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Chapter 2
by jonjacobs64
Post your entries here
High Flying Truth or Dare
My trips to Kansas City are usually extremely boring.
The College Board always buys my ticket to the AP test grading center, and my seat usually sucks. This trip was no exception – I knew I was going to be stuck in the center seat all the way in the back. You know, the one next to the bathroom, but you still have to climb over someone to get there.
Needless to say, I was not looking forward to this flight. But as I approached my cheap-ass seat, I discovered to my immense surprise that I would spend the next couple hours snugly nestled between two outrageously beautiful young women.
The window seat was occupied by a stunning woman with thick, black hair. Her skin was pale and soft, and she had perfectly-plucked eyebrows and large, full lips on her tastefully made-up face. Her tits were to die for, easily a D-cup, which stood out beautifully in her form-fitting white camisole. Skin-tight black leggings left only one question to the imagination: panties, thong, or commando?
In the aisle was an equally beautiful woman, though with very different qualities. She had olive skin and brown hair, a seemingly half-Asian complexion with bright brown eyes and no makeup on her naturally beautiful face. Her small black t-shirt was paired with a short pleated skirt that revealed luscious thighs and toned calves.
They were talking to each other as I approached. I stored my carry-on in the overhead bin across from our seats. Weirdly, there was no one sitting in the bank of seats across from us, but I made no move for the extra room. “Hi,” I said, pointing at the seat between them. “This is me.”
“Oh, cool,” said the girl on the aisle. She sat up straight and pulled her calves in, and I slid off my backpack and climbed over her tight body, brushing her bare legs with my own. I fell into the seat and pushed my backpack under the seat in front of me. I couldn’t help but take a sidelong glance at those long silky legs, which I noted were a lighter shade than her face.
I straightened up, clipped my seatbelt over my shorts, and did what I never do on a plane. I introduced myself.
“I’m Simon,” I said, trying to address both women at once.
“Hey Simon,” chirped the woman in the aisle. “I’m Christine.”
“And I’m Ava,” smiled the one by the window.
“Nice to meet you both,” I said. “You guys are friends?”
“Yeah,” said Christine. “We went to high school together, and now we’re room mates in college.”
“Nice,” I replied. “So you’re headed home?”
Ava answered, “Actually, we’re meeting our friend Jillian in Kansas City. She’s spending the summer there with her folks, and she’s _dying _of boredom. So Chris and I took a few days off work to go cheer her up.”
“Well, a friend in need is a friend indeed,” I smiled.
They both laughed, and Christine said, “Well, then Jillian is definitely a ‘friend indeed.’ She always needs something.”
I came to learn the basics about the girls. Ava and Chris (as she liked to be called) were in a sorority with Jillian and shared a big house off campus with 9 other students. Christine was a music major and had played violin since she was three, and Ava planned to major in psychology and enjoyed playing volleyball and keeping up with the latest fashions.
“And what about you?” Ava asked. “What do you do?”
“Oh, you’ll think it’s terribly boring,” I said.
“No come on, tell us,” Chris said.
“I’m an AP English teacher,” I told them. “And believe it or not, I’m on my way to Kansas City to spend the next two weeks grading exams.” They didn’t say anything, but I’m pretty sure I saw them make eye contact with one another.
“So, wait, you’re like a professor?” asked Ava.
“No, just a regular high school teacher,” I said. “A bunch of professors do come to the grading. Professors don’t get paid as much as you’d think, so the extra money can be helpful in the summer. But there are plenty of high school teachers like me. This is my third year, and I’ve been doing it since I started teaching.”
It was the weirdest thing. Both of them had gotten completely quiet, and for the first time in my life, I was grateful that the in-flight safety announcements began. We sat in silence as the flight attendance mimed putting on rubber masks and the plane began to taxi to the runway.
“Okay, shit, I’m going for it,” Christine said. Even though the plane was moving, she unbuckled her seat belt and stood in the aisle. She opened the overhead bin across from us—the same one I used to stow my luggage—and unzipped the side of a duffel bag. She strained to reach something inside, and I simply couldn’t help but ogle her long legs, barely clad by the short skirt she was wearing. I stared with lascivious fascination as she ruffled around in her bag, bracing herself in case the plane lurched.
She finally found whatever she was looking for, closed the bin, and dived back into the seat next to me right before a flight attendant arrived to **** her to sit down. “Sorry,” she told the attendant, who hurried back to take her own seat before takeoff.
“Did you get it?” Ava asked over me.
“Yeah,” Christine said.
“Well, go on then,” her friend urged.
I was utterly bewildered by this behavior until I could finally glimpse what was in Christine’s hands. An essay with the word INCOMPLETE written in neat red letters at the top.
“What do you have there?” I asked.
“So my bitch of an English professor thinks I can’t write even though I was in, like, the top 25% of my English class back home,” Christine said. “She told me I had to take an incomplete and rewrite my final essay over the summer or I have to take this fucking class all over again.”
“Sounds rough,” I said. I couldn’t empathize—I have always been a stellar writer and served as the editor of my high school and college newspapers. People called me a nerd, and I finally learned to live with it.
“Rough I could handle,” Christine groaned. “This is brutal.” I wasn’t entirely sure where this was going, so I waited to see what she would say next. “So, I guess…” she trailed off, suddenly seeming unsure of herself.
“Look,” Ava said from the other side of me. “What my friend is trying to say is that she could really use your help.” I looked quizzically at Christine, who gently nodded her head. Ava continued, “So, would you be willing to take a look at her essay?”
Back in my own college days, with late-night debates about philosophical and moral quandaries, I would have loved to think hard about this ethical dilemma. Would this be cheating or just helping? Do I owe anything to the person in need, and is that more than I owe the mores of my profession? What is the proper balance of mercy and justice?
But in the moment, with a modern-day damsel facing the only distress I could reasonably rescue her from, the answer came immediately to my lips. “Sure,” I said. “Happy to help.”
Christine’s teeth gleamed through her broad smile and her light brown eyes lit up with joy. “Oh my God THANK YOU, Mr.…” she gushed at me.
I may even have blushed a little.
“His name is Simon,” Ava reminded Christine at the same time that I said, “Mr. Clark.”
“Thank you, Mr. Clark,” Christine smiled. “This is huge.”
“No problem,” I said. “Let me just get my pen.”
I pulled my own trusty pen from my backpack, my arm accidentally brushing Christine’s bare leg in the process. I admit that my loins stirred just a bit, but I worked hard to pull myself together. I read the essay while Ava and Christine both put in their airpods. Hardly seemed fair, but I guess I did sign up for this.
The essay wasn’t terrible, and I could tell why the professor (who I assumed was not, in fact, a bitch) hadn’t just failed Christine. But the grammar was sloppy, there were several unnecessary repetitions, and the whole thing needed reorganizing and a conclusion. Within a half-hour, I had annotated almost every sentence of the essay, and I was confident that if Christine just followed my suggestions, she’d ace the assignment.
I was ready to give Christine her essay back, but her eyes were closed. I tapped her on the shoulder. “All done,” I said. But she didn’t stir. I turned to Ava and tapped her on the shoulder as well. “Chris is out like a light,” I said. But Ava’s eyes were also closed, and she also didn’t respond to my touch. Looking around, I noticed that everyone nearby seemed to be asleep, including the people in the seats in front of us on both sides of the plane. (Thankfully, they’d stay asleep until we landed!)
This was certainly an interesting development. Unencumbered by anyone else’s prying eyes, I allowed myself to drink in Ava’s voluptuous form. About half of her gorgeous breasts were on display, rising and falling in her camisole top, the chilly air of the plane causing pencil-eraser nipples to stand out in the thin fabric. Such a prolonged downblouse view was the stuff of fantasies, and here it was in the flesh. Making sure no one else on the plane was paying attention to me, I leaned over and put my face right next to Ava’s chest, getting as close as I dared without touching her. I was definitely getting hard, and I pulled away before I did anything truly stupid.
Getting my dick under control and turning back to Christine, I tried rubbing her shoulder. “Hey,” I said. “I’m done with your essay.” Christine jolted awake, throwing her hand to her chest in surprise, and then seemed to remember where she was. I said again, “Sorry to wake you. Just wanted you to know I’m all done.” Christine flashed her winning smile again and accepted the paper from me. She looked over my comments, grinning ear to ear.
“Oh my God, Mr. Clark, this is incredible. Thank you so much!”
“It’s my pleasure, really,” I said. “I’m happy to help. And you can call me Simon.”
“You’re a life-saver,” she said and unbuckled her seatbelt. “I’m just going to put this back in my bag.” Ava let out a little snore as Christine stood up, once again displaying her killer legs. Without Ava to catch me in an act of minor depravity, I let my eyes follow my dick’s lead. With Christine once again fussing with her duffel bag, I leaned forward and peeked under her pleated skirt.
I remember literally thinking Holy shit as I saw her cute bubble butt entirely on display and a thin, black thong keeping her pussy out of view. I pulled back quickly and looked out the window (okay, I looked at Ava’s tits) while Christine finished with her gear. My mind was racing, and a wicked little idea got lodged in my brain. Christine sat back down, and I turned my attention back to her.
“Thank you again,” she said.
“Hey,” I said, “I’m glad you can find some success. I think this calls for some celebration, don’t you?”
Her eyebrows rose. “What do you mean?”
I bent forward and pulled a box—basically the shape of a large box of chocolates—out of my backpack. “I usually bring these from duty free for some of my buddies at the testing center, but I can get more when we land,” I said. I opened the box to reveal 24 mini bottles of ****, a sampler tray that you are definitely not supposed to bring on a plane.
“Whoa,” Christine said. “That is beautiful.”
“Take your pick,” I said. “Only make it quick so the stewardess doesn’t see.”
Christine instantly reached for whiskey, saying as she twisted the cap off, “You’re supposed to call them flight attendants now.”
“Oops, party foul,” I teased. “I guess I need to take one too.” I slipped a scotch out of the sampler and made a toasting motion toward Christine. We clinked bottles and downed them in a single gulp.
“Oh man, that is is good,” she said. “Thank you!”
“You’re very welcome,” I said, collecting her empty bottle and putting it in my bag. “I’d give some to Ava but…” I gestured at the sleeping girl, and Christine smiled.
“No surprise there,” Christine said. “Ava sleeps like a rock.” To prove her point she reached across me and shook her friend’s shoulder. Ava’s face didn’t budge, though her tits did jiggle nicely. Christine laughed. “We love fucking with her at the sorority house.”
“What do you mean?” I ask, my heart racing but my face staying cool as a cucumber.
“Oh, she just falls asleep all the time. Doing homework, watching movies, even during meetings. We like draw on her sometimes or take stupid pictures. It’s insane; I’ve never seen anyone sleep like her.”
“Sounds pretty peaceful,” I suggested. “I usually need some more of these to zonk out like that.” I took out another small bottle of **** and offered one to Christine. To my delight, she instantly accepted. We drained our liquids, and I stashed the bottles once again.
“Dude, Ava is missing out,” Christine said. “She’s such a party pooper.”
“Oh, so we’re partying now?” I teased.
“Hell yeah,” she said. “Give me one more.”
“Help yourself,” I said with a grin. I was already feeling a light buzz from the shots I’d taken, and I don’t think Christine noticed that I didn’t drink a third. She enjoyed hers, though, and wiped her mouth with the back of her hand.
“Hey, want to see something funny?” Christine asked.
“Always,” I said.
Christine reached across my body toward her friend, and in one quick motion grabbed the hem of her top and yanked it down. She tucked the edge of the camisole under one of Ava’s massive boobs, which now rested completely exposed against her sleeping chest. The breast was pale and soft with a gorgeous nipple and a tasteful round areola. I couldn’t believe what I was seeing, and my mouth hung open in surprise while my eyes widened in delight.
“Ha, that is funny,” I said, not knowing how else to reply. Christine was laughing now, seemingly unconcerned about drawing attention. I was nervous we’d get caught, though. Our neighbors were still all sleeping, but as I looked up the aisle, sure enough, a middle-aged guy was walking our way, heading to the bathroom. “Hey, someone’s coming,” I said. “You should cover her up.”
“Nah,” she said. “I think she looks great.”
“Chris, come on,” I said, enjoying Ava’s predicament but not actually wanting her to get in trouble.
“If you’re so concerned, you cover her up,” she said, wickedly. “I dare you.”
It was obvious that Christine was happy to leave Ava exposed to the stranger heading our way, so I acted fast. Gripping the camisole between my fingers, I slid the material up Ava’s left breast, dragging my hand across her soft flesh as I tried to restore her shirt. I did a hasty job, and she still looked pretty akimbo, but she was sleeping peacefully and the dude passed us without even looking our way.
Christine was clearly loving this situation. “Hey, I’ve got another dare for you,” she said. “Pull her tit back out until you hear that guy’s toilet flush.”
This was the moment of truth, and I took a second to consider. If I refused, like the gentleman I pretended I was, then Christine would call me a dweeb, put on her airpods, and I’d be reduced to reading The Return of the King for the third time. But if I took the bait, indulged my wicked side, who knew where this might lead? Ava was still sleeping deeply, and clearly it’d make Christine happy…
“Fuck it,” I said, returning my hands to Ava’s chest. My dick hardened in my shorts as I pulled Ava’s top down again, tucking the fabric neatly underneath the large breast just like before. I stared, openly, and I’m pretty sure Christine was enjoying the view as well.
“Dare you to do the other one,” she said, basically verbalizing my inner thoughts.
“A dare’s a dare,” I said, returning with perhaps a bit too much eagerness to Ava’s chest and pulling out her other breast. I didn’t even try not to grope her as I exposed her tits to the chilly air.
After what seemed like ages—during which my eyes feasted upon the otherworldly sight of Ava’s perfect pair—the ridiculously loud toilet flushed right behind our seats. I hastily repositioned Ava’s top and the dude exited the lavatory, walking by again without casting us a glance.
“Holy shit,” I said. And, throwing caution to the winds, I opened my magic box back up. “Here.” Without a word, Christine selected another small **** and downed it in one gulp. “You are wild,” I said.
“You have no idea,” she purred. I laughed, and she did too.
“So, that’s what being in a sorority is like, then?” I asked. “Everyone’s pulling out their tits all the time and playing Truth or Dare?”
“Yeah, pretty much,” she said.
“Sounds fun,” I said. “Wish I could join.”
“Oh well!” she teased. “You just have to fantasize about us each night before bed, I guess.”
“Now why would I do that?” I winked. (Yes, I literally winked at her!) I paused a moment and then ventured, “Well, how about at least the Truth or Dare part?”
“What do you mean?” Christine asked.
“Clearly you like dares. So let’s play. Right here, right now.” I didn’t wait for a response. “You’re up first. Truth or dare, Christine?”
I actually think I caught her a little off guard. She had enjoyed teasing her friend, but now, in a way, the tables had turned.
“Um, truth,” she said.
“Classic,” I said. “Always start with truth…” I thought for a moment. Ridiculously sexy ideas tumbled one after another. _What’s your favorite position? How often do you have sex? Tell me about the last time you had sex? Do you swallow? _And so on. If I was too vanilla, this idea would wither and die, but if I went from 0 to 60, I didn’t think she’d play along.
“Okay,” I said. “Have you and Ava ever kissed?”
“Oh, good one,” she said. “Yeah, we’ve kissed twice.”
“Oh, shit!” I said. “Do tell.”
“Well, once was just during Truth or Dare, so maybe it doesn’t really count. But actually, I really liked it, and I asked her later if we could kiss again. She said yeah, and we kissed.”
“And…” I prompted.
“And…. I really liked it again!” Christine confessed. “But Ava’s not bi so she wasn’t very comfortable and that’s as far as it went.”
“Nice story,” I said. “Truth or dare?”
“Hey, no fair! It’s your turn.”
“Well, you already gave me like three dares, so I gotta catch up.”
Christine pretended to pout. “Okay fine. But it’s going to be truth again.”
“I can live with that,” I said. I thought for a moment. Then, “What’s the sexiest piece of underwear you own?”
“Honestly, I don’t have any particularly sexy underwear,” she said. “Never really had the money for it.”
“So, I guess you’re already wearing your sexiest underwear!” I teased.
“Yep,” she agreed.
“Well, truth or dare?” I prodded.
“Okay fine, dare!” she said.
I instantly replied, “I dare you to show me the sexiest piece of underwear you have own.”
“Haha, very funny.”
“I’m serious. Like I said before, a dare’s a dare.”
Maybe Christine is particularly uninhibited or maybe the **** was getting to her or maybe some of both, but after a moment of reflection, she said, “Okay, I can do that.” She lifted the hem of her skirt so I could see her legs all the way up to her thong, which still tantalizingly hid what I assumed was a marvelously juicy pussy. She quickly put her skirt back down and then shot at me, “Truth or dare, big man?”
“I’ll go with truth this time.”
“Good because I want to know this. Who do you find more attractive, Ava or me?”
“Well, that’s hardly a fair question,” I replied coolly.
“What do you mean?” she asked.
“Well, I’ve seen Ava’s tits, and I must admit, they’re pretty fantastic. Haven’t seen yours, though.”
I swear Christine blushed. “So you find her more attractive then?”
“For now,” I said, locking eyes with Christine and then ostentatiously scanning her body with my gaze. “Truth or dare?”
“Truth.”
“Would Ava enjoy playing this as much as we are?”
“Yeah, I think she would. She loves Truth or Dare, actually,” Christine said. “So your turn. Truth or dare?”
“Dare.”
She thought for several seconds and then said, “I dare you to wake up Ava, but you can’t use your hands.”
“Shit, that’s a good one,” I said.
“I know. Thank you!”
“All right, let’s see here…” I tried simply pressing my arm against Ava’s, but it did no good. I nuzzled her shoulder with my face, but still she slept on. Christine was clearly enjoying this challenge, and I decided to go for broke. I leaned in and placed my face right between Ava’s pillows. I wiggled my face around, not quite motorboating her but also a little bit motorboating her. This was enormously hot but she still didn’t wake her up. “What the fuck?” I said, and Christine was laughing out loud.
“I told you she sleeps like a log,” Christine replied.
I thought about my challenge and tried a different tack. I leaned over and licked Ava’s exposed neck, tickling it with my tongue. She slept on, so I started kissing and sucking, licking and blowing, nibbling and ruffling. Fucking nothing. Finally, I took a deep breath and blew a giant raspberry on her neck. I pulled back and watched in awe as Ava slowly stirred, moved her hand up to rub her neck, flutter her eyes open, and pull her airpods out of her ears.
“Are we landing?” she asked groggily, completely unaware of what had been done to her.
Christine and I both laughed, much to Ava’s confusion. Christine told her she fell asleep while I was fixing her essay and that we had celebrated with some contraband ****. She also told Ava that we’d started playing “her favorite game” and that she had dared me to wake her up without using my hands. She did not tell Ava about her several minutes of boob-exposure or the wildly inappropriate few seconds I had spent with my face nestled between her tits.
Ava seemed charmed by the whole story. “So, how’d you wake me up?” she asked.
Playfully I replied, “I’ll show you.” I leaned my face toward her neck, and she didn’t flinch in the slightest. I blew another raspberry, and she laughed as my lips tickled her skin.
“Nice one,” she said, rubbing my saliva off her neck. “Now, let me see this **** situation. I’ve got some catching up to do.”
“Yeah, and you’re also like ten dares behind,” I teased. “So take a couple of these, and let’s play catch-up.”
Ava chugged two mini-alcohols immediately and held the third in her hand while she laughingly said, “Okay, no problem. Truth.”
I was ready for this. “Have you ever kissed Christine?”
She smiled, seemingly a bit embarrassed. “Yes,” she said.
“Come one, tell me more. How many times.”
“It was just once,” she said. “During a game of Truth or Dare.”
“Oh, boo,” I said. “Liar! Chris already told me you kissed twice!”
“What? What the fuck?” she said.
“That calls for a consequence,” I said, triumphantly.
“Ugh, what do you mean ‘consequence’?”
“If you don’t do the truth or dare, you have to have a consequence.”
“How is that different from a dare?” she asked.
“Clearly you girls don’t play this game right.” I felt like such a teacher right then. “A consequence has to be something that exceeds the boundaries of the game.”
“Like what?”
I thought for a moment. “Okay, yours is going to be in two parts.” Christine was grinning with anticipation. “First, make your best o-face and take a selfie.”
“Oh my God,” Ava said, but even as she protested, she was pulling out her cell phone. She made a very convincing face—one that made me fantasize about how to make it real—and snapped a picture.
“Nice one,” I said. “Now set that as your lock screen, and don’t change it until you leave Kansas City.”
Both Ava and Christine clearly thought that was hilarious, edgy enough to be funny but not so mortifying as to be out of bounds. To my utter delight, Ava complied, showing me the orgasmic expression anyone who glanced at her phone would see for the next several days.
“Okay, fuck, this is getting real,” Ava said. She drained her third mini **** and both she and Christine took another. I continued to refrain; better to keep a cool head in this situation. “Christine, truth or dare?”
“Dare,” she said without hesitation.
“All right. Why don’t you give our new friend here the kiss you always wanted to give your English teacher in high school?”
Christine laughed and looked me in the eye. “Okay, Mr. Winter. Get over here.” I leaned in eagerly, and Christine smashed her lips into mine. She explored my mouth with her tongue, ran her hand through my hair, and breathed heavily and deeply for much longer than I expected. I emerged from the kiss panting and definitely aware that our game had passed into another level.
“Well, Ava?” Christine offered.
“Dare,” her friend said.
“Now, why don’t you give our new friend here the kiss you always wanted to give your sister’s boyfriend?”
I looked at Ava. “Older sister, or younger?”
“Five years older,” she said with a smirk. “Looks about right…” She leaned in and slowly, seductively, sexily started to kiss me. Christine’s kiss had been bright and passionate; Ava’s was deep and strong. She moaned as we kissed, and the only thing she copied from Christine was running her hand through my thick, brown hair.
We came up for air. “That was extremely hot,” I said. “Your sister is lucky you didn’t steal her boyfriend.”
“Oh we totally hooked up,” she said. “I just never got to kiss him.” We all laughed at that. “Well, Simon,” Ava said. “Truth or dare?”
“Truth,” I replied.
“Okay,” she said. “What’s been your favorite part of this plane ride so far?” It was a great question. So many possibilities! I thought for a moment and decided to see how flirtatious I could be. “I’d say a pair of the hottest kisses I’ve had in a long time.”
“Nice,” said Ava. But Christine made a buzzing sound and said, “Liar!”
“What do you mean?” I asked.
“How about when Ava’s tits were all hanging out or when you practically motorboated her while she was sleeping?”
I could have died. To be exposed like that felt awful, and my heart sank into my stomach. I knew I’d have to try to apologize and dig myself out of that situation, and I turned to Ava to explain myself. But she had a huge grin on her face.
“Fucker,” she said. Then, looking at Christine, she continued, “I guess you couldn’t miss your chance to get a good look at the girls?” She pressed her boobs together with her hands, making them strain against her camisole. Christine laughed, and relief flooded my entire body. Ava looked at me and said, “She’s always pulling my shirt off when I fall asleep. First time on a plane though!”
“That you know of,” I joked.
“Hey, good point,” she said, narrowing her eyes playfully at Christine.
“But hey, you got a consequence, fucker,” Christine said. “Cause we all know those tits are to die for.”
“Guilty, as charged,” I said.
Christine thought for a moment and then said, “OK yours is also in two parts. First, unlock your phone.” I was nervous about where this was going, but I pulled my phone from my shorts pocket and entered my passcode. “Now give it to me.” I handed her the phone, and my heart sank as she rose and walked to the bathroom.
I turned to Ava. “What’s she going to do in there?”
“No clue,” Ava said. “Good luck!”
Christine was taking her time, and I didn’t want to lose momentum in our game. “Here,” I said, fishing two more alcohols out of my case. I handed one to her, which she downed. Then, I unscrewed the second … and handed it to her as well. She smiled and threw it back. “Truth or dare?” I said.
“Dare,” she replied.
I was ready. “I dare you to agree to the suggestion I make when Chris gets back.”
“Oooh, I like it,” she said. “Okay, deal.”
The lavatory door opened, and Christine stepped out. She handed me my phone, which was locked again. “No peeking,” she said.
“What did you do?”
“You’ll see when we get off the plane,” she replied impishly. “Now, did I miss anything fun?”
“Not really,” Ava said. “But Simon said he had an idea for the game.”
“Oh?”
“Okay yeah,” I said. “Here’s the next level. Let’s play Double Dare or Consequences.”
“What’s that?” asked Christine, clearly interested.
“Well, here’s how the double-dare will work. I get to dare both of you each round. And then you both work together to come up with a dare for me. If someone doesn’t do the dare, they have to do a consequence.”
“Sounds serious…” Christine said.
“Sounds great to me!” Ava said enthusiastically, smiling at me and fulfilling her final single-dare.
“Well, if Ava’s up for it, I’m up for it.”
“I’m down,” Ava said.
“Great,” I said. “And it’s my turn to ask. So, here’s your double-dare.” I paused for a moment to build tension. “I dare both of you to give me a piece of your clothing.”
“Oh, good one!” Ava said. Christine looked less sure.
I admit that this one was a little unfair. Besides her camisole and leggings, Ava was wearing sneakers with ankle socks. Christine, though, just had her t-shirt, skirt, and sandals. I knew she couldn’t lose any of those, so I figured I’d get my hands on some of her underwear. Ava could just hand me a sock, but I’d still come out ahead.
Christine sighed. “Well, a dare’s a dare,” she said. Without standing up, she picked her ass up off the seat, reached under her skirt, and slid her underwear down her smooth legs. She dangled her black thong off her forefinger and extended it to me. “To remember me by,” she laughed.
“As if I could forget!” I said. I comically folded put the underwear and slid it into my pocket. I looked at Ava. “Well?” I asked.
“Okay, Teach. Just a sec.” Ava unbuckled her seatbelt and crawled over Christine and me. She went into the lavatory, and I started to get excited.
“I see what you mean,” I told Christine. At her quizzical look, I continued, “She really does love this game!”
“Oh I know,” Christine said. “She can’t get enough of it at the house.” She added, “What did you talk about when I was in the bathroom?”
“Oh, I dared her to agree to whatever I next suggested.”
“Perv!” she shouted. “You tricked her into this double-dare shit.”
“Well, do you think she regrets it?” I asked with a smile.
“Not a chance,” Christine replied.
The lavatory door opened, and Ava came out. She crawled back over Christine and me and resumed her seat. Opening her hand, she deposited in mine another pair of underwear. It was an unremarkable pair of pink panties but one that I knew I’d cherish forever.
“Nice work,” I said, and Ava grinned as I again folded and deposited my prize.
“Okay, our turn!” Christine called. Both girls thought for a moment. They made eye contact? “Should we?” Christine asked.
“Yeah, I think so,” Ava replied.
I had no idea what they were about to say.
“Okay,” Christine said. “You’ve seen a lot of us, but we haven’t seen much of you. We double-dare you to show us your package down there.”
I swallowed hard. This was it. I told myself to play it cool, to swallow my insecurities, and to go for it.
“Hey, fair enough,” I said. I started unbuttoning my shorts, careful to be sure that a flight attendant wasn’t coming. I unzipped the crotch and tugged the shorts down a little. I lifted the hem of my black boxers and leaned back so the girls could take a look. I’m not a giant, but I’m not pathetic either. Thankfully, my little man wasn’t completely shriveled, and it also wasn’t raging hard. Just sitting there, full of potential energy, ready to be awakened at any moment.
“Nice,” Ava breathed.
“That is definitely the best teacher’s cock I’ve seen,” Christine said.
I kept showing off while I said, “And how many teachers’ cocks have you seen?”
“Hey, we’re not doing truths anymore!” she replied. “So just accept the compliment.”
“I bet Mr. Winter would have accepted that compliment, too,” I joked. Christine playfully punched me in the shoulder, causing my dick to bounce an inch or two. We all laughed, and I tucked myself away and started zipping back up.
“Wait,” Ava said quietly, and I froze. “We get to do another double-dare.” Curious as to where this was leading, I just listened. “And then you can do two in a row.”
“Okay,” I said, my cock in my underwear but my shorts still open.
“I double-dare you to get it hard for us.”
I had thought that might be where she was going. “Sure,” I said calmly, though my heart was pounding hard. I pulled my penis out completely, tugging my shorts and boxers down my legs a bit so as not to be encumbered. I wrapped my fingers around my cock and started to tug. I thought I might be able to get away with some stimulation, so with my left hand, I reached down to Christine’s skirt and lifted the hem. She responded exactly as I hoped, opening her legs and pulling back her skirt, showing me her magnificent pussy in all its glory. She was mostly shaved with a tasteful landing strip above her tight, juicy lips. Christine put her fingers to her pussy and pulled her labia back, showing me her clit and her inner folds. While I stared at her pussy, my free hand found its way to Ava’s tits, which she happily let me fondle. I ran my fingers over her large, soft mounds and pinched her nipples lightly. Christine was touching herself, and Ava’s hands made their way to my cock, cupping my balls and holding the base of my shaft while I stroked myself.
Now raging hard, my cock was long enough for Ava’s hand to wrap around my shaft while I still had a bit of room at the top. I pulled my hand away, and she gently stroked me. Christine must have found this arousing because she kept touching herself even though she didn’t need to get me hard anymore. I ventured my fingers down to her slit, and she made room for me. I rubbed her clit, feeling her juices against my fingertips, while Ava gently ran one hand up and down my length and the other kept squeezing my balls.
I’m not sure how far we would have gone with this, but at that moment, I noticed someone toward the middle of the plane walking back toward the bathroom. “Hold up, guys,” I said. “Someone’s coming.” I quickly tucked myself away, though it was really uncomfortable to zip up my hard cock. Christine crossed her legs, and Ava recomposed her bosom. We sat silently as a dude walked by, clearly checking out these two hot girls on his way to the lavatory.
“Okay, that was fun,” I said, trying to cut through our newfound silence. They both laughed nervously, and I could tell that they had enjoyed it too. “So now I get two double-dares in a row, huh?”
“Uh oh,” Ava said.
“Uh oh,” Christine agreed. Both were grinning.
The toilet flushed, the dude left, and I pressed forward. “I double-dare you to switch clothes.”
This clearly caught them by surprise. I smiled as I watched them size each other up. Christine would be wearing Ava’s camisole, which was probably too large for her, as well as her leggings. And Ava would cover her tits with Christine’s too-small t-shirt and reveal her legs in her pleated skirt. I was looking forward to getting to see each girl’s other set of assets, and they had **** but to comply.
“Yes, sir,” Christine said.
“Whatever you say, sir,” Ava replied. This little display of submission really got to me, and I started to wonder where it might lead.
Christine got out of her seat, and Ava crawled past me. They both slid into the lavatory, leaving me on my own. My hard-on calmed and I took several deep breaths. After a few minutes, I was delighted to see the girls return.
Ava’s long, pale legs were creamy and smooth under Christine’s skirt, which was even shorter on her than on her half-Asian friend. The skirt barely covered her ass, which I hungrily stared at as she approached our seats. Her chest, too, was almost hilariously on display as her giant boobs strained against the shirt was one or two sizes too small. I gaped at her legs as she crawled in front of me, not quite glimpsing her pussy but knowing it was very, very close to the air.
As Christine sat next to me, I got a nice look at her, too. The camisole was, indeed, too large for her, and her B-size tits were easy to see when looking down a blouse built for D-cups. It’s not that her nipples were just flailing about, but they were easily on display when she turned at just the right angle.
“Like what you see?” Christine asked.
“Yes,” I said, “Yes I do. You are both very sexy.”
“Thanks, Teach,” Ava said.
“I’m impressed you were able to maneuver in that bathroom.”
“It’s pretty tight,” Christine said. “But big enough for two.”
The pilot came over the speaker, announcing that we’d start our descent in about fifteen minutes. I knew that the time had come—now or never.
“Okay, girls, I’ve got one last double-dare for you.”
“What's your assignment, Mr. Clark?” Christine asked playfully.
“Here’s the deal,” I said. “I really liked Ava’s o-face again, so I’m going to give it to her again.” The girls looked a little shocked and a little thrilled. “And then Chris is going to blow me in the bathroom.”
The girls locked surprised eyes with one another, but I plowed ahead, not waiting for them to respond. I used both hands to gently pull Ava’s knees apart, and she offered no resistance at all. I licked my fingers and placed them between her legs, lifting up her skirt to see her pussy. She had dark fuzz over her lips, not a wild bush but not totally smooth either. As my fingers slid between her slit, I could tell that she was absolutely sopping wet. I leaned over to her neck, licked under her ear, and whispered, “Let Teacher show you how it’s done.”
She softly whispered back, “Yes, sir.”
I rubbed her clit with one hand, pinching her nipples with the other. Occasionally, I dove deep into her pussy with one finger, two fingers, once even three fingers, giving attention to her clit from one side, both sides, the other side, directly on top… She was writhing, pinching her own nipples when I wasn’t, and biting her lower lip to keep from moaning out loud. I was very confident I could make her cum, but even I was surprised at how quickly she orgasmed. She clamped her legs together, trapping my hand between her thighs and squeezed her eyes shut. She bit hard on her lip, grabbing my arm with her free hand as she writhed about in her seat.
After several seconds, she released her grip on my hands, allowing her breathing to come more steadily, and she opened her eyes. She looked first at me and then at Christine, and she immediately started laughing.
“Bitch!” she said, and as I turned, I saw that Christine was putting away her phone. Clearly she had been filming the whole thing.
“What?” Christine asked, feigning innocence. “Mr. Clark said he wanted an o-face, and I was just trying to help.” I secretly wondered how many times Christine was going to get herself off to that footage. But for now, we had a different job.
“Okay, daredevil,” I said to Christine. “Come with me.” Ava waved a happy farewell as I led Christine by the hand into the small lavatory. I closed the toilet seat and sat her down on it. I pulled down my shorts and lifted one leg out so I could straddle her legs with my own. In this position, I could easily see her loosely-clad tits, and my cock was perfectly positioned in front of her face. “Now you pay me back for that A I earned you.”
“Yes, sir,” Christine said again and opened her mouth right up. I grabbed the back of her head and guided her to my rock-hard cock. She held my balls in one hand, the base of my shaft in the other, and dipped her head back and forth, causing the most delightful wet sensation on the tip of my cock. She started slow at first and sped up, squeezing my balls at just the right moments to distract me from unloading deep into her throat. Almost as if she could sense my feelings, Christine would pull back, take me out of her mouth, and lick my shaft right when I was about to cum, giving me a few seconds to calm down before diving back in. My hand gripped her hair and I knew I was getting close.
Not wanting to be teased anymore, I held her head firmly. I thrust into her mouth, her hands stroking my shaft and gurgles of saliva spilling down her face. The pressure built, I pushed deep into her mouth, and the most glorious rush of cum came spurting out of my cock. I held her steady, pumping load after load into her little mouth and watching it dribble down her chin and onto her small exposed tits.
I gave a few more thrusts into her mouth as the sensation of the most magnificent blowjob of my life subsided, and finally I released her from my cock. She smiled at me, cum all over her chin and face. She licked her lips and swallowed what was in her mouth, scooping the rest from her face with her hands and reaching into her shirt to rub my seed over her tits. Holy shit was she dirty!
We pulled ourselves together and made our way wordlessly back to our seats. Ava was idly playing with her own pussy as we sat back down. “Did you have fun?” she asked. We both just grinned.
The seatbelt sign came on, and our funny business had to come to an end. We kept talking of course, and though we were a bit less horny, I still pried enough to find out about a few of their more salacious stories and unfulfilled desires.
When we parted ways in the airport, my mind was reeling with the events of the flight of a lifetime. As I pulled my rollerboard to the rental cars, I got a text message. It was a reply to a group-text Christine had cued up on the plane when she took my phone. Apparently, she had texted “Hello from mr clark” to both girls, and now Christine had replied with a picture of her pussy. The message read “One of us still didn’t cum.” And then a reply from the other number: “Jillian’s gonna love you.” A moment later, an address popped onto the screen.
And that’s the beginning of the story of the best AP test grading session of my life.
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Updated on May 14, 2025
by Zeebop
Created on Mar 31, 2025
by Spindizzy
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