[Anal] Wrong Hole

[mickization]

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

[biglou]

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.

[thorntak]

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.

[whatnow3]

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.

[buddy i con]

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.

[captbobwi123]

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.

[alexossale]

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.!"

[carameldelight]

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.

[marcus63]

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.

[Mandy10]

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!!!