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8 Tips for Extreme Penetration

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Every now and again, a woman may want a little “more” and long for extreme penetration. She may want something bigger, harder, longer, wider or deeper to penetrate her vaginally.

When a lover found one of my super-sized dildos as he was searching for a robe after sex, he was concerned that I wasn’t satisfied. Miss Molly, a cheerful neon pink silicone affair, is quite a hefty gal. I can’t wrap my hand around her. In fact, I can barely accommodate her at all.

I assured him that his dick size is normal—Miss Molly doesn’t exist in nature. No man has her measurements, except maybe a centaur. I seldom long for Miss Molly and all she has on offer. I love men, each of you hung a little differently, various sizes and shapes of cocks. Nature made you, and it works perfectly with me.

However, every now and again a woman wants “extreme penetration.” She doesn’t want it all the time. She has to be abnormally aroused.

Some women never want it, but lots of us have special occasions where arousal is next level, or it’s just the variety of something different or new.

8 Extreme Penetration Tips

1. Keep a toy box with different sizes of dildos.

More often than being asked about Miss Molly, I’m asked about Slim Jim. Jim is a beautiful glass wand with a slight bend, barely thicker than a finger and four inches long. Guys who see him in my bedside table drawer want to know why I want a small or average-sized dildo.

Well, variety. Stretching to capacity is a tremendously pleasurable sensation at times. But more often, it is painful or unnecessary, or neutral, or just one of a range of sensations. It’s fulfilling at times to reach your limit, vaginally, so to speak. But a small dildo, or a finger, is also exciting—it is teasing and flirting and tormenting and promising.

Be creative and keep a range of penetration options nearby. Look for various ways to enhance her pleasure with your imagination.

Read: A Beginner’s Guide to Double Penetration

2. Use your imagination, not just dildos.

Dildos are the best way forward for larger items for vaginal penetration, because they are created with that purpose in mind. They are easy to sanitize. They are designed for the deed.

You can use many props for penetration. Your fingers or your hand—read up on safe fisting techniques and give it a whirl. Carrots, cucumbers (use common sense and clean them first). I’ve used a shampoo bottle (depends on the design), a rolling pin, and zucchini. If you don’t happen to have a huge dildo when the desire strikes, you’ll need to think creatively and rationally at the same time—look around in the kitchen and bathroom for safe opportunities!

Read: Penetration Kinks: Objects of My Desire

3. Don’t always think bigger is better.

You see this keeps turning up, even in a post about extreme penetration. To be a good lover, you have to get out of that mindset that bigger is better and see the whole picture.

Read: How to Find Deep Penetration with any Size

Even if she loves a huge cock, and you don’t have one, that is still not the whole story. You cannot just pick up a giant dildo like Miss Molly and try thrusting it in. You will injure her. It will not be pleasurable.

Guys with bigger dicks often think it’s all they need. A woman needs to be opened slowly. So, I repeat, EVEN when her preference is for massive, that’s not all it takes. It takes a slow hand, a variety of strokes, a building of arousal, and more. There’s nothing LESS erotic than trying to slam home a big piece of meat with no ceremony—not hot.

4. Men love extreme penetration too.

Women may enjoy having extreme penetration performed, but it’s not just us. It’s a very common fantasy of males to view or enact extreme penetration. You probably fantasize about a male with a larger cock than you have, even if yours is big enough—this is a popular fantasy and can be played out in cuckold kinks, but it’s not just a humiliation or BDSM thing.

It’s exciting to witness her “take” a big dick. Men love the idea of penetrating a woman—its basic stuff, really. Extreme penetration is simply exaggerating the basics and most men find it very exciting to imagine or watch her use a large toy or take it from another man.

5. Building arousal is key to extreme penetration.

Do not introduce extreme penetration unless she is extremely horny. Better yet, talk about it ahead of time and plan to “get there” through slow, arousal-building sex.

6. Use lots of lube.

Have all kinds of lube on hand to experiment with, or just keep a tub of her favorite variety. Always use loads of lube when going big.

7. Practice safe penetration.

You may have seen some weird things in porn, like women taking on a two by four. Hello, splinters? We can accommodate a baby, but it is painful. Make sure you are thinking of the skin of her vagina, of bacteria and germs, of her comfort. Never push violently in the heat of the moment, and don’t use materials that can injure her.

8. Save extreme penetration for special occasions

Women can find extreme deep penetration to be very fulfilling and exciting, but it’s not something we want every day. It’s exhausting and special. Intense, yes, but it’s not “better” than everyday sex.

Our bodies are made for delivering babies and can sometimes stretch more widely than necessary to accommodate your cock. That can be really hot and exciting, but no woman wants a fist inside her every day or a huge dildo either, so just because we love it doesn’t mean we always want it. Enjoy it as an occasional indulgence but if she says she’s not up for it, take her word for it!

Read: Fisting: What You Need to Know

Do you practice extreme penetration? Please share your tips in the comments!

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