Comments

1
Are there many letters about "accidental" anal penetration that are written by Victorian matrons?
2
ANALSLIP, I would recommend you have your her sister to read the "accidental anal" column herself. Although I'm thankful this has never happened to me, my recollection was that many regular commenters reported that this happened in their experiences more than once. I would also recommend you find the column from the woman whose drunken boyfriend intentionally penetrated her anally and wanted to know how to speak with him about that incident. You and your sister might be better able to judge her experiences after reading through those columns and their comment sections.

As for whether you can tell the difference between a vagina and an anus (or the proper positioning of your bodies), I will note that I don't often have sex in a spooning position, but on one occasion, my girlfriend attempted to maneuver me into her vagina while I stayed still. That process took a long time, long enough that I wondered whether she wasn't angling me so we could have anal sex. In any event, that was her anus and her vagina, and yet she had difficulty orienting her body for vaginal sex.

I do have to disagree with the following: "If his apologies are followed by nothing but withholding behavior ("[later] she approaches him in hopes that their amorous endeavors will continue but he then refuses"), that's a bad sign." I'm not sure that this is right. I could easily imagine that the man who through a genuine accident anally penetrates his partner, something he knows has caused her physical pain, might very well shy away from a continued invitation for more sex. When you do some wrong, and feel genuine remorse for your action, even if it was accidental, being told that's ok and you can have more sex, might still make it hard to forgive yourself and go back to having more sex.
3
Maybe Dan has only been with vestal virgins, but I've been with a few guys you could absolutely slide right into perhaps even by mistake if they had another hole down there to aim at. Also, I'm sure some people are just born with wide set assholes.
4
All I needed to read was 'long time fiancee'. DTMFA.
5
I guess i'll accept that accidental anal can be a thing... but I imagine that only an experienced anal sex receiver could ever possibly be, uh, accomodating, without a lot of time and lube?
6
I know that assholes require some warmup, and accept penises and toys much more readily when lubricated, which would usually involve inserting a finger. Anal without lube is bad enough, but anal without warmup—meaning a sudden, fast, complete insertion—is going to be painful for all but the most, ahem, seasoned holes.

My straight friends tell me that a vagina also works better when lubricated (naturally or otherwise) and appreciates some warm up, meaning that initial thrusts should be slow, gentle, and shallow.

This leads me to wonder how well this story was related to the LW by her sister. If the guy was taking it easy with the first few thrusts, there should have been plenty of time for her to move away or say stop. [Note that I am not blaming her, just questioning how this really happened.]

Also, if you surprise the asshole, it's likely to tense up and get even tighter than normal. The guy risks literally breaking his dick.
7
@5 I'm commenting for the first time after years of reading to say that I've never had anal once in my life, yet have managed, without trying, to slip two fingers in (to the knuckle) while soaping up in the shower. Freaked me out, not because fingers in the ass, but because I didn't think that was physically possible!
8
@6, agree that I wonder how well the story was related by the sister. She clearly has a negative opinion of D, and whether that has colored her account is uncertain.

That said, IMO the distinguishing characteristic of accidental vs. "accidental" is whether penetration occurs. Having your aim be off, at the beginning or after slipping out, is easy enough to do, but the anus takes some work to loosen up to be receptive. I've bumped up against the anus plenty of times and each time my dick bends/jams a bit which is not pleasant.
9
One time a guy penetrated me analy accidentally, it was in missionary and we were super drunk. I dont think he even realized and so I just let him finish in my ass, it didnt hurt...

Next two times I was ready for it but- damn, ouch, I was not prepared for the pain and I had to stop it immediately. Insanely painful! So I think accidental anal is super subjective.

Now I enjoy anal with my wonderful and considerate partner, but about this letter writer...she should really let her sister know how much she hates her fiancé. She should tell her sister how she cant fucking stand the fucking asshole! Dont go to the wedding, ECT. Its hard to end relationships, let her know you're there for her and tell her she can do better, damnit...

Theres a lot of reasons to end the relationship- he exhibits general manipulation type personality disorder, has 2 kids from a previous.failed marriage, and is unwilling to commit past engagement. And now the anal slip as the icing on the cake. And she was in pain for days?!? Jesus. I don't know how she can even look at the guy let alone want to continue sex after the anal slip...

10
Bring it up to the rest of the family? Am I the only one thinking that if this even a possibility that this family has some boundary issues? I guess at the least, Xmas dinner won’t be boring.
11
Surprised Dan didn't point out the common theme in truly accidental anal - missionary position. I can't speak from experience, but the physics of missionary position makes sense for being conducive to truly unintentional anal. Doggy-style I would find very hard to believe is sincerely accidental and would be inclined to label as "accidental" based on the position alone.
12
Another vote for the existence of true accidental anal. When things are really aroused and super lubed up down there things can slip. In my case, it did happen in a from-behind position. If the (my) guy is leaning down instead of sitting up, his penis actually lines up better with my ass, and vaginal takes a little manouvering. This was in a relationship of multiple decades of consent awesomeness.
13
On the opposite side of accidental anal the spectrum, I've tried to get it to "accidentally" slip in. It didn't work so well. My husband is slightly above average, but with the right warm-up, anal is no problem. I've never, ever, had someone "accidentally" manage it. It's difficult enough to do intentionally. I'd imagine this poor girl was crying out in pain while he was still accidentally shoving his cock in there. It would be one thing if he got the head in and went "my bad" and pulled out, but the full thing? That's not an accident.
14
@4 agree

@13 also agree. A little blip with the head would be one thing. As a woman who often uses a strap on, even with some warm up, thrusting into an ass is completely different than a vagina. If *I* can easily tell the difference via a big hunk of rubber, I severely doubt this guy is legit.

As a counter-balance in my own experience, I once had legitimately accidental anal, in that the guy (my bf at the time) completely didn't realize until way after the fact. I think he felt pretty stupid that he somehow hadn't noticed - it came up like a year later in a conversation about "trying anal" lol. However even with that happening, I feel completely sure that if I had cried out in pain, or otherwise indicated in any way that I wanted/needed to stop, he absolutely would have.
15
Sportlandia @5: As vab251 @6 says, it's possible, yet painful (exactly what ANALSLIP's sister described). I have had men attempt "the wrong hole" from behind. If you're horny and relaxed, it is possible your sphincter could be loose enough to allow a surprise (smaller) penis if inserted with enough force, as ANALSLIP's sister described. Four examples of accidental anal during missionary do not mean that accidental anal is ONLY possible during missionary. I've experienced the penis slipping out and bouncing off the anus during doggy as well; there wouldn't have been time in that split second to aim it there. (And Sister is an "experienced anal sex receiver" ["During previous discussions about sex, I understood that my sister enjoyed anal play with D"].)

If Sister is inclined to give Fiancé the benefit of the doubt, she should ask him to proceed with more caution on his initial approach, regardless of position, and regardless of which hole he's aiming for. I'm sure their spooning sex wouldn't have been compromised by his easing his cock in, instead of ramming it in.

Vab @6: "If the guy was taking it easy with the first few thrusts, there should have been plenty of time for her to move away or say stop." He wasn't. But I agree he should have been. (This is not generally a problem when it's an aroused vagina. Perhaps a problem of style, depending on preference, but not one of pain.)

Hanasaam @9: "Theres a lot of reasons to end the relationship- he exhibits general manipulation type personality disorder, has 2 kids from a previous.failed marriage, and is unwilling to commit past engagement."
Wow, way to shame people for being divorced. "Failed" marriage? "Unwilling to commit past engagement"? How do you know he's the one delaying a wedding? "Personality disorder"? Are you a shrink? (Obvious answer is no, because "manipulation type personality disorder" is not a thing.) Repeated breakups are a red flag, but half the dating public is divorced by their 30s or so.

B07ias @12: Thank you.
16
Bodies differ. Angle of the erection, cock size, distance between orifices, positioning of legs, maybe even size of the people involved all can influence this. And being otherwise aroused might provide enough lubrication for anal entry (I don't do much anal, but when I do it's, shock horror, without extra lube, though definitely slow and gentle to start with).

Vab @6 -- if a woman is genitally aroused (and I would assume it's a necessary condition for piv) there is usually no need to be slow, gentle and shallow to start with, a deep single thrust is perfectly possible, can be welcome and very pleasurable.

Accidental anal is definitely possible and on the rare occasions it happened to me it was from-behind and not during vigorous thrusting but during one of those in-between moments: lots of natural lubrication, cock already wet, orifices receptive/relaxed, high arousal. But (which is where I agree with @ 13/14) it was never a full insertion (for my body that's nigh on impossible without my cooperation or, I'd guess, serious violence). So I do wonder about the technical accuracy of this account, but if it IS accurate, then it looks like an assault. Although not wanting to continue afterwards is for a me a good sign, not a red flag at all.

However (and this will be unpopular opinion), I don't think it's the LW's business to kick this guy's ass, however much she wants to. And I also wonder about this whole letter, because discussing anatomical detail of your sex life with a close family member who clearly detests your partner just seems... idk, wrong? Unlikely? So I wonder who's doing the manipulating here.
17
The question has nothing to do with accidental or "accidental". That's all red herring. Here's the real question:

My sister is in an off again/on again relationship with a guy who assaults her from time to time but then is always sorry. My sister, for whatever reason, stays with him. Maybe she likes his other qualities. Maybe she thinks she can't do better. It breaks my heart to see her so embedded in the classic domestic abuse cycle of assault/apology/forgiveness/repeat. What can I do to help my sister?

Answer: Be there for her. Make sure she has a safe place to go. Make sure she can see how positive life without this violent sexual assaulter can be. Suggest a possibility. If she can't bring herself to dump him already, suggest that there be a penalty each time one of the assaults "accidentally" happens. The penalty should be huge and irreversable. Also document each case. Since the sister is in pain each time, she should see a doctor each time. She has to get into the system with others knowing what's going on.
18
It's clear that D. can't say to his fiancee: 'I would like to take you up the ass'. Instead he periodically tries to force her (maybe stupidly counting on her consent as it goes on).

The LW's sister's relationship would seem to have lots of issues. I'd think the LW can discuss these with her in the round, rather than getting tied up in an arcane consideration of how plausible straight doggy anal is.
19
Harriet @18: Sorry but that's not "clear" to me at all. What's clear is that sometimes they have consensual anal sex ("During previous discussions about sex, I understood that my sister enjoyed anal play with D"), which, to me, means it's more dubious to conclude that these accidents are "accidents." If one knows that forcing will result in pain and crying and an immediate end to sex, but asking may well result in a yes and a mutually enjoyable experience, why would someone engineer an "accident"? (This is the logic I would ask anyone who doubts the existence of genuinely accidental anal.) The answer may well be "because he's an asshole," but remember he ruined his own good time here too. The key will be, is he willing to proceed more slowly to avoid future accidents? If yes, I'd give the benefit of the doubt. If not, the issue is that he doesn't care about Sister's enjoyment, not whether this particular mispenetration was with malice aforethought.
20
19- BiDan-- I'd argue that he isn't ruining his own good time. This is a guy who gets off on causing pain and not the good consensual kind of pain. He's pushing boundaries to see how often he can get away with it. Like all sorts of rape, it's not about sex; it's about power and aggression. Or it's a little about sex in that he's using sex to express his power and aggression.
21
A slightly off topic question: I'm puzzled, why would a woman ever enjoy anal sex? There's no G-spot in there and you don't have a prostrate gland to be stimulated, so why would a women enjoy anal sex?
22
@21 my guess is that the clitoris being much bigger as sometimes represented, there are sensitive parts not far away from the asshole (between the two holes in particular)
23
Following up on my post @17.

Small children when they're first being socialized will sometimes behave badly or break some rule and then offer an excuse by saying they forgot. Sometimes they'll hit their sibling followed by an immediate "I'm sorry." (They're adorable when they do this, but that's not my point.) Parents will ask pediatricians and other advice givers what to do in these situations because it's not unreasonable to suspect that the 4 year old really did forget or really is sorry. The parents don't want to punish unfairly. They don't want to punish at all. At the same time, they realize a responsibility to teach good behavior, to enforce fair rules, to socialize their children. You're not doing the kids any favors by letting them get away hitting, biting, lying or just forgetting. The standard advice is to give a consequence anyway. Don't put it in terms of a power play. Just teach the kids that actions have consequences. A child who has forgotten not to hit his sister will remember better if he's put in a time-out and given a loving talking-to about how wrong it is to hit.

Thus. Who cares if it's accidental or not? Actions have consequences. Mr. ANAL will remember better, he'll learn faster, if each instance of his "forgetting, if each "accident" is met with something he doesn't want to happen in return. And these consequences need to be harsh enough that he can't get away with a twisted logic that says "hmmm, one night on the couch and a 2 week break-up? Worth it."
24
JM @21
A slightly off topic question: I'm puzzled, why would a woman ever enjoy anal sex? There's no G-spot in there and you don't have a prostrate gland to be stimulated, so why would a women enjoy anal sex?

Slightly related data point: I'm a man and I sometimes enjoy receptive anal sex, but I dislike my prostrate being stimulated. So at least according to me there is enough to enjoy about anal sex without prostrate stimulation. "Filled-up feeling", nerve endings in the anus, etc.
25
Fichu @20: Maybe. Or maybe not. There's not enough to go on here. We just have ANALSLIP's word that D is such an asshole; it's not as if family members were never unfairly biased against partners, is it? And even if he is just as awful as she descibes, that doesn't preclude this from being a true accident.

Juan @21: What RE @24 said. That filled-up feeling. (Particularly if the guy's on the small side, and PIV doesn't give the sensation of being well and truly fucked.) The sense of doing something more "dirty" or "naughty" than PIV. Fulfilling a desire to submit or to be treated like a slut. Or just for variety. Don't forget we (or you) can also stimulate our clits while being fucked in the arse; those sensations combined can be amazingly intense.
27
@21 I can't really explain it but I'm a woman and love anal stimulation. If it wasn't more of a hassle to penetrate my ass than my pussy, than I'd prefer it over vaginal. It's a particular filled up feeling that really triggers something in my clit...bodies are interesting!

And generally, I know I can't receive full accidental anal penetration because there are times I can't get something in there when I really want to! The head of a penis causes enough "ow" even with lube and planning that this wouldn't work for me but again, bodies differ and it seems like some people have an easier-to-enter butt!
28
"Accidental" isn't really the issue, here, as we've all had the occasional "oops" – be it biting a little too hard or smacking your partner's nose with your foot (that one's particularly vexing!) or the old, "Whoops! Wrong hole" – dick where the sun don't shine thing. A considerate partner apologizes immediately and stops the festivities until the aggrieved party has time to lick their wounds. In fact, a considerate partner would lick their wounds for them. Sex is a contact sport, and shit happens. But if it happens (as this LW says) again and again, there's no excuse. Get out the asshole bat, 'cause this guy needs a good rap upside the head. Or better yet, stick it up his ass and see how he likes it.
29
I think Dan nailed it THIS time. I've had numerous incidences of accidental hetero anal, and yes, all were preceded by so much vaginal first that the whole area was extremely slippery. I have missed A few times at the start/prior to extreme slipperiness, but in such a case accidental anal penetration did not occur, thankfully. Simply not enough lubrication.
30
BDF @26
Don't forget we (or you) can also stimulate our clits while being fucked in the arse

Funny, I don't want my penis stimulated while being fucked in the ass. Too many sensations at once so that I can't concentrate properly. Then I miss out on both.
31
@21 on the rarest of occasions, i have experienced the elusive assgasm. i only ever knew of the possibility from a person that could only be described as a pencil dick, and it has only ever been something similar or close besides that, but it is possible.
i also presume that there was a bit of external clitoral stimulation due to the mechanics of the rubbing, so credit where credit is due...
32
@RE @30: Totally agree. I get all distracted with both happening at once. For similar reasons, I don't like 69ing. Can't pay attention to either and end up doing a bad job at both!
33
Someone must be at fault here.
No matter what. It must be someone's fault.
34
Abuse hotlines can be a great resource for family members, too! They will gladly talk you through the best ways to support your sister.
35
Sporty, if they are already having sex, then it's not in the absence of lube.

It can get very wet and slippery down there, the asshole is an inch from the vagina, the penis is built for penetration, the asshole is a sphincter not a wall, and some sexual positions involve loads of thrusting. Frankly, I can't believe why anyone would doubt that accidental anal is a thing, though of course body shape combos make it more likely for some couples than others. My guess is that the reason it seems unlikely to Dan is that most of these situations are not present in pre-asshole-penetrative guy-guy sex. The penetrating dude is not already thrusting in a very wet, slippery hole just an inch away from another hole, the penetrated dude is not already very relaxed and in a position to maximize receiving?

Shallow Skin, re: "if a woman is genitally aroused (and I would assume it's a necessary condition for piv) there is usually no need to be slow, gentle and shallow to start with, a deep single thrust is perfectly possible, can be welcome and very pleasurable."

As general advice, this is really bad, but if you mean in specific situations, that's fine. It's the "usually" here that's problematic. Some women don't need a slow gentle shallow start, others do. Loads of factors affect this, including personal preference, age of the woman, hormones, etc, as well as combos of dick sizes with vagina depths, etc. So for known partners and women who specifically ask for a hard initial thrust, sure! But I would advice against this being your go-to for a woman whose body you don't know yet if she doesn't ask for it. It takes me about three slow/shallow thrusts to comfortably receive full penetration, even if we're going to go on to have rough sex. When a guy does just thrust it in hard, it hurts, and the hurt doesn't stop so that the first few minutes of sex are painful and usually I'm done after that. Of course, I'm a big girl and can use my words (slow down, let me do it, now it's OK) and other big girls and boys can use their words as well for different preferences. I just mean statements like "usually this or that is not necessary" are never going to be good advice when it comes to differing bodies. As always, pay attention to your partner's responses.
36
@35 EmmaLiz: my expression was clumsy, not sure if it's possible to edit comments here.
I was trying to say that there is no absolute physiological need for slow, gentle, shallow vaginal penetration to start with, ie that the fuck-me-already-shove is *possible*, especially with high arousal. And it is, I think, rarely the case with anal. So, absolutely, not a general advice and not for a new partner, and I should have said *for me* and *with my average-dick sized RL partner* and mention that I do get very wet.
37
@35: “Frankly, I can't believe why anyone would doubt that accidental anal is a thing”

“Um, AHEM, knocking on the wrong door”

I think is a scenario people acknowledge here?

As described, the LW states her sister has encountered many no-lube, full extension penetrations where he wasn’t given a better angle and ability to see where he was going that suggests a pattern more than a simple “whoops”.
38
@33: “Someone must be at fault here.
No matter what. It must be someone's fault.”

There is a trend/fault for his patterns that he’s not addressing, I’m glad you’re mature, empathetic and balanced enough to acknowledge this.
39
@biDanFan no I'm not a shrink lol. Are u the comment moderator?
40
@37

I agree that the LW's specific case is questionable and (if it happened as described) probably not a whoops and definitely painful regardless. I was talking generally- the discussion about whether or not accidental anal is a thing which Dan discusses and which I interpreted Sportlandia to be commenting on more generally. I think in retrospect he was referring to this specific instance, so my bad.
41
@36

Yes, I figured that's what you meant, but I just had to piggy back my comment b/c the "usually" left it open to misinterpretation. I don't think it's at all unusual for women to need a slightly slower or more shallow start (at least for the first couple thrusts) just like it's not unusual for women to need extra lube, especially when we consider women as a whole- the majority of sexually active women are not young. Though to be fair, I don't fuck women so maybe my perspective is biased too heavily by my own experiences.

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