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

[goodguy30]

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.

[andyt29]

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.

[daskers]

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.

[whatnow3]

Originally Posted by daskers

Mine will let me rub her ass hole, but won't let me finger 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.

[qazzy1749]

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.

[Mwhltfh]

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.

[Mwhltfh]

Some pics

[karlhein]

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.

[nonnymaus2]

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.

[outdoorl0vers]

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.