Wrong Hole
 

I was wondering if anyone else was willing to share stories of when they may have accidentally entered the wrong hole .

Anal sex with my wife happens on a very rare occasion and it it treated as a special treat. But one day I was pussy fucking drilling my wife and got to the point of fully withdrawing then slamming back in which she loved. We were both humping hard. Unfortunately upon withdrawing I mis-judged my aim and went nuts deep into her arse.

The screech nearly took the plaster off the ceiling and she bolted to the bathroom in tears.

Me - I had an instant soft-on as in no way did I want to hurt her.

Needless to say our sex session went unfinished that night.

It took lots of work on my behalf before she let me go back in there.

Anyone else care to share?

My GF and I were out of town on vacation and having a great time. We'd both gotten pretty drunk and often when she gets drunk she gets pretty horny. This night was no different. We'd just finished a great meal and a fair amount of wine and some more drinks at the bar and were stumbling back to our hotel when she started being extra playful and coy.

We get up to our room and she's begging me for it. She wants sex so bad and I'm just not up for trying to fight whiskey dick when I know I'll be great and ready to go in the morning so I keep trying to put her off... when she tells me those little words no guy likes to turn down....

"I'll let you stick it in my ass...". Now we'd done it a couple of times before. 1 or 2 times with good results and 1 or 2 times with uhm... not good results. But here I am, drunk as a skunk and a GF so horny she's willing to give me anal.

Who am I to say no?... So I grab a big bottle of lube and squirt it all over her hole and plunge the fuck in. She's screaming into a pillow and clawing at the sheets. I did not give her any warm up at all. However, the whole thing was pretty hot and totally overcame any sort of WD issues.

'Twas not one of my finer moments, I'll admit and we both laugh about it now. If Anal ever comes up (and with our friends that's kinda often), she will find a way to retell this story, even though it happened several years ago.

---------------
A bit about sizing. I think I'm average (I'm guessing most guys think of themselves as average). 7" long, 5.5" circumference. I don't know if this is average, small or large. My GF is 5' 4", ~110 lbs. We just started playing with a new girl (5' 7", also ~110 lbs) and as such my GF said I can do anything with her, except anal (we are keeping that to just us). When I told our new girl this she looked at me, smiled and said, "When I first saw your penis I knew that you and I would never be having anal sex, so that's not really a problem." I do take that as a compliment but I'm also a little disappointed.

wrong hole
 

I was fucking my girlfriend at the time over the end of the couch, she had a really wet pussy most of the time and was a squirter I pulled out a little to far and pushed it back in and when I did it went into her ass, she squealed a little and said I was fucking her ass, I told her to hold that thought as I was almost done...
She complied and she decided she loved it in the ass!

The other wrong hole!
 

This is anecdotal at best so you'll see the humor. I stopped by this FWB's house one night unannounced. She was surprised to see me, but invited me in an explained she had a late date with a guy who got off work at 11 pm, so I needed to leave by 10:30 so she could get ready. I told her no problem, but wondered if she was up for a "warm-up round" before her date as I was suffering from blue balls and needed the release. She offered up a HJ or BJ, but I wanted penetration. She hesitantly agreed, said lets try this and tossed a tube of astroglide on the bed and got into position for lazy K9 on a pillow with her legs spread wide. So I get down behind her and start to push junior into her pussy but she squeezed her legs together preventing me from entering her pussy. She said "No the other one". Well, the light bulb illuminated in my brain - anal sex. I didn't even know she liked it this way. I lubed up junior with a few strokes with astroglide, pushed my way in and had great anal sex.

Afterward she explained her later date loved to eat her pussy and she didn't want him to get an unexpected cream pie and for him to see that her pussy had very recently been used.

So it was an unexpected delight which we repeated a few more times.

wrong hole
 

Yes it happen once with me and my wife, she was on her side with her back and ass twoard me, I was screwing her in that position and she was wet all over between her legs. I slipt out of her and rubbed my already wet dick on her pussy, when I thought that I was entering her pussy again I instead by mistake entered her ass with it. It lasted about a few minutes before she told me to take it out it's in the wrong hole. My wife doesn't mind me teasing her ass or playing with it but really fucking it is another story. I have only been in it once before that, during that time she let me do it for about a half hour, it was during a campimg trip we took together. She did tell me I'm the only one who has ever got her up the ass but not again because she doesn't like it at all. She wasn't very happy about it the second time and was a little upset about it although it was a mistake.

When my wife and I were first dating we were on a waterbed, her on top of me. I was going at it like usual and she was extremely wet. I slipped out while she was still moving and starting to rub her clit on my pelvic bone. I reached back and grabbed my dick, went to put it in her, and slipped right in. Something felt a little different, great just different. But I figured what the fuck and went onto completion. I finished, fell soft inside her and she says "did my ass feel good?"

I was amazed she just let it happen. No one but me has fucked her ass before or since, and every few years she will let me but complains about size. But loves to be fingered in her ass while I eat her out.

I had a girlfriend in university that wasn't on the pill and hated condoms. She used to love to 69 and lube up her ass and I would slide up and down the crack until I came. One time, I ended up in her ass. She immediately yelled to take it out - I had to ask her what hole it was. It was too short for pleasure.
The ironic thing is, she ended up going on the pill and ended up liking anal better.

Overheard
 

My younger brother is three years younger than me. He enlisted in the Air Force straight out of high school. There he met a real pistol of a woman and they married when he was 19 and she was just 16 (then legal in that state with one parent's consent). I was living with my father in a two-bedroom trailer house. The bedrooms were on opposite ends of the trailer. When my brother and his wife came up for a visit, I moved from my bedroom to the living room couch next to my bedroom. The bedroom door was only light plywood, as were the walls, so there was no real sound barrier.

One night I was woken by the sound of them making love. At first they were trying to keep quiet, but eventually they got into it and didn't care so much. They weren't talking, it was just her moaning. Then I heard her say, "You're in my ass!" in a kind of surprised voice. He hushed her and in a few moments later the soft moans started up again.

The next morning when they came out of the bedroom, she kind of sheepishly asked me, "I guess you heard us?" I told her not to worry about it. However, I guess they did, because I never heard them having sex again.

dp
 

We were playing one night with some swinger friends. normal rule was condoms and no anal. Carmel was on top of M---- fucking him when I had finished with M--- wife, We were watching them fuck when i saw that Carmels ass looked so inviting. While she was still fucking him I lubed my cock then entered into her ass. The presssure of my cock eventually pushed his cock out of her pussy after he had cum. I then cum in her ass. Next day she said it had hurt but she was enjoying it too much to tell me to stop.

Wrong Hole
 

This goes way back to after our second son was born. Dollie's pussy was still larger than normal so I could really ram it in and out full strokes. She was very wet and climaxing repeatedly. I think she was on her back with her legs over my shoulders. I wanted to bury my cock as deep as I could and that was the best way. From what I remember as my prick slipped in and out, our combined juices lubricated her ass hole as I fucked.
--About the same time I felt her hole tighen up she screamed. Wrong hole! But she never really complained and I must have butt fucked her quite a while before she told me I was in her ass rather than her pussy. I'm not sure rather it was the tightness or the thought of a new hole, I suddenly pumped her butt full of semen and kept hammering away as she screamed and held on tight to my neck.
After that we did it anal often. Sometimes accidental, but usually for fun. This continued well after our third and last child when her pussy was even larger after having pretty much everything inside removed. For some reason, as her pussy got larger so did her ass hole. So I could switch back and forth not really knowing which hole I was in. Later I realized this was unsanitary but we were both loving it so continued for many years.
Seems like her pussy and asshole both began to shrink back to normal and she couldn't take butt fucking anymore. Only recently did she start letting others fuck her. As five men took turns, three in a hole at a time, she tried the best she could to take it anal and oral. But over many years of surgery and having much of her colon removed she decided no more anal anymore. But she sure tried for a month or so recently.
So the wrong hole ended up being the right hole for a number of years.
I've fucked other women in both holes. Often making the excuse I must have accidentally hit the wrong hole. I'd say 50% love it.

Ex girlfriend
 

This ex girlfriend was a big time sl*tiest. Town bike-everyone gets a ride. Well only night we are in bed spooning and fucking. I pull out a little deeper than normal and when i go back into her i think nothing of it. Cant tell I'm in jer ass as she gets really sloppy wet. She turns to me and says you are fucking my ass. She didn't even blink or cry. Now I'm no john Holmes but a little bit more than average.

I later found out from a buddy she did anal sex before vaginal sex and has always had huys fucking jer ass. She was a big time sl*tiest and glad i got rid of jer. Great fuck but she was fucking crazy.

Happened once to me also....
 

My story is very similar to the others.... wife will not do anal at all... sometimes I can get a finger in when I am eating her out but if the head of the ol one eyed snake gets close to her anus she freaks out.....
We had been married for a short while when we got fooling around and really going for it.. I had her bent over the end of the couch and was jack hammering away at her wet sn*tch... I was pulling out as far as I could and slamming it back in at a quick pace. She was really wet and really into it....
Well, you can probably guess what happened next; I pulled out just a little too far and when I pushed forward, it went straight through the anal muscle and I was balls deep in her virgin ass. She screamed and I came and then I had to calm her down for about an hour as she couldn't move....
That is the only time I have been in her backside and although it was only for about 30 seconds, it sure was nice and tight..... :eek:

My wife has a pretty little a-hole... We can't quite do it, as even a finger can be too much. (I'm 6.5"), so there have been twice wrong-hole accidents that went no further than the head.

Now, an EX-GF of mine many years ago, she liked ass-sex a lot and I've poked her there many a time. One night - the wrong hole was going from BACK to the FRONT hole by accident. And both of us didn't know it as we were into at that moment... oops.

Like many on here, the one that sticks out in my memory was an accident.

I was 23, she was 30, I actually picked her up at work, she was playing on one of the tables I was dealing at, a few drinks after work, a long conversation and it was back to her place.

At this point, I should point out that she was way out of my league, i'm a tall, kinda scruffy 23 year old, she is a very attractive 30 year old with long blond hair and a body to die for, what the hell she saw in me I have no idea, but hey, not complaining.

Over drinks the discussion of course turned to sex, she had been married for a few years to a conservative type of guy, lights out etc, I made it clear that that was not my thing, if we were going to make love, then fine, if we were going to f**k then game on (damn how I miss being in my early 20's), she was fine with that, but did say that she had tried anal with her ex and had stopped before it went to far because it hurt, okay i'm cool with that, as long as I know.

So back to her place, a few more drinks, then the clothes start coming off. Yeah I am way out of my league with this one, what a body.

So we are messing around for a while, her on top, on her side, then into doggy, at this point I am pretty much wasted, to many drinks, in my mind I am a stud, truth is it was probably a disjointed mess, but hey, she seemed to be enjoying it and I know I was, and then it happened.

Like others, pull back and go for the power stroke, slip out and wrong hole it, i'm not a huge guy, right around 8", but a little on the thick side, she screamed, face in the pillow and I stopped, first thought through my mind, I am here with a stunning woman who is screwing my brains out and I just did the one thing she said no way to, s**t.

She takes her head out of the pillow, looks at me and says "is that what I have been saying no to, f**k me now"
I looked at her, said sorry, then said "let me pull out and go find a clean rubber"
She said "are you stupid, leave it there and f**k me"

Over the next 10-15 minutes I pounded her, she must have cum 5-6 times, I finally cum, we lay for a while, then off to the shower.

I again say sorry, it was an accident, she is giving me the dumb ass look, then tells me that she has never orgasmed like that before and she wants it again when I am ready. I ended up f***ing her for the next 2 days, calling off sick at work, it was insane.

This went on for about a month, then one night she drops the great news on me, she was actually still married and hubby was coming home in a few days, so thanks but it was over :(

I really didn't care, the more I got to know her, the more it was clear that she wasn't my type, but damn the sex was so good, I explained this to her and offered to be the man on the side, but she was having none of it.

lucky boy !!!!;):p:p:p:p:p

there many years, I spent a night with a work colleague.
I was 24 and she was 30 years old. It was a small brunette with dark skin, of Algerian origin. We were fucking for a while, she was kneeling on the bed and I took her doggy style.
At one point, I thought she was wondering if I wanted to change hole .... I said "oh yes" ... too happy with this proposal.
While continuing to fuck her in her pussy, so I started working her little ass with my fingers and then I approached my cock hard as a rock of her ass and I sodomized. :p:p:p
She buried her face in the pillow, his hands were clutching on the sheets, she stifled a cry, and let me enjoy in her, never tell me to stop ...

in fact she had only asked me if ...... I wanted to change position !!!!

oooopppsss :o

POINTS!

Personally I’m not even so much into anal, I definitely prefer a woman’s pussy over her tushy. However, the "anal question" has popped up with three different partners so far.
Years ago, I was having a love affair with a much more mature woman. It basically was a win-win situation for both of us; while I was extremely excited about pleasing this woman’s needs, she was enjoying sex with a fresh-faced, lecherous lover and we were going at it like rabbits at the time. She liked being on top in cowgirl position, but would usually lean forward on her arms so that we were face-to-face (or her tits-to-my-face :D), lift up her hips a bit and then let me do all the work. She got extremely wet during intercourse and one day when we were having sex in her bedroom, I was ramming her wildly in that position - my dick slipped out and, with my next move, directly went for her backdoor. My dick only went in a little deeper than the head for about a second, but it made her squeal out and adjust her position so that she could quickly put it back into her pussy. With one hand in her butt crack she kept moaning about it for a few seconds until we both burst out laughing and reached our climax a little later. Afterwards she told me that she had never allowed a guy to enter her backdoor and that she certainly knew why. Although the feeling had obviously shocked her, we had a good laugh about it after all.

The experiences with the other two girls (an ex-girlfriend and my current partner) were not accidental but based on the girls’ curiousness. Since I enjoy myself much more in the submissive role, I’m not really turned on by sex that is painful for the girl. I’ve never felt the need to go for the butt hole, and it wouldn’t have happened if it hadn’t been the girl’s idea. Both my ex-gf and my current partner came up with the idea that we should give it a try. My ex was curious about it, but eventually didn’t like it. Despite using lube with it, I had to push really hard and after a few, not even full-length, movements in and out she said it hurt her too much and we skipped that part once and for all.
With my current partner it’s been a more pleasurable experience for both of us. We’ve done it several times and she finds it quite exciting, though she needs to have her clit fondled in order to reach orgasm when doing it the anal way. The feeling of being a “naughty” girl is definitely a bigger turn-on for her in that respect than the actual friction. I know her pussy gets her going much more, so we usually concentrate on the things she likes most…

Senior Year
 

In my senior year of High School, I dated this girl exclusively. We would fuck anyplace that we were alone for more than 10 minutes. We were using my friends car one night, parked in a large parking lot near a playing field. She used a diaphragm and the jelly would really do 3 things; kill sperm, make her pussy very slick and make my cock kind of numb. This added up to a very wet pussy with a cock that could last for hours. So this night, I'm pumping into her pussy in standard old mish position, she moves to check out the window and my cock falls out of her pussy, I reach down to re-align myself, and I find my cock head near her ass. I say to myself "fuck it" and I ram my cock right into her surprised and virgin asshole. (now keep in mind, her head was jammed against the door and my feet were pushing against the other door. I had tons of leverage and THRUST) Needless to say, she screamed and even in the tight space of the backseat worked at getting away from my DICK. I pulled out, said "sorry" and slid it right back into her pussy to finish my ride.

Man I miss that pussy!

I've only used that excuse once...
 

I was fucking a skinny blonde from behind,and spied a pretty little asshole . I was already taking long strokes, so I pulled out just abit further, and rammed it balls deep in her ass. She was not cool with it, so I pulled out. And stuck it right back in her pussy. We both came, and we fell asleep, with my cum dripping out of her pussy.

Drunken birthday fun
 

Okay the story ain't about my wife but the girl I dated before her
My wife loves getting her ass fucked
You see I dated a girl named becky before my wife for three yrs
Now sadly not long after we started dating about a month she told me she didn't do anal
She said it's not me it's just she's never done it nor will she
She put off telling me for the first month by using the old I'm not in the mood excuse
But a month into the relationship she said she has never done it
And didn't want too as she thought it would hurt
I of course tried to convince her to just try it and see if she liked it
But nope she just refused which sucked cause she had an ass made for fucking
And I sure as hell wanted to fuck that tight chunky little ass
But was shot down anytime I tried
So one day about a yr into the relationship
We were celebrating my birthday with a few drinks at home
A few drinks turned into a lot
I was enjoy a few beers becky was slamming down vodka cruisers
They are flavoured vodka drinks for the record
So as becky slammed them down she got more pissed by the second
Cut along story short we started feeling each other up
She started giving me head
Then we started fucking
I bent her over the arm rest of the lounge
Now I was a tad drunk lol that I squeezed out way too much lubricant
And my dick was drenched in lubricant I slipped it in her pussy started pounding it
No after a few minutes I slipped out
I lifted her right leg and hung it over the lounge
Now as I went to slip it back in her pussy
My aim was a tad horrible due to me being drunk lol
And I honestly miss cued my aim and I slipped it in her ass
Due to the lubricant my dick slid right in her tight ass hole
I freaked expecting becky to go nuts but she didn't respond
She was that drunk and half out of it she had no idea
My cock was up her ass
My cock hardend so hard harder then it's ever been
Just the fact my dick was in her ass
I thought should I pull out or try to go for it
So I started to gently thrust my cock in and out of her ass
Going a little harder just to see if she would respond
Nothing but some mumbles and half moans
It's at that point I realised I'm in the clear
The next thing I'm pounding the fuck out of her ass and she was that pissed she had no idea
Then I started to feel my cock getting ready to shoot
So I started to think to myself do I pull out and blow on her back or shove it in her pussy and cum
Or just cum in her ass I thought fuck it I'm not pulling out I may never get the chance to cum in her ass
He'll the thought of being the first and only guy to fuck that ass not to mention cum up it
Was turning me on so much
So I kept fucking her ass and i speed it up and boom I cummed up that ass so fucking hard
I mean I have never cummed so hard in my life it was like a fucking tsunami of cum blowing up her ass
I slumped down on the lounge next to her I honestly thought I was in heaven
And thought to my self never have I had a better birthday lol

We woke up the next day on the lounge and she didn't recall anything
So I came up with an idea I was gonna get becky pissed every chance I got and I did
Thanks to her love of vodka cruisers I got a lot of anal the last two yrs of the relationship

But thankfully I'm now married to I women with amazing tits and an amazing ass
Who loves to get fucked rough up her ass daily and nightly
I couldn't be happier I feel for any guy who isn't getting to fuck a girls ass at least once in his life

Similar story
 

I have a similar story to report. This one came up on a road trip when the conversation turned to assfucking, so I apologize for third person, but I trust its veracity.

My buddy had been dating a girl for a while but had not yet sealed the deal. This girl was out of his class in several ways, both in terms of social status and general hotness. She was in med school and played college basketball, so my buddy was not only obsessed with getting in her extraordinarily fit pants, but was also looking forward to a life of making her sandwiches in the morning before she went off to earn a grotesque salary as a surgeon. Now, the curious part of this "hadn't sealed the deal" story is that it was not for lack of trying on HER part. She had never had sex before (and in fact had never kissed a boy before him), and was intent on having sex with my buddy, and they had tried several times, but they could not get her vagina to cooperate. Call it nerves, call it powerful sphincter muscles, call it what you will. There was No Entry Allowed. After a couple of failed sessions, she awkwardly confessed that this was a big problem every time she went for a gynecological exam. That shit was just locked up tighter than Fort Knox, and she did not have the combination to the safe. She was excited about sex and determined to do it, but some portion of her brain was just countermanding her orders and instructing her vagina to repel all invaders.

Anyway, one night they are attempting yet again to screw, and the lights are all off of course, because she is painfully shy. After an extended bit of poking around from behind, finally, success!! So my buddy is plugging away for a bit, when he notices that he seems to be suspiciously high on her ass. He sweeps down her asscrack with his thumb, and sure enough, he encounters his dong before he encounters her butthole. (Or I suppose he discovers them simultaneously. I won't split hairs.) And he's pleasantly surprised to discover this totally unexpected thing, but has no idea how to respond to it. So, as much as anything to simply play it cool, he continues with this unplanned buttsex.

And here is the amazing punchline to this story: This event is NEVER DISCUSSED.

That is the element which, in my estimation, puts this on the short list of Greatest Accidental Buttsex Stories Ever. I want more than anything to hear her side of this story, but that is sadly not possible. Does she know that he knows, or did she think that this was just her little secret in that dark room? I MUST KNOW, YET I CANNOT! Why do you torture me, Jesus?

But I've done a lot of contemplation of how this whole thing was possible, and I suspect that after three or four unsuccessful attempts to have sex, she was probably feeling like an unlovable loser, and was just desperately wanting to please her man. So when lo and behold it went up her ass, she was pleased to have any success at all in that arena, and decided to keep her mouth shut.

And, if you think about it, a 19 year old virgin's asshole experiences infinitely more stretching on a daily basis than her vagina does, so on some level, it makes perfect sense.

Finis.

Knock knock knocking ay the back door.
 

It was quite some time ago with a now ex-girlfriend. We were doing it the normal way and I slipped out and prodded her butt a few times. "If you're determined to go there get greased up." Well, I did and we did it. Interestingly different but enjoyable. We did it a few times again but the kinkiest was when I greased up and slid up her little rosebud while she was talking to a friend on the phone. She did well to keep a calm voice while I orgasmed up her poop chute. I do miss her.

oops
 

My wife gets very wet. This has led to the occasional oops moment when the head of my cock has slipped into her ass. To me it has always felt like her ass was made for fucking due to the ease of me slipping in there. Unfortunately she does not agree and she usually shoots off me like a bottle rocket.

The first time is probably the most memorable for me still. We had gone to bed (to sleep) and she was just wearing a t shirt. As I was spooning her, my cock just naturally nestled into her bare ass crack. Of course I was soon hard and she laughed and said “you can just take care of yourself tonight, I'm tired.”
So I was going to crank one out quick but then decided well there was a bare ass here. I started rubbing the head of my cock back and forth between her cheeks. It was feeling good and I would have been happy to finish and go to sleep but my wife was starting to get turned on now also. She shifted a bit so now my head could also brush along her pussy. I continued stroking along her ass to her pussy and back. When my cock parted her lips she was soaked, and as I kept rubbing it carried her juices up to her ass crack. She was soon quite slippery everywhere. She was soon pressing harder into me and I into her, including brushing right over her asshole. It was feeling so good I pressed a little harder on the next stroke and sure enough my head slipped right in. I've never seen her move so quick as she put space between her and my cock. She rolled over to face me and said “not there please” as she then pulled me on top of her for some good old missionary.

She has on a few occasions genuinely given it a try. Plenty of fore play, lube, talking and taking it slow but with basically the same results as the accidental moments. Once the head slips in, before trying to go deeper she asks me to take it out. She has said she knows it is in her head and she apologizes but it is not really a big deal to me as everything else she does for me is great.

First time for me and her was indeed an accident, but it was just a momentary "mis-thrust". Ex-wife and I were in the shower together, wet and slippery. I got behind her, standing. She was also standing with one leg raised a little higher, foot on the ledge for easier access. After sliding my hard cock up and down her entire butt crack, I thrust upwards, but aimed a little too high, and slid right up and into her butt hole. At first I didn't even recognize I'd hit the wrong hole as it slipped in so easily. She had not ever done anal before either, she was just very relaxed I guess. She did however immediately say, "Gentle, gentle, gentle". I got in a couple strokes, but we were both a little embarrassed about it, we'd never discussed it before, and I had no thought of doing it in the first place, so I just pulled out. It was easy to wash my cock off and get back to our original intent.

A couple years later though I purposely switched holes when we were going at it doggie style. She was wet, and my cock lubricated well enough that it again slid right in without much resistance. She again said "Gentle, gentle, gentle", but this time I kept going until a shot my load up her ass. It was apparent she wasn't real pleased by it all, but she didn't stop me. A couple weeks later I tried again, but this time the "door was locked", so to speak. She got up and went to get some oil exclaiming, "this might work, this might work", emphasis on the "might". She clearly wasn't very enthused to do it, but willing to let me try. I dumped my load up her ass again, but that was the last time we did anal. Our marriage was already going downhill by then, and about a year later we divorced. It had nothing to do with the butt sex however. I have no pictures of either event -- she was NOT interested in me taking pictures of her naked, much less having sex.

The only woman I've had anal with is my wife. We were in our mid 20's and I came home with an alcohol buzz. We wound up in bed having sex in the missionary position and I was really pounding her. I came out of her pussy and urgently pushed to get back inside. I missed and hit her asshole. She didn't like it and I quickly reentered her pussy. The next day, when I was sober, we had a talk about anal sex. This was something new for both of us. Over the next few months we played around with me using my tongue and a finger tip on the outside of her ass. Sometimes she'd do the same to me. We discovered she really enjoyed having her ass played with and having one of my fingers up her ass. Soon we decided to give anal fucking another try. We used lots of lube and I took my time but she always found it too painful. We gave up on trying to get my cock in her ass but she still enjoyed having my finger there. More time went by and one night we came home together but this time it was my wife who had the alcohol buzz. OK. It was more than a buzz. She was pretty drunk. We went to bed and started having sex. I was fingering her ass when she said, "fuck me". I started entering her pussy when she said, "No...in my ass." I lined up with her asshole and slowly started pushing. It took as least a minute or two to get past her sphincter but when I did it went all the way in. I loved it and, best of all, she did too. I dumped a load inside her. We never got into anal sex on a regular basis. When she was sober she always complained about the pain. But once or twice a year, when she got a pretty good load on, her ass was open for business and we both loved it.

Before we got married my wife and I used to do anal pretty fequently (she was terrified of getting pregant and wanted to wait till we got married) afterwards it dropped off in favor of good ol' pussy banging. However, a few weeks ago we were going at it in the living room. She was sitting down and I was standing infront of her as she sucked me off. Eventually all clothes are thrown around the room, as I pulled off her panties I could tell she was soaking wet, and she had my cock pretty well covered in slobber. She turns around, kneels up on the couch, with her face half burried in the back of the couch, half looking back at me. So i mount up, after a bit she starts bouncing too...then I slipped out and poked her ass. Didn't penetrate but she jumped, I said "Oh, sorry!" She said "No, it's ok, I just wasn't ready." i thought "...she wasnt ready? Is she ready now?" So I played it safe and let her decide. I put my cock up to her ass, and lo and behold, she pushed back onto me. It felt like an eternity as she slowly slid back. Once her tight little butt hole got past the head I felt her relax a little. Once she was all the way back I started rocking back and forth, before long she was reaching back with both hands pulling her cheeks wider and yelling "Deeper, oh god, I forgot how this feels!" Afte we were done, I mentioned about maybe getting a toy involved, she didn't understand my meaning, so i explained, "Me in one spot, toy in the other." Her eyes got big and said "I don't know if I can handle all that.!"

post pregnant wrong hole
 

This was about a month after my wife had given birth to our first child. We were both in our early 20's and had been fucking each others brains out 3 to 4 times a week. Her pussy was still tender from child birth and she didn't want to risk getting pregnant again so soon but we were both horned up. We were in the shower rubbing on each other and a month of no sex was affecting both of us. We had anal sex a few times in the past but only when she was drunk. I suggested anal in the shower and she was down with it. She bent over and I started working my dick inside her ass. The more relaxed she became the more she started arching her back to the point where I was almost thrusting down into her. For support I grabbed her hips which spread her cheeks and opened up her pussy. I was fucking her hard and was almost coming completely out of her ass before plunging back in her ass. On one stroke I came completely out of her ass and because of our position plunged balls deep in her tender pussy. She yelped and moved away. After she recovered I sat on the edge of the tub while she rode me with her ass to make sure there weren't any more accidents.

I was seeing a married girl for about 2 years. When she got a little tipsy she'd let me play with her asshole and on occasion she would get on top and slip my cock out of her pussy into her ass. She would always say, God it feels so good.

One time she had stopped by my apartment after getting off work and we drank a couple of beers and then went into the bedroom for some sex. So, I usually went down on her and got her off, then we'd fuck. So, I eat her and then get behind her doggy style and slide my cock into her and start pumping away. We were getting more and more into it and I'm pounding her pretty hard when as I'm pumping away my cock slips out and slides directly and fully into her asshole.

She immediately screams out and crawls to the corner of the bed and is crying and says, You did that on purpose. Well, I didn't and couldn't convince her that I didn't. But, since I hadn't got off I asked, Do you want to finish? She screamed at me, No I don't want to finish!

She did recover although for about a week she wouldn't let me anywhere near her ass.

Yes I have had this happen to me quite a few times, I get like a slip-n-slide during sex. First time I ever had it happen to me was with a fwb and we were intoxicated and we were using restraints so I was tied down face down ass up and he was hammering away and came out and he went to put it back in he got the wrong hole and slammed and went right back to hammering away and it took him a couple mins before he slowed down long enough for me to tell him he was in my ass. He asked if I liked it or not and told him it kinda hurt because he was very well endowed in both length and girth as he is still slowly screwed my ass. He asks me if I want him to pull out or what and by this time I've adjusted to his penis and it was starting to feel good so I told him he is already in so he might as well keep going and it's feeling pretty good. By the time he finally came in my ass almost 45 mins had passed.....needless to say whenever him and I are around each other when we are drinking he gives it to me in the ass and I love it!!!

Only once - accidentally...
 

Fucking Jane doggy style I got to the hard and fast strokes when I slipped out - then in to the wrong hole. She jumped a bit and I apologised. She said no need to say sorry and did I mean to do it?, in a way that made me think she was up for it. So I slid my cock down between her cheeks and nudged my way in to that tight little hole. It felt great, tight like pussy only feels when cumming. She moaned in an approving way and pushed back, I was having my first anal fuck. Anal became part of our usual sex and the best was when she would do herself with a vibrator in the pussy. The feel of the vibration with the tightness of asshole round the cock is truly amazing, if you get the chance take it. It also means she gets double penetration which I believe is popular amongst the ladies.
We parted eventually and my now wife is less keen. She needs to be very drunk and very aroused, also very wet - to slip in easily- down there to let me enjoy her little brown hole. Shame.

Not wrong hole, but anal related and funny. I had met a lady on-line. Had done a lot of flirting, exchanged some pretty sexy talk, and she had sent me a picture of her goodies. We arranged a weekend to meet in a city part way between where we lived. We met, had drinks, decided we liked each other, and retired to my hotel room, were we had several nice fucks that night and during the next day. She was fun, nicely multi orgasmic and pretty cuddly afterwards. The next evening we went out to dinner, had some wine, and came back ready to have another go at each other. We did the usual warm up activities, kissing, hugging, eating/sucking, fucking. Then I began to use two fingers on her pussy and began to probe her butt with my thumb. This went on for a while, and she seemed to be pretty well warmed up. I slid behind her, took a couple of strokes in her pussy to get my dick nice and wet, and pushed gently into her bottom. She pushed back, and soon I was balls deep in her ass, humping away. It went pretty well, she came, I came, and then relaxed against her, with my dick still deep in her bottom. Just at that moment, at the very moment that I had finished cumming and relaxed in her, her phone chimed......ta da.....it was the alarm for when we were meeting the night before. Broke us both up laughing.

We lived too far from each other to have a regular thing, but we did meet a couple of more times, including a threesome with another fwb that she had, her first 3 some. Most visits included at least one round of butt sex, and a dp during the threesome, a first for both she and I. Hate to admit to being the smaller guy, but in a dp, often the smaller guy gets the butt, so it wasn't all bad.

I have a friend who used to travel on business. On one of his trips he met a woman, and after a couple of drinks they went to his room. She stripped his clothes off, sucked him to get him hard and wet, then stripped and knelled on the bed with her ass in the air.

Suddenly, she yelled "fuck my ass hard". He plowed into her and she fucked his cock. Turns out this is the way she likes it. On all his trips he never fucked her pussy!

My ex
 

I had an ex who was an anal addict. Shed be riding me and "wrong hole" her self. Apparently shed had a few exes who were squeamish about actually penetrating her backdoor. So she started wrong holing herself to get her fix.

lucky man !!!! :p:p:p

Wrong Hole and Unintentional
 

Later in our relationship, my third wife was pretty into anal (see "Videoing Wife Leads to More" in this section) and could easily accept me in her ass with just her copious pussy juice for lube. Trouble was, outside of the squeeze from her sphincter I didn't get much sensation so I hardly ever came when in her back door.

One of the last times we actually fucked before all went south was different. I had her bent over the side pf the bed and pounding her pussy from behind. Eventually I pushed her all the way down on the bed and then I stretched out over her, laying mostly on her back as I continued to thrust in her. As many others have related, I got fairly vigorous and popped out of her pussy. Just a few wiggles later I was back in. She grunted a bit more pointedly as I resumed my efforts.

After a little bit, her fingers on her clit did the trick and she came. I was really enjoying the squeeze on my cock as I weighed her down and compressed her ass globes and all. Soon it was my turn and I grunted out my orgasm as my cum splashed her insides. As I relaxed and slipped out, she rolled to the side and gave me a look. "You know you were in my ass, right?" HUH? I said sorry, because I always either cleared it with her beforehand or she initiated it when we went there. Not sure she was convinced, but I guess it didn't matter as we split not long after that.

Some years before, in happier times, she and were still early in exploring our anal fun. We had spent a long night just doing everything we could think of and finally we ended up with both of us on our knees on the floor, her holding onto the couch and me behind her.

I was rubbing my cock up and down her ass crack and pussy and then focusing on rubbing my cockhead on her wrinkly asshole while I used her wand vibrator to buzz the shaft of my cock and her pussy. It took a bit but finally I felt the cum boiling up.

I was now kind of thrusting my cock in my hand and bumping her asshole insistently while the buzz brought me to the peak. The first shot of cum out of my cock splashed her asshole pretty thoroughly and the next jet coated my cockhead. With the next bump against her hole my cock popped right in.

I wasn't so far out of it that I didn't know what happened. I thought I ought to get out out of there but she pushed back on me so I continued to thrust in her hot hole while a long night of cum build-up literally hosed her insides. She came immediately and then again as I slowed down the thrusting and squirting.

After we calmed down she said it was okay- just surprised her. We never repeated and I'm not sure why not!

Reminds me of the song
 

Sorry, I don't have a story, but I can't believe no one has posted this here yet.

//www.youtube.com/watch?v=-zHVW7Zy_vg

wrong hole and unintentional
 

My wife and I are not strangers to anal sex. She likes her ass fingered while I'm licking her clit to get her off hard and get her pussy nice and wet. On this night her asshole was more relaxed than I can remember it being, easily taking 1 finger right off the bat so I went to 2 fairly early. By the time she got off I had 3 fingers up her ass.

The kids weren't at home but were going to need a ride soon. Normally we start off in missionary but for whatever reason she started off in the leap frog position. I slid into her pussy and started fucking her hard but because of the position slipped out of her pretty quickly. I grabbed my dick and slid back inside of her in one smooth stroke but when I was about half way inside she said something about needing to be quick. Since I had gone inside her in one stroke I thought she was talking about needing to be quick because of the time so I started fucking her hard again. She was a lot louder than when we first started and something felt different so I reached under her and found her wet, dripping pussy hole empty. She has her head in the pillow to muffle her screams and I'm trying to cum soon before we need to get the kids. About the time I find the sweet spot that is going to get me off her cell rings and it's downstairs. I'm balls deep in her ass so I'm not stopping to let her get up to answer it so when it stops I was hoping it was a wrong number. When it rings the second time I'm cumming in her ass and she isn't about to jump up and make a mess. The third time it's my cell phone ringing but it's in the pocket of my jeans on the bed so I don't have to pull out of her. I answer it and of course it's the kids wanting a ride. I have my wife with her freshly fucked ass full of cum put her clothes on to come with me to the church to pick them up. She walked a little slower than normal and clenched her ass when standing and making small talk with the pastor but made it back home without staining her panties. When we got out in front of the house she was clenching extra hard and as soon as we stepped inside the house she made a bee line for the bathroom.

Couple of stories.

With the wife. After a night out drinking we strip and hop into bed. I cuddle up behind her and start pressing my cock against her ass. I reach around and start to massage her clit. She responds and presses her ass back against me. After a couple of minutes my cock penetrates her.

She lets out a gasp and says.

“You know your in the wrong hole.”

“Oh, should I take it out?” My reply.

“No, since your already in, you may as well finish.” Came her reply.

I fucked her ass and deposited my load in her. Luckily my wife loves spontaneous anal as much as I do.

With a girlfriend

With an old girl friend on our 3rd date. We were fooling around in the shower when she suddenly said.

“I want to do it.”

With that she turned around and placed one foot on the ledge in the shower and waited for me to penetrate her. I reached down with one hand on her pussy to guide my cock to the entrance, I was poised to penetrate her. At that moment she reached back and pushed my cock back. I responded and pushed my cock forward again. She just pushed my cock back again. She then turned her head and said.

“No, I want it here.”

As she pressed my cock up into her ass crack.

I stupidly said.

“Isn’t that the wrong hole?”

She looked at me and just turned her head away. It suddenly dawned on me that she wanted me to fuck her ass.

I pressed the head of my cock up against her asshole. As I pushed with increasing pressure she responded by pushing back. But her asshole stayed tightly closed. Her breathing had deepened and as she breathed out, she forcibly pressed back and suddenly her asshole yielded and my cock head entered her ass. With that, I pressed onward. She then let out a gasp and reached back and pushed on my stomach and said.

“Stop.”

So here I am with my cock stuck in the vice like grip of her asshole, wondering what next. With that I could sense that she had started breathing more heavily and on each breath out, I felt her ass relax. She took her hand away and started to press back against my cock. As I pressed forward she would then pull away from me and as my cock slid out of her ass, she suddenly pushed back again. Causing my cock to go deeper on each subsequent thrust.

The tightness on my cock was incredible. I watched my cock sliding in and out of her ass. On each thrust in, her asshole would be pushed in with my cock and on each withdrawal, her asshole would cling to my cock and stretch back, before it released it’s grip and allowed my cock to slide out.

After 5 minutes of ass fucking I came on her ass cheeks.

public wrong hole
 

Just a few weeks ago I had another wrong hole incident. We were coming back from a ride in the country one evening when my wife started stripping off her clothes unexpectedly. I started playing with her wet, hairy pussy while driving and when I saw a car wash I pulled into a bay. She didn't ask any questions, she just told me to tell her when I was ready. I went to the front of the car, she got out and I started taking a few pics. After I was done she was still bent over the car wiggling her hips at me so I pulled my dick out. Because of our height difference the first hole I found was her tight, dry asshole and as it started to open around the head of my dick she let me know I wasn't where she wanted me.