I Join The Mile High Club

This story follows "The Perks of Flying First Class."

This is an adult sex story.

Everyone in this story is an adult, over the age of 21.

Please enjoy and thanks for the views and the votes.

****

I was on a private jet heading from Seattle to Burbank Airport (Los Angeles).

It was Thursday just after noon. It was the second week in January.

There was one other passenger on board, so I guess you could technically say it was "we were on board."

"We" is me, Jack Colton and Missy Rogers.

Ms. Rogers was not my wife, nor my girlfriend.

But she had just finished blowing me, swallowing my load with a smile and relish, and with the full blessing of my wife, Catherine.

Catherine had given me a hall pass the day before, but the hall pass was set to expire when the plane touched down.

If you haven't seen the movie Hall Pass, you should.

So I was trying to make the most of my first hall pass; get in as much ass as possible with this beautiful creature before the cutoff time.

Missy was born and raised in Seattle.

A U of W grad with a BA in marketing.

Just turned 32.

5'4" in stockings.

In fuck me heels, 5'8".

She was recently divorced.

No kids.

She was very attractive.

All natural breasts, more than a healthy handful in size and they were surprisingly firm and her nipples were highly responsive.

She had a small frame, thin back; nice tight ass (recently penetrated); great legs and a very pretty face.

Red hair, and the carpet matched the drapes. Same shade, up and down.

She enjoyed it when I spent time cleaning her drapes with my lips and tongue.

I liked her squirming under my oral assault.

She hadn't had her pussy eaten in months and she was very grateful.

Oh so grateful.

If you've read my other stories you know how much I enjoy spending time between the thighs of my female friends.

Men can earn lots of points for eating pussy.

There would be far fewer divorces if more men made a regular habit out of it.

Get over the smell, the hair, the discharge and focus on being the best pussy eater the woman you're licking has ever had and you'll be treated like a king.

Back to the very grateful Missy Woods ...

She was smart and funny.

I'd put Missy into the category of on the border of being sassy.

So sassy I think she was pushing to be spanked.

I think I'd like doing that.

Missy had a body to die for; firm where it should be firm and soft where you wanted it to be soft.

No tattoos anywhere and her piercings were limited to her earlobes.

I couldn't keep my hands off of her.

She loved the attention and I loved having my hands on her.

And I was all over her.

Ms. Rogers was a business associate; I had retained her firm to do advertising, public relations, and social media about two months prior.

Her firm would be handling the Seattle market initially but I had been thinking about bank rolling her so that she could have offices in the cities where my company had its car dealerships and hotels. Places like Los Angeles, Las Vegas, and Scottsdale (Phoenix).

I needed people to handle advertising, public relations and other marketing related stuff in each market because each market was different.

Seattle isn't Phoenix and nothing on the planet is like LA or Las Vegas.

I hadn't told her about these expansion plans just yet, but I am sure she would be agreeable; she was an astute business woman who had potential. And drive.

She just needed the opportunity and the financing. I had both of those to give her.

Ms. Rogers was also the hottest sex partner I had ever been with.

I'd been with, slept with, more than fifty women since my first wife died in an automobile accident just under a year ago.

My first wife was an elementary school teacher on her way home from work one afternoon and was t-boned by a drunk driver barreling through an intersection.

She was killed instantly.

I remarried about nine months later.

Catherine was a very good friend of my wife.

Catherine was now home, pregnant with our first child.

She couldn't travel on this specific trip with me so she gave me a hall pass.

It was an unexpected gift.

What a wife! I have to be the luckiest husband on the planet.

Missy and I had been instantly attracted to one another the first time our eyes met.

So when the opportunity surfaced to have sex, we did.

Vigorously.

Missy and I fucked for the first time last night.

And we fucked all night long.

Just by being naked with her she gave me a hard on that did not go away.

She had a very tight, very wet, very hot pussy.

Her groans of pleasure as I entered her and pushed my way in deep were music to my ears.

It was a perfect fit, just like Goldilocks.

She did things with her pussy no woman had ever done to me before.

Missy had me groaning and delaying coming was difficult but when I did, my eyes would roll back into my head and I'd spurt deep, thrusting over and over and over, Missy matching me with her own bumps and grinds, maximizing my pleasure.

I'd come and I stayed pretty hard but she'd lick and suck me right back to full strength.

Missy gave great head.

She savored the experience, working slowly and deliberately to maximize my pleasure.

I have no idea where she learned to give head like she did but I was glad to be the recipient of her education.

Plus Missy was a swallower, always a plus in my book.

She also craved a cock in her pussy and I did the deed, taking her many different positions. All over the suite.

I scratched her sexual itch and she made excellent use of my pleasure stick.

She came numerous times as did I.

Missy wasn't afraid of a cock up her ass either, and since I enjoy anal, well, let's just say she got reamed more than a few times while I had her cheeks spread so I could make a few deposits where the sun never shines.

As the movie

The Right Stuff

ends, there is a voiceover as Gordon Cooper lifts off into space, the last of the Mercury Seven saying "On that day, Gordo Cooper flew higher, faster and further than any man in space before him."

Well, that night with Missy in the Seattle hotel room I fucked her deeper, pounded her faster and gave her more orgasms than she'd ever experienced before.

I came in her three holes and on her; on her back, between her tits, in her hair and on her face.

Missy was a total slut for me and she loved being my slut.

But that was last night ...

Flying south above 40,000 feet, we had just passed Mount Hood off the left side of the aircraft.

Missy and I were in the passenger compartment of the plane.

There were two other females on board, in the cockpit, flying the jet.

Two attractive, former military pilots, both highly professional, who were making sure we flew to and landed safely at our destination.

They were discrete and understood confidentiality.

I was nude; and Missy had just finished blowing me.

She'd blown me the night before but this one, the one on the plane, on her knees between my thighs, was special.

****

Missy got up off her knees, smiling at me.

Then she bent down and took one last lick of my still hard cock.

Missy was still teasing me; maybe I'd spank her for it later.

I think she'd like that -- my hands slapping her great ass.

She sure did last night when I slapped her ass just once and she rolled over in total compliance on her belly with her thighs spread wide so I could easily mount her from behind.

And I did. She loved it, every thrust; every parry.

Every orgasm. And there were plenty of those on both sides.

It was a very nice memory of a night filled with nothing but pleasure.

Well, maybe some initial pain for Missy as I spread her cheeks and drove my baseball bat into her tight rosebud time after time, but even then she enjoyed it once she got into it.

****

Her assignment completed, the special lipstick blowjob finished, Missy headed to the restroom where she did her thing and then when she exited, I went in and did my business.

While I was busy behind closed doors, Missy slowly started getting undressed for round two.

Another nude wrestling match.

My intention was to let her come out on top in round two.

To let her win so we could schedule a tie breaker at some point.

I knew she'd like that.

I give Missy a lot of credit; we'd fucked all night long and here she was, getting ready to go again.

Her sex drought was over.

She took off her shoes, blouse, and skirt, putting them in the closet.

I walked out of the restroom in time to see her reaching behind to unsnap her black bra, freeing her large orbs from captivity.

She stood before me in only her panties. A very tiny pair.

Black. Silk.

Missy pulled on her nipples and rubbed her breasts to get the blood flowing.

How much of that was for her physical pleasure or for my viewing enjoyment I didn't know but I didn't care.

I liked her a lot but the fewer clothes she had on the more I liked her.

Smiling, Missy held her breasts out to me, in offering.

To suckle, to bite, to fondle.

To lick, to kiss, and yes, to clamp.

Her breasts were covered with my love bites from last night.

I looked at Missy and said to her "When those love bites start to itch, you let me know. I'll be happy to rub lotion all over them and make the itching go away."

She laughed and replied "I guess we'll be hanging around together then. I suspect they'll be itching tonight. To hell with the lotion I want your mouth and hands on them."

I was mesmerized by her nipples.

I held back my thoughts about pinching her erect nipples with metal clamps while she begged me to free them from the harsh punishment.

I knew that kind of pain would actually be quite pleasurable for Missy; her pussy would flow like the Columbia River.

I also would want her to wear some small weights on those eraser sized suckers because I wanted them stretched out just a bit.

I wanted to see if I could get them to be a half an inch longer.

She brought me back to reality with "Like what you see Jack?"

I took in the whole picture.

Studying her beauty. Her nudity.

I nodded, silently answering her.

I had a vision of Missy on our CYNSUITS website, in the smallest, most revealing suit we'd ever created, not showing her face, but certainly sharing that body with hundreds of thousands of hungry eyes, both male and female, making her (and me) a lot of money as those tiny pieces of clothing which we laughingly called a bathing suit flew out of the factory to customers paying a premium all over the world.

Her pink nipples now erect, she wet them with her fingers and pulled on them to get my complete attention; Missy knew my mind was wandering and she wanted my eyes and brain on her.

What a selfish girl.

I smiled as she teased those beautiful pink gifts.

Oh, she got my attention all right.

My eyes were glued to her almost naked body.

Her small black silk panties barely covered her soft trimmed red pubes.

Her torso was fine, tight; Missy has what is known as an "ab crack."

Staring at her I wondered how big she'll blow up when she got pregnant.

Notice I said when not if.

She was sure to get knocked up.

I didn't want to be the guy that did that deed.

After all, I'm a married man.

I'm only with Missy because my wife gave me a hall pass for two days.

I just want to practice making babies with Missy.

I want to practice a lot because we're very good at it.

Missy knew how to pleasure her man.

She loved me coming inside of her, and milking my cock dry, making sure every swimmer I deposited went deep into her female furnace.

One of the most special things you can do with someone when you are fucking is to come at the same time and Missy and I were already doing that. Not every time, but sometimes and man, when that happened it was magic.

So, I'm hoping that maybe Catherine, my wife of just a few short months, will extend the current hall pass or give me a new one.

I think Missy would like that.

Catherine, I'm not totally sure about.

Yet.

****

Even across the narrow cabin I can see Missy is excited.

Her nipples are aroused but that is not what I am looking at.

There is a small damp spot on the front of her tiny silk panties.

The excitement of her giving me the blow job got her hot and bothered.

I think undressing for me made her even more hot and bothered.

Playing with her breasts and teasing me made her even more aroused.

I can't smell her feminine fragrance just yet but I know soon will.

Even though we've only been together one night, I uncovered that Missy gets damp quickly, wet shortly thereafter and her pungent odor is right on top of that.

Lifting my eyes from her crotch to her eyes I ask "Was this your first blowjob on a plane?" and she laughs and says "No."

Her orbs move slightly; they're pretty firm but I enjoy the slight motion.

That I'm not the first blow job she'd given on a plane is interesting to me.

I'll follow that up sometime soon to learn more about her oral airborne adventure or adventures.

Smiling, I ask "Have you ever been nude on a plane?" and she laughed "No."

Missy continued with "But I'm looking forward to it" and she smiled at me.

She was enjoying this cat and mouse conversation.

She was running her fingers around the top of her panties in anticipation of removing them.

She's enjoying me watching her.

She likes teasing me.

I ask her to show her body to me and she twirls around.

I focus on the bare skin, of course, but also on that tiny thong.

I wonder if I can take that design and convert it into a bathing suit bottom.

That tiny string is tucked away nicely in her crack.

I'm going to pull it out soon.

With my teeth.

Her ass is great; I could bounce quarters off of it.

Laughing, flipping her shoulder length hair she twirls around for me twice, three times.

"Do you like what you see Jack?" she teased.

I respond with "You're beautiful."

It's true.

She is Flawless.

She is Perfection.

I wouldn't change a thing on her.

Well one thing, maybe.

I would shave her bush off but only because it would be fun to do.

But I can live with what she currently has covering her pussy: her thin wispy soft red pubic hair.

My mind drifts and I think about what a big red bush, wild and untamed, will look like on her.

I wonder if I will be able to get her to adult the pool in Vegas, nude on a late Sunday afternoon, showing off her full brushy red pubes to hundreds of men and women?

She'd get hotter than hell at that; our fucking after that would go to an entirely new level.

My mind started working hard on what that next level would feel like.

On my cock; after all, for me, it's all about my cock.

How long would it take for Missy to grow out her pussy hair?

My mind wanders about the possibilities and the timing.

I nod, thinking not only would I like Missy become a model, a nude model; she'd probably love to do it. For me.

I ask "Have you joined the Mile High Club?" and she responded by grinning and nodding her head.

I reply by saying "I'm planning on joining a little later with you."

Missy laughed and said "I can't wait. I love fucking you Jack. Fucking with you is fun."

I ask her "If there is one thing on your body that you could change what would it be?"

She smiles, tilts her head to the side, playfully thinking and then she holds up her orbs and says "I want bigger boobs!"

My mouth opens and my chin drops in surprise and she laughs.

She puts her hands up behind her head and shakes her tits.

For my benefit.

She says "I know you like them big Jack. Mine are more than a handful and you have big hands. You have a big cock too. A very big cock" and with that she physically shudders like she's having a small orgasm.

She's thinking about last night.

I'm thinking about the next hour or so with her.

My cock hardens. Thank God for Viagra. Not that I need it with Missy around, but what the hell, it is pretty cheap Erection Insurance.

I interrupt the short silence by saying "I have lotion that will make your breasts bigger. And firmer. Would you like to try some?"

She nods in agreement and then, taking a deep breath, she says, looking right at my rising erection, "Do you know what else I want Jack?"

I smile and ask "Tell me pretty lady."

There is a slight pause; then Missy says "I want a tighter pussy."

Her tongue licks her lips.

My cock stiffens.

Her left hand starts to slowly rub her left tit. Her nipples respond.

Her right hand heads south in the direction of her pussy.

Her fingers slip into the top of the black silk.

Oh My God she is going to start rubbing herself.

This is a dream come true.

For me.

I love it when women masturbate for me.

Missy continues "For you Jack. I want a tighter pussy for your big cock."

She's serious and I do not know how to reply so I remain silent.

I get harder.

She follows that with "I want you to struggle to get that one eyed trouser snake into me. I want every time we fuck to be like you're taking my cherry. I want a wet, hot, super tight pussy for you Jack. I want to be the best fuck you ever have. When you think about sex I want you to think about me."

I'm more than pretty fucking hard and I have the urgent need to start pulling on my dick.

After an awkward silence where her eyes never leave my now solid rocket booster, I shift in my seat, smile at her and she smiles back.

I reply "I think I would like that too."

She smiles, licks her lips again, her eyes fixated on my erection.

I repeat "What would you really change if you could?"

"If I can't have a tighter pussy then I wish God had given me longer legs to wrap around you when we fuck."

I assure her that she is fine just the way she is.

She laughs.

"One more thing Jack. From now on, my pussy is reserved for you. Only you. No other men."

I consider this: we now have an exclusive dating relationship.

According to Missy.

As Tom Leykis the radio DJ says "Dating means you're fucking."

But I notice Missy isn't excluding women.

Isn't that interesting?

This is one confident woman.

This is one competitive woman.

She's making an assumption that Catherine will allow me to keep fucking her.

I nod, hoping it might happen.

Missy is not being a bitch, far from it, but I could see why she got a divorce.

I don't think her ex could keep up with her sexual needs.

Lucky me, I was able to best her in the hot heat of the battle of the sexes last night.

I am not totally sure I won.

I do know I outlasted her, giving her orgasm after orgasm before I came for the first time and I guess that will do in terms of a so called victory.

Missy whispers, even though she doesn't have to "Last night was the best night of my life. How can I thank you?"

I smile in reply; my cock bobbing between my thighs, my sack is tight.

Missy walks down the aisle a few steps and puts down two seats on the plane, essentially making a bed for us.

She spreads a blanket for us to lie on.

My eyes are on her ass and those swinging tits as she does her housekeeping chores.

When she finished, Missy turns to see me staring at her and quietly asks "Will you please take off my panties Jack?"

I smile and say "I thought you would never ask" and she laughs.

Her nipples are erect ... really big.

She walks over to my seat.

I can smell her and I like what I smell.

A hot, wet pussy.

Reserved for me.

Exclusively.

She puts her hands on my shoulders to guide me and to steady herself.

I think she really just wants to be close to me.