Every day was a different humiliation.
Since he had moved in with his Master, Spykers clothes had all been taken and locked in a chest. Everything had been replaced with frills, pink, or tight-fitting clothing that left him red-cheeked and painfully embarrassed. And, even then, he had no choice in the mater: his owner would take him before the mirror each morning, pick out his clothing, and dress him like a big doll.
It was degrading in the worst way, but every time he was hard as a rock and whimpering for more.
***
Originally set out to do this with the last pic of Roland but the pose did not lend itself well being a dress-up doll. I may try and revisit him later. Fortunately for you, Spyker came out perfectly!
I havent done something like this in years - back when I did my first sissy boy in public pic and had people vote on their favorite costume.