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Taboo High - The Virgin Part 1

Brady's student athlete needs some help.

Brady opened a beer and sat down on his couch ready to watch the game. With the state cross country finals completed last week, he finally had a day to himself to relax and watch some sports. As a first-year biology teacher and cross-country coach, it seemed like every waking minute for the last two and a half months had been occupied with work.

Just as he turned on the TV there was a knock at his door. Crap, he thought. Who would that be? When he answered the door, he was surprised to see Jennifer, one of his top cross-country runners. Just last week Jennifer had placed second in the state tournament.

“Jennifer, what are you doing here?” he asked. “More importantly how did you find out where I live?”

“May I come in?” Jennifer asked.

Motioning her for her to enter, he stepped out of her way.

“I have a friend that lives nearby, and I saw you one day on your balcony. I came by because I need your help.”

“You really shouldn’t be here. Why don’t you stop by my office tomorrow after school and we can discuss whatever it is you need?” He told her.

Jennifer’s cheeks turned red as she replied, "Well…. Um… It is something personal that cannot be solved at school.”

That comment caught Brady off guard. What could she possibly want that could not be discussed at school? Against his better judgment, he motioned for her to sit down on his couch as he sat down in his recliner. He could tell she was nervous which peaked his curiosity.

“Well, what is so private we cannot discuss it at school?” he asked.

Jennifer looked down at her fidgeting hands for what seemed like forever.

“Um, Homecoming is next Friday and Tim has rented a room for us after the dance,” she finally replied

“Okay, do you not want to go?” Brady asked.

Finally looking up at him Jennifer Blurted out, “I heard you and Brooklyn last weekend.”

“Oh”, was all he could say. What he really wanted to do was panic but that was not an option right now. Instead, he just stared at Jennifer waiting for her to continue as what happened went through his mind. Last weekend he took Jennifer and Brooklyn to the state cross country meet several hours away. They left on Friday, spending the night in a hotel, for the Saturday meet. That night Brooklyn had pushed her way into his room and the two of them had sex.

Jennifer went back to staring at her hands. “Brooklyn also told me what you did was incredibly hot and…”

“Ok Jennifer, enough beating around the bush, what are you here for?” Brady asked in frustration.

Jennifer looked up at him with a look of determination.

“I am a virgin and nervous about having sex with Tim. I don’t want to do anything wrong or ruin it. I guess what I am saying is, I want you to teach me by taking my virginity.”

Brady sat there dumbfounded for a moment as he tried to gather his thoughts. What Jennifer had just suggested was totally inappropriate. Of course, so was his night with Brooklyn. Despite all of that he could feel his cock begin to harden at the thought of taking Jennifer’s virginity.

“Why would you want me to be your first? Tim is your boyfriend. I promise you, you will not do anything wrong.”

“But I have heard your first-time sucks, especially if neither of you knows what you are doing. I want to my first time to be with someone who has experience.” Jennifer replied.

Despite Brady’s dick swelling at the thought of popping the teenage cherry in front of him, he decided to take the high road.

“Jennifer, I am honored by your request but I don’t think I am the right person for you, especially for your first time. Your first time should be gentle and loving, with someone who loves you. If you are worried about having sex with Tim, then you probably shouldn’t. When the right person comes along you will know it and not be worried about it.”

“That may be right about Tim, the thing is, when Brooklyn told me about the two of you, it totally turned me on. I want to lose my virginity to an experienced man who knows what he's doing.”

Brady paused for a moment and gathered his thoughts. “Look, Jennifer, I am typically not a loving, gentle kind of guy. I like it rough, with me in total control."

“I know, Brooklyn told me you were rough and that turns me on. Replied Jennifer."

Giving in to the beautiful tempting teen in front of him, he looked over at her and told her to stand up. “Jennifer, I need you to listen to me. If at any time you want me to stop what I am doing, all you need to do is say so. Do you understand?”


Brady took a moment to admire her. He knew from her athletic stats that she was 17 years old, five foot seven and weighed a mere one hundred and ten pounds. Today she was wearing a pair of four-inch wedge sandals, skinny jeans, and a purple printed shirt. The shoes and pants did amazing things for her legs and the blouse was unbuttoned down to the area between her breasts. She had long brown hair that was currently pulled over her right shoulder.

“Turn around please,” said Brady as he made a circular motion the finger of his right hand.

When she was facing the other way, he told her to stop. He took a moment to admire her tight little ass in the equally tight jeans.

“Please take off your blouse.”

As Jennifer turns back towards Brady as she begins to unbutton the blouse.

“I didn’t tell you to turn around.” scolds Brady.

Jennifer looks at him and lets out a huff in exasperation. “Why are you being like this?” she asked.

“Like what?” Brady asks as he stood up and quickly walks over to her.

Not waiting for a reply, Brady grabs a handful of her hair at the back of her head and pulls her head back so she is looking up at him. He then proceeds to kiss her roughly on lips. His tongue pushing against her lips to gain access. Jennifer parted her lips and he shoved his tongue deep into her mouth. After exploring her mouth for a moment, he broke the kiss.

“Look Buttercup,” Brady said, “when Brooklyn came into my hotel room last week, she poked the lion. Today, you have stepped clear into the lion’s den. I told you I like control. I expect you to do as I say when I say. I reserve the right to tie you down to my bed and do as I please. I will promise you that when I slide my hard dick into your tight virgin pussy, I will be gentle and loving but until then you do as I say. If you are not up for that, you know where the door is.”

Brady let go of Jennifer’s hair and half expected her to run for the door. Instead, she reached up and kissed him. This time it was her tongue doing the exploring. Breaking the kiss, she slid down onto her knees and reached for the waist of his gym shorts, pulling them down. His boxers came next with her helping him step out of both. Jennifer reached up and grabbed his throbbing cock with her right hand and began to slowly pump it.

“Your cock is bigger than Tim’s,” she said as she continued to pump it.

“You have seen his cock but never had sex with him?” Brady asked.

“Yes,” Jennifer replied. “I have given him hand jobs and one time a blowjob. But that is it. He has never seen me naked or stuck his hands under my clothes.”

“Mm, I look forward to seeing you naked but first, show me your blowjob skills.”

Jennifer did not say anything, her tongue curling out of her mouth and swirling around Brady’s cock. With the head of his cock wet and ready, Jennifer let go and spit into her hand. Jennifer used the spit in her hand to rub up and down his shaft as she also licked its entire length making sure it was slick with her saliva.

Jennifer looked Brady in the eye’s as she slid the head of his cock into her waiting mouth. Jennifer’s eyes were large, gray in color with sparkles of blue intermixed. Right now, they had a glint of mischief as she began to pump his cock with her hand while sucking him into her wet mouth. Brady let this continue for a few minutes as he enjoyed the incredible blowjob she was giving him.

Brady decided it was time to step up the game a little more and told Jennifer to let go with her hand and take off her blouse. As Jennifer unbuttoned her blouse, Brady began to slowly pump his hard cock into her waiting mouth. He went a little deeper with each stroke. Once her blouse was off Brady then told her to reach behind her with both hands and grab her elbows. She was not to let go of them until he told her to.

The bra she was wearing was a paler shade of purple than her top and mostly lace. He could just make out the outline of her areolas under the lace. Her breasts were certainly not large but looked beautiful all the same.

Brady grabbed the hair at the back of her head and began to slowly pump his cock into her mouth, going deeper with each stroke. He was amazed at how deep she took him before finally choking on his girth. When she did gag, he pulled out, a stream of gag juice following and dripping down her chin. As Brady continued to fuck her face, her eyes watered up causing her mascara to run down her face and her saliva dripped down her chin onto her neck and chest.

“I am about to come,” Brady told her. “When I do I will let go of your hair. You can either take my load in your mouth or on your face, you decide.” Jennifer nodded and picked up the pace. Brady may have been holding her hair but she was the one in control.

After a couple of minutes, Brady could feel his orgasm approaching. He let go of her hair and told her he was about to come. Jennifer pulled off his cock as the first load of cum shot out. It hit her on the cheek, leaving a trail of cum across her eye, forehead and into her hair. With a look of surprise, she quickly wrapped her lips back around him. He shot several more loads of cum into her mouth as she continued to suck him.

Once he was finished he pulled out of her mouth and reached down to pull his shorts back on.

Looking at her, she was quite a sight to see. Her chest, neck, and chin were covered in saliva. His first shot of cum was running down her face, mixing with her tears and Mascara. At the same time, she had a look of lust in her eyes.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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