Chapter 9
by
MistressOfTheNightWinds
Does he make it to the end of the day?
Nope
I made it through the next class then had a break, but one of my students lingered behind to ask a question. “Mr. Doe, I...um, I have a….question.” She starred down at the floor while speaking, obviously embarrassed by whatever problem she was having. Caitlin was a short redhead with her flaming red hair in pigtails. I could never tell how busty she was, she always wore a blouse that was a size too big. That is, until I did her breast inspection earlier. Her boobs were much larger than I thought they’d be. When she walked up to me at the beginning of class and opened her shirt, I was downright floored at their size. She did everything she could to hide them, almost like she was embarrassed by have such large breasts.

“Caitlin, I’m your teacher, answering questions is kinda the whole gig. So what’s up? Are you struggling with today’s lesson? You seemed at little off today.”
“No, that’s not it. Its...something else. I feel really weird asking anyone about it. Its very...personal.”
My curiosity was peaked now, and the way she fidgeted and pressed her legs together gave me a bit of an idea of what it could be. “You can ask me anything, I’m a scientist at heart.”
“Well, its just that...um...All day, I’ve been having a weird feeling.” She took a deep breath and continued “You know, a feeling...down there.” She pointed to her crotch. I was barely able to contain a devious grin. “Well, ok. I can see why you would be embarrassed by that. But don’t be, whatever is going on is probably perfectly natural and normal. So, can you elaborate? What exactly are you feeling?”
“Its like a tingling feeling.”
“Oh?” I knew exactly what she was experiencing, but I really wanted to have some fun. “Hmm, that could be a couple different things. I think it would be a good idea to do a vaginal inspection.” Up to that point, she had continued to stare at the floor. But then her head shot up with a look of shock at hearing the word ‘vaginal’. “Is that really necessary!?”
“I’m afraid so.”
“Alright, what exactly does that entail?”
“Well, for this kind of inspection, you’ll need to be completely nude, so go ahead and take off all your clothes.” I answered and couldn’t wait to get started. I was already pitching a tent in my pants just imagining how tight this girl would be. Given her demeanor, and the fact she was shocked by the word vagina, it was clear she was a virgin. Caitlin glanced back at the door, which stood wide open. “I have to take everything off? Like everything, everything?”
“That’s right.”
“But the door’s open! What if someone sees!?”
“Caitlin, this is a perfectly normal inspection, I’ve done it tons of times. There’s nothing to be embarrassed about, I’ve seen it all before. So has everyone else in this school. So don’t worry about the door. Go ahead and get undressed.”
She glanced between me and the door for a few more seconds, then began to unbutton her vest. She slid her vest off, folded it and placed it on a desk. Then she did the same with her blouse, again sliding it off, folding it and placing it on top her vest. Here hands fidgeted at the waist of her skirt, of course she had it as long as she could, all the way down to her mid-thigh. I somehow managed to maintain eye contact, even with her being topless. I was behind my desk sitting, Caitlin in front of my desk. Her hands moved to the back of her skirt and there was a zipping sound, then the skirt fell down to the floor. She picked it up, folded it neatly and set it on top of her other clothes. She was now naked, but I couldn’t see much below her belly button due to my desk being in the way. I motioned with one hand, “Come over here and let me get a good look.”

Caitlin walked around to the side of my desk and I finally saw all of her. Her vagina was an innie with full lips and a tuft of red hair just above. I looked her up and down for a few moments, taking in her bare, pale smooth skin. “Alright Caitlin, I’ll need you to sit up on my desk here and spread your legs wide so I can get a good look.” Her eyes went wide and all the color drained from her face. “What!?” she exclaimed. “To determine what’s causing your tingling, I’ll need to do a thorough inspection. And that means you’ll need to show me everything.” She starred in disbelief and glanced back to the open door a couple times before finally moving. She slowly sat down on the edge of my desk then spread her legs a little, but it wasn’t good enough. “I’m afraid you’ll have to do better than that. Scoot back just a bit, raise your legs in the air and spread them as far as you can.” Caitlin complied. She moved back so her entire butt was on the desk now, she put her hands down behind her to support her weight, then lifted and spread her legs.
I leaned down to get a good look, her pussy lips inches away from my face. I used two fingers to spread her lips and reveal the rest of her pink kitty. “Hmmm….” I said aloud taking a closer look. Her lips were swollen and I could clearly see her juices dripping out. Just as I suspected, nothing wrong, she was just horny. I dropped my hand and looked up at Caitlin. She was quite nervous now, especially in this position. “I know what the problem is.”
“Oh god!”
“Its not that bad, perfectly normal. There’s actually nothing wrong with you, you’re just concupiscent.”
“What? What’s that mean?”
“The colloquial term would be horny. There’s a simple remedy. You need to have sexual intercourse. As soon as possible.” She stammered in disbelief. “Intercourse! But I’ve never...I mean...oh my god! I can’t believe this is happening to me! Isn’t there anything else I could do instead? I’ve never done anything like that before. Why now? Why is this happening today?”
“I’m afraid there’s no other recourse. You’re going to have to have intercourse with someone. As far as why its happening? Well, I’ve been seeing this a lot lately with some of the other girls. You’re just at that age where you have these needs. And that’s what it is. Its a physiological need, nothing to be embarrassed about. I could help you out, if you wanted.”
“Help me? You mean, have...intercourse with me?”
“That’s right. Like I said, you need to take care of this as soon as possible. This my free period, so I have the time.”
Caitlin thought about it for a minute, eyes darting in every direction, trying to think of an alternative. She was completely inexperienced with this kind of thing. She came from a very conservative family. That’s one of the reasons she was in an all-girls school, her parents didn’t want her around boys. She’d never even fingered herself before, she wouldn’t know how even she wanted. She needed my help and knew there was no other option. She sighed “Ok, what do I do?”
She wasn’t the only one that was horny. My dick was hard as it could be, starring at this beautiful naked virgin redhead right in front of me. She was still spreadeagle on my desk. I stood and began to undress. “What are you doing?” As my shirt came off I answered, “Sexual intercourse requires both people to be naked.” She really didn’t know, did she? “Oh, ok.” Next came my pants, my cock visibly hard in my boxers. I finished taking off my boxers and Caitlin was starring at my crotch, not sure how to react. I let her get a good look before clearing my throat.
“Uh, sorry. I’ve just never seen one before.”
“Didn’t you have sex-ed? They usually have pictures of the male genitalia.”
“No, my parents wouldn’t let me take it.”
“I see. So you really don’t know what comes next, do you?” She shook her head no. I knew she was a virgin, but I’d never met anyone who didn’t at least understand the mechanics of sex. No matter, I was a teacher after all. “You can go ahead and get down from the desk.” Caitlin put her feet down on the floor and stood up, the tip of my dick barely touching her skin. I sat back down in my chair, grabbed the lever at the bottom and let the chair lower as far as it would go. “Alright Caitlin, I know you’re nervous. I remember my first time and I was scared to ****. But its ok, I’ll walk you through it.” She nodded, glanced down again at my hard cock before looking away. Her face was crimson now, whether from embarrassment or nervousness, I wasn’t sure. Sitting down, I looked up at her salacious curves. “You’re going to straddle me. Once you do, lower yourself onto me. Use your hand to guide my cock into your pussy. When you get the tip in, continue to lower yourself until all of it is inside you.”
She looked at me aghast. “Your...it...it goes inside me?” “That’s right.” She seemed even more nervous “Oh, uh, ok.”
Caitlin did as she was told. She stood to one side of me, then swung a leg over until she was half squatting with me and my manhood between her legs. She lowered herself aiming for my cock. I sat and watched and didn’t move a muscle. She placed her hand gently on my dick, it twitched as she touched me. She put the tip at the entrance to her pussy then let go with her hand. Her whole body was tinted crimson now, busily pumping blood into every heightened nerve. Before she could do anything else, I placed my thumb on her clit and started moving it in a circular motion. She moaned loudly and her body began to quiver. Her eyes rolled back into her head as her shaking became uncontrollable. It didn’t take much for her to cum. But then again, this is the first orgasm she’s ever had.
Her legs gave out, her knees raised and toes curled as her first ever orgasm spread through her body, every pleasure neuron firing like it was the 4th of July. With the tip of my dick inside her, when her legs gave out, her weight brought her down engulfing the entire length of my cock. The sudden impalement of her wet pussy caused her to scream out loudly. As wet as she was, I still felt a bit of resistance around my cock as it went balls-deep. Damn, she was tight. Definitely the tightest pussy I’ve ever had. Her hands gripped my shoulders and she continued to cum. Her eyes still rolled back, knees lifted, toes curled, it seemed like her orgasm lasted for several minutes. As it eventually subsided, her feet fell back to the floor, she slumped down and her sweat soaked face fell against my shoulder. Her arms wrapped around me to steady herself.
My classroom door was still open and someone must have heard her scream because a moment later, a very concerned Ms. Williams rushed into the room to see what was going on. Wendy Williams was the senior math teacher, and not bad looking either. I kinda had a thing for her, but alas, she was a lesbian. A lesbian at an all-girls school, some ideas floated through me mind just then and I made a mental note to pursue that later. For now, Wendy was shocked at what she saw; the backside of nude Caitlin riding me. “What the hell is going on in here!” She demanded. Caitlin was still out of it and only managed a brief glance back with glossed over eyes, but otherwise didn’t respond. I answered “Hi Wendy. Ms. Caitlin here asked for a vaginal inspection, that’s all, nothing to worry about, I assure you.”

She didn’t seem convinced “Is it really necessary for you to have your penis inside her?” She bent over slightly to get a better look, she could see my balls and a tiny bit of my shaft impaling Caitlin’s pussy. “It wouldn't be a complete inspection if I didn’t.”
“Hmmm, well, can you at least keep it down? I’m trying to teach class.”
“Oh, yes of course, I’m so sorry.” She took another long look before turning around and heading back to her room.
After another minute of resting, Caitlin finally managed to lift her head. “Wha...what just happened?”
“Congrats, you just had your first orgasm.”
“Oh, I, uh…”
“Lucky for you, women can have multiple orgasms.” Shock appeared on her face as she realized it wasn’t over yet. “So, next you’re going to plant your feet on the floor, then lift yourself up and down so that my cock goes in and out of your pussy.” Caitlin got right to work. Feet on the floor, hands around my neck, she lifted her ass up until only the tip of my dick was inside her. I looked down and watched her pussy lips grip my thick cock. She lowered herself back down, again taking my full length. When it was all the way inside she pressed her mouth to my neck to stifle a loud moan. “Keep going, but faster this time.” She did it again, up, then down, but faster just as instructed. She kept going, getting faster and faster. She was just bouncing on my cock now. Using her legs to propel upward, then using gravity to come back down.
After a few minutes of this, when sliding down my pole, her knees lifted and toes curled, cumming for a second time. This time though, she almost immediately starting bouncing again, wanting more. Her moans would have been quite load if her mouth wasn’t muffled against my neck. I was starring at her bouncing tits. They brushed up against me as they bounced, I could feel her hard nipples against my skin. She kept at it and came again as I edged ever closer. I wasn’t going to last much longer considering how tight she was. My cock throbbed as she worked it over and over again. Just as I was about to cum, I grabbed her ass, pulled it down and thrust up, getting even deeper. That was it, I exploded inside of her. My orgasm just as intense as hers. She felt the hot cum inside her and her toes curled yet again, cumming at the same time as me.
I held her in place like that until I was empty, then slouched back down in my chair. Caitlin did the same, sensing it was over. Her whole body quivered against me, her breasts brushing against my chest as she breathed. We sat like that for some time. I recovered enough to gently tilt up her head. “And that’s what sexual intercourse is. Any questions?”
“What’s that liquid I feel inside me? Is that normal?”
“Yes. When a man orgasms, he ejaculates sperm. Also known as cum or jizz. Don’t worry, I can’t get you pregnant, you’re safe. But it will probably leak out of you for a while. Again, its normal.” I motioned her to get up and she managed to stand on shaky legs, cum streaming down her inner thigh. “Do you have another class? I can write you a note.”
“Thanks, yea, I’ve already missed half my english lit class.” I wrote her a note while she dressed. How to explain to another teacher what just happened? Well, it would probably be pretty obvious given her state. Her hair was a bit rumpled and cheeks flushed. And of course the jizz running down her legs. She had her skirt and blouse back on and was working on the vest when I finished her note.
Caitlin is excused for tardiness, she needed a vaginal inspection - John Doe
I handed it to her, still naked. She took once last glance at my dick, then left. She hadn’t even attempted to clean up.
What happens to Caitlin?
Disable your Ad Blocker! Thanks :)
The Rulebook
You find a Rulebook that lets you rewrite the rules any organization has to follow
A lucky protagonist stumbles across a magic book that lets them rewrite the rules.
Updated on Jun 12, 2026
by Ggnt
Created on Jul 27, 2017
by ashes2ashes
You can customize this story. Simply enter the following details about the main characters.
- 140,932 Likes
- 58,937,296 Views
- 8,543 Favorites
- 31,659 Bookmarks
- 6,702 Chapters
- 71 Chapters Deep
- All Comments
- Chapter Comments
