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All photos by Molly Matalon

'I Cross-Dress. Do You Still Love Me?’: The Secret Lives of Sissies

Jonathan Parks-Ramage

Jonathan Parks-Ramage

Sissy men don't try to 'pass' as women. For some, the thrill and exuberance comes from being forced—typically by a dominatrix—to wear women's clothing in public. For others, it's just kinky fun.

All photos by Molly Matalon

Ken spent the majority of his adult life working as the facilities manager of a high school in Michigan. Ken was responsible for routine maintenance, building repair, and the beautification of athletic fields. No one ever suspected that Ken harbored a deep secret: He fantasized of being forced into women's clothing by a female dominatrix. Ken viewed his cross-dressing kink as a crucial facet of his identity, but feared that no one in his small Michigan town would understand. It was this need for understanding that inspired Ken to travel over 2,000 miles to attend "Sissy Night," a unique BDSM event in San Francisco hosted by noted dominatrix Alice In Bondage Land.

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"I like 'forced fem,'" Ken explains to me in the backroom of Wicked Grounds, a famed Bay Area "kink cafe" and the location of Sissy Night. "Somebody who has to be forced to look like a woman, against their will...and into the bondage area."

Ken wears a black T-shirt, dark jeans, and speaks in hurried, clipped sentences. He made the trip to San Francisco completely alone, a sort of BDSM pilgrimage that was the first item on his post-retirement "bucket list." He seems both thrilled and slightly terrified to be here, surrounded at last by men who share his desire.

Dee

Ken, you see, is a sissy. Most individuals think of the term "sissy" as a macho epithet utilized by schoolyard bullies. Yet on Sissy Night, the word takes on a different meaning. In the BDSM community, "sissies" are men who cross-dress, often for sexual pleasure. Many of these men engage in "sissification" or "forced feminization," where a female dominatrix will switch her male submissive's gender role. Though every sissy/femdom relationship is wildly different, the common denominator is usually the forced cross-dressing of the male submissive—anything from lingerie to evening gowns. Some "sissies" simply enjoy dressing up, and have no interest in BDSM. Others desire a kinkier feminization, one that is accompanied by spanking, pegging or bondage.

Growing up I always had a bondage fetish. I remember playing cops and robbers games with girls. I think it materialized in the fact that I wanted to be the damsel in distress the whole time."

It is Ken's first time at Sissy Night, but he is instantly embraced by the attendees. After our interview, a dominatrix wielding a wooden paddle cozies up to him and the two chat like old friends. Sissy Night is qualified as a "munch," which is a BDSM term for a meet-up in a public place that serves food. Wicked Grounds is a common "munch" location in San Francisco and hosts events for many different factions of the BDSM community. In most respects, the venue resembles your typical cozy/shabby coffee joint: freelancers sit on mismatched furniture, working on laptops and eating food. But tonight, behind a red curtain that separates a small backroom from the rest of the shop, sissies are assembling.

"There's a confessional aspect to 'munches' sometimes," says Alice In Bondage Land, the femdom hostess for the evening who is decked out in a floor-length rubber gown and tight corset. Despite her extreme attire, Alice's demeanor is overwhelmingly kind, a sort of BDSM momma bear looking out for her sissy cubs. "There is the pretense of sharing a meal together, which normalizes the awkwardness of strangers meeting and having very intimate conversations," she says. "It's a way to get to know people without it being in a sex club or a bar where there's a pressure to hookup."

There is a sense of warmth and camaraderie at this particular "munch." Men help each other with makeup, squeeze friends into latex catsuits, or adjust the wigs of strangers. Sissy Night is a safe space where these men can embrace their authentic nature in public—a luxury most don't have in their daily lives.

I don't go around work in a dress. But I did get ready for Sissy Night at work, and blew the security guard a kiss.

"There are a lot of people here who are deeply closeted," says Alice. "This venue lets us arrive however we're comfortable in the outside world, then change into whatever selves we want to be for the night. There's a lot of people who are in a relationship or come right from work or don't want their neighbors to see them walking to their car [in women's clothing]."

Annelise

"Rose" is one of the first men to appear on the scene, and does not arrive in female attire. He is in his early 30s and—with his stocky build, baritone voice, masculine garb, and black messenger bag—it seems as if he has stumbled into the wrong room after getting off work at one of the city's many tech startups. But Rose (who wishes to be identified by the female name given to him by his first dominatrix) is in the right place. Alice welcomes him as he nervously explains that this will be his first time dressing up in public. She ushers him into the backroom, where he changes into a calf-length skirt, a brown-striped sweater, and a long black wig. He then sits at a table and begins doing his makeup. Annelise, a middle-aged man in an orange rubber go-go dress, swoops in to offer some application tips.

As the backroom slowly fills with sissies, I approach Rose and ask if we can chat. He agrees, though he requests that I conceal his identity. Rose is a heterosexual male, and the only individuals who know of his fetish are the women he's dated. I ask Rose to describe the experience of coming out to his recent girlfriend.

Lexi

"When I first dropped the bomb, it was very emotional. There was crying involved, mainly on her part," Rose recalls. "I told her, 'Listen, I cross-dress, and I don't want that to affect the actual relationship.'" Initially, his girlfriend was tolerant, but ultimately failed to give Rose the support he needed. "She wasn't the kind of person to go out [in public] with me. She was not actually my partner in crime as I had hoped. She was OK if I went by myself, but she wouldn't be next to me."

The relationship ended, and Rose is once again on the search for a "partner in crime," who will accept what he describes as an innate desire to experience bondage dressed in women's clothing.

"Growing up, I always had a bondage fetish," Rose says. "I remember playing cops and robbers games with girls. I think it materialized in the fact that I wanted to be the damsel in distress the whole time."

Rose's story is not uncommon within the world of BDSM. Many individuals in the BDSM community describe themselves as innately "kinky," often recognizing this aspect of their identity in childhood or teen years.

Alice in Bondage Land

Though Rose has had difficulty finding a romantic partner who is accepting of his lifestyle, some of the sissies here have long-term partners who embrace their fetish. I speak with Kendra, a San Francisco local who has been married to a woman for eight years. Kendra's wife not only accepts his fetish, she celebrates it.

"My wife is just awesome. Really open, really accepting—we both are—so there was no gray area around my cross-dressing," he says. "There wasn't really a coming out. When we would have kinky sex, it would be like, 'Hey, let's do this or that.' It organically happened. I wasn't like, 'I gotta tell you something very important: I cross-dress. Do you still love me?'"

Kendra, who also has three children, smiles warmly when speaking of his wife. He stands before me wearing fishnet stockings, a garter belt, and a spaghetti-strap crop top which shows off his chiseled abs and muscular arms. He shifts in his six-inch heels as I ask him if he is "out" among his co-workers.

"I am and I'm not," Kendra says. He explains that he works at Kink.com, the noted BDSM porn site. "Kink.com is a very 'accepting-of-everything' kind of place. I don't go around work in a dress. But I did get ready for Sissy Night at work, and blew the security guard a kiss."

Most sissies present don't have the option of blowing cross-dressed kisses to their co-workers. The backroom of Wicked Grounds is now crowded with men in various states of cross-dress, the majority of whom are extremely closeted. I speak with Lexi and April, two men who arrived together wearing matching Harajuku dresses with frilly Victorian petticoats. Lexi "writes software for robots," and April is a dentist. Neither are out in the workplace.

"I am only out to Lexi and another close, mutual friend of ours. I'm deep in the closet. This is my first time out in public dressed up," April says, beaming in Lexi's direction. "I'm really excited. I really have to thank Lexi for taking me out here. I wouldn't have been comfortable alone."

The two were friends for years, before discovering that they shared a mutual interest in Harajuku cross-dressing. "One day he accidentally showed me a picture [where he was wearing] a 'Lolita fashion' [Harajuku dress]. Then it was like, 'Oh, I'm into that, too,' and it started off from there," April recalls.

Though both describe a sexual interest in cross-dressing "role-play," neither are into bondage. "You see at lot of people focused on...humiliation. But you don't have to humiliate me to make me put on a dress," Lexi says. "I want to put on a dress. I want to find people who are into it, and not just as a humiliation thing."

Lexi's sexual interests may differ from many of the sissies here tonight, but he is still thrilled to be here. "[This night] is a different way of approaching cross-dressing. Before I used to just do it at home, by myself, in this purely sexual thing," Lexi says. "It's fun to push myself in the direction of trying to live in public a bit, and actually pass as female."

But though Lexi and April get a rush when they "pass" in public, neither identifies as trans. In general, this tends to be the case at Sissy Night. The majority of men I speak with say they are heterosexual, though some identify as bisexual or pansexual. There are also a small number of trans women.

Kendra

Dee identifies as both gender-fluid and trans. Dee is a Sissy Night regular, and a personal friend of Alice In Bondage Land. The two first met through FetLife, a social network for the BDSM community.

"When I first started interacting with Alice, it was because Alice had posted a picture on FetLife of someone she had duct-taped to a flagpole in the Castro," Dee recalls with a gleeful smile. "The duct tape was the pride flag colors...I thought it was a really neat idea."

The two became friends, and Dee expressed interest in staging a BDSM "scene" with Alice as the dominatrix, one that would ultimately help Dee embrace gender fluidity.

"The very first scene with Alice was a duct-tape bondage scene," Dee says. "We started by cocooning me with duct tape in a male mode. The end result was cutting me out into a female mode...I went from wearing a stereotypically masculine T-shirt and jeans to a skirt, frilly top, and little thigh-high faux-latex stockings. It was a complete shift. At that time, I was reasonably sure about the gender-fluidity, but this scene was the confirmation that this is actually completely accurate to who I am."

The ability to release gender-fluid butterflies from duct-tape cocoons is not a skill all dominatrixes share. That Alice was capable of such impactful gender fuckery, speaks to her uniquely queer perspective.

"I've been a part of the BDSM community for a long time, and we have a knack for both being accepting, but also splitting into factions," Alice says. "I don't want to be a part of the gate-keeping of gender. I'm not here to decide who does and doesn't deserve a label. I think coming together under a kind of scary term like 'sissy' is very triggering for some people, but also liberating in the same way that 'queer' is a triggering word. I'm trying to create a very queer space for gender, where it's not about what operations you're having, what hormones you're on...It's much more complicated than that, and it's very important to me that everyone is welcome here."

Alice's efforts have clearly been a success. It is now 10 PM, and the back room of Wicked Grounds is wall-to-wall sissies. Everyone is gearing up to head around the corner to a club called Bondage-A-Go-Go. Men apply last-minute lipstick, hike up their skirts, and shove "vanilla" masculine clothing into their work bags. The scene spills onto the street, as the sissy migration begins. I catch Alice before she leaves, and ask one lingering question.

"Why sissies? Out of the hundreds of fetishes to choose from, why specifically host a sissy night?" I ask.

"Because every boy I've ever fallen in love with has secretly worn panties," Alice responds, with a boisterous laugh.