Best Sex Writing of the Year

by Jon Pressick

  The stars did align recently, though. I’m seeing someone new, a wonderful cis girl I will call Kate. (Disclosure: even though I exclude identifying information, I asked her permission before writing this article, as it includes personal details of our sexy times.) In Kate I found a partner who not only thinks I’m sexy, but understands my body issues, and is willing to learn all the quirks involved in getting me off.

  Our first physical exploration involved cuddling. Cuddling is amazing with her. It usually takes a long time for me to warm up, but with her I get turned on almost immediately. Once I try to move beyond cuddling, however, I freeze. My first time with her, I was reluctant to take off my clothes. I was scared of rejection and felt mortified about my body. I also felt alone. Profoundly alone, in a way that’s hard to describe.

  Cisgender people have representation everywhere in the media. Images of them dating, making out, and getting dirty are on TV, movies, books, commercials, billboards, just about everywhere. Mainstream representation of women like me, on the other hand, is rare and usually follows a predictable script: cis man unwittingly goes out with trans woman, cis man finds out she’s trans (always in the form of a joke at the woman’s expense), cis man vomits and/or kills her.

  There is no romance for trans women in the media unless the plot involves a tragic ending. We are either a punch line or a Very Special Episode of “Blossom.” We can’t just fall in love, get in normal fights, have hot makeup sex, or any other romantic activity cis people take for granted. In mainstream porn, we are made into fantasy creatures that exist only to fulfill the taboo fantasies of cisgender straight men. There aren’t widely known cultural stories and dating norms that include trans women. We are always on the frontier, and while that can feel exhilarating, it’s also alienating.

  The first time Kate and I had sex, I was too nervous to orgasm. It wasn’t for lack of support, either. She was a caring, listening lover. She eagerly learned the ways I like being touched, and what to avoid so I don’t get dysphoric. Our second time together, as I reached the same impassable plateau, I asked her to stop, and lay there crying. Dysphoria and anti-trans baggage won out. I felt disgusting. She wished she could do something to help. We sat on the bed and chatted for a while. To pass the time, I showed her my strap-on harness and my porn DVDs. Trans Grrrls in particular caught her eye. As the night ended she reassured me, “You don’t have to apologize.” For anything: for my body issues, for crying, for feeling insecure.

  Kate and I fell headfirst into the infatuation phase of our relationship. The next day during work, she told me over Facebook that she was reading through my blog, because she just couldn’t get enough of me. That scared me, because I’ve written a lot about my dating frustrations as a trans woman, and the ways cis people have hurt me. Would she get offended by me talking about cis people in a negative light? Would she think I’m too angry? I was convinced she would find a reason somewhere in my blog to hate me. But she still made plans for our next date. This time, I was sleeping over.

  At her place we cuddled and immediately got turned on, like our previous times together. It was our third time together in the sheets, and my anxiety levels were increasing with each encounter. Surely, that night my transness would ruin everything. I was too broken and strange for anyone to love.

  “You wanted to watch one of my DVDs, right?” I asked. I’d brought several, but out came Trans Grrrls, the subject on the tip of both our tongues. We lay together, bodies wrapped around each other, and watched the opening scene with Chelsea Poe and Maxine Holloway.

  “That place looks familiar,” she said.

  “They filmed the opening part at the Dyke March last year.” We both lamented having missed the march.

  “It’s so hot that they’re actually doing it right there in public,” she said. I agreed, mostly by moaning, because at that point her hands were traveling all over me.

  Then the scene cut to an apartment, and Chelsea and Maxine tore off each other’s clothes. There on the screen was someone like me, having sex with someone like Kate. They were both happy, enthusiastic, and into each other. No “surprise reveal,” no horrified reaction shots, no cis gaze ruminating on how a trans partner might affect a cis person’s feelings about their sexual orientation. Just two women fucking.

  It made me feel human. And naked, even though my clothes were already off. A layer of psychic armor hardened by slurs, stereotypes, and violence melted off my body. It felt like the universe said to me, “We have a place for you. You belong here.”

  I said to Kate, “In a little bit you’re going to find out something

  I love about Maxine.” Maxine laughs when she comes, and it is so adorable. Kate agreed. Sometime after the second scene of the film, I had an amazing orgasm, all thanks to Kate. The isolation I felt during our previous encounters washed away. That orgasm was a revelation, a moment of healing, and I laughed like Maxine through the intense torrent of emotions. That was the first time I’ve ever laughed while coming instead of crying.

  I regret to say I had a hard time paying attention to the rest of the film. By the end of the night I was completely exhausted, in the best way possible. I didn’t think the evening would end with me lying in bed with her, catching my breath, but there we were.

  “I read in your blog that cis women scare you,” she said. Oh no. The exact words in my blog were, “Cis women scare the shit out of me.” Their bodies make me feel inferior, masculine, fake. Their mere presence can feel like it’s erasing my identity.

  “Yeah,” I said, hiding my face in her boobs like I’d suddenly forgotten object permanence.

  “Does that mean I scare you too?”

  “Sometimes.” I didn’t want to say it, but I wasn’t going to lie.

  She was supposed to get offended. Supposed to say, “We’re not ALL like that, you know! ” Supposed to dismiss my problems as whiny hypersensitivity, like countless people before her. Instead, she cooed and petted my hair. She said that hopefully she can be less scary. She kept holding me. She wouldn’t let go, and I didn’t want her to. I belonged there.

  In Defense of Celibacy

  Lauren Marie Fleming aka Queerie Bradshaw

  Celibacy is underrated.

  This statement may sound hypocritical coming from a person who makes her living writing about the antithesis of abstinence, but my life is often controlled by sex, so I understand the importance of taking time away from it and focusing on other things.

  Like learning to play bridge. Or crocheting. Or, you know, actually dealing with the fact that you watched your brother bleed out and die in front of you.

  Shit like that.

  There’s something to be said for taking sexual energy and aiming it somewhere else. Queen Elizabeth, Joan of Arc, Florence Nightingale, these women put their sexual frustration to good use. I’m not looking to run a country or fight a holy war, but I bet I’d finally finish my memoir about sex if I quit spending so much time having it.

  Monks and priests have been known to levitate, survive being set on fire, and heal the dying. Give up sex and all that extra energy can go into performing unbelievable feats. Just last week, instead of going on the two dates I had planned, I cleaned my whole apartment, washed every article of clothing I owned and neatly organized my extensive sex toy collection: a bona fide miracle.

  Like most lesbians, I’ve dabbled in hippy, new-age, touchy-feely emotional exploration, but as much as I love a good drum circle beating out Ani DiFranco’s greatest hits, I’m more of the in a dungeon beating on a stranger type.

  Or I was.

  Now I don’t really know who I am and what I want. Two years ago this week, my sister and her baby came horribly close to dying during premature labor. A month later, my brother was diagnosed with cancer. A month after that, my grandmother had a stroke at my law school graduation. Ten days later, I watched her die. About once a month after that, my brother had some tumor removed from or poison put into his body. Then he had his jaw removed. Then a month la
ter, I watched him die.

  After that, all I wanted to do was get drunk, fuck, and shoot guns, so that is what I did.

  Then my grandfather, Poppo, one of the most important people in my life, a man who shared my birthday and taught me to paint, died. For the last week of his life, I helped feed him morphine, sang him songs and held his hand, watching the light slowly fade from his loving eyes.

  Soon, we were planning yet another funeral, the third for my family in eighteen months and nothing could be said or done to make me feel better. Including sex. Instead, the thing I love to do most in the world has become a chore, yet another emotionally painful thing to endure.

  The vulnerability that having sex caused in me was destroying me and I was destroying any chance of a solid, healthy relationship with someone in return.

  It was time to be consciously celibate, to take sex, and the horrible insecurities it now caused in me, out of the equation.

  This realization scared me. We live in a sex-dominated culture and I make my living being right there in the heart of it, experiencing every bit I can and sharing my findings. I’ve engaged in a plethora of pleasure for the sake of a good story. I go for the risqué and raunchy because it gives good headline.

  It’s hard to purposely give that up, but give it up I am, until June 6, the day my completed memoir is due.

  I’m still going to attend all the porn conventions, sex worker get-togethers, BDSM play parties, dominatrix gang bangs and tantric workshops I have planned between now and June 6, I’m just not going to be quite as participatory.

  I almost didn’t say anything to anyone, but then Jenn, an amazing radical, fat, femme blogger colleague of mine reminded me that, “Intentionally not engaging in partnered sex is political and complicated and worth talking about.”

  So here I am, a kinky queer sex writer, making a statement by not having sex.

  I’m not quite sure what that statement’s going to look like yet; first I have to figure out what exactly I’m giving up, what celibacy means to me. One of my closest friends gives up sex all the time, taking vows of celibacy from hours to months depending on what he’s looking to accomplish in his life at that moment. His celibacy attempts to delete all sexual thoughts from his mind and therefore masturbating is not allowed.

  When he asked me if I would do the same, I replied, “I’m a not a fuckin’ saint here.” However, as I think about it, if finishing my memoir and writing more is one of my goals, I may have to give up masturbating as well. I spend (sometimes waste) a big portion of my days reviewing sex toys and porn over and over again, you know, for work. If I gave that up, or limited it at least, I’d have a lot more time to work on projects that pay my bills.

  But who am I kidding, I’m not Joan of Arc. I haven’t gone a week without masturbating since I discovered the joy of a vibrating toy at age six. Masturbation is staying on the table.

  Romantic dates, however, are off the table. Way too time consuming, trying to get to know someone new. If I want dinner, I have to call a friend. Penetration is obviously off, including any oral sex, but I’m going to play kissing, cuddling and nonsexual BDSM interactions by ear.

  I feel like I’m missing something, but all I can think about is fisting.

  This may be more difficult than anticipated.

  I once took a vow of celibacy for two months after a bad split from a long-term relationship. About two weeks into it, I was heading to go break that vow when I broke my foot and ankle instead.

  I don’t believe in a vengeful God judging from above, but I still feel like he was punishing me for my sins that night, angry at me for attempting to break my promise to myself. If thinking about having sex caused a cast, I’m worried about ending in full-body traction if I fuck up this new vow.

  It always seems like the minute I decide to stop looking for sex, sex comes looking for me. I’ve had three offers in the two days since I made the decision to take a break from sex, all from people I really want inside of me. I’m currently writing this sitting at a house on the beach in a bikini next to a hot butch, who is testing my resolve by looking quite dapper in an outfit set for captaining our invisible yacht.

  It’s harder than it sounds, to not have sex. To not reach over, grab his hand and lead him to the back room, or better yet wait a few hours until it’s dark and lead us to the shoreline, waves crashing our bodies together.

  When your brain is constantly an erotica novel, it’s really hard to not act out these fantasies.

  Sure, the butch and I are just here as friends, simply enjoying a sunny San Diego day together, but I know how good he feels against me, I know exactly what I’m missing out on.

  Unfortunately, that includes emotional instability right now as well. I haven’t felt this way about someone in a very long time, but I changed that moment I saw my brother die and now I have no idea what I want from sex or a relationship, making navigating both impossible.

  Once I gave up sex with the person I was seeing (and liked) the most, it was surprisingly easy to give up the others, sending them back into friend zones, explaining to them that I’m just not there right now, that too many funerals have left me with no energy for sex, no ability to be vulnerable in yet another way. It was shockingly simple.

  At first.

  Now I want to hump everything that moves, rotates or vibrates in any way. If I’m going to be serious about this temporary break from sex, I’m going to need help, so naturally I turned to Twitter and Facebook for advice. Soon my inbox was flooded with stories from my amazing followers of what they did, learned and changed through consciously and purposely abstaining from sex.

  I started with the stories from people who, like me, quit having sex because their grief was too overwhelming. A woman who first met me through my online dating profile explained why she quit having sex after her father and friend died close together:

  “I didn’t feel inclined to share any part of me with any other person...I’d worked so hard to put all of my pieces back together, and I was afraid that if I let anybody in, they’d just shake those pieces loose and I’d be a crumbling mess again. My abstinence acted as my mortar for a strong foundation.”

  The theme of building a solid emotional foundation through abstaining from sex was present in almost every story I read. In a society with an arguably unhealthy obsession for quick pleasure, it’s not surprising people would feel a need to give up sex to feel emotionally stable, fulfilled even.

  There are times in your life when a quick fuck can be beneficial, but sometimes all sex does is add to the confusion that is life. Sex with others muddies the emotional waters; take sex away and there’s a better chance of finding clarity within yourself.

  “I spent approximately four years without having sex during my mid-20s. At the time I was sure I shouldn’t be dating vanilla girls, and I did explore the possibility that I am gay because of my cross-dressing and pegging desires. It took me a while to both realize and accept that I am a sissy who needs a naturally dominant female, and those years of not having sex helped me by avoiding further confusion of trying to be something I’m not with the wrong women.

  Once I realized what I needed, I sought it, found it, and am happier than I’ve ever been.... I attribute much of this to those years I had to discover myself.”

  This story from a Twitter follower of mine reminded me that I’m not new to the act of abstaining. After bad and boring sex with men in high school, I didn’t have sex for three years. I had absolutely no interest in it, which was sad and shocking to me at the time, until I had sex with a woman and WHOA, there’s what I was missing.

  Counting up all the periods of abstaining from sex, both consciously and consequentially, one-third of my sexual life has been marked by a lack of the act. Looking back, those were the most productive years of my life. They were also the most lonely ones as well. There has to be a balance, but I’ve yet to find it, and when faced with sex or sleep, I choose the latter, which is why I’m single but my skin is fabulous.r />
  One thing I’ve learned is that there’s a detox period and it gets easier with time. It’s not that you forget what you’re missing, you just learn to live without it consuming you. I’m not alone in this feeling. A Twitter follower of mine wrote:

  “If I’ve learned anything from not being active for a while it’s that sex just really isn’t that important to me in the long run, especially if I’m not dating anyone. I have a friend who dates regularly and has a rolodex of partners to choose from. She has an active sex life and is used to it. She recently visited her parents for a week and upon her return she was almost frantic from not having any while she was gone.... I enjoy sex and all, but I’ve never understood the physical craving for it that (I suppose) comes from engaging in it regularly.”

  I understand that craving all too well. I’ve understood that craving since I was six. I explore that craving religiously, both personally and professionally.

  I’ve never been one for religions with puritanical teachings, never thought of pleasure as a bad thing, but I’m learning to respect religious people who abstain for their own emotional and physical benefit.

  Jenny, a blogger buddy of mine, wrote to me about her choice to find herself and God during her self-induced abstinence period:

  “It was hard at first…but when I got accustomed to it, there was actually a lot of freedom in it. When I met a guy at an event, through a mutual friend, or at church, there was never that thought of ‘what will he think of me?’ and a tendency to perform as there had been in the past.”

  Maybe that’s what it is, maybe I’m just tired of performing, pretending I’m okay when I’m really not, feeling especially like I have to be okay with sex, the thing in which I am a supposed expert. The question “How are you doing?” is impossible for me to honestly answer these days because I have no clue how I am doing; I haven’t even begun to figure that out.

  As much as I wish sex were the answer, it’s becoming glaringly apparent that it’s not. It helped at first, letting my grief give way to pleasure, shutting off and shutting out, but eventually I imploded on myself and now I’m even messier than before.