How Many Times Have You Fingered Your Wife's Butt?
 

Let me first say that, yes, I have provided some pics of me fingering my wife in her butt. They're in my album "Anal Fingering."

My wife loves getting fingered in her butt. She's been able to climax from it for several years now, and she really loves it when I finger her butt while she's riding me reverse cowgirl.

So to answer the question, I would say I have fingered my wife's rectum a good 200 times so far in our marriage. I have butt-fingered her to climax probably 20 times.

How about you?

Only a few times
 

She finds it too distracting and it can ruin her orgasm.

Not very often really. Ass play in general doesn't do too much for her sexually, not that she's too prude for it, it just doesn't enhance her cumming - breast/nipple play, choking, and hair pulling yes, ass play no. Now she still lets me eat her ass from time to time for my pleasure, I'd say once a month for the last five years or so so maybe 50-60 times I've done that. But if I'm going to do ass play I'm going to feast rather than finger. I've probably only fingered her ass about 3-5 times.

Well, here's some advice.

The first time I tried to stick my finger in my wife's butt, we were in the middle of having sex. She didn't like it and pushed my hand away. On many previous occasions, she had let me rub the outside of her butthole during sex and had enjoyed that. So I figured I would try just sticking my finger in her butt just a little bit. But, like I said, she didn't like it. She said it distracted her.

But, my wife really likes to please me. When she understood how much I wanted to finger her butt, she said she would give it a try. (I should add that at that point she had no idea that I was hoping to buttfuck her one day!)

The next time we were having sex, I was on top and she had her legs pulled far back. I reached down with my right hand and started to rub the outside of her butthole and made sure there lots of lubrication. Then I took my pinky finger and started to super slowly try to gently push it into her butt. On the third of fourth push, the tip of my finger, like not quite a quarter of an inch, slid into her butt. I didn't try to go in farther but I just gently moved it back and forth sideways/horizontally. I left it in her butt for about 10 seconds and then pulled it out. What a wild feeling! Afterward she said it didn't bother very much because of how gradually I slid it in and because I didn't try to go in farther.

After a few more times, in that same sex position or with her riding me, she got to the point where she didn't mind if I put about half an inch of my index finger into her butt. She was still able to climax. She said she actually enjoyed it. And my wife is rather petite. She's barely 5'2".

As I said so now she really gets off on anal fingering. I can stick my middle finger all the way up her ass and rub it around, and she enjoys it. Hell, she can climax from it. She especially likes getting buttfingered when she's riding me reverse cowgirl.

So the trick is go use lots of lube, to use your pinky finger at first, to start pushing it in really slowly and gently, and to be very patient and gradual about going deeper into her ass.

My experience is similar to Mitch. What started our anal experience a few years ago was both of us started rimming from time to time. It felt so good to her that I'd then push my tongue in as far as it would go which could only happen if she relaxed everything. So the next step was to use my pinky right after the rimming then moving to bigger fingers. She's not had an orgasm that way but certainly does regularly when that's combined with regular oral sex.

Indeed, now if I don't put a finger in while we're playing or when she's masturbating she'll insert one of her own. it's become a regular part of our bedtime fun for both of us. Need to be careful of long fingernails, though.

Always, always, lots of lube, in our case Albolene, needs to be used. I'm thinking of buying a set of increasing size butt plugs. Any suggestions?

I'd love to get her to try ass fucking but that's still off limits.

My wife was not ever into anal play in any form for many years. It was something she was not even wiling to try. Then after our first encounter into the swing lifestyle and hooking up with a single guy while things were happening he ended up fucking her in the ass. She was far to into everything that was happening to protest and despite pain at the start she ended up climaxing with him inside her ass.

She made a very good lady friend in the lifestyle about two years later who she experimented with girl on girl sex with but became very close friends. They talked about sex and what they liked and even did the girls weekends away thing with. Talking to another girl she broke many areas of things she considered taboo and the two of them often watched porn to pick up on new techniques.

Now, my wife is pretty open about liking sex and liking various forms of kinkiness. Anal is one of the areas that she now openly enjoys. Her favorite is MFM with DP and even DVP when the other guy and I can get that close and it not be weird. She will also tell me when we are alone and having sex "Fuck me in the ass" which I think is incredibly hot, at least for me. She also will tell me to sick a finger in her ass or to use a toy on her ass while we are fucking. She brought a toy that has a ring for my cock and balls to slide through and then has a large dildo mounted above to provide her with DP when we are alone. Depending on her position she can either have the larger dildo or me in whichever hole she chooses. She likes it but still says it is not anywhere as good as the real thing and having two men.

Her regular boyfriend loves to fuck her ass doggy style. He says it is the hottest thing he can imagine. He also loves to eat her ass and get his tongue as deep up inside her as possible. Pic 3 is of her tight little hole after he just ate her ass and is getting ready to fuck her.

Pic 1 is him inside her ass

A pic of few of her toys including two anal plugs she enjoys when we are alone.

It's very easy to have wandering fingers during oral sex. Somewhat surprisingly, she's the one who started it in our relationship. She had read/heard somewhere that rubbing there enhances a guy's orgasm. It took a little adjusting, she was a bit agressive at first, but eventually it became a very enjoyable enhancement to her going down on me.

I started returning the favor, again gently, and it certainly seems to enhance her pleasure. It's great when she is on top of me in 69 and I can watch as my hands pull her cheeks apart and my fingers dance around her ass slowly adding more contact and more pressure. She does gasp any time I actually penetrate her, but we do usually keep it to a shallow tease.

My Mrs likes a small amount of finger or thumb (fist knuckle) up her arse while I'm fucking her doggy or while she's riding me.

Recently she agreed to try anal, but even well lubed she decided it wasn't going to fit and I needed to stick it back in her pussy.

142,372 times.

My wife does not like it - says she can't concentrate on 2 things at a time. Lately though when we shower together (which is fairly regularly) she will wash my cock and balls, and make sure my butt is clean. She has taken time to finger me as she gives me a reach around. She likes to feel my cock get hard as she does it.

Also she told me she had a dream that I was fingering her ass and her pussy at the same time as she walked down a set of stairs. Perhaps she is coming around to letting me do it. She said she had a big orgasm during the dream.

Before we got married anal was frequent, but after it totally disappeared, that is until a few months ago. While fooling around one day we were spooning and she held my cock up to her ass and asked "you want to put it in my ass?" Naturally I obliged and ever since then there has been some sort of anal play. Typically it comes in the formorning of fingerings(or thumbing if doggy style). She told me just last week that she loved the feeling of both holes being played with :)

My wife never liked butt play but after a while she has loved anal, loves DP, she cums hard from it. Next step is to get her to go out in public with a chrome butt plug in her.

not my wife I butted
 

I've only fingered my wife 2 times but the last time was a couple years ago. My wife said she did not enjoy me fingering her ass and if I wanted to finger anything it has to be her pussy. If I wanted to finger an ass I would have to go find another woman that would allow that. I literally took her advise and fingered my massage therapist's butt 4 times in 2016 and twice this year. I'm 55 and she's 43 so I get the feel of a younger ass in addition to another woman.

I never expected this thread that be relevant to my wife and me, but last Frida, we both got a good bit wasted, went to see Phantom (touring Broadway) and had the wildest sex of our 12 year marriage. I fingered her puss and ass at the same time on two separate love making experiences that night. She had three orgasms (personal best for me) and I had a nice case of whiskey dick going on, so I lasted nearly an hour the first time. Room service interrupted the second. I'm sure he knew what was going on because my hair was a mess, I only had on my suit bottoms and undershirt, the room was dark, it took me a while to answer and my wife ran to the bathroom right before I opened it he door. I tried to get her to just lay naked on the bed and pretend to be asleep. She considered it because I had her so aroused, but folded when the time came.

She absolutely loved the anal fingering! The second time I was fingering both holes and gently slapping her pussy too...she moaned a lot and asked me what I'd been watching to learn it. I said I'd known a few tricks for years, but I never expected her to let me use them lol. She's a prude and doesn't like to get too wild. She said we may have to try some new things now though! I'll certainly try if she will let me!

About 1/2 the time
 

I play with her asshole about half the time when we have sex. Officially, that's a "one way street" to the lovely prude wife. But when I'm eating and fingering her pussy, and put another digit in the right spot, she'll lower herself or push herself onto it- all under the guise of just responding to the fingering and oral of course. The other day, I was toying her pussy and opening that hole up pretty good, and actually finger banged her ass pretty good - much more blatantly that the usual routine of kinda sorta' sneaking it in - she came hard and long. Her body enjoys it but she can't admit it out loud. She won't let me indulge in rimming her outright though, I just have to sneak a little in during oral.

The wife loves a finger, fingers, cock or tongue in her ass. Here are a few shots of various playtimes she has enjoyed some anal fingering.

I don't have an exact number...
 

But maybe 2- 4 times a month? If she's on her hands and knees, she is most likely getting a thumb up her ass. Missionary, I like to grab her ass cheeks and slide a couple fingers in. She says she prefers to not have anything to do with anal, but she cums really hard with a vibe or butt plug in.

She doesn't like to have my fingers deep into her ass...

...but, she does love when I caress her anus and make pressure on it; pretending like I want to get my fingers in, but without actually doing it.

We can be doing that for minutes and she usually asks me to continue doing the same but using my penis. She makes me cum with only her butt cheeks. It's great, because there is no poop (let's admit it; even if it is super clean, there will always be poop; it's its function).

If your GF/Wife doesn't let you finger her; start with something like this. She won't feel as "invaded" and will let you go deeper from time to time.

NHead says No, Body says Yes
 

My Mrs will say she doesn't like Anal play and in the past has pushed my hand away but about half the time I will finger her a little. I think that if I don't do it to often she'll miss it.
The best technique is when I give her oral on her clit very lightly and I have my finger stroking her pussy lips on the outside. There's plenty of lubrication and as I move my finger up and down I move down a little further each time slowly teasing. She responds and lifts up so my finger is just on her butthole. I'm careful not to be too pushy and let her do the work and she pushes onto my finger more and more. I get to the stage where I'm not touching her pussy, just breathing on it but the tip of my finger is in her ass up to the first knuckle and she orgasms really hard as a result and in the middle of it pull my face into her pussy.
It's definitely the ass fingering that gets her off.
However she doesn't like anal play so we never discuss it, it just happens.

anal fingering
 

My wife was a little shy about anal. When we first got married she would let me fuck her ass once a year but didn't like anal play when we were fucking even though I kept trying. Then she found out how much she liked having her ass played with while I was going down on her but was still hesitant about letting me because she thought I would want to fuck her ass later. When she found out I wasn't going to fuck her ass every time I played with it she became more receptive to anal play going as far as having a bottle, a flashlight and the gearstick up her ass just for the fun of it. Now she expects to get her ass fingered when I go down on her so she can get the orgasm she likes. I've had as many as 4 fingers up her ass while licking her clit but all she cares about is that orgasm.

Sometimes When We First Started
 

having sex, if my wife was lying on top of me, I would gently rub her juices around her anus and then insert a single finger, usually no more than one knuckle deep. At first I would just hold it there. Then I would start to rock it in and out, some in unison with my cock, other times in opposition to it. She never said anything pro or con about what I was doing. She had several times told me that she found the idea of anal sex disgusting and not to ask for it.

After a couple of years it was clear that she was merely tolerating what I was doing, she never reciprocated, so that aspect of our lovemaking eventually drew to a quiet end.

I have tried
 

She says No to anal.
When I have fingered her asshole she finds it too distracting to have an orgasm.

Ex enjoyed a finger in her ass when we were fucking.

Current wife enjoys finger, vibrating butt plug, and I get anal once every few months or so. The guy before me got anal almost exclusively, but she said his dick was small and it was really the only thing she enjoyed about sex with him. I'm nothing too impressive 7.5-8, but pack what is allegedly odd width.

My wife is usually very dull in the bedroom. But I've discovered the one kinky thing she goes for is anal play. Every time I lick her pussy, she allows me to insert a finger deep in her ass. I probably shouldn't tell this part, but when I stick my finger up there, I'd say half the time I bump into her poop. I push it around for a while and dig my fingernail in. Then I'll pull out my finger and show her the brown. She'll moan with excitement and beg me to put my finger in my mouth, so I do. Then I'll stick my finger back up her ass, lick her pussy more and in short order she has a killer orgasm.

First wife many times, she also liked dick in her ass. The second one somewhat liked it, but not always. My wife now, not at all.

My wife likes it
 

But only some of the time. She has never objected if Inhave done it while fucking. One night when drunk and playing a bit Dom, she told me to "stick your finger up my arse while you fuck me. And don't you dare cum till I tell you to."

Two or three times she has let me fuck her arse, something she never let exes do in spite of at least one begging!

She likes it
 

It took a couple of years to get on to anal. It was a very occasional thing. As she has aged she has become more interested. I insert a finger or thumb when I go down on her. Moving it back and forth drives her over the edge to a strong orgasm. This is a regular for us. She is quite particular about what she has up there. She has no real interest in butt plugs, although we have a few. However, she is really into anal beads, plain or vibrating. Current favourites a long 11inch set and graduated vibrating ones. With the latter, she has reached a dozen orgasms while I fuck her. She will also cum during anal sex, as long as I play with her clit.

She likes it
 

My Mrs. really likes it and it has added a new level of excitement to our love making. She is not thrilled with the idea of full anal but who knows. Maybe someday.:)

More than I can count.
 

Actually, I do it every chance I get.

Many times - sometimes to get her over the edge while fucking, sometimes to make her even more fiull while fingering her pussy as well. She's cum hard with 4 fingers in each hole more than once.

But hates anal fucking.....

A lot over the years... our first ever date I had her mostly naked with her big tits in my mouth and two fingers up her ass in her living room floor while her mom slept in the next room.

the position
 

most often when i am going down on her or we are in 69. From a 69 position, with her on top, it is so easy to have hands free to explore and probe. The thing that i truly enjoy is in that position she will often return the fingering too.

I always have the desire to press a finger into her she is on her knees and i'm taking her from behind doggy style, but more often then not that is the position we use when we don't have time, or she's already cum and wants me to finish.

Mine will let me rub her ass hole, but won't let me finger it. There was only one occasion that she let me stick the head of my dick in it.

Lisa likes hers rubbed more than fingered too but she will let me when she is horny enough. I usually do it when she is on top. it's easy to spread some of her wetness and then ease a finger into her as she rides me. I've also done it when we are going at it doggie style.

On an ass related note she also found out she likes the occasional analingus. I was going down on her one night with her ass propped on a pillow. I ventured further south first licking around her rosebud before going for it. With my fingers working her clit I think she was surprised at the pleasure of that orgasm.

Knocking on the backdoor
 

Lots of times since she like a finger back there specially when I am eating her out. Always wait until she is dripping a lot, or wet my finger(s) in her c*nt before going to the back. Never dry to make it uncomfortable. That finger(s) will be the backside one until we are finished. Never mix the backside and the frontside while we play.

Besides the thrusting, she like my curled finger pressing back out from the inside. Scissoring my fingers apart to stretch her opening some. She has a favorite smaller vibrator she likes up there when she's in the mood for something larger back there. So sexy when I DP her with that vibrator and a larger dildo in front.

My fantasy would be her DP with two regular size dildos, or a VDP with the two. But she is not as adventurous as her younger days. ;)

New level of orgasm unlocked
 

I only recently and slowly introduced wifey of 20 years to anal play and fingering. She had always been totally against any butt stuff. While working her with her vibrator I started off by placing my forefinger on her ass whilst my thumb worked her vagina. No reaction. Once she was used to this ass touching as part of her “treatment” and over time I would put a little lube on her butt and ever so slightly massaged her butt in circles from the outside whilst giving her clitoral orgasms with her vibrator. Did this so she would associate orgasm with butt massages. Her concentrating on her orgasms gave me space to play with her ass. No objection as I massaged her butthole a little stronger each time. I would apply much more pressure on it as she approached orgasm up to where her anus slightly opened and I was lingering in her entrance. Sometimes when I varied the pressure she would push herself back against my finger. No penetration yet but great orgasms. Afterwards she would not acknowledge that I was now unashamedly working her butt. She just acknowledged how good the orgasms were and said that I was a “magician” for making her cum like this not mentioning the apparent role my but play had in this. 😇😂 I also said nothing as she obviously did not want to talk about it. Just continued playing with her butt every time. And then one day as the sexual tension felt emotional and extreme and she was just about to orgasm from the vibrator treatment I was giving her, and as I felt my fingertip already slightly gripped by her anus, I deliberately and very slowly pushed against that last resistance and penetrated her ass up to the first knuckle. Wifey went off like a rocket orgasming so hard and loud like I had never seen. I actually felt her contractions on my inserted finger. It was totally awesome and intimate. As if she was releasing the pent up tension from the weeks before building up to this. So now I regularly insert a decisive forefinger in wifeys ass and she continues to cum really hard when I do this. We still have not openly talked about what we are doing but she has said that she prefers my finger “down there” to be still after I insert. Some pics to follow.

New level of orgasm unlocked 2
 

Some pics

Met at lady from work, whose long term bf had just moved away. Dinner turned into coffee at her place, turned naked. She was easily miltiorgasmic
Round 3 turned into 69, put a finger on her butt and she came really, really hard. Nearly smothered me.
She asked me to fuck her butt, but it wouldn't fit. Went out several times, always finished 69 + finger in butt. Never succeeded in fucking her butt, but we tried several times. I was up to using thumb, so think we would have gotten there as she certainly like anal stimulation.
Unfortunately bf came back to town and our adventure ended.

Sticking a finger or two in my wife's waxed, gloriously adorable pink eye is one of the great pleasures in life... made better only if it's my cock and not a finger.

Ass journey so far
 

My wife was never interested in anything ass related and although I was curious I never pushed her to do anything.
One year ago she became friends with a female colleague, we always call her the "sex positive colleague". They always talk very openly about everything sex related and the female colleague told my wife how much she enjoyed a buttplug up her ass while getting fucked.

So my wife was suddenly interested in buttplay and told me that she wanted to try a buttplug. We had a cheap one at home, the classis small black buttplug with a fake diamond on top. The first tries felt a little awkward but when in the right mood she enjoyed the feeling. But she always complained it was too rigid and we used it less and less.

I wanted to try more with her asshole but she was not as enthusiastic. So when she was on top I grabbed her ass and slowly slid my fingers towards her buttcrack until one finger barely touched her anus. But I stopped there. She said it was a nice tingling feeling.
The next time I went a bit further and layed my finger over her anus, again not going further than that. Then I started to slowly massage her anus from the outside which she enjoyed.
Another time while fucking I placed my finger over her anus again and she told me to stick it in a bit. That night she had a really intense orgasm.

From that time on I regularly fingered her asshole while fucking. At first I went very slow and just slid the tip of my finger in. And I always made sure that she is very horny and my dick is already inside her.
The more we did it the more she enjoyed it. Our favorite position is doggy where I insert my thumb in her ass. Every time I can go deeper, a few days ago I inserted my thumb all the way.
My goal is to fuck her in the ass soon.

But my dream is to double penetrate her with another guy one day. :D