Let me tell you about Samantha by DarkAggro

A literotic sexstories: Let me tell you about Samantha by DarkAggro
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. There was hand-holding and hugs, and all of the usual bullshit that goes with adolescent romances. Sometime around junior year, Dylan, a football player, wanted more. He told Sam that unless she started to put out a little more, he would break up with her and date a cheerleader.

She refused for a while, she said, until last week when things finally came to a head.

Dylan took Sam on a romantic drive into the countryside one night, with the premise that they were going to look at the stars. Michigan has some beautiful forests and a lot of secluded places to park a truck where no one can find you. They drove up a long dirt road, late at night, and Dylan laid out blankets in the back of the truck.

He had gotten his hands on some tequila, and the two of them were taking turns drinking out of the bottle. Sam had never had anything to drink before, and the effects of the alcohol were hitting her pretty fast. Dylan drank more than he probably should have, and was soon feeling frisky.

“Come here, babe” he said to her, slightly slurring his words as he held open his arms.

He was laying on his back in the middle of the truck bed, pillow under his head, bottle in his hand. Sam lay down beside him, placed her head on his chest, just below his shoulder, and curled up against him, placing her knee gently on top of his crotch.

“Ooh yeah babe… that’s what I need.” Dylan grabbed her knee and forcibly pushed it down into himself. Sam felt his cock through his jeans, and knew that he was already rock solid.

“Babe, you know I’m not ready” she said to him, eyes wide and bright in the moonlight. Her skin tight white cotton shorts hugged every curve perfectly, and her light blue tube top slid up just a little bit, revealing her tight, toned, and tanned stomach.

Dylan didn’t say a word, and just reached his hand down the back of her shorts. He felt, rather than saw, her lacy pink thong, clinging to her perfect ass. Feeling the top of that fabric wrapped around her drove him a little crazy.

“Tonight is the night babe. I’ve waited long enough. If you love me, you’ll do this.” Dylan was doing his best to lay on the charm, but the tequila was making him sound sleazy and manipulating.

“If you love me, you won’t ask me to.” said Sam, wriggling out of his grasp and forcibly removing his hand from the back of her shorts.

“I said no, and I meant it, Dylan.”

Dylan rolled his eyes and took another swig from the bottle. He took a long hard look at Sam, standing up in his truck bed. The moonlight shining on her face made her look more fragile and delicate than ever. The slight breeze was making her light cotton top ride up just a little, and he got a few more glimpses of her perfect midriff. He got an unobstructed view of her in profile, outlined against the star-studded background. Perfect, full little tits, and an amazingly tight, firm little ass, wrapped up in shorts that showed off her tan.

Something must have come over him, because suddenly, and without warning, he reached up and grabbed her by the waistband of her shorts. She wasn’t sure if it was the liquor or the two years of aching blue balls that did it. Likely it was a combination of the two, but Dylan was not waiting any longer. He pulled down hard on her shorts, and she instantly fell to her knees in the truck bed.

“Hey! Stop it!” she yelled, trying to free his vice-like grip on her pants. It was a useless endeavor. He was easily double her size and he had already made up his mind about what was happening tonight.

“Turn around” He said to her, with a look in his eye she had never seen before.

He climbed around behind her and pinned one hand behind her back. She was still on her knees in the truck bed, facing the cab, when he forced her face into the blankets. She screamed in pain as he twisted her shoulder even harder, tears welling up in her eyes.

With his free hand, Dylan reached around the front of her shorts and undid the button and zipper. Sam started to panic and tried to fight him off with her other hand, but he tightened his grip and forced her face still lower until she stopped struggling.

“Help me!” she screamed out into the dark woods. “No, stop! YOU’RE HURTING ME!!”

Dylan wasn’t listening anymore. He had pulled down her shorts, revealing the nicest ass in all of Oakland County (at least). Tight, firm, and toned, with a great tan and tan lines from working outside. Swimming made her lithe and muscular, but not butch or scary. She was in great shape, and her hard little body was his for the taking.

His cock was aching to get out of his pants, especially at the sight of that ass, bent over in front of him in that lacy pink thong. Sam was still struggling and calling for help as Dylan fumbled awkwardly with his own zipper, not daring to let go of her arm lest she try and run away.

He finally managed to pull his cock out, and laid seven inches of throbbing meat right between her ass cheeks. For the first time that night, Sam was still, and stopped struggling.

“Please, no. Dylan…”

He pulled her thong to the side and positioned himself outside her tight little virgin pussy. He spit on his dick twice (he’d seen it in a porn flick) and rubbed the head of his dick up and down her tiny slit. She was completely clean shaven, something that carried over from swim practice.

“No, no, no, no, no, AAAAHHH!!” She was shaking her head the whole time he was rubbing her, and when he finally thrust forward, into her, the shock was incredible. His cock wasn’t enormous, but she was tiny, a virgin, and not ready for it. He was brutal and totally unflinching as he grabbed the crease of her hips with his free hand, and used his 210 lbs of football muscle to drive himself into her.

She was as tight as a drum, and was squeezing him harder than anything ever had. As he split her open and felt the warmth of her insides, he threw his head back and let out a moan, or a groan, that was kind of a sigh at the same time. Two years of waiting and it was everything he ever wanted it to be.

He felt her go limp underneath her as the will to struggle went out of her. He let go of her arm and used both hands to grab on to her hips. He started pumping in and out of her, in long, deep thrusts, pushing ever deeper, and stretching her ever wider with each movement. Every time he reached the bottom of his stroke, she would let out an involuntary moan. Actually, it was more like a sob, but at this point, Dylan didn’t care at all. All he cared about was this pussy and how it was squeezing him.

“Oh my God, babe. Oh. My. God.” He said to her, as if she was doing him some sort of favor. Her lips were moving, but no words were coming out. Her beautiful, tanned, teen face was streaked with smeared mascara, and her bright blue eyes were glistening with tears. She just wanted it to be over, but to her horror, Dylan seemed to be picking up speed.

He thrust ever deeper, ever harder, until he finally buried the full length of his shaft inside her. He held it there for what felt like forever to Sam, pulling her hips into him. Her mouth was open the entire time, but there were no screams left inside her. Finally, he pulled out slowly, letting her squeeze his shaft all the way out.

He pulled her little thong the rest of the way off of her ankles, then gave her a brutal smack on the ass to get her attention.

“Turn around” he said to her, for the second time that night.

She slowly did as she was told, and once she was on her back, he ripped her tube top off, revealing her perfect teen breasts. She was covering her nipples with one arm, and her other hand was down between her legs, trying to soothe her aching, bruised little pussy. Dylan removed her hand from her opening and spread her legs before climbing on top of her and entering her again.

Her face, at first, looked scared. After the first five deep thrusts in this new position, fear was replaced by a look of agony. Her eyes were wide again, still glistening, and her mouth was open in a silent grimace. Her whole body felt the violation of what was happening, and it was all reflected in her beautiful face. Ten more thrusts and her expression changed again. The pain subsided, and was replaced by an almost passive apathy. Her whole body still shook with each forceful thrust, but he had finally split her open enough that she didn’t have to scream anymore.

“You little slut, you love this, don’t you?” Dylan grunted at her, all the while pounding into her.

When she didn’t reply, he grabbed a fistful of her hair and yanked on it, forcing her to look in his eyes. He repeated the question, and this time, she gave him a little nod.

“Say it!” he yelled at her. “Tell me you love it”

“I love it” she lied, barely above a whisper.

“Louder!” he yelled, giving her a thrust so deep her head hit the cab of the truck at the front of the bed.

“I love it!” she cried, tears streaming down her face.

“I knew it. I always knew” he said, as he finally pulled out again.

“Turn around. I want that little ass too.” He said to her, his cock throbbing in his hand.

She slowly turned around again, getting on her knees. Her face was buried in the blanket in the back of the bed, and her ass, her perfect little ass, was pointed up at the night sky, waiting for her boyfriend to do what he wanted with it.

“That’s it baby. Turn around.”

Dylan grabbed his slippery cock and pointed it at Sam’s impossibly tight ass. The screams that she let out when he ripped her pussy apart were nothing compared to this. His cock in her ass seemed to pull her out of her shocked, passive state, and return her to reality a bit. Dylan was burying his cock in her ass right here, outside, in the back of his truck. There was nothing she could do about it. She felt the head slide in, and she felt her ass stretch to try and accommodate him. It wasn’t happening, but he kept pushing anyway. She tried in vain to get away, to get her ass off of his dick, but the only thing in front of her was the back window of the truck. Dylan grabbed the hair on the back of her head and pulled hard, forcing her to arch her back and push her ass up for him. He pulled on her hair one more time and buried his cock to the hilt.

Dylan held his cock in place, his body rigid, bicep flexed, with his fingers full of Sam’s bright, blonde hair. This ass was beyond words. Tighter than anything could be, should be, would ever be again. He felt his cock start to throb at the base, and knew that his release, two years in the making, was finally coming.

For the first time in her life, Sam felt a man release his seed inside of her. She felt his cock swell and throb, felt it being pushed even more impossibly deep into her, and felt the warmth and wetness that was Dylan’s cum inside her ass. He pumped at least eight ropes of sticky, warm cum into her ass before he was spent, bellowing to the night sky while holding her head back by her hair.

Sam was powerless that night. She could do nothing but take it, so that’s what she did. She took every inch of his dick, and every drop of his cum into her ass.

Back in my office, the sky was dark, and all the lights were off. Everyone else had long since gone home, and it was just the two of us in my office. She was shaking and sobbing in front of me, this beautiful, broken girl. Upon closer inspection, I could see her wrist was still bruised from her ordeal, and she was constantly shifting in her seat. Her ass must have still been tender.

I refilled her water glass, and when she finally regained control of her breath, and the tears stopped, I looked deep into those beautiful blue eyes.

“Well,” I told her, clasping her hands in mine. “There is really only one thing I can think of to do right now.”

“What’s that?” she said, her voice shaky, holding back tears.

“Turn around”