Home Advice Oh My: 8 Sexy Pro-Tips For Handling Very Big Packages

Oh My: 8 Sexy Pro-Tips For Handling Very Big Packages

I thought big packages were supposed to be a good thing! Do you have any tips for having sex with big penises without hurting yourself?

No, but really — how does a person have have better sex or a better relationship? The Fresh Toast has enlisted Rachel Krantz, a sex writer and proud canna-enthusiast, to help readers out with some answers as its sex columnist. No question is off limits, and all questions will remain anonymous. Please send your sex and relationship inquiries to freshlove@thefreshtoast.com. Now, onto this week’s topic: tips for having sex with a man with a big penis.

Q: Hi, so I’m a 21-year-old woman, and I just started falling for this guy who is very well-endowed. I’m not exactly sure how big his penis is, only that it’s the biggest I’ve ever slept with, and sometimes it hurts. I thought a big dick was supposed to be a good thing! I really like him, and I feel bad that he can’t always be all the way inside me. Do you have any tips for having sex with big penises without hurting yourself?

A: Oh, man. You never forget your first too-big dick. Mine was a dude I dated for about a month in college, and I definitely didn’t quite know how to handle him. I sometimes wonder how much longer we would have dated if I knew then what I know now. (Probably not. I think he was a Libertarian.)

Anyway, the point is, big dicks can be managed and enjoyed! The key is to know how to respect your own limits as the person receiving them. Here are my tips for dealing with a big penis.

1. Don’t Push Yourself Into Anything That’s Too Uncomfortable

This is the main thing I want you to understand. Yes, there is a learning curve here (though, for your sake, I hope there isn’t too much curve going on) but above all else, you must, must listen to your body and limits. If you don’t listen to yourself in the interest of grinning and bearing it to be tough, your body won’t learn to trust his penis, and you’ll always be clamping up on some level — not to mention, you’ll be having inauthentic sex.

RELATED: 8 Essential Questions To Ask Yourself Before You Have Sex With Someone

Take it slow, be honest with him about the fact that this is the biggest penis you’ve encountered, and let him know you’d like to work on enjoying it with him. If he’s worth keeping, he will understand that this is a process, and he won’t want to do anything to cause you pain. Don’t be afraid to let him know when it hurts too much, when you need to change positions, when you need to apply more lube, or when take a break. Sex is not supposed to be painful, and while there is an element of “learning” here, you’re shooting yourself in the pussy if you push it too far.

2. Always, Always Make Sure You’re Thoroughly Primed

This should go for all penetrative sex, but when it comes to dealing with a big joystick, it’s especially important not to engage until you are thoroughly, drippingly aroused. That means letting him know that he needs to always make sure you’re very wet before he tries to put it in.

That can mean lots of juicy oral or fingering, but it can also mean whatever gets you wet — trying orgasmic meditation, using vibrators, making out and dry humping, watching porn and groping each other — whatever. The point is, intercourse should never be rushed, but especially not when you’re operating particularly heavy machinery.

3. Use All The Lube

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Hopefully you knew this one was coming. Lube is always a great idea in my book, but with a big dick, it is a necessity. Use it religiously, and if it feels like you’re the one who always has to break it out, make it known to him that you’d like him to be proactive about applying it as well. It’s also important that your lube isn’t filled with chemicals, fragrances, or other junk that might irritate your vagina. For a thinner, more slippery lube, I like AstroGlide Natural Lube, and for a thicker, more gel-like lube (which you might find has more staying power) I recommend LELO’s lube.

4. Know Your Go-To Sex Positions

All sex positions are not created equal. There are going to be some sex positions that make it easier for you to accommodate a big dick, and there is no shame in preferring them. Generally, positions where you drive are your best bet — Reverse Cowgirl, Woman on Top, and Side-by-Side are all good bets. Just trust your intuition and assert what feels good.

5. Consider Incorporating Vibrators

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(This also works well if you’re trying to get used to anal, by the way.) If you use a handheld clitoral vibrator in positions where you have access, you’re going to keep yourself more wet, aroused, and accommodating to a big penis than you would be otherwise. My favorite is the LELO LILY 2, but if that’s out of your budget, look for something with a similar shape.

6. Practice Redefining Sex

Unfortunately for women and non-hetero people, our society still tends to think of sex as P-in-V intercourse. In fact, sex is a much broader term that can encompass oral, fingering, mutual masturbation and really, just about anything else that’s sexy and that you both consent to.

RELATED: 6 Smart Sex Tips For Men Who Want To Please Women In Bed

If you give it a go and are just not feeling it that night, suggest jerking each other off. If he’s craving the feeling of thrusting fully into you, you can always make an impromptu crevasse out of your boobs, and you can enjoy the erotic/hilarious view. The point is, you should always both remember there are many, many more things on the menu.

7. Never Gag Yourself (Unless That’s Your Thing)

It pains me that I have to say this, but I wish someone had said it to me at 21. Deep-throating is really mostly just a porn thing — and it should never be the expectation that you gag, nor should he be forcing his dick into your throat at a depth that feels uncomfortable. Especially since he’s big, make it clear that you need to drive during oral, and that he can sit back and enjoy the ride.

Remember that the most sensitive part of the penis is the tip anyway, so focus on sucking that and the rim, and use some lube on your hand for the base. You’ll be more into it than if you’re trying to force anything, which is what’s actually sexy.

8. Be Patient With Yourself — And Demand Patience In Return

Remember: a baby can come out of there, so you can probably handle more dick than you think. When it’s feeling bad, it probably has more to do with you not being wet and turned-on enough. (Though, to be fair, I haven’t seen this dude.) The point is, be patient with yourself.

Like I said, this all comes down to knowing your limits, and practicing the grown-ass art of asserting them. I do feel for the guy, but if he doesn’t think you’re worth making accommodations and being patient for until you’re comfortable, then he doesn’t have a big dick so much as he just is a dick.

Good luck, and remember: sex should be fun, not a test of your ability to dissociate from your body.

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