Living the Life of Rylie

The Rosewood Community College football team bonfires were legendary and had been so for years. It didn't matter if it was football season or not, if you got an invite, you went. Dozens, not hundreds of people showed up but the small crowd is why they were so good. Local 18 year old high school girls, recent alumni, or fun party people from the area were frequent attendees. Held randomly like a flash mob, if you got the message you tried to go so your spot wasn't given away next time. The one thing that the bonfires were strict about was the guard- If he didn't know you he checked your ID and you showed him your invite on the phone and then left it at the gate. Absolutely no one under 18 was allowed and neither where pictures. They didn't care that the drinking age was 21, no one at Rosewood C.C. was 21, but if and when these parties turned into an orgy, no one wanted to be charged with statutory rape.

Rylie Baker was a local high schooler in her senior year that fall and was almost 19. Not the best student in her class, she was known for her beauty and athletic prowess. Already promised a scholarship for volleyball at the large Division 1 university nearby, she had everything going her way to escape the town of Rosewood so a beer bash bonfire was the last place she should have been. But Rylie was a bit of a whore, liked to party, drink and fuck. Because of her athletic ability, she could go all night. Because of her lithe and toned body, blonde hair, gorgeous face and sex skills, she was in high demand. Her lack of morals made her open to anything and after her third bonfire and the fact she had three willing holes to score in, she earned the nickname "Hat Trick". Usually by the end of the night one of the guys would take her "tight end" and someone else would get her "wide receiver" and another would fill her mouth.

One particular night went wrong for Rylie. While being passed around the fire one of the players didn't bother with a condom. And then another decided not to use one also. Several loads later and a month worth of nervousness, Rylie decided she needed to make some life changes or she would never play D1 volleyball.

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Doug Simmons was, or had been anyway, a young, idealistic dreamer who went to college to become a science teacher and spent a year with ProgressCorps For A Better World, a group that sent him to blighted areas around the country, having him work for next to free while providing room and board and promised to pay off his student loans. Then, after a year they would get him a teaching job in a state that promised to pay down or pay off the rest of his student loans for a 4 year teaching commitment at one of the state's less desirable schools. Fresh out of college, Doug was going to change the world, but he quickly saw that the world needed more help than he could give it, or maybe it just wasn't worth saving. Moral decay, violence, hatred- he decided people sucked and the good people were far outnumbered by the bad ones. He also decided name, ethnicity and status had nothing to do with it. As a science teacher, he was familiar with the "Nature versus Nurture" debate, and if genealogy was nature, then nurture seemed to win almost every time. People got into bad groups and spread their awful behavior like wildfire, and that sad fact left him jaded. To put it bluntly, he just didn't give a fuck anymore. He was going to teach long enough to pay off his loans and then use his science education to land a job where he could make money. Today's students were bad, but even worse than them were their parents.

And this year at North High School in Rosewood is where two paths would intersect, changing their lives forever.

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North High was diverse racially, ethically, and economically both with students and faculty. It was perhaps one of the best cross sections of the entire country. Not a huge school, it only had 600 kids in its high school. Some were well known and some would make it four years with most teachers never learning their names. Rylie of course was well known because of her athletic skills. An outstanding volleyball player she also held school records in track and softball. Curtailing her sexual appetite since her last bonfire and not drinking lately, she turned to other vices. Security sweeps of the school were narrowing down on the substance abuse offenders, but not all had been caught nor would they ever all be caught. But Mr. Simmons knew better how to catch a sneaky person than the 85 year old security guard did, and he laid a trap, and like a great night in hockey, he scored a Hat Trick.

Had the stars lined up differently, Doug Simmons could have fallen madly in love with Rylie Baker. She was talented, graceful, gorgeous and seemed much wiser than any other high school senior or girl he had even dated in college. And only 5 years separated them in age. A big gap now, but in 5 or 10 or 50 years it would be totally insignificant. But out of all of the people he had ever met, she seemed as morally bankrupt as any, and he didn't even know the half of it. No one at North High did.

He knew someone had been vaping in the locker room during 5th period which coincided with chorus, lunch, study hall and P.E. and since it was a time when people came and went and no one had science class, he set out to trap them. He set a tiny camera up in the boys locker room entryway along with a tiny sensor, both hooked into an app on his smartphone. If he got caught, he would probably end up in jail even though he would not be able to see anyone naked in there. Cameras in a locker room were bad news, but this way he could monitor who came and went, and when the sensor detected certain chemicals, he could go in the locker room and bust whoever it was. And as a male right next to the locker room, he could explain a reason as to why he was in the boy's locker room.

He hadn't expected to see Rylie go in there.

He watched and for three days in a row as she entered the boy's locker room and then his chemical detector would silently go off. He knew he had the culprit. He should have turned over he evidence, but with the camera, he would be in trouble. The sensor was no big deal, but was proprietary and something he developed himself and didn't want to give it to the school. And he knew a little about her reputation and since she was almost 19, even though he would get fired for fucking a student, he wouldn't go to jail if it went that far. But he could still hope and blackmail.

So on Thursday his camera and phone alerted him to Rylie's presence in the locker room, and 4 minutes later his sensor detected chemicalized vapor, so he did a recon and found the area clear. And he took notes. Friday, the same thing, Rylie, vapors, no one. He did this for the next week and Thursday he had formed a plan. After school on Thursday he put a barrel lock on the locker room door and changed the direction of his camera to watch the hallway better and knowing that no one had gone near the locker room during her vape break, he waited. Security protocols in place, just like clockwork Rylie came down the hall and presumably went into the locker room. 4 minutes later Mr. Simmons had his sensor go off, and 3 minutes after that, he entered the locker room and locked the door.

He heard scuffling and running water and realized it was coming from in the showers. He then said in a commanding voice, "Allright you boys, get out here. What's going on?"

No one came out, so he warned, "All right, on 'three' I'm coming in. One, two..."

"All right, I'm sorry. I'm coming out," Rylie said.

He didn't talk to her much since her class participation was not great, but with her sexy, womanly voice she had a future in phone sex, and with her body, a future in porn. He knew what her grades were and was vaguely familiar with her reputation and figured when college didn't work out for her, porn is where she's end up anyway. Hell yeah, he'd watch her.

Rylie came walking out, completely naked, still dripping wet. Mr. Simmons was speechless, which is what Rylie had hoped for, gaining the upper hand. She looked right at Mr. Simmons and said, "I had an accident at lunch and needed a shower. Now you invaded my locker room and I'm telling."

"Um, uh, go ahead, Miss. This is the boys locker room and I'm allowed to use the restroom and you are not. Also," taking a big whiff of air and not smelling anything, he said, "I happen to smell smoke. I think reporting this to the principal, getting you suspended will probably ruin your Division 1 sports career and scholarship, won't it, Miss Baker," he said with more authority than he felt. The fact that she was naked, and she had been able to see how hard he was, and he didn't expect her to be naked really put him at a disadvantage. Even though he would not soon forget the visual of her perfect body, he was wished she would have been clothed.

"Oh, no, you want to tattle on me? Oh, no, what will I ever do," she said in a mocking tone. "Do you think Dave will care that I'm vaping? I'll just suck his cock again and all will be forgiven."

Doug just stood there dumbfounded. Was "Dave" also Dr. David Johnson, the principal?

"Yes, Mr. Simmons, I sucked off the principal to get out of my last suspension."

Oh shit, Doug was in over his head, and they both knew it. She had him in checkmate and he needed a lifeline. And then Rylie threw him one.

"I'll tell you what, Mr. Simmons. You saw me naked, now show me yours. If you let me suck it and then shower and don't tell on me, we will keep it between you and me. You've seen Dave. You can imagine I would rather suck your dick than his if I am gonna suck dick anyway."

Still not sure of what to do, Rylie came up to him, undid his fly and his his cock sprung out. She undid his belt and pulled his dress slacks down and went to work on his manhood. She slurped, sucked and massaged his balls. When she could feel his sack tense up she finished him with a twist, giving Doug an orgasm like he had never experienced before. Then Rylie stood up, opened her mouth revealing a mouthful of Doug's cream, gulped, swallowed, showed him an empty mouth, and kissed him on the lips.

"Don't just stand there, Simmons. Pull your pants up and get out of here before you get fired," she told him before doing an about face and walking back into the shower. Doug noticed her backside was as magnificent as her front side.

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Rylie went back into the shower and collapsed. No, she had never sucked off the principal, but Mr. Simmons didn't know that and he could hardly ask Principal Johnson about it. Mr. Simmons had been correct- if she got suspended she would lose her scholarship and her one chance at escaping her crappy life. And Mr. Simmons was going to help her do it by keeping his mouth shut, and she had ways to persuade him.

She went to the office, pretending to be sick. While waiting in the office finding Mr. Simmons' full name and address had been no problem and then she left school. She had at least 3 hours before Doug Simmons would leave work so she did a little shopping, changed her outfit, did a little body maintenance, then waited outside Doug's apartment complex where she was inconspicuous yet she could see well.

At 5pm Doug came home. Supposedly he had no roommate and no mention of a girlfriend, but that didn't bother her. She gave him about 5 minutes, went upstairs to his door, overnight bag over her left shoulder, high heels and tight bluejeans. She knocked on the door, saw a shadow through the peephole, then heard the chain slide and the deadbolt open, followed by the door opening.

"Uh, hello Rylie. What are you doing here?"

Not answering him she pushed her way in the apartment and said, "So, Doug, what have you got to drink? It's Friday, and you still owe me."

"Owe you what?"

"Oral, maybe more," she said as she opened the fridge. "Ugh, beer. No thanks. Got anything...harder?"

"Rylie, I uh, don't think..."

"Okay Doug, we are almost the same age and I KNOW you liked what you saw today and frankly I would like to see more of you, too. So unless you have some cinnamon schnapps or stuff to make Sex on the Beach drinks, you had better go to the store before I change my mind. You fly and buy, and I will get ready."

The liquor store was just a block away so Doug hurried. He bought several bottles, threw his money up on the counter and didn't even grab his change and hurried back. He stood outside his door until he had caught his breath and then went in.

Rylie was in black stockings, garters, a shiny black bra, and black panties with more open space than fabric. And to top it off she had her heels on. In her hand she had a personal massager and was working herself over.

"Want a drink now or later, Doug?"

"Later...?" Doug said, clearly not knowing what to expect and how to behave with this sexual goddess who also happened to be a student of his.

"Then come over here, Doug, you owe me oral."

Warning bells were going off, but all the blood flow from Doug's brain was in his penis, and all he could picture was what Rylie looked like naked- tall, tanned all over, fit, very little body fat, a line running down from her just below her sternum to her navel, but not really a 6 pack of abs, but sexier. One thousand percent feminine! Maybe Doug would be in her latest porn movie. No, that had to wait a year before it could go public.

Oh crap. Movie! "Rylie, where is your phone?"

"Why?"

"Because we cannot get caught doing this." She pointed to her phone, he took it, held his up and showed her that he put both of them in a drawer in the kitchen. Then he came back to the couch and the buffet she had prepared for him.

Here she was again, legs up in the air as some guy was going to have his way with her and not please her. He would be rough, fuck her, and give her little in return. Why did she keep finding herself in these messes? Why couldn't she escape this pattern? All she wanted was a chance, but then she did something stupid like getting pregnant or now, getting caught vaping at school. It didn't matter that it was legal for her to do it at home, it was wrong at school, and now she was going to have to take her punishment yet again.

He got down in front of her, and he gently played with her lips. He stuck a finger, then two, inside. He worked them around, massaging her walls and rubbing her G-spot. Then he put his tongue down there and sucked her lips, and then licked as much of her wet pussy as he could and mixing that up with sucking on her clit.

"Oh God, that feels soo... wonderful!" Rylie cried. Other guys would run their tongues down there but only to make her wet enough so they didn't chafe when they plunged in. They went down on her for their selfish reasons but never for her. Doug was doing it because he wanted to. And she thought he seemed pretty damned good at it.

"You said I owed you oral, Rylie. Is this what you still want?"

"For now...oh oh, OOOHHHH here it comes. I'm gonna..."

Her body spasmed. She bucked and kicked and he kept his mouth firmly on her clit for what he thought was at least 8 seconds, then he let off. He said, "I call that 'playing rodeo'. I wanted to see if I could hang on for 8 seconds. I won."

She gasped, "I think I won. That was fantastic! Well, Cowboy, tie me up and fuck me like the stud you are! But I need you to stop playing around and fuck me now."

In her overnight bag she had handcuffs and some light bondage toys, but Doug didn't know what to do with them. Truth be told, Rylie didn't either. But Doug did know what to do with a gorgeous woman in sexy lingerie. Her left leg was on the back of the couch and her right leg was on the floor. He lined up and slowly slid inside her.

"Oh Doug, that's wonderful!"

Then he stopped and pulled out. "What- what are you doing?" Rylie pleaded.

He picked her up and carried her down to his bedroom and gently laid her down on his bed. "Stay dressed, I will be right back."

He went down and retrieved her overnight bag, and sure enough, she had several boxes of various condoms inside. Back in his bedroom, he pulled them out. "Flattered, but I am not an XL Magnum. Hmm, fruit flavored, or super ribbed? What is your choice, Rylie?"

Why was he giving her a choice in his pleasure. She had begun to think of herself as just a receptacle, a cum dumpster for older men. If it was fun for her, great, but she basically existed for their pleasure. Now Doug was giving her a choice.

"Mmm, flavored, THIS time. Next we will try ribbed."

He took out a strawberry flavored condom, tore open the package, and rolled it down his shaft which was sticking out of his unbuckled pants. And as he finished undressing, his cock would wiggle. She wanted to laugh but didn't for fear it would ruin the moment.

He looked expectantly at her, allowing her to present herself. She got up on her knees and presented her backside to him, allowing him to choose which hole.

He chose the one she hoped for, the one that he had made feel amazing only a few moments ago. As he sank in slowly, he grabbed her hips and pulled her back. He loved how strong her glutes and hip flexors were. She was a machine, made for sports but allowed to fuck. She clinched her Kegals and he could feel her insides start to quiver. As she came, he said, "Oh Rylie I'm gonna..."

She quickly pulled him out, spun around, snapped the condom off and took him into her mouth in the blink of an eye. He was amazed at how fast she did that. He emptied his balls into her throat for the second time that day. Then, she held on, playing 'rodeo' with him. He was getting dizzy and then she pushed a finger into his ass hitting a nerve that caused him to have another ejaculation down her throat. She held on to him for nearly 20 seconds. She let go, and he collapsed. Utterly spent, and seemed unaware for a moment. Eventually he refocused on the lovely beauty next to him as he said, "Whoa. I think I know what you mean. I think I won that round."

"You tasted like strawberries from the rubber. Want to see if I do, too?" Rylie asked, hopefully he would.

Not too reluctantly he licked her and she tasted like a hint of strawberries, latex, and her own musky flavor. Her scent was intoxicating and he could live on that flavor forever. He gave her a small orgasm and then crawled back up next to her. He looked her over and said, "My God, you are beautiful. Can I get you to take off your lingerie, please? It looks great, but I want to see and feel all of you."

Did he ask her something and then say "please"? Men didn't do that with her.

"Will you help me take it off?"

"Mmmm, of course," he said. She stood up, and he got behind her and slowly unhooked her bra, then let is drop onto the floor. He reached around and gently cupped her breasts, and he softly kissed her neck.

"Ahh," she let out a soft moan. "More, that feels so nice," she asked wantingly.

He ran his hands down her sides to the top of her garter belt and stopped. She waited expectantly as he noticed her goosebumps. Then his hands ran over her sweet globes as he marveled at their shape and firmness. They were perfect. He went lower, touching her stockings, unhooking the backside clips releasing them from the now-dangling elastic bands. Then he slowly turned her around. He had knelt down and was lined up with her midsection so he undid the front clips. Now he was able to slowly pull the garter belt down and she stepped out of it, taking one step back toward the bed. Next came down the panties, exposing her shaved area and wet magnificent lips to him once again, and he saw her tremble ever so slightly, and once again she took another step back towards the bed. He breathed in her scent, and leaving her in nothing but stockings he reached out with his tongue and licked up her folds, and she buckled at the knees and he guided her the remaining step back to his bed. She involuntarily opened her legs, spreading her lips open for him yet again and he licked her pink honeypot. She was dripping wet, the anticipation of what was to come had her excited, and the concern a man showed towards her for once had her bewildered for the most part, but she was going to enjoy it.