I am so sorry to hear about your loss of Winston. Here's a poem I hope you find comforting in time. I found it the day after we lost one of our boys this past January - he was 12.5. Time will heal your heart.
Do Dogs go to Heaven
My little bully passed away, no more breathe a sound.
I held him for the last time, then entombed him in the ground.
Day and night I wept so much, in tears I thought Iād drown.
I searched my soul for comfort, but no peace therein was found.
In great despair, I hit my knees and then began to pray.
āFather will I ever see, my dog again someday?ā
I raised my eyes and saw an angel standing near a gate.
I sensed an inner peace Iād never felt before that day.
The angel smiled and said to me, āOh man of little faith!
God sees every bird that falls; He knows your bullyās fate.
I have met your little dog, I saw him pass my way.
Your precious dog is still alive; he just walked through this gate.
Paradise is lovelier than you can comprehend.
No pain or grief, no tears or fears, and life will have no end.
God gave to man His only Son, to cover all his sins.
So why would God withhold from you your pure and loving friend?ā
The angel took me by the hand and said, āNow come with me.
A glimpse of paradise Iāll give, to you so you can see.ā
Through the gate and oāer the Rainbow Bridge we did proceed.
Through green valleys filled with flowers, rolling hills and trees.
āWow, so this is paradise!ā The place was filled with joy.
I saw my bully playing there, with dogs and cats and toys.
He also had some doggie treats, and food that he enjoyed.
Heād made a lot of new friends there, including girls and boys.
Then I saw a child come near, and hug my little mate.
She said to him, āI love you so,ā and kissed him on the face.
The angel said, āThe child just crossed the Rainbow Bridge today.
Now she needs a little friend, to love and help her play.
Godās love for her would be enough, in that make no mistake.
But in His love, He knew full well, the child would want a mate.
This is why God called your dog unto this splendid place.
Godās entrusted her with him, ātill you pass through the gate.ā
I pleaded, āMay I hug them both?!ā The angel answer, āNo!
Youād violate a sacred site, and now itās time to go.ā
He led me back across the Bridge and through the gate to home.
He left me there with new-found hope and peace within my soul.
If someone ever asks what happens to a dog that dies,
Just give a gentle smile of joy and look them in the eye.
Take their hand and comfort them and tell them not to cry.
For dogs donāt die, they simply cross a bridge to paradise.
It still makes me tear up reading it even though it's been 6 months since Orion passed. I'm very co-dependent on my boys so I get hit real hard when the go to the big doggie park in the sky. http://www.englishbulldognews.com/forums/members/jakeisgreat.html
. Again I am very very sorry to see about Pumpkin Doodles passing (makes me sad for you).
Winston was a beautiful bully! Could almost pass for a brother to my boy. I hope time helps to heal your broken heart, it is just so unfair these pups dont live longer. Sounds like he was as lucky to have you as you were him. 
