The first time I did anal was with my first fiance. He was pretty vanilla about sex. I was his 3rd sexual partner, and he was my first.
I had started stripping at the strip club where he had become a bouncer. One of the other dancers (a girl named Rio who was amazingly sexy and who I had a huge crush on) was talking in the dressing rooms about how she had an amazing orgasm earlier in the day with her boyfriend from anal sex. I had heard about anal sex, but had never tried it and had never had more than the tip of a finger or tongue in or near my butthole. I asked her a few questions, including how to prepare for something like anal sex.
That night, on the way home, I stopped to pick up an enema. At home I did the enema and was pleased to see that everything would have been clean anyway (it took me a little while to be able to tell that without actually having to check). I put on a form-fitting tank top and panties and went into the bedroom to kiss and 'make out' with my fiance. Once it got to me giving him a blowjob, I told him that I wanted him to try anal sex with me, and I told him that I had been really turned on in the dressing room by hearing Rio describe how amazing it was for her. My fiance was a little hesitant, but when I told him that I was sure I really wanted to try, he warmed up to the idea. We continued with oral on each other for a little bit and then vaginal sex. I lubed up my fingers and then his fingers and it was the first time I had anything penetrate more than an inch into my ass. His dick was so hard the whole time in anticipation. We put tons of lube on his dick, which turned out to be a really great idea. Because he was the only guy I had been with at the time, I didn't fully realize how big he was, but he was awfully big. He was also capable of lasting for a REALLY long time without coming. When it's a girl's first anal experience, that's not really the best combination.
I got on my knees in doggie position, and it took several minutes for him to get his dick to fit all the way inside my ass, and even then for the next few minutes, we had to go really slow because I was so tight and he was so big. If he would have gone too fast right then it would have been incredibly painful for me, but he was going very slow. I don't think he had a lot of choice, I was just too tight for him to be able to move in and out any faster. After a few minutes, I started to relax and open up a little bit. As soon as I felt his dick slide a little easier, it was an incredible sensation for me. It must have been incredible for him too, because his dick got even harder. I instinctively arched my hips up and lowered my shoulders to improve the angle of his dick pushing down inside me, and I reached my hand down to my clit and gently rubbed my clit. I was amazed that I could feel my pussy getting wetter from how good it felt to have my ass being fucked.
Even though he still lasted a long time (a little over an hour after he started fucking my ass), it was definitely the most frequently he got close to cumming at that point in our relationship. It wasn't until later that I learned how to stroke his dick with my pussy or ass muscles which never failed to make him cum within a few minutes. So an hour of anal sex with a large cock for my first time at anal was kind of a sexual workout for me. I took breaks by pulling my asshole off his dick and deepthroating him until he had to be back inside my ass again. When he finally did cum deep and hard in my ass, I was thoroughly sweaty, exhausted and glowing. The next morning when I woke up, my ass was so tender, but it wasn't painful. It was a deep sexual tender feeling. After that night, my ass needed a break for a few days. We were both young and horny, so we tended to have vaginal sex at least once or twice a day, and after that week, anal sex was something we both wanted at least a couple times week.
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