Help a gal penetrate her guy!
January 10, 2014 9:55 AM   Subscribe

I'm a hetero female. My boyfriend wants to experiment with anal penetration (for him). I'm definitely up for it (hooray for new sexy fun times!), but have zero experience in that area. We have been playing around with low key/shallow/tentative anal penetration with fingers, and he DEFINITELY likes that, but he'd like to up the ante with toys and deeper penetration. Where to begin? What are your fave toys? Any anal-specific hygiene/safety things we need to be aware of? Other things we need to know before embarking on this adventure?

Like all things sexy, I know that most of this learning/fun-having process will come down to play and experimentation and finding out what we like through play, but sex toys are overwhelmingly varied, and my budget is modest (i.e. I can't buy one of everything and try them all, though what fun that would be!), so I'd love some suggestions about where to start for a lady penetrating her guy for the very first time...

Our current sex toy arsenal is very small (I have a large rabbit-esque vibrator that I use for me, and a small bullet-type vibrator that doesn't get a lot of use at the moment), and both of our experiences have been pretty vanilla up until now...

Help the boy and I become master butt players, sexy MeFites!
posted by anonymous to Human Relations (12 answers total) 8 users marked this as a favorite
You'll get more and better answers if you set up a throwaway gmail account.
posted by pupsocket at 10:24 AM on January 10, 2014

"Any anal-specific hygiene/safety things we need to be aware of?"

Flared bases. You don't want anything that can get stuck.
posted by colin_l at 11:17 AM on January 10, 2014 [1 favorite]

Just some random suggestions.

Lube, lots of lube, no more lube than that, I like to use lube aimed at gay guys as I figure they know what works best for anal don't try and save money here. Go slow and steady. Butt plugs can be found pretty cheap if you shop around and can come in smaller sizes and you then don't have to worry about fingernails, rough skin and the squirk factor as much. I would suggest not starting with a strap on as it's so much easier to make things slow and gentle if you can see what you are doing, but you can get strap on's at a later stage that you can fit the butt plugs you bought earlier into thus saving some money.

Vibrating butt plugs in small sizes can be found in about the same price range as a bullet vibrator, the first time I did anal on a guy using one of these he couldn't speak for a while after and just sort of mumbled incoherently with a goofy grin on his face. I like the ones with a cord to the controller as trying to adjust speeds on one while inserted and covered in lube is a pain.

You can get cheapish begginers kits like this which while the toys aren't great quality would give you a place to start with experimenting, so you can work out what you guys like before upgrading.

Be aware that poop happens, I like to have a tonne of wet wipes near by and a couple of towels around/under for easy clean up if nothing else. Wash all toys really well afterwards, I use a sex toy cleaner. Get him to shower before hand is nice too. You sound like you both have a good attitude to experimenting which I think is the most important thing.

Oh I just found this guide which you might find useful. Not affiliated with the site in anyway it's just the first one that came up in my google search.
posted by wwax at 11:29 AM on January 10, 2014 [2 favorites]

Oh, yay for you -- how exciting!

Okay, safety first. Avoiding injury: Use lots of lube and go slow. Butts don't self-lubricate, so you'll need to apply lube to your toys, apply lube to the anus, and then probably pause every once in a while to apply more lube as you go. You'll also need to go really slow at the beginning to avoid injury -- like, a hair's width every breath type of slow. If it hurts, use more lube and go slower, because it shouldn't.

Hygiene: Don't swap toys from the butt to the vag without cleaning -- anal bacteria can do a number on sensitive lady-bits. After playing, wash your toys with soap and water, then disinfect them in whatever more hardcore way the toy suggests (such as boiling). Buy high-quality toys; you don't want something that'll leech toxic stuff into your tender membranes, or deteriorate when you combine it with condoms or certain lubes, or be so porous that it's hard to clean. Respectable places like Good Vibrations, Babeland, or Eden Fantasys will list info about the toy material so you can make a good call.

Where to begin: Start small! Get some anal beads and a butt plug (they have really different sensations, so he might like one more than the other). You want something that will help stretch at small increments. Try getting beads that start really small, and end at about the size of halfway up the plug, and a plug that at it's widest is close to the size of the dildo you'll want to eventually use, so the transitions are more gradual. Let your guy play with the toys himself a bit to figure out that part of his anatomy, so that he can more easily communicate to you how to help make him feel good with the toys.

Also, start slippery! Invest in some nice lube that won't dry up with friction, won't mess up your toys, and won't sting. (I can't imagine anything better than Boy Butter, because it lasts as long as oil-based lubes but with the easy cleanup of water-based lubes, but there are lots of choices out there.)

Deeper penetration: Eventually you'll want to move up to a dildo or strap-on, but dude, there is so much variety in what people want out of their penetration, it'd be like me trying to tell you what kind of puppy you should get. It depends on what experiences you guys are looking for! So, memail me, I guess, if I haven't yet sufficiently talked your ear off regarding this.

Other things: Have some wet wipes and washcloths nearby! With the amount of lube you'll be dealing with as you learn what you guys like, having something to wipe your hands off on nearby will be handy; and wrapping a messy toy in a wet wipe makes clean-up easier later. And, speaking of messy: you're dealing with a butt, so there's always going to be a chance that you'll interact with poop. Make sure you guys are in a comfortable enough place that this won't be weird -- be able to help clean up, be comfortable suggesting a quick shower before getting back to business.

Communication in general is basically the most important thing here. During the going-really-slow stages especially, you'll both need to pay intense attention and let eachother know how things are feeling. I think consuming casual culture that is related to sex is a great way to normalize open and free discussion of this stuff in your relationship, so if you ever falter there you guys can read Savage Love columns together, or Oh Joy, Sex Toy, as examples. I don't really anticipate you guys having problems here based on how you phrased your question, but it really does make or break a sexual experience. Have fun!
posted by Pwoink at 11:39 AM on January 10, 2014 [3 favorites]

For toy suggestions, I highly recommend going with a 100% silicone toy. Silicon is non-porous, odorless (for the most part), hypoallergenic, and can be safely boiled or ran through a dishwasher so as to be sanitized. Use only water-based lubricant with silicone toys (or place a condom on it). I would start off with a smaller size - roughly 5 - 6 in. with a definite 'base' that will prevent it from sliding in entirely. Personally, I'm a fan of VixSkin silicone toys. They're 100% silicone but have a realistic texture/firmness/feel that you can usually only find with rubber toys. They can be used with a harness or without. They are kind of pricey, but I've had mine for 8 years or so and it's in just as great condition now as it was brand new (Note: cleaning the toy immediately after use and keeping it stored in a cool, dry, dark place is likely the reason for it's longevity).

As for the act itself. Go slow...lots of lube. Tons of foreplay beforehand, explore with fingers, then work your way up. Ideally, you'll be able to stimulate the prostate - when inserting fingers, curl them towards his anterior (front/stomach) and you should feel a slight bulge -- stroking and gently pressing here should be very enjoyable for him. Be sure not to spend -too- much time here, as things will get sensitive or it may be too much for him.

Also, don't expect him to maintain an erection the entire time and don't use it as a gauge to determine whether he's enjoying himself or not. Despite not having an erection, continued touching and penetration will likely be very pleasurable and some guys are capable of climaxing without being fully erect.

My final bit of advice is making sure you're both very open with your communication during the actual act. He should be comfortable telling you to go slower, faster, back off, ect. without worrying about hurting your feelings. Likewise, you should be able to -ask- him what he wants without feeling silly.

Make sure your boy is 'clean'. Your nails are clipped. Your hands are clean. Toy is clean. Lube is plentiful/readily available. The space is comfortable and clean up towels are always within reach.

Have fun!
posted by stubbehtail at 11:52 AM on January 10, 2014

"Lube, lots of lube, no more lube than that, I like to use lube aimed at gay guys as I figure they know what works best for anal don't try and save money here."

The advice from a gay friend regarding buttsex for ladies was, "Use twice as much lube as you think you need, then add more."
posted by klangklangston at 1:06 PM on January 10, 2014 [1 favorite]

The book you want is Anal Pleasure & Health by Jack Morin. And it even looks like it's back in print!
posted by Amplify at 1:53 PM on January 10, 2014

I haven't watched it, but I've heard nothing but raves for Carol Queen's Bend Over, Boyfriend video.
posted by rmd1023 at 5:20 PM on January 10, 2014

colin_l touched on this already, but as an EMT I think he was insufficiently explicit. When he says "you don't want anything that can get stuck," what he means is, "you don't want anything that can penetrate deeply enough that there's not enough left sticking out for you to get a good grip to pull it out, because then you will have a rectal foreign body and you will have to seek medical attention and although everyone will behave professionally you will (probably) still feel humiliated."

Also, if you do get something stuck in your rectum, please seek medical attention immediately. And don't lie about why you've presented yourself to the ED, because no medical professional will pull anything out of your rectum unless you ask him to.
posted by d. z. wang at 8:16 PM on January 10, 2014 [3 favorites]

Keep clean.
posted by oceanjesse at 10:10 PM on January 10, 2014

sex educator here. just want to add to all this great information that I suggest to folks I talk to about exploring anal sex that they avoid any products offering "desensitizing" or "numbing" of any kind. they often contain nasty chemicals. there should be little to no pain if you use plenty of lube and go slowly. these desensitizing agents also block vital body feedback information. you really DO need to feel if there is any pain or discomfort because often that's the signal to stop, lube up, and proceed again slowly.

Tristan Taormino is a wonderful sexual health educator who has several books and DVDs on pegging. She also has an on-line salon of sex positive information called PuckerUp.

There are a small network of woman-owned sex toy stores across North America that are part of the Progressive Pleasure Club (PPC). Look to see if one of the stores in the network is in your area and be sure to consult with folks there if you have further or more detailed questions.
posted by kuppajava at 8:58 AM on January 13, 2014

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