I was in the same boat as yourself @TheExplorers probably 3 months agoā¦
Always wanted to try but never actually done āitā so to speakā¦
Me and the OH @Steffi.O bought the smallest plug we could find on here,
And by myself, with some words of encouragement from her at various times prior to the āsolo eventā. I took all the advice I had come across from here and set about giving it agoā¦
First impressions were mixed, as it felt foreign and just made me feel like I was about to poop lol.
I just left it in and layed on the couch, feeling rather awkward for about 20mins or so, then came removal timeā¦
I panicked and took a few minutes to get it out, just had to take a deep breath and relaxā¦ I also pulled out quite a few hairs back there in the processā¦ so +1 for removing the hair around the areaā¦
Fast forward those 3 months and I now enjoy various sized plugs for extended periods of timeā¦ and am looking forward to bringing pegging into the bedroomā¦ Just not quite there yetā¦
As for position I just lay on my back on the bed legs open and knees bent up towards chest, apply lube to the toy and the excess to myself, get the front end excited and just massage the area with the toy, going in and out a little more each time until my body accepts the toy,
You can feel once your past the biggest point and your body just slides the rest in, itās quite a nice feelingā¦
Sorry for the long winded post but I thought that information would be helpful 
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Position wise, on your side knees up toward your chest is a really good one (think foetal position and its a bit like that). Makes it alot easier to access and get things in and its my go to the majority of the time.
If you want to insert it standing or kneeling, bend right over (think doggy). Makes it alot easier.
If these arent comfy for you, You can also do it on your back with a cushion under your hips and your knees bent. Or sitting up curled forward with your knees up. But i would recommend trying it on your side the first time.
Deep breathing in and letting the air out nice and slowly. Especially as your inserting is really good for helping you not tense up. What really helped me the first time was getting into the mind set of really wanting the plug in. Try and focus on how good it will feel. How much you want that. Can help alot with any nerves.
As youāve picked a vibrating one, you could just use the vibrations externally to rim yourself the first couple of times. Let yourself associate the toy with feeling nice and relax more about playing back there.
Also lube. I know everyone will say this to death but buy anal lube and apply it to the area as well as to the toy. dont be worried about putting too much on, making sure everything is nice and slippery will give you a better experience.
Like everyone said, first few times it might just feel strange, so persevere.
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@TheExplorers Like most everyone has said the knees up is a good, relaxed position. If I read your post right you said youāve not ventured with a finger yet but I think that is the best starting point. It gives a better feel to yourself and the toy, while fun, will take getting used to the āhandlingā if that makes sense. Definitely a lot of Lube, tease with a finger, then slowly insert. This will give you a good sensation and better direction for being āon targetā when a toy is used. Have fun!
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Buy toys for prostate stimulation. Itās curved to put pressure on prostate & will definitely be a greater orgasm. Iām straight & it doesnāt mean youāre bi or anything. If you are or anyone here is bi or gay then they already know what Iām talking about. Good to be open with yourself & sharing. People on here are all very supportive & open minded. Glad to be amongst great people