Pain from Anal Penetration

Q. I'm a gay guy who has just recently turned 18 and my boyfriend and I have decided we're both ready to have sex for the first time. I'm kind of worried that it's going to hurt or that I'll do something wrong that may hurt him. I've spent a lot of time reading articles about how to go about it properly for the first time, keeping clean, making sure to use plenty of water based lube while keeping safe as well. But he and I have experimented before and I just can't seem to get it right … anything I insert too far into my hind quarters, I get a sharp pain about 5 inches or so in every time to the point where I just can't continue. :(

My question is; is it going to hurt the first time regardless of what we do? Are the steps we've been taking just to minimize the pain? I've read that it doesn't have to hurt at all the first time, but I don't think I can relax anymore than I already have...

A. Well done for making the effort to be as knowledgeable as possible about your developing sex-life! Everyone should follow your example...

Many in the medical profession contend that penetrative anal sex (whether hetero – or homosexual) will always result in some damage … and that the best you can hope for in the long run are haemorrhoids. They point out that the anus is a one way valve. It is designed to allow stuff to pass out; it is not designed to admit anything. A penis (or anything of that size) stretches the skin and the muscles beyond what they are designed for. Compared to the vaginal walls which are about forty cells deep (which is what gives the vagina such elasticity), the walls of the rectum are one cell thick and when they are stretched much it can be painful to the receiver.

On the other hand, some argue that you can ‘train’ the anus to accept increasing larger objects - and without pain; however, this should be done with patience over a period of weeks and with plenty of lubrication. The rectum is not straight - see the male anatomy diagram. After the short anal canal that connects the anal opening to the rectum, the rectum tilts toward the front of the body, sometimes as much as 90 degrees. Then, after a few more inches, it swoops towards the front of the body again. A person can learn about the shape of his or her rectum by gently inserting a soft object, trying different angles and body positions, and concentrating on how it feels. Make sure the object has a flared base so that if you lose your grip, it won't slip into the rectum and become temporarily irretrievable.

Please read our article on Anal Intercourse (& related articles) for more information and tips. You may also find our Homosexual/Bisexual/ Other Non-Heterosexual Forum (& other Forums) to be of help.