I would Google this but I am scared of what might come up. Now when I first got Roscoe 2+ years ago, I realized he had a nasty trick he did. I have never seen a dog give himself oral satisfaction with a happy ending. Roscoe does just this. I got him neutered the next week thinking this would stop it. I was wrong. There are just no more "happy endings". Issue 2 is he bites his tail so hard he cries but refuses to let go. His tail is broke and has been since I got him. Any insight will help. He was the product of BYB. I wasn't aware of BYB till recently. I also think he is a good example for people who want to breed their dogs.
Thanks!!

Wow... that's umm... different!

I would treat it like any other behavioral problem. If you see him doing it then do whatever method you prefer to do as a 'punishment' I like a nice spray bottle of icy cold water, certainly stops them in their tracks and makes them think twice about doing it again.

If all else fails then they make these for dogs ;)
http://www.geekologie.com/2007/04/dog-sex-toy.jpg

As for issue number 2 my mother has a poodle who does something similar... 2 poodles actually.
One was bitten by a wasp years ago and still chews that same spot to this day. She has tried many things to get her to stop to no avail.

The other one actually has a bit of a neurological problem and rips hers own hair out and cries... don't think you have that problem though.

Bitter sprays can help with dogs you like to chew or bite things. Just make sure you read the labels and get one that is safe to use on the actual dog, not just one for furniture.

Has his tail been checked out by a vet (I would assume so) does the vet think there might be a problem there and it is painful?
An option might be amputation if it is causing him any pain.

I think I would start using bitter yuck and spray his happy place.

Dogs when they get bored do strange things. It sounds like you got him with this behavior. Re-enforce a behavior that you want from him while correcting the behavior that you don't.

Spray bottles work great! If just water doesn't due the trick, add a little bit of vinegar. The water should just have a slight oder to it.

Biting of the tail is another boredom tactic. If you can't watch him, put a cone on his head. If he can't reach his tail, he can't bite it. Same goes for him enjoying himself. A couple of months of firm corrective behavior from you should help him kick his dirty little habit.

You should also get him checked out by a vet. There may be a reason why he is breaking his own tail.

Good luck..

I took him to the vet about his tail when he was a puppy. They said it was fine. You can touch it and he is fine with it. So I don't think there is any pain. It has been 2 years of training to stop the tail bitting and the other. Nothing seems to work. I thought getting him fixed would help but I guess not. The vet told me to wait to get him fixed until he was older unless he had behavioral problems. I thought that was one so I took him. Maybe I should have waited longer.

Hmmm, have to disagree with your vet there unfortunately, the earlier the better with males, I usually say around 6-12 months depending on the breed.

It does depend on the individual dog too though, with some it helps greatly, with others, you might not notice a difference at all. Sounds like yours is the latter.

Have you tried the bitter sprays before?
If so it might be time to up the anti, a cone like Lucky suggested for a few weeks would hopefully be long enough to break the habit.
And once the cone comes off, LOTS of distractions for another week or so, lots of walks, lots of new toys, just anything to get his mind of his tail and his willy.