Accomodating her better

Use a lot of lube and work your way up to a larger one by using smaller ones first. I learned the hard way, on my back on an operating table, that a too large dildo can cause and anal fissure which is a tear in your colon and with the stuff that passes through there, it can get very infected and so painful that even Percocets did not help. After the surgery I had to make 3 visits to the Surgeon so he could stretch my anus back to normal size after the surgery which tightened it due to the need to cut out the infected part and then sex what was left together.

Online you read mostly fantasy stuff but I have been into fetish play for 47 years and there are real dangers. In porn a woman pegs her man with a very large and black dildo but in real life that will tear you a new one. Sure you can stretch with enough lube and there is no such thing as too much lube, but you can only stretch so far the first time. It is like when men shake off a very large penis entering a woman by saying that if her vagina can stretch to accommodate a baby it can take a 10" penis. Not really true since the woman has 9 months to stretch before birth and it is done gradually. Best bet is to buy a set of butt plugs that increase in size. They usually come in three sizes. Work your way up to a larger dildo because more lube makes it easier but does nothing to make your anus stretch.

 

Some very wise words above

 

Wow @Vinny that's intense.

Just really go slowly, as has been said. If a dildo hurts there's no way you should be considering a larger one yet. I'd even advise first getting comfortable with a smaller dildo than the one you're currently using. Seriously you can hurt yourself going too fast here.

What's helped me a lot in the past is making sure I'm extremely relaxed before any anal. Having a drink or two seems to also make me more able to relax. What kind of lube are you using? Water based lube tends to dry out quickly and get absorbed, so try something else just make sure it's safe for your toy.

Finally, this is going to sound gross, but I can take a strapon very easily if I try to "poop" as it's going it. Obviously, as before any anal play, make sure you're well evacuated before doing this. That muscle motion relaxes my anus a lot and makes it much easier to put something in. Last time I was pegged was one of the best I'd had. I asked my KH to lie on her back with the strapon. Then I lubed myself well and very very very slowly lowered myself onto it. Like 10 minutes of just really slowly fucking myself, going slightly deeper with each stroke. Then once it was all the way in I could move up and down slowly. As time went on I became more and more relaxed and she could start to thrust gently as well. Once you're relaxed enough, she'll be able to fuck you harder and harder. Just remember it will take time. Talk about it, set expectations, and set aside like an hour to just experiment gently with it.

And if it hurts, STOP. You cannot just "get over" the pain with anal. If it keeps hurting, stop and try again later. Your body is talking to you, and the language is pain. Don't ignore what it's saying.

 

I love anal. But here's the problem with anal no matter how much lube you use....your muscles are designed to push stuff out and that's it. So when you first begin penetrating yourself, your anus has this clinching reflex if you go in or out too fast. That clinching of your anus causes friction which is the enemy; no amount of lube can help you here ultimately. So you have to start out nice and slow and focus all your energy on staying open, staying relaxed, not letting yourself reflexively clench. Pushing out or pooping can have a relaxing effect as it's the opposite of a clench, but I wouldn't push too hard because you'll then be pushing against the thing trying to penetrate you. There's just this relaxed balance you have to find. Start out slow and small and use lube and work on staying as relaxed down there as possible.

 

Also here's my experience with finding the right lube.....never used silicon because of the toys o own so can't say necessarily.

But my problem with water based lubes has always been that they were too runny. Once they gunk up a little they have more substance to them, but starting out it's almost like trying to use water as lube (entirely) depending on the material the toy is made out of (chemistry is crazy). So I experiment with other things like lotion etc because it was thicker.

Here's what I found. Lotion is fucking nice if all you want to do is stick a finger up there and do come hithers toward your prostate. It's thick and feels really good but it's almost too thick so it gunks up fast and doesn't make good for in and out sliding motions.

At first I tried a combo of lube and lotion on the toy to balance out the thin/thick problem and that worked okish. But then I tried spit one time. I know they say not to use spit, but it's literally the best lube bar none. Its watery and luby but yet has a slimy thickness to it that makes it perfect in consistency. The ONLY downside is that it doesn't last super long so you have to keep reapplying and eventually you can't because you run out and your mouths dry. So to overcome that problem what I found was that if I lubbed up my toys with lube first and then added a nice layer of spit on top of that. Literally fixed the problems I was having with my lube and my toys feeling "sticky" even with a shit tonne of lube.

 

If I were you I would start by finding a feeling of pleasure anally that you do like and then trying to work off that. So start by yourself and use either some spit or lotion (completely serious about this and this choice in lube is important in my opinion) on your middle finger and just insert it and try doing sloooow in and out motions and come hithers and things like that. Then if that feels good work up from there.

P.S. the lotion really will feel good if all you're going for is prostate massage type stuff and not in and out fucking

 

Maybe try a few diffrent positions that might allow you to relax or at least open up a bit more, but like people have said take it slow x

 

It sounds like you need to take anal training seriously. Vinny suggested buttplugs, which is great! But if anal doesn't come naturally to you, you need extended training if pegging is her will. As in hours of wearing plugs before any fucking, and gradually working to where a bigger plug can be selected as the default.

 

OMG, makes you stop and think before doing anything....hope you're OK now....I can't begin to imagine how you felt telling the doc for the first time