The Island – Chapter 2

First time sex stories: The Island – Chapter 2

When I looked up at the face of the woman now sitting next to me in the window seat, at first my brain did not compute. I knew this woman, but I was having a hard time comprehending how she could be on this plane at this time. Any doubt that this really was Carol Bell was dispelled the minute she screamed “Davey! It’s you! I can’t believe it after all these years!”

She grabbed me in a big hug, nearly spilling my drink, and pressed those massive mammaries against my chest so hard I thought they would explode. She was obviously quite tipsy, and I chalked up the slightly inappropriate smack on the lips to her being drunk.

“I know you must think I’m still a lush like I used to be,” she said, “but I don’t do much drinking any more. Just a glass of wine with dinner sometimes. I just hate to fly so badly I needed a little help from the airport lounge to get myself on board without freaking out. I almost missed the flight!”

She was still a beautiful, if somewhat older, blonde with the same knockout body but now with added bonus tits! I did the math in my head and figured she would be about 48. I guess cleaning up her act saved her from looking run down at her age. We made small talk until dinner was served, and she pounded down another 2 drinks in the meantime. It seemed she had moved up the ladder in the supermarket industry, and was now a regional manager for the chain. She was being sent to South Africa in order to take part in a merger deal with a large international food distributor. She would be on the first leg of the flight, and get off tomorrow in Johannesburg.

She told me Gary was in the military, stationed in Germany, and was doing well. She spent a few minutes proudly describing his exploits. By this time, the trays had been collected and the flight attendants were shutting off the lights to encourage passengers to get some sleep. Carol slurred her speech as she thanked me for distracting her with talk while we had lifted off. She leaned in and put an arm around my shoulders.

“You’ve always been a great kid, “ she confided seriously. “I have to confess that I loved to watch you look at me when I was that insecure young single mom all those years ago. It made me feel better that at least someone thought I was something special.”

“I thought you were fantastic!” I said with a smile. “You used to drive me crazy with lust.”

“I know. I’m sorry. You were just a kid. But here you are all grown up.” She eyed me with a predatory expression. “I think you are pretty fantastic yourself these days.”

I chuckled and nodded at her chest. “You are definitely the same MILF you used to be, and you look like you’ve grown a little yourself.”

She grabbed her boobs and hoisted them in her hands. “Believe it or not, I got these as a Christmas bonus from work. My manager a few years ago was a dirty old man who offered to pay for them as a perk for my having reorganized our office. He figured afterward that they were his property, but I soon changed his thinking on that! Within a month I had gotten him fired and had his job. I am very selective on who I let touch these babies.” She let her lips brush my ear as she whispered “I think I might like you to touch them now.” She slipped her hand inside my shirt and began rubbing my nipple.

Having your high school crush come on to you in an airplane does wonders for your libido. I had a blue steel hard-on by now, and I quickly draped a blanket over us as I looked around. The plane was dark as people were turning in for the long overnight flight. Our nearest neighbors seemed to be fast asleep. I unbuttoned the top two buttons of her blouse as I slipped my tongue into her whiskey-soaked mouth. She gasped and gently bit my tongue as my hand hefted her right tit.

I lightly pinched the nipple and was rewarded with a moan of pleasure. She frantically reached for my fly and quickly had me unbuttoned and unzipped. I gave a little moan of my own as her cool hand encircled my rigid 9-inch erection and began stroking it. After a few minutes of hand-play, she leaned over and with a devilish look in her eye slurped by throbbing meat into her mouth. This lady was good. She cupped my balls with her right hand and slid her pursed lips up and down my shaft a few times before deep throating me briefly.

She then raked her nails across my nutsack, and gently ran her teeth up my rigid member until she reached the tip, giving a little nip to my foreskin that almost made me yelp. I then felt her tongue thrust its way into my pee hole, before swirling its way down my cockhead. She used her hand to pull my foreskin over the glans, and then slipped her tongue into the groove between the skin and the head, running it around the sensitive underside of the helmet, and drawing a hiss of pleasure from my lips. With her fist pumping up and down the shaft, and her tongue and lips working over the tip of my boner, I soon felt my balls tightening.

“I’m gonna come” I whispered hoarsely, figuring it was only common courtesy not to surprise her with a gusher of semen in her mouth.

She stopped her ministrations briefly in order to say “Go ahead, big boy! I’ve been waiting to taste your load for almost 20 years.”
That threw me over the edge, and I had to bite my lip in order not to wake up the whole plane with my moans as she sucked every steaming drop of cum out of my cock. After I had finished pumping my load into her waiting mouth she gave the tip a little lick and tucked it back in my shorts. She sat up and landed a boozy, lingering kiss, treating me to a taste of my own sperm, then collapsed back into her seat with a Mona Lisa smile on her face.

“God damn woman, but you know how to greet an old friend!” I gasped.

She laughed and said, “It was my pleasure. I just wished I’d gotten to your prick when you were still in high school.”

You gave me plenty to remember, I thought, you just don’t know it. Recalling my aborted attempt to reach nirvana on her bed those many years ago, I was determined to take advantage of the opportunity now. I didn’t think even in a darkened airliner I could get away with climbing on top of her and fucking her brains out, but I figured I could return the favor she had just given me.

“I’ll show you pleasure, baby!” I rasped as I slid to my knees between her and the seat in front of her. Her eyes widened in anticipation as I pulled the blanket over my head and her lap. With any luck, a passerby might think I was just out of my seat in the restroom and not realize what was going on under the blanket.

I reached under her pleated skirt and caressed her inner thighs. They opened to my touch and I grasped the waistband of her panties and slid them off. I was hit with a wave of Eau de Fuck Me from her aroused pussy, and inhaled deeply. The pungent scent was just as I remembered! I planted kisses up her thigh until my nose and lips were pressed up against her bush.

I was pleased that she hadn’t shaved it off like so many women these days. I slowly ran my tongue up her thick lips, now dripping with her dew, and slurped her clit gently into my mouth, sucking it like a miniature cock. I should have been worried her moans would bring the stewardess to check on her, but I was lost in the wonderful world of pussy.

I nibbled my way down her labia, pulling gently with my teeth on the sensitive petals, until I reached her gaping fuck hole. Plunging my tongue deep into her, I was rewarded with a flood of her juices, so much better from the source than from off of my finger. I licked her out as deeply and roughly as I could, and then replaced my questing tongue with first one, then two fingers.

Feeling for the sensitive area on the front wall of her quivering vagina, I began massaging her G-spot while tonguing her lips and clit. In short order I had her thighs clamping on my head as I brought her to shuddering orgasm. I licked her outer labia clean of her cream and emerged from my love tent to plop back in my seat. Apparently we had gotten away undetected, since there were no shocked spectators hovering around.

“That was awesome!” she breathed, her eyes closed and breathing deeply. She had a smile on her face as she drifted off into a drunken sleep. I grinned as I mentally crossed “Eating out best friend’s mom” off of my bucket list. Now I just had to clean off my soaking wet face and hand, and do something about my returning hard-on. I figured I’d hit the restroom back in the coach section, and at the same time check on my students, making sure they hadn’t destroyed the rear half of the plane yet. What a trip this is turning out to be I thought as I stood up and re-buttoned my pants. And it was just beginning!

I pulled open the curtain to the business class section and peered in. One businessman had earbuds in and was busy on his computer. Everyone else was asleep. No one seemed to have noticed the activities Carol and I had gotten up to in first class. Walking through the section, I peeked through the curtain into coach. I was pleased to see my students had settled in and all seemed to be asleep.

A few scattered travelers were either night owls or on different time zones, and were either on tablets or computers, tapping away obliviously. Several of the field hockey players were near the front, and had obviously been playing cards, as a few were scattered next to their sleeping forms. One of their chaperones was reading a book, and nodded at me as I passed, heading for the rear. Most of the back half of the coach section was dark, and everyone seemed to be asleep. I passed Janie and Jared, snoozing away.

Near the back of the plane, a single reading light was on, but its owner, a young woman, appeared to be out cold, curled up in her seat. The curtain to the rear galley was drawn, and muted sounds from behind it told me that the flight attendants were stowing equipment for the night. I reached the rear lavatory and was about to head in for a quick pull on my resurgent boner before washing up and turning in for the night. I glanced over at the sleeping young woman under the light and with a start realized it was the pretty cheerleader I had seen at the gate. God she was gorgeous!

Looking at her profile in the light as she lay curled up in her seat, a fuzzy white jacket draped over her shoulder, I was struck by how uncanny the resemblance was to the cheer captain of my high school. That girl had high-kicked and cartwheeled her way through my dreams and fantasies for 4 years. Melinda was her name, and even now I felt a twitch in my cock as I remembered how her big, bouncy breasts had moved under the sleeveless uniform top as she and her teammates did their routines.

I always sat in the front row, waiting for the glimpse of her Spankies that came with each kick. Then I would go home and jerk off, or if I had a girlfriend at the time, I would make out with her after the game, imagining it was Melinda’s crotch I was rubbing and Melinda’s had on my dick. I never did make any time with her, since she was joined at the hip to one of the football players–an overmuscled, underbrained but admittedly hunky jock named Dougie Carlton. How I hated him, knowing he was feeling up those magnificent mammaries in the back seat of his car after practice!

I shook myself out of my reverie and took a closer look at the girl on the plane. Now that I had taken the little trip down memory lane, I was even more aware of how much she resembled Melinda. For a minute I thought, I ran into one old friend on this plane, why not another? but quickly realized that was impossible. This girl was still a high school cheerleader.

Melinda would be grown up and had probably gotten fat and had 6 kids by now. Still, it was pretty surreal. I ran my eyes down her sleeping form and got another shocker: the way she was curled up sideways on the seat, with her jacket over her shoulder and her legs pulled up to her chest, I had a perfect view up her little skirt.

And wonder of wonders, she was going commando! My jaw dropped as I beheld her hairless cunt smiling at me in the spotlight of the reading lamp. Despite my recent world-class blowjob, I was hard as rock and ready for another cum. I took a moment to glance around and make sure no one else around me was awake. Slowly I dropped down to one knee, pretending to tie my shoe. This put her beautiful snatch at eye level. I drank in the lovely sight. She obviously tanned in the nude, since she was an even light brown over her smooth ass cheek.

The skin lightened as it passed the crease of her leg and onto her hairless outer lips. The velvety skin was smooth and flawless, stretching backward until it reached the puckered little pink ring of her asshole. Darker brown inner labia peeked out of her crack, enticing me closer. I wondered if she shaved this sublime cooze herself, of if she got it waxed at a spa. What an awesome job that would be: spreading hot wax on furry pussies all day! I got as close as I dared and inhaled deeply, savoring her aroma. It was tangier and less earthy than Carol’s, somehow fresher. I really needed to jerk off now, and reluctantly stood to head into the lav.

“Getting in some early sightseeing, huh?” an amused voice whispered in my ear. I almost jumped out of my skin.

“Jesus Christ!” I hissed, spinning around. There stood my redheaded stewardess, hands on hips and a stern expression on her full lips. She had flaming red hair that was a mass of tight curls, piled high on her head. Her eyes were a deep sea-green that I could have drowned in. Her creamy white skin was dusted with a spray of freckles across her pert, turned-up nose. Her tailored uniform hugged her full hips and curvaceous figure. She was beautiful, and right now, utterly terrifying.

“I…uh..I…was…” I stuttered, intending to trot out my shoe-tying excuse, but one look at her face and I knew I had been busted. I shrugged and gave her a grin. “If it’s on display I’ll take a look.”

She glanced at my little honey’s bare twat, then leaned past me to flick off the reading light. Her soft breasts brushed my chest as she did so, reenergizing my terror-stricken boner.

“No sense in letting everyone get a free show. You should be ashamed of yourself! She could be your daughter.”

God help me if I had a daughter who looked like that, I thought. “ I wasn’t hurting anyone,” I said a little desperately, not wanting her to think too badly of me.

“Come back here, buddy,” she said, motioning toward the galley. “We need to have a little talk.”

Oh shit! I breathed, fearing I was in the crapper now. I stepped into the alcove and she drew the curtain.

“What were you thinking, looking at that poor girl’s pussy like that?” I was silent as I struggled to find some way not to look like a pervert. Her next words surprised me. “Did you get a nice, thick hard-on watching that little cunt?”

“Um, maybe…” I mumbled, taken aback.

“Did you want to touch her? Maybe stick your tongue up that crack and taste her?”

My eyes must have been as big as saucers. I had no idea what to say.

“You are such a bad, bad boy. Don’t you feel ashamed?”

“A little,” I admitted.

“If you tell the truth, and take your punishment like a man, you’ll feel better, and maybe I’ll reward your honesty,” she said severely.

“Yes. Yes, I wanted her badly.”

“Are you ready to accept the consequences of your actions?” she asked, her eyebrow arched.

“Yes, “ I said humbly, wondering where this was going.

She sat on her little jumpseat against the wall. “Drop your pants!” she commanded.

“What?!”

“You need to do your penance if you want to escape a more severe penalty. Now drop your pants or I wake up the air marshal.”

“OK, “ I said, pulling down my Dockers. Despite my terror, I was still aroused, and my shorts were tented out to an impressive degree.

“Tighty-whities, too, Mr. Voyeur.”

I slid my jockies off, letting my boner spring out of confinement. I stood in front of her, a curious mixture of humiliation, dread, and arousal making my heart race.

“That prick doesn’t look very remorseful. In fact, it looks pretty cocky, if I may say so. I think it needs to be disciplined. Maybe choked, or spanked,” she said with an evil grin. Does she mean what I think? I wondered.
“Go ahead and spank it.” She does!

I slowly reached up and grasped by throbbing shaft. I stroked it gently back and forth, looking her in the eye. She crossed her legs, giving me a brief flash of panty and creamy white thigh. “Harder!” she insisted.

I began jerking off in earnest. I had never done this with an audience before, and it was a heady experience. My knees were trembling as my fist pumped up and down my rigid member. Her eyes were glued to my dick as the purple head popped in and out of my flying fingers. Despite just blowing a load a few minutes ago, I felt another cum explosion building.

As if reading my mind, she said, “After your little workout in first class, I’m surprised you have enough jam to go again.”

My jaw dropped and my pumping slowed. “You know about that?”

“Don’t stop now! That sweet meat of yours is starting to drip. Finish yourself off, naughty boy!” she ordered. “I watched the whole thing through the curtains up front. Did you like her warm lips on your cock? Did you like the taste of her pussy?”

“Yes!” I hissed, getting into the spirit of things. “I stuck my tongue all the way up her cooze. I had her honey dripping all over my face!” My nuts were tightening again.

She was breathing heavily, and squirming in her seat as she watched my orgasm build. “Did you think of me while you finger-fucked her? Or while you were sniffing around that cheerleader’s cunt?”

“Oh, yes,” I said fervently. “ I want to rip your clothes off and get balls deep in your twat! I want to taste your dripping pussy. I want to bite your nipples and make you scream. I want to pump my jizz deep into you, you nasty bitch!”

With that I erupted, spewing yet another epic load from my spasming member. Fountains of white semen flew out, spattering the floor, the wall, and her shoes. I finished pumping my dick until it was empty and I was exhausted. I slumped against the wall, my spent peter dripping against my thigh. I wasn’t sure but it looked like she had had her own orgasm just watching me. She sat there, breathing heavily, staring at my softening prick, then seemed to collect herself.

She straightened her shoulders, licked her lips, and stared me down. “Very good! You have almost completed your punishment. Now lick my shoes clean!” She lifted her right leg to my hand and I cupped the heel, holding it high. I had a nice view of her damp panties as I slowly tongued the cum off first the right shoe, and then, switching her legs, the left. I dropped her leg and asked, “Now what?”

“Clean your mess off the floor and the wall.”

I grabbed a towel from the galley and did so, my naked wedding tackle waving in the breeze.

“You have done very well. I will have to think up a suitable reward for your honesty and obedience. Now get yourself cleaned up and dressed before one of the other flight attendants comes back here.”

I slipped into the bathroom and washed up, my mind reeling. By the time I stepped out, my abused cock tucked away again, she was gone. I made my way back to my seat in a daze, and quickly drifted off to sleep.
This is the most bizarre trip I have ever been on, I thought as I slipped into unconsciousness. And something tells me it is only going to get stranger.

——————

Parent Post: The Island

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