Lady Cheeky’s Sex Satori


Tweet sex sites are a many splendored thing, opening doors to fluid identities that are both sexy and risk-free while erecting an emotional firewall to avoid real, personal rejection. My hackles go up whenever I think about technology replacing human touch, but when I met Lady Cheeky and heard her story of seeking and finding passion via tweet sex, I witnessed a brave new world where one woman’s sexuality was accessed in an accelerated way that involved wooing, teasing, and palpable passion.

“Lady Cheeky” is her Anglophile cybersex identity name, where she is a servant/vessel/wench. We met on the floor at Marilyn Friedman’s essay writing workshop, which I signed up for during a dark time. After dozens of agent rejections flooded my inbox for over a year, I longed to sit in a room with other writers again, hoping to inject my writing with joy by learning new literary tricks from veteran journalist, Taffy Brodesser-Akner. Our assignment was to tell the group what our essay was about and then say one more line declaring what our essay was “really” about.

Lady Cheeky’s wavy, Lucille Ball hair matched her bright red lips. Her curves punched out of her ’40s frock, as she told a hilarious topsy-turvy tale about role-playing on a True Blood-themed, Twitter-based direct message and tweet stream, which led her to start her smart and sexy websites where she met “Lord Byron,” hired a P.I. to check another lover out, and divorced her husband. She also overcame a rare sexual disorder; started a popular sensual images blog; began writing and publishing real-life erotica based on her new, passion-filled experiences; is in the process of working on a memoir; has a new story in Rachel Kramer Bussel’s upcoming erotica anthology, The Big Book of Orgasm; and is currently speaking about body image and sensuality, as well as integrative sensuality.

Lady Cheeky’s story beneath the story was flesh and bone ache deriving from a phantom limb that was pummeled awake by HBO’s True Blood series. I wanted to know more about how True Blood was the springboard to becoming a sexually actualized woman, capable and deserving of passion.


The Rumpus: You talked about feeling misplaced from the get-go. Tell me where you grew up and your first sexual experience and how you felt so “other.”

Lady Cheeky: I was a white Jewish girl with a dry sense of humor who grew up in Santa Monica. I went to school with tan, athletic surfers and never felt like I fit in. I discovered my sense of humor helped me get by. I was reading all of my mom’s Fran Leibowitz books at the time, so I had adopted her New York-centric, ascerbic wit, which didn’t help matters in the “socialization with my peers department.” I was living with my sister and my mother in a tiny apartment. My mom was a funny, tiny, New Age-y performer trying to raise two girls after a divorce. She left my father and moved us out to California when I was six.

Rumpus: You mentioned that you had a rare sexual disorder. Tell me about it and how you overcame it:

Lady Cheeky: I had been diagnosed with vaginismus when I was about twenty. Victims of rape and molestation experience this, but I was not a victim of sexual assault. It’s characterized by the muscles in your vagina constricting and tightening up upon impending sexual intercourse so nothing can penetrate. It’s very painful to try and have sex with vaginismus. I was able to lose my virginity without incident, but after that I tried countless times to have sex and it was just a disaster. After that, if I was ever able to, it was because I got drunk beforehand. Not how you want to experience sexual pleasure all the time.

Before I met my husband at age thirty-two, I had only had intercourse a total of five times. I went to therapy for it and eventually was able to have sex successfully, but even so, it was not enjoyable. No one ever talked to me about sex as a kid, and the men I was with never took the time to ask me or help me discover what I liked.

Rumpus: When did you realize you lacked passion in your life? How did True Blood lead you into a world of passion?

Lady Cheeky 2Lady Cheeky: I always wanted to try different sexual things with my husband, who adored me, but it didn’t fly. I knew sex was supposed to be enjoyable and I wanted that to be a part of our life, but my husband was just not that into it. Eventually, I fell into a deep depression and could not get up or eat, and couldn’t figure out why. It seems I was only unhappy with myself, but was also realizing I wasn’t in love with my husband. He had some emotional problems and felt more like my pet. I felt like his mother, not his wife. I was on medication, but no “cocktail” seemed to help. I look back now and see I was on the verge of a nervous breakdown.

Then a friend called me to tell me to watch True Blood. “It’s really dark, sexy, and campy,” she said. “You’ll love it.” When I finally watched it, I felt the chemistry on screen. It was revelatory. I knew that this was something I had never experienced. I thought, “I’m forty years old and I don’t know what it’s like to know passion.” I wanted to be a part of something passionate.

Rumpus: What did becoming a tertiary character on True Blood’s role-playing site involve?

Lady Cheeky: I became unnaturally obsessed with True Blood, freakishly so, almost like a thirteen-year-old girl, and devoured anything I could find on it online. I came across people tweeting about True Blood and so I joined Twitter and started tweeting back. Not only were they tweeting about True Blood, they were role-playing. There were all of these different casts and some new characters with different names, and they were throwing virtual weddings and True Blood parties. So I created tertiary characters so I could play along, like Bill’s Pet and Bill’s Robe. People flirted and eventually asked to have cybersex with me as my character.

At first I was shocked, and then admittedly intrigued. I wanted to flirt [and] feel sexy. I’d never felt sexy before. This seemed like a safe way to do it.  Then I decided to branch out into my other areas of interest. Always an Anglophile, I found this other set of nerds like me where I played the handmaiden to Ann Boelyn (one of Henry VIII’s wives, whom he beheaded) and became “Lady Cheeky.” For the first time, my sexual self felt free. Meaning, I could move around and play. I could be sassy and say things like, “Why aren’t you undressing me right now?”

Rumpus: Did you ever get rejected on the sites? Tell me about one uncomfortable experience you have had while exploring this world.

Lady Cheeky: When you get rejected in cyberspace, it has nothing to do with who you are or how you look, so it’s “safe in that way.” You are a fake person. Completely free. I was flirting with a sarcastic, angry, funny “knight” one day, and we set up a phone sex date. Well, I was so excited, I left work early and when I called him he said, “I can’t right now. My mom’s home.” He was nineteen. I thought, Who am I? What the hell am I doing? But, I also felt alive for the first time.

The most uncomfortable yet freeing thing was when I became involved with a man I met on Twitter who called himself “Guerre.” He was a hopeless romantic, passionate…and married. I knew I shouldn’t be seeing a married man, but I was completely infatuated with him. After a few months of e-mails and instant messaging, we decided to meet, but before that, I hired a P.I. to check him out. I needed to know he wasn’t wanted in forty-nine states or otherwise had a record.

Rumpus: Is that when you asked for a divorce?

Lady Cheeky: No. I had already moved into our guest room and told my husband I wanted to separate. I knew I wanted a divorce, but thought the idea of a separation would be a smaller pill for him to swallow at first. He wanted couples therapy, which I agreed to for his piece of mind. In couples therapy, I asked for the divorce. I moved out shortly thereafter. I didn’t meet  “Guerre” until I had moved out.

Rumpus: Did that affair pan out? Where did your passion take you?

Lady Cheeky: When I met “Guerre” in person after three months of online courtship, our spark was immediate. Before we even touched we knew it was going to be incendiary. I felt something in my body that I had never felt before…a buzz…a tingle…hard to explain. It was intoxicating. I had struggled with body image issues and of course never, ever actually enjoyed sex, but now, with this man, I knew all that would be water under the bridge, and I was right.

What that night (and our subsequent ill-fated affair) taught me, was that passion is a life force from which so many positive parts of ourselves are able to flow. I discovered that “sexy” is something you are—not something manufactured. It resides in all of us. It’s as much a part of us as the shape of our face or our hair color. In that way, we can cover it up, manipulate it to a desired shape or ignore it completely…but it’s there whether we choose to see it or access it or not. This “satori” gave me a new paradigm in which to see myself and a confidence in not only how I approach my life, but how I approach dating and sex.

Rumpus: Why do you think people are so sexually repressed and afraid to explore sex and passion? Why are people so ashamed of their desires? How did you break those constraints?

Lady Cheeky 3Lady Cheeky: In my opinion, we are in an age (and hopefully coming out of it) where our personal sexual pleasure is somehow looked at as, at best, something polite people don’t talk about and at worst it’s looked at as deviant. This creates an atmosphere of shame and denial of a basic human need. This is especially sad today, in a world where most people have to work, scrounge and save to get any pleasure at all.

I had a male friend who said to me recently that he hadn’t come in three weeks. He said he didn’t deserve it. Who in the world doesn’t “deserve” to come? It opened my eyes to the fact that our human right to have desire, passion, and sexual gratification is something no one wants to talk about. We can read articles about women who have never had an orgasm all day long, but the bigger problem is that there is obviously a population of women and men who haven’t allowed themselves to experience sexual pleasure as a part of life, and lots of journalists are writing about just the mechanics of it. This is a big enough problem; it seems it sells magazines.

Rumpus: You are a writer and sex-positive blogger. You told me about the app of the week, a video program called Vine where you can send a six-second video that self-destructs, but I haven’t tried it yet. At the same time, you were nearly in tears when you talked about your friend comparing you to Melissa McCarthy and you wrote a beautiful essay about that. What is the connection between your self-image and your sexuality?

Lady Cheeky: Your body has nothing to do with how sexy you feel. In the trope of curvy women, I still get hurt and it’s hard. The feeling I have of being a sexual person is inherent. For better or for worse, no one can take that away from us. How we feel about our physical selves is linked to what society and advertising tells us is normal or acceptable, but it’s ultimately our responsibility to take our self-image back and reclaim it, as it were. I could be working on my self-image, still be self-conscious, still not want my lover to touch my stomach, and still tap into my inherent sexiness, because, as I said before, sexy is who we are. I had this realization when I felt bad about myself and looked in the mirror recently. I said to myself, “This is how I came out today. I’m cooked.” Then I click into my sexuality and I feel good. At some point you’ve got to give it up: This shirt is going to hike up my hips. Done. Let it. I’m going out.


Featured image of Lady Cheeky © by Gene Reed.

Antonia Crane is a performer, 2-time Moth Story Slam Winner and writing instructor in Los Angeles. She has written for the New York Times, The Believer, The Toast, Playboy, Cosmopolitan,, The Rumpus, Electric Literature, DAME, the Los Angeles Review, Quartz: The Atlantic Media,, Buzzfeed, and dozens of other places. Her screenplay “The Lusty” (co-written by Transparent director, writer Silas Howard), based on the true story of the exotic dancer’s labor union, is a recipient of the 2015 San Francisco Film Society/Kenneth Rainin Foundation Grant in screenwriting. She is at work on an essay collection and a feature film. More from this author →