Barb: Spanked Sissy

I’m surprised Barbara O’Toole didn’t do more feminization illustrations. Humiliation was one of her strengths and in a F/m context sissyfication seems to be mostly about humiliation.

Barb Sissy -Spanking

Originally posted 2012-04-29 09:17:03. Republished by Blog Post Promoter

5 comments to Barb: Spanked Sissy

  • Throne

    You mention that this illo and the dildo one were atypical for the artist. Maybe they were commisions?

  • MS Becky

    I punish my husband the same way whenever whines about doing chores. Feminine attire is very effective way to create shame for my husband. He must acknowledge his lil bitch status while being spanked. To make him even more embarrassed his mother has witnessed his spanking and attire. It’s a very effective punishment tool but don’t over use the feminization as it loses it’s effect if over done.

  • smartarse

    Ms Becky…..I am not sure which is the most effective shame, a bit of feminisination (especially if he does not like it ) or punishment being witnessed by mum,
    but to combine the two….magnificant.

  • Patti


    “Stop your caterwauling, Gregory, or else I’ll get not merely annoyed but actually angry, and THEN I’ll give you something to truly cry about! I know you’ve had your naughty lustful eye on that young pretty single schoolteacher ever since she moved in next door last week, and you’ve been trying to work up the nerve to go talk to her when you’re in boy mode.”

    “Time for a reality check, Gregory. You are a thirty-eight year old ‘man’ – and I use that term loosely – still living at home with his forty-eight year old widowed stepmother because you’ve been an abject failure in every endeavor you’ve ever attempted, be it college, the army, a truck driver, a mechanic, even a damned mindless Wal-Mart greeter! I suppose a job that ‘demanding’ must have interfered with your exhaustive video-game-playing schedule. Your poor father – rest his soul – must be turning over in his grave.”

    “So here’s your situation. You know I put you in girl mode because the pedicure you gave me on Wednesday had not one but two imperfections – a minor smudge on my left foot’s middle toe’s upper edge, plus a tiny dollop of polish off of the nail on my right foot’s big toe, right below the cuticle line. I know I’ve taught you better than that. Plus, after hand-washing my delicate unmentionables, you neglected to iron them, just so you could hurry up to play that newest silly action video game. Did you really think I wouldn’t notice?”

    “I know that our young new neighbor is having several of her teaching colleagues over for an afternoon late-lunch/early-dinner social get-together in her backyard, and that she and her guests are outside grilling on her patio with only a small chain-link fence separating our backyard from hers. Given your hopeless infatuation for her – not that I can blame you for that, as she’s a very lovely girl – I do understand why you don’t want to go hang your wet laundered panties and bras and girdles out on our backyard clothes line, especially while you’re stuck in girl mode. But try and understand it from my parental perspective. If I let you off the hook every time that girl mode was publicly embarrassing for you, then it wouldn’t really be much of a punishment, now would it? How would you ever learn your lessons?”

    “So here’s what you do, if you don’t want me inviting your gaming buddies over right now to see you in that adorable outfit, and then have them watch me tan your hide even more. You put your washed wet undies in the laundry basket, you march yourself out that back door, and you hang them up on the clothesline to dry NOW. In other words, you do your damned chores without complaint, which is my condition of having you live here rent-free. If the tantalizing teacher or any of her guests acknowledge you, do not be unsociable. Smile and wave, hell, curtsy if you like – and if they beckon you over for a chat, then pleasantly explain you have to finish hanging out your underwear first, and then once you’re done, go over and talk. I don’t care what you tell them.”

    “You can tell them your wicked stepmother makes you dress up, and I’d love to hear you answer their follow-up questions as to why a grown man would allow me to do that. Or tell them that all your boy clothes are dirty ad need washing (irony much?). Or tell them you’re taking continuing education courses in Women’s Studies at the local college, and this is part of your semester assignment. Or just tell them you like pretty clothes. As I say, I don’t care.”

    “Now stop crying and fix your face; your mascara is running. Hold your head up and walk out there with pride, as though there were no shame in being a sissy. It IS who you are, much as those silly last vestiges of male pride would like to deny it. Besides, the sooner she knows what a milquetoast pansy you are, the better. It’s not fair to her to try and pretend to be something you’re not; she’d find out eventually anyway, and she’d be PISSED.”

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