New here, peeing all over, please help! long..

Hi all! Was really hoping for some advice. I have had cats all my life so have dealt with quite a few different things. I currently have 3 cats.

Scruffy - 13 years very large, orange polydactyl cat, very intellengent
Katferd - 8 years very tiny yet very loud siamese (only female)
Tweaker - 3 years, gray shorthair, very fat, skittish and non intellegent

All of them have been fixed long ago and they all like to go outside (in the city)

A couple of months ago, we noticed that Tweaker was peeing in a wicker laundry basket in the basement. He was scolded and the area was cleaned. Then, we noticed he found a spot with lots of old blankets under a table and just had it saturated. Now, just in the past week or so, it seems like anywhere we put clothes down, he will pee on it! He even peed on the clothes on my dresser yesterday!

I have had cats with urinary infections before but they would never strategically plan where to pee, they would just go anywhere. He has a clean litter box available, as well as spends most of his time outside.

Please keep in mind that as Tweaker has been getting older, he is becoming more afraid of EVERYTHING! He is very lovey to us but incredibly jumpy. He has also been gaining weight incredibly. We do have a vet which my husband will be calling this week but I was hoping someone out there may have had this problem before.

Please help! I love my kitty but we won't be able to keep him if we can't solve this.

I'll move this over to the health forum but please don't scold your cat because it's something that can't be helped, especially if theres something wrong with him

I only scolded him the one time I caught him doing it months ago. At that time there was no sign that there may be something wrong with him. I don't believe in hitting my animals. Maybe that is why they are the boss I just really wanna help my kitty, and my clothes of course.

One of my kitties recently was diagnosed with bladder stones, and before we knew what was going on she actually was strategically choosing her spots to pee around the apartment. They all involved soft things--pillows, the cat bed, the thickest piled carpet and, yes, piles of clothes (once I even caught her trying to climb off my dresser into the full clothes hamper beside it). The vet said she was doing it because the softness was soothing to her, since the stones were causing her pain. Not saying this is what is going on with your kitty, but just pointing out that sometimes what looks like a behavioral issue turns out to have a medical cause. I think a trip to the vet to rule out any problems with your kitty's bladder, kidneys or urinary tract is in order. Good luck and please keep us posted!