“You haven’t forgotten your promise, have you, Hailey?”
My best friend Jessica grinned at me as I turned to look at her, playfully flipping her off as I did.
“Ooh, somebody’s cranky!”
“Well, what is it, 5am? And we were up until what, 2am? Yeah, I guess I’m a little cranky. Plus my friend keeps reminding me what I agreed to last night.”
“Oh, well, forget it. With your luck, it’ll probably be some little old lady.”
We both giggled, and started picking up our bags as we heard over the airport PA system that our flight was ready to board.
Sorry, let me give you a little background. Jessica and I had been best friends since we were little kids, and most recently, had been college roomates. That is, until yesterday, when we’d walked across that stage to collect our diplomas. Today, we were off on a trip my grandparents had surprised me with as a graduation present - an all-expenses-paid week in Hawaii.
It had been a whirlwind afternoon and night, packing, making arrangements to go away on such short notice. And then there was our sudden realization of the fact that neither of us had ever been on a plane. A few glasses of wine later, Jessica was fine with that, but I was still nervous. Maybe that’s what happened when you’d never been on a plane and you’d watched the movie ‘Airplane’ a few too many times. Those jokes were funny as long as you didn’t have to actually, well, fly.
That was when Jessica came up with a creative new method for overcoming a fear of flying.
“How about this, Hailey. I’ve got an idea to get your mind off the flight. Promise me, if there’s a hot guy seated next to us, you’ll give him a blow job.”
“What? That’s ridiculous! I could never do anything like that!”
“Oh, really? I’ve seen you bring home a guy on the first date, how’s this any different?”
“Jeez, it was just the one time, am I never going to live that down?” Sometimes having a friend who knew everything about you could really come back to bite you.
She laughed. “You have to admit, thought, it’s gotten your mind off of flying, hasn’t it?”
“Yeah, really! OK, fine, I promise. If there’s a hot guy seated next to us, I’ll be all over him.”
So, that brings us back to that morning, working our way onto the plane, down the aisle past first class and into the zoo that was coach. I looked up at the seat numbers as I walked, slowly, stuck behind an extended family with little kids and older relatives to get seated before I could move on. Ah, finally, I thought to myself as I saw row 36 appear just ahead. Let’s see, which direction was it, right or left?
And that’s when I saw him. In the window seat, 36A, just next to the empty seat which I soon realized was mine. His handsome face was the first thing I saw, chiseled features and tan skin with just a hint of travelers’ stubble. I guessed he was in his early 40s, and quickly assumed from his finely-tailored suit and the laptop on the tray in front of him that he must be traveling on business. He looked up when he sensed my presence, smiled, and moved his jacket off my seat. I blushed as his deep blue eyes met mine, and sat down.
Jessica snickered as she took her seat across the aisle from me. I looked past her to see - no joke - a little old lady seated next to her. Some luck.
“You sure you don’t want to trade?”
“Hell no, Hailey, I can’t wait to see how this one turns out!”
The hot guy had gone back to working on his laptop, and did so without looking back at me until the plane finally got ready for take-off and the pilot gave instructions for people to turn off electronic devices. At about the same time, any thought of my naughty promise to Jessica had left me, and I was back to worrying about plummeting from the sky.
My neighbor must have sensed my tension, as I felt his hand on my arm and heard his voice for the first time, “Hey, are you alright?”
“Hmm? Oh, um, yeah. Just my first time flying, that’s all.”
“Well, don’t worry. I fly all the time, and it really is true what they say, that you’re safer in an airplane than on the highway. My name’s Jeremy, by the way.” He reached out his hand, and as I shook it, I noticed that my hands were cold and my knuckles were white from clutching the seat. Yikes, I really did need to find a way to relax.
“I’m Hailey. And over there,” I said, pointing across the aisle, “is my best friend Jessica.”
“Nice to meet you, Hailey. So, what brings you and Jessica to Hawaii?”
The story spilled out of me - from graduation, to my grandparents, to how long I’d known Jessica and what good friends we were, to what my major was, to why it was that I’d never flown before. By the time I stopped talking, I realized that we were in the air, levelled off, and cruising comfortably.
“Wow, Hailey, that’s a bundle of nerves you brought with you this morning. Are you feeling more relaxed now?”
“Yes. Um, thanks for listening! Sorry, I should let you get back to work.”
I knew I’d take shit from Jessica, but I just didn’t have the nerve to go through with it. I certainly wasn’t a prude, but I also wasn’t the type to proposition complete strangers.
“Oh, don’t be silly. I’d much rather get to know you better. I’m usually seated next to some little old lady on these flights. Or even worse, a businessman like myself. You’re a breath of fresh air!”
I blushed again. I glanced over at Jessica, and though she was pretending to read her book, I saw a smile form on her face and could immediately tell that she was listening to our whole conversation.
“Here, Hailey,” Jeremy said, getting my attention back, “take a look out the window, it really is quite a view from up here.”
I leaned over him to look out the window, but quickly jumped back at the view, my fear of flying momentarily coming back. But he gently grabbed my shoulder, encouraging me to give it another try, and pointed out specific things for me to look at, until I relaxed again and realized it really was pretty cool to look down from this altitude.
“Would you excuse me for a second, Jeremy?”
“Certainly.”
I stood up, motioned to Jessica for her to follow me, and walked towards the back of the plane, pretending to head to the bathroom.
“I can’t do this,” I whispered once we were out of his earshot.
“I knew it, chicken! Come on, this is supposed to be a trip just for us to celebrate - why don’t you live a little!”
“But he’s, like, a really nice guy. He’s actually the kind of guy I’d want to get involved with, if he weren’t, you know, twice my age.”
“Why can’t you just admit you’re chicken? I knew you wouldn’t be able to do it.”
How was it that Jessica always knew what button to push, without me even knowing she was pushing it?
“Oh, really? That’s what you think? Just watch me.”
We walked back to our seats, and I flashed Jessica a determined look before turning back towards Jeremy.
“So, sorry again to talk your ear off before. But it really did help me relax. Thanks for being willing to listen.”
“Hailey, it was completely my pleasure. You have a lovely voice, even if you were babbling just a bit.”
He winked, and I knew this was my opportunity.
“You up for another story?”
“Sure...”
“Well, you’ll have to tell me how this one is going to end. See, now that I’ve managed to get on a plane, there’s something else I’d like to see if I can do as well.”
“Oh, really? What’s that?”
I leaned in closer to him and whispered in his ear, “I told myself that if I happened to be seated next to a hot guy on this flight, that I’d seduce him and give him a blow job.”
Trembling with excitement, I leaned back into my seat, awaiting his reaction.
He put his hand on mine, and whispered in my ear this time, “I think that can be arranged. Listen carefully.”
He proceeded to give me detailed instructions, about how I should get out of my seat as nonchalantly as possible, walk around to the bathroom on the other aisle, close and lock the door, and wait for two minutes, after which time he would join me. I was only to open the door when I heard a specific knock, which he demonstrated by tapping on my arm. While waiting for him, I was to strip down to my bra and panties.
I tried to borrow some of Jeremy’s calm demeanor as I followed his instructions. I walked, as slowly as my racing pulse would let me, to the bathroom, closed and locked the door, and quickly stripped. I didn’t know until that moment, when I was surprised to see myself in reflection, that airplane bathrooms had mirrors. I admired my body for a moment, 5’7” of tan, fit, 22-year-old hottie, with long wavy blonde hair and big blue eyes. I realized how lucky it was that I’d chosen a sexy, matching red bra and panty set, when it would have been just as easy not to as I rushed to get dressed that morning.
This thought was interrupted by the knock I was waiting for. I opened the door just a crack at first, to make sure it really was him, before letting him join me in the tiny space. No more words or foreplay were required, as I dropped to my knees in front of him. He unbuckled his belt, unzipped his slacks, and let them fall to the floor before sitting down on the covered toilet seat and spreading his legs.
I began stroking his shaft with one hand and playing with his balls with the other, and he quickly grew hard in my hands. He reached down and gently weaved his fingers through my hair, forming it into a ponytail, and slowly pressed me down onto his cock, keeping my lips just on the tip for a few moments, before pushing more and more of his length into my mouth.
We found a rhythm and kept it up for a few minutes, Jeremy tugging at my hair to control my speed up and down, up and down, on his long, hard, cock. Just about the time I would have expected some of my old boyfriends to shoot their load, he pulled out of my mouth, and whispered for me to suck on his balls.
I eagerly did so, using both hands and mouth to play with him as he reached down and squeezed my tits. He held his cock back against his torso and hissed at me to look up at him with my big blue eyes as I sucked and licked and fondled. After a few more minutes of this focused attention on his balls, he once again forced himself deep into my throat, holding me down for what seemed like an eternity before letting me up for air.
“Good girl,” he whispered, “Now, are you sure a blow job was all you had in mind for me?”
“Um, well,” I replied with a wink, “it sounds like maybe you have a proposal I should consider?”
“I would really, really, like to fuck you. How does that sound?”
“Oh, god, yes.”
“Are you wet?”
“Unbelievably wet.”
“Stand up, I want to feel just how wet you are.”
I did as I was told, the blood rushing back to my lower legs as I stood up. He remained seated, and pushed my legs apart, his hands exploring my inner thighs for a few moments before reaching up to push aside my panties and feel my wetness.
I arched my back in pleasure as his fingers found my clit, and then found their way inside my pussy. He finger-fucked me for a few minutes before suddenly pulling out of me and grabbing me by the hips to pull me down onto him. Perhaps sensing that I was about to cry out, he forced his fingers - covered in my own juices - into my mouth. I remained motionless for a little while, before allowing myself to begin riding him, slowly at first, then gradually with more abandon.
Again amazed at his stamina, I was shocked when he pulled out of me just as most guys I’d been with would have been reaching their climax.
“You should really turn around, Hailey,” he whispered, “so that you can see what I’m seeing.”
I remembered the mirror, and eagerly did as he suggested. I stood up, turned around and once again straddled his legs so that I could lower myself onto him. The mirror wasn’t long enough that I could see him penetrate me, but it was thrilling to watch myself as I rode him - even more so after he freed my tits from my bra and reached around me to pinch my nipples before once again freeing them to bounce as I moved up and down, up and down, up and down.
It was then that I came - more powerfully than I ever had before - and once again had to rely on his big, strong hands over my mouth to keep from crying out and revealing to all the passengers in the rear of the plane that I was at the peak of my climax.
After I came, I realized he still hadn’t, and leaned back into him, whispering in his ear, “god, that was amazing. Tell me what I can do for you, anything...”
“Just stand up, Hailey, I’ll do the rest.”
I quickly stood up, and he followed, spooning me from behind in the tiny space. He forced my legs apart and thrust into me from behind. From this standing position, the mirror now provided a tantalizing view of my full torso and down to my upper thighs, so that I could watch him pound into me with each aggressive thrust.
His eyes met mine in the mirror as he reached around and held me by the hips to better control his motions inside of me, and I was amazed to find that I was quickly approaching a second climax - yet again, something I’d never experienced before. I’d never found my own body so sexy as I did in this moment, crammed into an impossibly small and uncomfortable space and yet completely enthralled as I watched my tits bounce with each powerful thrust of his big cock deep into my tight, wet pussy.
I reached down and shifted one of his hands to my clit, and he obliged, rubbing furiously as he began fucking me even harder and faster, clearly close to his own climax. I came almost immediately under this intense stimulation, my pussy clenching and throbbing around his cock and spurring him on as he finally jerked and shot his load deep inside of me.
He continued pushing in and out, slower and more gently now, until we gradually eased down to nothing, before finally pulling out of me and helping us both to get dressed and presentable once again. We quickly decided that he would leave the bathroom first and return to his seat, and that I would follow a few minutes later.
I can hardly describe the look that Jessica gave me when I finally settled back in my seat, but suffice it to say, she was thoroughly shocked, not only that I went through with it, but that we were gone for so long and looked so satisfied when we returned.
"You were amazing, Hailey. I'm glad you seduced me," Jeremy said with a wink.
I giggled. "You were pretty amazing yourself, Jeremy!"
"So, where are you and Jessica staying on the island?"
I pulled the paper showing our itinerary out of my bag. Jeremy smiled.
"We might as well share a cab."
"Really, are you close?"
He paused before answering, "Same hotel, actually."
"Wow." I turned to Jessica, and said, "it's going to be quite a week..."
