How do you play with butts?
January 4, 2014 4:43 PM   Subscribe

I am a straight male with a NSFW sex question under the fold.

I am in a relationship with a girl that I've been dating for several months. Recently we've started exploring our kinkier sides. One thing that was brought up by her was the idea of anal play on me.

I have complicated feelings on the subject. I feel open minded towards trying it, but I'm not exactly eager to do it either. I kind of view it as something different to try and if I don't like it I will know it's not for me and don't have to do it again. But I'm also kind of scared/anxious by the thought of it and there's a lot I don't know.

Generally I view anal sex as icky. I've never stuck my finger/penis in someone else's butt. I've never stuck a finger into my own butt. I'm slightly curious to try anal from a giver perspective, but I've never done this either nor do I feel a strong urge.

One last thing. I have a very difficult time orgasming due to antidepressants. I'll have sex and it's fun, but I won't cum. I just eventually lose interest. I was wondering whether prostate stimulation got around antidepressant-induced anorgasmia.

With all that said, please educate me. Tell me everything I should know.

posted by anonymous to Human Relations (21 answers total) 4 users marked this as a favorite
I would recommend starting small. Literally.

Just... put a finger in. You or her, pitching or catching, either way. Lots of lube. This is one of those things you can totally just try on the spur of the moment, and see what you think of it. If you like it, keep experimenting and see where it takes you. If you don't, whatever, so somebody stuck a finger in your butt once, it's not like a life altering experience or anything.

Lots of lube.

Lots of lube.
posted by Sara C. at 4:57 PM on January 4, 2014 [5 favorites]

Yes, lube. Also, trim nails. A glove or condom might help too, particularly with the ickiness.

Men have lots and lots of nerve endings there and I wouldn't be surprised if this helps get you off.
posted by PhoBWanKenobi at 5:09 PM on January 4, 2014 [1 favorite]

Shower and clean yourself out first. Use way more lube than you think you need. Your prostate is up there and holds many delights upon stimulation. (there are many resources for 'how to stimulate your boyfriends prostate in a way that is pleasurable' on the web). Relax, go slow, and make sure you feel comfortable saying either 'i like that, can you do it some more' or 'eh im not really feeling this'.
posted by softlord at 5:18 PM on January 4, 2014 [1 favorite]

Trim nails. Lots of lube. Go poop before bed! Have a sexy shower together.

Did I mention lots of lube? Lots of lube.

But before needing any lube, since you're both fresh and clean from your sexy shower, start trying with just rimming (each other or one way or whatever). Forget trying penetration for now, just try rimming and see where that leads you. If you decide you want to be penetrated at the time, great, but don't be thinking of it as a goal to get to.

Throw the occasional rimjob into the mix when you two are doing your thing, and see how it works. On the receiving end it's a lot more gentle than a finger, much better for easing your way into things. You shouldn't be terribly concerned with any ickiness right out of the shower, but if you are, dental dams are good. And very easy to fabricate one, just cut open a condom. (Unlubricated! Lube tastes like sad.)

If you're both comfortable with that level of playing, start with gentle manual stimulation around the anus. Actual penetration should be very slow (use lots of lube!), and two-steps-forward-one-step-back is a recipe for avoiding pain and discomfort. A glass or two of red wine (or other preferred intoxicant) can also help with relaxing. But a little! Feeling a nice warm glow about the world, yes; sloppy drunk, no--your pain receptors don't fire the same way and you can easily wake up rather more sore than you'd planned.
posted by feckless fecal fear mongering at 5:21 PM on January 4, 2014 [1 favorite]

Try starting with just gentle manual stimulation around/over, but not into, the anus. Like a rim-handjob.

Something else that helped get me over the ickiness: hand sanitizer and antibacterial wipes. If you feel the need, it's easy to clean your hands and nails immediately afterward and then get back to other kinds of sexy time.
posted by serelliya at 5:51 PM on January 4, 2014

I'm a straight dude. I'd say don't start with a finger if you're feeling a bit icky about it. Go to a sex shop and buy a butt plug the size of your index finger and some lube. Try it alone first to figure out how it feels, then let your gf try. Latex gloves take a bit of the romance out but might help with the ick factor. Have fun, it's definitely worth it.
posted by no regrets, coyote at 6:32 PM on January 4, 2014 [1 favorite]

Start by sticking your own finger in your own butt. Take the mystery out of it. Maybe then try sticking your finger in her butt. And then getting her to stick her finger in your butt. But I don't think rimming and butt plugs are really the first place to go if you're not sure/grossed out about the whole thing.
posted by heyjude at 6:41 PM on January 4, 2014 [6 favorites]

Well, if she's cool with it, maybe let her start with the touching. I would say finger first, since you've got 'em right there in a variety of sizes and they can vary pressure and placement so easily. Let her play around your taint, etc. the way she wants, since she seems to have more of an idea than you do, with the express caveat that you get immediate veto power but will be GGG as much as possible.

I personally consider rimming to be a step too far for me, so I wouldn't dream of starting with it, but ymmv.

You can get a lot of pleasurable sensation with pressure on and around the anus without penetration. Stick with that for a while, at least until you realize that it feels kinda good and maybe going past that wouldn't be terrible.

Do not overestimate what you will be able to handle. If you get a plug, get a nice smooth one that is basically finger-sized. Do not say, "Oh, I'll fit the walnut-sized thing after one time." Possible, but NO. Do NOT.

Lube for butt stuff tends to have a thicker consistency than other lube. Your friendly local shop probably has a goodly number of samples, but a nice plain one to start with is Maximus. It's clear and water-based, made by the Liquid Silk people. They sell it in 50ml bottles that aren't cheesy-looking and won't be super obvious next to the bed :)

If you want to do penetration, it helps to be super relaxed, so maybe start playing after you've come at least once. Get very comfy on your surface of choice.

Really, you will have more nerve-ending options than your lady friend. This really is an opportunity for her to give you some cool pleasure, what with your prostate and all that (which she can also put pressure on without penetration). Don't be shy about saying that something is or isn't working for you, even if it's just "eh, this isn't painful but is just weird and not really doing it for me."

Have fun!
posted by Madamina at 7:08 PM on January 4, 2014 [1 favorite]

Congratulations - ass eating is possibly the last great American art form.

Hit the shower with your lover, get both of your behinds all cleaned up, and relax and get your ass eaten/eat some ass! No need for neophytes to move to penetration immediately; just get her/your tongue in there for an unforgettable experience. Unless you've been kidnapped from a nursing home, there are no worries about an unsanitary session with your lover. You won't regret it - start slow and have fun!
posted by porn in the woods at 7:39 PM on January 4, 2014 [1 favorite]

I'm also going to suggest you get a toy and use it solo first. I think associating anal play with pleasure is an important step before you dive into the power play stuff inherent in being penetrated, particularly as a straight male in this culture. And it might take some time. I will say I'm a straight male and I find the pleasure from prostate simulation to be at least on par with penile stimulation, and together it's really amazing.
posted by MillMan at 7:41 PM on January 4, 2014

In addition to the very good advice here, I'd like to stress how important that it is for you to talk openly and honestly with tour girlfriend before dipping your toe in the anal pond. Good sex is about good communication, and good anal sex (for your or her) will take time, patience, and lube.

If I'm reading your question properly, your girlfriend seems to be more into anal play than you are. Why not ask her what excites her about it? From there, I'd recommend asking her to find examples online of what she had in mind. Tumblr is very good for this--it doesn't matter what your fetish is, there's a Tumblr blog for it! Take it slow, and talk it out before she even gets near your butt.

Also, I wanted to respond to the last part of your question (about antidepressant induced anorgasmia). Speaking as the owner of a prostate and the owner of a special device meant to stimulate it (it's called the Aneros, if you want to look it up), but not speaking as someone who is on SSRI's, I can tell you, frankly, that prostate stimulate can be pleasant, but it's not like you have a secret, hidden clit up your butt. If the feeling of "fullness" when you have to go to the bathroom is not sexy, then it's unlikely that having your prostate massaged will make your come despite your medication.

You sound like you are unsure if you even want to try this. My best advice is to find out why your girlfriend is interested, and let her know that you are interested in pleasing her. You might be able to give her some of the thrill by talking dirty, watching porn, or just openly and honestly telling her that what turns her on is important to you, even if it's not your thing. Good luck!
posted by Mr. Fig at 7:45 PM on January 4, 2014 [4 favorites]

Anal beads...vibrating or non-vibrating. These can be had for like $6-$10 at any local sexy time store or on amazon. Lube. So much lube. More lube that you think is realistic. Go slow.

My suggestion would be to work those beads in a couple inches and find your prostate.
posted by fluffy battle kitten at 7:45 PM on January 4, 2014 [1 favorite]

The ass is not nearly filthy as you or most people think. Your intestines are not jam packed with shit from stomach to sphincter. You are not a chocolate soft serve ice cream machine dripping shit. So, relax!

You are a potty trained adult. You know when you have poo on deck. Lube up your finger and check it out. Stick it in with your palm facing you and make a come-hither motion. That pleasure button is your prostate. It is your second penis. It is your poor, neglected second penis waiting to get some action.

Toys are tricky. Most sex toy shops have absolute garbage in them. Toys made out of toxic materials because they are unregulated. I also think finger sized toys aren't worth it. But, as most people like to start smaller than they can handle (you make poos four times the width of your finger no problem). I would get an Aneros. They have a great design for hitting that prostate from simply walking around, sitting down, or taking up the real while you fuck your girlfriend. It is made of body safe material and of a size that won't scare anyone off.

Lube, lube, lube. Take it slow. No poppers or numbing creams until you know what you can take.
posted by munchingzombie at 7:57 PM on January 4, 2014 [8 favorites]

Don't use water based lubes, they suck! Try silicone or oil based.
I love coconut oil.
posted by Sades at 8:00 PM on January 4, 2014 [1 favorite]

Let me recommend a friend's book, if you'd like to read more on the topic: The Ultimate Guide to Prostate Pleasure.
posted by gingerbeer at 10:17 PM on January 4, 2014 [1 favorite]

Re: rimming. Don't use the "flattened condom," go to the kitchen and get the roll of Saran Wrap. Way more fun that way.
posted by halfbuckaroo at 2:49 AM on January 5, 2014 [1 favorite]

I have a straight male friend who likes anal penetration, owns a bunch of stuff including an aneros. When he was experiencing SSRI-induced anorgasmia, the anal stuff didn't help him. Sorry. It's entirely possible that YMMV though.
posted by Lebannen at 3:32 AM on January 5, 2014

Nthing lube, gloves, and communication. You can also use those rubber finger covers found in the drugstore near finger splints.

Ducky Doolittle and Tristian Taramino have stuff online about anal play.
posted by luckynerd at 10:07 AM on January 5, 2014

Butt sex feels awkward and embarrassing at first, but is totally worth it.

I highly recommend trying to touch your own butt a bit first. The shower, or after a shower with some good lube is good. If you can reach your butt hole, just try touching it gently, circling it, tapping it, while you watch porn or masturbate or just think pleasant thoughts.

If one of you has a vibrator, try putting the vibrator (wrapped in a condom) against the outside of your butthole, just to get a feeling for it.

The shower, using soap as a sort of impromptu lube, is also a nice introduction to playing with a partner. You guys can both play with each other's butt holes without actually penetrating each other - just play in and around it with your finger (or, if braver, your mouths).

For penetration, wait till you're already aroused, and then, with a lot of lube, try just one finger. I find that at first it helps to just put the finger in part way, then just leave it there for a while while you do other arousing stuff, rather than going right into an in-and-out kind of action. If the size of a finger starts to feel good, you can eventually work up to two fingers, toys, etc.

Don't be afraid to use latex or nitrile gloves (when you're not in the shower - they don't work very well when immersed in water). A dark color glove takes away some of the ick fear. You can remove the glove when you're done by turning it inside out -then no one has to think about what might be on it.

Speaking of that, try a time of day not long after you've pooped. Then your butt is probably going to be empty anyway. Really, the poop thing is much less present than you'd think.

Do check out some of the books and other resources recommended here, and good for you for pushing your own comfort zone and trying something new!
posted by latkes at 7:26 PM on January 5, 2014

using soap as a sort of impromptu lube

Soap is terrible lube. It burns mucous membranes. You DO NOT WANT a bunch of soap up your ass.

Don't ask me how I know this.
posted by feckless fecal fear mongering at 8:47 PM on January 5, 2014 [1 favorite]

Ha, fecal fear mongering indeed! A mild, natural soap with no additives is no big deal and works fine for not-too-vigerous action in my experience.
posted by latkes at 9:29 PM on January 5, 2014

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