Will thought he had it all figured out. Senior spring of high school at an elite New England prep school, he had already been admitted to a good college. Why should he bother attending class anymore? Still, he couldn't just skip showing up to school altogether. So he did anything he could to get around the rules without really breaking them. Teachers couldn't object when he complained of some mysterious pain that required a trip to the school nurse, even if everyone knew Will's ailments were just an excuse to get out of class.

Friday afternoon, Will tried his usual excuse, complaining of stomach cramps. His English teacher rolled her eyes and granted Will permission to go to the nurse's office.

Nurse Rachel was also on to Will, though there was little she could do to disprove his symptoms. Like everyone else, she felt that it was easiest to go along with things. Usually, she gave him an Advil and told him to lie down until he felt better. Plus, she liked his cocky attitude, the way he flirted with her when he came in. She would sometimes give him a knowing wink to demonstrate that she knew he was faking. At age 40, Rachel retained her figure and youthful looks, but attention from such a young, fit guy like Will was becoming rarer. She might even miss Will when he graduated.

Just as the prep school required students to wear formal clothing (a jacket and tie for boys, a pleated skirt for girls), so did they maintain a more formal style of dress for the school nurse. Rachel wore a starched white nurse's uniform and white stockings, though regulations spared her the nurse's cap. She didn't mind the uniform. Some mornings, looking at herself in the mirror before heading out the door, she even thought that it hugged her body nicely.

The nurse's office was otherwise empty when Will entered. He put his hands on his stomach in an exaggerated display of pain.

"Nurse, it looks like my stomach is acting up again. Any chance I can lie down until the pain passes?"

Without even waiting for a response, he made his way towards one of the cots reserved for recovering patients. Rachel wasn't sure what it was--maybe Will was looking particularly handsome, maybe she wanted to match Will's caviler attitude herself, but she decided to do things differently this time.

"I'm sorry to hear that you're not feeling well. Let me take a quick look before you lie down. Could you hop up on the exam table?"

The look on Will's face changed immediately. He knew she was calling him out. But he couldn't just admit it was all a ruse. He tried to remain confident, but they could both hear the nervousness in his voice when he answered.

"Sure nurse, I'll go right in."

Will followed Rachel through a door to the adjacent examination room, secluded from the main nurse's office for privacy. Rachel closed the door after Will. A single padded exam table stood in the center of the room. On the wall was a sink and the usual assortment of medical tools.

"Please lie back on the exam table, I'd like to palpate your stomach to see where the pain is located." Rachel walked over to a sink and began to wash her hands.

Will did as he was told. He could feel his palms getting sweaty. Rachel had never really touched him before besides taking his blood pressure once or twice. What was going on?

Rachel approached Will and lifted up his shirt without asking.

"Now just take deep breaths and tell me if you feel any tenderness."

She began pressing down on his stomach, kneading in small circles. She secretly enjoyed having an excuse to run her fingers over his tight abdomen, working her way down closer to his cock, wondering how he felt now that his little game had gone off the rails.

About half way down his stomach, Will gave his best performance of a pained cry. A part of him didn't want her to stop. The warmth of her touch working down towards his belt felt good, but he was afraid that if she went much further, his dick, already getting partially hard, would become noticeable, even under his pants.

"Right there nurse, I think I just need some pepto or something."

"Now Will, please let me do my job."

She didn't want to give this up just yet, in fact, she was only getting started.

"I'm very concerned, and I'm going to need you to strip down and get back on the table so that I can continue my examination. I may need to do a rectal exam. I know this might be embarrassing, but I can assure you that it's my job, and it will help me get you feeling better."

Real fear now flashed in Will's eyes. He tried to protest for a moment, but Rachel responded to him sternly.

"Will, please don't try to pretend there’s nothing wrong, this could be something serious. I need you to strip and get back on the table."

Will wondered what she was up to. Clearly, from her tone, she was not going to back down, but what was her plan? He thought about how long her hands had lingered while pressing his stomach. He got up and began to remove his clothes, facing away from Rachel, folding them in a neat pile, not wanting to turn around and show his semi-hard cock to the nurse. Could that be what she wanted though?

Rachel herself wasn't sure. All she knew is that she wanted to see Will naked, and she was enjoying embarrassing him. A light warmth spread between her legs. She was getting a little wet watching him get undressed, seeing his tight ass wiggle as he kicked off his pants and folded them. She walked over to the sink and began to wash her hands as Will returned to the exam table. She then grabbed two latex gloves from a dispenser on the wall and returned in front of Will, where she slowly slipped the gloves over her hands, letting him watch and wonder what she had in mind.

“I’m going to need to palpate further down, so please lie back again for me.”

She glanced down and saw his cock, something she had often wondered about, even larger and thicker than she had imagined, beginning to grow.

Will lay back and closed his eyes. He noticed Rachel’s quick glance down at his cock. Was he imagining things, or was she going to jerk him off? In his nervousness, the stomach problem he had made up earlier was beginning to become real. He felt her gloved hands touch his lower abdomen, closer to where his waistband would have been.

“Tell me again where it hurts.”

Her voice was breathier this time. Will stay quiet. He wondered how far down she would go. The rectal exam must have been a threat. But she was wearing gloves. Her hands continued to prod further down, now directly above his neatly trimmed pubic hair, now pressing on his inner thigh. His cock was now nearly fully erect, and there was no way she didn’t see it.

“No discomfort?” Rachel smirked and looked down at Will’s cock. It was bigger than she had imagined.

“Don’t worry honey, it’s normal to be nervous when you’re being examined.”

Will’s face flushed with shame. Sure, he had fantasized about hooking up with the school nurse, but this was much more clinical, more vulnerable. He could hardly answer her question.

“Yeah uh, it’s a little sore I guess.”

“I know this might be embarrassing, but I need to do that rectal examination just to be sure that there isn’t something more serious for us to address. Could you please put your feet up in the stirrups for me?”

Seriously? Will looked down at Rachel, now standing between his legs as she unfolded the stirrups from the sides of the exam table. His cock stood straight up. He wanted out of here.

“Really nurse, I don’t think I need that. Can’t I just have some pepto?”

“And do you also want me to let the principal know that you’re coming to the nurse’s office but refusing treatment? Don’t you think that sounds a little suspicious?”

Rachel spoke with an added force. Will had gotten himself into this situation. Now he had no way out: submit to whatever it was Nurse Rachel wanted or face some serious disciplinary consequences. He lay back down and let Rachel guide his feet into the stirrups, then closed his eyes and tried not to listen as he heard the distinctive pop of lubricant being squirted out.

“That’s a good boy. Now you might feel a little pressure as I press my finger here. Have you ever had a rectal exam before? Or played with yourself here?”

Will squirmed a bit as he felt the cool lubricant touch him. Nurse Rachel’s finger paused, then began to swirl the lubricant around almost sensually.

“Wh-no, no I haven’t. I’m not gay.”

Rachel smiled and began to work her finger into Will’s ass. He certainly wasn’t trying to keep her out.

“You don’t have to be gay to enjoy it. In a non-medical context of course. In fact, it seems like you’re not experiencing any discomfort. I’m going to insert my finger now. Please bear down for me.”

Rachel slowly pressed at Will’s rosebud and was surprised by how eagerly his asshole opened for her finger. Will let out an involuntary moan and gripped the sides of the table tightly. He tried to focus on anything but what was happening, anything but his cock growing fully, almost painfully, erect. Rachel took her time pressing into Will until her finger was fully extended. She then bended it slightly, pressing down on his prostate.

“How does that feel sweetie?,” she cooed, knowing fully well from his throbbing cock exactly how it felt.

“It-um-ouch,” Will faked, his breath somewhat short.

“I’m pressing down now on your prostate. Usually boys your age don’t need them examined, but your symptoms made it sound like yours might be a bit swollen. I know it might hurt a bit when I press down on it, but I need to massage it in order to make sure everything is working. Is that alright?”

“M-massage?,” Will asked. Out of fear, he involuntarily squeezed down on Rachel’s finger. A warmth had already begun to spread from deep inside of him up through his cock. Will looked down and saw Rachel smiling sweetly up at him. The room was silent except for the faint crinkling of her finger pushing slightly in and out.

“That’s it, you’re doing a good job for me,” Rachel said, her voice a little lower now.

She knew she was taking a huge risk by doing this, but there was no chance that Will would tell anyone. His humiliation would only be compounded if he went to someone to question whether he really needed the school nurse to bury her finger up his ass. Plus, if the little droplet of pre-cum pooling on the tip of Will’s penis was any indication, he’d soon have much more to be embarrassed about. She pressed even harder, seeing if she could force the cum up out of him. She looked up at Will as she felt his ass begin to tighten rhythmically. He was getting closer, and they both knew it.

“Is everything alright honey? I’m not hurting you, am I?”

“Yes, ouch, could you stop?,” Will lied, trying to get Rachel to stop her probing before it was too late. But Will was a terrible actor, and his slowly bucking hips told a different story. He could feel a wetness running down his cock as semen began to dribble out.

“We’re almost there Will, I think you’ll be feeling much better soon.” Rachel continued to tap on his prostate and watched as Will dug his hands into the side of the exam table before his cock erupted, shooting cum onto his bare chest. She could see that Will had his eyes closed and mouth half-open in an expression of pure bliss, though he let out no sound besides a frantic breathing. She continued to massage his now hard prostate until the last jet of semen trickled out of his cock, hardly believing what she herself had just done.

“Oh my Will,” she said, her finger still buried in his backside but no longer pressing.

“It looks like you had a little accident. Please don’t be embarrassed, it’s an involuntary response. I’ll get you some tissues so that you can clean yourself up.”

Rachel slowly removed her finger from Will’s behind, stripped her gloves, and placed a box of tissues on the exam table. She took a moment to admire her patient. He still sat with his eyes closed and cum all over his chest. She still wasn’t sure what had made her do it, but she could feel her hard nipples straining against the material of her bra and a slickness between her legs.

“I’ll give you a moment of privacy and be back in a few minutes.”

Will opened his eyes once he heard the door click. He’d never realized that he could cum without even touching his cock. He’d never cum that hard at all. He grabbed a few tissues and began to wipe the now cooling cum off of his chest, amazed at how far some of his semen had shot. After doing his best to clean up, he stood up and begin to dress again. He could still feel the slick lube between his ass cheeks. A part of him was angry at nurse Rachel, but another part of him was intrigued. What the hell was he supposed to say to her when she came back in?

Meanwhile, Rachel spread her legs under her desk and let her hand run up her thigh to find her crotch. Even through the white stockings, she could feel the dampness of her pussy. She pressed down once hard on her clit, sighing lightly, then gathered herself together and walked back over to knock on the door of the exam room. Without waiting for an answer, she entered to find Will standing up, dressed, a bewildered look on his face.

“I sense that you’re feeling a bit better? Do you think you’re ready to head back to class?”

“Yes nurse,” Will replied, not making eye contact with Rachel, “I’m feeling much better.”

“I’m glad to hear that Will, though I think it would be best if you returned sometime later this week for a follow-up examination to make sure this problem doesn’t persist.”

Will looked up at the nurse. He could see the flush in her cheeks.

“Yes nurse, I think you’re right. I have a free period next Monday at 2.”

“Good, I look forward to seeing you then.”

Rachel opened the exam door and stepped aside, then watched as Will walked out to return to class.