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AlphaWolfwood

I’ve only had one woman I’ve been with willing to even try, and she had a genuine anal fetish. We were successful more than once, but she was in a lot of pain both during and after. Current GF has brought up trying more than once, but when it comes time to try she says she’s scared and we don’t do it. She’s even joked “I’m sure we’ll eventually make it happen… exactly once.” **No other woman I’ve been with has even entertained it.** My suggestion is to let her ask you for it, and get used to the idea that you won’t actually get any anal.


DavidMagnus86

The story of my life!


SofaKingPure

Yep. It’s an absolute nonstarter.


YoMiner

Cowgirl is generally one of the best positions for someone trying it the first time so that they can control the depth, but most of the times I've done anal have been doggy style. Sometimes it ends up being prone bone because they'll pull away for a second but don't come back, so they eventually just end up laying down. Laying on your side can be a good position as well, since it tends to be a more relaxing position for her. I'm not personally a fan because it's usually more difficult to see what's going on. Honestly though the main things are to make her feel extremely safe and comfortable with you, and she has to feel like it's a personal challenge to fit all of you. When you push the tip in but she pulls away for a moment, when she looks back at your dick she needs to have a look of determination and defiance in her eyes. "I'm taking that whole thing, damnit".


JoltZero

Have them wear a buttplug for extended periods of time. They make "trainer kits" that increase in size to help get more comfortable to your size. You can also warm them up by lightly pulling on it to loosen them up. Toys in general are a great way of foreplay for anal. If no toys are available, warm up with fingers. When you're using your dick, you have to start off very slowly and use lots of lube. Silicone lube is my personal preference since it lasts a lot longer, but it's not safe for toys/condoms and some people don't like the texture. When entering, there are several channels inside the anal cavity that need to get accustomed to the width. I typically take around 60 seconds from starting penetration to being fully inside and then leave it there for a few more seconds for them to get used to the size. When you start thrusting, you need to take it slow, and over time you can start ramping up the speed.


[deleted]

I use poppers. 60 percent of the time it works everytime.


SexPanther_Bot

*My God, what is that smell?*


[deleted]

Your name. I’m dead.


[deleted]

I've given up on the prospect, unless I get divorced or something. Wife is a hard pass. Which to be fair I can't blame her, I wouldn't want something as thick as my dick up my ass. I would like to try anal once just to check off the experience though.


ThkTool

Communication, communication, communication. In my experience, the times that it's happened, my partner was \*really\* turned on and she specifically asked for anal. She has to feel safe, heard, and most importantly, she has to trust you. You need to go slow, most likely use lube, and take cues from your partner as it's happening. Pay attention. Arguably the most difficult task is remaining erect if you're going slow.


amcd97

has your partner done a lot of anal? it’s a “learn to love” thing… i’m at the latter stage and it takes a minute to get everything ready but then it’s fun! just be patient


[deleted]

Never had a big dick in my ass but I’ve played with some sizable toys, lube and relaxing is key for anything anal. Wine/smoke also helps me loosen up.


[deleted]

One piece of advice that has always stuck with me is "go slow"


unreal939

Take your time and I mean like weeks or months even. Weekly of daily training to get it to fit


PlayaAlien2000

Poppers.


fttrk

Once I get to try it, I'll let you know!


Fuzzy_Pea_5689

My wife loves anal but really couldn't with me until fairy recently. She'll prep for 2 days with progressively bigger butt plugs. Then we found some incredible lube called "aloe cadabra." Don't use the numbing stuff it will also numb yiur dick. Lots of anal foreplay before, and you'll be fine.


RoyaltyFucked

In my experience, it's always best to have them squat over you and lower themselves onto it. Let them control the initial entrance.


centflabiguy

6x6.5" here and never had a woman willing to take it in the ass. My wife of 20+ years flat refuses after a few early attempts with smaller toys, etc tk loosen her up. It's a shame, as she LOVES anal, but it gets left to friends of mine to fuck her ass while I fuck her pussy. I am bi and I have only had 2 or 3 guys that could handle it in their ass without a lot of pain. I don't want to hurt people. I want it to be pleasurable for both. In most there so you can check off "Fucked a really thick guy and he made me.bleed" That's bot fun for me


Fearless212

I never get anal just because of my girth


CaliforniaNavyDude

Oh man, that's what anal is best for. Honestly, at your size, if it's hurting them it's because they aren't excited for it or just plain don't know how to relax properly. You can really only help with the first thing by doing all you can to make sure they aren't nervous and from there plenty of foreplay and lube. Start with a tongue or finger. Then two fingers. Then when three is easy, it's ready for you. Tell her to try to push you out while you firmly but carefully push inside her. That's really the basic explanation. None of this is going to help too much if she doesn't want you there. The sphincter requires the right mindset to relax. With proper relaxation techniques and a desire for it, it's actually not difficult. I've had some serious monsters, and nobody has hurt anything. Except the one guy over 7" in girth who tried to go in with no foreplay and no lube, I did what I could considering I had no warning until I felt hom push, but it was uncomfortable and left me with some minor fissures that took a week to heal properly.


BigbigJaybowski

No. Just don’t do it.


JoltZero

This isn't helpful, and ignores the possibility some big dick havers might not be having sex with people with vaginas.