CruelGF - Jessie Boulevard - Dressing You For Date-Night

Are you ready for my new sissy humiliation assignment? Are you ready for me to send you out into public to carry out another ego-crushing feminization task for me? You know how much I enjoy putting you humiliation addicts through the most embarrassing of situations right? You know I record, save and use all of the evidence I gather while you're performing these acts of humiliation for me, don't you? Well so long as you understand that by completing these public-humiliation assignments for me you are running the real risk of complete exposure, blackmail and financial ruin you may carry out The Five Dress Challenge. The rules are simple sissy. You will put on your very best girlie lingerie. Stockings, suspenders, matching bra and pantie set - the most feminine things you have. Put a nice long blonde wig in a bag with some lipstick and then head to the mall. I want you to hunt out the store all the bratty princesses love to shop - Find a Forever 21 or a New Look or something like that. You're gonna look so out of place browsing all the cute girly clothes but I want you to take your time to find a pretty pink dress. We're going date-night dress shopping and I want you to find something cute and short to take to the dressing room with you. Your challenge is going to be to take a selfie, to share with me, of you trying on your date-night dress in the changing room. Take the wig from your bag and put it on with a nice thick application of lipstick. I want to see you modelling the dress for me, pout, flick your hair and make sure I see the label and that you're clearly in the stores changing room! Congratulations sissy - you've completed part 1 of your 5 dress challenge!

MP4 * 703 MB * 00:12:01 * 1920x1080

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