Best Sex Writing 2013: The State of Today's Sexual Culture (11 page)

“I do?”

Rachael said, “If this is the highway to hell, I’m not riding it alone.”

I tried to think of a reason not to. A good reason wouldn’t be good enough. Not here. Especially not here.

Tweaked snapped on the lighter and maneuvered the pale blue flame under the crystal. It melted and was transformed from powder into a white haze.

“Draw,” he said. “Not too hard.”

I touched my lips to the tip of the warm glass, inhaled and watched the smoke disappear until it emerged again as a frail,

white wisp. There was only the slightest chemically tinged af- tertaste. A wave spread through me, euphoric, but much more. There was clarity—perfect, doubt-obliterating clarity.

From outside, Mandy’s voice spiraled up, signaling her or- gasm. I looked up to the ceiling. The image there was as plain as it was unambiguous: it was me and Rachael, sharing the first car on our fantasy roller coaster—a ride with no rules or limits, our arms held over our heads as it came right off the rails.

Rachael came up to me. She placed her arm on my shoulder. “You okay?”

I took a deep breath. “I think it’s time to go back.” “Back?” said Chipper. “You can’t go back. Not now.”

Chipper was right. Rachael and I returned home, where our sleep-and-food-deprived bodies finally teamed up with our rav- aged nervous systems and our bruised egos to let us have it, right in the old cerebellum. The whole damn country seemed to join us in a spectacular crash, as markets collapsed and planes smashed into buildings. Some of our friends ended up sick, others in rehab. It had been one hell of a party, but the party was over.

And so were Rachael and I. After Fire Island, a black shroud descended over us. We burrowed down into a grinding disil- lusionment and mutual resentment from which our relationship never really recovered. There was an affair—mine—followed by divorce.

“More is more,” Rachael used to say. Maybe so. But on Fire Island I learned that, sometimes, more is just too much.

Cherry Picking

J ulia Ser ano

The first time I learned about sex was in fifth grade. It wasn’t by way of a sex education class or a Mom and Dad birds-and-the- bees speech, but rather a joke. A completely unfunny dirty joke little kids tell to pass along important information. I think the punch line was, “Mommy, Mommy, turn on your headlights! Daddy’s snake is about to go into your cave!” Now, granted be- fore hearing the joke I already had a strange relationship with my penis. I used to draw pictures of myself naked with a needle going into my penis, imagining that it contained special medicine that would make the thing disappear. Every time I used the urinal in the little boy’s room, I had a sneaking suspicion something wasn’t quite right. That night, after hearing the joke, I remember looking down at my penis, knowing what it was supposedly for, and I felt absolutely detached and dumbfounded.

The first time I dressed as a girl was in sixth grade. I had

insomnia and one night I felt compelled to wrap a pair of white lacy curtains around my body. I stared at my reflection in the bedroom mirror for hours. I looked like a girl. Perhaps it should have been no surprise. I was prepubescent and had one of those longish, late ’70s, boy haircuts. But it completely blew my mind. The scariest part about this revelation was that it somehow made perfect sense.

The first time I had a crush on someone was in seventh grade. Her name was Kathy and I thought she was cute. Nancy Phillips told me that Kathy liked me but I was too chickenshit to ask her out. So I fantasized about her instead. I imagined some bad guy had captured us both and as part of his evil scheme he would offer me two choices: he would either kill Kathy or turn me into a girl. He left it up to me to decide and I would always gallantly choose the latter. Kathy would be so impressed that I had sacrificed my maleness to save her life that she would ask me out on a date. I always said yes, and the rest of the fantasy involved different permutations of the two of us sucking face. All of this happened before I ever heard the word
lesbian.

The first time I decided to change my sex was in tenth grade. It happened at my baseball league all-star game. I wasn’t playing in the game but I went with a few friends who also didn’t make the team. While we were sitting in the bleachers, a group of neighborhood girls walked by and some of my flirtier guy friends started teasing them in that teenage-boy “I like you” sort of way. Both groups struck up a conversation but I just sort of sat there and stared. It seemed so obvious to me that I should be one of those girls rather than one of these boys. It was so sad because nobody could see it but me. So I decided to get a sex-change operation. I didn’t really know what it was or what it involved; I had only heard about it on TV. Later I realized if I was to pursue

such a thing I would have to let all of my friends and family know I wanted to be a girl, and I couldn’t think of anything more frightening. So, instead, I tucked the memory of my all-star game epiphany into the dark recesses of my brain. Like a time capsule, it wouldn’t surface again for another fifteen years.

The first time I had a girlfriend was in twelfth grade. She was smart and quirky and interesting and cute and completely kick- ass. I totally fell for her; she was my first true love. After dates, we would park on a quiet, dark street and make out. Her lips were the first ones I ever kissed, her breasts the first I felt up, her vagina the first I fingered. She was one year younger than me but way more mature. When I left to go to college, she suggested we see other people. I was devastated but she said that we were both still really young and had our whole lives ahead of us. She was right.

My first supposed sexual peak came when I was eighteen. It was my first year of college and I didn’t really have any freshman sexual experiences to speak of. Some years are just like that but don’t feel bad for me, I made up for it by having a second sexual peak as a woman at the age of thirty-five.

The first time that I masturbated to orgasm was when I was nineteen. Nobody ever believes that it happened so late but it’s true. Before then, when I’d play with myself, I would push down on my penis and rock my hand back and forth. I’ve been told that that’s how a lot of girls do it. I just did it that way instinctu- ally. It felt really good, but I never orgasmed. Then my college girlfriend gave me my first hand job and I learned the power of the stroke. Granted, I knew about the stroke from watching porn but it never occurred to me to try it out on myself. It worked like a charm. It’s amazing how you can have a body all of your life yet there’s always something new that you can learn about it. Strangely enough, I don’t really remember the first time that I had

penetrative sex, the supposedly landmark day when my virginity was officially lost. It’s true. I know it happened when I was nine- teen with the girlfriend I had throughout most of college. I’ve lost the particular night we popped each other’s cherries in a blur of dorm-room sex scenes the two of us shared over a three-year period. Eventually she went on the pill, and since we were each other’s first, we stopped using condoms. I could never get over how amazing it felt to be inside her, to feel my genitals inside her genitals. To this day, the feeling is the only part about being physically male that I fondly reminisce about.

The first time that I ever went out in public dressed as a woman was when I was twenty-one. I came home from college for Easter weekend while the rest of my family was away on a trip. I shaved off the silly-looking beard I had grown over the semester. I put on my sister’s black cotton knit dress. It had long sleeves so no one could see my arm hair and I wore opaque tights to hide my leg hair. I’m sure I put way too much makeup on my face and way too much product in my hair but nobody seemed to care because it was the ’80s. I drove to a mall about an hour away from my parents’ house so I wouldn’t run into anyone who knew me. As I approached the entrance, an older man held the door open for me and called me “sweetie,” and I felt flattered and insulted at the same time but mostly I was just amazed to be getting away with it. After walking around the mall for about ten minutes, I real- ized I was hungry and hadn’t eaten all morning so I drove to a Burger King for a shake and fries. The woman at the drive-thru window said, “Thank you, ma’am,” as she handed me my change and receipt. I can’t begin to tell you how beautiful those three simple words sounded.

The first time I told someone that I cross-dressed was when I was twenty-three. He was a friend of a friend and we were

hanging out at a party. Out of the blue, he told me he was bisexual and he thought I was cute. I told him that I wasn’t into boys but I did like dressing up as a girl. We talked about it all for a couple of hours. When I woke up the following morning, I practically died of embarrassment.

The first time I kissed a boy was when I was twenty-four. It happened in the Bronx. I was coming to terms with my submis- sive fantasies and met a dominant guy through a personal ad he had placed in the
Village Voice
. In my fantasies I was always female but I was afraid to go to his place cross-dressed, so instead I went in drab (tranny talk for “dressed as a boy”). When I got there, he was dressed head-to-toe in leather and reeked of patchouli. His stereo was blasting Depeche Mode, which seemed really cliché. He tied me to his bed, blindfolded me and began kissing and groping me. It was extra-weird because he had a moustache and I kept imagining that his mouth was some strange combination of a porcupine and a leech. It wasn’t a lot of fun. I’m sure he didn’t enjoy himself much either, what with me being a confused and inexperienced bottom who just sort of lay there doing nothing. Afterward, we both talked about our favorite Woody Allen films. I never saw him again.

The first time I had sex with someone while in femme mode was when I was twenty-eight. She was a bisexual friend who I dated on and off for a bit. First we went to the SF MoMA to see a Frida Kahlo exhibit. Then we went back to her place and shared a bottle of wine. We kissed. She fondled my foam breast through my shirt and told me how much she missed being with a woman. She lent me some clothes that were less dorky than the ones I had on, and she took it upon herself to redo my makeup and hair. She made me look way better than I did earlier that day. We left her house to go to the Chameleon, a local dive bar. She laughed when

the Latino boys in her neighborhood made the snake sounds at me. We had a few beers and talked.

It was like two girls talking, she even said so. We both cried at one point. I’m not exactly sure why but in retrospect I think it was because we both realized how sad it was that I had to keep this part of me hidden most of the time. Afterward we went back to her place and had sloppy sex. She wanted me to penetrate her but I couldn’t keep it up. How could I after all of that? The next morning, I woke up and realized I didn’t bring any boy clothes along because I wasn’t planning on spending the night. She lent me a pair of her pants and a hockey jersey to wear on the return trip to my apartment. She was a lot bigger than me so when I put on the shirt it felt like I was wearing a tent. I seemed so small. I can’t remember ever feeling less like a boy than I did sitting on the BART train wearing that hockey jersey.

I met Dani, who would eventually become my wife, when I was thirty. We shared lots of firsts together. She was the first dyke activist that I ever dated, the first person I ever moved in with, the first person I shared a checking account with. We even merged our CD collections. She was the first person to take me with a strap-on dildo, the first to give me a purely anal orgasm, the first person who truly understood how to make love to my physically male body while relating to me as a woman. Dani was by my side the day I first called myself “queer” and the day I first dared to refer to myself as “transgendered.” She was the first and only person I ever asked to marry me. On a rainy night, during the brief period when we were calling each other “fiancée,” the two of us were lying in our bed. I told her I was thinking about transitioning. We held hands and talked about it through the night. In the morning she took me out to breakfast by Lake Merritt. She made me laugh. Somehow she made the scariest day of my life really, really beautiful.

The first time I took female hormones was when I was thirty- three. It was the day after our honeymoon. I washed the pills down with water, then sat on the balcony of our apartment waiting for the buzz to hit.

The first time I had a female orgasm was about two months after that. I was masturbating, and for the first time in my life the stroke just wasn’t doing it. I just needed…more. So I grabbed Dani’s Hitachi Magic Wand. A few years back I had tried out her vibrators but they were way too much stimulation for my male orgasm. But now, after two months of being on female hormones, I could place her vibrator directly onto the tip of my penis and… wow! Suddenly I found myself writhing for ten or fifteen minutes straight, in a sexual state at least twenty times more intense than any boy orgasm I had ever had. I decided right there and then I was never going back.

The first day I lived as a woman was a day that Dani and I had planned to celebrate. On our honeymoon, she bought an expen- sive bottle of wine for us to share on that special occasion. How- ever, some firsts don’t happen in a very clear-cut fashion. There was no first day of being female for me. Instead, I just gradually changed over a five-month period and before I knew it, strangers were referring to me as “she” even though I was still dressing in drab. We ended up drinking that bottle of wine on our wedding anniversary instead.

Some people have asked if I will become a virgin again when I eventually have bottom surgery. You know, a vaginal virgin of sorts. I just laugh. The whole idea of virginity is utterly ridiculous, as if every person’s life can be divided up neatly into an innocent childlike half and the impure adult half. People who believe this must have excruciatingly boring and simplistic sex lives.

For me, there have been many first times and each has given

me a rare opportunity to see myself a bit differently. My life has no singular defining point because each first time is dependent upon all of the other ones that came previously. And while having surgery may mark the end of my physical transition to female, I don’t see my sexual evolution as reaching some sort of conclusion. If there is one thing I’ve learned, it’s that there will always be more first times to look forward to in my future.