Before trying it out, I always thought anal sex was kind of taboo: like if anyone tried it, they would be considered a little sexually deviant. After some intense butt sex (are there any non-awkward, non-clinical alternatives to "anal sex"?), I began thinking of it as something that was very natural and that it was only really taboo because of cultural constraints. I mean, think about it.
For girls: if getting fucked in one hole feels transcendently orgasmic...then would it be too far of a leap to consider that getting fucked in the hole a mere inch or two away might yield the same results? This goes for guys too since the right butt plug (the Aneros has been widely hailed as the best prostate-stimulating butt plug around), dildo or penis will stimulate the prostate, the area that secretes 30% of the fluid that goes into cum (the other 70% comes from the seminal vesicles). For men, anal sex of any kind (on your own or with a partner or multiple partners) often comes with a lot more taboo than for women since females are often on the penetrating end of sex anyways. When men receive anal sex, they give up the power that we associate with the penetrator and assume the position of penetratee. "I would never try anal sex! I'm not gay." If you stubbornly stick to that way of thinking, you may be missing out on some of the most orgasmic sexual experience available to you: after all, the anus has the same nerve supply as the genitals and just like your pelvic floor muscles (aka PC or Kegel muscles, which create strong contractions during orgasm), the anus dilates when stimulated and contracts when you start orgasming.
All of that said, one of the best ways to begin exploring anal sex is with your finger and perhaps a butt plug. Anal sex is always best when you're relaxed and have a lot of time to explore. For example, in the shower, try inserting one or two fingers into your anus and see how it feels: you're probably not going to start cumming your brains out but this will help you get used to the sensation of having something go into your rectum instead of out. If you prefer to play with yourself in bed or anywhere that is not the shower, be sure to use lots of lube since the anus does not self-lubricate. There are two muscular rings (called sphincters) around your anus and they may start to contract and relax in response to insertion. You can experiment with moving your fingers in and out, perhaps curving them towards the prostate or G-spot. The thing is, though, unless you're pretty flexible, you may either be unable to reach these pleasurable centers or you'll be able to reach them but not comfortably. This is where toys come in.
Butt plugs are a great way of introducing anal toys into your realm of sexual experience, your sexual portfolio...whatever you want to call it. The best ones have an enlarged head so you can get that feeling of fullness and also be able to stimulate the prostate/G-spot. Be sure to get one with a flared base so that the toy doesn't travel up your rectum while you're playing around because that would turn your orgasmic me-time into an embarrassing trip to the ER. Again, use lots of lube on the plug; lube up your finger a bit and play around with your anus a bit to get it lubed up too. Slowly, whenever you're ready, relax and insert the plug, letting it slide in: for me, relaxation calls for deep breathing so I like popping it in during the inhalation. Once its in, you can:
- Experiment with moving it in and out a bit
- Masturbate and see how playing with yourself and orgasming feels different when there's something in your anus; I especially like doing this with a vibrator on my clit
- Just walk around and go about your daily life to get used to accommodating something in your anus (building up to sex). Plus, you'll feel a little naughty if you're at work or something, innocently whistling and going about your innocent day being your innocent self when really: you have a butt plug up your bum.
- Try oral sex or just plain sex while you have it in and experience bliss.
- Little Flirt: recommended for true first timers. It's super small and good for introducing something into your anus. It also comes in a bigger version called (surprise) Big Flirt, which also might be suitable for a first timer whose anus isn't as tight.
- Ace Plug: I love the feeling of fullness that I get from this one. It's small enough not to stretch me out too much but big enough to let me know its there. It's actually the slimmer, longer version of the Tristan plug, which I believe was designed by Tristan Taormino, butt-sex extraordinaire.
- Mars Plug: I haven't personally tried this one out yet but seeing as its made by njoy, the same company that I raved about in my fun wand post, I am painstakingly saving up to get one. I think this will be a great plug to wear while getting eaten out. Plus, its a work of art.