Harry decided to take off his shoes and socks and did as he was told, standing before Madam Pince and Luna. Heart beating faster for a very different reason than it was when he first stepped into the library, Harry pulled off his shirt.
"May I please see your cock, Harry?"
"Why do you want to see his cock?" Madam Pince asked.
"I want to see it so I can touch it. I want... I want it in my mouth. I want it in my pussy. I want you to fuck me raw, and I want to fuck you even harder than that. I want your hot cum all over me, in me, everywhere. I want to watch you do all of that to Madam Pince too. I want the three of us to fill the library with screams while I'm learning to unleash my slutty side," Luna said. Her words came out nervously at first, but the longer she talked the more confident she sounded.
Madam Pince smiled "We should probably stop your training for now Luna while we deal with Harry"
Luna smiled brightly, bending over a table. Madam Pince walked up behind her, caressing Luna's ass, slowly pulling her skirt up and over her pert, tight little ass.
Two things at once surprised Harry about this view:
First, that Luna wasn't wearing any panties.
Second, that Luna had the end of a butt plug sticking out of her ass.
That would explain why she looked so uncomfortable.
"How long has that been there?" Harry asked without thinking.
"Since before I had her go looking for you," Madam Pince said, grabbing the end of the plug and slowly pulling it out of Luna's ass. "And that was quite a while ago."
"He was harder to find than I expected. OH, FUCK ME!" Luna exclaimed as Madam Pince pulled a very large butt plug from her ass. Madam Pince marveled at the sex toy before setting it down on the table next to her polished wooden box.
"Well, you did find him, that is worth some commendation," Madam Pince said, running a finger down to Luna's pussy and stroking her slightly. Luna whimpered with pleasure, looking back over her shoulder at Madam Pince and Harry. Madam Pince continued, "Of course, you did interrupt me, and I said we would address that."
Madam Pince took her finger from Luna's pussy and opened up the polished wooden box on the table. Harry craned his neck and got a good look at a surprisingly comprehensive collection of high end sex toys. Madam Pince rooted around through them before settling on pulling out a bottle of lube and another butt plug and setting it down next to the first, showing it to be significantly larger.
Luna's eyes went wide at the presentation of this new toy, but not from fear. No, that was definitely a face of anticipation.
"Would you like to help with Luna's punishment, Harry?" Madam Pince asked, generously pouring some lube on the new plug.
"Sure," Harry said, walking up behind Luna. For a girl without much of an ass, what she had looked very nice. Tight, fit, the kind of ass that could go for a while. He wanted to touch her, but not wanting to draw Madam Pince's ire, he didn't. Instead he stared into Luna's eyes as she looked up at him with anticipation and primal want..
Having fully lubed the butt plug, Madam Pince gave it to Harry. "Until today, the one I pulled from her was the largest she's ever taken. Let's set a new record for her together."
Tentatively, Harry lined the cone-shaped toy up with Luna's ass, teasing it around her tight little hole. Even though she'd already had a sizable toy in there, you wouldn't know it for the modest resistance he felt. Still, Harry pushed the plug forward, relishing Luna's sharp intake of breath, the way she gripped the edge of the table slightly, that soft little moan as he pushed it in further.
"More, please," she whispered.
Harry didn't want to push it in more. What he wanted to do was pull off his pants, whip out his cock and fuck Luna's pussy and ass silly, spraying her down with his cum. The anticipation was killing him, but this new game was too hot not to enjoy. Harry pressed the plug in further, watching as her asshole stretched obscenely around it, enjoying the way she shuddered more intensely with each fraction of an inch her ass was stretched.
It almost didn't seem like she could take the last flared out portion of the base, it just seemed too wide, but with a yelp and a pop it slid into her ass, only the end of the plug sticking out.
"Very good," Madam Pince said. "Now, Luna, do you think you've learned your lesson about interrupting?"
"Oh, god yes, Madam Pince," Luna purred.
"And will you be interrupting me again?" Madam Pince said.
"Many times," Luna promised.
Madam Pince shook her head, an amused smile on her face. "Clearly, I've got a lot more to teach."
Clearly, Harry had underestimated how depraved the school librarian was.
Madam Pince gently grabbed Luna by the hips and coaxed her to stand up. With a plug this large inside of her, Luna was unsteady on her feet, but she followed the librarian's instructions eagerly, first turning around and then dropping to her knees. Looking down at her as she looked up at Harry hopefully, Luna looked so inviting. If she only moved forward another half a foot, she'd have been able to suck Harry's cock if it were out, but Harry was sure Madam Pince staged it this way for a reason.
Madam Pince walked behind Harry pressing her large, sweater-clad breasts against his back. Even through the sweater, he could feel her nipples, hard and thick like bullets pressed against him. Reaching around, Madam Pince rubbed his cock through his jeans.
"That got you excited, didn't it? Seeing her moaning and shaking like a whore as you pushed that toy into her?" Madam Pince whispered into his ear.
"Yes, that was definitely hot," Harry said.
"Good. Why don't we show Luna how hot you think it is?" Madam Pince proposed, reaching around to undo his belt, dropping his pants to the floor, then pulling down his underpants to join them. Harry's cock in all of its ten-inch-long, thick glory, stood out proudly, getting first a sound of approval from Madam Pince, and Luna's jaw actually dropping open. The precum at the tip was already flowing freely, a small drop of it even dripping slowly off the head in a strand.
"That can't... that can't be real," Luna said, gaping at it.
"Oh, I assure you, it is. Never underestimate a man based on his looks. Some of the most traditionally handsome men you'll find may boast a three inch dick or might not be able to get you off with a map and the best vibrator you'll find, while those you underestimate may have the skills of a sex god or a cock like this," Madam Pince said, reaching around, slowly, expertly jacking his cock.
Harry groaned. "I like to think I bring the skills and the cock. I'm... oh man that feels nice... I'm really proud of my abilities to make girls cum."
"And we intend to make use of both," Madam Pince said. Somehow, she leaned in closer, close enough to completely crush her breasts against his back, letting Harry know that she was still completely clothed and completely in charge while whispering huskily into his ear. "The thing I love about young guys like you is that you've got stamina to spare and can cum like fountains, and rest assured, I want your stamina and your cum. I want to train Luna, but I want what you've got, and I'm going to get that first, but I want you to last, and if you're going to last, we'll need to drain these balls of yours a little first. There's a lot of ways we could do this, but wouldn't me jacking you off until you drain them all over Luna's pretty little face be the most fun?"
"Yes," Harry agreed.
Madam Pince kissed the side of his neck. "Good boy."
To Luna, louder, she said, "Let down your hair and take off your dress, Luna."
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