When I met my wife we had what I consider to be wild, animal sex... all the time, every position imaginable, hours on end... and occasionally when going at it doggie style I would slip a finger in her ass.... nothing was ever mentioned about it, but I "felt" like it turned her on.... over the course of months I would occasionally make a remark about trying anal and she would say "hell no", you're not putting that in my ass...
Well, one day, out of the blue, she said she wanted to try it.... I lubed up quite well and lubed her ass a lot... then from the doggy position I tried... slowly..... many, many minutes passed... very, very slow progression... and I got maybe half way in... she was in noticeable pain..... I asked her if she wanted me to stop and not wanting to disappoint me she let me finish...
I didn't really enjoy it.. It didn't feel that great.. and I felt even worse because she hated it and said "NEVER" again....
Well, after that, I never even brought it up again.... and I stopped even with assplay during sex.... no fingers.. nothing...
That was 2 years ago... Then, over the past couple of months she's manually placed my fingers at her asshole during sex and seemed to like it when I would insert a finger while having sex side-side... Then, last week she nervously admitted to wanting to try anal again...
This time, I started super-slow... we had already been making love vaginally for quite some time and had used a lot of lube so the whole area was already quite slippery... I added more.... to her... to me.. then to her again... I slowly inserted a finger, gradually until it seemed not to bother her... worked it around... then slowly started rubbing the head of my cock around her asshole... let me stress, there was tons of lube.... over the next THIRTY minutes, I tried to get the head of my cock in her asshole... and again, let me say... she wanted this and asked for this, so she was really trying to help make this work.... I eventually got the head and MAYBE one inch of my cock in her ass.... I slowly started pumping.... still, only getting maybe a total of three inches in at the max... I could tell it was really hurting... I pulled out and added even more lube and tried again.... no better... still no more than 2-3 inches.... after 45 min (15min of actually having basically the head of my cock in her ass) she said she couldn't take it anymore... that it was burning like hell....
So I think my anal experience is over now.... 2 times in my life now... at least I can say I tried it... she hates it...