I was introduced to anal play with female partners quite late in life, I always thought it was a strict no; no for the earlier years in my sexual experience, tragically. Then in my forties I had a relationship with a lady who was very sexually adventurous, really quite uninhibited in many ways. One morning when in bed together while we were playing with one another, which appeared to be most of the time, my fingers began to slip down beyond her shaved vulva and I found her now moistened anus.
Being the perfect gentleman i asked her if it was Ok for me to stroke her there and she immediately replied that of course it was. As I stroked her anus it seemed to open up and my finger just slid inside, and what an amazing feeling that was. I then began slipping my finger in and out of her open anus and two of my other fingers were doing the same in her pussy. That opened the door for the rest of the relationship when I always ended up with fingers in both holes. Something that surprised me was the thinness of the membrane separating the vagina from the anus/rectum.
Probably the very best experience i had with this lady was the last time we were together before going our separate ways. On a cold February afternoon we were sat on her large futon and as time passed she placed a cushion on my lap and placed her head down and drew her legs up along the futon. I began sliding my hand up the back of her top and stroked her back, soon my hand strayed down inside her track bottoms to find that she wasn't wearing any panties.
I then began to caress and massage her bare bottom and very quickly slipped my fingers down the crease finding a receptive anus. Tugging her track bottoms down exposing her bare bottom I began to massage her anus and my finger entered with ease. A few minutes of this and my lady friend began breathing very heavily which indicated to me that things could progress to the next stage, so I suggested that she should lie down on the futon and as she did I pulled a her track bottoms down to her ankles, pushed her thighs apart and slid my finger back into her anus. I then began to lick and suck her tight little shaved pussy lips ( she had a neat little puff of hair above her vulva done at my request), soon she began to gyrate her hips and uttered the words "sweet jesus".
Following this she propped herself up and grabbed my belt undoing it and my jeans, she then pulled them down along with my pants and took hold of my very erect penis and began the best oral sex she had ever given me. An unbelievable afternoon and the last time we ever saw one another, but I will never forget this lady as she introduced me to the pleasure and joy of anally stimulating a female.