Mile High Club Adventure

Story Info
Young girl and older man join the exclusive mile high club.
7.1k words
4.51
58.9k
18
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
RobynG
RobynG
376 Followers

K. Linford Little is nothing if not adventurous.

Maybe it's the fact he loves scuba diving, sky diving and muff diving, not in that order.

Ok, that was a rash attempt at getting a laugh, but it is true. "Lin" is a very adventurous 50-something guy. He's married with a couple kids, enjoys adventure vacations that always include at least one activity he's never tried before.

For instance, last year in Aruba he attempted kite surfing. He didn't get the knack for it, but he enjoyed himself immensely.

He works long hours at his job, an executive with an insurance company. I know, because I used to be his administrative assistant. He works hard and plays hard, I know, because I'm his, well, girlfriend.

We've been together so to speak for more than a decade, finding the time for companionship, love and romance, some all in the same day.

Oh, and his wife doesn't know and he prefers to kept it our own little secret that we have this thing going on.

For me, I know it's wrong, but I love him in my own way. I mean, over the years I've dated several guys, a couple very, very seriously. Once I was engaged, but that wasn't to be. Thank goodness I came to my senses before we tied the knot because it would have been a disaster.

These days I am dating a very nice man, Robert, who is in mid-management and who seems to have a lot on the ball. We go to the theater, concerts and eat at nice restaurants. We like long walks on the beach near his parent's shore house, and once or twice a week we make love. Robert is a great guy, I love him in my own way, and who knows where the relationship will lead.

Yet in my world there is a parallel world that includes my former boss. I learned long ago he's never going to leave his wife....which is why we broke up years ago. But we got back together because there was a certain "it" between us that couldn't be satisfied elsewhere.

We know it's wrong, cheating on our spouse/boyfriend, but it's reality. What can I say but to everyone I'm sorry but it is what it is.

Lin is very special to me, he is in my DNA, he's the smile on the clown's face, the sun in the morning and everything in between. We've had our ups and downs, but we always manage to make things right and find the time to share a piece of our lives together.

Oh, and have I mentioned he loves blow jobs?

Yea, he's a guy and yes he does. His wife doesn't believe in giving them any more. Oh they have sex, he admits to that. Every once in a while she will suck him hard, but that's it in the blow job department at home for the guy. For full service, crinkle your toes and turn to putty in one's hand blow jobs he finds be always ready, willing and able.

We've done it a jillion times in his car, in parks, parking lots and behind hedges. We've done it at his club, in the men's locker room late at night (almost caught) and in the balcony of a movie theater. I think I've mentioned that Lin is adventurous.

There is just something about sucking the guy. I love it. He says I am addicted to his cock and maybe I am. I just like the power I have over him, the way he groans and moans, the way he enjoys himself at my touch.

It has been years since we had intercourse. That doesn't mean we are celibate. Besides oral sex he's done a little bit of everything with me.

It's funny, he's honest about it. He might suggest something to his wife who will nix the thought, and within a week I'm her stand in. I mean, I've flashed a trucker for him (both my tits and ass), I've let him do me with a vibrator and, well, a banana. I've dressed up in schoolgirl outfits and even a maid uniform.

Believe it or not, I love doing it.

We've nearly been caught in some of our escapades, and have actually been caught in others. When you blow a guy in a parked car there's always a chance someone will catch you in the act. We've been caught in the car (check out some of my other reports) but we've also been observed when we've ventured outdoors.

The walk along the railroad tracks near the canal has been especially problematic, as I was observed on my haunches giving Lin a blow job when a train passed (the engineer saw us for sure, Lin reported, and I am sure some passengers) but also near that same stop we were observed fingering each other while leaning against a tree (and a guy walking his dog came within 10 feet of us, seeing everything including my skirt up and Lin's fingers in my pussy).

Luckily we've never drawn the attention of the "authorities" so no harm, no foul, right?

Lin has lots of quirks besides a proclivity off exhibitionism! As mentioned, hardly a date doesn't go by without me blowing him. He likes short skirts, and loves it when I wear stockings (not pantyhose). His wife wears pantyhose, he says. And while I normally don't wear stockings, I do for him.

Years ago after our first go around we stopped having intercourse. When we were seeing each other at work we'd always be doing it somewhere. We had sex on his desk in his office, of course, but also in the conference room and once in the copy room over the copier. We'd do it in his car and several No Tell Motels.

But all that ended when we broke up. I realized he wasn't leaving his wife and at the time I thought it was time to move on. It was after months and- months of regret though that we got back together.

The thing is, at that point, we both knew what was in the cards. We were never going to be married, a formal couple, and some things did change. The biggest was that we stopped having sex. No intercourse. In retrospect I think in his mind he followed the Bill Clinton rule: no intercourse means you aren't cheating.

You know, I didn't really miss it. I had all the sex I wanted when I blew him. For years now that has been a wonderful, wild ride. And various boyfriends and I have consummated our relationship between the sheets, so it's not like I wasn't having intercourse.

So why am I telling you all this? If you've read my stories, you know all that. If you haven't, feel free to do so. Or just read on if you aren't worried about context.

On a recent Saturday Lin was a bachelor as his wife was at her mother's for the weekend. We drove to the Pennsylvania Amish Country and went antiquing for the day, much less excitement than his normal adventurous self.

While driving there he had me flash several truckers while jerking him off. On the way home he pulled over at a rest stop and had me blow him. Yes, we went antique store hopping for me but he really enjoyed himself going and coming and coming (pun intended).

We stopped for dinner at a hole in the wall diner and had a great meal. How is it these diners offer a complete menu all day, and do it well? Steak in the morning is as good as ham and eggs at night. Good food and cheaper than the specialized places down the road.

Small talk was made, especially with a little flirting on each of our parts. We enjoyed all the time we had together, and it was even better when we didn't have to hurry him home. We talked about this and that when he mentioned he was flying to Chicago the next week.

I said something about being careful with the Flight Attendants who might want to have him join the Mile High Club, something that brought an immediate smile to his lips.

"What," I questioned.

"That's a fantasy of mine, but, no, I don't think the airline would appreciate it. My luck would have someone walk in on us."

For the rest of the meal we spoke in hushed tones on how much we enjoyed making fantasies reality, but couldn't figure away to join The Club. Too difficult, too dangerous and so forth.

Several weeks went my before the topic came up again, and this time it was Lin had not only thought about but researched.

"Hey Robyn, did you know there are some places where you can actually take a Mile High Club flight?" said my guy over a latte. "Seriously, I saw it in the internet."

Shaking my head, I reminded him that not everything on the internet should be taken as gospel.

"No, seriously, there's a web site I found and there are a handful of places that offer "private" flights," said my former boss.

Lin was quick to say that you can't find these flights just anywhere. Really? No kidding?

He relayed what he found out. The flights are on small planes, the Piper Cherokee is popular, they are based at regional airports, and generally the flights are an hour or so at the 6,000 foot level and generally only take off in good weather. If a storm is a coming, you don't go. Finally, the flights are generally over countryside and within a 30 mile radius of the airport.

"Oh, great, and we'd be watched by the pervert pilot the whole time and our trip would go out on the internet that night," I said, shaking my head again. "So, you want your wife seeing you in action up in the air?"

Lin was quick to say in his "research" all talked about privacy and that the flights wouldn't continue unless there was discretion. "I talked to a guy down south who said his job was to fly safely, and that was it. What we did in the back behind the curtain was our business. He was very nice about it, didn't sound like a creep."

Lin then gave me the bad news. "Only problem is that the places that I saw the flights were in the South, the Midwest and in England. There were none advertised close to here."

Good thing, I thought. But then I couldn't get the thought out of my mind for the next week. I wondered what it would be like, frolicking a mile, two or three in the air with the guy I loved. It presented quite a fantasy. I had to admit that joining the exclusive Mile High Club was quite enticing. It would be safe, legitimate and sounded like a lot of fun.

"Darn, you had me there saying yes, and there is nothing to say yes to," I lamented. "But it's a great idea, a wonderful fantasy."

It really did sound hot. Much hotter than Kathy and her husband's little bit of action she embarrassingly mentioned at lunch. They stopped on the way home from the department Christmas party and did "it" in the backseat of the car.

They had finished and had gotten buttoned up and all when a Good Samaritan had stopped to see if they needed any help. For Kathy, nearly being caught in the act was hot. For Lin and I, well, we had fooled around in the car and had actually been observed on several occasions! No, the Mile High Club was quite exciting to me.

For his part, Lin worked it into our sessions in the car. He'd pretend I was a flight attendant serving him "Uh, miss, could you take care of this spill on my pants?" or tell me the pilot was watching as I sucked him off down by the river.

The guy could make a fantasy out of nearly anything.

# # # # # # # # #

Several weeks passed and Lin and I played out our Mile High fantasy a couple times, only at 15 or 16 foot level!

On one occasion I gave him a blow job in the bedroom of a show house in a new development while the real estate person was on the floor below. I'd be happily performing on him and he'd whisper how we had to hurry before the flight attendant knocked on the door. We hoped the intercom on the wall wasn't working yet!

It was quite erotic and very hot for me. I love his imagination. It's endless, like looking from a pier to the ocean. He always was so imaginative in his ways of finding erotic possibilities.

I was waiting at the hair dresser when he called. "Hey, guess what? I found us a plane and a pilot."

At first I was lost, then smiled as he relayed the story.

One of the places down south had replied to an email about someone they knew who flew out of one of the South Jersey regional airports, like Ocean City, Millville or Woodbine. These were general aviation airports, without a tower and without lots of wandering eyes. Just a bunch of small aircraft enthusiasts.

Lin's contact knew someone who flew out of one of these airports, the name of which will remain nameless to protect their license. The guy had done a number of these "Mile High Flights" but only on a referral basis. We had a referral!

"We can do it Saturday afternoon," exclaimed an excited Lin. "That is, if you still want to."

I was nervous, and I have to admit we spoke for about an hour before I agreed. I mean, it would involve sex, the horizontal kind, to make it real. That was a lot different than my mouth on his dick. We'd be screwing, and it had been years since we'd done the deed.

"You remember how, right Robyn?"

What a jerk! "Of course, I just wondered if you could last for an hour and get what we paid for," I verbally grappled back at him.

Ultimately I said yes. Lin gets what he wants, and I thought it would be quite fun an exciting. With that a plan was hatched.

We spoke several times over the next couple days about the flight. Lin was very busy at week and at home, and he was cautious about being away worried that his wife might wonder what he was up to. Sometimes in these situations I'd meet him on the way home for a quick snuggling, but he didn't want to let his guard down.

"Sometimes I think she thinks I'm seeing someone," Lin related. "So whenever I get that feeling it's better safe than sorry."

As long as Saturday wasn't impacted, I was cool with his cautious behavior. I actually liked his wife a lot, had babysat for them in the past, and actually enjoyed her. It's just that I enjoyed her husband a whole lot more.

It was a whirlwind week. The thought of joining the Mile High Club caused me to bring out "Rocket Roger" for a date. The hard fake cock was always there when I needed!

It probably sounds bad, but when my boyfriend came over Friday night expecting to stay overnight, I feigned an early morning conflict. He was disappointed, especially after springing for dinner, but that disappointment turned around when we made love back at the house. Still, I have to admit I fantasized about the next day's activities while he was rutting me from behind. I think he wondered what had gotten into me when I came twice while he banged me and then turned around quickly and let him shoot in my mouth.

It's funny, as much as I love to suck Lin off my current boyfriend left a little to be desired when I sucked him. He loved it, but he always held my head tight in his hands and sort of face fucked me. There's a time and place for everything but his force was a turn off.

Long story short, we had a good night and his rocks were socked royally before he left.

In the morning I woke with a smile, thinking of the day and wondering what and how things would happen. Anticipation. Excitement. Would the pilot be a jerk, would people know what we were there for (how couldn't they?). Still, it was going to be a great day.

Thinking about the day's activities I selected a demure blue blouse and skirt ensemble, little black boots and little jewelry to get stuck on things. Cute, but not too obvious as to what we might be doing. I had thoughts of walking into the airport and having everyone point at "The Slut." Or maybe I'd arrive wearing a long overcoat and nothing else. Nope, just a little sightseeing rides so to speak.

We parked in the back of the Circle Diner and met inside. I had a cereal, fruit and yogurt platter while Lin munched down his usual two eggs, over medium, with French fries (instead of hash browns), with both of us adding coffee to our culinary delight.

We caught up with our week. It was unusual for us to go several days without seeing each other, and some things just don't make their way to conversation on the phone. Our schedule had us meeting our pilot at 12:30, so we had plenty of time.

"So, are you excited?" I asked. "What a fantasy, right?"

"You bet, Robyn," said my former boss. "This is very hot. I've been thinking of this for days."

He related that it would be safe, the pilot discrete, and the activities, well, hot. "I am so horny for you. I'd stop along the way to the airport but don't want to wear myself out."

Cute, but what he really meant was that if we stopped I'd blow him, and if he came then he'd probably be shot for the day. Age had slowed him a bit, and while the little blue pills helped keep him hard they couldn't get him numerous orgasms in a short time.

We had a 30 minute drive to the airport. We took Lin's car, leaving mine behind the diner, and I had some fun on the drive stroking Lin's thigh and every once in a while feeling his hard cock.

A few minutes from the airport I asked Lin what would happen once got to the hangar.

"They are expecting us, sweetie, they said there could be other pilots and passengers around but that we wouldn't stand out. We're just going for a sightseeing flight on a nice afternoon."

We pulled in and parked, with Lin bringing his camera to give the idea we were sightseers. We walked inside the Spartan office where a guy pointed down a hallway toward some desks and offices, identifying a tall lumberjack of a man sitting in the back.

Lin led the way and introduced himself. "Hi, we're the Smiths," said my former boss.

"I'm Trevor, and I will be your pilot today...thanks for setting up an appointment!" said the dark-haired man aged about 35. "It's a great day for flying and sightseeing."

With that he called out and a woman appeared from one of the offices. "Oh hi," said the girl, introducing herself as Melody. "Nice to meet you. It's a great day for flying!"

They were cut from the same mold. I pictured them as boyfriend and girlfriend, but wasn't sure. Neither was wearing a ring, but then, neither was I. Lin, of course, had his on, so there might have been some question about our relationship.

The guys headed out to the tarmac and the Piper while Melody took me to the back to lock up my purse. In the room she smiled and asked if I was excited.

"Uh, a little nervous...haven't been in a small plane in years."

"You are in for a treat, and it's going to be a great time," said the girl with a knowing smile. "Trevor is a great pilot, the best. Hey, I know what you guys are here for, don't worry, nobody will know but us and it is quite exciting."

Looking at her, it was my turn to smile. "Have you ...."

"Oh yes, I'm in the club. I've been a member for several years and have re-upped that membership several times," she smiled. "I have to admit it was embarrassing the first time Trevor and I did it. There was another pilot, he's since moved to Indiana, that drove the bus out there. We all worked together here, and it was embarrassing being in the back until I just put it out of my mind."

We spoke for a couple minutes before I had to ask "the" question. "Do they, you know, the pilots, look..."

Melody smiled and said, "Only if you want them too! There's a curtain for privacy. But Trevor is very discrete. He will keep his eyes forward unless you want him to look. But if he does he will have to deal with me! But...."

"But..." I asked.

She smiled. "You're cute, and he's mine, and I know you don't have designs on him. But I bet it would be a turn on if you thought he might look."

I simply nodded my head yes.

"Then leave the curtain open a little or as much as you want. It's okay. He's very professional and he knows how important his job is. But if you don't mind him taking a glance, leave it open a little. And if you want some extra time...."

"Extra time? What do you mean?"

"Okay, nobody has to know but you and me, and I guess your boyfriend and Trevor actually....but if you find yourself needing a little more time at the end of your trip to, uh, finish anything, you could stick your head up front through the curtain....you know, talk to him nicely. Maybe flash those boobies at him. I am sure he'd give you a few more minutes. I will set it up if you need it, okay?"

Nodding, I thought that might be hot. Who knows? "You're okay with that, him looking I mean?"

Melody smiled at me. "Are you kidding? You flash him and he will be all over me tonight. Not that he needs much inspiration. But you know, a little play acting never hurts."

RobynG
RobynG
376 Followers
12