Cross-Dressing and Sissies

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

For many outsiders…the world of fetishes seems like the land of clichés, and that may be true to a certain extent. Fetishes inflate stereotypes, specifics, and fascinations to far-flung reaches. But in the area of fetish reserved for those who wear clothing that belongs to the other gender, clichés become very revealing. Take for instance the saying “It’s a man’s world.” Women have worked very hard over the past 100 years or so to turn that phrase upside down – but in the world of cross-dressing fetish and sissy-boys, it’s a woman’s world indeed. Or a man’s world, depending on how you look at it…

This chapter is primarily geared toward straight males, though if you’re neither straight nor male but enjoy fetishizing opposite gender items, you belong here too. If you’re in unclear gender or identity territory, relax – and pick up a copy of My Gender Workbook by Kate Bornstein.

Cross-dressing isn’t typically a politically correct fetish…what some people find unnerving about this fetish tends to be the gender stereotypes and exaggerations inherent in the fascination with what makes, say, a woman a woman. Sometimes the way cross-dressing manifests itself may not be pretty (ahem), or it might even be downright offensive, and it might even make it seem like the man with the fetish has a negative way of perceiving women…Just because a man likes to be made into a sissy maid and called a slut doesn’t mean he thinks all women are submissive whores. In fact it might be the exact opposite. Many men who like becoming submissive females would prefer doing so with female dominants; others may find having a female partner wear a strap-on thrilling; a few might want to “go all the way” and try sex with an actual male partner. A good number of cross-dress fetishists see women as powerful, deserving of respect, mysterious, and all-knowing. This seems like a contradiction, and it is, but it makes perfect sense to the man in the panties. For them, cross-dressing is a manifestation of awe and desire for the opposite sex.

Wearing women’s clothing and/or makeup is an entry into a hidden, forbidden world. For men, it is full of secrets – sexy secret. From makeup tricks to walking in heels, squeezing into tight but soft undergarments to assuming a submissive sexual role – it’s all very far from the world of men, and what it means to be one. A man might see female clothing on his body as making him feel sexy, sexually receptive, okay to let someone else call the shots, or a fun way to play with “lesbian” fantasies, using his giant clit (penis) for fun and games with his new ‘girlfriend”. Taken further, it’s permission to let go, not make decisions, to get slapped around or get sexually “used” as a feminine sex object that is so desirable that no one can hold back their lust – they just have to “take” what they want with her. Women lead very different sexual lives than men; he might just want to “try on” how the other half lives for a change. It’s all about perception, of course, and fantasy, but it’s all sex play between adults. And that’s how to have fun with it; just play.

Elements of cross-dress fetish, to be enjoyed solo or in combination – use your erotic imagination:

• Women’s undergarments: panties, corsets, girdles, nylons and pantyhose, bras, crotchless hose and panties, bloomers, ruffle butt panties.

• Other women’s or sissy wear: aprons, skirts, dresses, slutwear (tight and revealing spandex, miniskirts, porn star lingerie), cutoff shorts and cutoff tank tops, elegant gowns, maid’s outfit, uniforms like cheerleader or nurse, female submissive gear, any female rubber garments, gloves (such as opera length), girlie socks, pinafores, petticoats and frilly hats, sweaters (cashmere, angora), earrings, ladies or little girls’ jewelry.

• Makeup: lipstick, full-face makeup

• Women’s shoes: high heels, platforms, “fuck-me” pumps, stripper shoes, go-go boots, thigh high boots, “hobble” shoes and boots (typically ballerina-style toes, patent leather), Mary Janes, mules (especially feather trimmed marabou), open-toed sandals, pumps with a slave lock or D-rings on the ankle, stilettos, and spike heels.

• Hair: styled or a wig

• Partial or full body shaving

• Outfits/roles: maid, slut, little girl, sissy, princess, schoolgirl, guy in panties, businesswoman, super-heroine, nurse, cheerleader, hooker, waitress

• Scenarios: female service roles, female sexual-service roles, forced feminization, punishment with feminine clothes, getting “caught” in the panty drawer or trying the lipstick, being “discovered” wearing frilly undergarments beneath masculine clothes, being an animal of another gender, role-playing, age-play scenarios, “forced” sex scenarios, dominated and sissified husband, little boy made into little girl, learning what it takes to be a “real woman,” discipline schedules, panty punishment

• Further feminization: tucking, prosthetic breasts, cleavage bras, sanitary napkins, strap-on discipline, hair removal

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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