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Good Morning and welcome! I am Dr. Loretta, a licensed veterinarian and I am happy to answer your question.
This is a condition called Paraphimosis that is common and may require veterinary care. It is good to apply vasoline and atempt to replace the penis since it can be restricted to a point that it can block the blood supply and become an emergency situation. The steroids will nto cause this ...it is caused by sexual stimulation that cannot allow the blood to go back after this.This can be due to a stricture in the sheath or injury. Since you cannot keep this inside the sheath, it is time to take Syd to your vet for an exam to determine why this is happening and the best coure of action.
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I hope that helps....
If it is clear that it is not getting pinched off, then keep doing what you are doing by placing vasoline on it and helping it back into the sheath...you may not have to take Syd to the vet if you are making progress which it does sound like you are...Good Job!!