Well Monday, I hit a milestone. It was the first time I ever tried any sort of anal play. Let me start from the beginning. I established one of my boundaries (there aren't many) with my SO right in the beginning of our relationship. I told him there was no way in hell that I would ever try any sort of anal anything, because it just seemed so incredibly gross to me. The topic was dropped for about 3 months. One night on a long car ride home from NJ to VA, we got on the topic of what we'd like to do to each other, fantasies, etc. He told me he wanted to do anal with me, not so much because it felt better than normal, but because of the control aspect. I let him dominate me on a regular basis, and I let him have all the control. At that time I was still a bit squeamish about the whole idea. Mainly the pain, possibility of shitting, etc. Last Friday night, we went out and I had way way way too much to drink. We got home (I don't really remember), and I somehow managed to have sex before getting sick. He told me the next day that he tried putting his finger in my ass with no lube, but I didn't seem to mind. I was shocked and surprised at myself. I felt wrong for a minute even. Fast forward to Sunday, I had been thinking about what had happened Friday night all weekend, and I wasn't sure if I wanted to cank the entire idea, or go with it. I decided I would give it a shot and if it was horrible, at least I can say I tried. I told him that I wanted to try what he did Friday night, but sober. He told me I should buy lube, etc. Sunday night I had the most vivid dream about my SO having anal sex with me, Monday morning I went and bought the lube. Monday night we both come home from work and we're relaxing. While he was playing Xbox 360, I was busy listening to some NIN and writing an erotic short story about him dominating me and having anal sex with me (I might post the story in a separate thread). He read it, was immediately turned on and we started with some foreplay. I went down on him for a bit, and he had me on my back, with my hands above my head, held down, and lowered himself onto me. It was great... anyway, we started to have sex the normal way, and I told him I wanted him to try it. He told me he'd start with one finger, see how it goes and then go from there. I laid on my stomach and he put one finger in (well lubed) and I pulled back instantly. It was such a weird feeling, plus I had the feeling like I was doing something really wrong. He asked me if I was ok and if I wanted to keep going. I said I did, and he tried two fingers, it hurt a bit and pulled away. I guess I had the scared look on my face and he reassured me that he wouldn't hurt me and it was all on me to control this. I said ok, but I wasn't sure I could handle it. He started fucking me doggy-style with my hands behind my back and him pulling my hair. It felt amazing, but I pulled away from him and angled my ass directly at him. He got the hint. He put about 1/3 of it in at first and I tensed up a bit and it kind of hurt. He put a bit more lube on and laid me on my stomach and then put it all in. It felt strange, but the strangeness melted away very quickly. He laid on top of me, and very slowly started to thrust, asking me if I was ok. I said I was and he continued. He started to go a bit faster and harder and it felt amazing. We went like that for a good five minutes or so, and he asked me where I wanted him to cum. I told him my back, and right before he came if felt so good when he was inside me. After we were done, I just laid there for a second, and kind of had that wrong feeling again. I was slightly afraid to move because I didn't know what would happen. It was ok though, I got up and was fine. Overall, it was a great experience and I'm glad I tried it. And I'm glad I let my SO do it, because I am in love with him, and I trust him. I let him take my ass virginity LOL. Well I just thought I'd share my experience with FS. Since Monday night I haven't been able to stop thinking about it. I definitely want to do it again and incorporate it into our routine. It also wasn't nearly as bad as I thought it was going to be. I relaxed and everything went smooth.