I hear from a lot of people the first time they tried anal it hurt, personally I found it pleasant even with little lube.
Thankfully, the first guy who introduced me to this activity was a very patient and gentle teacher, otherwise I might never have tried it again. I do NOT like pain....period.
Thankfully more so, ALL my other lovers, and now, of course, my hubby of 32 years, have been superb lovers and very CONSIDERATE lovers at that, making sure EVERYTHING we do together was and is COMFORTABLE. Thus, I guess I was lucky and spared any of the "it hurt so bad" stories about anal sex I have heard from others.
Even though I am "pretty tight" back there...with lots of lube and lot's of patience it is ALL GOOD.
I will add one note, however. While my first, and tenth and thousandth time were FINE, it was not till I was very experienced at this kind of play, and tried different positions,that we DID find some that were not comfortable, for me, anyway. Doggy, for instance. A "go to" for many, it just plain hurts for me. All the lube and prep in the world do not change that...tried it a few times and same each time. SO...we just don't do it that way!!! No big deal. All GOOD.
No. (EDIT: This was for PIV, I read the thing wrong.) It was lovely. I was with the man I married (although we later went through years of an open relationship, so he is not my "only" which I think is a good thing. For one, I appreciate him more, knowing how good he is compared to others.)
He was older, I was (obviously) 16 year old virgin. I waited until I was sure I loved him (that took a while, I don't fall in love easily) and obtained birth control.
We made love on his little twin size bed. I was SO nervous, but once we got started, it was just lovely! I didn't come, but it was my first time. Also, I wouldn't let him give me oral sex, so there's that. (I have NO idea why. I didn't think a man would "want to do that." My goodness, was I naive! ) We had done a lot of messing around and a lot of frigging, so if I had any hymen (which I doubt, because nothing ever hurt) it was stretched earlier. It was beautiful.
A few times later, he begged me to let him give me oral sex. A few times with that, and I could come. O.....M.....G........ I had "practiced" so I would figure out the way to have an orgasm. But, I had no idea how amazing it could be with an other person.
And, more than twenty years later we're still doing it. It rocks every time.
EDIT: Oh, the question was about anal. Here, I wrote a TEXTWALL about my first PIV experience.
No, anal didn't hurt the first time either. He has a way of "training" me, so that I'll be ready and anxious to try something new. I was a little sore, and had a little blood after the first anal experience (but, oddly not the first PIV) but, we probably didn't use enough lube, or something.
It never hurts now, ever. There are relaxing techniques you have to use, and I need to have an orgasm first. Lube is totally necessary. But, it didn't hurt. I could feel it, of course, but that's part of the fun.
I'm still waiting to try it with a more nicely sized penis. (Ohhh... was that a mean thing to say? ) Heh. Anyway... My first time having anal sex hurt slightly, but in a tolerable and I-kinda-like-it way.
The first time was unbearable. He had to stop and I was completely done with sex of any kind for the night, for a few days even. He didn't let me know what he was going to do, and went in entirely too fast/deep.
It's MUCH better now, and I love it...but that first time, ohhh my, ouch. He's lucky I ever wanted to try again.
No, it didn't hurt. It felt a bit odd at times, but it was overall one of the most pleasurable sexual experiences I've ever had. In fact, since then anal has become one of my favorite activities. I'm almost never "not up for it."
My first anal experience hurt like hell, no lube, saliva and force....a wicked combination. It was awhile before I went there again, but I practiced by myself with my fingers, butt plugs and dils.
Now I love anal sex, both to get it and to give it with a strap-on.
the 1st time hurt a bit but the guy that was doing it just sucked in general.(zachary simmons)=s horible lay. my bf now (jesse williams) is great at it and it feels great and we dont even need lube sometimes it feels so good.
It hurt some but in the good way I guess I figured it might. I'd used my vibrator there before and liked being penetrated there, otherwise I wouldnt have been looking to get my butt fucked in the 1st place! My 1st time was spur of the moment with an older guy I didn't know very well, in his car at a wedding reception, and I was the one who asked for anal sex. Not perfect and didnt last as long as it could have but looking back it was still pretty hot.