I honestly cannot say that I have ever had any fear of anal sex. That's largely why it was never a problem for me. I forget where I read up on it, but there have actually been studies done around the subject and interestingly enough, they all noted that the state of mind of the bottom is directly related to the level of pain (if any) that they will experience. For individuals who went into the experience with the fear that it was going to be painful, the results all indicated that they experienced a certain level of pain. By the same token, they also all noted that the individuals who went into the situation with a relaxed frame of mind, their body also relaxed accordingly, and as such, they did not appear to have a painful experience.
So… With that being said, I would suggest trying to relax yourself, as this has been scientifically proven to be an effective method. Also, as someone who is well experienced with the world of all things anal, I would strongly suggest two different things for your first experience. They are:
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Due to the added and uneven pressure that fecal matter along your insides can create during anal sex, I would strongly recommend that you fast for 24 hours prior to your sexual experience (fluids are ok though). This will help to make sure that your upper GI tract can empty itself out, as not to add any additional pressure that may cause pain or discomfort during the process. While this is by no means necessary, it can substantially help in reducing or eliminating any discomfort you may experience as your insides shift during the process of the sexual encounter.
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Make use of a shower-shot[nb]Such as the one illustrated on Fort Troff at http://www.forttroff.com/product/32001.html[/nb] or an improvised method (like removing the shower head from the hose) to clean out your bowels. This process will slowly help you to relax the different muscle groups before you begin, and it will also ensure that any fecal matter in your general lower region will not add any uneven pressure to your insides in the process, which for some, can be rather uncomfortable. The key goal is to fill your inside with water at a slow and controlled rate to help slowly apply slight pressure to the general area, then expel the water and anything else that comes out with it. From there, it is recommended that you repeat the process a few more times or until you are left with nothing but water. This will also prevent the rather "shitty" smell, or the "mud valley" that often comes with the world of anal sex.
Lastly, when bottoming for the first time, I would be inclined to recommend that you "sit on it" so to speak. This ensures that you as the bottom are in full control and can let your insides begin to relax before you continue to insert. Remember… As the top, you cannot feel where or if the bottom is in pain or discomfort, but as the bottom in control for the first time, you can use your own senses to your advantage to help you guide it in at a pace that's comfortable for you. Also, as strange as this may sound, an uncut dick (especially with bareback) will often feel more comfortable for the simple reason of the added maneuverability in and out that the foreskin provides. Just a heads up. :cool2:
As a general rule, I have observed that it takes a good bottom to make a good top. If you have an experienced top who can also bottom like a champ (such as myself), you may be surprised at how easily that they can manage to get themselves in part way, then work your hole to relax it until it sucks in their whole shaft. Above all else, be sure to relax yourself... It will go a long way in the end.