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I started with this little wonder. https://www.amazon.com/Icicles-No-2-Blown-Glass-Massager/dp/B003YIKUI2 Affordable, lets you get a feel for the whole experience, and you can work up your comfort level before moving on to bigger and more expensive options. I would not start with bad dragon. They are expensive and you can easily get in over your head. Only other advice is... lube and clean your toys religiously.
Lots of great advice in here and I'm late to the party, but a toy suggestion that might help: something like this. It's more graduated than the plugs you're trying to work with. I think it's one of my best purchases ever. Good luck!
hello a hetero sexual guy who anal masturbates here. i can give you a few tips which works for me. it requires you have the night alone or the day alone and at least 4 hours in the begining. some toys i use that helps is the icicles no2 which has one big end of 1.4 inches /2.8 mm. and the other end is small like an pinkie to help you get used to the penetration. an other plus its glass so any lube works. second i can recommend is an buttplug called the regenade pillager. now to the issue you have here tough. to get over the uncomfortable feeling you can either use the icicles with the small end and make small movements, it will feel uncomfortable at first.
,keep doing these small movements with this toy and feel each bulb stretch you up let it take some time maybe 30 minutes, just use small movements until will feel the feeling becoming enjoyable. when you start to feel it enjoyable begin to increase the movement with the toy. you can do this backwards to with the toy to by begining with the large end . when you have increase the movement so you feel really loose then, you can start to penetrate fast untill you reach the desired orgasm.
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here is an link to the toy how it looks like i recommend to buy it from a local shop
https://www.amazon.com/Icicles-No-2-Blown-Glass-Massager/dp/B003YIKUI2
https://www.amazon.com/Renegade-Pillager-Silicone-Pleasure-Black/dp/B07CNHNVCD
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some lubes i use are like water based thick lubes or coconout oil based hand creams. one without parfumes or any extra ingridents.
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sorry for bad punctations or bad typing.
If you've not browsed adult shops much before you might be surprised at the vast range of toys available in a multitude of sizes and shapes. First thing to do would be to decide what you'd like the toy to do and then find the toy, or toys if you have the budget, that fits the criteria.
For a guy like yourself I might recommend considering a glass dildo with graduated beads, something like this or this. It'd combine the benefits of a dildo and anal beads in one, let you practise stretching and hopefully enjoy sliding it in and out as a dildo. Ideal foreplay toy too.
Using condoms with toys makes virtually any easy to clean but glass ones don't even need that since nothing can get absorbed by the glass, so soap and water do fine.
Icicles No. 2 was the thing I thought of, but you couldn't really attach it to a machine I wouldn't think. Link to it anyways:
http://www.amazon.com/Icicles-No-2-Blown-Glass-Massager/dp/B003YIKUI2
edit: not anal safe
I know you wanted recommendations for butt plugs, but I have this glass toy which works amazingly well at "warming you up" to be ready for a plug. The small end is about the width of a finger, so it goes in incredibly easy and you can work up to the larger rings as you're ready. When you're comfortable and ready for more, switch to the plug. My partner has a pretty big plug and we've found that using the glass toy first makes it much easier to insert the plug afterward.
Added bonuses that glass can be warmed up first (by body heat or warm water) and is easy to sterilize for shared use.