Judging from the popularity of this category and the myriad of responses I received from the two stories I have in this category, I have come to the conclusion that the misconceptions and preconceived notions respecting anal sex are legendary. My impression is for the most part that a lot of men want it and a lot of women are horrified at the very thought. Generally, society has frowned on this type of sex, as reflected in derogatory remarks such as "asshole". Unfortunately, a lot of people are missing out on a great addition to their sexual repertoire.
Before I go any further, I want to VERY clearly urge anyone with ANY concerns about their health to USE a condom. Even the gentlest anal sex can cause tiny nicks and scratches that could easily conduct any organisms straight into your body.
The anus has a multitude of nerves and muscles which when stimulated correctly, can provide enormous pleasure. Two sphincters are obvious when a finger is inserted – the first which provides the 'pucker" with which everyone is familiar, the other, about half an inch in. The first is controlled by the individual consciously – thus you can tighten or loosen it at will. The second is controlled by the part of the brain that controls bodily functions such as heartbeat, breathing etc – i.e. you cannot control its reactions directly. Proper and gentle manipulation can be equally enjoyable for men – whose prostrate can be stimulated from the insertion of a finger in the rectum – and for women, whose G spot is readily massaged through this form of lovemaking.
I would highly recommend that each individual familiarize themselves with their own bodies, exploring their own fundaments first to gauge the feeling and reactions that the insertion of a finger or object engenders.
As an aficionado myself, and female, I thought it would be helpful to address the issue and give my own suggestions/recommendations respecting the introduction and enjoyment of this unique form of lovemaking. I will deal with male penetration of a female's rectum as that is what I can recommend and am familiar with.
Anal sex is not something that should be introduced on a whim, nor thrust upon someone who is unfamiliar with this very arousing form of lovemaking. Ultimately, I believe that preparation and patience are the two primary ingredients of a successful introduction to anal sex.
A subtle yet honest form of behaviour modification works very well in this regard. Introducing your lover by attempting to push a stiff penis up a very small area unused to intrusions from that side of the body is a guarantee of failure. Rather, start gently and carefully.
1. First, begin with oral sex – an excellent starting point as you not only have intimate access to the desired area but as your lover's arousal increases, you are provided with the opportunity to gently and subtly introduce a finger; for instance, just tickling the fundament as your tongue takes care to keep her attention focused on the main event. As your lover starts to peak, push your finger very gently within the rim – do not go too deep or you will not only most likely derail her orgasm (thus creating a very frustrated and angry lover), you will also overstep the first steps to successful seduction.
Do this frequently and often, allowing her to slowly get accustomed to the feel of something tickling her anus, and in turn, linking an orgasm with the sensation of a foreign object around her anus. Done correctly, she will unconsciously begin to enjoy the extra stimulation provided by a careful finger or a warm tongue.
My strongest advice – DO NOT rush it! Most of us have been taught from a young age that anything to do with the very natural functions conversant with an anus are "dirty", that anything to do with the butt is "hands off". So not only do most people have to deal with the startling reality of accustoming themselves to something foreign in their anus – even more importantly, they have to overcome societal imperatives and parental restrictions.
