Anal play

You could have a lot of intimate fun buying dildos of all sizes and having him use them on you. Over time, you will adapt and be able to take larger and larger things in your ass without pain. At one time, I could only take a finger or so. Now, fifteen years later, I have taken dildos two and a half inches in diameter inside me. And, yes everything still works properly back there.
 
I have let my partner have anal sex with me 3 times now, and I would like to be more receptive to him. He's always very gentle and respectful and careful. I want to make it easier on us both

He suggested an anal trainer but I am completely clueless. Where do I look? Is it something you put in and leave in?
He should, with you participating, be researching this together. Go on line, find toys and “anal trainer” together.

Posters above have made several suggestions. Start with plugs, wear them, slowly and gradually build up to length and girth.

He needs to work you up, lube, fingers, stretching, working you up, stimulating you, making you forget you have something up your bum, making it about you, pleasing you, distracting you from the intrusion that is his cock….

It should be something a couple explores and enjoys. Not one sided.
 
There are also instructional videos on anal play. Not dry since they usually have scenes but also go into the techincal details porn ignores.
 
Use lots of lube. And very viscous lube that stays. Silicone or silicone hybrid is probably safest for most toys.
I have steel plugs so I use a petroleum ointment as a lube for anal.

As liliput1 mentioned becare about the toy shape. Especially if you when you begin to lengthen the duration of play time. Removal hurts.
 
Just put it in later in the day. Try for about 30 minutes to start, and build up. But yes, just go about your evening. You could even wear one when you go out, my wife does it occasionally, only telling me when we're out
My wife will wear a plug from time to time when we are out on the weekends as well. I’m in the habit of checking the drawer where she keeps them while she’s getting ready to see if one is missing. I like to what the evening has in store
 
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