Anal Play, Prostate Massage and Milking 101
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 | | Coming into one’s sexuality as a gay man is a road fraught with choices and one of the first choices you’ll need to make as you’re embarking upon having a fulfilling sex life is what the parameters of sex will be for you. Some gay men opt to make oral sex and various forms of mutual masturbation the mainstays of their sexual pallet while many more go whole hog and seek to color their bedroom canvas more boldly by adding anal sex to the repertoire. It’s probably safe to say that 80% of gay men enjoy playing some role in anal sex scenarios. Generally speaking, different guys will gravitate to different roles within the anal sex scenario that match their particular sexual appetite: that of the top (the guy who does the fucking), the bottom (the guy who gets fucked), or a versatile (the guy who flips a coin and sees what he’s in the mood for today). For bottom boys and versatiles there is some training that must be underwent, that can be thought of as a right of passage. For a man can not just turn up his rear and expect it to be, instantly, a ready to go love tunnel (he’ll be in for a rude and somewhat painful awakening if he does), rather the ass must be trained to receive the intense stimulation of anal sex. Basically, a guy has got to learn how to get fucked in order for it to be mutually pleasurable and here anal play and prostate massage (prostate massage is really the whole point for the bottom, as it is the prostate that radiates that shockwaves of pleasure that make the twinges of pain worthwhile) is the primary training tools for the main event. |
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 | | “Blue Belt” moves are not overly difficult, but are not recommended for a virgin's first time on the matt either. Blue Belts are Developing Students. They possess basic sexual skill, good common sense, and strong body-awareness. |
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| | For gay guys who intend to take their sexual intimacy to a level beyond oral sex, mutual masturbation and front (genital to genital stimulation), I.E. those wishing to indulge in anal sex, which would be the majority of (but not all) gay men, learning your way around your anus and your man’s anus is essential. So, male anal play and prostate massage are major building blocks in the architecture of gay sex. So where these techniques are considered exotic for heterosexual guys and are ranked as red belt techniques, for gay guys these techniques are just a step beyond the basics and are thusly ranked as blue belt techniques. |
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 | Training to get fucked Vs. just having fun with anal play!
As we detail Anal Play and Prostate Massage from a gay perspective we will be focusing on the practice not as an end to itself (as with straight anal players) but as an anal training method with the end goal of being ready for gay sex. That said, anal play can certainly be an end to itself with no goal or thought of ever being fucked, and the practice should not be overlooked as an enjoyable and healthy (prostate massage has been shown to promote male health) pastime.
So with the goal of being fucked we will apply the same principals of standard prostate massage, prostate milking and anal play (seen below) but with the goal of using larger and larger insertion toys until we are comfortable with a toy that is the same size or a bit larger than our partner's penis. Why a bit larger? Orchestrating a tool to penetrate yourself gives you full control, where as being fucked by a guy (even a loving guy) takes some of the control factor away, he will not be able to feel if he is moving too vigorously, if his thrusting is too hard or the angle agitating. Communication is the key to good anal sex. But to be as prepared as possible training with a toy slightly larger than your man's dick will give you a little bit of an edge. |  |
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| | Some excellent prostate toys to work with... |
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