OK, apparently I can't resist putting my 2 cents worth on the
Broke Straight Boys forums. Like some of the others, I'm not a natural at this, so maybe my perspective might help someone else who wasn't born to bottom either.
I had a traumatic first experience. It was with my first real boyfriend about 3 weeks after we met. Everything was okay until I heard him say, "oh shit!". He then tells me that the condom broke. I have always been really safe and back then I was so extreme about safety that I couldn't even catch a cold from sex, much less anything else.
Needless to say, I was mortified that my first attempt something like that could happen. I was so freaked I made him get tested immediately. Fortunately it was all good, but it made the idea of anal sex seem more like having surgery than anything sexual.
After we broke up I dated pretty much only bottoms. There's an old joke about my city that says whenever you tell someone you're from here the response is, "oh so you're a bottom". I was happy with the topping, but after hearing about and seeing how much people were enjoying it, I started wondering if I was missing out on something.
I started researching and was fortunate to know someone who "demonstrated" on himself all the anatomical details and all the what, where's and hows. Hahaha it was almost like a
College Boy Physicals scene! I also practiced a lot with various things to figure out the right size, rhythm, amount of lube, etc.
After I felt confident about it I tried it with a real person. It wasn't bad at all. No bleeding or anything like that. I can't know what other people are feeling, but I wonder if the pain is more psychological than physical. It certainly wasn't painful like a cramp, pinched nerve or toothache. I'd say it was more a discomfort than pain. At first I thought that my bladder was being squeezed and had to urinate. What I was really feeling was the semi-orgasmic results of the prostate being stimulated. Like someone else said, it's learning to turn what seems like pain at first into feeling good.
The most important thing is you have to RELAX. If not, it's no good. And you need to focus on what you feel. It's like the pleasure is something you learn to recognize and the more you focus on that, instead of worrying about all the logistics, the more pleasurable it becomes. I think it takes a lot of practice for some people, but when you do get comfortable with it the orgasm and what leads up to it are really much more intense and well worth it.
Attitude can also play a role. Find someone you can trust. Don't feel like you have no control. Bottoms sometimes can actually be the dominant one. There's a lot of other issues that can interfere - some feel like they are emasculated by the act and that can prevent them from enjoying it. Fear of disease or being injured is a factor for others. Working through all this stuff makes it much easier.
I've done it a few times now and it gets easier each time. It's not something I do a lot though, mainly because I'm too lazy for all the preparation. I also have never done it with anyone really big. I guess I'm about the only person not into size so much. Big dicks are, nice to look at, but sore jaws and sore ass isn't for me. Maybe it's something you work up to? I dated a guy over 10 inches once and I just couldn't get into the sex. Of course he wanted it all the time. At 6 a.m. that's the last thing on my mind. Especially after drinking till 2 a.m. We never did anal and I slept through half the experiences we had. Word got around about his endowment and friends thought I was crazy not to be into it. Oh well, better someone who appreciates that have it.
To sum it all up:
Practice with toys before you actually try a person
Learn to relax your entire body
Focus on what you feel in the penis, NOT the anus/sphincter
Try not to think so much, just stay in the moment and recognize what feels good
Remember that it is the prostate that makes it pleasurable and that's only about a couple of inches in, so regardless of size it can feel good if the top is hitting that spot
Use enough lube
Remember that it gets better with experience and it's not always going to be unpleasant
Start with someone who knows what they're doing when you're not experienced.
I'll also add that learning to bottom actually makes you a better top. It's hard to know what works best if you don't know what the bottom is getting from it.
Never thought I'd ever be giving advice on this subject of all things! Maybe my trial and error might help someone else. Have fun, be safe. Okay, class dismissed.
