Humilated Pleasures-Chapter 3

Story by Falcon3268 on SoFurry

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#3 of Chapter Commissions

Update editted version: Thank you lscin for editting the chapters. Nothing much happening in this one however you find out why Elizabeth is so interested in supposively in helping Jamie. More to come and the plot really gets thrown together in the next chapter. evil laugh


CHAPTER 3

She walked across the marble floor, heels clicking, as her eyes fixed upon her target. He was starting to stumble around, hitting the lockers either side of the hallway in a state of shock. Elizabeth allowed a sinister smile which superficially appeared kind and warm. Normally she would not have bothered offering to check up on a loser such as Jamie. However this was different, she had a personal interest in this.

You see, Elizabeth was what most people would call a spoiled brat. Her parents got her everything that she wanted ranging from fancy clothes to flashy sports cars. If she wanted to, she could get the captain of the football team in her bed, but that normally went with her looks which went with this area. Elizabeth was not what you would call book smart. Normally she would get someone else to do her work for her, usually pikcing out the nerds to do it, promising something special if they made sure she got an A+.

But the problem she had was with one particular class the nerds ran dry. Jamie however was a potential candidate for the role of "study buddy". So like her other classes, Elizabeth had gone about broaching the subject with Jamie in her usual manner; showing a little cleavage goes a long way with most boys. However, it seemed that Jamie was a lot smarter than some of the geeks she had met in the other classes. Or maybe he was just not quite so desperate to get his hands over tits like hers.

Taken aback in shock and surprise by being rebuffed by any boy, Elizabeth felt her expression harden. However she was determined to get a passing grade on this class. Normally something like this would not be one of her priorities, but her parents had promised to take her on a European vacation if she continued to get high grades. Approaching Jamie once more, she offered to give him anything -within reason- if he would simply do her assignment. And again her, adding a comment about her being a spoiled brat leaving her fuming in anger.

There was no one else in the class who could help her, but Elizabeth still tried to find someone on such short notice to no avail; ultimately she had to do the work herself. Giving in and going about getting all the relevant notes and books that she could find, Elizabeth tried her best to get the assignment done on time. What made it even worse was that she had cheerleading practice to attend to nearly every day and a big game was coming. Though honestly she was sick of being the head cheerleader, but the others were looking toward her to make a good example for the freshman cheerleaders that want to make a career out of being cheerleaders for major NFL and NBL.

Try as hard as she might have, Elizabeth still found herself struggling with the due date for the assignment to be turned in drew near she found herself making up, or even copying things from the book just to complete it in time. Nevertheless, after working on the assignment as hard as she could, she failed the assignment with the professor commenting that she appeared to have barely put any time into the paper.

When her parents found out, they were furious as they had always previously thought she was a prodigy. They called off the trip and insisted she spend time studying to make up for this disappointment. Her mother was more sympathetic to her trying to explain herself, but her father would not change his mind and they stood united as parents should on the issue.

Her parents were going on their own private vacation instead of the one they had planned for all three. Elizabeth was left with retaking the entire course. What made it even worse was that her parents had hired a tutor. When she learned who it was she balked, for on recommendation from the professor they had decided to let a fellow student tutor her: Jamie.

Jamie arrived on time the night she learned it was him. Her parents asked him what he intended to do to make sure she would catch up with the rest of the class. He assured them he knew what to do and had received notes especially from their professor. Both parents felt assured to leave their daughter under his capable tuition; but she most certainly did not.

Elizabeth could barely keep her rage contained, for it was not simply the fact that she had been given a tutor. No, the part that really irked her was the injustice, she felt so anyway, of it being the very guy she had looked for help from in the first place. She sat there through the first session, just glowering as Jamie rabbeted on about preparation work and research methods. But the gears started to turn in her head as she remembered hearing about problems Jamie was having on account of his figure.

The girl craved for something more than mere insults or general humiliation. Fortuitously, for her and not him, Elizabeth's mother works for a pharmaceutical corporation. She remembers hearing during one dinner that her mother had started work with a new synthetic estrogen product. Normally such things are used by transgendered people; but maybe such a thing could work for Elizabeth. A cunning plan hatched that very night.

The next day she contacted her mother, who had only just arrived at their hotel room, and asked about the drugs. It took awhile to squeeze the information out of her, but a daughter has her ways. She figured out that not only was her mother working with the substance, but had samples in her personal pseudo-lab down in the basement. With a little sniffing around she should be able to find it before they return home.

When they did return Elizabeth had proven to the professor she had caught up with the rest of the class. Her parents thanked Jamie for his efforts and paid him double on what they had agreed upon. The real kicker was that the money came out of what would have been Elizabeth's own allowance. That sealed his fate as far as the spoiled brat was concerned; no regrets about what would happen to him. But first, like any typical brat, Elizabeth broke down in front of her mother.

Good old mom confided that she thought her father was overly stubborn. In fact she went as far as to doubt his decision making skills, considering she is the more academically capable of the pair. Elizabeth felt a little better after this mother to daughter talk, but it did not change her planning on what to do next; and it is good that she can rely on her mother as she may need some parental help later.

Though before she even began her little plan Elizabeth started noticing odd behaviour from Jamie. Of particular note were twitching, prolonged glances toward the male students of the classroom. Then something telling happened as she caught a strange smell coming from Jamie on an otherwise normal day on the campus, and she smiled knowingly.

The scent was unmistakably of a female period just starting. Something that should definitely not be coming from Jamie. Maybe there was more to him, something even more easy to influence and expand upon for Elizabeth. This thought made her laugh a little as she approaches a multi-sex restroom. When the architects designed the college, they added something rather unusual in making the last restroom multi-gender. Some people think they were just having a laugh when they did that.

As she opens the restroom door, the girl could hear something wholly terrible. Screaming and wailing, mixed with a light sprinkling of groans, was coming from inside. She had followed Jamie here wondering when this would happen. Time to confront him and see if it is true.

Elizabeth turns the corner and narrowly ducks a metal bin flung over her head. It bangs against a wall and rolls onto the ground.

"Jamie?" No immediate response leads her to try again. "Jamie? It's me, Elizabeth. Are you alright?"

"Elizabeth?" a voice that clearly sounded shaken not by her sudden appearance but by something else. "What are you doing here?"

"The professor and others were worried about you, so I offered to see if you're alright. Are you... alright?" Elizabeth explained, her voice sounding sincere with her true motives hidden with practised ease.

"Okay? Am I okay?! Hell no! I'm in pain... I've got cramps, there's blood between my legs and I've had these weird desires for... for..." Jamie answers sounding distressed as Elizabeth stepped around the corner to find a startling sight. Standing there with a look of confusion and anger plastered across his face, with his clothing in tattered ruins and blood staining different areas.

"Easy there Jamie, everything will be okay." she said whilst stepping forward and wrapping her arms around him, trying to soothe his fears. However it was clear that it would be not be that easy. But she had time, and this was only the beginning.

"Alright? Are you blind or something? I am bleeding and my body is in revolt! How can everything be alright?!" Jamie cried out, clearly suffering from anxiety and confused about the entire thing. Elizabeth had to feel somewhat sorry for Jamie, but that emotion did not change the fact that she wanted sweet revenge. But now she needed to lure him into her trap.

"Come, I've got an extra set of clothes in my locker in the gym that you can borrow." Elizabeth said whilst trying to reach down to help him up. He had fallen down due to the shock and an intense physical fatigue he was feeling. But he jerked his arm back and looked at her with distrust.

"Hell like I am going to trust you! Knowing your reputation, you'd rather humiliate me for the heck of it than help me!" He hissed out through gritted teeth, trying to hold back the pain that the cramps were inflicting upon him.

"Come on, what choice do you really have? Also, who is going to recognize you in my clothes. With your figure you really could pass off for being a girl and they'd probably think you were someone knew."

Elizabeth explained with solid reasoning, never losing her cool no matter how repugnant she found Jamie. Normally she would just leave him there to be found by someone else. Someone who would probably take great pleasure in doing whatever they want with him. And if they ever figured out what she knew Jamie would probably end up being pregnant by the end of the day.

"Hey now there is a thought." Elizabeth was grinning on the inside. Her short term goals coalescing to server her fiendish long term plan. "Listen, my mom's a doctor and if you come with me maybe she can help you figure out what's going on right now. You know her, she will keep it all strictly confidential."

Jamie stood there whilst considering his options that he may have at this point. Although he wanted to avoid having any contact with the cheerleader bitch, at this point he had little choice but to trust her and would just try to forget about all of it afterwards. "Alright, let's go, as you said; what choice do I have?"

"Good, now come on lets get going. The classes aren't all done yet so not many people will be around." Elizabeth said whilst moving back to the door, knowing that Jamie would follow her like a lost little puppy. Opening the door carefully, she takes a moment to check the way for anyone else. Then she allows Jamie to walk past, his half naked and bloody self quite a sight.

They both moved as quickly as they could, whilst not rushing to draw attention from anyone at a distance. Thankfully the locker room for the cheerleaders was relatively close by and they made it there without any confrontations. Elizabeth closes the door behind them and considers locking it, but then decides not to as that might in and of itself draw suspicion. She will just have to train her new pet whilst keeping an ear open for intruders.

Rushing a little now, Elizabeth gots to the locker and opens it so jerkily that she almost snaps the key. Her hands are shaking, not from fear but of excitement. She calms herself and takes out the uniform. It is gold and red, the colours of the college sports team. However the clothes faded from time and wear, but they will do just fine.

"Take off those clothes, they aren't any good for you now. Then start by putting these on before someone comes in here and finds you in the locker room. Of, and begin with the bloomers then the sports bra which will add to the effect."

Jamie was grumbling constantly at this point. Memories of his mother dressing him up inappropriately surfacing once again and he feels a little sick. But such sensations are nothing compared to the cramps he is enduring, and endure he will. So he takes the clothes and puts them on as Elizabeth instructed, starting with the bloomers.

Right after starting to put the clothes on, the denim like fabric began to send an electric sensation shooting up and down his legs. This seemed to continue on until they settled up against his smooth formless crotch, where the cloth wedged up against the pussy lips almost feeling right. The underwear seemed to fit perfectly around his waist making it feel a tad bit more comfortable. But it still felt weird having such garments cause a thrill to sore throughout his lower body.

He wanted to leave now, to run out and get away from this girl. But he looks at the pink bra Elizabeth tossed his way and he is genuinely curious to try it out. So he grabs it and holds it out examining how it fits. He threads his arms through the holes in the straps and ducks his head to squeeze it over around his chest. It is a snug fit and something about that pleased Jamie.

"Not bad," Elizabeth said after closing the locker door. "But it could use something else... hold on." She had taken something else out of the locker it seemed.

Jamie feared the worst as he saw her turn away from him looking in a different bag. He continued pulling on the rest of the uniform, starting with the tank top allowing it to flow down over his slim form before pulling up the skirt completing the outfit. Pom poms are really needed to finish it though, but he has no desire to get them.

There was a sudden urge to strike a pose and do a cheer like he had seen cheerleaders do a thousand times. It was a fleeting one and he pushed the impulse down right away. The next thing was seeing himself in the mirror, and realisation struck him at that point.

With the material clinging to his petite form, he could see every single contour of his body. If he ran into anyone that was even mildly attracted to girls, they would be drooling all over him like a piece of tender meat. Although at this point, he knew that without the proper modifications everyone would instantly know that he was male no matter how he looked.

Elizabeth would soon fix that, as she appeared behind him holding a long blonde wig which when properly placed on someone's head would reach down to the middle of their back. In her other hand lay small box, its lid covering the contents within, but judging by her grin he knew it was something that would only be adding to the layers of this scenario.

"Ooooh you really do pass for a woman," she paused before continuing. "It just needs some touching up. Sit down and we will get you all set up." Elizabeth directed whilst forcing Jamie to sit down on the bench facing away from the mirror so that he had no idea what she was doing to him. About twenty or thirty minutes later she finally finishes and stands back whilst grinning down at him.

"Now you really do look like a hottie Jamie, or should I call you Jessica now?"