A new round begins

After John left the room Riley seemed to relax a little. With a little concern for her friend, Claire pulled her aside to one corner of the room to talk quietly. Beth and Jody began a lively discussion as they left.

“Are you okay Riley?”

“I’m fine. I just wasn’t ready to do something like that.”

Riley had always had a complex over her breasts. Claire knew more than anyone what it had been like for her growing up. It was impossible to do anything without drawing attention to them. Doing sports, bending forward, even sitting at a table would have them sitting on display on the surface in front of her. They were an ever-present facet of both of their lives that elicited endless attention from the boys. Suffice to say, they had had a very prominent impact on both girl’s teenage development.

Riley had been a quiet girl. If not for the attention her body got, she felt she wouldn’t have gotten any at all. She felt humiliated to think that boys only saw her as a walking pair of boobs, and so she did her best to minimise their attention. She hid herself beneath bulky clothes and she only exercised in private. She also started to turn away any boys who showed an interest in her, believing they only wanted to get under her sweater. Her actions only served to reinforce her feelings and complex over her own breasts. All this Claire had learned from Riley confiding in her.

“How did you play Truth and Dare at college. Surely a boy must have dared you to do that before?”

“My college friends were with me. They always made sure it was off-limits.”

“You should have told us. It’s okay. We can go get you your clothes back.”

“No. It’s okay.”

“Are you sure. Are you mad at Beth? I’ll get her to apologise.” The last thing Claire wanted was for the girls to fall out over a dumb game.

“Its fine really. It’s just a game, right? If you can put up with Jody, I can handle a little teasing too.” Claire grimaced. She wasn't sure if it was a good thing she was inspiring Riley to come so far out of her comfort zone.

“If you’re sure.” Claire didn’t really believe she was fine with it but couldn’t deny her friend’s wishes. “Alright Riley, just breathe.” Claire took a deep breath to demonstrate and felt a sleepy haze wash over her. She felt more relaxed than she had any right to be playing truth or dare with her naked brother. Part of her was thinking it would be best to stop before either of them went too far, but that part was quickly getting drowned out. “It’s just like we practiced. It isn’t any different.”

“Yeah, you’re right.” Riley took several deep breaths and her shaking gradually began to slow. “After I heard you were going to a therapist, I thought that maybe that would be worth a try. So, I’ve booked a session with her tomorrow.”

“With Doctor Valentine?”

“Yeah. Do you think she can help?”

Claire considered. She wasn’t entirely trusting of the doctor and her methods, but she didn’t have any proof that the doctor wasn’t doing her best to help them. Riley certainly needed to see someone about her issues though , and perhaps her unorthodox methods were just what she needed to get over her body issues. “I’m sure she will” she said with the most reassuring smile she could manage.

“Thanks Claire. I’m glad I have you to help me with this.”

“Don’t mention it Riley. I was happy to help.”

It was a little before they left for college that Riley had come to her for help. ‘Please, I can’t live like this anymore. How am I supposed to find someone special for me while I’m so hung up on intimacy?’ she’d said. ‘When you find the right man, you’ll want him to see your body’ Claire had assured her but that wasn’t enough to console her. Riley opened up to her about how much the whole issue affected her. Claire had never realised how much it all trampled her friend’s self-esteem. ‘Okay, we’ll get you past this I promise. I need you to work with me though Riley’. ‘Yes, I’ll do whatever it takes.’

Claire had presented her idea to Riley. They would set up a faceless stream, so Riley could practice stripping in front of an audience she couldn’t see and who didn’t know who she was. The idea had terrified her at first, but Claire convinced her the best way for her to get over her fears was to face them. Riley had agreed on the condition that Claire was on the stream with her to help her feel more comfortable. Claire was comfortable enough in her own body, it wasn’t even a consideration to turn down her friend’s plea.

Their first attempt had been understandably difficult for Riley. Claire had set up a stream titled ‘Helping my friend get comfortable stripping’, she’d angled the webcam to cut off their faces, and then turned the monitor so Riley could see they were live. Riley had been as pale as a sheet. Claire took her place next to her and gave her a hug to calm her nerves, then after a moment’s hesitation shimmied out of her own top. While Claire wasn’t so nervous in stripping for a boy, this had also been the first time for her to broadcast something like this, but she hid her own nerves for her friend’s sake. All throughout she gave Riley quiet words of encouragement, reminding her to breathe deeply to steel her nerves.

Finally, almost thirty minutes into the stream Riley made a move. She stopped shaking for a moment, then in one quick motion pulled her top up, as though her will to do so might crumble any second. Claire expected her to stop there but Riley followed through and unclipped her bra before she could lose momentum. It was only when she held the cups to lift them off that she stopped, too paralyzed by fear to continue. ‘It’s okay. We’ll do it together.’ Claire had told her, unsnapping her own clasp. ‘I’m going to count down Riley. Promise you’ll do it with me.’ That seemed to sharpen her friend’s resolve as when she counted to zero, her friend’s hands dropped away to reveal her bare breasts.

Claire hadn't been able to help herself. Riley’s tits were big, round and full. Her nipples seemed to jut out enticingly. Claire had let herself become entranced, letting her own obsession get the best of her. Before she could control herself, her friend noticed her ogling and glared at her in surprise. Claire couldn’t believe herself. She was exhibiting the behaviour Riley feared so much, affirming all her insecurities. She expected Riley to be angry or upset that Claire betrayed her, but she suddenly burst into a fit of laughter.

‘I forgot all about that’ she’d giggled. Riley, like the other girls, had known all about Claire’s confused interest and the internal conflicts she had revolving it, but until now she had done her utmost to avoid making her friend uncomfortable and feed into her complex. Something about the way Riley's boobs fell from her bra caught her by surprise though, and rendered herself unable to resist her instincts.

‘It’s okay. You can look. I know you care about me as a person.’ Riley’s trust and love for Claire had overridden her feelings of inferiority and objectification, and she was willing to humour her friend’s curiosity. It was clear Riley was still quite embarrassed with Claire gawking at them though, so she controlled her instinct to keep staring. She was glad she had momentarily cleared her friend’s worries and anxieties.

From that day on, Claire had been helping Riley with her issue every time the two girls met up. Thankfully, their colleges weren’t too far apart, so Claire got a chance to see her every other week after they moved away. Over their sessions together, Riley had grown to a stage where she could strip topless within minutes of the stream starting so long as Claire was supporting her. It was through their efforts, that Riley felt comfortable wearing something less conservative to the party.

However, it had been one thing to strip in front of camera for people she’d never see, and another entirely to do so in front of a man she had a relation to. That dare had been a real test of her training. Though she’d somehow managed it, Riley couldn’t keep the anxiety from building up inside her and John’s blatant staring hadn’t helped the issue. Claire couldn’t be angry at her brother though as she’d done the same on her first time seeing them, and she hadn’t had drink as an excuse. Even now she wanted nothing more than to openly ogle her friend.

“I’m okay now.” Riley’s breathing had steadied a little. “I’m ready to go again.” Claire could see the girl was still having difficulty, but she wanted to respect her resolve, so she helped Riley back up and over to the circle. Claire took a seat between Riley and where her brother would sit to give her a little cover from his attention, then wrapped her arm around Riley’s back to stroke her shoulder.

A few minutes later John emerged from the bathroom. It had no doubt taken him a while to grow flaccid enough to pee but he started to harden again on seeing the naked girls. Claire couldn’t help but watch his dick stand to attention. This wasn’t her first time seeing it. Even before last night, they’d had mishaps where she’d catch him dressing or masturbating. The first time she’d done so, she’d stood dumbfounded, staring as it burned into her memory, before she slipped out before John noticed. As the first one she’d ever seen in person, it had been her brother’s cock that her imagination built her fantasies on for months, and that had led to some very strange feelings and conflicts that she’d turned to Jody to help her work through.

Her muffled sense of reason finally broke through to her and she pulled her eyes away. John took his place beside her. He could see his member sticking up from the corner of her eye. He was sitting so close it was difficult to ignore. She hated to admit that she was feeling a little horny. ‘Not because of him. I just haven’t gotten laid in a while’ she told herself.

“So which of us were you jerking off to in there?” Jody asked, not giving John a moment to settle.

“Um, uh…” John spluttered. His eyes widened. The girl was just teasing him but his response to the remark suggested she mightn’t have been off the mark, and the way his eyes darted to Riley’s breasts revealed all.

“It’s your question John.” Beth informed him, to spare him and Riley from further embarrassment.

“Oh, right,” he recovered. “Then what’s your biggest fetish?” he asked, a little more ready than last round. He might have been thinking about what to ask on the toilet. Since the girls had long told each other in their first game together, only John was to gain any revelation from this question.

“I like to see brothers and sisters make out,” Jody said with a sultry smile and a wink to John.

“You won’t be seeing that tonight.” Claire butted in before she could get a rise from John.

“We’ll see how the dares go, I guess” came her response before she turned to Beth, who thanks to Claire’s new position was next in the circle.

“I like to be tied up.” John was listening intently as though taking metal notes. Claire found it funny he thought he’d ever use this information.

Riley hesitated to say anything. Knowing the answer, Claire understood why she would have difficulty admitting it to a man.

“Its okay Riley. We can veto your answer.” Claire reassured her.

“Yeah, let’s veto.” Even Beth agreed it was too much for Riley to go through.

“No wait.” Riley stopped the girls. She looked over to John but couldn’t quite look him in the eye. “I like the idea of being ****,” she awkwardly admitted. Claire had been shocked the first time she heard it from such an innocent girl, but she sort of understood the reasoning after talking with her. For a girl who had so much internal conflict holding her back from intimacy, the idea of having someone take that all out of her hands may have seemed comforting. Of course, fantasies were on a completely separate level from reality.

“Don’t be getting any ideas.” Claire stared at John. He looked offended that she would imply he would, and Claire really didn’t think he would, but she didn’t want to risk him taking her admission as an invitation to put pressure on the girl. Riley shrunk into Claire’s shoulder after her admission, but she did seem to stop shaking a little.

“And my fetish…” Now it that was Claire’s turn, it felt really awkward to be telling her naked, erect brother what tuned her on. John clearly had mixed feelings about receiving this information too. She cast her eyes downwards as she addressed her brother to feel a little less uncomfortable. “I like it when guys cum on my tits.”

“That’s your biggest fetish?” John splurted out in surprise at her answer.

“Y-yeah, that’s what I’m into.” Claire felt a little embarrassed that hers was the answer that astonished John. “I have sensitive boobs. It feels good when guys cum on them. It’s like they’re claiming me. I-” Claire realised she’d gotten worked up over nothing. She didn’t have to explain her fetish to him. She had to admit her particular interest wasn’t that common among women, but she felt justified in having it, and she’d never met a man who hadn’t been delighted to scratch that itch for her.

John was wide-eyed at her openness. Claire was starting to embarrass herself. The **** was really starting to sink in now, clouding her mind and unleashing her more ‘liberated’ persona. It was too late to go back now. It wouldn’t be long before she blacked out and her other self jumped in. Thankfully, her friends were with her this time to make sure she didn’t do anything wild.

It was John’s dare next, and he took a moment to decide what to do. If Claire knew her brother at all, she suspected he didn’t want to dare Riley to do anything after her earlier admission, or Beth as he wouldn’t want to seem like he was targeting her after daring her last round. It was unlikely he would dare anything explicitly sexual at this point either.

What he came out with surprised her.

“I dare Jody to spank Beth ten times.”

Claire quirked an eyebrow. Though the girls were quite sexually experimental, none of them were into S&M. She wasn’t aware of any of her friends having been spanked before. She supposed it wasn’t that uncommon, but it had just never come up. Jody didn’t look to like the idea of hurting her friend. Claire wondered if this was something John was into, or perhaps he had conflated bondage with S&M and thought Beth would enjoy it.

“Alright, let’s do it.” Beth broke the silence. It seemed she was willing to go along with it at least, and she was eager to keep the game going. “Jody, sit on the bed.” With Beth willingly complying, Jody dropped her reservations and Beth bent down over her lap. The bed was flat against the wall so the others could see both her face and bare ass. “Make it hurt or it doesn’t count” she said. Beth was never the type to hold back on a dare.

Slowly Jody brought her hand up to hover in the air. It lingered there for a moment as Beth braced herself, before Jody brought it down on her friend’s rear. “Ngh” she yelped between gritted teeth. Jody hesitated for a moment, but Beth motioned her to keep going. Claire watched her brother. He was clearly enjoying something about this scene but the way he winced when Beth took a blow confused her. Jody continued to rain down blows on Beth until the ten were up. On the last blow, Beth let out a moan, which surprised even her. “I think I might have been getting into that,” she said as she shakily stood up. “Really wasn’t worth this though.” She rubbed her ass which flushed red with pain. “I think I’ll stand for a bit.”

Jody’s question was next. Claire knew she’d have some loaded question to embarrass her. “Describe one fantasy for each person you’ve ever fantasised about in this room,” Jody declared. It was more like a dare than a truth, but none of the other’s seemed willing to quibble over it.

Next came Beth’s response. “I fantasised about us all getting drunk and having a ménage à quatre. That was back when I had my bi phase.” Excluding Riley, Beth had probably had something close to that fantasy come true several times. Jody had gotten Claire to mess around with the pair of them, probably aware of Beth's desires.

“Claire” said Riley, a response that shocked Claire coming from the shy girl. She couldn’t help but be curious what those fantasies were. “I, uh… I fantasised about you making me strip and make out with you in front of some men, then you make me pleasure them.” It was more intense than she expected. Obviously, it originated from their training sessions together, which meant the fantasy was somewhat recent. It was likely an outlet for the girl’s fetish in a situation she felt more comfortable. It did make Claire wonder though. Did the fact they were **** to make out suggest she had a bit of a girl-crush for Claire?

Next up, it was Claire’s turn to make her admission. “I fantasised about having drunk, submissive sex with Jody.” That was the easiest to admit. That wasn’t even secret to John thanks to Jody. It wasn’t even really a fantasy anymore either, considering it happened pretty regularly. The next were more difficult. Claire took a deep breath.

“I’ve fantasised about playing with Riley’s tits until she cums.” Claire didn’t feel ashamed of this. It was only natural, given the intimacy of their training sessions, and how much Riley unintentionally teased her, but she was worried how Riley would take it. She checked her friend’s response, hoping she wouldn’t feel betrayed by Claire’s admission. Riley’s eyes widened as she laughed nervously, but she didn’t pull away from Claire, and Claire swore she saw the slighest glimmer of interest when their eyes met.

Finally she came to John, whose eyes were locked firmly on her. There was no denying she’d had a myriad of fantasies and sex dreams involving him when she younger and more naïve. Jody had heard every one of them from her own lips and would no doubt step in if she tried to flake an answer. She didn’t like to recall those embarrassing parts of her history, but Claire wasn’t going to give her that satisfaction. She took a long drink and let the haze wash over her and soothe her shame.

“Once I fantasised about sucking John’s cock while he was asleep.” A round of surprised gasps filled the room. Jody laughed as John almost choked on air. She was the only one who already knew about that particular event. Riley looked up at her, mouth wide open in shock. Beth looked amazed that that she chose to share that. Claire didn’t know why she’d done it. It was a much more embarrassing confession that it needed to be, but now it was out. Claire felt her body becoming flush with more than heat.

This had happened years back, before Claire started becoming sexually involved and gained her reputation. The gossip of other girls had started to grow more explicit, discussing what they’d been up to with their boyfriends and the various rumours and scandals that went on. Claire had never been intimate with a boy at that point and was starting to feel alienated. She got it into her head that she needed that experience to fit in but didn’t want to proposition a guy and be labelled a slut.

Then late one night, while masturbating to the latest pictures she’d borrowed from John’s stash, her horny mind had come up with the idea. She could suck her brother’s cock while he slept. She’d figure out enough to fit in with the other girls and he’d be none the wiser. Back then she’d been naïve enough to think a boy would sleep through a blowjob. She’d come so close to going through with it, even standing over his bed fingering herself, but a voice of reason broke through pleading her not to continue and she’d retreated to finish herself off instead.

Claire dreaded to think how different things would be if she’d let her libido control her then. She could imagine the scene so vividly. She’d be so focused on the experience, she wouldn’t notice him waking up. He couldn’t hold himself back and shot his load into her mouth and onto her as she reeled back. They’d stare each other down in embarrassment and regret as streaks of his seed covered her face. Would that have destroyed their relationship, both feeling too awkward to ever look each other in the eye again, or perhaps, would it have started a new form of relationship between them, spurred on by Jody’s encouragement?

“Claire?” She came to, realising she had been lost in thought. She explained the context to her friends, leaving out that she nearly went through with it. This seemed to appease them a little, hearing it was out of innocent curiosity rather than serious lust for her brother. The other girls weren’t as open to ideas of **** as Jody was, but were more willing to find the humour in it in their current states. John mind was clearly ablaze with the idea that he could have received his first blowjob from his sister. It took him a moment longer to recover from the confession.

Everyone turned to John, who was looking nervously at Claire. As the only person he knew in the room, John was going to have to reveal a fantasy about her. No doubt he’d had countless over the years, and as a boy, they were likely a little more explicit than he’d care to admit. She had to admit she was a little curious, but understanding how nerve-wracking this was for him, she decided to throw him a bone. She made a vigorous jerking-off motion under her boobs so only he could see. The other girls knew about his love for big chests, so it would be no shock that he'd masturbated thinking of her topless. John seemed to register the hint and resolved himself.

“I’ve thought about Claire jerking me off with her tits.” Claire spluttered. She’d wanted him to admit a fantasy about jerking off on her boobs, not with her boobs. At least the flowing drink was softening the impact of their confessed incestuous desires. The other girls seemed more amused at their discomfort than outraged at the confession. Beth leaned in and placed a hand on Claire’s knee.

“It’s fine darling. Boys will imagine sticking their dicks into anything that moves. It doesn’t mean anything.” John looked like he wanted to object to that but thought better of it and took the easy way out. Instead, he turned to Claire.

“I haven’t thought about you like that in years I promise.”

“It’s okay John. Everyone gets horny sometimes.” There was no way he was jerking it eight times a day and wasn’t thinking about the curvy slut that paraded his bedroom in her underwear. She didn’t blame him. She was pretty much asking for it. So she really didn’t mind that John admitted to it. Some small part of her found the confession hot.

“Alright, I think it’s about time, you two started acting like proper siblings. I dare Claire to sit in John’s lap for the rest of the game.”

“Is that it? That’s cute” she retorted. Claire had expected her to ramp up the heat, but it seemed she just wanted to embarrass them making them act like kids. She gently lifted Riley from her shoulder, feeling bad she couldn’t give her friend more support. Then she scooted herself over between John’s legs. It was only when she felt his cock pressing into her back that her eyes widened as she remembered her brother was naked.

“Right, dead cute” Jody giggled at her reaction. “You call that his lap? Sit in it properly.” Jody got up and lifted Claire under the arms, pulled her back and gently dropped her right between his legs. She felt his cock twitch as it settled between her ass cheeks and rode up her back under her skirt. It was impossible to ignore. She felt her entire body heat up and sweat rolling down her back into his lap. The worst part was that the contact was turning her on, and she couldn’t bring herself to fight it. John didn’t seem to know what to do with himself. He placed his hands down by his side to keep them as far from her as possible. Claire could only imagine the awkward look on his face matching hers.

“Can we open a window?” Claire asked.

“Sure, it’s certainly getting hot in here alright.” Jody fulfilled her request before returning to her seat. It was getting on in the evening now, so the air outside was refreshingly cool.

Claire would have been next to ask a question, but her new position placed her last in the round. Everyone turned to Beth to speak.