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.
"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?"
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?"
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?"
"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.
"Are you going to answer my question?" she said to break the silence.
"Fine. I'm pretty vanilla, I guess. I just fantasize about different sexy scenarios with girls I like."
Blair looked like she wanted to press him further, but knew she would have to wait her turn, or else lose even more.
"Truth or dare?" Justin asked.
"Truth for me, too."
"Fine." There was so much he wanted to know about his best friend. "How many times a week do you masturbate?"
Blair's face reddened slightly, but she knew it was only fair. "Three or four, but just at night. Girls are aloud to have fun, too!"
"I never said you weren't. It's good to know that I'm not alone." The two teenagers laughed.
"Wanna keep going?" Blair asked.
"Sure. I'm learning more about you than I have in years."
"Well then," she said with a confidence. "Truth or there?"
Blair paused, looking unsure that this is the question she wanted to answer. "Am I one of the girls you fantasize about?"
Justin knew it was coming. If he chose not to answer, he would have to take off his shorts and then be down to his Calvins, which did a poor job of hiding his rock hard boner. He knew he had no choice but to finally admit to his best friend of eighteen years that he had at least some feelings for her. "Yeah," was his short reply.
Blair smiled. "Good."
Good? She must like me, too. "Truth or dare?"
Justin decided to change the subject, slightly. "What part of having sex are looking forward to the most?"
"Hmm, that's a good question." Blair looked pleased. "At the risk of you thinking I'm a nympho, I think I'm just looking forward to a boy paying that level of attention to my body. You know, like worshiping my breasts, giving me oral, working hard to please me. That's what I want."
Justin was enthralled, wanting so badly to be that boy.
"Truth or dare?"
"I'll take another truth," answered Justin.
"What's your favorite fantasy about me?"
Which one do I choose? There are so many. He decided to tantalize her, assuming that's what she wanted. "I think my favorite involves us taking your dad's boat out and dropping the anchor while the sun sets. One thing leads to another, we fool around, spend a lot of time, uh, pleasing each other's bodies, and we end up having sex under the stars."
Blair look enamored. What Justin thought was a wet spot before definitely was now. "Sounds romantic," she finally responded.
Hell yeah! "Truth or dare?"
"Hmm, dare!" Blair said.
I can't believe she wants another dare. "All right. Well I'm a little thirsty. How about you go to the drink machine beside the elevator and get me a Coke. But you can't put anything else on."
"Seriously? You want me to walk down the hall in my underwear? What about the security cameras? What if Mr. Jenkins decides to come check in on us?"
"As you said, it's no different than wearing a bikini. And I'm pretty sure that with the mixer going on downstairs, the security guards have their hands full. And Mr. Jenkins? He's too drunk by now to find the elevator!" Justin pleaded.
"OK fine. But YOU'RE giving me the money for the Coke!" Blair said standing. Justin went through the door of his room and came back with two dollars from his wallet. His lingerie-clad best friend was standing beside the main door. "You'll stand here with the door open to make sure I'm safe?" Blair asked.
"Of course I will." As much as Justin was excited about sending Blair down the hall in her lingerie, he had always felt like her protector.
Blair looked out the peephole to make sure no one was out there. "OK, I'm ready." Justin opened the door for her and stepped out in hall. After seeing that the coast was clear, he nodded to Blair and she stepped out into the hallway, hurrying past him and toward the drink machine. Justin had not yet seen her ass in her underwear, and was amazed by how much cheek was exposed. This is definitely more skin than I have ever seen from her, way more than her bikinis. Justin took the opportunity to lightly rub his hard cock through his shorts, just twice, admiring her tight, smooth ass. Blair disappeared into an alcove, but emerged just twenty seconds later with a coke. Walking back to the room, she opened the can and drank from it. Returning to the room's door, she put the can in Justin's hand. "Here's your coke!"
"It's half empty!" Justin said; he couldn't help but smile.
Back in their spots, Blair asked him, "Truth or dare?"
"Well, it's only fair. I'll take a dare, too."
"Good, you better," said Blair. "You have to give me a REALLY sexy lap dance, for five whole minutes."
"Oh my God! You have to be kidding!" exclaimed Justin. "Isn't that more of a girl thing to do?"
"Ever heard of male strippers?" Blair asked, raising an eyebrow.
"OK, fine." The two got up from their spots, and Blair sat down in the chair, finding some techno music on her phone. Justin couldn't believe he was about to give Blair a lap dance. "You better not ever breathe a word of this to anyone," he demanded, as he got into position in front of her.
"Oh don't worry," came the reply, followed by Blair pressing the play button on the music. "Go!" Justin nervously began gyrating his hips in front of Blair, eventually bending over to hold onto the bed. Blair began cooing and intermittently shouting, "Oh baby!" Feeling like he was being mocked, Justin turned up the intensity, backing his ass into her knees. Blair instinctively parted her legs, inviting Justin to back closer to her body. While retaining his masculinity, Justin mimicked the stereotypical male strippers in his movements, to Blair's laughter and delight. He turned around and started dancing in fake seduction as her catcalls increased. Justin brought his right foot up to the chair's arm rest, placing his crotch just inches away from her face; he looked down to see Blair staring with wonder at his obvious bulge. He turned back around and started shaking his butt closer to Blair's torso. Tucking his thumbs suggestively into his shorts, he began pulling them down just a few inches, revealing his black Calvins. After Blairs calls to "Take them off!" Justin finally stopped the tease and obliged, letting his shorts drop to the floor and kicking them to the side. He felt Blair's body inch closer to the edge of the seat, her legs spreading even more. Justin backed further into her, feeling the heat of her pussy through their layers of undergarments. He looked to the clock on the night stand and realized that the five minutes were up. He stopped his gyrations, turned around and pulled Blair up off of the chair. As he turned toward his short, Blair said, "Leave them off. That way I don't feel quite as exposed."
"OK, sure." Justin thought. It's pretty clear that I'm rock hard. She must be OK with that. Maybe she likes it... He decided not to try to hide it.
"Truth or dare?" asked Justin as he sat back down in his seat.
"Truth this time," Blair said with renewed enthusiasm.
"Do you ever think about having sex with me?" There was a tinge of nervousness to his voice. He knew the answer, but he was so afraid he would be wrong.
Blair nodded her head. "Yeah. Honestly, any time I have ever really imagined it, it was with you."
Justin couldn't believe his ears. He was expecting a Yeah, sometimes or maybe a coy maybe. But to think of him exclusively? Fuck...
"My turn. Truth or dare?"
Justin answered, "Well, I don't want to degrade myself anymore, so I'll just take a truth."
Blair giggled at his answer. "OK, fine. Then let me think of a good one... Oh, yeah. You said your favorite fantasy involved me and my dad's boat. You said we would make out,..."
"I believe my exact words were 'fool around,'" Justin corrected her.
Blair rolled her eyes. "Fine - we...'fool around'" she said with air quotes, "then please each other's bodies, and then have sex. I'm just curious how you fantasize about 'pleasing my body'" - again, with air quotes.
Justin found himself eager to answer. "Well, you said earlier that you liked your breasts being played with. Which is good, because in my head I always start there!"
Blair repositioned her legs underneath her.
"Then after spending a long time massaging your breasts and playing with your nipples, I'll eventually work my way down to your, uh..." he trailed off. He had never talked specifically about Blair's nether region.
"You mean my pussy," assisted Blair with sexy confidence.
"Yeah. Then I work my way down to your, your pussy." Saying it to her out loud made Justin feel so naughty, like their relationship had just entered a new level.
"And what specifically do you do to my pussy?" asked Blair.
"Well, first..." he paused. His eyes opened wide and his nostrils flared. She's done it! "You just asked a second question!"
Rather than feign frustration as she had done before, Blair remained calm. After a beat, she looked at him with that same sexy confidence and said, "If you want my bra off, then you have to take it off."
Justin almost fell out of his chair. After eighteen long years, he was about to unclasp his first bra.
"Well?" Blair asked.
On that cue, Justin rose from his seat and sat down in front of Blair on the bed. He allowed himself a moment to take in the sight of his best friend in her revealing lingerie, then moved closer to her as he reached both hands around to either side of her back. Keeping eye contact Justin found the clasp and fidgeted for about ten seconds. Blair smiled and let out quiet laughter, their faces only inches away. Finally, Justin was able to move both pieces in the correct way, and the bra was unclasped. Slowly, he guided the straps of the baby blue bra down her small shoulders, causing the cups to pull away from her chest. After a brief eternity Justin had removed the bra and was admiring two perfect breasts, more beautiful than he could have imagined. So many times he had tried to picture what Blair's breasts would look like, but had never been able to envision the perfection that sat in front of him. They were small, yet full; round, yet perky. Her nipples were pink and hard, her areola small. Justin's cock began oozing pre-cum.
Blair broke the silence, "What do you think?"
Without thinking, Justin responded, "I think I'm in love."
Blair smiled, clearly pleased and confident. Justin couldn't help but stare at her boobs, and she was enjoying every moment. She allowed him more time to gaze at her nakedness, then said, "Justin, it's your turn."
Justin couldn't think of anything to ask her. His night was going perfectly, better than he ever imagined. He was on a bed with his best friend, staring at her naked breasts. Finally, he floated a soft ball - "Do you like how much I'm enjoying your breasts?"
Blair sat silent; instead of answering, she moved closer towards Justin, reached down for his right hand, and guided it to her left breast. Justin couldn't believe what was happening. Without breaking eye contact, he began fondling her breast. How can it be both soft and firm at the same time? It was unlike anything he had ever touched. He looked down to take in the sight of his best friend's boob in his hand, and noticed that her nipple looked harder. With his thumb and pointer finger he lightly and slowly rubbed her nipple for the first time. Upon hearing Blair gasp, he looked back up at her face. Her eyes were now closed and her mouth open; she was clearly enjoying this sensation. After a few more moments of ecstasy, Blair reached for Justin's left hand and placed it on her other breast. Justin alternated between gripping each breast and toying with her adorable nipples, further encouraged by her soft moans.
Through moans and still with closed eyes, Blair managed to get the words, "Truth or dare?" out. Justin kept both hands cupping her breasts.
"Truth," Justin answered.
"Are you turned on now, too?"
Justin leaned his head to the side of her euphoric face, and whispered in Blair's ear, "I dare you to find out."
With that, Blair's eyes shot open, reinvigorated. She reached toward his crotch and through his Calvins, wrapped her little right hand around his rock hard cock. He inhaled a quick rush of air. She's actually grabbing my dick. When he recovered, he returned his face to directly in front of Blair's, and the two looked deeply into each other's eyes. Two seconds later they were locked in a passionate kiss. Justin moved his arms off of Blair's breasts and pulled her in close while simultaneously guiding her towards the pillow. When they landed in position, Justin was lying on his side facing Blair, still making out with her tender lips. The kiss was messy, especially after their tongues finally met and pushed past one another. Justin returned his right hand to Blair's exposed tit; her right hand had never left the front of his trunks. Justin massaged her tender nipples while she rubbed up and down his stiff cock, his trunks becoming wetter and wetter with pre-cum, both of them moaning.
After a few minutes, Justin broke free of Blair's lips, and started kissing slowly down her neck. She leaned her head back enjoying every sensation as Justin made his way to the edge of her breast. He slowed his march downward, tantalizing her. He kissed around her right nipple, careful not to graze it just yet, then moved to her other breast for the same. Finally Justin allowed his tongue to quickly come in contact with her nipple, resulting in a sharp, "Oh" from Blair. He did the same on her other nipple, and found a similar effect. Blair took her free hand and placed it on the back of his head, pulling him closer into her. With that cue, Justin latched fully on to Blair's pert breast, alternating between gently sucking her nipple and flicking it with his tongue.
Blair's moans rose in volume, and she quickened the intensity with which she was rubbing his cock. Her arousal continually rising, she finally reached under the waistband of Justin's trunks and wrapped her hand around his bare penis. It throbbed in her hand, causing Justin to temporarily suspend his worship of her tits to emit an, "Oh fuck!" This drove Blair wild, and she skillfully pulled his Calvins below his knees. Justin instantly removed them from his legs completely, lying back down beside her completely nude for the first time, pre-cum dripping from his dick head and down his long shaft. The pause in action allowed Blair a few moments to admire Justin's manhood, and after he lay back down beside her she said, "It really is eight inches!"
"I wouldn't lie to you," Justin said before kissing her on the lips and returning to his worship of her breasts. The two were back in ecstasy, not sure if the pleasure came from what they were receiving or what they were giving. After another minute, Justin reached down with his right hand to Blair's soaked panties. He started rubbing what he could feel was the outline of her slit, to Blair's palpable delight. Tracing his pointer finger back upwards he felt her clit, confirmed by Blair sitting up slightly in the bed. He started rubbing her clit through her panties, simultaneously playing with her nipples. Blair's moans were louder, so loud that he was worried about being heard through the hotel walls.
After letting him massage her aroused clit for a few minutes, Blair turned back on her side and guided Justin's mouth from her breast to her face, and the two were once again locked in a sexy kiss while their hands were busy working each other's genitals. She didn't allow their kiss to last long, breaking it to take her turn kissing down his neck and chest. Blair kissed and flicked Justin's nipples for a moment, but continued downward toward her eight-inch goal. Finally eye-level with his massive, throbbing cock, Blair allowed herself a few moments just to admire it. "It's perfect," she said gleefully, before running her tongue up his shaft to his dripping head.
Justin's body twitched at her tease. "Oh baby," escaped his mouth. Blair smiled at being called "baby" by her lifelong best friend, and once again ran her tongue the length of his penis, slower this time. After another brief pause, she allowed her tongue to slowly circle his sensitive dick head, lapping up the salty pre-cum that was still oozing out of him. After several more orbits and Justin's increased vocalizations, Blair wrapped her lips around his swollen head, still circling with her tongue like she would a lollipop. With her right hand she felt his balls for the first time, hanging low and full of the cum he was eager to pump into her. After acclimatizing to his head, Blair took in more of Justin's length, eventually enveloping much of his larger-than-average cock. Justin's eyes were closed, his hand on the back of Blair's head as she tenderly started bobbing her head, allowing Justin's penis to go in and out of her small mouth. Oh my God, I'm getting head!, Justin kept saying in his mind.
Despite what she had heard from her female friends, Blair actually enjoyed giving Justin a blow job. She was careful not to attempt to take all of his length into her mouth, fearful that she might choke. But at the same time, she was incredibly turned on by the experience, clearly excited to be giving Justin so much pleasure. Without even thinking, she moved her free hand down to her crotch to slowly finger herself. She took a break to offer Justin some variety, licking down his shaft to his balls and taking each one into her mouth in turn, sensuously and carefully. This drove Justin wild. She went back to bobbing on his cock, bringing Justin ever closer to orgasm.
Convulsing on the bed, Justin felt the sensation growing in his dick, but he didn't want to cum so soon. Right before the point of no return, he tapped Blair's head and said, "OK, that's all I can take for now." Blair actually looked disappointed. She released his throbbing cock from her mouth and hands, and began to raise up off of his lower body. Her boobs that had been resting on Justin's thighs were suddenly visible again, and Justin needed to feel them. He grabbed Blair's shoulders and guided her upper body to his and again began kissing her passionately. Her lips and tongue were salty with the taste of his pre-cum, but he didn't care. Careful not to restimulate his aroused cock, Blair rested her tiny ass on Justin's abs, immediately placing her boobs at Justin's face level. Again in heaven, Justin instinctively placed his hands on each little tit, slowly massaging and kneading. Blair lowered her upper body down to Justin again, placing her left nipple right on Justin's lips. He instantly met her cute nipple with his tongue, flicking a few times before taking it into his mouth. Blair moaned, reaching behind Justin's head to pull herself further into his warm mouth. After a few minutes Blair raised her boob out of Justin's mouth and switched him to her other. Justin was eager to please, turned on even more by the warm juices slowly dripping out of Blair's pussy onto his smooth abs.
Finally Justin took charge, raising up off the pillow and turning Blair over on her back in one swift motion. Now suspended over her, he continued playing with her gorgeous breasts, but quickly pulled off of them to make his way southward. Kissing down her flat tummy, he made his way to her shaven sex, and kissed around it and down her right thigh. Blair was shocked by the pleasure she was receiving from Justin simply kissing up each thigh, slowly teasing her as he made his way within an inch of the opening of her drenched pussy only to pull away at the last moment to kiss down and then up her other small thigh. Finally after enough tantalizing Justin completed an ascent to land a kiss on Blair's damp slit. Her body raised off the bed in pleasure, and Justin immediately started licking around her vagina, her labia, and finally to her clitoris, while his hands returned to her pert breasts. He instantly began flicking her clit with his tongue, causing Blair to moan with intensity. After a few minutes he removed his right hand from her breast and traced down her side to her crotch. While continuing to worship her clit, Justin let his pointer finger lightly rub up and down the opening of her vagina. Through her moans, Blair said, "Put it in." Justin obliged, pushing his finger through the slit and into her tight pussy. It felt otherworldly - unbelievably smooth, wet, and fragile, yet strong. Blair's moans rose in intensity as he began to slowly fuck her with first one, then a second finger.
Justin was entranced: his mouth on his crush's clit, his left hand playing with her breast, his right hand fingering her. Blair allowed her waist to rise slightly off the bed to meet the movement of his fingers, encouraging Justin even more. Spellbound, Justin could have continued this for hours, and would have if Blair had not tapped him on the back of his head. He rose from her sex and looked at her angelic face. "Make love to me," she said. "I want your eight-inch cock inside me."
Justin smiled at her and raised away from her lower body and toward her face. The two passionately kissed again as Blair reached down, grabbed Justin's engorged cock, and guided it to her opening. Justin broke the kiss as he became aware that he was about to enter his best friend's pussy, feeling her warmth and wetness on the tip of his penis. He looked down at her small body: her heaving breasts, her erect nipples, her soft moaning lips. He looked back at her eyes, which silently said, "I'm ready." With that, he pushed his large teen cock gently into her open virgin pussy.
She was so tight, but they were both well lubed. After an eternity, Justin had pushed as much of his manhood as would fit into Blair's pussy. The initial look of discomfort had turned by now to contentment, and Justin pulled mostly out. He thrust all of his dick back into her, this time more quickly. Blair emitted a soft moan and placed a firm hand on Justin's ass cheek. Justin was encouraged, and began fucking his best friend faster and faster.
The volume of Blair's pleasure began to rise, which only made Justin thrust more deeply into her young body. The two established a beautiful rhythm, Justin fucking with intensity, Blair moving subtly in response. After a few minutes Justin began to feel more and more of his friend's juices, a clear sign that she was enjoying their lovemaking as much as he was. The sight of her beautiful face in ecstasy, the motion of her breasts bouncing with every thrust, the sexy sound of her moans, and the rhythmic clack of his big, full balls slapping her skin; nothing in the world could be better than this moment. Fucking Blair was a cardio workout, but he could have done it all night.
After a long while, Blair's moans turned louder as it became clear that she was close. Justin felt close, too, and started moaning. Blair looked up at her friend, put her hand on the back of his head, and said, "I want to feel you cum in my pussy." She had said some sexy things that night, but that was the icing on the cake. After ten more thrusts, Justin's cock began to erupt; he shot his warm cum fully into her body as the height of Blair's orgasm began. For a few long seconds, the pair's vocalizations were enough to alert the whole floor of the hotel. Calming down, Justin's cum, the largest ejaculation he had ever produced, mixed with Blair's pussy juices and oozed from her slit as he pulled his long, softening penis out of her.
Sweaty, exhausted, and both dripping from their emissions, the couple collapsed into a pile on the bed. Holding each other, all they could do was look into one another's eyes in a way they had never looked at the other before. Again they kissed, but this time it held a deeper meaning. This was the first time they fucked, but it would definitely not be the last or even the best.
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