You are using First()
Function of SSRS which Returns the first value
from the specified expression. Try this
=Fields!DocumentBody.Value
The only Bring forward the Imagies you actually need by doing something like ..
select Pic.Col1, inmate_FirstName, inmate_LastName,inmate_MiddleName
,inmate_BookingNumber, inmate_InmateNumber,inmate_DOB,inmate_Gender,inmate_BookingDate, inmate_Race
from new_bookingscreen1 OUTER APPLY (
SELECT TOP 1 Annotation.DocumentBody
FROM Annotation
WHERE ObjectId = new_bookingscreen1.new_bookingscreen1Id
ORDER BY -- Your Condition (How you decide which one is the 1st Picture)
) Pic(Col1)