Dildo
He will relax into it but it will take some time. — make sure you get equipment that's going do something for you too.
This won't do a lot for you physically, but may be a huge psychological turn-on. Take advantage of it by finding a vibe you can use, during, so you can both completely lose it together. For anal beginners, you have to be in the RIGHT positions to make it work. DO NOT put your boyfriend into doggy-style.
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It may seem straightforward, but strap-on harnesses come in a variety of different styles and can be a bit tricky to put on. You'll want to pick what's right for you, which can only truly be done by physically going into the store and trying one on. Going into a sex shop doesn't have to be intimidating.
Give him a little swat every once in awhile to remind him exactly what's going down. A rare man can come with anal stimulation alone, but most men won't, so when he's ready finish him off by turning him over.
Be sure to read the directions on your dildo to see what kinds of lube will work best. It's thicker than other water-based lubes, which helps the dildo stay lubricated. You'll also need to buy O-rings, the round pieces of plastic best strap on that go in the opening of the strap-on to hold your dildo in place.
Make sure the dildo is always facing away from your boyfriend's spine, toward the bellybutton, to ensure prostate stimulation. This direction will depend on the position, but it should be pretty straightforward based on general comfort.
And when it comes to anal, the more lube the better. If you think you have enough lube, just add some more for good measure. It's messy, but it's better than a painful butt-sex experience.
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