Well my first anal experience was in my very early 20s with my bf at the time. Nice guy and had a bit of a kinky side to him which brought out the best in me ;) So we'd talked about trying it and I was still pretty hesitant about it. Chatted to one of my girlfriends about it and she just raved about it, warned me what it would be like and gave me some good advice. So we arranged a suitable day/night when his flatmates would both be away. I went over to his place in the afternoon once I'd finished my assignments and took my overnight bag. Had a few drinks, a nice dinner, etc followed by a few more drinks to get a bit of Dutch courage (I think the expression is?). Started on the couch with a bit of kissing, bf taking some direction on where my good spots were (ears, neck, etc) and continued on until we were really getting into one another and both really horny! Started undressing one another, slowly at first and then a bit more rapid (being careful enough not to rip any clothes - too expensive!) Lot more kissing went on and me sucking him and him licking and rubbing my clit me until I was really wet and aching for him to be inside me. He rolled me onto my front and I got up on all fours and he did me doggy for a bit to get me really going, while playing with my clit. Then we we both thought the time was right he pulled out and reached for the anal lube he positioned stategically on the bedside table. I remebered what my girlfriend ahd told me "too much lube is nearly enough!" So bf got all lubed up and spread plenty in and around my asshole. I remember how damn cold it felt, yet also exhilerating at the same time. Bf started off with a finger working it slowly inside a little, then out, then in a little deeper then out. Felt different, but ok. After a bit and once he could get one finger in all the way, he went for two fingers, starting slowly and shallow and working them in bit by bit. All the while keeping my clit hard and atentive with his thumb. With two fingers working in and out of my wet ass, I felt him curl them to stroke my womb through the ass/pussy wall - quite a mind bending feeling I have to admit. He then lubed up a dildo (and my ass some more) and started working that in and out of me. Hurt a bit at first, then just felt a little uncomfortable, so we slowed it down and tried again. Relaxed a bit and it didn’t hurt quite so bad. So then we decided it was now or never. Plenty more lube and slowly bit by bit he managed to inch the head of his cock inside my ass opening. Managed to relax a little so he could go in a bit deeper. Was an interesting sensation – this hard hot object going up my ass instead of something coming out of it. Still a bit painful. After a while he managed to get all the way inside my ass and was able to thrust slow but deep. The feeling was intense! I felt so “full” for lack of a better word. Had to remember to breathe deeply and relax, otherwise I’d tense up and it would hurt a lot more. By the end of our first time it didn’t hurt as much as it had at the beginning. It was an amazing feeling to feel him tense up and unload inside my ass. The next day I knew I’d had something up my butt – a bit sore, but ok. After that, each time got better and better, easier and easier. Pain was soon replaced by pleasure and I’m pleased I stuck with it.