With me, I have always loved anal even as younger teen, before I ever had sex. I used to talk about it all the time freely. My first girlfriend I tried hard to get her have anal with me. We tried once and I just barely got the head in and she said she couldn’t take it. I remember it feeling so good that I didn’t want to take it out.
So I don’t know, I have never been shy about what I want. When I was younger I used to talk about sex a lot to pretty much everyone. So everyone knew what was into. I guess things would be the way they are now.
She is eight years older than me. This doesn’t make any difference now, nor did it when we met, but if we had met more than ten years before, I think I would have been too young or immature for her. In this ten-year gap I had other relationships, with their joys and sufferings, which taught me a lot about life and people. So when we started getting involved, it was easy for me to see that she was “the one”.
In summary, if I had met her ten years earlier, our relationship wouldn’t have developed, but if it had, certainly we would have had kids, and that would have been a major change in our lives.
That hole had always been a forbidden territory, she wouldn’t even let me touch it. I tried once to rim her, she pushed me away, grossed. If I had been more verbal or insistent, she would have blocked completely the idea from her mind.
We “discovered” anal later in life. I tried many, many times but she swore I’d never penetrate her ass. I know if she understood the pleasure earlier in our relationship, we would have been anal only because of her anal orgasms.
Had we started sooner, she would have had many more anal orgasms but I wouldn’t have experienced this wonderful thing later in life.
I told her many times how much I liked anal, and wanted to help her discover the pleasure. I had anal with two women before I met my wife and loved it. My wife has regrets she didn’t try harder earlier in our relationship but I was thrilled it happed later in our lives. It’s not something most people transition to in their early 60’s. I’m proud of how far we’ve cum in the last 7 years. We’re professional “analists”.
My wife and I sometimes mesmerize “what if we would have met and fall in love before she met her ex ?
We would probably have felt a similar connection like we do now.
Big chance I would have asked her - at some point - to do anal, and she’s positive she would have said yes.
Then due to the fact she never felt connected to her pussy, chance is huge we would have skipped pussy sex without even saying it out loud. We think we would have naturally evolved into anal exclusive.
And her 2 youngest kids would never have been born. If I’d met her soon enough, my youngest wouldn’t have been born either.
So dispite we’ve met eachother at age 49 and 50, and truly found eachother on an emotionally level, that then lead to a fantastic sexual level, we do sometimes talk about “what if” situations. Not out of regret, more out of sorrow for wasted years with people we both didn’t connect with.
What if I never found the forum ? Well, even before I found it, I suggested a month of only anal sex and she didn’t think twice before saying she wanted to try that. So I’m sure we would have evolved to anal only anyway. Pussy sex got degraded, very soon, to fast foreplay. We both couldn’t wait to swith my cock to her asshole, so the real pleasure could begin.
I was young enough that I couldn’t have met my husband much sooner than I did. I think we would have fallen in love anyway.
I do wish I had let him know I enjoyed the anal fingering we did while we were engaged because then we probably would have kept up with it and I probably would have started exploring my sexuality sooner. Considering all the things, I think it might have even worked out to being a net positive still. All things considered though, I only lost five years before I started getting curious about my sexuality and then discovered anal, so I feel like I have over all done pretty well on the what if thing.
Like you, my wife has some regrets not having tried anal earlier in our marriage. Unlike you, it took us 37 years for it to happen!
Discovering world class sex later in life is pretty mind blowing. We also recognize and celebrate what we’ve found. We don’t just have anal sex. We make a conscious effort to make the next session the best. We’re close to the end of the U.S. football season, and we both agreed we had a playoff-quality anal session on Saturday. We’re now preparing for a Super Bowl quality session in two weeks.