Gentlemen, perhaps you have found your way here from links on the internet somewhere and you were intrigued. Or perhaps your lovely SO has mentioned that she'd like to explore your ass. Only one problem - you have never done ass play. Like, in your whole life. Never. Not so much as a finger. It's okay. Just keep reading...
Ass Play - Where to start?
The best way to learn about your sexuality is to explore your own body. Masturbation is an excellent example. Since you have played with your cock enough to get it down to a fine art, you are much more knowledgeable about what turns you on and what doesn't, which helps in communicating the finer points of your sexual preferences to your partner. So it stands to follow that the best way to begin finding pleasure in your ass is to explore it yourself, first.
Cleaning out to avoid a mess: Many men find that all they have to do is make sure their bowels are empty before playing, and there's no problem. This works best if you have a good diet with enough roughage and you are relatively young - I'm going to guess, and say under 40. Typically, feces do not sit in the rectal canal. Rather, they stay up in your colon and periodically get released into the rectal canal, and your body gives you the message that you have to go.
If you want to rinse out in the shower to be sure you are cleaned out, you can just buy a fleet enema and empty out the contents without using it, then fill it up with water from your shower. Put small amounts of water (like 1/4 of the bottle) into your ass and expel it, repeating until the water you expel is clear. You are not trying to give yourself a complete enema - just rinse out the rectal canal. Then wash just the exterior of your anus with soap and water. Easy peasy. You are good to go.
If you want more information about staying clean, read this.
Fingernails: Make sure your nails are trimmed and rough edges are smoothed, and/or use gloves (which can help with clean up as well). The lining of the rectal canal is delicate and can tear easily. You don't want that to happen, so you should never use anything with sharp edges for anal play, including your fingers!
Lube: Lube is an absolutely essential component to enjoying the exploration of your ass! (And please don't let any stupid porn video make you think otherwise - spit is not lube.) You can use coconut oil, just be sure to put down a towel because it can stain. Also, take a small amount out and put it in a small bowl or on a plate because you don't want to stick your fingers back in the jar when they have been in your ass and you suddenly realize that you need more lube.
Or, you can get what I consider to be the best anal lube out there - Sliquid Silk Hybrid lubricant. Completely body-safe, no bad ingredients, lasts a decently long time, doesn't dry out and get sticky. Amazing stuff. Excellent company.
So now you are cleaned out, fingernails trimmed, and you have your lube. What next?
Position: The position that you find the most comfortable to explore your ass in is very individual. Explore a few and see what works best for you. You need to find a position that is comfortable for you so that you can really relax. Laying on your side with one leg drawn up, on your back with your legs up, on your hands and knees, or sitting back on your knees - those are all positions men talk about. Consider using pillows to support your body. I have even heard a man say his favorite position was...sitting on the toilet! That sounds decidedly not sexy to me, but it works for him. Above all, comfort is important. You need to be able to relax.
Turn On: Get yourself turned on in whatever way works best for you. Porn videos on your phone, fantasizing your favorite scene, reading erotica, jerking off, playing with your nipples or your balls, whatever works. The reason why this is important, is because once you start playing with your ass, it will feel better and you will have an easier time finding your prostate if you are already turned on. It swells with prostatic fluid and becomes more sensitive.
Outside First: Your mantra here is going to be go slow. So you want to start massaging your perineum, the area between your anus and your scrotum. Many men love having this region touched, as it is an indirect stimulation of the prostate. Next just massage your anus, around the rim and back and forth and whatever feels good. If you push on the anus without entering, it will encourage everything to relax.
Inside Next: When you are ready, make sure your finger is well-lubed, take a deep breath and as you breathe out, push out as if you are trying to have a bowel movement (don't worry, if you have cleaned out, you won't). This allows the sphincter to open and your finger should slide in fairly easily. If it starts to feel uncomfortable or you feel pain, back off and give your ass more time to open up. Don't rush your ass! Again, go slow. Sit there for a while and just get used to the new sensation. Initially, the only thing you might feel is like you have to go to the bathroom. That will pass. But many of you will already be thrilled with new and very pleasurable sensations.
Locate Your Prostate: Your prostate is located about 2 inches inside, towards your belly button. Exact same location as a woman's G-spot, if that helps. The prostate is about the size of a walnut, and is easier to find the more turned on you are. Some men will know as soon as they find it. Other men won't be able to feel anything at all. Once you've found it, experiment with what feels good. Gentle pressure? Stroking? Rubbing in circles? Quick in and out? On and off pressure? Just remember not to aggressively poke the prostate. It is a gland and you don't want to bruise it.
From here, just explore, and discover what feels good to you!
Some Cool Things to try:
Jerk Off: Most men report that an orgasm from combined prostate stimulation and penile stimulation feels about 10 times more powerful than a normal orgasm. Jerk off while playing with your ass and see what happens! As a side note - do not be concerned if you are unable to attain an erection while you are playing with your ass. This is completely normal. Some men have erections that come and go, some men stay hard the whole time and some men can't get hard at all. All of those are completely normal.
Prostate Massage Only: Alternately, use your fingers or a toy and only massage your prostate. Some men say that they really don't enjoy concurrent penile stimulation with prostate play, that it somehow distracts them from the amazing sensations they get from the prostate, because it's a different type of sensation. You might be one of those guys! And some men can even orgasm from prostate stimulation alone, as well as enjoy multiple orgasms (so if you are still reading and were wondering why you should try this...there you go).
Butt Plugs: Will stimulate your prostate and can be worn during many activities. Intercourse, oral sex in either direction, foreplay. Watching a movie with your SO or out to dinner with her. Making a quick trip to the store and wanting to have a more fun experience! No one will ever guess the reason for that big smile on your face. You are limited only by your imagination. And by the toy. For longer term wear, I suggest the Njoy Pure Plugs or the Tantus Ryder Anal Plug. Both of these choices are designed so that the base sits between your ass cheeks more comfortably, and the differential between the widest point and the neck is large enough so that the plugs stay in more easily.
Prostate Toys: Some men find using their own fingers awkward. If you are not flexible enough, your arms are short, torso is long, fingers are short, prostate is further in - there can be a lot of reasons - your ass can be difficult to reach, which makes finding your prostate nigh impossible.
In that case, or if you just want to take your ass play to another level entirely, I recommend four different toys. The first two do not offer vibrations and the second two do. Vibrations are a matter of preference - some men don't like them at all and say it makes everything sort of go numb. Other men say they can't really get much pleasure from their prostrate until they use a vibrating toy. Experiment! Remember that anal toys must have a flared base to be safe, and make sure they are not toxic!
Aneros Helix Syn: When inserted, this device is designed to provide hands-free prostate stimulation by clenching your anal sphincter. It's a great toy to wake up that area of your body to the pleasures that are possible. And some men find they can orgasm hands-free while using it! This is a great toy for beginners. And should the opportunity present itself, it can be worn during intercourse with explosive results!
Njoy Purewand: The curve, length and shape of this toy is absolutely perfect for prostate stimulation, solo or with a partner. Makes your prostate easier to reach, and longer ass play sessions are almost effortless because of the weight of this solid stainless steel toy. Designed by an engineer with a love of ass play, this toy gets rave reviews across the board (and is amazing for G-spot stimulation, too). The Purewand has a smaller end and a larger one, in case your ass starts craving something a little more at some point. The smooth metal will hold heat, and feels delicious warmed up by running hot water over it (not too hot!).
Lelo Billy Prostate Massager: If you like vibrations on your prostate, this is the Cadillac of prostate massagers. The curved design is perfect for reaching the prostate, and the variety of vibration patterns and intensity levels allow you to adjust this toy to your own preferences. Pretty quiet, too! Rechargeable - never worry about batteries again. The size is just big enough to be effective but not large enough to challenge.
Aneros Vice: Another excellent toy that offers vibrations for anal play is the Vice. It's a beautifully designed piece of equipment, the shape is made to rest right against your prostate. The removable vibrator is machined steel and packs a punch. Three vibration patterns with 3 levels of intensity. Uses one AAA battery. Just as quiet as the Lelo Billy. A of mine says this toy is so intense that he only uses it once a month and the neighbors hear him yell when he comes.
If you purchase any of these items be sure to use the coupon code Ruby for 20% off listed prices!!
Have fun playing with your ass! Just remember....
Cardinal Rules of Ass Play
No Numbing Agents!
Not Too Fast
Not Too Big
Plenty of Lube
Anal Safe Toys