The Island

First time sex stories: The Island. Author: Paperbackwriter. The story is including: Fiction, First Time, Male / Older Female, Masturbation, Voyeurism. This is a serial novel. It mixes actual experiences, fantasies, and outright lunacy. It is not a quick lurk-and-jerk. I believe in a slow build, in order to have a better payoff at the end. (Like Sting, I’m Tantric…). I plan to release a new chapter every week. Hopefully the response will be good! Enjoy.

First time sex stories: The Island – Chapter 1

Author: Paperbackwriter

It was my lucky day. I was 32, single, and flying to Korea on someone else’s dime. As I settled into the first class seat and had my drink topped off by the hot redheaded flight attendant, I had to take a moment to appreciate just how this had all happened.

Originally, I had thought that this year was turning into one big suckfest. My long-term girlfriend and I had broken up 3 months ago after a screaming fight. She had felt the ol’ biologic clock ticking and started pressuring me for a kid. I told her I wasn’t ready and things degenerated from there. I had been a little down since then, not necessarily because I missed her, but because I missed the regular sex. I hadn’t gotten laid in 3 months and it was killing me!

This was on top of losing my job the previous month. For over a year I had been working as a temporary replacement surgeon in a small Maryland town, filling in for an older doc who had been out on medical leave after a nasty car accident. Just when it looked like this might turn into a more permanent gig, he had the nerve to get better and return to his practice! Now I was out of a job and had to start looking for a new position.

This may have been why I had been spending so much time at the local Tae Kwon Do school. Aside from the satisfaction of venting my frustration by (mildly) beating the crap out of people during sparring practice, I had been trying to get physical in a different way with one particular student.

Janie was a petite brunette, a few years younger than me. A recent divorcee, she didn’t have the fantastic tits my ex sported, but she more than made up for it with her rock-hard body, including an ass that was so tight she could crack walnuts by flexing her glutes. The last month or so, I seemed to have finally broken through her own break-up funk and gotten her interested in seeing me outside of class. In fact, she was the reason I was on this plane.

Our school was sponsoring a big cultural exchange with the Korean tourist ministry. 20 of our students would spend an all-expense paid week in Korea with martial arts classes and sight seeing tours, and the following month 20 Korean students would come to the US for the same treatment. The students ranged in age from 6 to 16 and needed chaperones. Jamie had agreed since her son was one of the students, and she asked me if I would be the male chaperone. Having no ties to keep me in town any more, and hoping to score some excellent vacation sex, I agreed.

It was quite the banner day for our small town, as not only were they sending us cultural ambassadors of the martial arts, the regional high school had scored slots in the women’s world field hockey finals, also being held in Seoul, and the varsity football cheerleaders were tagging along for an exhibition at the games. I was a little annoyed that they hadn’t sprung for their own bus to the airport since the two hour ride was pure chaos, but I shrugged it off, feeling like I was still getting a great deal.

So an hour ago I found myself sitting at the gate in Dulles, after a couple hour bus ride to the airport with a rambunctious bunch of Tae Kwon Do students, field hockey players, cheerleaders, and associated chaperones, checking out my traveling companions. Janie was sitting next to me, her long brown hair done up in a pony tail, which always made her look particularly hot and younger than her age.

She was rocking a tight pair of jeans that showcased her amazing ass, and a plain white T-shirt, made less plain by her perky little tits, which were braless as usual. Her 8-year old son Jared was at the other end of the departure lounge, playing video games with his friends. 12 of the 20 students were boys, and they tended to hang together.

They were prone to roughhousing and yelling insults at each other, which I was supposed to control, being the male chaperone. The other 8 were girls, including a few hot lovelies who always got me a little randy during class watching their polka-dot-panty-clad asses churning under their white uniforms. Look but don’t touch! I had to remind myself constantly. It would not do for the local doctor to get caught playing grab-ass with innocent suburban girls. Boy, did I like to look, though!

The field hockey team seemed like the typical stereotype. Toned and athletic, and some quite attractive, but seemingly interested more in each other than the teen boys from our school, if you catch my drift. They were accompanied by two fierce looking women who seemed up to the task of keeping unwanted male attention from their precious charges, but in my opinion posed more of a threat to the girls’ virtue than any man. I wasn’t sure if they were a couple, but they seemed awfully close for friends.

The cheerleaders were more my type. Young, hot, and flirty. They were all giddy, talking a mile a minute, excited to be leaving the US on an adventure. There were 10 of them, including one guy who was definitely not going to be bothering the field hockey players, and one stunning girl who was the spitting image of my first crush, the cheer captain of my own high school. She was 5’4” and busty, with light brown hair, a gorgeous smile, and the word “PINK” plastered across the ass of her sweatpants.

I could only imagine how pink she was under there! Just watching her had gotten me horny, and I wondered if I could convince Jamie to join the Mile High Club during the flight. Either that or I was going to have to jerk off in the lav to get to sleep during the overnight flight. They had their own chaperone (Good luck to her! I thought to myself), a surprisingly pregnant woman, about 24, who I believe was their coach and also one of the French teachers at the school. She seemed to be about 7 months pregnant and I was amazed she was allowed to travel in that condition. I guess they needed their coach and she must have gotten approval from her OB/GYN.

In addition, there had been the usual mix of international travelers. There were a few families, several Koreans returning home from visiting the US, some obvious professionals travelling for work, and a collection of neo-hippy backpacker types, presumably planning on traipsing across the country, scoring weed and having lots of outdoor sex. There was also a tense group of Middle Easterners, including a couple of chicks in burkas. At the time, I had been a little suspicious of them, but chided myself for racial profiling. Plus, terrorists didn’t usually bring their women with them.

We eventually boarded, and we filed into our seats. The flight was surprisingly not very full. I was supposed to sit with the boys from our dojang, but I had played the MD card when booking my ticket, and had lucked out with a free upgrade to first class. I figured there was only so much trouble the boys could get into on a sealed airplane.

I should probably have tried to sit with Jamie, but in typical airline fashion, our group’s seats were scattered all over the aircraft instead of in one section. She was sitting with her son, anyway, so I suspected I would not be able to convince her to have our first fuck in an airplane bathroom with him 6 feet away. The first leg of the flight was an overnight run, and I rationalized we would all be sleeping through it anyway. I gave Janie a shrug as she walked by to the coach section, and she returned a sexy little pout, letting me know she wasn’t mad.

So here I was, in the aisle seat, scotch in hand, eyeing the smoking hot stewardess who had poured it, thinking that sometimes life really was great. The window seat was still empty, and as they were just about to close the door, I figured I had the whole row to myself. Suddenly, a woman came barreling through the jetway onto the plane.

She seemed a little flustered and unsteady, and I couldn’t help thinking she looked familiar to me. After checking her ticket she staggered up to my row, and hoisted her bag up to the overhead compartment. This gave me a fine view of her magnificent rack, which jiggled enticingly as she crammed the carry-on into the bin. When she bent down to slide past me into the window seat, I got an even better view right down the front of her low-cut blouse.

She had a sweet pair of obviously fake boobs, which jutted out from her chest like grapefruits. Erect tan nipples topped off this display, and I was mesmerized as they swung their way past me. I could feel my prick twitching and hardening with interest. She plopped down next to me and I forced my eyes off her chest and up to her face. At this point I got the first shock of what was to be a truly memorable trip.

When I was growing up, my best friend was a guy named Gary. We were inseparable, and every weekend we would sleep over at each other’s house. I preferred his house, not because I didn’t like my family, but because of his mom. She was a young, single mother, having had Gary when she was 16. I guess she was a bit of a party girl, and I don’t think she even knew who the father was. She was a good enough mom to him, working hard at a supermarket to pay the bills, but never quit her wild ways.

She would often come home fairly late Saturday night, totally hammered, and pass out while still in her clothes. I guess it was her release after a week of being the responsible parent at such a young age. I never told my folks about this, since I was sure they would stop me from spending the night where the only adult in the house was shitfaced.

As I entered middle school, I became increasingly aware of how attractive she was. She was a natural blond, tall and willowy, and I now realize she must have gotten off a little by teasing me. Not having a regular man in her life, she probably enjoyed exerting her charms on a helpless, horny teen boy. She would frequently walk past Gary and me while we watched TV, dressed only in a towel, ostensibly taking her clothes into the laundry room before showering. On one memorable occasion when I was 13, she “accidentally” let the towel slip right in front of me while Gary was in the bathroom.

That’s how I know she was a natural blonde. That fluffy honey-colored bush was the first female pubic hair I ever saw. I nearly always had a constant boner when she was around, but this time I nearly shot a load into my pants. Seeing her naked body was the high point of my young life. She squealed and grabbed the towel, quickly covering herself up, but didn’t seem too upset by the whole incident. I, on the other hand, had to rush to the bathroom myself and furiously jerk off as soon as Gary got out. I probably pulled my pud 4 times that night thinking of her pubes and wondering what they were hiding.

For two years that sight was burned into my brain, and she continued to tease me with occasional glimpses of her body. Then, when I was 15, something happened that probably explains why I am such a horny pervert as a grown man. That Saturday night I was again over at Gary’s. We had just watched some sleazy teenage sex comedy on HBO (another reason I liked staying at Gary’s–I could watch R-rated movies) and had finally turned in for the night. Gary was snoring away, keeping me awake as much as my hard-on was, when his mom came in from her latest bar crawl.

She was completely plastered, and was singing to herself as she staggered up to her room. As per usual, she collapsed on her bed and was soon snoring even louder than Gary. I don’t know what came over me; it must have been my adolescent hormones, already in a frenzy from the movie. I started thinking about her body, and how beautiful it seemed during all those peeks I had been given over the years. And now she was just down the hall. Asleep. Passed out cold.

Trembling, I got out of bed, careful not to wake Gary. I crept down the hall and looked into her room. She was lying on her back, with the light still on. One arm was thrown over her head, pulling her silk blouse tight over one braless breast. Her skirt, fairly short to begin with, was hiked up to her crotch, and I gulped as I saw a tiny piece of black lace vainly trying to cover up that sweet blonde twat.

My heart was pounding and I was feeling dizzy as I built up my nerve. I started slow and trailed my fingers across her arm, thinking that if she woke up, I would say I had a headache and needed some aspirin. When she didn’t stir, I got bolder and ran my fingers over her breast. The nipple hardened under my touch, and I began to breathe heavily.

I slowly unbuttoned her top, until her naked B-cup tits were fully exposed. Her breasts were small and high, with large, tan nipples jutting out of big silver-dollar areolas. This was the first time I had ever gotten a good look at a pair of boobs, and I was mesmerized. I sat down on the bed and began stroking her tits, at first softly, then increasingly aggressively.

She was totally out and didn’t stir at all. Having one particular sex scene from the movie firmly in my head, I bent down and licked her left nipple. It was warm and a little salty with sweat. I had no experience with girls at this point, but instinct took over, and I was soon sucking away at her teat like a champion.

It had my boner raging, but seemed to calm my breathing down, at least. After a while I switched to the right side and gave it a workout as well. My shorts were now wet with the precum leaking out of my rigid cock, and after I had satisfied my lust for her tits I stood up and yanked them off, freeing the most painful hard-on of my young life. I stood there stroking my dick, appreciating her now glistening, puckered mounds, before my gaze wandered down to that hypnotic display of panty crotch.

I could probably have set off a bomb and not woken her, but I kept glancing at her face, convinced she was about to wake up and denounce me as a perverted little bastard. She just snored on, however, and I got a little bolder. I felt an unstoppable compulsion, and like Moses and the Red Sea, I parted her thighs and headed for the promised land.

I crawled up onto the bed between her legs, my sensitive dick head painfully dragging across the bedspread, and gently pressed my face against the gusset of her panties. I could feel the springy hairs under the thin fabric, and I inhaled deeply. Her fragrance was strong, a heady mix of female sweat, pheromones, and a salty, tangy odor that I had never experienced before. I was intoxicated. Running my lips over her fabric-covered mound, I felt her warm flesh just millimeters away from me, heat radiating off her like an oven.

Her scent was making my brain buzz and my heart pound. I needed more! With one hand on my cock, I brought the other up and, with trembling fingers, carefully pulled the lacy fabric to the side and revealed her cunt. A dense, untrimmed thicket of golden curls framed a pair of pouting, pink lips. They gaped slightly, and I saw a ridged pink tunnel, glistening with her juices, tucked up inside.

I wanted to plunge my cock in her to the hilt, but I was convinced that would certainly wake her up, so I had to satisfy myself with gently sliding in a finger. She was warm and wet and soft, and right then and there I decided that pussy was the greatest thing on earth. I have spent the last 17 years trying to recapture the intensity of that moment with plenty of other girls and women, but never have I equaled the strength of those feelings that Saturday night.

There I was with my finger buried in the sopping wet pussy of my best friend’s mom, someone whom I had been obsessed with for years! I was jerking my cock so hard the whole bed was shaking (which probably should have clued me in I could have gotten away with a lot more), and I watched those meaty lips gape as I pulled my finger out of her.

My finger was coated with a thick layer of female juice, and I brought up to my nose. It smelled like heaven, and I knew I had to taste her. I slipped the finger into my mouth, and the tangy, womanly flavor of her was finally more than my overtaxed libido could handle. I shot my load all over her bedspread, bucking like I was having a seizure.

After I finished gasping and spurting, I panicked, realizing what a mess I had made on her bed. Reluctantly I covered that beautiful pussy back up and did my best to re-button her blouse. I am not sure I even got the buttons to match up I was so shell-shocked. I grabbed some toilet paper and tried to mop up the ropes of white jizz I had sprayed everywhere. Some was even on her calf, and I carefully wiped it off while watching her face. She had stopped snoring, and I could almost convince myself she had a smile on her face, but that was probably my imagination. I staggered back to Gary’s room and collapsed into bed. I figured I would be up all night replaying that amazing scene in my head, but I was so exhausted I fell asleep almost immediately.

The next day I was in a daze, not sure if it really happened, but when I lifted my index finger to my nose, I could smell the telltale scent that let me know I had not been dreaming. Gary and his mom behaved completely normally, and seemed to be a bit confused at how clumsy and distracted I was, and how completely unable I was to look at Mrs. Bell for the remainder of the day.

I thought I might get a chance to repeat the performance next month, but it was just the next week Gary told me that he and his mom were moving to the next county, as she had gotten a promotion and would be managing a supermarket two towns over. I kept in touch with Gary for a little while, but high-schoolers aren’t known for responsibility, and I soon made new friends. I never saw Carol Bell again.

Until now.

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