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.