Token of AppreciationbyLOAnnie2©
"Finally, happy eighteenth birthday to Jason Jones and Valerie Arians. Have a wonderful day Albright Academy." Ashleigh Miller lifted her hand from the mic cue and sighed. She took a step back and walked over to the table holding twin bingo machines that sat in the corner of the school office. Kneeling down, she opened the cabinet tucked underneath and pulled out two little wooden balls with the names Valerie Arians and Jason Jones etched into them. She closed the cabinet and stood up.
As she put Valerie's ball in the rightmost bingo machine, she murmured "Sorry Val." After placing Jason's in the leftmost, she added, "likewise Jason." Ashleigh knew though that for the most part Jason would probably enjoy being part of the daily lottery, but the girls never did.
Ashleigh glanced around and saw one of the secretaries flashing a big smile. "Must be her turn today, no woman sponsor in," she said quietly to herself. She started hand-cranking the tumbler and giving it a moment before hitting the switch that would allow the tumbler to pick a ball. One more turn and a ball was in the little catch. She picked it up and started to chuckle. "What a birthday present," and she took the Jason Jones ball over to the secretary so she could arrange the summons to the office.
The secretary looked at the ball and grinned even more widely and quickly picked up her phone to call Jason out of class. Ashleigh turned back to the girl's machine and had a sudden thought–it was entirely possible that today's sponsor was a lesbian. She heard there was one, but in the five months since she turned eighteen she hadn't been picked on any of those days. Instead five different older men, some of whom she knew had fucked her in the headmaster's office.
Of course she wasn't being held there–she could refuse and leave Albright Academy. Leaving however would have consequences–being cut off from her inheritance, and the private school wouldn't turn over transcripts so college was out of the question. No, Albright had the idea just right–the exclusive school could get away with it because the place was that desirable to attend.
If Ashleigh had been the worst student at the school, she could still be all-but-guaranteed a spot at any university of her choice. Careers of her choice, assuming she didn't want to be a trophy wife. Attending Albright led either to an easy life, or a life at the top, whatever the student wanted.
There was no cost to attend, the entire system was run via endowments from wealthy alumni, many of whom were the parents of the students themselves. The only catch of course was that when the students turned eighteen, they would potentially be subject to pleasuring some of those wealthy alumni in repayment for their generosity. It was a weird system that Ashleigh could only imagine the type of person who would come up with, but it had worked for the private school for centuries.
Ashleigh grabbed the handle and started spinning the bingo tumbler. As student body president it was one of her duties, to operate and determine every day who it would be that thanked the alumni for their donations. As much as she hated the system, the worst part was the whims of the headmaster, who insisted the girls perform in his office. Headmaster Carlisle was very much a voyeur, and always took great pleasure from watching the girls be taken.
Ashleigh closed her eyes as her stomach cramped up a little. She'd spent the entire weekend sick and hadn't eaten solid food since Thursday night. She didn't want to be in school today, but her father had made her come to school anyway. She took a deep breath and continued to spin the tumbler finally flicking the little switch that would allow a ball to fall out once more. For some reason it took several more spins before a ball finally popped out.
She picked it up and cringed, suddenly hoping that it wasn't one of the lesbian donors as she read her own name on the little wooden ball. "Thanks for making me come to school today dad," she mumbled as she set the ball back down and made her way over to the headmaster's office.
She didn't knock, instead just entering and quickly shutting the door behind her–Ashleigh knew the drill and assumed just getting it over with. Turning back around once the door was shut. She saw exactly what she had expected–Headmaster Carlisle behind his desk and a finely dressed older man whom she had never seen before.
"Ah, splendid. Mister Danforth, may I introduce you to Ashleigh Miller, Albright's Student Body President," the headmaster said with a little too much enthusiasm. "Ashleigh, be a dear and give us a spin."
It wasn't unexpected, and Ashleigh spun as ordered. She was wearing the standard uniform for Albright, light grey khaki pants, a white button-up blouse that wasn't tucked in, and a navy blue sweater-vest. Ashleigh's trim, athletic body looked rather decent in it even though someone with larger breasts would fill it out better. Throughout her spin, she started to wonder who Mister Danforth was, she'd heard some of the other girls mention the name before but wasn't sure why.
"Thank you Ashleigh, you may proceed," she was informed by the headmaster.
It was almost a trance as she moved to the right side of the headmaster's desk. However, she was surprised when Headmaster Carlisle stopped her. "Not today Ashleigh, today I want you in front of the desk."
She paused, looking a bit concerned, but moved around in front of the headmaster. She reached down and unbuttoned the khakis before reaching to the side to pull them and her panties down to her mid thigh, exposing her tight teenage ass to Mister Danforth, but not to the headmaster. She bent over the desk, resting her arms on the cold oak and looking right at the headmaster.
"Mister Danforth, my name is Ashleigh Miller, and on behalf of Albright Academy I would like to thank you for your extremely generous donation to our school. Please accept this token as a sign of our thanks." She recited it perfectly, and just waited.
Mister Danforth spoke with a slightly muffled accent as he moved behind Ashleigh. "Mmm, thank you Ashleigh, it looks like it will be a wonderfully enjoyable gift indeed."
All she could do was wait–she heard the sound of a belt being unbuckled and soon falling to the floor, presumably with the older man's pants. The squeeze of a plastic bottle broke the silence for a moment, and after a second squeeze she finally felt what she expected–two fingers covered in cold lube exploring the folds of her pussy.
Ashleigh had to admit the was slightly wet even though she couldn't help it–her body knew what was coming, how she was presenting herself to be fucked, of course it was going to be turned on, but more lube was probably a good idea anyway. The fingers however did not remain long, and Ashleigh had to go back to anticipating.
One downside to how she was supposed to present herself and wait was that she didn't know what to expect for the size of cock that was going to enter her. She only had to wait a moment to get her answer though as she felt the cock brush against her pussy. As Mister Danforth positioned it he started to plunge inside her, and Ashleigh couldn't help but let out a moan.
It wasn't the largest, but it was still decently sized. Outside of being fucked in the headmaster's office, she'd only been with four boys her own age. As she felt the girth stretch her she started to think, figuring this was maybe the third thickest cock she'd ever had. Thanks to the lube applied to her pussy and some he'd applied to his cock, it didn't take long for Mister Danforth to bottom out. Also not the longest, but pretty good length, maybe eight inches she'd guess.
There was another thing Ashleigh hated about being made to do this. The cock that was now pulling out to get ready to actually fuck her with some rhythm was pretty decent, and if she wanted to be fucked she'd probably quite enjoy this. But given that this was more of a chore, she'd have a much harder time just relaxing and having fun.
She was a bit surprised as she felt the hand grab her dark brown hair that she was wearing in a ponytail today. Mister Danforth had kept a slow pace, probably to prolong his experience, but Ashleigh had to admit it was working for her. Oh, she had cum the last three times she'd been in this office, but more from that she didn't resist than she was actually getting into things. At least there would be some payoff for this degrading little scene.
Back and forth, in and out Mister Danforth kept thrusting with his slow pace as Ashleigh started to heat up. It felt a little weird to be facing Headmaster Carlisle, and he had an unusually big grin on his face. She was a little surprised when she felt the man behind her pull out.
"This is a very exquisite pussy James," Danforth started, "however, you know my proclivities. I would like to have her ass."
Ashleigh's eyes bulged widely as she looked up at the headmaster with horror written all over her face–that's where she'd heard the name before. There'd been talk about a guy who had a fetish for anal sex, and he'd taken several girl's anal virginity. She wasn't really watching the wide grin on the headmaster's face as he reached into his desk and pulled out a little bottle.
"Make yourself at home. Ashleigh, would you be a dear and hand this to Mister Danforth," he said. "You should be fine Mister Danforth, she's been sick all weekend and hasn't eaten solid food since Thursday."
She didn't register that she was handing the man a bottle of lube–only the thought about what was going to happen raced through her mind. The senior didn't register the cap being opened, or the sound of lube being squeezed out–in fact, she didn't register anything until she felt a hand spreading her ass and then felt a finger press against the rosebud that was her asshole. Ashleigh couldn't help but jump though as she felt the cold lube make contact with her body.
Ashleigh was unable to place the feeling, or even interpret it as she felt the finger run circles around her last virgin hole. She knew some girls who had lost their virginity in this office, she was glad she hadn't, but still couldn't have imagined that she'd lose her final virginity here. As she tried to contemplate her situation some more she missed that the finger had stopped circling until she felt a sudden surge of pressure.
The girl let out a cry as the finger pushed into her ass and heard a laugh coming from in front of her. Looking up again she saw that Headmaster Carlisle was overjoyed with delight. "Hmm, I think I'll have to put Ashleigh on my graduation list, if she continues to look as amazing as she does right now."
A sigh and a cringe escaped from the president. The headmaster didn't get to take advantage of the girls in quite the same way that the sponsors did, but he did get to choose five of the girls graduation week to finally have some real fun with. It wasn't a list she wanted to find herself on, and she hoped that several of the other girls would entice him more.
She continued breathing deeply as Mr. Danforth kept finger-fucking her ass. Even though it was hurting less, she felt weird having it happen to her. A little sense of relief came over her as it finally withdrew, but she suspected what was coming.
The hand that was holding her ass spread finally pulled back. Mr. Danforth boomed to her, "Madam President, please reach back and spread your ass for me."
She groaned at the order, but knew better than to disobey–that would open a whole different can of worms that she didn't want to deal with. Her face turning red and watching the grin on the headmaster's face growing even larger, she reached her hands back and pulled her cheeks apart, exposing herself fully to the man about to take her ass.
The hand that had previously been holding her ass spread reached up and grabbed her left hip. She felt him step closer and once again felt pressure at her untested hole. She tried to brace herself for what was coming while still relaxing–she wanted it to hurt as little as possible. Finally she felt him push forward and the pressure increased. Ashleigh cried out as the cockhead pushed inside her with little effort thanks to the lube.
"You can let go now Ashleigh," the man invading her ass told her. The girl pulled her hands forward, wanting to bury her hands in them while Carlisle laughed at her.
"I always love that face," Carlisle told her. She started to look down, but felt a hand grabbing her ponytail and pulling it back. Danforth had grabbed hold of her, and she couldn't look away from Carlisle at all now. With one hand on her hair and the other still on her hip, the older man started to pull her ass onto his cock. She couldn't help but whimper and let out little cries as the large cock opened more of her virgin ass.
Once again Ashleigh was pulled from her spacing out by what was happening around her–in this case a flash of a camera phone as the headmaster took a picture of her face. A single laugh escaped from him and he turned the phone around to show her the picture. If Ashleigh didn't know it was the picture he just took of her face she'd wonder who the girl was and what was happening; the look of pain, confusion, and betrayal on her face didn't seem like it could be her.
It took several more moments but she felt course pubic hair against her ass. She finally realized that he was buried completely in her ass. Ashleigh took several deep breaths, trying to get used to the feeling of the cock filling her ass.
"How's it feel Ashleigh," Carlisle suddenly asked.
"Huh?" she responded back while being forced to look him in the face.
"How's it feel with the cock all the way in your ass Ashleigh."
When she didn't respond immediately, Danforth pushed a little more, getting just the tiniest bit more inside her, causing Ashleigh to cry out, "Full, I feel full."
Apparently that was all Danforth needed to hear as he started to pull back until only his head was left in before shoving in again. Ashleigh let out another cry as she was once again completely filled. A cringe crossed the teen's face when he pulled a little harder on the ponytail and tightened his grip on her hip–she had a feeling of what was coming as he pulled out and started slamming back into her faster. The older man was wasting no time as he started to fuck her ass.
Ashleigh didn't know how to respond to the pain as the cock sawed in and out of her tightest hole, but she didn't know what to do about the slight feeling of pleasure she was getting. She could start to see how some girls might like this, it was definitely naughty in her mind, but of course with some older guy just doing it for his pleasure she knew it wouldn't come for her.
Her breathing became more labored as she continued to be buttfucked by the donor. Even though she wasn't really looking anywhere as it was happening, the occasional times she'd focus on her headmaster's face he was nothing but smiles. There was a sudden flash in front of her–did he just take a picture she wondered.
She saw no sign of a camera as she tried to focus as best she could–instead she saw that the headmaster lean forward, his hands moving past her head. A tugging at her sweater-vest told her what he was doing as he pulled it up her torso, along with the white blouse. "Grab my shoulders Ashleigh," the headmaster ordered.
The teen could only imagine the joy the headmaster was getting from her embarrassment as she extended her arms forward to allow him to strip her of the sweater vest. Danforth released his hand from her ponytail long enough for the headmaster to pull it past her head but promptly grabbed it tightly again while he kept drilling into her ass. The headmaster left the sweater-vest on her arms as he reached underneath to unbutton her blouse to remove it easier.
Another moment later and she felt the blouse being pulled up again. When Danforth released her ponytail this time he felt her hand reach to her bra, where he undid the clasp with a quick snap of the finger. If it were a different situation, Ashleigh might be impressed with his skill at undoing a bra. The headmaster's hands finished tugging the blouse over her head before reaching to pull the bra forward. Of course the hand once again grabbed her ponytail. Pulling everything to where her hands were holding his shoulders, the headmaster once again ordered her around. "Elbows on the table Ashleigh."
Letting go of his shoulders and putting her elbows on the table made it simple for the headmaster to relieve her of the pesky clothing that kept her top covered. Her small breasts hanging free he threw her clothes to the floor on the side of his desk and reached out feeling the teen's small but firm tits. The headmaster chuckled at her and exclaimed, "Oh look Ashleigh, they're even hard."
From behind her she started hearing the man's grunting get louder–all she could do was hope he was almost done. Danforth pulled hard on her ponytail, yanking her up from the desk as he pushed hard into her ass one last time. A very loud groan came from the man buried in her ass and she felt a warmth unlike any she'd experienced. She couldn't concentrate very well on the feeling though, the pain from having her ponytail still held tightly was a bit too much for her.
After what seemed like forever he finally let go of her ponytail. If her hands hadn't been in front of her she probably would have slammed back down into the desk. Once Ashleigh was bent over again she felt him pull his softening cock out of her ass, leaving her with a strange sensation of emptiness.
The teen knew the ritual–even as the headmaster resumed playing with her breasts she was supposed to stay bent over. Finally after an eternity that actually amounted to about four minutes she heard what she presumed was a sign for the last little bit of pageantry.
"Well, well, thank you for allowing me to use your student body, Madam President," Danforth said with a little bit of viciousness in his voice.
The headmaster's hands retreated from her breasts and she pulled herself up, turning around to face Danforth, allowing him to see her naked save for the pants and panties which had fallen to her ankles. As best she could she did a curtsey toward Danforth. "Thank you for your very generous donation to Albright Academy. I hope you will take advantage of future tokens of appreciation we offer and continue your donations to our wonderful school."
Danforth just gave a nod, though not to her but to the headmaster. "Until next time James." With that the man rather unceremoniously left the office.
"As much as I enjoy staring at your just fucked ass Ashleigh, I think you have one more responsibility left," the headmaster called to her once his door had shut again.
A sigh once more escaped Ashleigh's lips as she dropped to the floor and crawled over to his desk. The headmaster, obvious hard-on and all, turned toward her and smiled. Reaching up Ashleigh undid the headmaster's pants and reached into his boxers, pulling out his cock.
Ashleigh closed her eyes for a second before looking the headmaster in the face. "Please sir, allow me to thank you for this opportunity to represent the school to one of our benefactors," she told him before opening her mouth and taking his cock into her mouth.
Letting out a moan of pleasure, James Carlisle grabbed her ponytail with his right hand and said aloud, "Sometimes you just gotta love this job."