It was finally happening. After pining for Blair basically since he hit puberty, Justin was finally going to get some alone time with her - overnight! Both freshly eighteen and seniors in high school, Blair and Justin had been friends since childhood. Their parents were close friends all of their lives, and even took vacations together every other summer. And when they were not on vacation, they spent their summer days in Blair's parents' pool, and the rest of the year snuggled on the couch watching TV. Blair and Justin had been raised as closely as two non-related kids could have been, and were lifelong best friends as a result.
The connection they shared was palpable to the rest of their friends growing up, who always teased them about being "practically married." But the two had resisted peer pressure, both having some not-so-successful relationships with other kids their age at the start of high school. Since freshman year, they had never been single at the same time. Until now.
Blair and Justin were both very smart, at or very near the top of their class, always in friendly competition. They were both well liked, by their peers and by their teachers. Both were athletic - Justin on the soccer and basketball teams, and Blair as captain of the volleyball team. They were both always present for the other's games, Justin more so he could see Blair in those skin-tight spandex volleyball shorts, even when he had a girlfriend. It was hard not to enjoy the way the tight uniform hugged her adorable 5'8 body, made angelic with her natural, long blonde hair, her flawless skin, her tight but noticeable ass, and her perfectly round b-cup breasts that he never missed an opportunity to admire in a bikini when they swam in the pool. He suspected that Blair felt the same way about him - often when he came over during the summer to swim, Blair would playfully whistle when he took off his shirt. And why not, with his lean but muscular 5'10 frame, his dark slightly messy hair, his chiseled hairless chest, and the six-pack he worked tirelessly to maintain. Plus she often asked him jokingly about his dick, curious about its length (which Justin never revealed to her).
At the start of the year, it was a tradition at West Plains High for the teachers to choose two seniors - a boy and a girl - to travel the two hours by car to Atlanta for the state Youth Leadership Weekend. It was a high honor, and represented a lot of trust in the students chosen. Justin had wished all summer that both he and his increasingly gorgeous best friend would both be chosen. Not so much for the conference itself, or even for what it would mean for his college applications; he knew that it meant two nights in adjacent hotel rooms with very limited adult supervision. On the first day of class Justin got his wish, the principal announcing the news in front of the entire school. Somehow, he managed to conceal the instant hard-on he acquired after the principal read their names...
...
A month had passed, and pretty much all Justin had thought about was spending some evening alone time with Blair, and all the possibilities that entailed. He had counted down the days, and it was now the day before. Between classes, Blair walked past him in the hall and said, "Can't wait for tomorrow!" Justin smiled at her and simply responded, "Same here." What could she mean? he analyzed the rest of the day.
That night Justin gave way more thought to what he would pack than he ever had to go anywhere. Gotta include that blue shirt that she thinks brings out my eyes. And these jeans she helped me pick out at GAP because they fit tighter against my butt. This jacket is fluffy, maybe she'll snuggle up next to me if we're outside and it's chilly. After an hour's worth of packing for a three-day, two-night trip, Justin finally lay down in bed to get whatever sleep his racing mind would allow him. He could think of nothing else than what Blair might be packing in her suitcase, and his hand slowly made his way inside his tightening basketball shorts to grip his rock-hard, 8-inch cock. It took just a few minutes of pumping to build to a huge orgasm, and he covered his bare chest in warm cum before drifting off to sleep.
The next morning he leapt out of bed, showered, shaved, and loaded his car - he had volunteered to be the driver, with the understanding that they would meet Mr. Jenkins, the "chaperone," at the hotel. Justin pulled into Blair's driveway, and watched in awe as she cutely ran to his car with her duffel bag and slung it into his back seat. Inside, she leaned over and quickly kissed him on the cheek, and said "Let's go!" The kiss was nothing new - the two best friends had often exchanged cheek kisses after sports victories or absences. But Justin couldn't help but wonder if she had been looking forward to this trip the way he was. He remembered that the idea had led him to the point of masturbation just nine hours before, and he wondered if she could have done the same thing?
The drive to Atlanta was uneventful. The two gossiped about various classmates like always, while listening to their favorite playlists. After being lifelong best friends, their musical and conversational topics were very much in sync. Upon arriving at their destination, Justin parked his car and the two went into the lobby to check in. They gave their names to the front desk receptionist, who handed them individual small envelopes with room key cards. She also told them that Mr. Jenkins had already checked in, and said he would see them at the meeting later that afternoon. Blair asked the receptionist what room he was staying in, and she replied, "820." The two friends quickly looked down to their room key envelopes - 314 and 315. They instantaneously looked at each other and smiled.
Blair and Justin rode the elevator to the third floor and then went to their respective rooms. Justin's room was nice and basic - a king bed, desk, flat-screen TV, nice bathroom, and a balcony. After a few seconds he heard a knocking, but not from the door he had just entered. He had been too busy checking out the room and view to notice the unassuming door on the wall opposite the bed. He opened the door to a grinning Blair, who said with a hint of excitement, "Adjoining rooms!" Justin was in an ever-increasing state of disbelief at how wonderful the weekend was turning out to be already.
Soon it was time to go down to the hotel's large ball room for the start of the leadership conference with about 250 other high school seniors, and the disinterested teachers who were obviously there for the weekend away. The opening session was just boring speeches and broke for dinner by 7pm, after an announcement that there would be a "mixer" at 9. Blair found Justin and asked him if he wanted to get some food at the hotel's restaurant. At dinner Justin asked Blair if she was interested in going to the mixer. He already knew the answer - both of them hated dancing and social events with people they didn't know. Blair responded with a smirk, and said, "Nah, let's just go back to the room and hang out."
Hmm, she only wants to be with me, Justin thought with a smile...
...
They didn't even bother going in their separate rooms, having left the adjoining door open. For the conference they had to wear "business attire," so the two agreed that step one must be to change into something more comfortable. Justin went into his room to change, without bothering to close the door. We're both out of sight from each other, he told himself. He took off his suit and changed into some athletic shorts and a grey t-shirt. He walked back into Blair's room, careful to knock the door noticeably in case she was still getting dressed. Blair had on some tight black shorts that she often slept in and a white camisole that showcased her beautiful, soft cleavage. Despite having seen her in a similar outfit countless times before, Justin was awestruck - she looked good!
"What do you want to do?" Blair asked him.
Recovering from his horny stupor, Justin said, "I don't know. It's Friday night, so there's nothing good on TV. I don't really wanna pay five dollars to rent a movie we've probably seen either."
"We could play a game," Blair offered. "Know any good ones?"
With a coy grin, Justin said, "I still have my Dasani from lunch - we could play Spin the Bottle!"
"Nice try," Blair said, matching his coyness.
"It was worth a shot," Justin shrugged with a wink as he sat down in the room's only chair, next to the king bed.
"When I've gone to those awful sleepovers at Mindy's house, we would always play Truth or Dare," she said sitting opposite him on the bed. "It was always the same old thing with the girls, but it might be fun with just the two of us."
This could be interesting, Justin thought. What's she trying to get out of this? "Yeah, maybe," he finally said. And then he had a flash of brilliance - "but we would have to make it... interesting," he said with flirtatious smile.
"Interesting how?"
"Well, there would need to be penalties in place. You know, for if there is a question we don't want to answer, or a dare we don't want to do."
Blair thought for a second, and finally responded, "OK, that makes some sense. But what penalties did you have in mind?"
"Well, we're kind of limited in here. We don't exactly have access to any liquor for penalty shots."
Blair laughed at the suggestion. The pair were basically good kids, never venturing into situations where alcohol was present. In fact, the only alcohol they had consumed was what their parents let them try the summer before while vacationing together at the beach. "No, I guess we'll have to think of something else."
Justin pretended like he had just gotten a great idea, although the thought had occurred to him minutes before. "Well, the penalty could be that we have to ditch an item of clothing."
"What? Are you trying to see me naked?" She asked in good humor.
"Not if you answer all my questions and take my dares."
Blair thought for another second, then said with confidence in her voice, "You know what, I'll take you up on that! We'll play Strip Truth or Dare, and just see who comes out clothed in the end!"
"Oh, you're ON," he returned.
"I'll even up the ante on you, mister. Same penalty if one of us asks a question out of turn."
Justin puzzled over the suggestion, but thought it harmless. "OK, sure."
"But we have to agree not to ask something that we wouldn't do or answer ourselves," Blair said pleadingly.
"You know I wouldn't make you do anything I wouldn't do, too," Justin said. And he meant it - the two had looked out for each other for years.
"I know, I just needed to say it before we got started," Blair responded. "Wanna flip for who asks first?"
"Yeah, I think I have a quarter in my room." Justin got up and went next door to fish a quarter out of the slacks he had been wearing prior. Bending down to get them out of his suitcase, he realized that he was sporting a semi. Concerned that Blair would notice before the game even got started, he reached into his Calvin Klein trunks and pointed his dick downward, hoping that the tight fabric would hold it in place.
"Found one," he said returning to his chair. "Call it in the air."
Justin flipped the quarter, and Blair called "Tails," as he caught it and placed it on his arm.
"Tails it is. Ask away!"
Blair grinned. "OK. Truth or dare?"
"Truth." Justin thought he would start it off easy.
Without missing a beat, Blair asked, "How big is you penis?"
"WHOA!" Just half-yelled. "Right off the bat? Damn, girl!"
"I'm waiting for your answer!" she said in a school teacher voice.
Damn, that question was locked and loaded, he thought. "OK, since you've always wanted to know, I'll finally tell you. As long as we both agree that nothing we say here leaves this room?"
"Of course."
Justin paused - he wasn't sure if it was because he was nervous, or because he wanted to tease her as long as possible. Finally, he revealed the answer, with seriousness to his tone. "It's eight inches."
"Oh my God!" said Blair instantly. "That's like, way above average."
Justin nodded, so very pleased with himself.
"Is that soft or hard?" Blair asked.
Justin's face lit up, his mouth opened. "You just asked a question out of turn!" he proclaimed, giddy as a child.
"Wait, hold on. It's an obvious follow-up!" Blair said hurriedly.
"Nope, that's a second question. You have to lose an article of clothing."
"Come on, you can't possibly..."
"It's your rule!" Justin interrupted.
They were both smiling during the course of the interchange, both knowing the inevitable outcome. "Fine!" Blair said, and reached down to pull the camisole over her head, throwing it on the bed. She was wearing a cute baby-blue bra with lace on the edges, putting the right amount of pressure on her breasts to create two perfect round globes that Justin was finding literally mouthwatering. Wow, is the only thought that came to his mind. He had seen her in bikinis many times before, so even this level of cleavage was nothing new. But to see her in her actual bra, half sitting and half lying on a bed was breathtaking. His cock was still in the pre-arranged position, but he could feel it getting much harder.
"Are you gonna answer my question, or are you gonna stare at my boobs all night?" Blair asked him.
Justin was slightly embarrassed, and managed to stammer, "Oh, uh, sorry. I've just never seen a girl in a bra in real life before."
"Justin, you've seen me in a bikini like a thousand times. This is practically the same thing."
"Yeah, I guess so. It's just new. And you look really, really good. That's all," he said nervously.
"Thanks," Blair said rolling her eyes. "So are you gonna answer my question? Is it eight inches when it's hard or when it's soft? I don't know how those things work?"
Justin thought about flirting with her for a second. It's definitely eight inches NOW. "When you ask a guy how long his dick is, he's going to give you the most impressive measurement. Meaning, when it's hard."
"OK. Now was that so difficult?" Blair asked, shaking her head.
Justin was having a hard time not staring at his beautiful best friend's cleavage. He tried to make as much eye contact as possible, allowing himself fleeting views of her bra-covered breasts as he broke his gaze to look at the door or the balcony. Then he remembered that it was his turn. "Truth or dare?"
"Truth."
Justin had not thought about what he would like to ask Blair. Then he thought back to her original question about his cock. She had often asked him that before, half jokingly. Maybe there's something more there, he thought.
"OK, I've got one. Why are you so obsessed with my dick?"
Blair's mouth fell open in disbelief. "Whoa. I was NOT expecting that!"
"You've asked me at least a dozen times in the past, and it was the first thing out of your mouth tonight, now that you've finally got me under oath. I think I have a right to know," he said with a confident smile.
Blair cut her eyes at him. "OK, fine I'll answer it, but just so I don't have to take any more clothes off. I guess I don't really know why. I'm not OBSESSED, sorry if that bursts you ego. I'm just curious. I don't have one, I've never seen one in person. And I guess since we grew up together, I just wondered how yours, umm, compared to the six-inch average. Plus, I've seen you in swim suits and sweatpants a BUNCH. Sometimes I notice that you have a pretty impressive bulge, so I just wondered, well, HOW impressive it actually was. Satisfied?"
Justin was euphoric, and even harder. She's given a lot of thought to my cock. He decided to flirt a little to break the tension. "Hmm, sounds like you just come to my basketball games for a peek of my bulge..." he said with a grin.
"NO" Blair yelled and threw a pillow at him. "Shut up!" She was visibly embarrassed.
Justin decided not to push further, and just laughed. "It's your turn."
"OK. Truth or dare?"
He wanted to do a dare, but was curious to what she would ask next. "Another truth."
"Fine. What's the furthest you've gone with a girl?" Blair asked, her voice growing more serious.
"Well, we drove two hours to Atlanta today, so I would say that the furthest!" Justin said with a devilish grin.
This made Blair giggle, a quality he adored in her. "You know what I mean!" He was happy her mood had lightened.
"Fine. To be honest, the furthest I've ever gone was making out with Joulie and Kate - at different times, obviously," he said about his two most recent, albeit short-term, girlfriends. "Joulie and I never did any, uhm, touching, but I did grab Kate's ass." Justin felt as if he had just gone to confession.
"Oh." Was all Blair said, with a slightly surprised look.
"If you were expecting more..."
Blair interrupted, "No I'm sorry. I guess I just figured that you had gone further than I had."
The thought of another guy grabbing Blair's perfect ass made Justin jealous. He had always been envious of any guy she dated, thinking them wholly unworthy of such an angel. An angel who was now sitting shirtless on a bed in front of him.
"OK then. Truth or dare?" Justin asked.
"I know what you want to ask, so truth."
"Who have you gone that far with?"
"Kyle is the only boyfriend I've ever really made out with," she responded about the boyfriend she broke up with at the start of the summer. I don't miss him AT ALL, but it was nice being touched," Blair offered. Justin looked puzzled.
"Where did he touch you?" Justin asked.
Blair's eyes and lips narrowed. "That's two questions out of turn," she said proudly. She had finally gotten him back, masterfully. And Justin knew it. He sighed, and then reached down and pulled off his white shirt, and threw it on the bed beside Blair's camisole. Blair looked pleased, and Justin couldn't tell if it was because she had played him, or if she enjoyed the sight. "Kyle grabbed my ass a few times, and I let him touch my boobs once, over the shirt. And before you ask and have to lose your pants, too, yeah. It felt really, really good."
I bet I could make them feel even better, Justin thought to himself, fighting the urge to speak it aloud.
"OK, now we're both up to speed with our romantic histories. Let's move on. Truth or dare?" Blair asked.
"I'm tired of the interrogation, so I'll take a dare," Justin answered with enthusiasm.
"Interesting," Blair said playfully. She put her hand on her chin, indicating that she had not yet given her dare requests any thought. Then she laughed. "OK, I've got one for you. You have to go out on the balcony, drop your shorts and underwear, and stand there fully exposed for an entire minute."
He couldn't believe the brashness of her dare, and just looked at her in disbelief. Finally he said, "OK, I guess that seems harmless enough. The balcony's not really lit, so anyone in the building next door is gonna have to look pretty hard to see anything." Then standing, "OK, let's go!"
Blair smiled and walked with him to the balcony door, opening it for him. When he got outside she closed it. Through the glass, she said, "I'll time you. Ready?"
Justin looked back behind him. Wow, she's actually gonna stand just two feet behind me while I'm out here naked. "Ready," he said loudly. He turned back away from her, and with one swift motion dropped his shorts and Calvin Klein trunks to the floor. All he could think was that Blair could only be staring at his bare ass. He leaned against the balcony railing, careful to keep his legs together to prevent his balls from being visible to her. The thought of his shirtless best friend admiring his ass caused his cock to rise to half mast; the chilly weather was the only thing that kept it from a full erection. Justin quickly scanned the windows in the hotel across from theirs, and seeing no one kept his hands on the railing and his penis uncovered.
After what felt like an eternity, Blair yelled, "TIME." Just bent down and pulled his shorts and underwear back up, but was forced to leave his semi-erect dick pointing sideways in his shorts. It would likely be noticeable to Blair, but he didn't care.
"That felt like way longer than sixty seconds. You were just staring at my ass the whole time," Justin said in playful accusation.
"So what?" Blair said. "Your eyes haven't left my tits since I took my shirt off!"
Justin smirked. That's all he could do because he knew she was right.
Back in their spots, Justin asked "Truth or dare?"
Blair shrugged, and answered "Dare. Why not?"
"Good. Let me think of a good one to get you back for the public indecency you just made me commit," Justin said with a wink. Then he thought of all the times he had fantasized about her sucking his cock, and got an idea. "I want you to lie on the bed, and pretend that your pointer and middle fingers are a dick that you have to suck for a whole minute."
"Damn," Blair said, mulling over the idea. Justin was more than pleased at the idea.
"What? It doesn't involve any nudity. Just some acting," Justin offered.
"My fingers are nowhere near eight inches long, though," Blair said in her flirty tone.
"I didn't say it had to be my dick. But if that's what you want to imagine, then go for it!" Justin said, winking again.
"Fine, but only because I don't want to take off my shorts." Blair immediately spun her legs onto the bed and flipped over so that her backside was facing upwards. Justin's eyes immediately darted to Blair's tight butt, covered beautifully by her small black shorts, leaving little to the imagination. Just as Justin noticed his cock start to stiffen even more, he heard Blair moan. He looked toward her face; her tongue was out, licking its way up and down her two fingers sensuously. After a few oscillations up and down the pretend shaft, she flicked her fingertips with her tongue before engulfing her fingers with her mouth. Blair's head started bobbing up and down the length of her fingers, her moans increasing. Justin couldn't believe his eyes. Obviously she's given this some thought.
Justin was mesmerized, realizing eventually that he had forgotten to look at the clock on the nightstand when she started. His hands were in his lap when she started - surely she won't notice if I rub my cock just a few times. With as little movement as possible, Justin applied pressure to his penis with his thumb; just that slight stimulation caused it to quiver with pleasure. He better not rub much more than that.
Suddenly the angel on the bed stopped her mimed oral sex and said, "That's got to be at least two minutes. Weren't you timing me?"
"Uh, actually the time just now ran out," Justin stumbled.
"Yeah sure. Hope you enjoyed that," Blair said, flipping her body back over to lie on her back. "Truth or dare?"
"Truth."
"OK. What kind of porn do you watch when you jerk off?" Blair asked abruptly.
Justin was surprised with her directness. There was no room for him to even act like he didn't masturbate. "Honestly, I don't really watch porn. My imagination is good enough," he answered confidently.
"And what do you fantasize about?"
Have I just gotten her back? Was it that easy? "You just asked a question out of turn!"
"SHIT!" shouted Blair. She sat up on the bed, shaking her head in disbelief. She stood up, tucked her thumbs into her tight shorts, and pulled them down to her ankles, kicking them off into the floor. Standing directly in front of Justin, Blair was down to her lingerie - her baby blue bra with the lace, and small matching panties with very little fabric. She returned to her half-recline on the bed. Justin couldn't help but look down and take in this new sight, transfixed on the thin fabric separating her sex from full exposure. Not wanting to stare at her for too long, his view was only fleeting. But he thought he saw the faint outline of a wet spot where her pussy would be. His cock was fully hard.