Sissy Challenge - Tumblr Posts

9 years ago

I would absolutely love this!

My Poor Pathetic Sissy Cuckold Wrote Me A Note While He Was Out Of Town For Work. As Soon As I Found

My poor pathetic sissy cuckold wrote me a note while he was out of town for work. As soon as I found out I made him take it down to the front desk girl and have her read it and make a photo copy for her to keep. After had had told me he had done as I had requested I called the hotel to make sure. The girl couldn’t stop laughing at him and was happy to have helped in his humiliation! gooboi


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9 years ago
I Was Told By A Friend To Ask Around For Some Sissy / Humiliation Dares And I Guess She Will Be Picking

I was told by a friend to ask around for some “sissy / humiliation dares” and I guess she will be picking some for me to do and I figured this would be the best place.

Now before you send me anything please keep it realistic and not your crazy wild fantasy that no one would ever do.

I don’t have sex with men. I wont put my life, job, or friendships/family on the line. I won’t do anything to risk serious injury. I’m not into heavy pain.

Some simple / good examples I have received are things like; - Jerk off in the backyard - Ask someone at a sex shop for tiny cock rings - order pizza and answer the door wearing panties

I’d love some fun and/or creative and/or original ideas to help push me further but hate wasting my time with impossible tasks.

Thanks in advance for the help


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9 years ago

Sissy JOI

And now I'm wearing a pair of my sister's dirty panties, i have a 6" dildo in my ass, a vibrating cockring on my dick and when I cum i have to taste it. Thank you internet! **thank god for lube, this toy is huge!


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4 years ago

I'm a pathetic sissy slut

I'm a fat faggot

I'm a tiny dicked loser

I should have to serve

I deserve to be humiliated

I need to be used


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4 years ago

I'M A FUCKING LOSER

I deserve everything that ever happens to me for being such a pathetic loser

I don't deserve to be happy

I don't deserve kindness

I am disgusting

I am worthless

I am nothing


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