Blackmail

**I did this for a fan who asked me to write a TG story. This is not my typical story, but I enjoyed writing it.**

Caleb Thompson walked into the cafeteria thinking about the next class and the ninety minutes of boredom that lay ahead. Math was his weakest subject and college level math was a chore for him. He just knew that a B in the class was all he needed and if he did get a C, he knew that he needed to get higher grades in the future to offset the low grade, but it was his last and only math classes needed to graduate. It was the start of the semester and he already knew it was going to require more effort than he put forth in high school.

Deciding to go to a community college was calculated not on wealth or grades. He remembered his father asking him where he wanted to go, and his options were Rutgers and Alabama. The unbearable heat of the South made it quite clear. It was the third option that Caleb enjoyed having that his father did not think of. His father was not prepared for him to ask for a car in exchange for a community college for two years and then promising to transfer. The cost savings of the college was equal to the price of the car. Caleb loved having his Dodge Hellcat now as it was his because of his plan.

Having a family of means was something that he knew distorted his viewpoint, but having nice things had a good feeling to it. His mother grew up poor and grounded him in the ideals that money is a tool and never to step on people without. With his father a surgeon, Caleb was inundated with lectures of a good education and the drive for something more.

As more students shuffled into the large college cafeteria, Caleb spotted something. He instantly recalled Elizabeth or Beth as she liked to be called from high school. Since it was a year ago, the memory was fresh in his mind as was all the details of what happened.

With her slim, petite features and tight leggings, she looked like any other cute college girl. Her hair was straight black and in a tight ponytail so it showed off her small neck. Caleb loved how her small ass had a perfect curve to it and at a few inches above five feet, she was the poster child for what a hot college girl should look like even though she had a secret he knew about.

Caleb knew he had to keep his guilty pleasures hidden from everyone including his girlfriend Paige. It was something that turned him on and was the fantasies of countless masturbation sessions. At first, it was a few minutes of a video clip and then it turned into a few movies, but as he got older his transsexual fetish turned into a video collection.

Living in a religious community had more disadvantages than advantages. Paige was only willing to give head and hand-jobs and talked about marriage like it was supposed to happen right out of high school. Her parents were big in the church and Sunday was an all-day religious ritual. Her parents routinely spoke out against gay marriage and anything they saw as against what they perceived as normal. Caleb knew his fetish for girls with penises would certainly fit into that criteria.

It was summertime and Mr. Lynch the principal of the high school was in his father's office. It was a large office that had a couch and a big screen television for their college football. They were in college together and watching football on Saturday was an every week occurrence. This was nothing new and Caleb thought nothing of it until he heard Mr. Lynch mention the word transsexual. He instantly stopped in his tracks and focused his attention on eavesdropping.

Hiding outside the office, he heard Mr. Lynch ask medical questions about transsexuals and the disorders and problems that could arise in a school. He then mentioned that a student was transferring in that was a transsexual and he wanted to know as much as possible. He did mention that the only people that knew was the board and him and was told specifically by the board to keep the matter quiet as the parents had a lawyer ready to go. The big information bomb came when Mr. Lynch said that this girl would only be in the school a year. She would graduate and then they would not have any worries after that.

Caleb remembered looking around for the new student the first day of school. He was taken back the first time he saw Elizabeth and knew she was the only new student at the school that was a senior. She had managed to fit in with the popular church girls. She also did not look anything other than another cute girl. She was not tall, and all her features were that of a cute girl. Her breasts popped out and her ass made guys look twice; only Caleb knew that between her legs was a penis.

The memory of his first and only interaction with her came to him in a flash. He had sat down at the lunchroom looking over at Beth as she was now in college and looking just as hot as ever.

It was in October of last year that he got the courage to confront her. The need to be with a trans girl hit him the moment he first jerked off to shemale porn. The desire festered into more and more videos and thoughts.

He recalled sitting at the lunch table in high school and the look in her eyes when he first con-fronted her. He knew it had to be blackmail even though he hated doing it; there were no other choices. He knew he had to blackmail her into putting out as a simple "Hey you're a tranny, come fuck me" would not work.

He walked up to her still wondering her reaction, but knowing he had to talk with her. "Hi there. You're the new girl...right?"

She smiled and put down her drink. "Yeah. I moved in from California."

"I need to ask you something," Caleb spoke, looking around; making sure nobody was in ear-shot.

"What is it?" she replied, giving a curious look as Caleb wondered if he had the right girl since her voice was so feminine.

"Do you like girls or guys?"

"What kind of question is that?" she answered quickly and with a tone of anger.

"I was just asking. I don't know if trans girls like girls as well as guys," he said, thinking that he knew there were lots of videos of shemales with girls. He figured he did not want to force some-one into doing something they would not normally do, although he knew he was still kinda forcing her.

Caleb saw the look of utter shock in her face like she saw a ghost. Her mouth dropped and he saw the fear in her body like she was about to have an anxiety attack or even worse, a heart attack.

"I was just asking because...well, you're hot. And I was thinking the two of us...you know."

Caleb was shocked at himself for admitting it and even scared that he told another person his most secret fetish. It was even worse for Beth as she had her entire life in his hands, and he knew it. He could play off the fetish, but she could not run away from the fact she was considered a freak in this town.

"You...you...you're going to tell people that?" she stuttered in fear as he saw the look of pure fear in her face like that of a soldier about to die or a parent that was watching their child die.

"I was hoping that I would not have to, and you would just..."

"No....no....fuck you. You're a real fucking asshole...fuck you. Nooo...nooo," she answered in tears.

A few people began to look, and he knew if he stayed to press her, it would lead to questions. He quickly got up and left. The rest of the day and the rest of the month he thought about his threat. He could destroy her life, or he could press her into getting sex. The look on her face was haunting him though. He hated causing pain and he managed to get a look from her that was now burnt into his memory. For the rest of the year, he kept the secret and wondered how he would apologize to her.

Caleb sat down at the lunch table thinking if he should go up to her and apologize now that time had passed, and they were both in college. She did not see him, but he could see that she was with a lot of people. Caleb then realized that there might be a better time and today was not a good one.

The next day Caleb had only one class and it was going to be an easy one. Biology came natural to him and getting an A in the class would not be farfetched. His father stressed science on him at an early age and he never got below an A in a science class ever. With his father being a doctor, it was something he felt was in his blood. Since the class was in his realm of study, he walked in confident that he could handle this class.

When Beth walked in, his heart stopped. It was the first time they saw eye to eye since that fateful day in the high school lunchroom. Her eyes quickly looked away, but he could tell that she saw him. He could not help but look to see that her ass looked absolutely stunning in leggings and he wondered if she was a trans at all or if she had surgery.

Caleb listened to the professor talk about the class and he skimmed the syllabus noting that the stuff being covered was not all that hard. It was more in depth, but nothing too bad. The lab part of the class was right after the lecture part and when the professor said there was going to be groups, he wondered if he was going to be lucky, or unlucky.

The professor called out groups and when Beth as assigned to him, his heart skipped a beat. Of all the odds out of a class of twenty that he would be assigned to her. Then he realized that her last name was Thomas and his was Thompson.

Caleb knew that she was going to argue or plead with the professor the moment she walked up to talk with him. The professor shook his head and he just knew that this was going to be an interesting semester. He knew this confirmed that they were in a group.

She sat down at the small table with him and gave a snarled look at him. "Don't, say a word about anything other than the assignments." Her sniffing told him that she was holding back tears too.

With a head nod, he knew he was going to honor her wishes. The urge to say sorry was almost on the tip of his tongue, but he decided to wait until the time was right. Knowing her anger was there only meant a confrontation if he said anything. The memory of her scared face still haunted him, and he knew that he would seek forgiveness to ease that memory.

The next class, he kept to himself and only talked about the assignments. He could tell Beth was struggling, but he picked up the slack and quietly finished the rest of the work that she was supposed to do without a word being said. They were the first group to finish and the professor remarked on both their speed and high grade. Caleb smiled knowing that it was easy and that he kept quiet as to not upset Beth.

The following week the groups were assigned lab work that required some of it to be done at home. Caleb wasted no time in getting his work done and when class time came, he could see that Beth had a difficult time with it.

"I could fix that for you. You are missing the DNA sequence and a few other things."

Beth gave a look of defeat and not anger. "I couldn't figure it out."

"Here let me," Caleb answered as he pulled the project paper towards him and began adding the missing work.

"Why did you not say anything? I always wanted to know why," she said quietly as to not let others hear the delicate conversation.

Caleb quickly looked up as he was adding the missing work on her chart paper. "I felt bad. I am sorry for what happened. I never said anything because I felt horrible about the whole thing. I really wanted to apologize last year, but felt it wasn't the right time."

He could see she was about to say something when he pointed to the paper. "You missed this one too."

As she looked at the paper, she then looked up again with a curious face, He knew this was his chance to apologize again in a more detailed way. "I wish I never said anything. I really am sorry about it. I never told a soul and never will."

Caleb then heard her soft voice break his concentration. "Thank you. Not just for helping me, but for not saying anything."

Still fixing her work and looking in the book, rushing before the professor walked around to them, he said back, "I wanted to tell you all last year that I was sorry. I was just curious and didn't know how to say it, so I used the blackmail route."

As the professor walked close, Caleb slid her work to her and then acted like he didn't do any-thing. As the professor was grading it, he looked at her as he gave her a B. Even though his pa-per was an A, and Beth got the B, he knew that she would have gotten much lower if it wasn't for him fixing the errors.

As the professor walked away, he liked seeing her smile. "Thank you. I spent all night reading and couldn't figure out how to do it."

Caleb loved how her voice was so feminine and it almost made him question the fact she was born a boy. From his limited medical knowledge, he figured it was either hormones, surgery or a combination of things.

The class ended and he went home with a fresh look at what he did in the past and feeling for-given about what he did last year in high school. The calm sense that he was forgiven and that he helped her out in return for what he did, seemed to equal things out between them.

The next class he walked in ready to get the next assignment. He looked as she walked in wearing leggings again and a small top that showed off her breasts. She was not busty, but defiantly had boobs that looked amazing. Her ass and legs would fool anyone and made him actively think about not staring.

Beth sat next to him at the lab table and her perfume hit him hard. She smelled like roses on a summer day and her makeup was subtly done to highlight her slim face. He turned to her wanting to be nice, but not upset her. "You look nice today."

"Aww...thank you," she answered back, smiling as he knew she did not take offense by it.

As the class continued, Caleb could tell she was struggling with it. She was having trouble with formulas and some of the wording. He gave her another caring look still not wanting to seem like he was hitting on her. "If you need help with this, I can help you after class. The lunchroom is free, and I can help you there."

"Thank you, but I have to be somewhere after class. Are you free tomorrow? There are free rooms in the library to study."

"Okay. I will be there tomorrow," Caleb said, knowing that this was for studying only and that his need to know more about her needed to be squashed.

The urge to ask about her physical features and her sexual habits ran through his mind all night long. He had a date tonight and was most likely going to get lucky, but his mind was so focused on Beth and what she was looked like nude.

At the library he saw her in one of the quiet study rooms that had a glass side so people could look in. It had her name on the side that she had it reserved for two hours. He walked in seeing she was wearing a skirt and a nice blue top that showed off her slender waist.

"I am really thankful you are helping me today. This class is my hardest so far," she said just as he put his books down.

"Ohhh, it's no problem. I am glad you forgave me, and I could help."

"That too. We all make mistakes and....well, you never told anyone, so it was not that big of a mistake," Beth said quickly as she opened the book as if the past was all but forgotten about.

Caleb quickly gave her a cheat sheet he used and showed her a better way to look up formulas and memorize them. She smiled often and wrote down everything he said just as it came out of his mouth. The two hours was almost up, and he was shocked at how fast and neat she could write.

Beth turned to him as her hand finally stopped writing. "I need to ask you something. It's been on my mind since last year. Did you really want to fuck me?"

Caleb knew that he was caught. He needed to answer her, but was afraid as his secret was about to come out. He could play it off as he wanted to fuck her but knew that being honest was better than trying to account for a lie.

Taking a deep breath and hoping not to be judged, he spoke as calm as he could trying to make it sound less weird. "I was...well I was watching porn and I wondered how it felt. You know...for a girl like you to... you know."

Beth gave a smirk as Caleb prayed secretly that she would not embarrass him. "So, you wanted to know what it felt like to have a dick in you?"

"Well yeah...if you put it that way. I am not gay or anything, I was just wondering is all." Caleb felt a flush of heat on his face from being caught.

"Does Paige know? Does she put things in your butt?" Beth asked, smiling as a person would once they found someone's secret.

"I never got that far....and God no I would never tell Paige. We are still dating, and I never told her that I like any of that. I just wanted to experiment," Caleb admitted almost feeling the guilt of his fetish being released as he told someone for the first time.

"I see. So, you wanted me to fuck you last year?"

Caleb did not know if she was teasing him or asking questions, but it felt more like teasing. The guilt came back to him a bit and knew that he needed to change the conversation. "Let's get back to studying."

"Ohhh...so you wanted me to fuck you. It's alright to admit it. Have you tried toys on yourself?" Beth calmly asked as her voice became softer and sweeter.

He also quickly thought about how the few times he had thought about buying a toy, but then chickened out right before buying it. Even ordering online was weird as the fear of his parents looking through the package and opening it would be too much.

"Let's talk about something else," he stated, wanting not to go further as it he felt the guilt of wanting something in his ass.

"Okay...I understand," she replied smiling and opening the book.

Caleb fell back in the routine of pointing out where she needed help before the time expired in the room. He knew he should have asked more questions and then felt the guilt of not asking her questions and telling her what he really wanted. The guilt faded and was replaced with the anger for having the guilt.

The next day in class was a test and Caleb easily finished. He was almost positive that he did not miss a single question too. He did look over and see Beth struggling and debated on helping her. Instead of just giving her the answers, he coughed when she missed one. It was subtle and he only did it for a few questions not to arouse the professor.

During the lab portion, the professor assigned a large project and Beth instantly looked at him. "Can we meet again this week for a study session?"

Caleb nodded his head and knew that it was a chance for him to ask her a few questions now. He finished the day and went home to prepare some study sheets for her. All he could think about was what and how to ask her sexual and personal questions.

Like before, the room was assigned and reserved to her. He walked in to see her wearing a simple shirt and leggings, but her shirt covered her ass, and thus ruined the sight of her perfect rear. He sat down greeting her and opened his bag to hand her the sheets.

"Ohhhh...thank you. I really do need to thank you for helping me out during the test. I should have known those answers too."

"It's nothing. I was glad you got the hint."

Beth quickly looked at the sheets and Caleb started quizzing her and helping her memorize the next chapter and then talk about the project. He waited for the right time to ask her and finally swallowed hard just as it was quiet, and she was writing something down. The close proximity gave him a thrill as her perfume added to her presence.

"Can I ask you a personal question?"

Beth looked up curious. "Sure."

"Do you like girls or guys? I know some trans girls like guys and some like girls."

"Both kinda. I have been with a girl before, but I prefer guys over girls," she answered as if the question was no big deal.