Anonymous: How can I make anal less painful?

Anal shouldn’t be painful at all. If it hurts, you probably aren’t ready to have anal sex yet and should focus more on anal masturbation/training before resuming anal sex.

Experiment with how many fingers or what size toys you can fit in your ass without it hurting. Make sure you use lube. Start at the small end and work up in size gradually after warming up and getting used to each size. If it hurts when you go up in size or add a finger, go back down in size again for a while and try again.

After you can easily and regularly fit 3 or more fingers in your ass, get yourself a nice butt plug about 1.5″ at the widest and start wearing it when you masturbate, and for half an hour or more before you have sex.

When you’ve been anally masturbating for a while and feel ready to try having anal sex again, wear the plug for a while first, then when you do the initial penetration with your partner, take control at first of how deep and fast to take him. If it starts to hurt, pause a moment. Push out as if going to the bathroom to help relax and open up. Resume. Repeat as necessary. As you can take him in all the way and start speeding up, he can start moving as well or taking control, but make sure he will pause for you if you tell him it’s starting to hurt.

Keep practicing, keep wearing a plug, always masturbate with something in your ass, and it will keep getting easier and easier to enjoy anal with no pain at all.

Anonymous: I love the blog. My wife and I have a great sex life. Over years we’ve worked up to anal sex and do it quite a lot. It is more passionate and the orgasms are more intense for both of us. However, my wife is concerned about doing it too often. She thinks it may make her incontinent. Is there real cause for concern? For the record we don’t do anything extreme, we always start slow and use lots of lube.

No, there is absolutely no cause for concern. You can have anal sex every single day for the rest of your life and not have a single issue so long as you follow safe practices and don’t cause (and then exacerbate) injuries. The anus and rectum are really strong, tough parts of the human body. If there’s pain or blood, you should always stop and let it rest or recover before continuing, so as not to make a (almost always very minor) injury something more that will take longer to heal, but just having anal sex with lube and proper warmup should not cause injury. If it doesn’t hurt regularly beyond standard soreness that can come from any sort of sex, you’re fine. Having it more often in fact makes it a lot easier to have without pain or injury.

The anal sphincter is a muscle, and using/exercising muscles makes them stronger, not weaker. Incontinence from anal sex is a complete and utter myth. The natural resting state of the anus is closed, and it relaxes and loosens when “flexed”. Increased use, practice and training of the anal sphincter can expand the range and size it can open up to to accommodate more, but it will still close up nice and tight when it returns to its relaxed state.

Anonymous: How do you reconcile anal only with the threat of poo?

Don’t have sex when you need to poop.

Anonymous: I hate your blog so much! I wish you would take it down. You’re making it so hard for women who won’t do anal to date anymore, all the guys want anal more and more or anal only, and I could never do that. Why do you insist on anal only so much? It’s like we’re all going to have to go anal only now just to get a date.

I highly doubt I have the influence to affect your dating life. Anal only may be growing in popularity over just a few years ago, but it’s still a fairly niche practice. Far more likely is the general cultural acceptance of anal leading to guys being more assertive for their desire or need to have anal. Anal is becoming like oral in the not-to-distant past—no longer a niche, something many people are expecting as a normal part of a relationship.

Just as these guys you’re encountering seem to be standing up for their need for anal, you can stand up for your disinterest in it. I guarantee there are guys out there who only want vaginal as well.

I’m not “insisting” on anal only, I’m advocating for it and encouraging people to try it, but beyond that everyone has the ability to decide whether they do or don’t want to have anything to do with it. As it turns out, a decent number of people like the idea.

That said, why not try anal? Try it on your own time, get familiar with it, masturbate with something in your ass. You’ll probably enjoy it. There’s a reason it’s getting so popular, and it’s not a one-sided thing just because guys want it. It feels really good for women when done correctly, and can make you orgasm better than vaginal/clitoral. It’s definitely worth experimenting with for your own sake, at your own pace.

The original version of this post on Tumblr received the following responses.

420spacequeen: I am a strong independent woman and fuck my ass on a regular basis. I love it!! So many nerve endings. Use a plug while masturbating your clit. Go bigger and bigger each size plug. You’ll soon be begging to be fucked in the ass non-stop.

wrexless: Masturbate with a butt plug in, or have your partner use a toy on you while you have a finger or plug (or anything really) in your butt. That’s how my wife got into it.

Anonymous: How to ask a girl if she wants to do anal? And how to prepare it? Is it messy at the first time? I really want to do anal.

Use your words? “Hey, do you want to try anal? I think it could be a lot of fun and it can feel really good if you do it right.” Reassure her that you’ll go at her pace, let her be in control, and put the focus on her pleasure. You’re going to enjoy how it feels no matter what, so prioritize her enjoyment of anal stimulation and she’ll want to keep doing it regularly. Read up on anal training and preparation together. Start small and slow. Always use lube. Don’t go for anal sex right away, use your fingers or some toys for a while and get her into how it feels before slowly working up in size. If she’s into the idea, encourage her to play with her ass on her own whenever she masturbates.

It can be messy if you don’t prepare or know your digestive system well. She should go to the bathroom before trying, and if very concerned about cleanliness, might consider using an anal douche to flush out the rectum before anal play and sex. With a balanced diet containing a good amount of fiber, the rectum is generally quite clean on its own except right before you need to the bathroom. Experimentation and experience will help make this easier to predict.

Anonymous: You are a man, right? So how do you know anal is all that good? Your ass has been fucked any time? Do you like being fucked?

I enjoy anal play as well, yes, but that’s not essential to knowing that women can love anal. Seeing the pleasure and orgasms women get from anal is enough for that, and having them beg for more and to never use their pussy or clit again.

Anonymous: Hi, may I ask, does anal feel as pleasurable for the woman as vaginal? Can she still have an orgasm as great? Thank you!!

Everybody is different, and there are always outliers, but it’s generally agreed by many who enjoy anal that anal orgasms are the most pleasurable there are. Not everyone is able to easily have pure anal orgasms (though many seem able to learn to achieve them over time and with practice), but clit + anal orgasms are still usually more intense and pleasurable than clit or clit + vaginal.

deepandlovely1: Anal penetration doesn’t have to hurt.

If it hurts, you’re doing it wrong.

If you enjoy the hurt, congratulations. Most people don’t. Stop pressuring both men and women into suffering anal.

Anonymous: Hi, my name is Lucy and i am 19 years old, my boyfriend has been pushing me for a while to try anal sex the to become anal sex only after sometime, and I always turn him down because I have a fear of having, pain and diseases from anal, and have a lose butthole. he is kinda wiled and rough so if i said yes for one thing he will keep pushing until he gets everything. i dont want to lose him and i wanna do the right thing, please advise me.

First, he shouldn’t push you to do things you don’t want to do and if you don’t want it, you should make that clear to him and that you expect him to request your wishes.

At the same time, your fears about anal are based largely on misconceptions. Done correctly and with the proper training and warmup first, anal will not hurt. Read the other posts here and elsewhere about anal training/warmup and start practicing with fingers and smaller toys well before trying to have anal sex the first time, and also of course always use lube.

Disease/injury is also generally not a concern from anal sex, again if you practice it safely and work to avoid pain—pain is a sign of injury, and so it should be avoided rather than ignoring it. And it can be avoided.

Getting loose or gaping open all the time is also a myth and something that just doesn’t happen. Instead, with practice and training your anal muscles become more flexible and can expand more easily within a wider range, and immediately after sex or play or plug wear you would notice being looser, but the resting state returns to being tight again quite naturally. Over time you can also actually strengthen the muscles (using them exercises them, as with all muscles) as well as gain more conscious control over how loose or tight you want to be at any given moment—relaxing loosening up at will to help with penetration for sex, etc.

If anal interests you and you’d like to try it, then I’d suggest doing so—on your terms. Start playing and practicing, fingering your ass while you masturbate, working up to two and then three fingers as you get comfortable with the first, then a dildo or a butt plug, and get comfortable and familiar with it before trying to have sex with your boyfriend.

Anonymous: I really like to watch prolapse porn, for me is such a turn on to see a girl like Proxy Page having her asshole hanging out after being fisted. I just would like to know how this happens. It’s because having regular anal too often, or it’s because the regular insertion of big toys. I would like to do this with a girl someday, but also I wouldn’t like to hurt somebody.

There are a few different things which people refer to as anal prolapse, but they’re kind of different. The medical condition of anal prolapse is generally involuntary and problematic, and it also isn’t known to be caused by anal sex—it’s more of a preexisting condition or something one might be already prone to. It’s quite rare.

In porn, what is often referred to as prolapse or rosebudding is something that is done a lot more deliberately, and occurs as the result of the anus being significantly loosened and relaxed in the short term through the use of large toys, fists, double/triple anal, etc., and then pushing out hard as if straining when going to the bathroom in order to force part of the rectum into view in the gape.

The former is generally quite a bad and unwanted thing, but the latter isn’t generally an issue or something that occurs outside of deliberately trying to do it after or during a long anal session.