Hi,
Welcome and thanks for posting your to HCM.
I can understand the mental concern you are facing. After reading the whole series of event the the answers depends upon that - is your hymen is intact or not.
Now if your hymen is intact then obviously you would be having bleeding on your first night. Masturbating with pillow can never harm your hymen. And for the third part of question depends upon the object or the depth of the object used - meaning if you have used objects like pillow or related things which are not penetrating into the vagina then your hymen would be intact but if somebody used penetrating thing like even index finger thickness then the hymen gets injured.
there are many a instances where the hymen is broken with even simple injuries like cycling, running or any sports activity and there are instances where even being presence of hymen person may not bleed.
You can visit a gynecologist to get the above things checked. Even if it is broken
plastic surgery is quite a simple day care procedure which can do
hymenoplasty. As you used pillow only so there are minimal or no chance of any harm to the hymen.
hope to have provided the best possible information,
With best of hair wishes,
Dr. Sanjay K Kanodia
M.D. (Dermatology and
STD)