What is a Sissy Boy?

excerpt from Violet Blue’s Fetish Sex – An Erotic Guide for Couples:

If you’ve never heard this term in a fetish context before, it’s easy to think this is a schoolyard insult, or a derogatory gay slur; actually, this context fits its present use in defining the sissification subculture – and it’s bigger than you think. Sissy-boys are submissive males whose role-play is based around a desire to be trained at becoming responsible, disciplined girls or women at the stern and firm hands of a superior; sometimes a pro domme, a partner, or their lover. Cruel schoolmates call effeminate boys sissies; adult sissy fetishists may react to the label in a variety of ways (pride, humiliation, shame, arousal0, but taken one way or another it’s the term for the submissive feminized male. A significant portion of the sissy culture is devoted to age play, that is, the adult male sissy enjoys playing as a little girl or sometimes a female baby – this is AB play, or adult baby role-play…This chapter is primarily geared toward grown-up sissy cross-dressers, especially the naughty husband and sissy maid.

Some sissy boys get feminized, others don’t. Most get humiliated and punished for infractions and weaknesses of character, both real and imagined. Sissies are often forced to cross-dress. Regardless, sissies always value the superiority and value of a woman, and seek to become like her through worship, service, and discipline.

What happens to sissies:

  • Sissies require constant reminders of their place, which is groveling at your feet.
  • They get smacked in the face or on the rump when they misbehave.
  • They are “made” to dress up in things like makeup, perfume, frilly undergarments, teen and training bras, knee-high socks and Mary janes, catholic schoolgirl uniforms, maid outfits in rubber or satin, party dresses, press-on nails, and high heels.
  • You can make sissy put on shows for you: dancing, stripping, singing, or “clit milking.”
  • Sissy’s discipline comes from doing his chores; dress him up and make him do housework.
  • Put panties on your sissy and make him scrub the floor or give you a pedicure.
  • Teach sissy to do your hair and makeup, and help yopu get dressed.
  • Sissy maids get special uniforms but must adhere to strict behaviors, even while doing housework and chores. You may decide if your sissy gets punished for infractions or good behavior, but be consistent – sissies are impressionable and only understand repeated behavior training. At home, plan a special maid’s day where sissy is a maid all day long. You can make sissy wait on you and your girlfriends for an afternoon of tea, or you can lend sissy out to your friends for their entertainment and special training. Read advanced sissy-maid training techniques in A Charm School for Sissy Maids and The Mistress Manual by Mistress Lorelei.
  • Make sissy wash all your dirty panties or polish all your shoes.
  • Scold and humiliate him for being such a sissy; point with your finger and make fun of his tiny sofft little clit (but it might not stay tiny or sofft during the berating).
  • Fuss over your sissy; forcibly fix his hair, wipe smudges from his face, cruelly adjust his clothing.
  • Sissies get spanked. A lot.
  • They also get strap-on discipline.
  • They get panty punishments of all kinds – read on.

Forced feminization tips for the dominant partner:

  • Use many of the above feminine punishment suggestions for your scene, depending on what you negotiate with your submissive will enhance the experience of being forced into womanhood.
  • Think about the feminization beforehand and be sure you assemble gear, clothing, makeup and other accoutrements to create the sappiest, most cliche version of femininity possible, especially if humiliation is an important part of the scene.
  • Map your scene in at least four basic parts: establishing your dominance, forcing “her” into her feminine clothes and makeup, a climax that involves transgression and punishment, than a finale where the girly redeems herself through sexual service and rededication to her mistress.
  • To set the scene, lay out all the things you’ll use, and create suspense by having hidden tools at your disposal that you allude to, such as a special hairbrush for mistake corrections (spanking) or panties for gagging sissy girls who mouth off or cry too much.
  • Begin by explaining who you are and her role; maybe you’re a headmistress or goddess and she needs tto learn to be a real woman – or is a slut needing to be taught a lesson.
  • Dress her up and put her makeup on, explaining everything along the way, reminding her that you’re introducing her to the mysterious world of women’s secrets. You can make it hurt if it pleases you.
  • Make her perform a task for you: dancing, a striptease, tea service, laundry.
  • If she doesn’t fuck it up somehow, stick out a leg and trip her.
  • Tell her she has a lot to learn as a woman and you’ll have to teach it to her. Then punish in a previously agreed upon manner, such as panty gagging and whipping, or strap-on teaching so she can learn to service a man (cocksucking and ass-fucking), or crawling on her hands and knees while you ride her.
  • Angrily try to fix her hair and makeup afterward.
  • Tell her she can make it up to you, explain exactly how, and have her do so immediately – never withhold forgiveness after a punishment unless you’ve agreed on this beforehand, as this can be a particularly cruel emotional punishment.
  • She has earned the right, through pain and humiliation, to perform an intimate task for you. have her make it up to you by servicing you sexually – instruct her in the oral ways of “lesbians” so she can learn to please you correctly. Or, have her give you a massage or bathe you.
  • Tell her what a beautiful girl she is and that you are pleased. If you so choose, you may tenderly remove her makeup and dry her off after she bathes. You may also allow her sexual release, if it hasn’t already been part of the scenario. You can also continue the scene until you decide she may have an orgasm – as long as you like.

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Violet Blue is an author, editor, robot mechanic, female porn expert, and professional pro-porn pundit. This article was excerpted from chapter 7 of her book Fetish Sex – An Erotic Guide for Couples which is available here.

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