What if you met your anal only partner sooner ?
What if you started anal only sooner ?
What if you expressed your love for anal sex sooner ?
I want to know, tell me your stories in the sence of how things could have been if things happened sooner. Use your imagination at will.
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.
I think our timing was perfect.
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.
I wouldn’t even know what to say if a girl suddenly confessed me she wants something with me. Probably I would just stand still there saying something like “Ok” and move on (and maybe an accelerated heartbeat… or like recently: totally numb).
I have confessed it to two of my best friends (both female for some reason) and they took it ok, like just a curiosity and accepted it. The subject hasn’t been touched ever since.
I very much doubt that me and my boyfriend meeting sooner would have made any difference in us beginning our anal-only journey. We were both in our 20’s, and despite me being anally-obsessed, I don’t believe that either of us possessed interest in, or the level of maturity required to attempt an anal-only lifestyle. Maturity isn’t always based being a certain age, but after us being together for a few years, and discovering that this lifestyle even existed, we felt comfortable pursuing it… at least to the extent that we do. I’ve mentioned before that we still enjoy occasional vaginal sex, and when there’s the possibility of multiple partners, I enjoy some vaginal play or intercourse along with anal intercourse.
I didn’t know anal only was a “lifestyle” per se until I stumbled upon this group a year or so after we discovered anal. It wasn’t a decision as much as a strong preference because of her anal orgasms.
We enjoy foreplay involving all body parts but when it’s time for penetration, it’s always anal because of her orgasms.
Anal sex is something that has fascinated me from the very beginning, but it took a journey of about nine years before it became the only kind of sex I wanted. I went through most of that journey with my boyfriend; we’ve been together for more than six years now.
I think it was good to have gone through that development and taken that time. Today, I’m absolutely certain that I never want to have vaginal sex again, and I’m incredibly happy just being anal only. It’s a much stronger conviction than if I’d stumbled into it right at the start of my anal enthusiasm.
My current partner is the fourth guy I’ve been with and the first I’ve actually had successful anal with. He’s legit amazing and I really feel like I’ve finally found my person. 
The first time I tried anal was with the first guy I dated and it was a total disaster. I sometimes have these thoughts like would it have been different if I had approached it more maturely? Preparing myself leading up, having lube, being more vocal about how he should enter me and to go slow. Maybe we would’ve even tried to make it work when we went to different colleges? But I literally did NONE of that and it hurt a little and I started crying from embarrassment. So yeah we never tried again after that.
I honestly doubt I would’ve tried anal with the next two guys. One had a piercing that was always infected (ew) so we barely had sex, the other was huge and even vaginal hurt a little. But I do think if the first time had gone better, I would have started stretching earlier, and maybe would have had the courage to bring it up with my current partner sooner?
Or maybe if it had gone well the first time I never would have stubbornly started to train myself and missed out on the joys of anal entirely! 
My wife expresses regret she didn’t try harder to enjoy anal earlier in our relationship.
From my perspective, we discovered something so incredibly pleasurable later in life. It’s been a wonderful surprise.
I’ve learned to avoid “looking in the rearview mirror” and instead, focusing on the pleasure yet to be experienced.
At your age, you have many decades of super erotic anal sex to look forward to. Enjoy, because from my perspective, life goes by at the speed of light.