Mile High Club?

Mark

Before I met Sam, I thought my cheating days were behind me. Although I still look back on my first affair with my coworker Monica as one of the most fun parts of my life, it was also stressful. The lying and sneaking around became harder and harder to keep up with until I couldn't. Inevitably, my wife Heather discovered our texts, including some racy pictures, which I'd forgotten to delete.

I wasn't sure we'd be able to get past it. In some ways, I guess I'm not sure we ever did. Heather was so hurt and pissed at me, with good reason. There are still unresolved issues below the surface of our relationship, not the least of which is the gap in our sexual desires.

Specifically, I want it all the time, and she doesn't. Which would be fine, except she's also not a fan of any ways I might try to take care of myself. I'm not just talking about looking for sex with other women. For a time, I dabbled in erotic chats online that never went past cyber sex, or occasionally phone sex.

When Heather inevitably discovered that, too, she was unhappy, and it reopened old wounds. I tried my best to explain to her calmly and rationally that I just need more. It has nothing to do with how much I love her, which I do. It's a physical need I have that's not being met.

But in the end, I decided I really didn't want to keep hurting her. To say she was accepting of me watching porn and jerking off would probably be an overstatement. But we'd sort of reached a don't-ask-don't-tell arrangement there. And so I'd settled into that reality for a while, accepting that things would not change at home, but that was the life I chose.

And then I ran into Sam. I literally ran into this girl in the middle of a crowded race through downtown Chicago. (Okay, she's not a girl, but at twenty-two, and ten years younger than me, a married father of two, most people would agree she's too young for me.) I wasn't looking for a hookup or another affair, but from the moment I saw her, I couldn't get her off my mind.

Just a couple of intense, sex-filled months later, I was packing for a business trip that I arranged as an excuse to whisk Sam away for a few days, so we could enjoy more than a stolen afternoon or evening together. Sometimes I wondered whether it should weigh more heavily on me, each time I chose to spend time with her instead of my family. But if I was honest with myself, there wasn't a lot of guilt. I just thought about being more careful so I won't get caught again.

And as I kissed Heather and the kids goodbye and headed out for my week with Sam, I'd be lying if I said I was feeling anything but excited.

***

I took an Uber to Sam's apartment to pick her up on the way to the airport. It was out of the way, but to me, it was worth it to spend as much time together as possible.

As I took my phone out of my pocket to text Sam and let her know I was on my way, I noticed an alert from the airline that our flight was delayed. So far, it was only pushed back by about twenty minutes.

Mark: On my way ;)

Mark: Looks like there's a delay

Sam: I saw that too

Sam: And I think I know how we can take advantage of that delay :P

Mark: Oh yeah?

Sam: Yep :)

Sam: I might be getting started already...

Mark: Mmm

Mark: Being a naughty slut while you wait for me?

Sam: I am

Sam: Touching myself inside the underwear you picked out for me :)

Mark: And what are you thinking about while you touch yourself? ;)

Sam: Just thinking about how I can't wait to feel you over and over all week

Sam: Everything we might do together, everywhere :P

Mark: Everywhere?

Sam: Yes :)

Sam: And wearing a skirt for the flight, just in case :P

Sam: Though it's hiked up right now

Mark: I'll change the Uber route to end at your place and come up when I get there

Mark: Keep touching, but don't cum yet

Sam: Okay :)

Mark: Be there in 5 minutes

Sam: Can't wait :D

When the car pulled up outside Sam's building, I grabbed my bags and headed up to her apartment. Even though we had a flight delay that might get extended, I knew we should make it quick, just in case.

So as soon as I made it to Sam's door, I dropped my bags and grabbed her right away, pinning her up against the nearest wall and kissing her lustfully, rubbing all over her.

I felt and heard her moaning into the kiss, running her hands up my chest, around the back of my neck. Then I caught a whiff of the intoxicating scent from her pussy and quickly grabbed hold of her right wrist before she could comb her fingers into my hair. I pulled back and held her hand right in front of my face, leaning in to sniff her fingertips.

As soon as she realized what I was doing, Sam blushed and bit her bottom lip, which was already looking swollen from our kiss.

"It's so hot that you were touching yourself as you waited for me to come over. You couldn't even wait for me to get here to make you cum, could you?"

She shook her head slowly. "I woke up so wet and excited to see you."

"Show me," I demanded with a smile.

Sam's smile grew, and she giggled, then reached down to hike her skirt back up around her waist. Then, she pulled up on the waistband of her light pink lace panties until it revealed the outline of her lips, and displayed a visible wet spot.

I reached down to rub over the fabric with two fingers, and Sam gasped.

Feeling her wetness spurred me on. I groaned and cupped the back of her head, pulling her back into another deep kiss.

Sam moaned into me, her hands running up and down my arms, fingernails scraping lightly over my skin and under my shirt sleeves. Then she slid her hands over my shoulders and down my chest until she was finally cupping and squeezing the hard bulge in the front of my shorts.

I pulled her shirt up, running my hands up to squeeze her heavy breasts through her bra.

Sam pulled her shirt up and off the rest of the way, smiling at me. Then she quickly returned to my bulge, opening my shorts as soon as she'd stripped.

"I need your cock once before we go," she asserted, sliding to her knees as she pulled it out of my shorts and underwear, stroking it in her face.

I didn't say or do anything to stop her, just watched as she leaned in and rubbed her tongue around my balls, then slid it up and down along my hard shaft.

"Fuck," I muttered, feeling and watching my cock twitch in her hand.

Sam moaned and wrapped her lips around my head, tongue rubbing underneath as she sucked me. She slid her lips down gradually further as her head bobbed on my cock, and her hand wrapped around the base, squeezing and stroking.

All I could do was moan and reach down to run my fingers through her hair, holding her head and guiding her as she sucked me. I watched her lustfully, my head occasionally rolling back in pleasure.

Then she reached into the back of my shorts with her free hand, squeezing my ass and tugging me closer as she took my cock deeper into her mouth, down her throat.

I groaned and pushed on her head, holding her in place. I felt and heard her gag, her throat constricting and squeezing around me.

When I finally released my grip, Sam pulled back and gasped in a breath. I noticed her skirt was inching up again as she spread her thighs, grinding her hips on the ground.

"Slide a hand back into your underwear. Touch yourself as you suck my cock," I ordered, gathering her long hair into a ponytail and wrapping it around my hand, getting a tighter grip.

Sam's face furrowed in pleasure and she whimpered softly. Her chest heaved more noticeably as she reached down to hike her skirt up to her waist, then slid her right hand into her panties.

As soon as she started rubbing, I gripped my cock and pushed it back between her lips. I used my grip in her hair to pull her head onto me, groaning and forcing myself deep down her throat in one thrust.

Sam gagged and moaned, rubbing her clit faster.

"Such a hot naughty slut," I moaned, getting more turned on as I watched her, fucking her mouth. I knew I was going to cum fast. "Getting turned on as you waited for me. Packing up to sneak away with a married guy. All the underwear I picked out for you to wear. Thinking about us staying in a hotel together for a whole week."

Sam moaned, the vibrations buzzing around my cock as she rubbed herself faster still.

I didn't let up, fucking her face faster, harder. "You love being my dirty college slut, don't you? I can't wait to fuck you over and over all week. In the bed. In the shower. Against the window. Having you waiting and ready for me as soon as I finish working for the day."

The way Sam was moaning and clenching, I could tell she was close, too. "Look at me, Sam. Cum while you're sucking me. I'm gonna fill your mouth."

The sight was almost too much: Sam, on her knees in front of me, her big eyes almost pained with pleasure as she looked right up at me. She had one hand inside her panties, rubbing fast. The other was on my hip so she could brace herself as I guided her on my cock, her hair wrapped around my fist. I felt the warm, tingling pressure building up in my balls, but I wanted her to cum first.

"Maybe I'll even send you on some side trips while I'm busy," I suggested with a smirk, hoping this would be enough of a tease to send her over the edge. Then I pushed harder on her head, forcing myself deeper down her throat for good measure.

That did the trick. Sam's lips loosened around my cock as she moaned and writhed on the ground, rubbing herself through her orgasm.

"Fuck. Good girl," I moaned.

I watched and waited until she'd finished cumming. Then I pumped into her mouth faster and harder until my cock pulsed, releasing spurt after spurt of cum into her mouth and down her throat.

As always, Sam swallowed every drop, moaning and sucking me clean before pulling back and licking her lips with a smile.

I smiled down at her, shaking my head in disbelief that this somehow kept getting better and better every time.

"Better check the flight again," Sam said with a smile as I helped her to her feet.

"Yep," I agreed, already reaching for my phone.

The departure time hadn't changed again, so I requested another Uber and we headed out a few minutes later when it arrived.

***

We got all checked in and through security at the airport with just a little time to spare before boarding. Sam wanted to browse in the bookshop while I got us some coffees.

Then, as we got to the gate just a few minutes before boarding, I remembered the surprise I'd packed.

"Oh yeah, I brought you something," I said, bending down to open the front zipper pocket of my suitcase.

"You did?" Sam smiled as I handed her a small gift box. "What is it?"

"Open it," I chuckled, as she finally took the box from me. "Carefully."

She gave me a wary but excited look as she opened the box.

"Maybe don't pull it out right here," I added.

Then I watched as she dug through the tissue paper inside, laughing and smiling when she saw what was there.

"I want you to wear it on the plane."

Sam bit her lip again, looking down at the pearlescent butt plug I'd picked out for her. It was metal, small but thick, with a shiny purple heart-shaped gemstone on top that would stick out while she wore it.

"Okay," she agreed easily, smiling.

"And Eggy, too," I added, referring to the remote-controlled vibrator I'd gifted her a few weeks earlier.

"I bet that'll make me feel really full," Sam said, barely restraining a big smile.

"And slutty," I added, feeling my cock stiffening in my shorts. "Better go put them in now before our group gets called."

"Okay, be right back," she agreed, easily.

"Good girl."

Then Sam grabbed her small shoulder bag and headed towards the bathrooms.

When she came back a few minutes later, a deeper shade of blush in her cheeks, the gate attendant was just calling our group number for boarding. I winked and gave her ass a discreet pat and squeeze as she went ahead of me in line, enjoying the view as we made our way to our seats.

Our row was towards the back of the plane. I'd already offered for Sam to have the window seat, but when we got to the row, she stepped aside to let me get in first. I wondered if it might have anything to do with the tall, handsome stranger who had the aisle seat in our row.

Once we settled in, I couldn't resist teasing.

"Wondering how big his cock is?" I asked, leaning in to whisper into her ear.

Sam just laughed and then bit her lip, not bothering to pretend she didn't know what I was on about. "Maybe."

"Naughty slut," I whispered back.

Then I took my phone out from my pocket and navigated to the app that controlled the vibrator in her pussy. I turned it on low to start, watching Sam closely for the subtle signs that she felt its gentle tease. A sudden intake of breath, and a slight clench.

"I want to make you cum right next to him," I said softly, into her ear again.

Sam didn't respond, but I noticed her chest heaving as she started breathing harder, her thighs squeezing together more.

"Wonder if he'll notice and get hard."

She couldn't resist another glance over at our neighbor's crotch as I mentioned it.

I continued to tease Sam with different vibrations as the last passengers boarded and the cabin crew ran through all of their pre-flight checks.

She reacted to every change I made, squeezing my thigh over the armrest between us.

"Building up?" I teased.

She nodded, biting her lip. "Maybe a little distracted with everything else going on, though."

I laughed. "Maybe."

But that didn't stop me from continuing to adjust the vibrations and intensity of the toy.

A little moan escaped Sam's lips just as the emergency drill messages started on the PA system.

I smirked, feeling my cock growing again. I knew I wouldn't be able to control Eggy remotely any longer now that devices had to be put into airplane mode. But I had a plan for that.

I left the toy on a medium intensity rolling vibe for take off. Then I put up the armrest between us and put my left hand on Sam's inner thigh, tugging her legs apart a little and rubbing between them. I kept glancing over to the guy on the other side of Sam, wondering if we were catching his attention yet.

He glanced down at her legs when I pulled them apart, but then he went back to watching a show on his tablet, maybe not wanting to get caught staring.

Then Sam smirked at me before reaching down to get something from her bag.

"I brought something for us, too," she said, taking out a small, rolled-up blanket.

As soon as she started spreading it over both of our laps, I knew what she had in mind.

"Naughty slut came prepared," I whispered.

"Yes," she agreed, smiling proudly. "Guess you're going to have to control Eggy manually now to make me cum."

Fuck. I'd had the same thought, but hearing Sam asking for me to make her cum right here on the plane caused my cock to throb, fully hard in my shorts and causing an obvious tent. Thank goodness for the blanket.

"Guess so," I agreed, shifting towards her in my seat.

Under the blanket, I slid my hand up between Sam's thighs again, looking around to make sure no one was watching as I pulled her right leg over my left one. Then I reached back between her legs and tugged her panties to the side, feeling for Eggy's tail. My fingers brushed over her smooth lips as I gripped the end of the toy and tugged until it slipped out of her, bringing a little gush of wetness with it.

"Mmm, so wet," I moaned, holding the main part of the toy, feeling it slip in my fingers, wet with Sam's juices.

She gasped a little as the toy slid out through her tight opening.

Then I held the egg part of the toy onto her, pressing in slightly and rubbing it up and down along her lips, then in circles around her clit.

"Oh, god," Sam moaned softly, her head turned towards me.

Our eyes met, and I smirked, using her facial expressions, sounds, and the pace of her breathing to guide me as I continued teasing her with the toy, working towards making her cum right there on the plane.

Occasionally, I'd glance up to take a quick look around, seeing if anyone had caught on. I thought Sam's left side neighbor must have picked up on something, but he still seemed pretty engrossed in his show. Kind of a shame. It would be hot to know he noticed and was getting turned on as I made Sam cum.

So maybe I didn't hold back as much as I should've for the sake of privacy as I pressed the toy onto Sam's clit, rubbing in harder, faster circles.

Her moan was loud enough to be heard above the droning sound of the plane engine, if anyone around us didn't have headphones in. Between that and the way she was squirming and arching more in her seat, I'd be surprised if her neighbor wasn't in on things at that point.

"Cum, Sam," I commanded, into her ear.

I pressed the button on Eggy's tail to turn up the vibrations and kept it pressed on her clit, rubbing fast circles, then up and down. Knowing how loud she normally got, and how much her body normally squirmed and writhed, I could tell she was struggling to contain her moans and movements.

A few more moments, a few more circles over her clit, and I felt Sam's nails dig into my leg harder, felt her whole body clenching up, stiff as a board. She bit her lip hard, eyebrows furrowed, then buried her face into my shoulder. Her mouth opened wide in a silent moan as she came, practically vibrating along with the toy in her seat.

"Good slut, cum hard for me," I muttered into her ear. "Squeeze around that plug in your ass."

Sam's face transformed into a huge smile as her body relaxed and she pressed my hand and the toy back from her now-sensitive clit.

"That felt so good," she whispered to me, her cheeks bright pink again.

"I'm so hard. That was so hot, watching you cum right here where anyone could notice."

"Yes, it was," she agreed.

I pressed the button to turn Eggy off for the time being.

Sam reached down to slip it into her bag. Then she got a mischievous glint in her eyes as she looked back at me.

"Your turn now," she said, mirroring my earlier actions and sliding her hand up the inside of my thighs, tugging my legs apart.

I chuckled, but didn't stop her as she reached for my bulge, wrapping her hand around my hard shaft through my shorts and rubbing. Then it was my turn to stifle a moan.

"I want to make you cum, too. Right into my hand, under this blanket," Sam whispered, her lips on my ear.

"Naughty slut," I teased, already thrusting up into her hand a little.

She made quick work of my belt and the button and zipper of my shorts, reached inside my underwear, and pulled my hard cock out underneath the blanket. Even though we were covered up, I knew the motion of her hand sliding up and down in my lap would be obvious if anyone looked over.

She seemed to like that thought, the biggest smile on her still-flushed face as she looked around and stroked me.

"That was my first time cumming on a plane. I hope that counts for the 'Mile High' club."

"We'll say it counts," I smirked, then stifled a groan as her hand continued working my shaft.

"I love being slutty with you. For you. Everything you tell me to do and do to me. It's always so fun and feels so good."

"Yes, it does," I muttered softly, already feeling a loss for words. "Your hand feels so good, too."

Sam kept whispering into my ear as she stroked me, varying the speed and grip. "I'm so tempted to just lean over and wrap my lips around you again. I love having your cock in my mouth so much. I want to taste more of your cum."

Even though I'd already cum in her mouth that morning, I felt it building fast, my balls tightening, hips thrusting into her hand, almost of their own volition. Hearing Sam's hot words and feeling her stroking me in such a daring public space had me close to cumming again, quickly.