These dates were always after dark, very covert, in the shadows, in hotel rooms. It was all about quick sex, especially me fucking them up the ass. Sometimes I used my Colt ten-inch dildo when I couldn’t get it up. With some guys my arm got tired from all the anal ring toss they wanted to play. Some guys just wanted to sit around and jerk off to dull she-male porn. Initially I found it amusing that so many guys wanted to do nothing but lick my boots or have me breastfeed them, but there was no give and take, just a lot of giving on my part. It got to be boring. Sometimes I just wanted to go out to dinner. Sometimes I just wanted to lie on my back and be fucked.
Sometimes, of course, a guy would venture out in public with me and guys like these would get a big turn-on from taking me out to dinner because nobody else knew he was out with a transgender woman. “Isn’t this exciting! No one knows you’re a tranny,” I remember one guy telling me, with clam sauce around his chin, my hand covertly jacking him off under the table of a posh restaurant. The next time this guy took me out to dinner, the restaurant was packed. We had to wait for a table, so I gave the hostess our name for the wait list. A few minutes later the hostess called out, “Transsexual party of two, your table is ready. Transsexuals, your table is ready.” My date bounded out the door like he was escaping a house on fire. I applied some lip gloss and told myself I was done with those kind of guys. I craved more pampering.
Around the same time, I would also meet women, and I found my escapades with queer women more satisfying. These encounters usually happened after I played a show with my band and there would be dyke stage-door johnnies wanting to hook up. They usually gave their real names—but this being San Francisco, real names meant Tiger and Wind Chime. There was a lot less ass play and sometimes we even ventured forth in daylight hours or took road trips. I remember fondly the butch lesbian who took me to Portland and pumped me full of crystal meth and beer and asked me to go-go dance for hours to her Ferron cassette. Eventually the crystal wore off and we cuddled the remainder of the weekend.
The other demographic I’d have hook-ups with would be straight swinger couples. I found myself in a lot of Pacific Heights homes, where usually the wives thought it would be fun if I fucked their husbands up the ass. As I got behind these guys’ backsides, they would shriek things like, “I’m a bitch! I’m a bitch! I’m a bitch!” As I pumped away, I found myself distracted, wondering to myself, How on Earth did heterosexuals take over the world? These encounters were so boring I did very few of them. I’d usually leave with cab fare and a very expensive bottle of wine.
I finally got tired of the fetishized objectifying. It wasn’t gratifying. I wanted a legitimate relationship with someone who had clean hygiene and would treat me right. I realized I wanted a real relationship but felt a sense of futility that I’d ever find one. I took a couple years off from dating anyone, to sort out my head. One thing I knew for sure: I was done with cisgendered men and women.
There were two pivotal events in the formation of my adult self. As a child my family moved around a lot and I had to change schools frequently. No matter which part of the country I ended up in, I found myself perceived to be the class faggot by my classmates. When I lived in a small town in North Carolina, one boy in particular bullied me nonstop. His name was Armitage Rufus Peppington. Armitage devoted his days at our school to making my life unpleasant, filling me with fear and terror. To make matters worse, come summertime, my parents forced me to go to Jesus Camp and I had to share a tent with this lout! After three days of torment I’d had enough and devised a plan. After Armitage fell asleep, I pulled some Nair out of my backpack (I never traveled without it) and very carefully applied it to his eyebrows. Hours later, when he woke up looking like a surprised extraterrestrial and cried like a baby, I realized I loved to dominate boys.
As a teenager growing up in my Christian household, I knew I was trans, but the feelings were very uncomfortable. I had a lot of shame. I thought if I got a girlfriend, maybe I’d be cured of these sinful feelings. I prayed to Jesus to give me a girlfriend, to make me “normal.” My prayers were answered shortly afterward, in tenth grade, with the appearance of Blaine in my life. Blaine was on the high school softball and soccer teams. We got along great.
After dating about a month, I was invited to meet her mother. I was shocked when both of them said I would make a better girl. That was confusing, and I wondered if Blaine would keep dating me. But then we began having lots of sex at motels, where we’d register under names like Mrs. Abraham Lincoln and Blaine insisted on dressing me up in girls’ clothes and putting makeup on me. “You’re real pretty,” she’d say, then fuck my brains out. So much for Jesus making me normal. Or maybe Jesus was answering my prayers. At school the next day I didn’t know if I felt like a dirty schoolboy or a dirty schoolgirl. But it had to be secret. I was a secret.
These were the two formative conditions of my burgeoning self. I was discovering I was a naughty girl who liked to dress up and teach boys good manners. If only I could find someone who didn’t only want to do this clandestinely.
When I met Canadian Slim that all changed. I was at Café Du Nord, a nightclub in San Francisco. I had played a show earlier and now was at the bar. I saw him come out of the night and down the steps into the bar, illuminated in light. He was a tall handsome trans-guy who I later learned was from Vancouver. He saw me and kinda blushed, which I found very cute. We began talking and an hour later I was in his room pulling his cock out of his denim.
I began to work his cock with spit, tugging and then sucking him. He came right away, shuddering a little. Then he grabbed me hard by my hair and pulled me up. He pulled me to him and unzipped my dress and pulled it off me. He took off my bra and pushed me on his bed, my stiletto heels still on. He then did what no one had done for years—pleasured me. He fondled, sucked, licked my girly stick until I shot my wad, breathless. He was very beautiful. He began to fuck me, our bodies sweaty. Later as we lay on the sheets, and discussed the misogyny of Godard films and our mutual love of 1930s erotica, I considered I might be capable of a real relationship.
The next night (our first proper date) he took me to a restaurant at the very top of a hotel. In the elevator the sexual tension was so strong, I couldn’t help myself and took my panties off, which was easy because I was wearing a miniskirt. He began touching me down there just about the time the elevator made it to our final stop. We pushed the DOWN button, forgot about dinner and went back to his place.
After we were together about three months, Canadian Slim and I were invited to take care of a friend’s house in rural Northern California. We spent the first day hiking and exploring through beautiful grasses and countryside. The next day we woke up early: the ranchers down the valley were dynamiting holes and rocks, whooping it up. Canadian Slim and I had no choice but to get out of bed, pull the curtain back and let in the morning light and open the floor to ceiling glass doors. Canadian Slim exclaimed, “What a beautiful morning,” pointing out the different trees on the ridgeline and breathing in the clean air. I brought out some coffee and gave him a kiss. “This is the life,” he said, pulling me close, and I smiled in agreement. Over the top of the hills we saw a plane off to the south and then a feral cat hushed on by, just past the stairs. I threw a piece of sausage in the grass just in front of the cat, because I always liked cats and I was wondering if she might eat it. The cat stopped, sniffed the sausage and looked back at us before taking a big bite. Slim came up behind me and began softly kissing my neck. I prayed this relationship would work out.
Last night was our ninth anniversary. We had dinner in the Castro and were walking by one of the boy bars, when a drunk older gentleman yelled at Canadian Slim, “Lose the fish, honey,” referring to me. We both laughed at his obnoxiousness, and also at the fact that he didn’t know he was looking at a transgender couple. I felt some satisfaction, I admit, at having my gender affirmed by this clown, and so did Slim.
When we got back home I slipped into the bedroom and put on a
red satin corset, matching G-string and red silk stockings with garters, with my fuck-me pumps. I invited Slim into the room. “I think I’m going to get lucky,” he said. “You’re psychic,” I replied and took off his shirt and caressed his masculine chest and his beautiful chest scars. “You’ve been very bad,” I told him and pushed him onto the bed. I got his pants off and flipped Slim on his stomach and begin to lightly spank his taut ass. I got his underwear off and lubed my fingers and began to work his ass very gently. I pulled out my Colt ten-inch dildo and fucked him in the ass and I reached underneath and stroked his tranny boy cock. I worked that dildo and touched his cock until he finally moaned, and his body shuddered with coming.
THE HITCHHIKER
Sinclair Sexsmith
Get in,” the driver said, after flipping the dial on the stereo of the small blue pickup truck, quieting Big Black’s “He’s a Whore.”
Alice leaned her elbows on the window, made her legs into an A-frame, tipped her ass to one side and flipped her wheat-colored hair over her shoulder. She could spot one when she saw one: someone else with an insatiable appetite, someone who would take her for a ride, someone who would play dirty and queer and like they do in the bad films.
She took a long look at the driver: the blond fauxhawk, messy overalls, lean defined arms in a life-partner beater, dark tribal tattoos peeking out from the collarbone. A dark, worn cowboy hat sat on the passenger’s seat. The driver flashed a nice smile: simple, a little mischievous.
Until now she didn’t know it, but this was who she had been waiting for, and this was exactly why she’d hitched all the way to the good beach by herself today.
The scent of grass and sod wafted from the back of the truck. Alice spied power tools, a lawnmower, some rakes and shovels secured to the racks in the back. She gripped the handle, opened the door and slid onto the vinyl bench seat, taking the cowboy hat into one hand and easily sliding it over the crown of her head.
“My friends call me Jack.”
“I’m Alice.” She slid her eyes sideways to watch Jack maneuver the stick shift as the pickup pulled back onto the Pacific Coast Highway.
“Where you heading?” Alice asked.
Jack watched as she adjusted her long legs and ran one ankle against the opposite calf. “Wherever.” Good answer. South on the PCH was good enough for now. Alice wanted to end up in the city somewhere, it didn’t matter where. Cliffs and beach rolled by their windows. This was as good a direction as any.
The cab smelled like grass, too; grass and dirt, but in a clean, organic earthy kind of way. “You been working in the sun all day?” Alice asked, tossing the hat onto the dash, then flipping her hair again and strategically placing her elbow over the back of the bench seat between them. Her fingers were dangerously close to the overall buckles. The skin beneath was tan, a little pinkish.
“Yep.”
“It was nice today. Not too hot for August.”
“Yeah.”
“So you’re a gardener?”
Jack downshifted through a tight curve and held the clutch in a moment too long. “Landscape architect.” Pressure on the engine. She watched Jack’s mouth move and wanted to taste it already. Wanted to feel its suck and bite.
“Of course. You enjoy that?”
“Yeah, I do.”
Alice let her fingers drift onto the muscles of Jack’s upper arm; soft skin. “You look like you’re good at it.” She let herself picture Jack shoveling, digging; big bags of fertilizer slung over these broad shoulders; squinting in the sun.
Jack didn’t answer, just smiled softly, looking out at the road. Concentrating. Waiting. Already playing the game. The quiet was comfortable. Alice lifted her small satchel bag from her shoulder. “Do you smoke?” she asked.
“No.”
“Mind if I do?”
“Go right ahead.” Such a gentleman. She rolled the window down a crack, lit an unfiltered Lucky Strike from a soft pack. Only a few more left. The small cylinder felt good between her fingers, on her lips. She slipped her slender tan feet out of her white beach sandals and brought them up onto the seat, exposing her creamy caramel inner thighs. They rode in silence as Alice smoked, Big Black still soft on the stereo. Jack watched her from a sideways glance, one hand on the stick shift, palm starting to sweat, not making a move, not yet. Alice’s tank top exposed her toned navel and hip bones peeking out from the top of her tiny jean shorts. She brought the cigarette to her lips deliberately.
Jack took a breath, still not looking at her. “I like the way you do that.”
“Yeah?” Alice leaned against the door, moved one leg farther up onto the seat between them. “I like the way you drive.”
The corners of Jack’s mouth curled. “Thanks, darlin’.” Her toes shuffled toward the exposed side of the overalls, the thin, thin fabric of the undershirt. Jack shifted in place, muscles tightening and releasing quickly, expertly.
Alice watched, considering Jack’s hard body, the sweet smell of sweat and physicality. She flicked her cigarette out the truck window and rolled the window back up, pulled her knees up underneath her, leaned in close to Jack’s ear.
Now.
“Any interest in a fuck?”
“Uh,” Jack’s eyes flashed. Alice already had her hand on the bulge in the crotch of Jack’s overalls.
“I’d like to see what you’ve got under there.” Jack unsnapped the shoulder buckles, pushed them out of the way. Alice pulled a thick, marble-blue-colored strap-on from soft gray Calvin Klein briefs. It was bigger around than her hand would fit. She milked it with her fingers, real as anything. Her mouth watered for it. Jack’s eyes never left the road, but were increasingly glossy with lust.
“Looks good,” said Alice. “Big and hard already.”
“Gave me quite the boner, you on side of the road like that.”
That’s right. Play with me. “Oh yeah? Little ol’ me?”
“Soon as I saw those legs, I wanted them wrapped around me.” Alice bobbed her hand in Jack’s lap, dipping her face nearer to the cock, small murmurings of mmm coming from her mouth. Jack left one hand on the wheel and didn’t slow down, hugging the curves of the road with precision. Her lips grazed the head, licked it like an ice-cream cone with her long tongue, sucked it into her mouth while she left her hand pushing into the base of the silicone.
Jack groaned. “Damn, you’re good at that.”
Alice smiled and sucked; swirled her tongue; worked the head against the ridge at the back of her mouth; applied pressure.
Jack moaned again, deep, from the gut, hips thrusting a little, heavy foot on the gas pedal, not slowing, eyes on the road. Jack took a blind curve around a cliff, suddenly swerved into the dirt pull-off overlooking the beach and cut the engine. Alice didn’t stop, head bobbing on the delicious blue cock. Jack leaned back, feet on the floor, hips lifting, hands gripping the steering wheel and then the ceiling of the cab, pressing against the truck at every angle to get the cock farther down Alice’s throat.
“Fuck.” Jack shuddered, bringing a hand to Alice’s long hair and pulling her off of the cock. She wiped saliva off her mouth with the back of her hand, lips swollen, eyes wide. Waiting. She had made it real; now it was Jack’s turn to make her real. To fill up her desires without apology, without Madonna or whore complexes, without any stereotype of her girlyness, but with only the raw instinct of their animal-brain hunger. She wanted to feel that insatiable appetite coursing between them, body against body, mouth to skin, silicone sliding inside. That’s the way she liked to open.
What’s next, Jack?
“Come with me.” Jack threw open the door to the cab and half guided, half dragged Alice out of the driver’s side door. The sun hit them both, insistent and thick on its fall into the ocean. Jack pulled the tailgate down and hopped into the back of the truck with one quick leap, then leaned and offered a hand to Alice. Barefoot, she climbed in.
There was not much room with all the tools. The lawnmower was covered in flecks of
grass and a dark petroleum lubricant for its rusty engine, and it sat next to a red gas can, both with a strong, pungent smell. Dirt stuck to Alice’s bare feet. She made her way up to the cab of the truck and pressed her stomach to it, lifted one leg at the knee and stared out into the beach and setting sun, at waves lapping. It was pretty much deserted this far out of the city. A sporty two-door car zipped past, then it was quiet again.
From behind her, Jack let go of the overalls and they fell, exposing skin and muscle and curling tattoos, and seemed to gather the courage to stay that way. Alice had her thumbs in the waist of her shorts, a promise, a reward, and twisted around to face Jack. She barely glanced down, knowing the tenderness of overexposure, of gazes too thick on your misaligned places, of scars on chests now chiseled like David. She stepped close enough for them to feel each other’s breath and whispered, “You’re gonna fuck me with that big thing of yours, aren’t you?”
Jack’s mouth watered. “Yes.”
“Do it then.” She bent over the cab of the truck, slithered the shorts down over her ass and left them at her knees, creamy tan beach skin exposed, cunt exposed, neck twisted to watch Jack approaching.
Jack slid the cock into her in a swift gasp, stretching her taut. Alice lifted onto her tiptoes to tilt her pelvis, curve her back. Jack took hold of her hips and thrust, hard, and again, and again, thick inside her.
“Tight little pussy,” Jack murmured, one hand on her ass, spreading her cheeks. “Feels so good to open you with my big cock.”
Jack thrust harder, grunting. “Aw, yeah; aw, god, yeah.” Alice gasped with each hard thrust, impaled, in a bit of pain but also exquisite sensation, hips pressing apart, back arching deeper, mouth open and gasping. She lifted one foot up onto the three piled bags of garden dirt in the corner of the truck and spread her legs for Jack.
Take Me There Page 18
