My exhusband made an attempt once when I was I think 20 and it was the most awkward moment in my life and i swore never again but this past year (24) my boyfriend was very nice about it and slowly started trying to get me used to it. Although I'm still not a huge fan It's not as bad and I'm ok with it.
MY FIRST ATTEMPT I WAS 22 AT FIRST IT WAS VERY UNCOMFORTABLE IT WILL DEFINITELY TAKE TIME TO GET USE TO I HIGHLY RECOMMEND USING A BEGINNER KIT THE ONES EDEN FANTASY'S HAVE WENDY WILLIAMS ANAL TRAINER KIT OR JULI ASHTON ANAL BEGINNERS KIT THERE ARE ALSO EASING GELS AND CREAMS THAT'S ON THE MARKET AS WELL
I was experimenting at the age of 12 (sic) with anal play and it felt like going to the toilet. But this topic never really left me, there was a certain attraction to it and I kept on experimenting loosely.
I was raped by a group of guys in school, and we moved to another base dad being in the military, and maybe on a the while on a business trip I met this person after drinks and some drugs we went to his place I did not know they were a transgender, unit we got in the bed, so I tried it and it was ok, but have not tried it again for about 15 years. But have been using a plug for the past 2 years, unknown to my wife who doesn't like anal.
Not exactly sure how old when I started playing around anally, but I couldn't have been more than like 12 or 13. I heard some friends of mine talking about girls being able to "do it up their butt" too . So during masturbation, I would try playing around with getting a Sharpie in there. I think it took a few sessions before I was brave enough to put something all the way in, but once I did, I got this weak feeling in my knees and the rest is history. I've masturbated that way ever since.
I didn't have anal sex until I was 19 and in college. I had a particularly adventurous boyfriend that was totally into it.
I first tried anal play at 16 but didn't have anal sex until I was 17. Interestingly enough, the first time I had anal sex was amazing but the many times after that until I met my current primary partner where nothing special. But my current primary is amazing and we love anal play!
I was 22, just this last summer. Hurt a bit at first, but the orgasm was incredible. Now I just can't get enough!