Relationships & Sex
She’s not trans. She’s not in drag. For her, being a ‘Sissy’ is a bit more complicated.
Annie is a part-time girl.
A few times a month, she climbs into a pair of stockings, coats her lips in bright pink lipstick and puts on a wig full of strawberry red curls. She poses for a few pictures, taken by her wife, and together, they go out on dates as two girls in love.
Other days, however, Annie is Andrew. Annie, though, is content with this arrangement — i.e., spending more time as Andrew than Annie. She previously struggled with the desire to be feminine, feeling guilty and confused about her gender identity. But through introspection, and with the help of her wife, she found that she was happy to embrace her womanly side only some of the time, while still living day-to-day life as a man. She’s wondered whether she’s a trans woman, but ultimately, she’s decided she identifies as gender fluid and nonbinary.
A lot of people living as men feel the same way. For some, being a woman some of the time is a means of exploring and embracing the nuances of their gender identity, like Annie. For others, it’s a sexual activity, a fetish in which they’re stripped of their masculinity, and in turn, their power and dignity. For yet another subset, it’s a combination of the two, often in ways they themselves don’t fully understand.
The more fetishistic side of being a part-time woman is known as sissification. It revolves around the fantasy of a man being transformed into a hyper-feminized woman, or a sissy. In some cases, it’s a consensual play of non-consent. The man is stripped of his manhood, made to wear women’s clothing, lingerie, makeup and wigs; all the while, he turns sexually submissive. “I love it when my wife takes the dominant role when I’m in girl mode and says really hot, crazy stuff to me about being a helpless girl,” Annie explains.
For Annie, this is different than drag. “To me, drag is more of a flamboyant, showy performance for entertainment purposes. What I do feels more like a genuine expression of my identity and personality. Not that drag isn’t great—it’s just not what I do,” she says.
Some sissies are more interested in the solo experience of transforming genders. But 45-year-old Sophie Valentine is among those who enjoys the company and community of her fellow sissies more. When she’s not Sophie, she lives as a man in Greece and works as a software developer. On Instagram (where she has close to 50,000 followers), she accepts photo submissions via DM, and reposts the photos on the account. In order to be approved, the photo must be a full-length photo featuring one’s face, and per Valentine’s request and the rules of Instagram, not feature any nudity.
For her part, Valentine identifies as a crossdresser. “I want to show people that crossdressers can be as gorgeous as a woman. I want to show people what we hide inside. We aren’t just sex toys; we feel happy just being fem, girly and sissy,” Valentine writes to me via DM.
She’d like to present as a woman all the time, but the demands of her life don’t allow her to do so. Namely, she has a hectic job, and lives with roommates. “I’m still in the closet but dress as much as I can and stay that way for hours,” she explains. “When I’m out and look at women, I don’t think, ‘I want to shag them,’ it’s more, ‘I wish I was her.’”
Annie used to keep these feelings in the closet, too. At four years old, she discovered she had a penchant for wearing her older sister’s dresses. But when her mom discovered her playing dress-up, she said it wasn’t something young boys should do. So for years, Annie dealt with guilt and confusion toward her desire to sometimes be a girl. “I’d go through periods of dressing up — a lot of times as an escape, or a security blanket. It helped calm me down,” she says. “But then I’d feel guilty and purge all of my clothes and makeup. Rinse, and repeat.”
In fact, Annie thought it was something she’d have to “cure” herself of in order to have a normal marriage and family. Luckily, though, Annie’s wife of six years is accepting of her part-time womanhood. That said, she still isn’t out to everyone in her life yet, nor does she plan to be. A lot of her gender dysphoria, however, has been relieved simply by occasionally getting to be Annie.
For others, sissification is less about gender dysphoria and much more about sex. For example, the blog SissyGirlSanctuary identifies itself as “a place for inspiring positivity and embracing the femininity within,” but it primarily offers a list of porn sites with sissification videos or pornographic hypnosis videos that “force” the listener to feminize, links to sites that teach bimbo training and a guide to sites that sell lingerie and chastity belts.
Controversy, of course, follows the hypersexual nature of these branches of sissification. Case in point: Transwomen on /r/AskTransgender have discussed how men who are interested in sissification for purely sexual reasons could undermine transwomen who have pushed for validation of their identity. “Am I bothered by the porn itself? No. If that’s what you wanna get off to, who am I to stop you? Am I bothered by people thinking that it’s an accurate representation of trans people or being with a trans person? Hell yeah,” wrote one user.
Valentine is unsure if she’s a transwoman or not. But even if she is, she says she’s not in a place in her life where transitioning is much of a possibility. Plus, in being Sophie in secret, she’s more comfortable with who she has to be when she’s not Sophie—that is, just another normal guy in Greece.