Friday, November 25, 2011

How to Buttsex Someone Up But Good.

You want a buttsex post?  I'll give you a buttsex post!  I'll give it to you right up your... Internet connection!

How to Buttsex Someone Up But Good
1. Make sure your butt-buddy wants it.  Really wants it.  If you're doing this to widen their perspective on masculinity or femininity or sexuality, that's the wrong reason.  If you're doing this to prove something or score some sort of points, that's a really wrong reason.  Do it because they and their butt want it.  Ask them how they want it and prioritize that above anything I say here.

(Special note to cis men who have never "pitched" in anal sex: from what I hear, it's not transcendently pleasurable for a penis.  It's fun, sure, but it's not like a magical penis-amazing wonder above all wonders.  It feels like PIV intercourse only sort of different.  It will not bring you some ultra-mega-tight satisfaction that a vagina never could.  So control your expectations here, and if your partner isn't up for it, don't think you're missing out on the best thing ever.)

2. Make sure you're up for it.  Just because you're the penetrating partner doesn't mean it's no big deal for you and you have no basis to object.  It's fine to be uncomfortable with the idea of penetrating someone anally, or to have reservations or specific wishes about how to do it.  Just because you're not putting your ass on the line doesn't mean you don't get a say.

3. Be prepared for poop.  You cannot have buttsex if you don't have some level of comfort with poop.  It's usually not a lot, though; we're talking "smear" here, not "load."  Even so--put down a towel.  Put a glove on your hand and a condom on your dick or any toys.  Have some wipey things available.  There's no need for your partner to have an enema, but they probably shouldn't do this if they've got a poop on deck, if you know what I mean.

4. Be prepared for different reactions.  For some people, it'll be "OH GOD YES OH GOD," for some it'll be "mmm nice," for some it'll be "no, take it out."  People don't deal with anal stimulation in one way, especially if they're new to it.  And the same person on different days doesn't deal with it the same way.  Roll with however it goes.

5. Okay, let's do this thing!  Let's start with... how about some kissing and cuddling, actually? Just because you're using a different hole doesn't mean you gotta be all brusque about it.  Or some wrassling and spanking, if that's how you warm up.  But when your fore is played, let's start with a finger.  A finger with a glove on it, to spare you their butt-germs and to spare them your fingernail.  Lube it up real good.  You can't use too much lube.  Spread it all over your finger and use as much as will stay on it.  Put the pad of your finger on their anus, not pushing, just touching.  Have your partner relax and breathe and when you feel their anus relax a little, just slowly slide your finger on in there.

You'll feel two separate sphincter muscles.  The outer one is under voluntary control; the inner one isn't, at least not directly.  If the inner one won't let you in, don't try to push through, just let your partner work on relaxing and opening up.  (If it really won't let you in, your partner may just not be made for buttsex, at least not on that day.)  Gently massaging it can help.

6. This is the awesome part.  Or the start of the awesome part.  People's butts are hot and smoothly soft inside and you can feel the tiniest contractions of their muscles.  Despite all the warnings you hear about the rectum being fragile, it's also strong; it can grab your hand so hard you worry about yourself more than your partner. But the first thing you want to do after putting your finger in them, if they're new to this, is nothing.  Don't get all thrusty.  Give them a moment to adjust.  Give yourself a moment to just enjoy it.

7a. If your partner is the sort of person who has a prostate, look for the prostate.  (Well, don't look for it.)  It's going to be on the front--i.e., crotchward--side of their rectum, about two inches in.  (If they're Canadian or something it will be five centimeters in.)  A finger slid in all the way and bent should just reach it.  You feel it through the rectal wall, so it's sort of indirect, but you'll know it because:
A) It'll feel like a distinct bump about the size of a walnut, smooth and round.
B) Your partner is likely to go "OH MY GOD RIGHT THERE."

7b. There's two directions you can take this now.  (There's infinity directions. I'll talk about two.)  One is to continue on to the fuckin'.  The other is to just focus on the prostate, because you can get a lot of people the hell off that way.  Just keep rubbing it while you or your partner plays with their genitals, and it's likely to give them an incredibly powerful, I mean blasting orgasm.  I mean, I once made a guy accidentally hit himself in the face this way and he didn't even notice for a little bit.  Then he noticed and it was pretty amusing.

8. If you turned to page 238 to "continue on to the fuckin'," add another finger.  Slowly, gently, and lubily.  Pay attention to how they adjust to this--both in their anus and in their face.  You can gently slide your fingers in and out all sensual-like, but unless your partner asks you to, don't start thrusting like you're trying to churn butter in there.  Anuses aren't vaginas and it won't feel the same way that thrusting into a vagina does.

9. PENIS TIME!  Or dildo time.  Or, I'm not judging here, eggbeater time?  Take your fingers out of your butt-buddy's butt.  Put a condom and heaps and loads of lube on your implement of choice and do like you did with the fingers--just place it against their butt, and wait to feel them relax before pushing.  And again, give them a moment to just adjust to you inside them before you start doing anything.

You will probably not hit the prostate directly with an average-size penis or equivalent toy.  Maybe it'll get some driveby stimulation in some positions, but buttfucking isn't really prostate work.  Not the way Step 7 is.

10. I think you know what to do now.  But do it a bit less vigorously than you normally would.  A lot of in-and-out isn't really how butts work.  Unless your partner is encouraging you to do more, you want to err more toward the "sliding" than the "pounding" end of the scale here.  Check in with them; they may not want you to thrust at all but just be happy with you in their ass.  They may or may not want you to play with their genitals (or let them play with their own junk) while you're in there.  They may be able to go the distance, or they may need you to stop after a bit; again, the only way to know is to check in with them and give them permission to tell you to stop.

11. Clean up (probably don't do this on white sheets) and give your partner a hug and tell them they're awesome.

-If you're doing this with a bio-dick, use a condom even if you don't for vaginal sex.  Butt-germs can get in your urethra.

-Blood and pain are not normal, even the first time.  This isn't like losing your hymen; there's no reason the first time should hurt.  (People seem to vary on whether it's okay for it to hurt a little bit.  Personally I think it isn't, but at any rate any pain more than "a little bit" is too much.  If you're gritting your teeth to get through it, you're getting hurt.)

-Lube lube lube lube lube.  And then add more after you've been going for a bit.  Butts not only don't make their own lube, they suck moisture out of the lube you put in them.  Keep things messy wet.

-There are bacteria in the ass that can make you sick if they get in any non-ass body openings.  Don't put anything that's been up someone's butt in anyone's mouth or vagina.

-Your butt-buddy is putting their ass in your hands.  (And vice versa.)  That's one hell of a gift.  Treat it good.


  1. This is the most useful guide to buttsex I've ever read, and that includes all the sex guides I've read and all of the rest of the internet.

  2. Oh thank you thank you for posting this! My partner is going to be visiting me in less than a month and buttsex is something zie's really into, and I was kind of nervous (and excited!) about doing it/having it done to me and now I'm less nervous and more excited. Awesome!

  3. Great post some very good advice there

  4. Sex... with a butt?

    What is this madness.

  5. Hooray... For BUTTSEX!

  6. If it does hurt (using all these precautions) but is really good anyway, does that mean I'm hurting myself and shouldn't do it? It also hurts the next day...

  7. Your note to cismen makes me very, very happy. It needed to be said.

    I think when an (anally experienced (pitching)) straight guy is obsessed with anal sex, it must be for reasons other than the actual sensations - the taboo-ness or the guaranteed-not-to-get-her-pregnant-ness or something. 'Cause every guy I've ever asked about this has said that ass feels pretty much like vag. (One guy said that ass is more "tubular" in shape, another said ass is less ridgy. That's about it.)

    1. Ok...short time lurker, first time poster.

      Great site!

      That a guy, who's SO really likes's very different than PIV, but not.

      It can be much tighter...or more localized tightness. You can really feel the ring of muscle squeezing on you all the way.

      Whereas PIV is more generalized squeezing. The physical differences in the musculature kinda show this.

      My experience, my .02...for what it's worth.

      Did I mention Great Blog?


  8. Anon - Honestly, I'm not sure. Any blood is definitely bad, and any big hurt is bad, but I'm not sure to what degree little-hurt is okay or not. I err towards none but I know other people feel it's just normal for them.

    Any other commenters want to weigh in on this?

    Perversecowgirl - I've also heard "vagina is looser on the outside and tighter on the inside, ass is tighter on the outside and looser on the inside."

  9. I think when an (anally experienced (pitching)) straight guy is obsessed with anal sex, it must be for reasons other than the actual sensations.

    This has been pretty much my experience. I've only had one boyfriend who was OBSESSED with it (to the point that it was eventually all he really wanted to do, which ended up ruining our sex life because my experience of it has always been somewhere on the spectrum of uncomfortable to outright excruciating). He was definitely into it for the taboo/scoring rather than the actual sensation.

    I've met other guys who liked it, but they were also pretty okay with not doing it, too.

  10. Awesome post. The only thing I would add is that either one of you may have a emotional/psychological response that you did not expect. I find it makes me feel very small/ashamed which is *great* for a D/s scene that plays consensually with that feeling but not so good for a happy, fun scene. I also second giving your partner hugs and reassurance after.

  11. I've been curious about anal (giving AND receiving) but never actually done it. This guide should help a lot with my first time. :3

  12. I have to second the fact that it's sort of 'meh' for a cismale giver, unless there's some psychological stuff behind it. The 'tight on the outside, loose on the inside' seems on the money, and since most of the sensation in my experience comes from the tip rather than the shaft, it's actually not that great (with a tight asshole, it's actually a bit uncomfortable as well).

    It is pretty awesome as a recipient, however. :)

    I prefer analinctus to anal penetration, personally, and it's a lot easier to sell to partners that are otherwise shy about anal. I've had partners go from "hmm, anal seems scary" to "OMG penis, in, now!" in just a 10-20 minutes of playful licking around that area.

  13. Regarding the pain thing - any big hurt is seriously bad, small hurts depend on what kind of pain it is. If it goes away in under a minute I'd say that's normal and probably just not enough lube in a spot for a moment, or perhaps too much tension in the recipient at that time.

    If it's still hurting the next day though, my general gut instinct is to stop and change something about it. It shouldn't still hurt the next day.

    We had a serious incident once where I didn't stop him and I had pain for over a month. Really, really not sexy.

  14. Great post. BUT! While it might feel much the same as vag. sex *by itself*, once ones partner is practiced, there are combinations available! You can mix and match with different textured/sized things in front and back! In my experience as cismale pitcher, this road leads directly to wow.

  15. Written from the point of view of a female on the receiving end, I really recommend play sessions with yourself in the shower. Particularly if you've enjoyed the wonders of the faucet on your clit before -- with the right type of faucet, of course (oh how I miss the one I had at that shitty apartment back in the late 90s, but really the ones back when I was a child were the best. I started masturbating back when I was 5, so I know what I'm talking about :) )

    Take lube to the shower with you, water's not the right consistency. A finger or thin toy, well-lubed in either case, sliding slowly up your ass when you're extremely aroused already is delicious. If it's an option, getting a few butt plugs of different sizes and playing with them is fun.

    Couples situations... if your partner has great oral sex skillz, it's a winning combination and a great way to start. In my case, I was already intimately familiar with my own asshole from quality time with myself in the bathtub, so I knew how different things felt. It's also a great way to see what you'll be dealing with in terms of your own body's poop output.

    In my own experiences I was the one asking for it, so I've been lucky to never have to deal with a guy dysfunctionally obsessed with anal sex, but I agree with everything said about that upthread. It seems like a red flag in many situations, and if it's a healthy fetish for your partner that you simply don't enjoy that much after open-mindedly trying it several times, maybe you're not that compatible sexually? Again, just my personal opinion when imagining myself in such a situation.

    From the point of view of the giver, it's nice to see "my cock" sliding in and out of someone. Makes me wish I could be a guy for one day and just experience what that feels like (p.i. any hole that's pleasurable to your partner)

  16. So I know this directly contradicts point #3, but can someone please give me a 100% No Poop Ever guide to buttsex? :| I am seriously, intensely OCD, and the intended function of that particular hole is the only thing keeping me from trying anal (which otherwise sounds sicknasty hot.)

    Also, this is probably not a very useful piece of advice from someone who just admitted they've never tried it, but my guess on "when is pain OK" would be "when it's not sharp". Same as when you're exercising or getting fisted! A little bit of slow burn is okay, and sometimes good if you're into that, but the second it feels like anything might tear or break, call it quits.

  17. @Anon@8:13, re: no poop ever: I would say the closest you'll get to no poop is taking a bunch of enemas beforehand, but even that route means you'll have around poop?

    Anon@6:26, seconded. I only want anal when I want to feel violated or small - otherwise it doesn't really turn me on that much to receive.


  18. I'm also horribly OCD. I'm curious about what pornstars do. It helps if your partner has a healthy attitude to poop. It might happen.

    I've tried enemas (maybe not enough water?) but it didn't quite work. It made my butt feel odd and sort of washed stuff down the digestive system. What worked best for me were showers and slowly getting larger and larger toys up there before buttsex with a human partner.

    In terms of pain, wow, if you tried fisting, you can do anything, no? At least what it seems like to me, I've never tried it and it seems scary. I'm sure the principle is the same, if you go slow enough (the more lube the better) and give your asshole time to relax and accommodate thicker and thicker objects, you can end up surprised by what it can comfortably hold.

  19. do you have a lube recommendation holly?

  20. Haven't even read this yet, but I'm totally amused at the title... and certain that earlier posts of mine contributed. I think I'm going to quite enjoy this!

  21. On the issue of poop/lube side effects, the correct term is santorum. See:

  22. "If they're Canadian or something..."

    I have several lube recommendations, but ultimately, you'll probably have to talk to your local sex shop owner: the three things you'll need to talk about are: what are your toys - if any - made out of; will you **ever** be using condoms (be honest, if you think you're just going to use your cool, stainless-steel toy but you know you or your partner might wanna try things using a phallus at some point, err on the side of caution); and will you ever be in a situation where you might get some lube in your mouth. This doesn't just mean getting a face full of ass - when you put lube on, it can go to nearby spaces (in fact, should!) that might get kissing or other oral attention even before any penetration begins. Effects on toys, effects on condoms, and effects on flavor will create different needs for different people.

    Finally, about poop: I've done anal sex with partners and by myself quite a number of times (enough that I don't know how many, but surely more than 50). Because of meds I'm on, I tend to have less frequent bowel movements that involve more poop at once. If I have sex within a few hours after that, I'm pretty much guaranteed to have no poop at all. If I don't really have to poop but try, sometimes that moves small amounts in/near the rectum even if I do more some out. I don't like poop. I prefer strongly not to be around it, but it's possible that I'm less OCD about this than you.

    I would recommend that you think about what you eat at least 24 hours beforehand. What you eat 8 hours before hand will have no effect, generally. If a couple days in advance you take metamucil or eat lots of fiber-y foods, you really will poop out everything that's anywhere near your anus. But you don't control the exact timing, so you need to be willing to make sure you get around to the buttsex within 4 hours or so if you try this.

    While enemas are also an option for some, if you don't know what you're doing, they can backfire by making things mobile without getting everything near the exit out. If you decide to do the enema thing, try it 5-10 times before you use it with the intention of having sex. At least, that's advice that seems to be good from my experience and that of friends.

    and, THANX HOLLY!!

  23. ooops, I meant to mention that the canadian comment Lol'd me.

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  25. Both my partner (cis man) and I (cis woman) both really like butt sex. I was the penetrator before I was the receiver. When I was ready to be the receiver, it was incredible. Part of it, I think, for us was that we always found it weird and fascinating that we don't know what each other's genitals feel like. Then, all of a sudden, we both knew what it felt like to be fucked in the ass. We had a pretty good idea of what sensations we were giving actually felt like. Now it's this super awesome point of commonality. And also really fun!

    (Oh! Also, I don't think I've commented here before? At least not in a long while. Anyway, both I and my partner read your blog religiously! You are great. Thank you!)

    Yay buttsex!

  26. This really is a very good post on the subject.

    I've done this a lot. It always hurts a little, but so far it's never hurt a lot. I'm not at all into pain, so if it hurt a lot I definitely wouldn't do it. It feels VERY good to me if done right.

    The day after it's always a little sore, a little uncomfortable going to the bathroom, but for me that's normal so I expect it and don't worry about it. It never hurts just standing around or anything, just when going to the bathroom. The reality is you're getting new poo into a sore area, so it does sting a little. But for me that's no different than with vaginal sex, which is always a little sore the next day too, but stinging because of pee instead of poo. Lovely subject isn't it!:)

    Back when I was married we did it without lube, but I wouldn't advise it. It's much more sore the next day that way, and it does potentially kind of get a little infected, where it itches a lot for a few days. Imagine an itch up your ass that you can't scratch. Not fun. So definitely use lube! Each time I've done it with lube it never itched the next day:)

  27. no poop anon: In my experience, there often isn't poop. I would suggest watching what you eat and what your own poop output is in general - if you are pooping solid, discreet poops, you shouldn't have any left up in your butt when you're done. If you do encounter poop, you can call off the buttsex for the day and try again another time.

    I know this isn't making it sound very appetizing... but seriously, great post, yay buttsex.

  28. Have you pegged Rowdy yet?

  29. What kind of gloves are good? I've never bought any.

  30. Anon: I use black latex gloves from babeland for safer vadge finger-banging,they'd probably work great for buttsexin too

  31. Just wanted to add that blood and pain are not "normal" for first something-in-vagina sex either. Maybe its often experienced that way (which is fine if the person likes it) but theres usually other options.

  32. "Be prepared for poop."

    Words to live by.

  33. Great post, Holly! By far the best buttsex guide I've read, especially for the emphasis on touch the opening without pressing it, which I will definitely be spending more effort on.

    I have one minor criticism which is that, for completeness, you might want to mention the possibility of moving up to 3 or 4 fingers on the way to PENIS TIME. My experience has been that most people don't especially enjoy having three or more fingers, especially if they're moving around, but it's sometimes a necessary step. Depending on the circumference of the penis involved, the jump from two fingers to bio-cock can be just too big to make as one step.

    I also want to chime in on the discussion of physical sensation in cis male penetrators. I'd agree with the commentors saying that anal penetration is not noticeably more pleasurable than vaginal penetration, but disagree that that means a preference for anal is necessarily psychological. There are valid physical reasons to prefer a kind of stimulation besides pleasure.

    For some men, reaching orgasm requires a prolonged period of firm squeezing near the base of the shaft. This isn't really any more pleasurable than more conventional tip-focused activities, which can and do feel amazing. It's just necessary to achieve ejaculation. Anal doesn't really feel any better than vaginal, but some days it can get me off when vaginal can't.

  34. Perpetrator of Buttsex :) Funny :)

  35. Answering a couple questions:

    Poop-wise, I don't know how to make buttsex guaranteed poo-free, but it sounds like there are some people above who know more about it than me. I do want to reiterate that when I say "poop," think "brown spot," don't think "entire chunk of turd." That's not likely to happen unless you're having buttsex right before you need to go to the bathroom.

    Using black gloves and condoms, and putting a black towel under you (and putting it straight in the wash!), can also spare you from knowing about poop.

    Rowdy-wise, I have not full-on pegged Rowdy yet but we have had some very fun buttplay. :)

    Lube-wise, I'm not enamored of silicone; I like water-based gel lubes. I generally use Astroglide gel (Astroglide liquid does nothing!) and have been pretty happy with it.

    Glove-wise, the regular latex (or nitrile if you or your partner are allergic) gloves at the drugstore will do fine, but you can also buy nice black nitrile gloves online. Amazon has plenty of kinds for pretty cheap.

  36. How I know I am not mature: Tip #1, while being strikingly good advice, still cracked me up.

  37. How I know my partner isn't ready for buttsex:

    Me: So Pervocracy's new post is a guide on buttsex
    Her: Eww... poop

  38. Oh my. I wish I'd had this before I first pegged my bf. I just put on the strap-on with a condom and some lube and pushed, guided by his "deeper" "stop" and "no, go back, that hurt".
    The cock we used was huge - as in "what is this I don't even" (though, before anyone jumps on me, HE had bought it).
    We still have lots of fun, very little pain and near to never any poop whenever we do it - but a guide like this would have made the start a lot easier.
    I will show him the post when we talk next time about him anally penetrating me - a thing I've always kind of feared, but now, as I'm in a very trusting relationship in which we've tried out all manner of things to date, am willing to give a try one day (or rather night). I'm even kinda excited about it - and this post had a part in that :) Thanks!

  39. On receiving: Something you might want to consider, if you try buttsex for the first time and it isn't bad but it isn't wow, is that the first time you try it you might be too anxious or wound up in new sensations to really appreciate it. The second time I had anal sex was the first time I had an orgasm with a partner. I am certainly NOT recommending going back to something you really dislike or that hurts, but giving it a second chance if your first experience is only "Not so bad" or "Meh" or "Hunh, interesting" might be rewarding.

    Also, consider position! The receiving partner being on their hands and knees might not work very well. With my partners I've had a lot of success in missionary-with-pillow-under-butt. And if you want prostate stimulation with a partner wearing a toy, you can get toys with varying degrees of curve.

    Lube recommendations: Swiss Navy makes some of the best water-based lube I've tried, and they make it in lots of really cool flavors. For silicone, I tend to splurge on Pjur, but Pink is nice and has vitamin E.

  40. Bad Idea #15478: Eating chocolate pudding while reading a comment thread about buttsex. I had to stop and remind myself several times that what I was eating was not what I was reading about. >.o

  41. Also the title of this post is freaking hilarious.


  42. As a cis-male, I'll second everything Orion @3:33 said about penetrating.

    But on the other hand, I also found that the lack of tip stimulation had the huge benefit of, so long as my (long-term, female) partner was happy with it, letting us stay coupled after I got off, and then relatively soon being able to continue without having to get back to a full hard-on with which to re-penetrate her. Also, one of the things we really enjoyed was sitting together with her on my lap, and my dick in her butt. It was really convenient and we could rest and chat and just be together that way, punctuated with great sex.

    Also, on one of my much less cis- days, we pulled off something rather mind-blowing, at least from my perspective as somebody tending toward MtF. We started with both of us on our backs, her on top, my dick in as far as it would go. Then I used a vibe to get her off, which (a) was fun in itself, (b) sent all her little shivers straight to me by a rather direct and sensitive connection, (c) allowed me to effectively borrow her pussy for a while, since fun with a vibe, applied by me to the spot pretty much exactly where a pussy should be (except just a little higher than my own would be if I had one), with an exact match of applying the vibe and getting stimulation (see (b) above).

  43. The Swedish scientists told me that we don't "lose" our hymen. It's always there and it's the vaginal corona now.

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  45. One more tip: consider waiting with the penetration until the receiving partner has had at least one orgasm. In my experience (cis female), the endorphins and general worked-up-ness after an orgasm often make anal penetration easier and more enjoyable. On a related note, try masturbating while being penetrated - not just after the dick/toy/what-have-you is in, but while it is in the process of working its way in. I have found that this can often take things from "gah, uncomfortable, can't take it" to "oh wow that feels great".

    As for lube recommendations, I have a different experience than Holly - Astroglide doesn't work for me at all; it fine for PIV but oddly burns for anal applications (shows how this is totally individual, I guess). I am a big fan of Probe for buttsex (stays nicely on condoms, too, while other lubes rub off to quickly for me). And if you live in Germany, try out Superglide. How I wish they sold it in the US!

    And finally, Anonymous at Dec 2, 12:14 AM: Thank you so much for doing womankind the favor of leaving us the hell alone (er, "quitting the sex scene").

  46. Anon @Dec 2, 12:14 AM: What the...? Huh? What? I... I don't even... what? I don't understand. Instructions on how to have buttsex are the reason why you no longer want to have sex since you turned 30? Because the instructions... made you not have buttsex when you were in your 20s? HOLLY HAS TIME-TRAVEL BUTTSEX-NEGATING POWERS?

  47. Just wanted to add that blood and pain are not "normal" for first something-in-vagina sex either. Maybe its often experienced that way (which is fine if the person likes it) but theres usually other options.

    HAHAHA I had heard this kind of thing so when I first had PIV and there was a little blood I thought I had serious internal bleeding or something.



    Dude: I think that's what happens?!

    It was very Victorian, in a way.

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  49. Dude, it's tough for shy women, too. You don't see me complaining.

  50. Just wanted to add that blood and pain are not "normal" for first something-in-vagina sex either. Maybe its often experienced that way (which is fine if the person likes it) but theres usually other options.

    I dunno about this. When I had my first PIV sex it hurt and I bled like crazy, and that never happened again even though we didn't change anything in how we did it.

    I think hymen mythbusting has sometimes spilled over into forgetting that some people really do have intact hymens which really are torn during first intercourse.

  51. Mine was. Except I did it myself, so it wasn't so dramatic and Victorian. But there was a little bit of blood. No biggie.

  52. Also wanted to add to this discussion - RIMMING! It's great. Another great way to get someone's ass ready for a finger or two or six, or a cock, or whatever it is.


  53. About the hymen/corona thing, I'm going to second the fact that for some people it will hurt the first time and that will be normal. Mine had a little band of hymen/corona tissue that went across the vaginal opening, and there was absolutely no way to get a penis in there without breaking it (the band could be pushed to the side enough to accommodate a finger, but nothing bigger). Not surprisingly, snapping that little band of tissue hurt a little, and I really don't think there's anything "not normal" about that. It was mildly sore for a couple days afterwards while it healed, after which sex was generally always fun and pain-free (not that the first time wasn't fun too), so I really don't think the initial pain was a result of how we were doing it.

  54. Re: "I'm curious about what pornstars do."

    They edit the poop out of the final video!

    (Unless it's THAT kind of video.)

  55. I tried anal for the first time quite recently after noticing I was longing to be kinda... filled up a little more during masturbation. My partner had tried it before but his other partners hadn't been big on it so from that I was expecting a little disappointment.

    But it was amazing. It did hurt a little, but I chalk that up to nerves, because it's been pretty much A-ok since that first time.

    And on the hymen thing, I bled the first 7 or so times I had sex because I decided I wanted to stop every time I had a tiny bit of pain, which stopped it from breaking completely and probably resulted with it healing over a little bit. The last two occasions I went 3 or more months without PIV sex I also bled.

  56. I think that a lot of women who have an intact hymen/corona which needs to be broken for PIV to occur might benefit from breaking it intentionally prior to attempting PIV. I have no memory of my hymen/corona, so this is purely speculative. I just know that I would personally prefer to deal with pain and bleeding in a supporting (rather than a sexual) environment.

  57. I'm nthing the hymen comment. I did everything I was supposed to my first time to not experience pain, and it was still painful as hell. This after I had been masturbating with an internal vibrator for two years and used a menstrual cup for almost a year as well.

  58. I'm normally a lurker but there's nothing like a butt sex post to inspire commentary.  First of all, great advice.  Butt sex advisories always do the "lube, lube and more lube" advice and the "dont' go back to front" advice but rarely espouse the most important one.  Be really really turned on and into your partner first.  I've seen lots of comments on butt sex advisories where people will outline their clinical, almost surgical preparation for butt sex and then wonder why it wasn't the thrilling experience they were expecting!

    The first time I had butt sex with my partner, we were having great vag sex and I was really wet and turned on.  He started rubbing his cock along the crevice of my ass (which is sexy as anyway), but because I was so turned on, I started pushing back against him and he slid right in.  Fan-bloody-tastic.  Butt sex is a part of our repertoire now, and it's always thrilling, obscene and incredibly raunchy.  

    A couple of things I wanted to add:
    - if you are starting out, it helps to put the receiver into a position where they can control the penetration.  That way, if it's painful or uncomfortable, the receiver can stop it immediately.  And if it feels great, then the receiver can push back against their partner for more.  One way to do this is via side-spoons position.  The other way is lying on your front, but with the other person angled at less than 45 degrees (yes, I know this is starting to get clinical).  This controls the depth of the penetration.  As I'm getting into it, my partner then starts to rear back so that he's closer to 90 degrees.  At that angle, he's got his full length into me and it is seriously forceful.  It feels brilliant when you're turned on and ready; but if it happens too early, it feels like a freaking baseball bat up there!
    - Love the sensation of my partner coming in my arse.  I can feel the pulsations in him more than when he comes with vaginal sex.
    - Unlike vag sex where the come just leaks out and you have a big wet spot, the come stays inside with anal sex and it's neat.

  59. Awesome blog post. My boy-cunt thanks you.
    sev xx

  60. I must say how happy I am my girlfriend and I read and put this post to good use the night before I almost lost a finger at work. Good news, I have nine more. Bad news, that finger is way out of commission for a while (right index - booo).

    Side note - Holly, do you know any kink involving finger splints? ;)

  61. I'm also horribly OCD. I'm curious about what pornstars do.

    The one I've seen comment on this combines enemas with fasting.

  62. I second the comment about rimming- I don't think I've ever engaged ye olde sphincter without a nice extended rimjob preceding it- and I really can't imagine it would be very pleasant to go from cuddling straight to fingering without getting my partner's butt all tingly and turned on first!

  63. This is fabulous!! Well said, all of it!

  64. For those trying to avoid poop who have vaginas and are planning to be on the receiving end: sticking a finger in and pushing back should let you feel along a good portion of your butt, and can reassure you that there's not a chunk stuck. (yeah there's just no way to make that not kinda gross to describe, sorry) When I was on medicine that made me seriously constipated I used a related technique to avoid straining occasionally.

    Also, I personally vote for two fingers being followed by a nice smallish toy before going to a cock (or similarly sized implement).

  65. Thanks to all of you who mythbust the idea that pain/bleeding are "normal" for PIV debut. Seems like it should be preventable by some sort of stretching exercise for any tight part, some time before one becomes sexually active.
    Good articles, all.

    1. No thanks to all of you who "mythbust" that my first sexual experience was normal. Not bleeding the first time you have sex? Normal. Bleeding the first time you have sex? Also goddamn fucking normal!

      Different hymens come in different shapes and have different pre-sex experiences. Mine wouldn't have accommodated a penis without breaking and I didn't choose to break it before my first sexual encounter.

      "Seems like it should be preventable by some sort of stretching exercise for any tight part, some time before one becomes sexually active." Seems like you shouldn't be making prescriptions for people whose bodies are different than yours.


  66. If they're Canadian or something it will be five centimeters in...awesome!

  67. Hi, Very late response, but so curious as to how (if at all) people reconcile the specific butt germs possibly entering other orifices (namely the mouth) with (awesome, dirty) things like rimming, ass eating, A 2 M, etc? Anyone with safety advice (I am guessing dental damns? changing condoms?) that have been fun and sexy and successful for the parties involved?

  68. enjoyed this! very informative. as a cismale i've never actually given, but have received from a few of my partners that were into it. i am DEFINITELY into that!

    and "rimjobs" on either end, has been enjoyable. i've always just brushed and used mouth wash.

  69. It's great sex between two hot guys. We kiss and cuddle and usually he wants to be pentranted and hard and am large and I give it to him; if it hurts, I back off, but I can cum in a condom the same time that I always make him cum. We have been together 13 years and do butt sex several times a week. Sometimes he does it to me and I do it to him. We both do not pull out when we want to climax and fill out condoms but we know when each is ready to explode. Best sex ever!!

  70. What if someone doesn't want to use condoms or lube? What if condoms and lube are cost-prohibitive, or just a personal hard limit of one or both participants? What are these supposed diseases one can contract from anal mucous entering the urethra? If both participants are completely exclusive to each other and have never had sex with anyone else, is there still a germ risk, and if so, what kind?

    I'm asking this because there's a lot of woo about germ risk, especially around "edgier" activities like, say, bloodplay. Some of it might be legit. Others sound like straight-up fearmongering. So is there any real evidence of unprotected anal sex with two exclusively monogamous participants with no prior sexual contact with anyone else leading to disease, sickness or infection from human butt-germs alone that couldn't feasibly be attributed to something *other* than naturally-occurring ass-bacteria?