How to Start Pegging – Part 1
Roleplaying

How to Start Pegging – Part 1

By Rebecca, 06.04.2020

We will walk you through the steps.

You know what is fun about anal sex? Pretty much anyone can do it! Anal play does not discriminate between genders or sexual orientations. All those nerve endings in the anus can feel pleasurable for anyone!

People in mainstream media have recently picked up on the fact that anal sex can feel good for anyone… even cis-hetero males! There has been an increase in discussions about pegging, with some mainstream movies mentioning it too!

The term “pegging” is used to describe a woman giving anal sex to a man by using a strap-on. While this article is geared towards that particular dynamic, the following tips can be used to talk about anal sex with anyone.

Pegging your partner can be really enjoyable. Receiving anal penetration can also be really enjoyable. It’s kind of a win-win situation if you’re both on board with trying it out. On top of the nerve endings, cis-males also have a prostate that can create different pleasure sensations. 

We don’t suggest jumping straight into pegging – there are a few steps to go through first.

1. Explore Your Butt
Before exploring your partner’s butt, you should try to explore your own butt. You should explore on your own as well as with your partner. Firstly, you might actually really enjoy anal stimulation. Secondly, you should become familiar with the sensations and know what anal stimulation feels like. Having your partner play with your anus can also help reduce any stigma you both have about anal play in general.

You don’t have to jump straight to large dildos or even a penis, you can start by exploring your body with fingers or small butt plugs. It is actually a great idea to start with smaller objects and work your way upward to larger items.

Safety note: If you are inserting a toy, make sure that it has a flared base (which makes it anal safe). Always wash your hands before and make sure your finger nails aren’t too sharp.

2. Explore Their Butt
Once you’re both comfortable playing with your anus, you should try to play with your partner’s anus. They should actually explore their body on their own, and then you should explore it together. Explore your partner’s anus with your fingers or a small anal-safe toy. Don’t bring up the topic of pegging just yet. Right now, your focus is on getting used to the idea and sensations of anal stimulation.

This is a great time to try to find and stimulate the prostate. Research what to look for and have your partner give you direct feedback about what feels good or not. Sometimes the prostate is easy to find but sometimes it is not.

Safety Note: During anal exploration, always use a lot of lubricant. At the beginning, it is better to put too much than too little. Once you’ve done it a few times you will be better able to assess the quantity needed. The butt does not self-lubricate, so you need to add your own. Add more than you think you need. Don’t use saliva.

3. Bring Up Pegging
Once you’ve both become more comfortable getting up-close-and-personal with each other’s anuses, you can bring up the topic of pegging. Don’t expect your partner to immediately say “yes.” If they do, that is great! You can skip the next step in this article. If your partner says “no,” then ask why they might not want to try it. If they say “maybe,” then have a conversation about any hesitations. Keep your conversation positive and judgment-free. If you were to say “no” to anal sex, you would want your partner to accept it and not pressure you, so you need to give your partner the same treatment.

When you bring up the topic, you can focus on how sexy you think it might be. Focus on the positives of trying out something new together. Always make sure your partner knows it is okay to say “no” at any point and that you will always respect their decisions.

4. Research Pegging Together
If your partner has concerns or hesitations, then it is important to research the answers. You both need to become mini-experts on the topic if you’re really going to try it out.

It is also important to go beyond the logistics. You should also be researching the sexy side of it. You can read other people’s experiences to discover the sensual and erotic side of pegging. Reading non-fiction erotic stories about pegging can help further an interest in the act. You can curate some stories and send them over to your partner for them to read alone. It is important to give them enough space for them to not feel pressured. Don’t inundate them with stories – just send over a few good ones.

The time between your first pegging conversation and the first time you actually try pegging can really vary. It might take a few weeks, a few months or even longer than that. Time is not important – the only important thing is that you both feel comfortable trying it.

Check out “How to Start Pegging – Part 2  about 2 weeks for more information!

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