Mile High

Long time lurker, first time poster. I wrote this while horny on a plane, and it is all fantasy and intended as fiction. Apologies in advance for formatting issues.

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What to wear on the plane?

Mary sighed, looking over what she'd put together. Sweats were okay, but even those felt too constrictive right now. She'd have to be on that plane for 10 hours, after all. A skirt? Maybe, but then she'd have to shave, ugh. And maybe deal with pervs... after all, for someone who barely hit 5'4", she seemed to have legs for days. Okay, a longer skirt, that would be fine. It would give her freedom of movement, and this particular airline was so stuffy all the time.

Her phone buzzed as she was selecting a t-shirt to match it and she groaned upon reading the message. She was on planes for her job so often that they sometimes even scheduled meetings close to a flight... or in this case, on it. A t-shirt wouldn't work, it was a video meeting with their VIP of sales. Sighing, she went instead to a button-up. She hated them, honestly. Button-ups and a bosom never went well in the long run, and these shirts were always too tight around the chest. Mary knew she should give in and just splurge on getting tailored shirts, but she liked to save up too much.

And hey, she was pretty certain the shirts were what got her this promotion in the first place.

Soon she was out the door, and in almost no time she was fast-tracked through security and waiting in the lobby. Usually the area would be more full of people, even for a red-eye, but it was oddly empty.

Mary noticed it was still fairly empty on the flight as well. As she looked at her empty row, the captain's voice filtered through her airpods to offer the explanation. "Hey folks, a connecting flight before this got canceled, and most of our passengers were from there," he said, sounding bored. "Congratulations. If you do feel the need to stretch out and sleep during the flight, I recommend buckling up over your blanket. That way we can check if your seatbelt is fastened without having to wake you up."

Grinning, Mary settled in for a much more comfortable flight. She could run her meeting on the airplane Wi-Fi without fear of disturbing too many other passengers. And afterwards, she could go to sleep... she hated the seatbelt anyway and would gladly trade off being possibly woken so she wouldn't have to wear it. She poked her head up and only noticed a few other business professionals around, then clicked in for takeoff.

Everything was coming up Mary!

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Henry glanced away when the redhead looked around, not giving away the fact he'd been staring. To her, he was just another faceless business person. He wasn't, actually; he was a psychiatrist who'd been hired to help a nervous passenger on the longest leg of their flight. A passenger who wasn't here to make it.

He'd been thinking about getting off, of course, but seeing Mary sitting in that quiet lobby changed his mind. He wasn't sure what he wanted to do, but Henry definitely wanted to do her. But how?

He watched her during takeoff, and moved a bit after to see her computer as she ran a short meeting. Her voice was nice, but he couldn't help but notice how the other participant's gaze focused differently if Mary shifted in her seat and went to grab paperwork. It had taken a lot of willpower to not stare himself at how different angles offered promises of a bounty. God, her figure was to die for. Even with that long skirt, he could imagine her thighs and what lay between. Henry started to get hard, forcing himself to stay calm.

For now.

He watched as Mary took down her hair after the meeting, shaking it out and braiding it for comfort. He watched as she unbuckled her seatbelt and shook a blanket over herself, provided by the airlines, and leaned against the window. And he watched as she took some pills, shoved the bottle into the pocket in front of her, and strapped on an eye mask.

He watched as she went to sleep. Then he got up and went to sit by her, contemplating his options. "We're going to do another check," the captain's voice came on overhead. "Then in a couple of hours, you will receive a hot breakfast." He continued with his announcements, Henry not listening at this point.

The flight attendants passed, pausing at her. "She's buckled," he offered, and they nodded without question, continuing. They didn't seem interested in much anything after that. One flight attendant went to the back closer behind them and promptly fell asleep strapped into their chair, the rest going up front to gossip, nap, and snack.

Ignored, Henry looked over the sleeping figure, and the box he held in his hands. The pill bottle at her knees showed a mild sedative, and he had a stronger, injectable one. It had been intended for the other passenger, but if he needed to use it here... He set it down and reached over slowly.

With quiet, still motions, he ran fingers over the fabric on her chest. Her breasts gave way slightly under the pressure of his hand, and god, they were so soft and full. Her bra wasn't even padded. Biting his lip and taking one more look around, he unbuttoned the top button. Then another. He got it halfway down her cleavage, the top of a low-cut bra just peaking through, before he stopped pushing his luck. It was enough for him to cup her breast while also feeling the soft skin above... heaven. Horny winning out, he undid another button, and they were almost spilling out. The light color of pink areolas greeted his eyes. What he wouldn't give to be able to grip them fully, take them out and fuck them with his thick cock...

Swallowing, his eyes traced over the rest of her. The blanket came up to her navel, and he could see how her body narrowed at the waist. He'd seen her hips, as well, the very definition of 'curves in all the right places.' He took the edge of the blanket and shifted it up, gauging her response. Nothing. When the blanket rested just under those heavenly tits, he snaked his hand underneath.

Hidden by the blanket, his fingers came to rest on her knee, then her thigh. Her skin was smooth and supple, and the pleated skirt easily shifted up as he slid his hand upwards. His eyes watched her carefully for a response, only sometimes looking around. When he got up to her upper thigh, finally, she shifted and sighed. He froze, but the only outcome was that her legs fell open more, slightly. Then Mary settled back down, and his cock was fully hard. With his free hand, Henry moved the blanket to cover his lap as well, and unzipped to release his throbbing dick. He didn't want to get too much precum on his pants, after all.

He could feel thigh, where it joined the leg, and then the edge of her panties. Thin and cotton, he used his touch to explore her mound, guessing that it was shaven. Fuck, this blanket surely wouldn't survive much. He slid down, between her thighs, where it was so, so warm. With one finger, he moved it down until he could feel through her panties where her lips parted. His finger rubbed down, then up, certain he could feel the small nub of a clitoris. He circled that, gently, almost lovingly, before moving down... up...

Mary's lips fell open. The plane's engine caused too much background noise to hear the heavier breathing, but he could see pink on her cheeks as his reward. With no other reaction, he continued exploring, sometimes breaking off to touch where panty met skin, sometimes using his fingers to simply rub over the lips.

A large smirk suddenly crossed Henry's lips. My god, already? He thought as he circled the wet spot in he panties. Perfect. His eyes fixated on her breasts, he couldn't help but need a sample, his finger moving to the side and gently, slowly, hooking under her panties.

His guess was half-right; she was shaven down below, with a shorter patch maintained on her mound. As he felt heat, he then felt her juices, moving his finger to spread them along her lips. Easily. She was asleep, but she was getting so wet already. One, then the other, then a third finger was coated in the fluid before he slowly pulled his hand free. Tasting his middle finger nearly got him to groan on the flight. He saw her nipples were hard through the fabric still covering them and on an impulse shifted one bra cup down to rub some of her juice on a nipple. It tightened more in the air, with cooling pussy fluid and stimulation.

Mary let out a sigh. It was almost inaudible over the plane noises, but he could hear it. He left the nipple exposed and moved his hand back under the blanket, growing bolder. Within moments he was back to rubbing between her lips, panties shoved to the side, and his own cock leaking profusely.

Henry glanced back over at his box, unlatched with the shots all prepped, before his dick took over decision making powers. Her legs were spread enough for him to press deeper, find and circle her entrance... and push inside.

Mary sighed louder, still inaudible to anybody but him. She was so hot, so wet, and so tight around his finger. He pressed in, feeling the inside of her pussy with a firm pressure, fucking her so slowly. Now dripping in wet, his finger moved out to circle her clit, watching Mary start to pant slightly in her sleep. She must be having a great dream, he figured, and slid back in. He wanted this to be his cock so very badly. With a light groan, he slid in two fingers. She accepted them easily, and yet tightened around them with the additional intrusion, her hips even moving into the penetration slightly.

That was all he needed. With no flight attendants in sight and all other passengers too far away to notice, he started to properly finger-fuck her. He could start to hear wet noises over the hum of the engines and set his pace based on that, firmly pressing deep and feeling her quiver and flex under him.

And with that, Mary started to wake up.

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At first it was just a sweet dream. Mary was with her ex-boyfriend; they'd broken up a few months prior, as he was ready to get married and she wasn't quite yet. It was amicable, and she had to admit, dreaming about the sex wasn't uncommon.

But other things started to get confusing, and she could feel bits of the dream shifting away and being replaced with reality. Why could she feel someone's hand? Why were the tops of her breasts cold?

And one part o the dream that was surely real: she was getting close.

Mary opened her eyes to darkness as her body stiffened around fingers, snapping back to the plane in a state of bliss. It was confusing, disorienting, and the sleeping pills she'd been prescribed didn't help the matter any. Which was probably why she didn't reach up immediately to yank her eye mask down when she realized what might be happening, what could be happening, what must be happening.

Her orgasm subsided slowly, fingers coaxing aftershocks out of her like an earthquake. She reached down to grasp a wrist--to push it away, to keep it there, she wasn't sure, but it wouldn't have mattered anyway. The arm was strong. Mary's full lips were flushed a dark pink as she panted, formed into a perfect 'O.'

"Fuck," she heard growled by her head. A man... the person violating her. Before she could react, the blanket was thrown off, and she felt her head being grabbed... and shoved down.

"Wh--" She hadn't gotten out even a word before her mouth was shoved onto a cock, and the blanket replaced over her. Struggling didn't help, the angle didn't give her leverage against her opponents strength, and he easily forced his full length past those plush lips. He wasn't long enough to slam into the back of her mouth, but he was thick enough to fill her up and almost completely muffle her noises of protest. Her hands went to push at his, then at his thighs, as he moved her head over his cock, but his only response was to speed up. His hands held the mask in place, so she couldn't even do anything to try and see.

She heard a quiet groan from above, and he held her mouth so that the tip was just inside. Hoping he was done, she was disappointed when he instead began to just fuck her mouth, hips thrusting up, salty precum coating her tongue and running out of the corners of her lips, mixed with her saliva.

He shifted to just grip her hair in a strong grip, and she almost thought to take advantage of the lack of two hands holding her in place. But then that free hand was shoved down the blankets and once more she felt fingers shoved inside her overly-sensitive opening. Even his cock couldn't quiet muffle her squeal at that, this man fucking both her mouth and her quivering pussy at the same time. Fuck, fingering was one of her joys in life, and he seemed to know exactly the right angle. Already aroused, she didn't stand a chance, and after a few minutes of being violated at both ends, Mary could feel a crescendo growing. No! She screamed in her head before coming, even harder, her vision going blurry with the force of it.

A few seconds later, the hand left her dripping cunt to return to her head and hold it in place as he shoved deep inside her mouth. Mary realized what was happening to her horror moments before he shot his load into the back of her throat. She tried not to gag, but he held her in place for long enough that she was forced to swallow or suffocate.

Disoriented with sensation, Mary sat up, coughing and trying to catch her breath. A stream of cum left her lips and fell across her heaving breasts, falling against the window in a weak attempt to escape her molester.

It seemed she no sooner got her thoughts sorted enough to reach up and try to take off her eye mask that she felt a prick in her arm and they became blurry again. "Who...?" She gasped, before her work got dizzy, and she fell back asleep.

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Mary blinked away and sat up suddenly, looking around as a hand fell on her arm. Her heart was racing all over again, but... huh.

"Ma'am, you need to buckle in," a flight attendant gently said. "We're about to land." She was clean. Mary pulled off her blanket and looked down to see her clothes were all in order, if a bit sleep-wrinkled. No saliva, no cum or taste of it, nothing to indicate that it was anything but a bad dream. A weird dream, at least. More filtered in... waking up in a daze to drink some juice offered by an attendant before passing out again... She'd mostly slept for those ten hours.

What the hell was that?

She shook her head and just shakily gathered her belongings together pack them for the landing, then gathered up her things for disembarking. Picking up her baggage was a tired blur, and before she knew it, she was outside walking towards the taxis.

Mary thought then to pull out her phone and unlock it, planning on emailing her work and letting them know her ETA. Once past the Lock Screen, though, she froze.

Her home wallpaper was her. Rather, it was her in a state of disarray... breasts falling out of her shirt, passed out backwards against the window. Her skirt was up to her waist, showing her panties pulled down and exposing a dripping pussy. There was a liquid shine around her mouth and on her tits.

Mary flushed and slammed her finger on the lock button, the screen flickering to black as she froze, processing. It hadn't been a dream. A strange man made her cum twice on the flight before finishing in her mouth. She leaned against the wall, not noticing a distant man watching her carefully before she hurried off to the taxis doing double time.

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"Mary?"

Mary looked up from her phone to her boss. Now, a couple months later, that flight was a memory. Maybe a distant one, something that horrified her, but... maybe she'd also gotten off a few more times to it. Whoever it was, they'd played her body like a fiddle, and being rough was something her ex would never do even if she'd been curious. That, and her negative STI test, were the biggest reasons she hadn't reported it. "Yes?" She asked, putting her phone in her purse.

"We're expanding your job to include a few new products. We've gotten FDA approval and will patent these antidepressants within a few months, so we need an expert at your side until you've learned all the details." Mary noticed the man by his side, and vaguely wondered why his smile was so big.

"Mary, meet Henry."