I’ve been suggesting and teasing anal every once in a while for 10+ years as it’s my biggest kink. She’s always been willing to give it a try but got uncomfortable even with me gently pushing a finger in her beautiful tiny asshole.
Well, a while ago something clicked. She was really turned on while doing doggystyle so I asked again to gently finger her ass at the same time. This time she immediately started screaming like an animal (not from pain!) and wanted me to keep going. Her hole really surrendered as I pushed my thumb all the way in without any resistance. To this day she finds it the biggest orgasms she has ever had. After that my thumb has been in her ass every time we have sex.
Yesterday she was really turned on, so I just took my thumb out and said I’ll properly fuck your ass now. I really struggled to get the tip in but as I finally made it she instantly started moaning like an animal once again. The feeling was unreal. I started to push in and asked if it’s hurting, but she wanted me to go deeper. Turns out there was no problem going balls deep in her ass which surprised me as I was sure my 20cm would take some time getting used to.