\useMPlibrary[dum]

\showframe

\starttext

\defineanchor[one][text-1][hoffset=-3mm,voffset=-3mm]
\defineanchor[two][text-2][hoffset=3mm,voffset=-9mm]

\input tufte

\placefigure
    [left,none]
    {}
    {\anchor[one]{\externalfigure[dummy][width=5cm,frame=on]}%
     \anchor[two]{\externalfigure[dummy][width=5cm,frame=on]}}

\input tufte

\definetextbackground[whatever]

\starttextbackground[whatever] \input tufte \stoptextbackground

\input tufte

\stoptext
