"Date" Night

The week drags by, but at last Friday afternoon arrives. Heather shows up at your place with a garment bag over her shoulder. She offer a brief, sweet kiss, then disappears into the bedroom. After a moment alone, she calls back to you to join her.

"I got us some stuff," she says as she opens the bag. "You told her to wear the schoolgirl costume, right? Well, I found a matching costume. And a wardrobe upgrade for you, too."

She hands you a pair of dressy slacks and a freshly-pressed shirt. You start to see where she's going with the clothing decisions when she pulls out her own schoolgirl outfit and starts to change clothes. You change, a choice made difficult as you and Heather trade teasing hands.

By the time you're both dressed, it's almost time. You lead your redheaded accomplice across the street and ring the doorbell. After a few moments, the door opens. You've angled yourself just enough to keep Tina from seeing Heather immediately. And in doing so, you keep the first look at the Asian beauty to yourself.

As agreed, Tina is wearing the schoolgirl outfit from her online profile. And immediately you realize it doesn't do her justice. The costume looks a size or two too small, and hugs her curves in just the right way. The bra you can just barely make out through the fabric juts her breasts out at you, pressing them together and giving you a perfect view of her cleavage. Her hips sway just ever-so-slightly, causing the hem of the skirt to ruffle in the barely-existent breeze. Her hair is tied in a pair of tails that hang off the sides of her head, running down to frame her tits.

"Miss Dream, I've had some.... unusual reports about you and another student," you start with a playful smirk. "I've brought her with me to discuss what you two have been up to in the biology lab." Heather moves into view, and Tina's eyes go wide.

"I can tell you what we've been doing, Headmaster Doe!" Heather exclaims, crossing the distance between her and Tina in record time. She plants a deep, tongue-filled kiss on Tina's lips, moving her back into the house. You step in as soon as there's space and close the door behind you. After a moment's enjoyment watching the scene, you gently pull the two apart to give Tina a chance to catch her breath.

"That's all we were doing, Headmaster," Tina says, quickly getting into character and adding a bubbly chirp to her voice. "Honest!"

"Is that so?" you say, "Well, the school board and the school's regulations both prohibit public displays of affection such as that. You're both facing several counts of breaking these regulations and could possibly be expelled. I'm hoping that by talking to you both at the same time, we can avoid that outcome."

"Aww, Headmaster.... The boys love it when we do that!" Heather giggles and cozies up to Tina as you find your way into her living room. The three of you sit, the girls on the couch and yourself in an overstuffed, oversized easy chair.

"And that's precisely the problem," you say, starting to enjoy the roleplaying and watching the girls get into it, as well. "You're going to give them the wrong ideas, which could be quite bad for you."

"Bad how?" Tina asks as she nuzzles Heather. "We like feeling good with each other like this."

"Well, those boys you mentioned could think they can take advantage of you. Emotionally, more likely sexually."

"Sex? Ew!" Heather spits, keeping in character. You have to repress a laugh. "Boys just have those nasty dangly parts. So ugly!"

"Yeah, girls have it made. We get pretty titties like these," Tina adds, cupping one of Heather's for emphasis. "And we don't have ugly dangly things."

"That 'ugly dangly thing' is called a 'penis,' girls. You should at least use something closer to the proper terminology. Slang terms, while often derogatory, are at least an improvement. Using 'titties' instead of 'breasts,' for example."

"It's still ugly," Tina says, sticking out her tongue and making a face. You notice the piercing and act on it.

"Young lady! Such jewelry is not permitted with the school uniform!" Tina's tongue disappears again.

"Well, we're not at school right now, Headmaster."

"While you're wearing the uniform, you're to follow all regulations regarding it, whether you're in class or elsewhere, as an example of a refined young lady. Now I'm afraid I'll have to apply the proper punishment. Over my knees, young lady. You'll have to receive your spanking."

Tina applies a shocked, then mock-fearful look and lays across your knees. You note how soft and warm she feels against you as you lift her skirt, revealing her bare bottom.

"And no underwear, either. Tsk, tsk. Miss Dream, you're breaking another dress code regulation there and added two more to your total for five. You spank your Asian prostitute, catching Heather's eye as your hand lands on her tight ass for the first time. Heather gives you an out-of-character thumbs-up, then turns her face into a mixture of fear and shock.

After the fifth strike, you let your hand rest on Tina's ass, gently stroking it as she mock-sobs in humiliation.

"Headmaster, may I get up now?" There's no real fear in her voice, and you realize how carefully controlled it is to sound as real as possible. You gain some respect for how she treats her trade.

"You may. Miss Heather, do you have anything to say for yourself? Any violations you think you should tell me about now?"

Heather thinks for a minute. "Well, yesterday one of the boys offered to let me look at his ug.. penis. He wanted to see my titties in exchange."

"And did you?"

"Yes, sir. I wouldn't let him touch them, though." She pauses, but then starts again before you get a chance to speak. "But I'm confused about something, Headmaster. Maybe you can explain it to me. How is that penis supposed to make us pregnant? It looked so small and squishy."

"Well, it appears this boy did not have an erection. An erect penis is a requirement for sexual intercourse resulting in pregnancy."

"So it gets hard? It still looked really small."

"The erect penis grows in size, both in length and thickness." Heather keeps a dubious expression on her face. Tina smiles wickedly.

"I'll bet Headmaster has an erection right now," she says. "Maybe he'll let us see what he's talking about? It'll make a great example for us to learn from." She casts doe-eyes at you, causing your willpower to shudder. But this is the fantasy, so you roll with it.

"Indeed I do, Miss Tina. And I will admit I got it from seeing your bare bottom just a few moments ago. So I suppose it's only right for you to see. But not a word of this, girls, otherwise you'll find yourselves expelled from school." You stand and undo your pants, letting them fall. Your boxers quickly follow, leaving your manhood standing proud at last. The girls look in awe at it.

"So much bigger than the one I saw..." Heather plays. "Can we touch it?"

"Of course. But be careful, as in this condition it can be quite sensitive."

"We won't break it," Tina promises. Her well-practiced hands are almost immediately on your balls. Heather lightly strokes your shaft with her fingertips.

"I don't think you could break it, ladies. But it's quite sensitive and your touch could bring me to a fast orgasm. That would be a bit of a mess, you see."

"A mess? How?" Heather should be a theater major, for all the innocence she projects.

"He's talking about cum. I heard some of the other girls talking about it. They said it tastes like salty candy."

"I like candy!" Heather's touches grow firmer, but her delicate grip lets you keep your control. "Can I taste your cum, Headmaster?"

"Oh, I suppose I can indulge you that much," you play along. "Miss Tina, would you like to try it, too?"

"Oh! Yes, please!" She giggles. "What do we do?"

"Well, Miss Heather is doing a fine job with her hand, but for what you girls want, it's quite common for a young lady to use her lips and tongue on the penis. The slang for that is 'blowjob,' as I recall."

The girls need no other preamble and get to work on sucking you off. Tina takes your head between her lips and gently teases the slit with the tip of her tongue. Heather suckles at the shaft, then starts to suck on your balls. The sensation nearly sends you sprawling back into the chair. You notice the girls' eyes meet, and before long the two are making out again, with your cockhead in between their twirling tongues. You shudder for a few long moments before you start to feel the familiar beginnings of your orgasm.

"Ladies, ladies, if you would please get down on your knees in front of me. Now press your faces next to one another...." You stroke yourself into an award-winning orgasm, your aim perfect as you blast one shot into Heather's mouth, the next into Tina's. You alternate until the ferocity of your orgasm fades. The last drops of cum dribble down onto Tina's blouse as you watch the girls play at tasting cum for the first time.

"I think I like cum," Heather says after swallowing her part of your load. Tina makes a show of swallowing and nods. "Can we have more?"

"Of course, but it will take some time. Not every man can keep his erection after an orgasm like that."

"Oh! Oh, no! It looks like some of Headmaster's cum got on my clothes!" Tina exclaims. "I guess I'll have to take it off before he spills more on it." Before you can take authority, her blouse comes off, leaving her in a pale-colored push-up bra.

"You should take that off, too. It's too pretty to get cum on it," Heather says helpfully. The bra quickly joins the blouse in a small pile across the room. You stare openly at Tina's chest. Her breasts are definitely larger than you'd previously thought, and her nipples stand out almost an inch long.

"You've got such nice, big titties," Heather says, pouting slightly. "Mine are just really small. Especially next to hers." She takes off her blouse; she doesn't have a bra on underneath it. "See? What do you think, Headmaster?"

"I think you both have lovely breasts," you say as you reach out to the girls. They move into position, letting you fondle a tit from each. You note a sharp inhalation on Tina's part when you pinch her nipple. You can feel your cock gaining strength again. So do the girls.

"Oh! It's getting big again, Heather!"

"So how does the cum make us pregnant, Headmaster?" Heather asks innocently.

"You let a boy put his thi.... penis between your legs, silly," Tina says mockingly. "In that hole where we usually put our fingers to feel real good together."

"That 'hole' is your vagina," you automatically correct, staying naturally in character.

"It looks too big to fit!" Heather complains.

"I don't think so," Tina says, standing up as you sit. "Can I see if it's too big, Headmaster?"

She doesn't give you a chance to answer as she turns and squats down on you, facing Heather. You can see red handprints on her ass where you'd spanked her earlier. Tina lines your cock up and slowly impales herself on it, moaning until she reaches your balls. Your hands reach around to cup her breasts.

"See? It's... tight.... but it fits.... Ohhh....." Tina starts to rock back and forth against you. Heather catches your eye and smiles, then moves in to kiss and lick at Tina's pussy and your cock. Tina makes a decidedly unladylike sound as Heather's tongue strikes her clit. You start to thrust upward into Tina's wet sex.

It seems all pretenses of roleplaying are off; Tina and Heather no longer act like the innocent schoolgirls they were once dressed as, nor are you the stern-but-horny headmaster. All three of you act as one in a carnal concert until Tina climaxes, her pussy milking your cock more tightly than anyone you've ever fucked, taking all your willpower to keep from coming right then and there.

"God... God, I haven't been fucked like that in a long time...." Tina admits as her climax fades. She pulls herself off your solid member and joins Heather on the floor for another passionate kiss before the two stare at the wet shine covering your cock. "Take it, Heather. I want to see that tiny pussy stuffed."