Truth and Dare

“Hey John. Where have you been. We’ve been looking all over for you.” John found the girls on the landing overlooking one of the hallways.

“Sorry. I just went out for some air while you were doing your thing” John lied. He didn’t care to admit that he snuck into the competition then went off to hook up with the host’s girlfriend afterwards.

His tryst had felt a little awkward at first, but as he felt himself beginning to relax, he soon found he greatly enjoyed talking dirty. He still felt a little embarrassed at how overboard he’d gone in his enthusiasm. ‘Claire, you thirsty cumslut. you want to swallow my cock like a filthy whore, don’t you? You want to feel my jizz running down your throat.’ His own words still rolled around his head as he met his sister’s eyes.

By this point in the night, each of them had drank well into their cups. The girls were all a lot gigglier, especially Riley who seemed the most lightweight of the girls. He felt a lot more confident around them now the buzz had settled in. He started to consider his chances of getting laid. That was why Claire brought him after all, though she probably hadn’t intended it to be with her friends.

“What’s that you’ve got there?” The girls interrupted his thoughts.

“Oh, Nick gave me this for you Claire.” He held the heavy bag out in front of him. “He said you got second place in the contest.”

“Second?” For a second Claire looked dismayed, but quickly smiled and accepted her prize.

“You were robbed babe. Ain’t no one got more talented lips than those” Jody giggled. John had the feeling whoever he’d paired with must have come first. He still felt a strange pride that his sister did so well regardless and wrapped his free arm around her shoulder.

“What’ya get?” Riley asked. Her voice was already starting to slur a little. She stumbled slightly as she moved to gather round.

Claire dropped the bag to the ground and untied the ribbon. Inside were a collection of small bottles of gin, vodka, wines, various liqueurs and one large bottle of champagne. “This is all good stuff. Gawd, how much did Nick pay for this.” Claire offered out her spoils to share among the group. “No way we’re getting through all this tonight.”

“Not with that attitude. Hey, look at this.” Jody was holding a pink tee she had pulled from the bottom of the bag. “Looks like it suits you.” The words ‘pro cocksucker’ were emblazoned on the front, while the back held the words 'Ask me about my head game'. “Looks like your outfit for our next night out is sorted.” Jody ribbed her. Claire playfully snatched it away and tucked it into her purse with a smirk.

“Alright, so what now?”

“I’m done playing their games. Let’s do something together.” The other girls agreed.

“Truth and Dare?” Beth offered.

“That could be fun.” Jody eyed John as she agreed. John thought Claire might object to him playing a game like that with them but she didn't step in.

“We playing by Riley’s rules?”

"Of course."

“Wait, Riley’s rules?” He looked to the girl to explain.

“So, you know Truth or Dare right?” John nodded. “Well at my college, we play Truth and Dare. When its your turn, you ask everyone else for a truth and then you dare someone too”.

“And the dare can include someone else. So really, you’re daring two people,” Beth amended, “and a dare can be vetoed if half the group agree but otherwise you can’t skip a dare.”

“Is that okay with you John?” Claire asked.

John considered it. There was no telling what the girls would put him up to. It was sure to get embarrassing but what sort of man would he be if he turned down truth or dare with such hot girls.

“Alright. Count me in.”

“Then let’s go already.” Jody grabbed John by the shoulder and pulled him aside into a guest room. The other girls followed and locked the door behind them. They dropped down in a circle with their stash of drinks in the middle. Jody sat between John and his sister to his left while Riley and Beth sat to his right.

“Alright John. You’re the guest so you go first. Then we’ll go from your left”

“Me?” He wasn’t expecting to be the first one up. He was hoping to get a measure for how the game would play out before he had to come up with anything. “What should I say?”

“It’s your turn. You decide.”

John felt the pressure rising as the girls watched him. He wasn’t sure whether they were expecting him to start out slow or jump straight into it. He didn’t want to seem boring, but he also didn’t want to push them into something embarrassing right away. Was it okay to ask something sexual? He struggled for something to say. He’d been so excited to play with the girls he was finding it difficult to think straight. His eyes danced over the women in front of him.

“Um, How about… what size are your boobs?” he blurted the only thing he could think of as he took in their collective curves. He was confident that set a moderate tone at least.

“Pfft.” He was immediately disheartened by Jody’s reaction. “Is that all boys think about?” John noticed Claire and Beth also quietly giggling to themselves. Even Riley supressed a smile as she politely averted her gaze.

“Well?” John demanded, eager to move on from their mockery.

Jody stopped laughing at turned towards him. “34DD and proud” she gave her breasts a squeeze with a teasing smile, leaning forward to give him a view of her cleavage. John fell for the bait and his eyes fell deep into her cleavage. Happy with the reaction it received, she turned to her friend. “Claire?”

It occurred to John that any question he asked would also have to be answered by his sister, a fact that seemed to greatly amuse Jody. Despite loosening up, Claire still seemed a little embarrassed to share such intimate information with John. He already knew the answer, but he couldn’t admit to that. He gave her an encouraging smile. She looked away as she mumbled “34H.”

“36DD” Beth quickly followed up to spare Claire from further embarrassment.

“34G” John’s head snapped round at Riley’s answer. He hadn’t realised Claire’s friend almost matched her in that respect. Looking at them now it was quite obvious how much they filled out her top. He dumbly drank in her figure until a throat clearing made him realise his staring. Riley blushed at the attention.

“Looks like he’s found his favourite.” Beth teased them. Riley crossed her arms over her chest but that only made their size more apparent with how little she covered.

“Time for your dare darling.”

John snapped back into what focus he could manage. He didn’t want to be patronised by the girls the whole game. He didn’t want to push too far yet, but he had to show them he wasn’t a naïve kid. “Alright, I dare Beth to… give me her panties. Without leaving the room.”

“Ooh, John’s going straight in.” John was glad he at least mildly impressed Jody this time. Beth however was unperturbed by his dare. He expected her to use the bed for cover but she just got straight up, stepped back and turned around as she pulled her shorts down. He could only stare at her bared ass as she cleanly bent and peeled her panties down her leg. In barely a moment she was pulled her shorts back over her hips and handing John the dainty piece of blue fabric. John had underestimated how experienced these girls were in their college games. With how smooth that motion was, he wouldn’t have been surprised if she’d received that exact dare before. Once again, he felt out of his depth as the girls laughed at the dumbstruck look on his face.

“My turn.” Jody spared him from the moment. She cast a devilish side glance between him and his sister before saying. “My question is, from one to ten, how attractive do you think John is?” Again, all the eyes turned towards John, this time in appraisal of him. He felt their gazes boring into him. This felt more uncomfortable to him than his own round. “Clair?”

His sister struggled to come up with an answer, perhaps to spare his feelings. It took some time for her to speak. “I mean, he’s objectively good looking. I’d say an eight.” John blushed to receive his sister’s compliment.

“Objectively is it? Alright then, Beth?”

“Seven.”

“Eight and a half” Riley offered.

John raised his brows. He turned to hear Jody’s answer before realising she didn’t have to answer her own question, and it was in fact he who had to appraise himself. “Uh, I guess I’m a seven.” He didn’t want to rate himself too highly. He was surprised the girls found him so attractive, but it made him feel better about himself. He was starting to feel a little more comfortable around them.

***

“Time for my dare. This one for John and Claire. I dare Claire to let me take a topless photo, using John’s hands as a bra.” Claire had a feeling something like this was coming. Jody had been far too eager to play this game. She should have known before they started that she was playing into her friend’s **** fetish.

All the girls knew about it. It had all come out years ago on a sleep over. Jodie’s parents had been away, and they’d procured a couple of bottles of hard drink. What had started as a simple movie night had somehow ended up with them on porn sites, sharing what they each got off to. Claire vividly remembered putting on a bukkake video with an outrageously busty woman and telling her friends she wanted ‘men to cream on her tits just like that’. That memory had made her cringe the next morning but the girls all met up again later that week and owned up to what they had admitted to and the whole incident ended up bringing them all closer together.

On that night, Jody had admitted she liked the idea of intimacy between family members. She resented the idea of doing it herself but loved stories about it from other families. The revelation had made Claire think back on all the times she had confided in her best friend, about the times her brother had perved on her or the odd thoughts she had about him. All those times she had been stoking a fire in her friend without realising. Maybe Claire’s stories had been what sparked that interest in Jody to begin with. It took a while before could accept that part of her friend and confide in her again like that.

“Shoulda known why you were so eager to play.”

“You know me Claire. It’s not a dare if it’s not interesting. You quitting already?”

Jody knew Claire better than anyone. She knew exactly how to tease Claire and push her buttons and would take full advantage of her competitive nature. She was always pushing Claire outside her comfort zone, usually for the better. That’s what made her so endearing to Claire. She loved the challenge. She loved how Jody expanded her horizons. She loved and hated that she could never say no to her best friend. Jody already knew she wouldn’t turn her challenge down. Claire downed her cup.

“John, get behind me.” Her brother’s eyes widened, clearly not expecting her to accept. He scrambled on his knees to move around her back. Claire took a deep breath, allowing the drink to wash over her mind. He’d forget this come the morning anyway. At least she didn’t have to let him see her naked. She pulled up her blouse with one hand, not intending to take it off, then went to unclasp her bra with the other.

“Why don’t you get that for her John.” She stopped. They always considered it fair game for the girls to direct their dares to keep each other from half-arsing it. Reluctantly she pulled her hand away, allowing John to fumble with the catch. She was glad she couldn’t see his face. She didn’t want to chance seeing him leer at her.

It took him a few tries before her breasts could finally fall free from their restraint. She sat and tried to psyche herself for what she was letting happen, waiting for John to compose himself. Slowly, he wrapped his arms around her, and shakily placed his hands over her breasts. His hands were colder than she expected, and she was dismayed to feel her nipple react. He started to blindly slide his hands around, seeking out their position. It took all of Claire’s focus not to respond to the pleasure brought on by the contact. She silently cursed her brother’s lack of knowledge on female anatomy. It occurred to her that hers might have been the first boobs her brother had ever touched and that made her feel uneasy. After what felt like minutes, he finally found their place and she felt her engorged nipples poke into his palms. Throughout it all she kept her eyes on Jody, not giving her the pleasure of a visible response.

“You call that a bra John? Give those girls some support.” John remained still, not wanting to upset his sister. Claire gave him a shallow nod of approval. He lifted his hands and firmly pressed her boobs against her chest. Her sensitive bosom continued to betray her, filling her with a pleasant warmth as he handled them. The sensation overwhelmed her, and her lips curled up involuntarily. It was just that moment she heard the camera snap, catching her mid-gasp. Jody had caught her out. Before she got chance to take another shot, Claire pulled her brother’s arms away and redressed herself.

“You better not show that to anyone” she said, though she knew Jody would never do that. She didn’t even want to look at the picture, not wanting to burn it into her retinas. Once she got her blouse back on she allowed John to take his place back in the circle.

“That’s a shame. It’s a good picture.”

“Alright, my turn then” Claire said. She couldn’t target her friend the same way she had been. Jody knew about all of Jody’s embarrassing memories and insecurities and just what was appropriate to hit her with at any given time. Jody on the other hand was such an easy-going girl that nothing fazed her. She laughed off her most embarrassing moments like it was nothing. There were only a handful of times when Claire had seen her genuinely uncomfortable, and none of those times were ones Claire would share with anyone. Claire had just come to accept that their friendly banter was incredibly one-sided. Instead, she’d use her questions to let her brother know her friends a little better. “How many guys have you had sex with?”

“Hm, six or seven I think” Beth said.

Beth had been in a few different relationships and unlike Claire, had no reservations about intercourse with them. She didn’t often sleep around with those she wasn’t committed with, but she still had the occasional one-night stands. Beth and Jody had taken Claire out several times in high school to find hook ups. The girls insisted Claire was overblowing her first time and should just get it over with, but Claire had always found other ways to satisfy the guys she ended up leaving with. She always had this feeling that her first time would be with someone special.

“Just one” said Riley.

Riley had only been in one relationship. Claire had first bonded with the girl over the shared struggles their early blooming had brought them. While over the years Claire had come to enjoy the attention she received, Riley had only become more self-conscious with age, believing guys were only interested in her for her breasts. She had almost only entered a relationship out of a feeling of obligation, after finding a boy she thought saw her more like a person. It had taken months for her to even let him see her bare chest, let alone touch them. They broke off the relationship some time before they left for college. Clair had been working with Riley to overcome her body shame. The fact she hadn’t shrivelled under John’s blatant attention made her glad some of it had rubbed off.

“Um, none.” The others laughed at John’s dismissive tone. Claire had specifically said guys for his sake, so he didn’t have to feel uncomfortable admitting he didn’t get that far with his one partner.

“Hm, maybe thirty if I had to guess.” Jody out of everyone had a very casual attitude towards sex. She giggled as John’s jaw dropped at her answer.

“Since you love teasing my brother so much Jody, how about I dare you to make out with Beth for one minute.”

“Now we’re talking. I’ve been wanting to do that all night” Jody joked as she crossed the circle without reservation. The two girls stared each other down as Beth accepted her advance. Claire knew neither girl would have a problem with the dare. She just wanted them to put on a show to distract John from thinking about what they just did. Seeing the boy’s eyes glued to her friends made her confident she’d succeeded. Without a moment of hesitation, the friends pulled each other in and locked lips. Their hands moved along each other’s bodies to play with their hair and curves.

Claire knew they were just getting a rise from her brother. To his eye, this probably looked like a passionate embrace between lovers, but there was no real passion involved. The girls had shared enough kisses over their adventures that they had long since dropped their squeamish attitude towards it. Making out with another girl was pretty much a right of passage for any college girl. It barely even constituted a dare at this point.

It was well past the minute when the girls finally pulled away from each other. They had put on a good show. Even Claire had enjoyed it a little. John was probably convinced that her friends were bisexual. Beth dropped back into the circle like nothing had even happened. Jody gave John a wink as she sat back down.

***

Beth’s turn was next. “My question is who is the hottest girl in the room?”

“Claire” Riley responded without a thought. Claire smiled and thanked Riley for the compliment.

John gulped. He looked around at each of the girls in the ring. He met his sister’s eyes as he quickly passed over her. Claire was hot, but he thought they might take it the wrong way if he said her. He felt a little trapped, not wanting to offend any of the girls. Finally, his eyes turned to Riley, drifting slowly over her curvy body as he considered. Riley seemed the most self-conscious of the group and could stand to gain a little ego boost. Plus, she was genuinely hot with a sexy body.

“Riley” The girl blushed at his declaration. She seemed genuinely touched by it. The round concluded as Claire and Jody responded with each other.

“Well as long as you two are digging on each other, how about we heat things up. I dare John and Riley to strip naked.”

“M-me?” John asked. He reckoned it was bound to happen at some point, but he wasn’t ready for it so soon. He’d hoped he wouldn’t be the first at least. Riley was paralyzed, glaring at her friend. Despite how relaxed she had seemed to become, the girl suddenly tensed up again from her friend’s command. As apprehensive as he was, he could see the dare was a bigger deal to the girl. “It’s alright. I’ll go first.” He tried to reassure her. This was his chance to step up and show he was mature enough to be playing this game with them.

John climbed to his feet. He suddenly felt self-conscious as all eyes but his sisters turned to him. It was impossible to hide the tent in his pants but that was the least of his concerns right now. Perhaps the girls were expecting some kind of show from him, but he’d just end up looking dumb if he tried a strip tease. He tried to ignore his surroundings, imagining he was getting undressed for a shower. Once he started pulling off his clothes, the rest of it seemed to go by so fast. It was only upon a wolf whistle from Jody he realised he was standing completely naked, his cock standing at attention for the girls unobstructed viewing.

“Nice dick. I bet you’re proud of that.”

“Um, yeah thanks.” He blushed. The only compliment he’d ever received about his manhood had come from his own mom, but somehow this felt even more awkward. The girls were staring so openly at it; Jody out of admiration, Beth out of curiosity and even Riley out of some indiscernible interest. Clearly the girl's inhibitions were starting to falter. Only Claire was understandably attempting to avert her gaze. He sat back down, and it stuck out from his lap. There was no chance of it softening any time soon. He fought the building desire to touch himself and tried to move the game along. “Your turn Riley.”

With the boy’s attention turned back to her, Riley started to squirm uncomfortably now. His act had not seemed to comfort her but only seemed to build further pressure. For some reason, the girl was incredibly uncomfortable with the dare. He wondered if she had some weird body complex, or maybe she was just incredibly prude. John hoped it wasn’t something he’d done. “Come on Riley. We don’t have all night” Beth pressed her. The other girls didn’t seem to mind her discomfort. John supposed it was part and parcel of Truth or Dare.

Riley clenched her eyes shut. Her expression was somehow serene. Perhaps she too was trying to imagine herself away from here. Slowly her body began to move as though being guided along. Her hands gripped the hem of her blouse and rose as though pulled upwards by strings. Slowly the fabric rose clinging to her chest. Finally, as she started to lift it over her shoulders, her hands stopped. The veneer started to crumble as her face scrunched up in discomfort. The internal conflict however was short lived as the fabric lost its grip, allowing her heaving bosom to fall out, bouncing into their natural position.

John was instantly entranced by the incredible globes. They were by the far the largest he’d seen in person outside his own family. For once he had no guilt to feel over his fascination. His cock twitched as he took in every detail of their curvature. He heard someone giggle, but he was too lost in them to care. He barely noticed when Riley resumed her stripping. It was only when he felt a knock to the head that he zoned back in. “Behave yourself.” Claire whispered in his left ear. It seemed there was still some limit to how much Claire would let him perv on her friends, at least for now. Looking at the way they worked through the drinks scattered before them it seemed all their limits would start to dwindle away as the game went on.

At that moment Riley seemed to come out from her trance as she opened her eyes, now completely nude just to John’s right. She burned bright red as she turned her head to him. From his vantage point he could see her entire body in detail, but he **** himself to meet her eye. “It’s okay.” He returned a reassuring smile. “You’re really pretty” he said, thinking it might help. He thought he saw her eyes soften for a moment before her gaze dropped to his erection and she quickly turned away. She crossed her arms across her chest, but this had the effect of pushing her boobs up. John took the chance to admire the rest of her body. While the girl’s jugs certainly stole the show, she also had a nice round ass to pair with it. Her pussy was shaved completely as he expected. John couldn’t find a single flaw in the girl’s body, which made it all the more perplexing to him that she was so shy to show it off.

“I dare Beth to throw all her clothes out the window.”

There was a hint of spite in Riley’s voice as she rushed straight into a counter-dare. Beth didn’t seem fazed by her friend’s anger and immediately rose to her feet to comply. Her stripping was efficient. John barely had time to appreciate the show as her clothes dropped to the ground one after the other. Though her boobs were smaller than John liked, he could hardly admonish the chance to see the hot girl naked. Beth was more confident in her skin, so he didn’t have to feel bad ogling her. A patch of hair filled the space between her legs, in sharp contrast to her friend. Her most attractive feature was the confident poise with which she moved her body.

Beth scooped up her clothes in one arm and strode over to the window. She gave Riley a confident smile as she held the pile of clothes out into the open air. A moment later they were gone, falling into the back yard below. No doubt they would be found by the partygoers below. It was unclear she would even get them back that night, and certainly not without withstanding some humiliation.

“Whoops. Think yours got mixed in too Riley.”

Sure enough, Riley’s discarded clothes were no longer to be seen. Riley glared at her friend but said nothing.

“Riley, your question?” Claire asked.

It was clear Riley was too flustered to come up with anything. “I skip.”

“Alright. New round. Down your drinks.”

John tipped back his cup. It was getting harder to keep going. He was really going to have to pace himself for the rest of the night. He suddenly realized that he needed the bathroom. He excused himself and passed through into the adjoining en suite.