[Anal] Wrong Hole

[rickandsuzy]

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.

[willieone]

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.....

[clitty]

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.

[godlikechickposter]

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.

[jojo33bdx]

Originally Posted by ripstar1

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.

lucky boy !!!!

[jojo33bdx]

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.
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

[clitty]

POINTS!

[richyguitar]

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 ), 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…

[rednose]

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!

[bbdubluv45]

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.