Tihomir's right, using a vector app like Freehand or Adobe Illustrator is the easiest way. you can convert the font into an outline which gives you anchor points that can be adjusted or added to to make your shape [see attached]

but if you want to do it in PS [or need to because you don't have any vector apps...] you can create your "tail" using the PEN tool [do it on a new layer] like suggested above and you'll be able to "mask" any part of the font you don't want showing.

i'll try to do a screen-cap of this from PS [though it's taken so time to even get this posted :( ]

:)
retrocity