The biggest age gap I've experienced so far (and probably ever will) was back in the days when I went to college. I had just turned 28 and I was spending my evenings down in a local pub where I regularly met a lovely ginger haired mature lady. It turned out she was 57; but pretty young at heart and I really enjoyed being with her, talking about music, laughing, havin a few drinks together... One night, closing time was near, she eventually invited me to come with her and so I did. Walking along the way, I was totally thrilled by the thought that she might be in for more than just another drink, but pretty much because of our age difference I was far from confident about making the first step. For sure we had spent some evenings with great conversations, but there had never been any kind of physical contact between us.
When we arrived, she offered me a seat on her sofa and disappeared for while before she came back into the room with a nice longdrink she had mixed for us. She sat down beside me and it didn't take long until she started fondling my arms and thighs. Soon we were kissing each other and she took off her black top first, then her bra and before I had even time to realize I was fondling and kissing her mid-sized pale white and slightly freckled breasts. I ended up with my pants down and she gave me an enthusiastic blowjob until I blew my load in her mouth. She knocked it down with a slug of her drink and seemed absolutely comfortable with keeping her pants on that night. She went back into party mode and stayed topless while we were talking, drinking and I was allowed to touch her breasts and nipples whenever I wanted to. It was one of the most incredible nights in my life and I made up for it the next day.
We finally became very close fuck buddies for about one year. We kept seeing each other 2-3 times a week and were just going at it like crazy teenagers... she's a really great lady.