Just about every time we have sex. She loves it from behind and routinely asks me to put a thumb up her ass as she is getting close to coming to send her over the top. She’s not a huge fan of anal sex, but she loves a thumb up the ass for extra stimulation.

When we were younger it was part of our lovemaking. Especially me giving oral. Sometimes I would slide my whole index finger inside and push it in and out. This always caused her to have intense leg shaking orgasms. Now she has decided she doesn’t prefer it. But I still try from time to time and every few months, especially if we’ve had some drinks, she won’t protest and I’ll be fingering her ass while licking her pussy.

I recently read that a sex survey found that among women:

1) finger tip on her asshole
2) finger tip just inside her asshole
3) finger fully inserted

Women reported that 2) was the most pleasurable.

My wife is a 1) and 2) gal, when she's in the mood. Occasionally she cums instantly when 2) is applied.

Loads
 

My wife was initially averse to anything anal. However, as time went on she got into it. To the extent that almost every time I went down on her, I put a finger or thumb in her arse. Moving it back and forth slightly, whilst working on her clit made her cum really hard.

Mrs. Speedster-
 

Early in our relationship, she was interested in everything sexual. I often had something in her ass that included everything from: my penis, my fingers, my tounge - and different size toys and vibrators.

Unfortunately, I never bought a jeweled butt plug for her to wear.

Later, most of the anal play had to do with me handcuffing her and she had no choice, or there was wine involved. That mostly involved me handcuffing her in the doggie position and fucking her. Not a lot of fingers involved outside of cramming lube in her tight little butt.

After several decades, she is more interested in me just licking her ass. That seems to turn her on the most. Especially when she is on the phone. lol

My butt has endured a tragic lack of fingering, lately :(