The Mile-High Club

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I cleared my throat. “Excuse me. Sir?” Groggy with sleep, I just wanted to get into my seat so I could doze for a few hours. Lo and behold, though, I was looking into the gorgeous face of my seatmate, a slightly older, straight-looking guy smiling politely at me. “Fuck,” I thought. “Why do I always dress so dykey even when I want cock?” I had dated a series of women who were progressively more masculine, and at the end of the day the passion just fizzled out. I was all but ready to give up on dating altogether; identity crisis after another forced me to change my gender presentation over and over again. Here I was in some relaxed jeans held up by a leather belt, a cozy quarter-zip sweater, and my short hair peeking out from under a slouchy beanie. I must look majorly confused 80% of my days.

The man got up to let me slide into my window seat. I tucked my messenger bag under the seat in front of me, sat down, and slouched comfortably into my chair to send a few texts out before shutting my phone off. From the corner of my eye I saw the seatmate sit down, sneaking un-subtle glimpses at me.

“Hi,” he said, in a low groggy voice of a tired traveler, but with the perkiness of someone who was happy for companionship. “I’m Jake.”

I held out my hand to him. “Ray.” As soon as I said it I blushed; I should have just said Rachel; he knows I’m a girl. But I wasn’t feeling “Rachel” today.

“Nice to meet you,” Jake said, glancing me over again.

I was still blushing, so as soon as our hands parted I turned away and looked out the window. He seemed to want to talk more, but he ran out of stuff around him to look at besides me, so he finally reached over to pull out his book and start reading. Soon enough we were airborne, sailing eastbound to Amsterdam.

A 10 hour trans-atlantic flight and I was already turned on, the sock in my pants seeming foolish and unnecessarily distracting given that I’m pretty sure I didn’t pass. I was a foolish woman who didn’t know herself. And this guy was… wow. I snuck a few glances over at him, and his bulky arms that filled his shirtsleeves to the brim, his stocky masculine build, a body that could squeeze me tight and make me feel close, a crotch that contained…

“Jonathan Franzen?” I jumped at the sound of his voice. I’d obviously been checking him out, my eyes having wandered over to the bulge in his pants, my book forgotten in my hand. I let out a small laugh. “Ha…yeah, have you read it?”

“Yeah I’ve read it 3 times, how far in are you?”

“Page… 3…”

Jake laughed. “I won’t spoil the end for you, Ray. You seem like a guy who’d enjoy it.”

He said guy… he said guy!! I felt scared and validated at the same time, that he read me as male; or at least, that he respected my presentation. “I love a good ending.”

“Yea me too, especially a steamy one.” Seeing the shocked look I gave him, he laughed coyly. “What, I’m a sucker for those kinds of books. Not that the one you’re reading has that, but just you know, in general…”

“Does that book you’re holding have a steamy ending?” I pointed at a paperback he was holding that had clearly come from the airport’s news stand. The thought of him reading something hot while sitting next to me made me get worked up. How’d we get on this topic anyways?

“Nah, I figured it’d be inappropriate for a 10 hour plane ride next to a complete stranger.” I think my face betrayed a little disappointment. “I do have one in my bag, maybe when we get to know each other a bit better.” I chuckled.

“Hey it’s a free country. I won’t stop you.” I smiled.

“Thanks for being so cool, man.” He looked me over one more time and then turned to his book.

“Yeah man.” I leaned my seat back, pulled my hat over my eyes, and closed my eyes. A guy reading romance novels, and freely admitting it, was clearly open about gender and sexuality. As I drifted off, I wondered what dirty thoughts went through his mind.


I woke up half an hour later, trying to get comfortable. My pants were bothering me. I looked around and noticed that he was still sleeping; carefully, so as not to bother him, I grabbed basketball shorts out of my bag and got up to go to the restroom. I tried squeezing between his legs and the seat in front of him, but we hit a spot of turbulence and I accidentally fell onto his lap. He woke up with a start, me sitting on top of him. “Whoa Ray, buy me dinner first, huh?”

“I’m so sorry, I just had to use the bathroom.” I stood up. “And dinner? Come on, that’s only worth a drink.”

Jake smiled at me as I walked away. “Better be one hell of a drink.”

Five minutes later I came back, wearing the shorts, holding bahis firmaları my rolled-up jeans in one hand and a can of diet sprite in the other. When I got back to Jake, I tossed him the can. “Your drink.”

Jake laughed. “Diet?”

Fuck. Getting a can of diet soda is a bit of a slap in the face for anyone. “Oh wow, I just grabbed the first can I saw. That’s not what I meant at ALL.”

“Hey don’t sweat it, I was only kidding. Here, we’ll share. Even fewer calories for me.”

“I don’t think that’s how it works! But yeah ok since you got a lap dance and a soda from me, the last you can do is share…”

Jake smiled and popped the can. “I hope you’re ok sharing, I don’t have any communicable diseases I think.”

“It’s fine,” I said as I took a sip from the can his lips had just touched. “It’s basically like kissing which isn’t a big deal, so.”

“Really? Kissing isn’t a big deal? So how bout this?” With that he leaned over and kissed me straight on the lips.

I was stunned and turned on, and started to kiss back, but being dressed as Ray, I felt like I had to play it off like I was into women. With my most exaggeratedly masculine mannerisms, so he’d know I was joking, I wiped my mouth with my sleeve. “Duuude, c’mon!” I punched him playfully in the arm.

“Ow! That was the sharpest jab!” He shoved back at me with his elbow. “You’re an ass,” he said, rubbing his shoulder. I loved the teasing and the exaggeration; there was no way I actually hurt him. But yes I was a little out of line; I loved getting physical with another guy and having him acknowledge the exchange of physical contact as a sparring of equals. Whenever I’d punched my ex’s arm, she would just tell me to stop it and walk away, as if I was out of line for who she wanted to date.

“Sorry.” I reached over and rubbed his shoulder for him. “Is that better?” I worked his big muscular deltoid under my fingers, gently caressing the flesh. He looked at my hand and then at me, smirking.

“Getting there,” he said, winking and grabbing the soda from my hand. I smiled and opened my book up to read a bit more. As I slouched down and sprawled out, our thighs touched between our tiny seats.


An hour later, the sun had set and the sky was dark. We were flying away from the sun, speeding up the transition into nighttime at an unnatural pace. They turned off the cabin lights, as if to coax us all to sleep; sure enough I started feeling myself lose focus on my book. Jake’s tight strong body next to me wasn’t helping matters.

I decided to try and get more comfortable in my seat and try to keep my mind off Jake. I leaned my chair back and tried to get comfortable but a knot in my back kept me from settling in. I turned to my left, and to my right, every which way. Finally I turned to Jake, who was reading his own book. “Mind if I put the arm rest up? I’m dying to find a position that’s good for my back.”

Jake smiled at me. “Yeah, sure. You can put your feet up here if you want.”

“Really? Thanks Jake.” I curled my feet up into a fetal-ish position, taking up the space where the armrest used to be. My back began to unknot. I didn’t mind that I was right up against Jake, and it seems like he didn’t notice either. My ass was resting touching his thigh, and his arm was resting on my thigh. As I settled in, I zipped my sweater all the way and crossed my arms to get warm. Jake must have noticed.

“Do you need a blanket?” He produced a dark blue standard-issue flight blanket from under his seat.

“That’d be awesome.” I helped him drape the blanket over me; I was surprised that he had draped it over his arm that was resting on my thigh. My clit began to throb against the sock in my shorts; I couldn’t help but squirm a little to shake off the sensation.

I noticed he was reading his steamy romance instead of the book he came with; I guess we were friends now. He finished his page and then single-handedly tucked it into his seat-back pocket, never taking his other arm off my leg. He started slowly caressing my leg, the silky material of the shorts gliding under his hand. I squirmed a little more. He then shut off his reading light. Most of the other passengers were asleep or watching movies; I felt like we were invisible.

I had no idea what would happen next. As his hand slowly started stroking my thigh, he leaned over so he could speak to me quietly: “So, little Ray, do you like cocks or pussies?” What?! I was shocked at his transparency… and more than a little pleased.

I smiled up at him as I reached back to stroke his cock. “I like a balanced diet.”

He closed his eyes for a second as I worked his bulge through kaçak iddaa his jeans. “So you’re a little fag,” he said. I cringed at the word but I knew it was true; I nodded. “Me too. I love a boi with a tight hole.” I was hoping he meant boi with an “i”; I assumed the best and kept leaning into him. He started working his fingers toward my junk, rubbing over the sock and pressing into my clit. “Tell me, Ray, do you like getting fucked? Your body language tells me you do, but I want to hear you say it.”

“Mmm, I love getting fucked.”

“By who?”

“By big strong men with big cocks.” I don’t know where these dirty words were coming from; I’d never talked dirty in my life. But here I was feeling confident, feeling clandestine, feeling daring. Life was full of little moments like this… moments that, if I didn’t seize, I’d forever regret. I was feeling alive, my body on fire, my desire fueling me in this moment.

He moved my hand away from the fly of his pants, and unzipping his jeans, pulled his big stiff dick out and started masturbating it against my ass cheek under the blanket. I hadn’t seen one in years, and the feeling of it was absolutely incredible. I’d forgotten how much I used to want cock, how much I’d fantasized about cock.

Whenever I’d hook up with a guy as a girl, I felt used; I felt like there was a power imbalance and that I was doing a lot to satisfy a man who didn’t get how I felt. That, or he would be too gentle, too understanding, too mushy. But now, with my chest bound tightly and my curves obscured, my short hair having replaced my long ponytail, I loved being roughed up a little, humiliated, called names. I was a ravenous cock slut, because I was treated like a guy. I was a masculine creature with a masculine creature, and it made me feel incredibly empowered.

Jake started working the cock between my ass cheeks, between my thighs, the silky material gliding between my pussy lips and his dick. I was dripping wet by this point, and I was sure he could feel it through the thin material of the shorts. He started carefully pumping his hips, trying to be subtle, as he worked himself stiffer and stiffer. I was feeling incredibly worked up, wanting to swallow his cock up in my tight hole as he worked my cock with his fingers.

Finally he slipped out. I missed his presence already, bucking backwards to try and find his cock again but he had turned away. Then I felt him pull at the waistband of my boxers and my shorts, pulling the loose material down to expose my round smooth ass cheeks. Was he really gonna fuck me in public? Was he gonna… yep. There it is. He stuck two fingers into my dripping wet cunt and I almost cried out. He leaned over to speak softly to me: “I like my pretty boys with pussies.” He gave the fingers a slow twist inside me, and then really carefully and slowly slid out of me. Then he slid those lubed-up fingers down to my cock, sliding up and over the head, beginning to trace circles around it.

I came silently, spazzing with his fingers between my legs. With the blanket over us and the lights out, nobody could see what we were doing, but still I feared drawing attention to what he was doing to me under the covers.

I thought he was done with me then when I noticed that he had reached over to grab his cock. He guided it between my legs and started sliding it between my thighs right against my labia, my warm lubrication wetting the length of his shaft. Every time he’d move it he’d move the tip a little closer to my hole, teasing me with it. Finally, slowly, he started slipping into me, turning his hips toward me so he could get his whole dick in. “How does that feel, fag?”

It felt wrong for him to call me that, a tinge of anger, but I knew it was true. I was a fag and I liked being a boy and getting fucked by a stiff cock. “I’ve been waiting for you to fuck me since takeoff.”

“That’s cuz you’re such a slut, taking my cock without knowing me first.” He stayed inside me, my rippling muscles tightening and relaxing around his shaft. He didn’t want to thrust too much because it was too risky. So we stayed like that, his cock inside me, getting stiffer and stiffer, filling my hole with its girth, when finally the vibrations from the cabin and from my hole brought him to climax. His sticky juices filled me up and spilled out; he grabbed a napkin to catch what he could but it was too late; we were both a hot sticky mess.

He pulled out and tucked himself in, then motioned me to the bathroom. I pulled up my shorts and followed him 30 seconds after. I knocked on the bathroom door; he opened it and pulled me inside. Before he’d locked it he’d already shoved me against the wall and started kissing kaçak bahis me deeply. I grabbed his hair and pulled him in, needing his tongue in my mouth and his body pressed up against mine. His cock was stiffening again, and I grabbed his ass to pull him closer, feeling his hardness against my lower stomach. As quickly as I could, I undid the buttons and zipper on his jeans and pulled his delicious cock out. I started stroking it with my hand, but he pulled away. and turned us so his back was to the wall. “Get on your knees, fag.” He gently but firmly pushed me down. If I were dressed all femme-y, no way would I enjoy being treated like this; I didn’t even like sucking cock. But now that I was treated like a boy, I felt a jolt of pleasure every time he ordered me around, pushed me around, called me derogatory names.

There was barely enough room in the bathroom, but I managed to get down on my knees to get eye level with his shaft. I grabbed it with one hand and started licking the tip of his cock. It tasted like pussy juice and cum and precum and sweat. He put a hand on the back of my head and shoved me down onto his dick. I took the entirety of it into my mouth, sucking it like it was the most delicious piece of meat I’d ever tasted. Sucking this man’s cock on the bathroom floor of an airplane almost felt too dirty, but then I’d feel the tip of it at the back of my throat and choke on it, and I knew I’d do anything to have that cock, anywhere.

As he was about to come, he pushed my face away, taking his cock out of my mouth. “Come here, fuckslut.” I stood up and tried to kiss him; he refused and turned me around before sticking his hand down the front of my shorts. We were both facing the mirror now: a grown man kissing the neck of a butch person with their chest bound tight and their hair cropped short. A grown man jacking off a young guy, pressing his cock into his back, pushing his fingers into his hole, holding the young guy with his strong insistent body.

I wasn’t sure where he was going with this, so I leaned back against his chest to ask him, “what now, boss?” This seemed to be the catalyst to bring him back into action. “This,” Jake said. I was puzzled for a split second before I felt him push me forward by my neck, grabbing my hips, bending me over the sink. I braced myself on the counter as he held me there, pulled down my pants, and started fucking my pussy from behind. But as soon as it got wet enough, he stuck a finger in there, pulled it out, and started playing with my ass. He got the rim good and wet, then stuck his finger tip in slowly. I gasped; I’d never been penetrated in two holes at once. He eased his finger in, stopping if I gasped at the pain; it did hurt a little but the good feelings outweighed the bad. I gave in, closed my eyes.

Suddenly I felt him pull his cock and his finger out, and then before I knew what was happening he pulled out a bottle of lube and easing his slick tip into my ass. I felt a sting of pain as his big cock stretched me out; then a tingling as it eased into the most amazing feeling. He carefully pushed in, still holding me forward firmly but guiding himself in slowly. I felt incredible; I’d never been filled like this before, and it made me feel like I was born to bottom a guy like him. I’d never felt more whole.

He took his hand off my upper back where he was pushing me forward and put his hand on my hip. Slowly, he started working himself in and out a little bit at a time. He started inching the hand that was on my hip down to fuck my pussy as he fucked my ass. As soon as he slipped his fingers inside me, the palm of his hand resting on my clit, I let out a loud moan. I didn’t care who heard; I was beyond that. He started fucking me harder, filling me with his stiff cock and his slick fingers and playing with me til I couldn’t control myself any longer. He gagged me with his other forearm, shoving it against my mouth to keep me from screaming out, even as he fucked me harder. I couldn’t move; I was being held up by his whole body, keeping me from collapsing on the ground. He kept fucking me faster and faster until finally he came again, filling me up with his cum; I came too, moaning into his muscular forearm and squirming against his body and all the stimulation he was giving me. I was his boy toy, I was his bottom, I was born to be fucked like this.

Jake pulled out, we cleaned ourselves up, and headed back to our seats. We looked at each other, smug in how we knew we could make each other feel.

“Thanks Jake, that was… fucking mind-blowing.”

“Hey, it was the least I could do for that drink.” I laughed. “And thanks yourself Ray, for being such a good sport.”

“Hey, now I know what kind of queer I am.”

Jake smiled, and as we began our descent he threw the blanket over our legs and started working his fingers down my shorts again, hungry for more of my throbbing clit and pussy against his fingers…

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