positions where you’re on top, like cowgirl or reverse cowgirl, can be good ones to start with. Love it!

The Freddie Guide to: Bottoming

Bottoming is an art.

Sometimes, it might be both. It keeps things moving smoothly and can help prevent pain or discomfort. If you start slowly, breathe and focus on relaxing your muscles down there, it should gradually feel better.

In general, bottoming can be a confusing sensation for your body. The beauty of queer sex is how many options we have.

You can do this yourself with some of the steps above, or you can do this with them during sex. If you’d like, you can then progress from fingers to toys. But queer sex and sexual identity can be so much more than these two.

During foreplay, go slow. Silicone-based lube is a good option that works well with condoms and most toys.

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If your pain is severe or you see more than a few drops of blood then get medical help immediately.