A: The first piece of advice we can give — and we tend to approach all new sex toys this way — is to start out on the frugal side. While that gold-plated plug (with matching cufflinks!) may be awfully tempting, it may not actually be all that comfortable or stimulating, in which case you’re looking at a considerable sunk cost for something even the shadiest Cash-4-Gold storefront isn’t going to take off your hands. Fortunately, there are plenty of options under twenty bucks to get you started, like the Li’l End ($16.99) or Love Pacifier ($12.99 and a personal favorite of future Mr. paperispatient, who is the butt plug expert of the two of us).
Another rule of thumb for anal play is to start small, as you probably know, and this works out nicely since most of the smaller/slimmer models available also tend to be pretty inexpensive (as long as they’re not, you know, fucking gold-plated). For a slightly larger investment, anal “starter kits” are available, featuring three or four different size plugs and dildos to start small and work your way up. Doc Johnson even makes an inflatable anal probe that makes it that much easier to achieve the just-right size without having to go all Goldilocks on multiple toys. There are also sometimes different sizes of the same toy — so, if you find that you love the smaller Love Pacifier, you might consider the “advanced” version of the toy if you’re looking for something a bit more filling.
Now, anybody can (well, in theory) use any kind of butt plug, but some of them are designed with different things in mind that might sway you and your boyfriend in one direction or another. The rounder ones and the straight, slim ones are mostly meant to provide that “all filled up” feeling that many people find pleasurable. Plugs that are curved slightly are usually designed with prostate stimulation in mind, and, as always, there are even vibrating butt plugs, if that tickles your fancy. Regardless of the specifics, any butt plug you try ought to have a flared base or a much-larger handle or something that will ensure that it only goes as far inside your ass as you want it to, and make sure to check out the material to see how to clean it (unless you’d prefer to use condoms over it, which is another option) and what lube(s) you can use it with.
So now you’ve got a great butt plug or two to try, what do you do with it? Well…stick it up your butt. (How often do you get to say that in the context of actually giving somebody advice? I had to.) Since the two of you have some experience with different kinds of anal play, you probably know all about lube, how quickly or slowly to take the penetration, and so on. People sometimes use butt plugs to help get them ready to receive anal penetration from bigger things, like a penis or strap-on or fist. Butt plugs can also be inserted and left in during whatever other kinds of sex you’re having and removed when you’re finished. Your ass is a pretty sensitive body part, so having something providing some constant stimulation in there while you’re having other kinds of sex can be extremely satisfying and, sometimes, orgasm-enhancing for some people. You’d probably start out with a bit of fingering before moving on to the butt plug, but how much working up to it you’ll have to do really just depends on you and your bodies and the size/shape of the plugs.
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