Spraying behavior - stress related

My cat Pim (now 6 years old, neutered) , sprays in the house since a couple of months.

He's pretty anxious by nature (not socialized well when he was a kitten), and is therefore more sensitive to changes; I try to keep things the same as much as possible.

However, he has been through some changes over the last 2 years. I moved two years ago and Pim has moved with me. A few months later I adopted a second cat, called Daisy (2 years old). There were no problems and they get along pretty well. 
Last year, in August 2014, I have had a litter foster kittens in the house with their mommy. This were my first foster cats (I foster cats for a local shelter and this is the only litter I took care of so far).
They stayed here with me for about 10 weeks. They stayed in a separate room which I specially designed for cats.
My own two cats could smell the other cats of course, but they couldn't see each other.
In October 2014, when all the kittens were adopted, I decided to keep the mother cat. She is about 3 years old and is a very sweet cat.
Daisy and Lily get along well. Only Lily and Pim ... Their relationship is a bit complicated. Sometimes they lay next to each other on my bed,  and the next moment Pim acts very frustrated to Lily. Lily wants to play sometimes and then chases after Pim. Pim doesn't like this and he runs away, upstairs. But Lily likes that and keeps chasing him until Pim found a place where he can't be disturbed (usually the attic, on a shelf or something, and he growls. I have never seen them fighting. As Pim growls, it is eventually clear to Lily and Lily just walks away.
 

Lily did this first with Daisy too, but Daisy showed Lily that she doesn't always like this behavior, so she quickly stopped chasing after Daisy. She never stopped chasing Pim , possibly because he is somewhat insecure (?) and his limits aren't clear for Lily.

Anyway, a few months ago I started to notice that one of my 3 cats occasionally sprayed in my house.
I saw Pim doing this a few times and also knew pretty fast that Pim is the one who is spraying.
First, I let his urine checked and he had cystitis. This could explain the problem. He had antibiotics. 
Last week I went to the vet and did an urine check again, accompanied by a bladder ultrasound, so they could see if the bladder looked normal and the urine could take sterile. His bladder looked fine. Result urine: No bladder stones, no cystitis etc. Everything looked fine.
A medical cause is therefore excluded; it is behavioral.

I got this feeling that this spraying behavior has a lot to do with Lily's presence. Because he does this approximately since Lily lives here, and because he often sprays against places where Lily often walks or sleeps. For example, I just bought a new cat tent and about an hour ago I saw him right there, spraying against the new cat tent. The only one who has lain in that tent is Lily, so far.

The vet also talked about a cat behavior expert. I keep this in mind, but I'll try things myself first, and try to reduce his stress as much as possible.
Placing Lily somewhere else is not an option.
There is never a fight or something, but obviously it is a big source of stress for Pim.
I also use Feliway plug-in since 5 weeks. I think this works a bit, though he still sprays. Not much though but this behavior did not stop..
Does anyone know what might be helpful?

It's not that my house is too small for three cats. I have a living room - kitchen and hallway downstairs. On the first floor I have three bedrooms and two of them are pretty big. I also have an attic with lots of space, I sleep here myself.
The cats are able to go outside whenever they want to and Pim also loves to be outside (not because of Lily, he always loved being outside)

The Feliway Plug-in is placed on the first floor, since I think the cats spend most of the time on the first floor and the attic. He usually sprays in the living room.. perhaps it is an idea to use the feliway plug-in in the living room?
 

Does anyone have tips, advice and maybe experiences?

(English isn't my native language so I hope you all understand this whole story)

If the Feliway has helped a bit, then adding enough plug ins to cover the whole house could really help. In addition to this, Pim might benefit from a calming supplement such as Composure or Zylkene. Spirit Essences/Bach's Flower Remedies may also be worth a try.

In addition to the calming measures, make sure you thoroughly clean anywhere he's peed with an enzymatic cleaner. You might find a blacklight helpful to make sure you get everywhere.

Lastly, interactive play may really help this situation - play with Lily to drain her energy so she is less inclined to chase Pim, play with Pim to build confidence and allow him to 'own' his territory in a healthy way, and play with Daisy so she doesn't feel left out.

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Thanks for your advice! 

I am thinking about buying a second Feliway plug-in and use this one in the living room. I only have my doubts since it is summer and the door is usually opened during the day when it is sunny and warm outside.
Perhaps Feliway doesn't work when the door is opened? I could close the door, but then it's gettin' warmer over here and the cats like the door to be opened as well because they prefer to go outside through an open door instead of the cat flap

I recently bought a blacklight but still haven't used it . I am going to do this very soon. I saw the places where he sprayed and I did clean it very well, with Urine Off (recommended by a cat behaviorist I spoke to), and since I start using that, he doesn't spray on these places again. He does spray on other places now though.

I have heard of Zylkene, but not of Composure. I will check if they sell it over here

And I tried to play more with both of them.. Pim likes to play usually, however, I don't know what Lily likes. She likes to run but I am not sure if she is a big fan of hunting games etc.
The truth is that when I play with her, she seems to be interested for a minute and then she seems bored and rather wants to give me some hugs. 
I have many toys and stuff and the thing she loves the most are the valerian toys. But the hunting toys should be good for her, I just don't know why she is only interested for a minute or so :S.
 

Have you got a Da Bird or Flying Frenzy? They really are the ultimate wand toys, and they have a virtually endless range of attachments.

Zylkene and Composure both work on the same principle, they're just different formulations by different companies. I'd never heard of Composure until I joined TCS. It seems to be the favoured version in the American market. I've never had the need to use either myself, but I've heard very good things about both of them.

Good to know about composure and Zylkene Definitely keep that in mind.

I have a Flying Frenzy. Daisy LOVES it..Lily likes it sometimes. Sometimes she only has that hunting attitude you know, like she is going to attack. But then sometimes she is either losing her concentration or she catch the 'prey' and she is done. 
Perhaps she is a very good hunter (she never brought me a prey so far though), and I have to make it a bit harder for her. I try to use the techniques they recommend. When I use the Flying Frenzy I try to act like it is an actual  prey, by not moving it towards her head e.g. , because a prey would never do that too.

It is just like she loses focus so fast..But I will keep trying
I don't know Da Bird. is there are certain difference between these two?

I think the primary (if not only) difference is that Da Bird is American made and Flying Frenzy is British made. You could always try a different attachment on it for Lily - different cats go for different materials. It's definitely worth experimenting a little.

I will keep trying And I found more information about Composure and people are pretty positive about it. I can also buy it online so I think I'll give it a try The only thing is that it says that you have to give the cat one chew per day. Hopefully they are a bit tasty because giving medication to Pim is quite stressful to him. But if he doesn't like it I can always cover it with Easy pill if  that is possible Works great for Pim.
thanks for this tip!

Composure comes as a liquid too, which is sometimes easier to give. Apparently most cats take it pretty well in their food - you can always use something extra yummy with it if needed. I hope it works well for you

I definitely agree that Lily and Pim should both get more play. Also, can you added more wall shelving for Pim so that a) he has multiple avenues to get away from Lily rather than getting cornered/trapped somewhere and b) since sitting up high and looking down helps build cats' confidence? That might help a little with his territorial insecurity. 

Thanks. I have multiple avenues but I think I could have some more, especially upstairs.

It is so strange, just don't understand..This morning I went upstairs and Lily was sleeping in her bed, which is placed on a cupboard. I have another cat bed on the floor, next to the cupboard where Lily sleeps. This cat bed hasn't been used a lot since I still have to find a better place for it.
But now Pim was sleeping in it!
So Lily slept in this bed on the cupboard, about 3 feet high, and Pim slept so close to her, on the ground. They were both very sleepy.

It surprised me a bit because you'd say Pim trusts Lily..  And Pim usually sits up high,  especially when Lily is in his surrounding. 
They also greet each other..it's just that he doesn't like it when Lily wants to play which makes him stressed - obviously - but on the other hand, he seems to be okay when they sleep next to each other on my bed etc.

It really sounds like he has an issue with Lily's more extreme/dominant behaviour rather than Lily herself. This is actually really good news, as it suggests that it won't take a huge amount to get the two to be peaceful all the time. Drain Lilly's energy regularly, boost Pim's confidence and reduce his anxiety, and you should have a calm and happy household....albeit one with a very exhausted owner!

I have every confidence that you'll get there sooner than you think :nod:

Thanks ! I hope Pim will feel more confident and he isn't so stressed out. We are going to work on that and I have faith that things will get better soon !