cat behavioral problems

Question
I have two cats one 6 yr. old male and one 4yr old female that are very opposite.  The female is a gray tabby and very dainty & petite but, still likes to rule the roost.  She is playful and very well behavied.  The male I know very little about.  My husband got him when he was in high school from a friend.  When he moved out of his mothers house his mother kept him (until she got a dog).  Koll (the 7yr. male cat) was terrified of the dog and would not come down from his high perch to even eat.  So we took him in.  He has had two major problems as long as my husband can remember.  1.  he is very timid 2. he urinates on carpet, furniture, & wherever.  He was taken to the vet who found nothing medically wrong with him.  My mother in law gave me the backround information she knew.  Which was that he was harassased by another cat.   However, he seems to get along great with my female. We clean the litter box everyday, and use what he has been use to (recommended).  We did try other brands to no avail.  Sometimes he will try to urinate right in front of us. I have researched as much as I can but can't find an answer.  I have tried to keep him in a kitty friendly room when we are away, but he crys relentlessly, and he doesn't like to be away from the female (she seems to calm him), so I put her with him in the room & he  still urninates wherever he pleases.  So I try to babysit him but he will try to do it in front of me! We try to keep him happy with attention and with his favorite toys.  I am here most of the day but like most people do have to go out.  I thought it probably will take time, but I have been working on this with him for just over a year now.  Because I know nothing of his breed I can only venture to guess.  I am thinking he may be part siamese.  He is more vocal than the other and it sounds very similar to a siamese.  He is long and linky with a long skinny tail like a siamese. His head is similar to a siamese shaped head.  And he is very attention needing like siamese are known for. But he is dark gray with green eyes.  Please help us, we are at our wits end and right now can't afford a behavioralist.  He has become very expensive ruining our mattress & box spring, furniture, and clothes.  I can't afford to replace these items.  And I worry because of his age and how long this has gone on my efforts are being wasted.  What else can we do?  Tricia

Answer
Hi Tricia.  Urinating outside the litterbox is usually caused by three things. A Urinary Tract Infection (which you stated that he has gotten a clean bill of health, so we can "X" this one out), Marking Territory (has he been neutered? If not, this could definately be the problem and doing so will decrease or eliminate the problem) and Stress.  If he is neutered, stress is most likely the cause.  Cats are tricky with this.  You are right, behavioralists are extremely expensive, and rarely do help with situations like these.  His age is a concern, as he is set in his ways, so this will be difficult, but not impossible.  What we need to do is "de-stress" him.  This is usually done with a very, very slight sedative from your veterinarian.  It's almost like an antidepressent for a human, and has been nicknamed Kitty Prozac.  What this medication does, is relax the cat a bit, which would cause him to feel comfortable enough to use the litter box, ect.  This medication can be used for a long period of time, and when getting off the medication, it is slowly weaned off by decreasing the dosage and mg.
Be sure to get the urine smell completely out of your carpets, furniture, ect., as if he can smell any hint of the scent, he will eliminate there.
This is about all I can suggest.  I wish you the best of luck and wish I could be of more help.  Please let me know how he does!
Hilary