[Anal] Wrong Hole

[seniornicks]

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.

[karlhein]

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.

[Barmixer]

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!

[thegrayprincejt]

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.

[jojo33bdx]

Originally Posted by thegrayprincejt

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 !!!!

[SlyBry2010]

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!

[toml]

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

[carameldelight]

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.

[Mark_2000]

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.

[carameldelight]

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.