# Humilated Pleasures-Chapter 3

Author: Falcon3268
Tags: Crossdressing, Other, Period, Plot Development

#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?"

Source: https://sofurry.com/s/Rm0LB2Zm
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