Broken Courtesan by Lilitu

Chapter 1: Of the whore, by the whore:

Jacob was a whore. But he wasn’t always living by the nighttime, and indulging in his two hobbies: gay whoring and gluttony. He did not start out that way. He started out as a green, virgin young man with short sandy brown hair in his late teens.  Pale skin, tall, with a nice shadow on his face, a average looking nose, and thin lips, his bright olive eyes gazing at the horizon as he skipped to school with his best friend Louis.

Louis was about Jacob’s age. She was into anime and video games as he was. Both were sexually inexperienced and she had dated Jacob once. But of course that ended in disaster when he found out he liked penis and not vagina. That was a day that Louis never forgot. She came into the room he was at, as he sat on the computer and wrapped her white arms around him... As she brushed back her dirty blond hair through her fingers, she leaned over, and asked him what he was looking at through her over sized lips. Then she moved her pointed nose from his cheek and realized he was actually looking at gay porn. That was the end of their relationship.

“Hey, we should try to get the teacher to have sex with us.” Louis exclaimed while her flat chest jiggled through her yellow t-shirt.  “In a threesome?!” Jacob exclaimed, flushed red in the face. “Even better!” she said. “That way he could take both our virginities! Imagine if we didn’t have to be virgins any longer!” Jacob stopped and turned his head towards the ground. “We’re just highschool students, he would never... I mean... Uh....” Jacob whined. “Oh, don’t worry, we’re both 18! We won’t get in trouble!” Louis laughed. They both paused and stared at each other, realizing they were late for class, they both ran as fast as they could to the school.

Jacob sat in his English class, with a pencil in his mouth as his teacher gave the lesson. The blue walls of the classroom, the drowning of the teacher’s voice, the L-shaped desks all occupied with various people, many Jacob didn’t associate with as one of the unpopular students. “Louis had always desperately tried to be one of the slutty girls...” Jacob thought to himself as he gazed out the window. “I don’t think she could pull it off... I mean Mr.Anderson never seems interested when she flirts with him.... I wonder....? If I could, maybe... No, that’s wrong of me to think that. I was raised a Christian.” The thought had never left Jacob though. What if Jacob could be the town whore or school slut? What if Jacob had a chance? Make a name for himself? Actually do something with his life?

That was it. To Jacob, it was decided. It must be fate, this was his whore calling. However, he must muster up the courage to actually go through with it. Jacob, though, didn’t want Mr.Anderson in math class.  No, Jacob wanted someone much, much harder to get. The quiet authority that Mr.Bob, the older English teacher who was boring as hell. Mr. Bob was good looking, with his stern voice, his full burl black beard, short hair that he parted to the side... Mr.Bob had a stocky body... But underneath his prim and proper navy blue suit, Jacob imagined how his stocky body was.... Built for perfection... Curly black hair all across his chest.

Chapter 2: First experience:

The bell rang and classes let out. Luckily, English was Jacob’s last class. All the students in the room bolted for the door. Not Jacob though, he sidled, awkwardly over to Mr.Bob’s desk. “Yes, Jacob? Is there something I can help you with?” Mr.Bob said casually. Jacob could only look down at the floor. He didn’t know what to say. What could he say? How do people normally flirt? He had fantasies about his first time, but it was always with a random classmate. It was always a flat out “Let’s fuck.”.

“I... need to know how to get an ‘A’”. stuttered Jacob. “Oh? That’s all?” Mr.Bob’s gave Jacob a condescending gaze through his thick black framed glasses. “Well, then all you need to do is study. You know that as well as I do, Jacob.” Jacob flinched at Mr.Bob’s expression. “No.. That’s not what I mean!” screamed Jacob. Mr.Bob’s face turned to shock. “I mean... I... meant I need to ‘earn’ my A another way...” Jacob looked down as he quietly spoke. “A way which most people find shameful, but I find is my true calling.” Mr.Bob silently met his gaze with Jacob as he bent down. “What are you suggesting?” Mr.Bob glared at Jacob as he turned the opposite way to the black board.

“I want to exchange sex for a grade!” Jacob exclaimed. This played exactly into Mr.Bob’s hands. Little did Jacob realize that Mr.Bob was a closet homosexual. Mr.Bob had, had sex with many students and was giving out good grades for it. It was one of his pastimes. Now, finally, it was time for Jacob to earn that A, too. “Perhaps, he has heard the rumors at school?” Mr.Bob thought to himself. “But he just never mentioned them before.” Jacob had not heard those rumors, he was as innocent as a white lamb in a den of lions.

“You can earn it. But only if you’re good enough!” his voice got more raised as he said the last two words. Jacob sputtered out.. “But... but... I’m a virgin!” His innocent eyes looking into Mr.Bob’s. “This does not faze me. You will do as I say.” Mr.Bob’s stern voice echoed in the empty classroom. “First, Jacob bend over my desk and take your pants down...” Mr.Bob ordered. So, Jacob did. His pasty butt was in the air which was chilly that time.

Jacob was sweating as nothing was happening. But he closed his eyes and imagined that it was going to be painful, thus bracing himself in a tight face. “Don’t worry, I have lube.” said Mr.Bob. Jacob could hear the drawer to his desk open and the sound of footsteps. Then Jacob opened his eyes as Mr.Bob put his firm, big hands on Jacob’s butt. It felt so good, feeling the warmth of his masculine hands... His hands reached almost entirely over all of Jacob’s ass.”Ok, I am going to slowly put it in.” Mr.Bob explained.

Slowly Jacob felt pain in his butthole as the dick pushed through. Then Mr.Bob’s 6 inch cock got all the way up his butt. It was then that Jacob had an epiphany. His face turned red but Jacob realized how much he loved Mr.Bob’s juicy cock inside his ass. Mr.Bob started slowly thrusting, then he got faster and faster. This was the breaking point to Jacob. Jacob pushed back as he took the cock like a man. Mr.Bob was wearing down. But Jacob wasn’t finished. Mr.Bob could hardly believe Jacob wasn’t experienced. Though his tiny butthole proved that he was. It was so tight around Mr.Bob’s cock, it reminded him of the days of his youth.

Then Mr.Bob grabbed Jacob’s dick and started jacking him off. “Oh my god!” Jacob screamed over and over. This was a great feeling and both of them could easily cum. Faster and faster Mr.Bob thrusted as hard as he could...He stopped helping Jacob and he got slower and slower. Until finally Mr.Bob climaxed in Jacob’s ass, the white semen was drizzling out. “Oh, god this feels so good.” Jacob thought to himself. “I love cum.” Mr.Bob was so exhausted that he fell into his chair with his pants still undone.

"That.. That was good, Jacob. Your nice tiny hole is enough to earn that A” said Mr.Bob to Jacob. Still out of breathe, Jacob put his pants up and bowed to his teacher. “Why thank you...This is my new line of work.” Mr.Bob was flustered and then quickly got his pants up. “Now, you don’t go telling anyone about this... Y’hear!?” Mr.Bob looked embarrassed and angry, his face red because of both emotions. “Sure, thing.” Jacob smiled and walked out of the classroom with a satisfied look on his face.