OSL: New York
Chapter 1: Mile High

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa, Fa/Fa, Mult, Consensual, Spanking, Light Bond, Swinging, Group Sex, Orgy, Oral Sex, Anal Sex, Sex Toys, Cream Pie, Exhibitionism, Double Penetration, Big Breasts, Public Sex,

Desc: Erotica Sex Story: Chapter 1: Mile High - A vignette to be read after An Ordinary College Sex Life 3.

-- THURSDAY, JUNE 15, 2006 --

The cool evening air was made even colder by brisk winds flowing in from the Bay, and though I was loathe to leave, I knew we shouldn't dawdle on the curb. Closing the driver's door of Adrienne's new silver Porsche Cayenne, I immediately went to the trunk to retrieve our luggage while Adrienne and Sasha both got out on the passenger side and began hugging their goodbyes.

There was a lot of luggage. Even though we'd only be gone for little more than a week, "traveling light" apparently wasn't in Adrienne's vocabulary. I'd known her since we were 10-year-olds growing up on the same suburban street. But now the 21-year-old blonde bombshell with hazel eyes and killer curves was a big time supermodel, appearing on the covers of the Sports Illustrated Swimsuit Edition and the Victoria's Secret Catalog. She'd mingled with the stars and made friends with powerful people like Taylor Brynn and Jonathan Kwong. Her magnificent cleavage was perhaps the most lusted after in the world, and one never knew when a lurking paparazzo might take her picture and splash it all over the news, especially in Manhattan. So she had to be prepared for any occasion, and rather than bother to meticulously plan out her daily outfits, she had seemingly decided to bring half her wardrobe for the trip.

Fortunately, life as a world famous model paid pretty well, and Adrienne had already arranged for the airline's VIP Service. An airline concierge greeted us on the curb and a skycap took over unloading duties, so I turned my attention to my actual girlfriend.

"Mmm-wah! Have a great flight!" Sasha kissed me, smiled, and leaned back in to nuzzle her nose against mine.

I grinned and was about to crack some joke or another, but a lump suddenly formed in my throat and my eyes got moist as I realized this would be my first extended absence from Sasha since she moved in. I quickly pulled my girlfriend into a bear hug and squeezed her tight. "I love you. I'll miss you," I mumbled into her ear.

"I know," she replied with a giggle. "Me, too. But don't worry about me; I'll be well taken care of this weekend."

I chuckled and pulled back far enough to look her in the eyes. "Tell Andie and the girls I said 'hi'."

"Will do."

"And I'll call you when I can."

Sasha snorted and gave me a wry grin. "Sure, whenever you come up for air between rounds of drowning in fresh model pussy."

I rolled my eyes. "This IS a work trip, remember. I've got a lot to prove that I'm a capable individual; that I truly deserve a job at Jonathan Kwong Enterprises and didn't just get it because my 'girlfriend' is chummy with the boss' wife."

Sasha's grin widened. "And you'll prove that just fine on Monday when you go into the office for the first time. But you're landing tomorrow and spending a whole weekend hanging out with HER." She jerked a thumb at Adrienne for emphasis.

I chuckled and shook my head. "True enough."

Sasha pulled me back to her for another kiss, and when I stepped away, Adrienne grabbed Sasha for one more 'goodbye' kiss of her own, every bit as passionate as mine. The girls murmured their endearments to each other, everyone waved, and Sasha headed around to the driver's side of the Porsche while Adrienne and I walked into the terminal.

Airport security would already have been a breeze this late in the evening, but our airline concierge escorted us through even faster. Then, rather than board the plane with the rest of the priority access customers, Adrienne and I stayed in the Airline Lounge until pretty much everyone else had boarded. And only at the last minute did our concierge escort us to the gate and usher us onto the plane just before they closed the doors. Our seats, 2H and 2J, were literally the first two against the bulkhead on the right side of the plane, and we more or less sat down without anybody getting a good look at Adrienne's face.

Even if someone had, Adrienne wore a black newsboy cap and aviator sunglasses which prevented easy identification. She also took the window seat, and while I noticed a middle-aged businessman in the center aisle letting his eyes roam up and down her spectacular figure (impossible to completely hide even in a knee-length coat), by the time the flight attendants began their safety briefing she was virtually ignored.

I'd been a little nervous about the whole VIP service thing. I'd never flown First or Business Class before or even been in an airline lounge, let alone gotten a special escort from the curb through security and to the gate. I kept thinking that other people were looking at us, wondering who we were while watching us bypass the "normal people" lines and have some guy in a suit wearing airline logos lead us around. Rather than give me a sense of elite privacy, the whole thing only made me feel embarrassed and put in the spotlight.

Adrienne, of course, acted like it was the most normal thing in the world. She knew the drill, followed after our escort, and held my hand the whole time, which was reassuring. She wasn't shy about chatting with me whenever we had some privacy, and her air of nonchalance about the whole situation helped put me at ease.

Still, it was obvious Adrienne was going out of her way to avoid identification, even more so because of the minor media storm that had erupted after our May 6th adventures. So whenever we were within view of the public, she didn't talk to me and her gaze remained fixed forward with a business-like expression. Even aboard the plane and buckled into her seat, she didn't remove the cap or sunglasses. Cognizant of the passengers around us within earshot, we didn't speak much either. And despite the comparative luxury of sitting First Class instead of back with all the rest of the cattle, in that moment I felt nothing but sorry for my dearly beloved "sister" having to jump through all these hoops every time she wanted to fly somewhere.

Takeoff was uneventful, and once the plane leveled out the main lights were turned off to let people sleep during our red-eye flight. The Captain also turned off the seatbelt sign, and our flight attendant arrived to take our drink orders. But rather than lean over me from the aisle, the pretty brunette with light brown eyes slid between the bulkhead and our seats and crouched down. "Hey A.D.," she greeted warmly with a broad smile for my traveling companion. "It's been a while since I last saw you on this route."

Smiling back and removing her sunglasses, Adrienne nodded and replied, "Hey Shalane. Yeah, long time no see. I wanted to spend more time with my boyfriend here. Ben, Shalane ... Shalane, Ben."

"Ah, the infamous Ben! Very pleased to meet you." The flight attendant shook my hand and gave me a beaming smile. "A.D. has told me so much about you."

I blinked in surprise. "Oh she has, has she?"

Shalane chuckled warmly. "Oh, yeah. It's always 'Ben-this' and 'Ben-that'. Always so excited to see you when she's flying into SFO and dreamily nostalgic when she's flying out. I worked her flight after Valentine's Day last year, back before she was quite so famous. The whole flight she gave us the lurid details about the night she spent with you and completely forgot to mention her first appearance in the Sports Illustrated Swimsuit Edition. Biggest break of her career and all she could talk about was you."

I smirked and glanced over at Adrienne, who was shaking her head and blushing a bit as she stared out the window. It was quite rare to see her embarrassed, but I didn't tease her. I knew how important I was to her, and how important she was to me, despite our lack of formal boyfriend/girlfriend titles. It didn't surprise me that she'd tell these flight attendants about me, and even though we now maintained an even closer 'sibling' relationship, I knew that for the next week or so I'd have to get used to the idea of people seeing us as boyfriend and girlfriend. So I simply reached out and squeezed my 'girlfriend's' hand as I replied, "Yeah well I always missed her, too."

Shalane smiled at us and looked back at Adrienne, asking, "Your usual?"

Adrienne sat up. "No, actually. Just a ginger ale for me."

Shalane looked perplexed. "A ginger ale? For you?"

Adrienne shrugged. "Yeah, I'm good. But mix Ben up a Manhattan."

I arched an eyebrow at her.

Adrienne grinned. "Never had a First Class flight before? Drinks are free. Enjoy it and mellow out, huh?"

"Then what about you?"

"Believe me. I've had plenty of cocktails aboard these flying tin cans."

Shalane chuckled. "That she has, but not tonight. One ginger ale, one Manhattan: coming right up."

After bringing us our drinks, Shalane went about taking care of her other First and Business Class passengers. After she left, I took a sip of my Manhattan and quietly asked Adrienne about her apparent familiarity with our flight attendant. Adrienne explained that she'd made friends with most of the regular flight attendants who handled her frequent trips, and they usually went out of their way to help shield her from unwanted attention. Some of them had come and gone, moving on to different routes while others took their place. But Shalane was someone she'd first met two years ago and been seeing off and on ever since.

Leaning close, I had to ask, "So have you and her ever met up outside of an airplane?"

Adrienne smiled at my innuendo. "Yes, but not like you might think. I've hung out with her and a few other flight attendant girlfriends in New York, but Shalane's 100% straight."

I held up my cocktail. "She seemed surprised you got a non-alcoholic soda."

Adrienne shrugged. "I usually have a couple of drinks on these flights, partially to pass the time with a nice buzz instead of just feeling lonely and dreaming of you."

I frowned. "Has it really been so bad? I find it hard to believe you'd ever feel lonely if you didn't want to be. Surely you can pick up a conversation quite easily, even on a plane."

She shook her head. "First Class passengers are either businessmen or rich couples, and I can't get seated with a couple. I get hit on too much when I have a seatmate, so I usually pick that middle seat over there." Adrienne gestured past me to the solitary First Class seat in this 2-1-2 configuration. "Then I either keep to myself or chat with the flight attendants, like Shalane. They usually let me hang out in the crew area with them on daytime flights. I just sleep if it's a red-eye like tonight."

I nodded. "Speaking of which, we should get some rest ourselves, huh? It's already what, almost 2 in the morning in New York?"

Adrienne grinned at me. "We will, of course. But not just yet. Tell me you haven't seriously thought about the opportunity here."

I frowned, not yet understanding. "Opportunity?"

"You and me ... on an airplane ... a certain club that only admits members at a certain elevation above the ground?"

I blushed and took a rather big gulp of my Manhattan. Glancing around a little nervously, I muttered, "Do people really DO that? Of course you hear the stories, but it seems awfully hard to not get noticed, you know? Aren't we supposed to be keeping a low profile? The media would have a field day if we got caught. There's only one lavatory up front. And people are bound to notice that two seats are empty at the same time."

"Everyone'll be asleep. Nobody's gonna notice."

"The flight attendants will surely notice."

"Of course they will, but they'll also help us out. None of those women are going to judge me, and it's not as hard as you'd think to avoid getting noticed by everyone else. Most everyone in this cabin is going to be unconscious in another half-hour, and even if this ends up on Celebrity Sightings, sex sells. C'mon, Tiger, I wanna join the Mile High Club. It's my first chance."

I arched an eyebrow and narrowed my eyes. "Your first chance? Somehow I rather doubt that. Even if not with Shalane, you're talking like you've already pulled this off before."

Adrienne blushed and looked away for a moment. "Well ... my first chance with a guy, alright?"

I sighed, but Adrienne had already slipped a hand into my pants and wrapped her cool fingers around my half-erect rod. Though I was nervous about the whole thing, any opportunity to have sex with Adrienne was quite arousing to begin with. And the idea of joining the Mile High Club made it even more exciting. "So how do we do this?"

Adrienne beamed. "Trust me."

"This is crazy," I muttered.

"Shut up and stay quiet," Adrienne shot right back as she gripped my shaft in her right hand, swabbed my mushroom head through her vaginal cleft, and slowly leaned her weight back to sit down in my lap and impale herself on my upright cock for the second time tonight.

That's right, I said second time.

The first time had been while taking the traditional path to getting membership in the Mile High Club: in the aircraft lavatory. Adrienne had gotten up first, chatted in the galley area with Shalane and the other First Class flight attendant until the businessman occupying the lavatory exited, and then she went in and locked the door.

Once she was inside, Shalane closed the curtain at the end of the B/D aisle, which was both my signal to get up and an extra deterrent to another passenger interrupting us. So I chugged what remained of my Manhattan for liquid courage, went through the galley to the other side of the plane, and knocked on the lavatory door, muttering, "It's me."

Adrienne popped the door open, looked over my shoulder to wink at Shalane behind me, and jerked me inside by my collar.

Our Mile High initiation had been fast, with no foreplay needed and neither of us delaying our orgasms. Adrienne was already soaking wet in anticipation, and she bent over and stuck her ass back at me while I locked the lavatory door. It was an easy matter to lift her skirt and pull aside the strap of her panties, and I shoved my dick into her from behind within fifteen seconds of closing the door.

Adrienne came quickly. The naughtiness of the situation and the mental high of fucking at thirty-two thousand feet had her primed to blow even before I entered her. And within two minutes of aggressive thrusting plus my hands pawing at her massive tits, Adrienne's whole body shuddered in a climax so intense that she had to clamp a hand over her mouth to stifle a scream that Shalane could probably still hear from outside.

I didn't take much longer. I had no interest in prolonging this fuck any more than I had to, so I hammered my pelvis against Adrienne's ass as fast as I could while relaxing my PC muscles to simply let them go. And about a minute after Adrienne had screamed, I grunted that I was about to cum as well.

Standing up straight, Adrienne pulled her pussy off my prick and spun around. Sitting down on the closed toilet lid, she grabbed my ass and swallowed my schlong straight into the back of her throat. When she looked up at me with her golden irises aflame, I knew exactly what she wanted. So I grabbed her head and face-fucked the shit out of her until I felt my balls uncoil and begin spraying their load straight down her gullet.

My girlfriend teared up a little but smiled while feeling the little impacts of sperm against her throat. She swallowed everything I had to give her before pulling back and gasping for air. I patted her head and tucked myself away. And then I left the lavatory first, returning to my seat to let Adrienne check on her makeup in the mirror.

Our initiation into the Mile High Club had been satisfactory, if not spectacular. We'd certainly had better sex sessions, and fucked each other in crazier places than this. Still, it was nice to cross "an aircraft lavatory" off the bucket list, and I reclined my plush First Class seat intent on getting at least a few hours of sleep before landing in New York.

But Adrienne wasn't satisfied. Sure, she'd gotten her first male-female Mile High fuck out of the way, and even had a decent orgasm despite the hurry, but she was still horny and keyed up when she returned to her seat. I talked her into getting an Appletini to calm her down a bit, and for a little while the drink seemed to do the trick. But sometime later, I'd woken up to find Adrienne's hand digging in my pants to wrap her fingers around my cock once again.

Groggy, I'd wondered what she was doing. Two minutes later, I found myself sitting upright in her window seat furthest from the aisle, muttering about how crazy this was while she told me to shut up. She sat in my lap facing away from me and swabbed my mushroom head through her vaginal cleft. Having cum once before, not to mention the nervousness of doing this in the First Class cabin with a bunch of other people all around us, I was having a little trouble staying erect. But before I could lose the stiffness from my shaft, Adrienne fully sat down, and once surrounded by warm wet pussy walls, my pencil filled with lead once more.

"If the people behind us are still awake..." I muttered quietly from right behind Adrienne's ear.

"They're not. I checked," she whispered back, clenching her inner muscles around my rod. "Everyone's asleep."

I sighed and weighed the situation. Although these First Class chairs were big, they weren't tall enough to obscure the fact that a 5'10" woman was sitting in my lap. The First Class cabin only had the two rows before a partition separated us from Business Class, so there were only eight other people to really worry about. Of course, the flight attendants were still awake and I noticed Shalane and Amanda, the other flight attendant, both giggling as they peeked around the corner. The fact that their attention was on us reassured me that everyone else indeed was asleep. Still, I could only imagine what kind of scandalous headlines this would produce if somebody woke up and snapped a picture of us.

Of course, it wouldn't make for much of a picture. Sure, Adrienne was sitting in my lap, but our torsos were covered by a blanket and she wasn't moving much. A photo of us in this position could be explained away as merely cuddling, and with that idea in mind I surrendered myself to what was going on and started rocking my hips to make short thrusts into my lover's snatch from below.

"Ooh, that's it..." Adrienne whispered. Planting her hands on the armrests, she gyrated her body in my lap, fucking me in a horizontal circle rather than up and down. Leaning back against my chest, she sighed and turned her head to kiss me. And throwing my last vestiges of caution to the wind, I kissed her back and put more energy into my fucking.

Neither of us was in a hurry anymore. The feeling of being trapped in a lavatory with no idea how long it might be before somebody came knocking had put a sense of urgency into both of us. But rather than feel exposed out here in the open cabin, I felt like we would have ample warning before somebody interrupted us.

"Fuck me..." Adrienne whispered between kisses, and I counted on the droning engines to wash out her voice in a haze of white noise. "Fuck me, Tiger..."

I fucked her. Pressing my feet down into the floor, I started bucking my hips off the chair with more and more power. Her body got bounced up and down a bit, forcing her head to bob above the chair's backrest rather suspiciously should anyone behind us crack their eyes open. The harder I fucked her the more she kept moaning. And when I slipped my hands beneath the hem of her sweater and palmed her big 36F tits from inside her bra, Adrienne let her head fall back over my shoulder as she gasped in erotic bliss.

"Mmm ... Nnngh ... Uhhhnngg..." she moaned a little more audibly after some particularly forceful thrusts. I pulled my left hand out of her sweater and clamped it over her mouth to muffle her moans.

"Mmff ... Nnfff ... Hmmfff..." she moaned into my palm instead.

"Hmph! Ngggh! Eeegghfff!" she squeaked when I pulled my right hand out of her sweater and reached down to buzz her clit.

"Ffffk! Nggghhff! Umm! Cmmeenggff!!!" she squealed as I masturbated her to a climax, her whole body shuddering as she tried to fight it off before her back suddenly jerked against my chest and she tried to straighten out her entire body at the same time. Adrienne's legs shot out in front of her and the back of her head slammed against the top of the chair. And her pelvis thrust forward so hard that she would have popped off my prick if I hadn't been pinning her crotch against me with my right hand.

As it was, her sudden jerk pulled my butt off the chair with her, but moments later we crashed back down onto the seat, and I resumed strumming her clit back and forth while she literally bit down on my left hand to stifle her scream.

The sudden pain shooting down my left hand was enough to stop my ejaculation cold in its tracks. I bit down on my lower lip to stifle my own exclamation of pain, lest I wake up everyone in the cabin. But while I grimaced and tried to fight off the stinging bolts shooting down my left forearm, I kept strumming with my right hand until Adrienne's orgasm passed and she went limp in my arms.

With her massive tits rapidly rising and falling as she gasped for air, Adrienne slumped against my chest and whimpered pitifully. I pulled my bitten left hand away from her mouth and took some deep breaths of my own, fighting to let my lungs expand against her body's weight pressing down against my pecs. And I relaxed to catch my breath while my lover came down from her orgasmic high.

Eventually, Adrienne recovered enough to sit up a little straighter. Still seated in my lap, she turned her head back to kiss me with a grin. But only a second after our lips met, she pulled her head back and gave her hips an experimental wriggle. "Didn't you cum?" she whispered, apparently feeling my rock hard erection still buried inside her.

I shook my head. "Was about to, but kinda lost it when you bit down on my hand."

Adrienne's eyebrows canted to the sides and she frowned at me apologetically. First, she felt my hand with her fingertip and snickered at the obvious teeth marks running in a semi-circle along the length of my index finger. Then, she kissed me again and whispered, "I'll make it up to you right now."

Not understanding, I arched an eyebrow. But Adrienne peeked over the backrest to make sure the couple behind us were still asleep, and focusing forward again she raised herself into a half-squat to pull off my prick before grabbing it in her right hand and recentering my mushroom head at a different entrance.

"You sure about this?" I asked quietly while she tried to sit her asshole down on my cock.

"How many people can say they've sodomized a supermodel in the First Class cabin of an airplane?"

"You're not lubed and this is dangerous enough as it is."

"Your cock is soaking wet and I'm just horny enough to do this right now," she muttered back, gasping as my head popped through her sphincter.

"Unngh," I grunted, letting my head fall back against the chair as her hot anal chute swallowed up my cock. It took a little while, but eventually Adrienne had me balls deep in her rectum and once again she reclined against my chest while soaking in the sensations.

"Fuck me," I grunted, this time content to sit back and let her do all the work. "Fuck me with your tight, dry asshole."

"Fuck yeah," she muttered, planting her feet on the floor and her hands on the armrests to leverage herself up a few inches before sitting back down.

"Fuck me, baby. Fuck your ass on me in this First Class cabin. Isn't this naughty?" I whispered.

"Fuck yeah, Tiger..." she moaned, rising and falling a little faster.

"Fuck me while Shalane and Amanda watch us. They have no idea I'm up your ass right now. How naughty is that? How delicious is our little secret? What kind of slut would they think you are if they knew you were letting me sodomize you in seat 2J?"

"Fuck yeah, Tiger..." she moaned again, her energy increasing the more I said.

"Fuck me with your slutty asshole. Clench your winking anus around my shaft and hump your fully-clothed body up and down my cock while all these people sleep around us. How crazy would it be if they all woke up, huh? Would you want to stop? Or would you want to keep going? Can you imagine the way their jaws would drop if they found out you had eight inches of cock up your ass right now? The astonishment ... the arousal ... the envy ... Feel my cock up your asshole, baby. MY cock. No one else's."

"Your cock. My one and only cock. Fuck me, Tiger. Ram that gorgeous dick up my ass and fill my rectal cavity with your sperm. Only yours. No one else's. Let them be envious. Let them all dream about being inside me when it'll only ever be you. Fuck me, Tiger. Fuck me and fill me with your love. Fuckme, fuckme, fuckmeeeeeee-MMPH!"

Her last word cut off when I clamped my hand over her mouth. While I'd managed to growl right into Adrienne's ear in a low, whispered voice, by the time she got to her final "fuckme's" she'd practically been speaking aloud. Bitten once or not, I kept my left palm on top of her mouth and reached down to rub her clit once again with my right hand. And as I felt my balls boiling once again to release my load, I strummed her clit every bit as hard and as fast as I'd done the first time.

"Cum for me, my Tigress. Cum on my cock and squeeze out my jizz. Clamp that sphincter around my shaft and force me to erupt deep within your bowels. Fuck me, baby. Cum for me. I want to watch Shalane's and Amanda's faces when they see you climax again. I want to see the devious delight in their eyes when they recognize you're orgasming again. C'mon now, Adrienne. Cum for me ... right... now."

"HMMPHHH!!!" Adrienne bucked and screamed into my palm, louder than ever. If anyone behind us was awake, there was no WAY they'd miss that. But I'd ceased to care long ago. I didn't give a rat's ass if anyone knew I was sodomizing Adrienne in seat 2J of a commercial airliner. What, a guy like me was supposed to be ashamed of that fact? Gone were the nerves or sense of embarrassment I'd felt in the lavatory the first time we inducted ourselves into the Mile High Club. Gone was any sense of urgency to get things over with before we got caught. Maybe I wasn't going out of my way to announce what we were doing, but neither was I going to try any harder to hide it. Feeling Adrienne's anal muscles spasming around my ass-imbedded schlong, I thrust myself upward with her and let go with both balls, firing my wad of scalding hot spunk straight up to where the sun would never shine.

"HNNGH!" I grunted as I fired a second load.

"HNNGH!" I grunted again.

"Hnnngggghhh..." I grunted one more time, clenching my abs and squeezing out every drop I could before letting my body relax and slump back down into my seat.

Adrienne had stopped screaming, so I removed my left hand from her mouth and brought both hands back under her sweater so that I could palm both tits skin-to-skin. Squeezing her mammaries simply for the fun of it, I sighed and relaxed in my own post-orgasmic bliss. And I smiled when she finally caught her breath enough to turn and look back at me.

"Fuck that was awesome..." she mumbled. "What got into you at the end there?"

"You inspired me," I replied with a smirk.

"I love you, Tiger."

"I love you too, my Tigress."

Adrienne giggled. "That's the second time you called me that."

"Don't like it?"

"No, no. I love it. Makes me feel like ... like I'm yours." She sighed and leaned back against my chest, letting her head loll over the top of my shoulder.

At the warmth in her voice, I squeezed her extra tight. But then I thought about all the talks we'd had over the years about the importance of Adrienne maintaining her independence and me never trying to tie her down, especially after the near-disaster of me giving her the promise ring she currently wore on her right fourth finger. So I quickly released her, took a deep breath, and muttered apologetically, "You know, I never want you to feel that way. You're not 'mine'; you're not a possession. You're not even my girlfriend, and you have no obligations to me whatsoever. I'll love you forever, but I'm not trying to keep you caged."

Sitting up straight and clenching her asshole around my still-embedded cock, Adrienne turned with a light head-shake and a warm smile that said I didn't understand. After kissing me again, she pulled away, set her forehead against mine, and murmured, "I happen to love feeling like I'm 'yours'. Because I already am. Forever and always, Tiger. Forever and Always."

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