Sissy Jessica and some of her Humiliatin Tasks Over the last week
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Sissy Jessica’s Ultimate Humiliation Task List 🌸
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Tampon Swap for Tail:
Remove your tampon and replace it with your tail plug. Stand up straight in your slip and pantyhose, pose like the perfect little sissy you are, and hold still for pictures showing off your tail. Smile, princess — you know you love it.Time to be exposed? -
Heels & Plug Posing:
Pop your plug in, strap on your highest heels, and pose nice and proud for a full set of pictures. Once you’re done? Time to reward yourself the sissy way — with another beer or 5 as I control what and when you drink (and make sure to say “Cheers to my sissy life” before every sip). -
Toilet Pan Shame:
Sit on the toilet pan, wrists cuffed and gag in place. Snap your most pathetic photos sitting there like the sissy potty toy you are. Bonus if you’re still in your pantyhose. -
Stinky Pantyhose Car Walk:
Put on your smelliest, peed in most well-worn pantyhose, and walk outside to the car. No sneaking, no rushing — a full, proper sissy stroll, that I can monitor on your body cam. You can only come back inside once you’ve touched the car. We can then do this task again later as yo head to a shop and have conversations with people in your pissy sissy pantyhose -
Double Tampon + Tail Show:
Remove your current tampon, then insert two fresh tampons (one big, one small). Once they’re in, tail plug goes back where it belongs. Show it all off proudly for pictures, making sure that tail is on full display. -
Confession Time on the Pan:
Sit on the toilet pan, get comfortable, and call me for a recorded Confession Time. You’ll follow my script or prompts, and yes — the entire thing will be recorded for proof. I will ask some very embarrassing questions about people I select from your Facebook page, you must answer truthfully, no matter how much you squirm and beg -
Who’s the Confession For?
Don’t worry your pretty little head about who you’re calling. I’ll be picking who you confess to. All you have to do is obey. -
Cuffed Bedtime Reflection:
Lay in bed for 10 minutes, fully cuffed and dressed in your sissy gear, tail in, and think hard about your future as my pissy little sissy toy. You’re not to move — just lay there and reflect on how deeply you belong to this life. -
Gag & Heels Quickie:
Pop in your normal gag, heels on, and stay gagged and standing for 5 full minutes. Hands behind your back. Quiet, pretty, and useless — just how you’re meant to be. We can then swap the gag for the pissy pantyhose
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👠 Gag, Cuff & Heel Humiliation Tasks for Sissy Jessica 👠
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Gag Time – Quiet Sissy Hour:
Pop in the gag (bonus points if it’s oversized or drool-worthy) and set a timer for 1 full hour. During this time, you must stay dressed in your slip, pantyhose, and chastity, sitting pretty with your hands folded on your lap.
Every 10 minutes, shuffle to a mirror, look at yourself drooling, and curtsy, thinking:
“Thank you for silencing your useless sissy.” -
Cuff Time – Hop & Wiggle:
Cuff wrists behind back and ankles together with just enough slack to shuffle. In full sissy attire and heels, you must attempt to walk (or wobble) across the room to deliver a note that says, “I exist to serve.” Drop it at your feet and kneel without falling. If you stumble? Start over. -
Heel Time – Sissy Strut Challenge:
Strap into the tallest heels you own, slip on the shiniest pantyhose, and strut back and forth for 15 minutes, practicing perfect posture like a good little doll.
If you trip or loses balance, you must stop, bend over (showing off that caged little sissy clit), and say out loud, “Please punish me for being such a clumsy, pathetic sissy.” -
Gag + Heel Combo – Serve & Slobber:
Gag in, heels on, and sissy must serve drinks (or snacks) on a tray. If drool escapes, she must pause, wipe it on her hand, and smear it across her chest like cum while thanking me for letting her be so filthy. -
Cuff Time – Bedroom Display:
Cuff wrists to the headboard and ankles to the footboard, keeping legs spread wide in the slip and stockings. You stay on display for 30 minutes, heels still on, gag in, waiting quietly for inspection. And if you whimpers? She must moan louder through the gag like the needy little thing she is. Mistress will monitor you on the surveillance cam and take snapshots and videos -
Heel Punishment – Wall Sit of Shame:
Put your heels on, back against the wall, and do a wall sit while holding the chastity key on her lap. The rule? If she drops the key or stands up early, the key gets hidden away for another week. Monitored closely via surveillance cam -
Full Lockdown – The Sissy Bundle:
Gag in.
Cuffs on.
Heels strapped tight.
Slip and pantyhose in place.
Crawl into a corner, sit on your knees, and stay in position for however long I decide, looking pretty and silent, until I say otherwise. I may decide to keep you here all day as I monitor you on surveillance camera, you wont know when I take pictures and videos, all you know is that you ar emy sissy prisoner for the day/evening
These are just a few of the tasks suited to Jessica’s type of humiliation sessions. If you want to buy a humiliation package from Mistress with tasks, then send over an email at ( ukmistresslive(@)yahoo.co.uk
5 tasks =£10
10 tasks = £15
15 tasks = £20
20 tasks =£25
All tasks will be tailored to your kinks and fetishes that you will send me beforehand, as well as telling me what your hard limits are
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