u/Aphraea-of

“How to get her to peg me” or “How to get him into pegging” - these are probably the most asked questions on this sub. Every time it comes up we try to answer, but there’s no one-size-fits-all answer. Relationships and sex lives are so different from couple to couple. For some it’s easy and natural, for others it feels almost impossible.

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You gotta be real with yourself about where you are in your sex life right now. You can’t just hit your partner with “Peg me” if until yesterday you were doing straight vanilla sex under the covers with the lights off. Openness, trust, and communication are the real keys.

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If you’re at a low level and never used toys, that’s where you start. If you’re in the middle and already comfortable with toys, you’re in a good position - maybe start with a butt plug in your ass, then slowly move to dildos and so on. If you’re already at a high level, it’ll probably be a lot easier to bring up.

So how you approach it depends completely on your situation, but small baby steps are the most important thing. Understanding the topic and explaining it properly matters a lot because a lot of people don’t even know what pegging really is. Many connect it to being gay or losing masculinity, and that’s the #1 reason it fails - either the guy feels shame or the girl gets weirded out by the same stuff.

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You need to explain that pegging won’t make him/you gay or bi if he/you aren’t/isn’t already. It’s just exploring anal play together with your partner and no one else. Whatever your partner decides after you lay everything out, you have to respect it. You can’t force someone’s beliefs.

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Here are different ways you can bring it up (choose what actually fits your relationship):

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1. Sexting - If you already sext, this is great. Share articles about prostate play or pegging. Or send soft, erotic gifs/pics (start mild, not full BDSM stuff).

Build it up like “This looks incredibly pleasurable - would love to try something like this with you someday.” There are really beautiful gif/pic/videos of the act that you can share with your partner but don’t go directly with some BDSM Femdom crossdressing scene.

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2. Watching a movie - Deadpool has a pegging joke. Also Zack and Miri Make a Porno, Double Lover, The Brass Teapot, Young People Fucking, etc. Use the moment to bring it up.

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3. Watching porn together - If you do this, it’s the perfect chance to show exactly what you want.

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4. Direct but gentle conversation (pillow talk or neutral setting) - “I read an article about prostate pleasure and pegging - it sounds really hot to explore together. What do you think?” Tell her why it appeals to you.

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5. Shop for toys together - Browse small butt plugs, prostate massagers, or beginner strap-ons. Keep it playful: “Let’s pick something small to experiment with first.”

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6. Incorporate during foreplay - If you already do light anal touching: “I really like when you touch me there - would you be open to trying a finger or small toy next time?”

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7. Fantasy sharing game or Yes/No/Maybe list - Put pegging in a list with a bunch of other ideas so there’s no pressure.

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8. Blame it on an article - “I came across this piece about how good prostate stimulation feels… got me curious. No pressure though.”

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9. Non-sexual setting - Over breakfast or on a walk: “I’ve been reading about pegging and prostate pleasure - sounds amazing. Would you be open to talking about it?”

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10. Emphasize vulnerability & exclusivity - “This excites me because it’s with you. I love being vulnerable and sharing this only with you.”

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11. After her orgasm - When she’s relaxed and happy: “That was amazing… I’ve been thinking about something that might feel incredible for me too.”

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12. Tie it to her existing kink - If you already have dom/sub or role reversal stuff, frame it as an extension of that.

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13. “What if” game - Take turns finishing “What if we tried…” sentences and throw pegging in casually.

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14. For more conservative partners, start with education (articles/podcasts) and small non-penetrative wins first.

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Bonus: Listen to Ruby Ryder’s Pegging Paradise podcast - really helpful.

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Final tips:

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- Don’t surprise her/him with gear out of nowhere.

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- Focus on her pleasure too - a lot of givers actually enjoy the power, closeness, or how it looks.

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- Be patient and willing to compromise (fingers/toys instead of full pegging).

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- Cleanliness is important - shower together, watch your diet/fiber.

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- If there’s strong resistance because of stigma, more education might help, but sometimes you just have to accept it might not happen.

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- It may take weeks, months or even years.

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Pegging and prostate play can be super connecting when both people are into it. The goal isn’t convincing someone - it’s shared pleasure and trust. Good communication is everything.

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Good luck guys and gals.

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Hey there!

Over the past 10+ years, I’ve learned a lot about anal play both giving and receiving, and I’m excited to share my best tips for comfortable deep anal penetration with you.

Many people have shared their experiences with longer toys and the common frustration: they can’t seem to get deeper than 15-20 cm (5–8 inches) before hitting a wall and feeling pain or discomfort. This guide is written exactly for you.

First, I want to be upfront: people’s bodies are different. There are some who, no matter what they try, won’t be able to take anything significantly longer. But I want to reassure you, most people are absolutely capable of inserting extremely long toys. You just need the right preparation, proper guidance, and plenty of patience. I’m here to guide you through it step by step.

Quick Anatomy Reminder

The human rectum is the space between the start of the anal canal and the rectosigmoid junction. It’s typically 10–20 cm (4–8 inches) long. This is where most regular penetration happens. If you want to go deeper, the key is getting past that rectosigmoid junction. Once you manage that, you’ve done about 80% of the job.

The average person, with the right preparation and patience, can comfortably take toys up to 70–80 cm (27–31 inches). More experienced players can enjoy 100–150 cm (39–59 inches) with dedicated training. But today we’re focusing on the most common issue: breaking through that stubborn 15–20 cm (5–8 inches) barrier so you can confidently use 30–40 cm (12–16 inch) dildos and beyond.

Essential Tools You Need

Here are my most crucial recommendations to set yourself up for success:

- High-quality water-based lube: X-Lube is one of the most popular choices because it’s cheap, mixes into a thick, long-lasting gel, and performs incredibly well for extended sessions.

- Lube shooter: This simple syringe-like device lets you shoot generous amounts of lube deep inside your ass. Remember there is no such thing as too much lube. Flood yourself thoroughly.

- The right toy: Always go for good platinum-cured silicone from reputable indie makers. I strongly suggest avoiding cheap Chinese and Amazon brands. Most people start with standard pegging dildos around 15–30 cm, but there are special colon dildos (50–100 cm and longer) designed specifically for depth play. In this guide we’ll mostly cover pegging and solo play with 30–40 cm (12–16 inch) toys.

Thorough Preparation

People usually prepare for regular anal sex with a small enema that just cleans the rectum that’s perfectly fine for toys up to about 20 cm. However, when you plan to go past the rectosigmoid junction, you need a full colon cleanout. If the large colon is still full, there simply won’t be enough free space for the dildo to slide in comfortably, leading to obstruction and discomfort.

If you don’t know how to do a proper full cleanout enema, check my enema guide (linked here https://www.reddit.com/user/Aphraea-of/comments/1fpdloq/enemas\_general\_information\_and\_faq/?utm\_source=share&utm\_medium=mweb3x&utm\_name=mweb3xcss&utm\_term=1&utm\_content=share\_button). And very important: wait at least 60 minutes after your enema before you begin playing. Give your body time to settle and relax.

Best Positions for Deep Play

There are two main positions that work especially well for deep anal penetration. Once you gain more experience you can experiment with others, but start with these:

- Face down, ass up: This is my strongest recommendation. In this position gravity helps pull the colon downward, straightening out the natural curves and making it much easier for the dildo to pass the bends.

- Lying on your left side. Also very effective for navigating the sigmoid curve.

The Powerful Air Trick

This is a technique I learned years ago and have used ever since because it works so well. By introducing air into the colon, it travels ahead of the dildo and gently opens the passage in front of it. This helps tremendously when passing the bends.

Two easy ways to do it:

1. If you’re using a dildo that gapes you slightly, pull it out relatively fast so your hole stays open for a few seconds. Air rushes in naturally. Then push the dildo back in slowly and deeply. Repeat this 2–4 times.

2. Use a small hand bulb pump or balloon pump just give a few pumps and then follow immediately with the toy.

Yes, accidental farts can happen. Mild bloating is also possible depending on how much air you introduce. As I always say: don’t go into the forest if you’re scared of bears. Embrace the process.

Recommended Toys

For pegging or solo play, I recommend a high-quality platinum-cured silicone dildo from an indie store. Aim for medium softness (there are options like SOFT 0030, Medium 0050, Hard 10A). Choose a comfortable diameter/thickness, but for starters try not to go over 4–5 cm (roughly 1.6–2 inches diameter).

For serious depth play, look into specialized toys called colon snakes, colon dildos, or Slink dildos. These are specifically designed to travel really deep 60–150 cm and should always be made of platinum-cured silicone.

How to Do It – Step by Step

Do your foreplay and proper anal stretching first (check my stretching guide https://www.reddit.com/user/Aphraea-of/comments/1lxh92e/my\_guide\_to\_safe\_and\_comfortable\_anal\_stretching/?utm\_source=share&utm\_medium=mweb3x&utm\_name=mweb3xcss&utm\_term=1&utm\_content=share\_button). Never skip this part, it makes everything smoother and more pleasurable.

Get into your preferred position. I strongly suggest starting face down, ass up.

Use the lube shooter to put 1–2 full syringes of lube deep inside you. Generously cover your dildo with plenty of lube as well.

Especially when you’re first trying deep penetration during pegging, start by holding the dildo in your hand for maximum control.

- Slowly slide it in until you feel the first resistance or discomfort, then pull back. Repeat this 10-20 times to loosen and prepare the way.

- Now bring in the air trick: pull the dildo out relatively faster so air can rush in, then push it back in slowly and deliberately. Repeat 3–4 times.

You’ll quickly discover that with every cycle the dildo travels deeper and deeper until you can take the whole length comfortably. During this process you may hear interesting gurgles and feel new, strange, incredibly full sensations from the deeper penetration. These feelings are completely normal and can become intensely pleasurable.

Important rule: There must not be sharp pain or huge discomfort. If you feel real pain, you are either using too much force or the dildo is still too big for your current level. Slow down, add even more lube, or step back to a smaller size. You can also switch to the left-side position and try again from there.

Once you’ve successfully passed the bend and enjoyed around 5 minutes of steady, deep play, you can attach the dildo to the harness and continue with proper pegging. By now the colon has straightened out and adapted, so you’ll often be able to change to your favorite positions more freely.

Taking It Even Deeper (50–150 cm Colon Dildos)

After passing the first major curve, longer colon dildos can often slide in 60–70 cm with surprisingly little resistance. When you reach this stage, switch to lying on your back for better control.

At these greater depths the colon has almost no pain receptors and very low sensitivity, so you must be extremely careful and move very slowly. Never force anything, listen to your body at all times and progress gradually over multiple sessions.

Final Tips and Encouragement

- Always use massive amounts of lube.

- Stay patient rushing is the quickest way to discomfort.

- Clean your toys thoroughly after every session.

- If anything feels wrong, stop immediately and reassess.

Follow these steps exactly, stay relaxed, and be consistent with your training. You’ll soon be taking impressive lengths with comfort and pleasure you once thought was out of reach.

Now get yourself prepared, get into that face-down-ass-up position, load up with lube, and open that hungry hole for deep play.

I’m guiding you the whole way. You’ve got this. Enjoy every inch.