Humiliation Assignment 9: Letter to Santa

Written humiliation assignmentToday’s lesson in humiliation will feel a little different from all the others.  There will be no bobbing in the toilet, no shaming yourself in public, and no freezing your balls off.

However, you certainly will get an equal dose of embarassment, just in a different way.

Today’s task is a humiliation writing assignment.

First, either sit at your computer or grab a pen and paper.  You are to compose a letter to Santa in order to inform him what you’d like for Christmas this year, just like you used to do when you were a little boy.

You and I both know that you’re totally underving of Santa’s generosity though, don’t we?

You deserve nothing.

Start the letter by explaining to Santa what a whore and/or loser and/or pervert and/or sissy you were this year.  Remind him that, because of what you are, you deserve absolutely nothing from him, or anyone else.

Next, tell him that instead of bringing you gifts, he should reallocate his gift-giving to your wonderful Mistress, Charlotte.  Explain how much better I am than you, and why I’m much more deserving.  Try including a few suggestions of specific gifts you think he should make sure are in his sack for me.

I want degradation, creativity, and honesty.

Whether or not you succeed at this assignment will be based entirely on whether or not your letter is both a confessional and an original, creative work.  Put some thought into it, and make it worth my time since I’ll be the one reading it.

How to submit your assignment:

You’re welcome to write by hand and scan a copy to send to me, or you can just type it up  and send it off to thephonesexmistress (at) gmail.com.  Gold stars will be awarded for those who are bold enough to leave their letters out in the open as a reply to this blog post.

Whether you make your letter public or not, take the time to leave a comment about how this assignment made you feel.  It’s the only writing assignment of The Twelve Humiliations of Christmas, so I’d love to hear your impressions.

15 thoughts on “Humiliation Assignment 9: Letter to Santa

  1. Dear Santa,

    This year had not been especially kind to me, nor you for having to keep track of me. Where to begin but with the most devastating news to my manhood, my break up with Jennifer.

    As you knew since time immeroable, Santa, I never had a girlfriend until I was 28. I’d never even been on a date. Well, I thought I was so lucky to convince Jennifer to go out with me. Could it be that I’d take my name off your loser list?

    Of course not, after-all I’m still a sissy. Now, she knew I was a girly guy but she’d never seen me in makeup until she surprised me with a visit to home one day. When she first saw me wearing my pink lipstick, she cried her way back to her car, never to talk to me for days on end.

    She could not believe she was dating such a sissy. I couldn’t have sex with her without being a slut, begging her to do me in my sissy hole.

    I so horrified this poor woman who I loved, and envied for her looks. That’s why, Santa, I’m suggesting that whatever gifts of pity you would have given to me, you give to the wonderful Mistress Charlotte!

    I have only known her a short time but she has been patient and warm to me, even though I’m such a lousy sissy.

    If I wanted a Christmas miracle I would have wished for becoming a more feminine beauty. Instead I’ll stay as ugly outside as I’m stupid on the inside to let you pamper Mistress Charlotte to her heart’s content. She has the looks I envy to make any outfit I would die to fit in work for her.

    So, Santa, give a Merry Christmas to Mistress Charlotte. I’ll just look at pictures of sissies and sluts on the internet, wishing I could be as dirty as them. My christmas cheer will be my sissy hole plugged to full and I’ll put a wiggle in my step for the pleasure of Mistress Charlotte’s attention.

    Sincerely,
    Dominique

    • Dominique, this is by far the most humiliating letter I have ever seen! Bonus points awarded for typing it up so quickly after the assignment was issued. It’s as if you knew you had no choice but to confess. I am so pleased.

      I especially like the part where you recount the time you absolutely horrified Jennifer with your sissy antics. Hilarious!

      Thank you for your kind words about me. It’s always a treat for me to find out submissives are paying attention to how superior, smart, and beautiful I am. As they should.

  2. Dear Santa

    I am writing to ask that you allocate all my gifts to Mistress Charlotte this year. As you know, I am underserving of any gifts because of my pathetic sissy behaviour. Every Friday when my beautiful girlfriend is at work, I get all dressed up in sexy underwear and spend the day fucking my sissy pussy with a dildo. If @BlackHatLee lets me, I then cum on the floor and lick it up. Finally, I post pictures of my misbehaviour on Twitter in the hope a Master or Mistress will take pity on me and encourage my sissy antics. Mistress Charlotte has done just that! She is supportive and kind, so I would like her to receive all the sexy clothes I wished for – she would of course look much better in them than me anyway.

    Love, 79_Sissy

    • How humiliating that you would post this here for all the world to see! That puts a giant smile on my face this afternoon. Well done, 79_Sissy. I certainly hope Santa honors your request and brings me lots of clothes this year.

      This @BlackHatLee sounds like an interesting character, to say the least. I’ll be keeping an eye out for both of you on Friday.

  3.  Dear Santa,
     
     
    This is the time of year when I normally write to you to let you know what lovely things i’d like to bring me on christmas.  This year I’m writing to tell not to bring me anything this year because of all of the dirty and perverted things i’ve done this year. 
     
    Now I know you have your elves keep an eye on us all year round and report to you if we have been good or naughty boys this year.  I’m a bit concerned that your elves might have been to disgusted to watch or too embarassed to give you repeat the filthy things I’ve done.  I won’t tell you everything as you’d be reading this until boxing day and that wouldn’t be very fair on all of the good boys and girls.
     
    I did try and be good but i’m obsessed with humiliating myself for the amusement of women.  I can’t help making a fool of myself just to hear a them laugh at me for being a loser. They send me on silly errands to buy embarrassing items like ladies underwear, sex aids and even a blow up doll and admit that they are for me. I’m made to dress in embarrassing outfits and degrade myself.  You might have seen some of the photographs (yes that was me in the dog mask playing fetch),  and you probably know about the websites and phone lines I visit.
     
    Now you know why you shouldn’t come this year can you please please please visit Mistress Charlotte and give her some extra presents.  She really is a wonderful, beautiful, creative, intelligent and kind Mistress who is in superior to me in everyway deserves all the presents you can give her for having to keep worthless creeps like me in line.  I’m sure you’ve had lots of letters already telling you this how fantastic she is.  I’d like very much if you could take her a:
     
    Keurig B-60 Special Edition Gourmet Single-Cup Home Brewing System. 
     
    The lastest smart phone that your elves can make so she can keep an eye on her subs and sissies.
     
    A  luxury 2 week holiday to the caribbean.
     
    Some chocolates and diamonds in her stocking…. on oh don’t forget the tangerine as well.
     
    Thank You Santa
     
    Bobby
     
    P.S.  I wouldn’t even bother getting your elves to watch me this year as I’ll probably be even worse.

  4. This task was not that much different to the others in as much as the other tasks have involved making confessions in writing. I have viewed these reports as being as important if not more important than the tasks themselves and writing them humiliating in their own right. This report takes that a step further in it’s humiliation as the confessions are more personal and not based on a description. I did dither a bit on including a couple of the details but I hope you were pleased with the result x

    • I adored your letter to Santa, candy girl! I’m especially pleased with your gift suggestions for Santa and his elves. Like a good sub, you’ve been paying attention all along and developing a sense for what I like. Bonus points, and lots of them, awarded.

      That said, you’re still indeed a loser, so don’t get cocky and feeling like you deserve something from Santa after all. You don’t. 🙂

      A blow up doll? HA! Playing fetch in a dog mask? PRICELESS. My Christmas wish is to go back in time and witness these shameful events for myself. I can’t resist a great laugh, after all.

  5. Mistress, here is my letter to Santa for you

    Dear Santa

    Hi Santa, I know you are always watching everyone so just in case you missed me this year I am writing to tell you that I deserve absolutely nothing for Christmas this year, there are many reasons for this, but mainly I’m a pathetic excuse for a man. I get aroused by wearing womens lingerie so I suppose I am a sissy, I also get turned on by women laughing at me and treating me like a loser (which obviously I am) When i’m walking round the city centre I always gaze at the various stores and clothes and daydream about being forced to model them, even makeup counters. I stare at envy of women on the streets with perfect makeup, and often use things i’ve seen as material to think of fantasies to masterbate about.

    Earlier this year I even went to a massage parlour and paid the lady in there to humiliate me, she did, and also exposed me to the other girls working there my non-cock was compared to lots of different things, from a tube of lipstick to a cigarette lighter. It was so shameful but I was incredibly aroused. I have had only 2 dates all year and they didn’t work out. Everyday I seem to drift into a fantasy world where I am serving a beautiful Mistress who controls me. Life in the real world takes a back seat, sometimes I even ring phone sex lines and beg for humiliation, I truly am pathetic and deserve nothing at all (unless permanant humiliation comes in a box)

    I would ask you though Santa to make sure a really perfect person has the Christmas of their dreams this year, I am talking about Mistress Charlotte who is vastly superior to me in every way, I have been humiliating myself for her amusement lately and find myself thinking of her tasks any chance I get. She deserves the world, although I know that would be hard to wrap, but certainly anything you had for me should go to her. Any pretty lingerie would obviously look far better on her, maybe even a nice diamond necklace as she certainly is a diamond among women. I would really like for any toys that could help her humiliate us losers to be given to her, as well as some fine wine and food so she can have a perfect evening whenever she desires. Most of all Mistress Charlotte deserves loyalty from slaves as she can be their total addiction, Perfection in every way, I guess the complete opposite of me.

    Santa I would also ask that you take care of anyone who lives in a warzone this Christmas, and anyone who has any forms of illness. Anyone who has been made homeless in the recent “banking crisis” and even elderly people who have no-one to be with over the festive period.

    Thankyou for reading my letter Santa

    From supersubG

    I hope my letter is satisfactory Mistress, I sometimes struggle to write down exactly what I want to say, but I must say that reading this back makes me feel embarrassed, but still i’m aroused by it all, I don’t know why, I just know that in my head I need to keep doing this.

    • I’m impressed, supersubG. I found the final paragraph of your letter very touching, and a good reminder that even though I have submissives to give me everything I ask, it’s still important to think of those who have very little this year. It looks like you have at least one redeeming quality, and that is your concern for the well-being of others globally.

      Either that, or you’re already positioning yourself to get back in Santa’s good graces in 2012. 🙂

      Anyway, I found the remainder of your leter highly amusing, especially your confession about paying for humiliation phone sex, as well as having your size mocked and made a joke of (as it should be) in a massage parlor. How pathetic!

      As a whole, these letters to Santa have been very revealing (yours is no exception, supersubG) and I’m enjoying how candidly you all have been sharing your most embarrassing moments on a public blog, all for my amusement. I keep going back to read each and every one of them over again, and laughing just like it’s the first time. I fear my face may hurt from smiling soon.

      • I do like to do whatever I can to help other people Mistress, maybe it is my one good quality, but to me it just feels right to do it, I’ve been pretty seriously ill in the last couple of years, but I’m ok now, but the time I spent not really able to do anything gave me plenty of time to think about the sufferings of many people here and abroad. And compared to some others I am lucky, (and extremely thankful for it)

        I’m glad the rest of my letter amused you though Mistress, it was very embarrassing both typing that up and also reading it back to myself to check it over!

        • I’m sorry to hear that you weren’t well, and very happy to hear that you’re better now. Besides, it would be hardly any fun to torment and torture you if you weren’t at full capacity.

          Anyway, go back and read your letter once more, and really contemplate the shameful things you’ve made public knowledge today. 🙂

          • Oh my i’ve read it again this morning Mistress, I can’t believe some of the things i’ve admitted, really embarrassed about it. I actually feel a bit ashamed by it. This morning I nearly got caught in my panties from Day 1’s assignment and the whole of the last few days events are running through my head, I must concentrate on getting the Secret Santa gift this afternoon!

            PS would it amuse you if I fill out @SissyFacts application, I wanted to ask permission before just doing it

          • I love that you almost got exposed in your new Christmas panties!

            I would love for you to fill out @SissyFacts’ application. I can’t imagine why she would choose someone as pathetic as you, but it will amuse me for you to have to answer the questions on the application. Do it today.

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