Suggestions written by a beginner, for beginners.
My previous anal experiences had been uncomfortable and unrewarding. I hate mess so my solo efforts had all been made in the shower and without lubrication. I often couldn't manage to fit more than half of my little finger inside. With a partner I have enjoyed gentle stroking and oral stimulation of the anal ring, but any penetration felt forced and unnatural.
I have always been intrigued by the idea of male anal play because the male g-spot is inside the anus. Having read a few stories on here I decided to again try stimulating my anus whilst masturbating, this time using Vaseline as a lubricant.
First of all I should stress how important hygiene is. Anyone considering anal play must wash their hands thoroughly beforehand. Anything that comes into contact with the inside of your anus can be absorbed directly into the bloodstream. Not a nice thought huh? You should also cut your nails for two reasons: it is very easy to break the skin inside your anus, and to avoid transferring dirt trapped beneath the top of your nail into your anus.
The following is a suggestion for those who have had little or no previous experience. Bear in mind I have only tried it once.
You should begin by lubricating the first two fingers of your non-masturbating hand. Find a comfortable seat, then lift and spread your legs apart, much like female porn stars will do to expose their anal hole. Gently massage the ring, slipping inside as you feel comfortable. Relax yourself as much as possible. Masturbate your penis in whichever manner you like, and as often as you like. When you feel at ease slip one finger inside. Your body may reject the finger. If so you need to continue playing with your ring until you feel more comfortable.
When your finger has penetrated you should find it quite easy to slip it in further. I found I was soon able to fit my whole middle finger inside. Use two fingers if you prefer. Push gently towards your penis, rubbing against the side of the anus until you experience a different sensation. It might not be pleasant. I found it quite odd, more inside my stomach than anywhere else. Continue to rub whilst masturbating. If it takes too much effort to reach this spot I suggest leaning forwards and sitting on your hand so your bodyweight does the work for you.
Hopefully you have found your g-spot. With practice you should quickly learn what feels good and what doesn't. My orgasm was more prolonged than usual and easier to hold back. It felt really good, but strangely I didn't ejaculate until the best of it was over, and only a little came out. I was disappointed because I enjoy ejaculating during orgasm.
I hope someone can benefit from this.