Let me tell you about Samantha

Disclaimer:

This is a work of fiction. Any resemblance to real events or people is purely coincidental and not intentional. This story obviously contains adult content. If a tag was included, it was included for a reason. Please keep that in mind before you read this story.

I am not interested in negative comments. I believe that the more realistic a story, the easier it is to suspend our disbelief, and therefore the easier it is for us to become involved in the story. No one is forcing you to read what is written here. That being said, comments are welcome, and I hope you enjoy.
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Let me tell you about Samantha. I first met her when she was seventeen. We were working at an outdoor pool in Michigan. She was a lifeguard and a swim teacher, and I, being a few years older, had some time ago been promoted to supervisor. It was my job to hire staff for the summer, train them, and make sure they kept our guests safe while on duty.

There were strict guidelines that the lifeguards had to follow. Gone were the days of lounging in the sun, drink in hand, whistle twirling while snoozing in the sun on the guard stand. With increases in drowning incidents in the past years, and subsequent insurance hikes, our facility could not afford to compromise on safety.

The training program was vigorous, and not everyone passed. I had ten kids that year that wanted to work for me for the summer, and only seven of them ended up passing the course. I remember the first day, an older kid named Jared tried to fulfill the swimming requirement, and barely made it halfway across the pool. He was well built too, and in good shape, he just had no technique.

Sam was a different story. She was on the swim team in high school, and was more at home in the water than on dry land. She had an incredible body too. She was about 5’2”, under 100 lbs, blonde with bright, penetrating, blue eyes. She had a nice chest too, although her one piece swim suit did little to show it off.

She passed the swimming requirements without a problem but struggled a little when it came to learning CPR and some of the rescue skills. For obvious reasons, I wanted to keep her around, so I was more than happy to volunteer to spend some extra time tutoring her after the rest of the staff had left.

This continued for the duration of the week-long course, and by the end of it, we had established a decent rapport. There was still a distance between us, since I was not only a little older, and had outgrown her high school drama, but also because I was her boss. Nevertheless we got along fine, and I slowly learned more and more about her. She would come into my office every once in a while on her breaks and we would chat. She even brought snacks occasionally. I could tell she had a little bit of a crush on me, and let me tell you, I was happy to see her every time.

Sam was very proper and very innocent. She came from a religious background, and was planning on saving herself for marriage. She was a little naive, without a doubt a unwise as to the ways of the world, as everyone in her life was artificially nice to her, probably because of her looks. To put it another way, she was incredibly hot, but not always all that bright. Part of it was her age, and part of it was her… innocence when it came to all things romantic and intimate.

One day, near the end of summer, she came into my office near closing time in tears. It was the first time she had come to see me all day, which was odd, and I could tell something had been bothering her for a while. I, ever the good boss and friend, offered her some water and slowly coaxed the story out of her.

It turns out that Dylan, a boy from her high school whom she had been dating for a while, was finally tired of waiting for her to put out, and had taken advantage of her. Over the course of the evening, and long into the night, she sat with me and told me the story:

Sam and Dylan had been dating since sophomore year, and like typical relationships, it started slowly and awkwardly.