Above: The beautiful TS Brooke Spears
To the uninformed, crossdressers and transgender women seem pretty much the same: people born with penises who wear feminine or female-defined clothes. They shop at the same stores. They have similar wardrobe challenges. Like all genders, they run the gamut from plain Janes to mouthwateringly sexy. But the similarities end there.
The identities, motivators, needs, and preferences of crossdressers are different from those of transwomen, yet those groups are commonly shoved under the same umbrella. Both groups grow frustrated with being lumped together on dating sites, on porn sites, and by the public. It’s important to know the difference.
Let’s start with the most basic distinction: Crossdressers, Transwomen, and Drag Queens
A transgender woman or transfeminine person is designated male at birth (born with a penis), but identifies internally as female or a blend of genders (gender-fluid). She feels this way regardless of how she’s dressed or whether she’s had hormones or surgery. This is her identity. She dresses in women’s clothes because it reflects who she is. (Note: I’m using female pronouns because my transfemme friends typically prefer “she/her” over the neutral, ambiguous “they/them.” It acknowledges their femininity and is linguistically clearer. However, if in doubt, it’s good form to ask someone about their preferred pronoun.)
A transwoman’s romantic and erotic life typically centers on her as a whole person, not on her gender status or sexuality. On dating sites, she’s more likely to be interested in a relationship than to be a checkmark on someone’s sexual bucket list. This is one reason transwomen and CDs alike find it frustrating to be treated as a homogenous group on “transgender” dating, hookup, and porn sites: it confuses the men who want to date or play with them. Relatively few transwomen like being fetishized for it—although some certainly do at appropriate times, and a few with special genetic gifts make a fine living doing so.
The terminology used for various groups within the transgender community can be complex and politically sensitive, and is beyond the scope of this article. A good reference for learning more is at https://www.glaad.org/reference/transgender.
Drag queens are men (typically, but not always, gay) who impersonate women as an art form for public entertainment, such as at drag shows or other events. Think RuPaul.
This article will talk mostly about crossdressers. These are straight or bisexual men who wear women’s clothes for personal pleasure: sensation, recreation, relaxation, and/or erotic fantasy. His dressing may be limited to lingerie or extend to full transformation including wigs, makeup, and accessories. He identifies as male and doesn’t want to live as a woman—except during playtime.
A cross-dresser who’s dressed en femme and in feminine headspace uses female pronouns and is referred to as “she/her.” Once the masculine drab clothes go back on, the CD again becomes “he.” She’ll often have a feminine name (“sissy name” or “gurl name”)—and If she doesn’t, she needs one immediately! These names are often bestowed by a beloved Mistress or playmate and cherished for a lifetime.
During playtime, the CD’s penis becomes a “clitty.” The nipples are “titties” or “breasts.” The anus is referred to as a “pussy,” “rosebud,” and other colorful words. This is especially true of sissies.
Crossdressing is often focused on the erotic and/or submissive experience, especially among those who visit Mistresses or frequent BDSM events. The guy coming into a dungeon for a session that eroticizes feminization and/or considers it humiliating is more likely to be a crossdresser than transgender.
To simplify: for a transwoman, being female is who she is. She dresses and comports herself to reflect what’s inside. Crossdressers step into feminine clothes and female roles for personal pleasure, comfort, and play… and then step out again. It’s a place they visit, not a permanent home.
And those visits can be such fun!
Above: The gorgeous 'Rachel'
Why Do Men Crossdress?
Humiliation: Erotic humiliation is a common motivator for crossdressers who are into kink and BDSM. However, this represents only a portion; many crossdressers don’t consider feminization humiliating or even necessarily erotic.
Sensation: Women’s clothes offer softer fabrics and more comfortable styling. For some CDs, it may be the compression of a girdle or pantyhose, or the sublime sensation of lingerie and stockings (especially over a freshly shaven body), or the light bristling of a petticoat.
Relaxation and escape: Stepping into panties allows him to shed the burden of masculinity for a while and immerse himself in soft, colorful, sexy fantasy. He may find that it calms him or releases suppressed elements of his personality. A reserved engineer gets to act like a flirtatious party girl for a few hours. A domineering executive may become quiet, demure, and obedient.
Personal expression: Women can express themselves visually in infinite ways: lingerie and clothing styles, bright colors, nails, hair, makeup, accessories, and mannerisms. Men have few such options. Experimenting and creating a personal style from such a vast array of choices, even in secret, offers CDs a creative outlet.
Travel into another world: Like Alice through the looking glass, crossdressing gives CDs a different way of relating to women. By stepping into the feminine role, they attempt to see the world through a woman’s eyes and imagine how they would behave in a woman’s body.
Taboo crossing: Crossdressing is a transgressive act in our society. It involves breaking boundaries and blurring social constructs of identity. To many CDs, feminization represents self-empowerment and autonomy, a giant “fuck you, I’m going to do what I want” to the world, even when done in private. When one’s daily life requires strict adherence to social expectations, breaking free of them can be liberating.
Crossdressers, Dating, and Social Interaction
Most crossdressers remain closeted in their daily lives, but long for some form of connection. They often fantasize about meeting others and going out in public dressed. Many look for friends and playmates on hookup apps, dating sites, and social communities like Circle of Q [CircleofQ.com], where they can chat, play online by webcam, or arrange to meet in real life.
The types of social connection they want vary. It may be simple e-mail or chat friendships with others who share the same interests. Some might want to wear panties while masturbating on cam. Many fantasize about finding friends to dress up and hang out with… maybe in a private location, maybe out to dinner, maybe cruising a night club to pick up men.
CDs love the idea of being an object of lust and desire. Sissies, in particular, crave opportunities to service a male top. They dream of being on their knees sucking cock, or used and pounded anally like a fuck toy—whatever Mistress or Master wants them to do.
Read the full version in Darkside Magazine Issue 29
Ava Durga is co-founder of Circle of Q, a social community and dating site for crossdressers and male admirers. She dressed her first sissy in 2001, is proprietress of The Sissy Parlor, and runs crossdressing Meetup groups in South Florida and Las Vegas. Ms. Ava advises male clients worldwide on accepting and exercising their desire to explore their inner femme. Extended bio: https://circleofq.com/about-ms-ava-durga/