Once freshly milked put your sissymaid in chastity so she can’t play with “your” toy when she’s working.
This will help your sissymaid get used to the taste of cum… she’ll certainly be gulping down a lot from here on out!
she was naughty and she needs to be punished!
Beautiful maid’s uniform!
When my sissy serves me en femme as my maid, I just sorta expect her to show up appropriately dressed, with my breakfast tray. Perhaps I should start laying out what I expect her to wear. Or maybe for special occasions, like when I have her serve me when my sister visits. Neat idea! —Mistress Heather
“I highly suggest chastity, Margo…”
This is a male chastity fantasy caption, but the picture is a lot like the first time I showed of my sissy maid husband to my sister. (Again, let me stress it had been discussed with my sis beforehand so that the “reveal was not too shocking to her. I had her consent, as I had my husband’s.) —Mistress Heather