This demostrates the API PathToRegion and friends to create a region out of text. To use it, paste the code into a standard form, run the project, and type some text on the form. The form's region will be set to the text as you type it.
Option Explicit

'Necessary Windows API Declares:
Private Const SM_CYCAPTION = 4
Private Const SM_CXBORDER = 45
Private Const SM_CYBORDER = 46

Private Declare Function GetSystemMetrics Lib "user32" (ByVal _
   nIndex As Long) As Long
Private Declare Function OffsetRgn Lib "gdi32" (ByVal hRgn As Long, _
   ByVal X As Long, ByVal Y As Long) As Long
Private Declare Function BeginPath Lib "gdi32" _
  (ByVal hdc As Long) As Long
Private Declare Function EndPath Lib "gdi32" _
   (ByVal hdc As Long) As Long
Private Declare Function PathToRegion Lib "gdi32" _
   (ByVal hdc As Long) As Long
Private Declare Function SetWindowRgn Lib "user32" (ByVal hwnd _
   As Long, ByVal hRgn As Long, ByVal bRedraw As Boolean) As Long

'Paths to a window region.
Private Sub Form_KeyPress(KeyAscii As Integer)

    Static sEntered As String  ' The text that's been entered
    Dim hRgn As Long           ' Created region
    Dim xSides As Long         ' Width of the window border
    Dim yTop As Long           ' Height of the border + caption
    Dim yBottom As Long        ' Height of the window border
    xSides = GetSystemMetrics(SM_CXBORDER)
    yTop = GetSystemMetrics(SM_CYCAPTION) + _
    yBottom = GetSystemMetrics(SM_CYBORDER)
    'Setup the form for drawing, note that the font must
    ' be a truetype font.
    Font = "Times New Roman"
    FontSize = 30
    FontBold = True
    BackColor = vbCyan
    'Act upon the keystroke
    Select Case KeyAscii
        Case 8 'Back space, Remove one character
            'Make sure there's atleast one character
            If Len(sEntered) >= 1 Then
                sEntered = Mid(sEntered, 1, Len(sEntered) - 1)
            End If
        Case 13 'Enter, add a Cr Lf to the string
            sEntered = sEntered & vbNewLine
        Case 27 'Escape, exit the program
            Unload Me
            Exit Sub
        Case Else 'Otherwise add the character to our string
            sEntered = sEntered & Chr(KeyAscii)
    End Select
    'Make sure the form is big enough for the text to be displayed
    Width = TextWidth(sEntered) + ((2 * xSides) * _
    Height = TextHeight(sEntered) + ((yTop + yBottom) * _
    BeginPath hdc  'Start saving the drawing into a path
    Print sEntered 'Print the text (goes into the path)
    EndPath hdc    'All done, save the path
    hRgn = PathToRegion(hdc) 'Convert the path into a region
    'Move the region so it shows in the client area of the form
    OffsetRgn hRgn, xSides, yTop
    'Finally, set the region to our window
    SetWindowRgn hwnd, hRgn, True

    'Since PathToRegion will return null if print didn't draw
    'anything, and SetWindowRgn removes the region when you pass
    'it null, we don't have to worry about hiding our window with
    'a blank region.  Also, since the path will be deleted next
    'time a path is created, and the region deleted next time
    'SetWindowRgn is called, we don't have to clean up anything.
End Sub
Sample Usage: