Sewing his own extreme humiliation


In the first image you can see the two sissy dresses I have required him to make. The left is his summer sissy dress, the right his winter sissy dress. The summer of light cotton, the winter of long sleeved fleece. Each is an elderly lady’s style nightdress, shortened by over half the original length and a lace frill sewn at the new hem. The summer dress also has bells sewn at the hem. When he wears either, the hem reaches down only to his hips leaving his shaved boy’s bits and his bottom on full display.

The sewing took him ages – all through which he knew what the outcome of his tedious sewing would result in – deep shame. The following picture shows, on the left, his bonnet and wrist adornments (notice more bells) and on the right, shows the appearance I was aiming at. AND THAT APPEARANCE WAS REPLICATED PERFECTLY!

bonnet - drawing

When in one of his home-made sissy dresses, his bonnet, his Mary Jane shoes and frilled topped ankle socks – he looks exactly like the image of the sissy on the right. He so hates it and I am so amused by having that mortified, humiliated human doll doing some chores, or playing with his dolly or watching him outdoors, in a thoroughly timorous state, where he has been sent out to ‘play’.

I am so kind to feed his submissive soul so well. Not that you would think that given his dejected demeanour when so dressed and when doing his sewing.

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18 Responses to Sewing his own extreme humiliation

  1. Donald Jones says:

    Dear Mistress Scarlet: They look simply adorable. A the poor little thing can not hide his sweet sissy panties’ oh what a shame. Too bad for bitch boy ‘right!! I truely believe you most certainly have bitch in your total control. I would give up everything I have to be under your thumb. “Great pictures”

  2. What a wonderful seamstress he is turning out to be! 🙂

  3. fluffy says:

    OMG – I can not begin to imagine the humiliation bitch-boy must endure, especially when you have guests to laugh at him too. Sissy things does nothing for me personally, but A) your sheer disregard for what he wants and what you want is awe inspiring and B) i know for that it is actually the whole point, it is not what us slave boys want, but what you ladies want.

    simply and wonderfully awesome – thanks so much for the insights to your wonderful life

    love the bells too!!!
    much respect

  4. tallestrina says:

    What a brilliant humiliation! Sorry if this was in an earlier post but, is the sewing with a machine or by hand? Looks very neat, either way. Good luck to you both!

    • The sewing is by hand. It takes literally hours and hours. If a completed length of sewing is not up to standard, he is punished – he then has to unpick it and sew it again. I get such a sense of cruel power and ownership, glancing across as he sews for mind numbing periods while I watch TV, read a book, sunbathe, etc.

  5. Pingback: The bells, the bells | Real Life Female Domination

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  7. Bruce says:

    He must look good in his little girls dresses.

  8. Vital says:

    If a completed length of sewing is not up to standard, he is punished – he then has to unpick it and sew it again. I get such a sense of cruel power and ownership,
    Mistress you seem to keep coming up with new and novel ways to humiliate and punish him. This is one of the best I have ever heard of, and extra punishments as well as having to unpick and resow. It must have been utter misery for him completing that sewing. Then having to wear them on top of all that, and especially if you have him wear it in front of others and tell them he sewed it> Have you done that yet?

    • Yes of course he wears his most humiliating garments and accoutrements he has sewn, in front of guests and I delight in telling them he has done the sewing. My guests are always very amused at this. bitch-boy even more deeply shamed and embarrassed.

  9. maid angela says:

    Honoured Mistress. What I find most interesting about your relationship with your sissy is the way you make him do things and wear things for your amusement and pleasure with no regard whatsoever for his feelings. It is this, I think, that paradoxically results in the exquisite pleasure he will experience, possibly at the time or maybe later when he is thinking about the events of the day, from pleasing you at his own expense. I do know that in my own case the pleasure I got from when, after I had completed a particularly unpleasant or difficult task, my mistress expressed her satisfaction that the task was done and on occasions followed that with sharp canning on my bottom for taking too long.

  10. Vital says:

    Perhaps mistress you can add to his misery by making him sew his own panties and G strings. You could make him sew them in front of others, particularly sewing the lace onto the panties?

  11. sissy jamieanne says:

    Very nice Ma’am! i’m sure the tedium of the sewing and the knowledge that he will be punished if it is not up to Your exacting standards is mind-numbing and miserable! And the humiliation of wearing these shame outfits in front of Your sisters and other guests…horrifying…yet appropriate!

  12. Pingback: Cruel Xmas presents – update | Real Life Female Domination

  13. Pet says:

    What humiliations! Great drawing, I did not know his outfits are that short

    Mistress recently had a friend custom make a collar and wrist brackets of leopard skiing print, lined with with black and white lace, and a small red bow on the const. All have bells attached. Her friend have them to Goddess during a public gatherings and I was adorned in them immediately, to my extreme humiliation. At some point I considered b.b’s belled outfits here wears. I did not previously catch that he makes them

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