Dollars and Desire
Copyright© 2025 by brabo1978
Chapters 6: The Principal
Erotica Sex Story: Chapters 6: The Principal - After a disastrous date that is ruining her reputation, Ashley decides to sell her face as a canvas for boys to come on.
Caution: This Erotica Sex Story contains strong sexual content, including mt/ft Ma/ft Teenagers Coercion Consensual Fiction Brother Sister Facial Masturbation Petting
As she put her English books in her locker, Ashley heard the loudspeaker crackle to life. “Ashley Myers, please report to the principal’s office immediately.”
Ashley froze in place, her books still clutched in her hands. A summon was rarely good news, even more so when you knew you were doing something that wasn’t just against school policy, it was most likely considered illegal. Ashley may not have thought of her side business as prostitution, but she knew perfectly well that others, “authorities”, probably would. She really hoped this was about something else, anything else.
With a heavy heart Ashley made her way towards the principal’s office. She tried to keep her steps light, her voice even and her facial expression neutral as she stepped inside and greeted the secretary. On the off chance that Principal Smith didn’t know about her activities, she didn’t want to give anything away. She wasn’t sure she was pulling it off though.
“Good morning, Mrs. Jenkins. I was told to come here?”
Mrs. Jenkins looked up from her desk and nodded. “Ashley? Yes, the principal wants to see you right away.”
“Thank you,” Ashley said, forcing a smile before walking towards the door leading to Principal Smith’s office. She took a deep breath and knocked on the open door to announce her arrival.
“Come in, Ashley. Please close the door behind you,” Principal Smith called out from behind his desk.
Waiting for him to finish whatever he was doing on his computer, Ashley did as she was told and turned to face him. Principal Smith was a middle-aged man with a stern face and his hair was graying at the temples. It was his piercing eyes that made him intimidating. That, and the fact that he held her future in his hands. Ashley swallowed, her already limited confidence breaking down further as she stood before him.
Principal Smith finally looked up from his computer, his eyes meeting hers. “Have a seat, Ashley.”
He gestured to the chair in front of his desk. Ashley obediently took a seat, her hands folded in her lap as she waited for him to speak. Steepling his fingers as he looked at Ashley, Principal Smith finally began talking.
“I just reviewed your record, Ashley. So far your conduct at school seems to have been exemplar. I see no disciplinary notes, no detentions and you get mostly consistent decent grades. So I was quiet surprised when certain ... rumors started circulating about you.”
Ashley could feel a blush starting to creep up her face. She scolded her body for betraying her and make her look guilty. But on some level she already knew that somehow she wouldn’t be able to deny what she had done. There was something he wasn’t telling her yet.
“Rumors, sir?” she managed to get out, after what felt like an eternity to her.
“Well, it’s not like we’re in the habit of believing everything that circulates around the school,” Principal Smith replied, his expression still inscrutable. “But considering the nature of these rumors, I thought it wise to check the school’s security camera’s. You know, just to make sure nothing untoward is happening on school grounds.”
Shit! He didn’t need to continue. Ashley knew what he had seen. Why hadn’t she thought of the camera’s? Never before had she felt so ashamed. Not just because Principal Smith knew what she had been up to, but he had even seen her doing it. He had seen her breasts. He had seen her in some very intimate situation, maybe even more than once.
“Now, I’m sure you know what you’re doing is not just against school policy. Prostitution is illegal, Ashley. I’m supposed to notify your parents and to report this to the police. You’ll most likely get expelled as well.”
Ashley felt tears welling up in her eyes. Involuntarily, she hid her face behind her hands. It was as much as admitting guilt, but it didn’t matter anymore. He had all the proof he needed. Her life was over. Whatever hope she still had for the future was now shattered.
“It would be a real shame to see such a promising student’s future ruined like that,” Principal Smith continued, “I really don’t want to see it happen.”
Something in his voice allowed Ashley the smallest glimmer of hope. Something that she clung onto for dear life. If there was any chance, any way she could avoid this path, she’d take it. She lowered her hands and looked up at Principal Smith, her eyes searching his face for any sign of his intentions, for any sign that her hope was justified.
“Is there ... any way to avoid this?” Ashley asked, her voice barely above a whisper, her hands still trembling in her lap.
Principal Smith studied her for a moment before he spoke, his expression softening slightly. “I’d love to help you, Ashley. But I can’t. If anyone would find out I didn’t report this, well, then it would be my job that’s on the line. You don’t expect me to jeopardize my career, do you?”
Ashley felt her heart sinking once again. Maybe even worse this time, as she had allowed a kindle of hope to flare within her, only to have it snuffed out again. Of course she couldn’t ask him that. This was her problem. Her mistake. Her fault. She couldn’t blame him. She couldn’t ask anyone to ruin their life because of something she had done. She understood. Dejected, Ashley lowered her eyes, staring down at the floor.
“At least...”
There was that hope again. Did he know how he was torturing her like this?
“ ... not without a ... token of your appreciation for what I’d do for you.”
Slowly, Ashley looked up at the principal again. That sounded like her hope wasn’t completely baseless. Was he really offering her a way out? Ashley’s mind was racing, trying to process his words. The stress and fear were making it difficult for her to think clearly.
“Wait, what?” Ashley blinked, trying to remember what he had said exactly.
“Now, come on, Ashley. You’re smart enough. If you want me to take a risk like that, you have to give me a reason to do so. Make sure that ... our interests are aligned,” Principal Smith replied, leaning forward on his desk.
When realization hit her, Ashley’s eyes widened in shock. He wouldn’t ... He couldn’t...
“You ... you want me to...?” She couldn’t even finish the sentence. Her mind was racing with disbelief and horror. A totally different kind of horror, as she noticed he was now openly gazing at her body, at her legs, at her cleavage. He made no attempt to hide his interest, sinking any hope she had that she had misinterpreted his message.
“But that’s blackmail,” Ashley protested weakly.
“Well, at least it won’t be prostitution, as I’m not giving you money,” he smirked.
Ashley was speechless. She wanted to protest, she wanted to scream, she wanted to run out of his office. But she didn’t do any of those things. Instead, she just stared at him, utterly shocked by his proposition. Defeated, she looked down again, unable to tolerate his lecherous gaze any longer.
“What do you want me to do?” Ashley asked, barely audible.
Leaning back again in his chair, satisfied and victoriously, Principal Smith’s smile widened. “I think I’d like to see you in your work outfit, if you know what I mean.”
“You mean...?” Ashley asked, vaguely pointing at her top.
A nodd and an insinuating hum was all the confirmation he gave her. Under his expectant stare, she hesitatingly took the hem of her top and lifted it up, revealing her flat stomach, her plain white bra, before pulling it all the way up and off. She couldn’t bare look at him, but she could feel him looking at her body intently. She wished the floor would open up and swallow her whole.
But of course it didn’t and instead she reached behind her back to execute his unspoken command. She unhooked her bra and pulled the straps down her shoulders, letting the garment fall to her lap. Even after making the choice that had ultimately led her here, in this position, she had never thought she would be showing her bare boobs to the principal. But here she was. Her cheeks flaming with embarrassment and humiliation, her heart pounding behind her exposed, perky breasts. To her horror, she realized that her nipples were hardening in response to the cool air in the room.
She fought the instinct to fold her arms across her chest and hide her body. She knew he wouldn’t let it stand anyway and didn’t want to show any more vulnerability than necessary. Instead, she just waited for his next move. The hunger in his eyes was clear as they roamed over her body. Then he suddenly looked up and into her eyes.
“Well?” Principal Smith prompted impatiently.
Ashley was briefly puzzled, as she had assumed that she had done what he had asked from her.
“If I’m going to sample what you’re offering, you’ll need to be fully naked, don’t you think?”
At first, Ashley didn’t understand what he meant. This was what she had done for the boys: get topless, jerk them off and let them cum on her face. Then she realized the implication of his words.
“Wait, no, I haven’t ... they didn’t have sex with me. It was only...”
Well, there had been Michael of course, but that was a one time thing. And there was no way he could know about that. But clearly it didn’t matter, as Principal Smith interrupted her.
“Yeah, sure. And I’m supposed to believe all those boys were willing to pay you not to have sex with them?” he scoffed, clearly not convinced.
“But, really, that’s not...”
“Cut it out, Ashley. Get on with it. Unless you changed your mind and prefer that I call your parents and the police.”
The threat was clear in both his voice and his gaze, daring her to challenge him.
When her shaking hands unbuttoned her pants, it felt like it was unreal, like this wasn’t happening, not to her. She barely found the strength to stand up to push her jeans and panties down her legs. As she struggled to remove her jeans, she could feel his eyes on her swaying boobs. Finally free, she stood up straight. Never before had she been so aware of being naked. She had been topless in front of a boy before, plenty of times by now. She had even been naked with Michael. But this felt different. It felt humiliating, dirty.