So me and my significant other try doing anal but every time it hurts for her. We have used butt plugs working up from small ones to larger and it still tends to hurt. What do you recommend? How did you go from hurting when trying anal to enjoying anal?
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Lots of lube. Not rushing.
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For me it just happened one day, I had tried anal with my ex but I didn’t enjoy it, but I had always enjoyed using a dildo in my ass. One day OH and I were going at it and and I asked for anal. Not only do I enjoy anal but it is now my preferred way to have sex. For me the big difference was when I tried it the first time with my ex I found the in and out sensation very odd and the whole thing very painful. Using dildos I could learn to enjoy that in and out sensation on my own and learn how to revive anal in a way that was comfortable for me. Maybe try a different lube it took me a while to find one that worked well for me.
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Relax, lots of lube and don’t over think it. Early in me and my OH’s relationship she wanted anal a few times and every time she said it hurt and was uncomfortable. I think from our perspective, was that even though we prepared, had plenty of lube we were too overly focused on it. We didn’t try for a long while when one day making love we were in a spoon position when my cock slipped out and when going to insert back in it hit her bum. Wife was excited and made a comment of “yes in the ass” put some lube on my cock and this time it went right in. I moved slowly making sure she was comfortable. That was the beginning to a sex life that is probably now 80% anal as she prefers anal over PIV.
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Loads of lube and just relax take it easy and go a bit slow at first
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Good advice. Putting a little inside may help too.
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Loads of lube
Train with butt plus’s working up in size
Go slowly it’s not a race
Play with the bum hole, tickle and finger it
Get in a relaxed position
Gently push in getting verbal feedback from the receiver
If it hurts stop! Go back to fingering and introduce more lube.
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After working up with fingers toys and lube take it slow as you slide it in. Pop in the tip and stop while she focuses on breathing then when she is comfortable slide in half way, again pausing to breathe. Once she is comfortable you can slide in all the way. Take it slow and if you need to repeat the process. My Mrs loves me telling her how much I’m enjoying it and how beautiful she is as I gently touch her body. We don’t do it that often but when we do it is a special treat for both of us.
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Great advice above the only thing I would add is maybe get you OH to give her self some clitoral stimulation at the same time, the more she focuses on that the more she may relax into it, and definitely lubed, slow and easy. I definitely found the higher the arousal the easier and more comfortable it became.
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It’s all been said - lube helps but she needs to relax - if she is concerned or stressed she will tighten up her anus and it will not work - have you used dildos as this may be a way to her anus getting used to larger things
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I agree clit stimulation will help the Mrs likes to use her bullet vibe. Relaxation is key.
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Are the larger plugs the same size as your penis? Anal needs a much slower motion than the vagina, it’ll be easier for her if she controls the pace. Let her back up on to you and reassure her in case she’s overthinking how how long its taking. Slowly slowly catchy monkey.
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I had to practice using a dildo for a while first
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What others have said: go slow, lots of lube
I hear douching works too to improve sensation.
For me a vibrating toy is awesome too
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I think it’s possble some people can’t do it 
she will need to learn how to relax …the first thought of pain and it will tighten everything up down there , just gentle breathing the same way you do when giving birth helps relax everything down there
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All good advice . But I agree with @Melody1 , get lube inside . Even though I am an experienced user of anal toys I start small and work my way up in size with each getting a good coat of lube . That is the only way I can take my biggest cock replica dildo at 9" and very girthy . Note dildos are generally much firmer than a real cock , so if given the right circumstance I would love to try several real cocks and and compare . Also would love to feel when they shot their nectar deep inside me .
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Try a specific anal lube, don’t rush, and be as relaxed as possible
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Start by using a smooth thin vibrator and insert it into her slowly - she needs to relax otherwise it will not work
As he learns to take this toy change up to a bigger / textured type as taking a man’s penis can be difficult- but without in the end
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I once read a good article online and it basically said anal isn’t always for everyone, you either enjoy it or you don’t and there’s no shame in either 
If she’s still eager to give it a try and experiment then I’d recommend maybe some anal lube what relaxes the muscles a little.
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