Well... My first time trying anal started with fingers... then moved to small toys... then large toys... All of which used ample amounts of lube and all of it is extremely enjoyable for me. My experience with other people using toys and strap-ons has been pleasurable, but I've worked up to it and it wasn't rushed - or else it can be uncomfortable. I have not had the opportunity to have the real thing. The difficulties of denial and long term relationships . With that said, it is far more enjoyable if you use a ear dropper to "water out" beforehand. Just in case you are contemplating.
I topped several times before I bottomed. And it was almost a spur-of-the-moment thing - I said "You know what? Let me try bottoming tonight." How did it go? Great. We'd been to bed together several times, so there was a lot of trust and shared history. He took his time opening me up and entering me. I decided I quite liked it, but I liked topping more. I've bottomed a few times since, but I usually stick with topping. Lex
It was quite emotional for me... It was something that I had fantasised about for so many years... I basically felt like I was losing my virginity all over again. I was top but was laying down and he came down on me... I was expecting everything to be a bit more difficult but it just worked (I find an anal sex with guys tends to be easier to get going than vaginal sex... Guys tend to be in the mood without as much help). It was a bit overwhelming to realise that it was finally happening. What I wasn't expecting was the mix of the different sources of excitement from that point. There's the excitement of "oh my god I'm inside a guy's ass", but then to see the pleasure that floods over him and the connection that is formed between you as you get a rhythm... Amazing. The best moment was when he bent down and kissed me... I think this was the moment when I knew for sure that I was gay (not bi, as I had thought before) and want to share my life with men, as I had really not felt this way even with my wife (there's lots of other psychology going on there as well of course). I guess what I got was a bit of romance even in my first time, which was not what I was expecting from that kind of activity.
My first time was with my current boyfriend. We'd been giving each other handjobs/blowjobs for months before we finally went all the way. My first time was both really good and at the same time, not very good at all. My boyfriend had done anal before with his ex girlfriend so he sort of knew how to do it whereas I had no clue. Prior to doing it my first time I'd never had anything at all "up there" and I now wish I had. Also he fingered me for like a minute before doing the actual penetration, which is nowhere near enough time (for me). To be honest, it hurt. A lot. It was more of a strong, burning sensation than a sharp pain though (we did use plenty of lube but I wasn't prepared enough). He did go slow though and some of the pain disappeared after a while although it continued to be uncomfortable. While I did feel some pain I felt pleasure as well and that made it bearable. The best part about my first time was the intimacy and the feeling of being so incredibly close to the person I love. That feeling topped the actual physical sensation in my opinion. While the pain went away after the first few times, I still sometimes experience some slight discomfort during the initial penetration but it's nothing too bad.
First and so far only times have been with a small toy. First time was painful, but that's because I was stupid and didn't lube up lol. Once the pain was gone it was surprisingly amazing though.
I know I'm a bottom & knew this for a long time, you fantasise about it, then you get nervous about knowing its coming, then the pain as he goes in & then the emotional fireworks going on inside you that make it pleasurable. Even thinking about it makes me all warm and fuzzy inside, and that's when I knew they're was no straight hopes for me
