Fun with Riley

“Damn, did you see Claire? She looked wasted.” John overheard his sister's name

“Did you see her going to town on that dude earlier. She wasn’t even drunk.”

“What I’d give to have been in his place.”

“You think she still sucks dick like that while she’s hammered?”

“I have a mate who goes to the same college as her. Says her head was the best he’s ever had.”

“They hook up?”

“Nah mate. She’s just such a fucking slut when she’s drunk, she’ll gargle any cock dangled in front of her.”

“Fucking seriously?”

“Yeah man, there’s pictures and everything. I’ll send you the link. She’s had like every guy from her college unload on her, She probably swallows more jizz than booze. That’s what he said anyway. She never puts out though. Insists she’s still a virgin.”

“Oh, so she’s one of those ‘I’m still chaste while I suck off every guy at school’ types. What a dumb whore.”

“Come on, we better go find her if we want to be front of the queue.”

A rage began to build inside John as he listened to the guys speak. They had no right to talk about his sister like that, treating her like some sex toy to be used for their pleasure. His hand curled into a fist as he approached with a conviction to slam it into their faces.

“Hey John!” His advance was cut short as he felt a hand on his shoulder. He turned back to see Nick siding up to him. When he turned back ahead the boys had already disappeared into the crowd. His frustration peaked.

“What is it Nick? I don’t know where my sister is.”

“Oh, sorry did I catch you at a bad time? I’m not after Claire though. I was looking for Beth actually. I had some business with her.”

“She’s upstairs. I’m heading back to her now.”

“Oh, that’s great. I’ll come with you.”

John sighed. He knew he shouldn’t really lash out at Nick. He hadn’t done anything wrong. He just nodded and started to head to the staircase. To his credit, Nick just followed along quietly, not even inquiring about the bundle of clothes he was holding.

Once they got back to the empty bedroom, John knocked on the bathroom door then stepped aside to allow Nick to deal with his business. A moment later, the door opened a crack and John heard Beth’s voice from inside.

“Oh, Nick? This is a bit of an awkward time right now. Can I come find you later?”

“It’s alright. I just wanted to see if you got that video for me.”

“Yeah, I got it. Don’t know why you wanted it though. It’s really tame compared to what she’s got online.”

“That’s why you’re willing to sell it to me right?”

“Well yeah, but I got her permisshun.” She slurred the last word.

“Oh really?”

“Yeah, I asked her after we took it and told her what you offered and she said it was okay.”

“That’s great. Just send it over whenever then, and I’ll make sure your brother gets that internship. Thanks Beth. I’ll leave you two to it.”

“Huh?” As Nick headed for the door, Beth inched the door open further to see John standing to the side. “Oh John, I didn’t know you were back.”

“Sorry, I didn’t know that that was private.” John hadn’t really taken in much of what was said anyway. He’d been busy taking in deep breaths to calm his frustrations and regain his balance.

“Oh, it was nothing, really.” Once Nick had left the bedroom, Beth swung the door open to allow John in, surprising him. “Oh come on, you’ve already seen us naked!” Without further hesitation, he eagerly stepped into the bathroom after her to join the two naked beauties occupying it. Beth was standing with a hand cocked on her hip on full display to him. Riley was sat stooped on the toilet lid, her heavy breasts swung hypnotically as she swayed on her perch. Neither girl made an attempt to cover themselves nor seemed to mind that his gaze glued to Riley’s voluptuous body.

“Riley’s been sick. I’m gunna take her home in a minute then I’ll come back for Jody.” Now that she mentioned it, Riley did look a bit worse for wear. Beth took the clothes from John and began handing Riley hers.

“Wait!” John cried out before he knew what he was doing. If Riley was going home, this was his last chance to make a move on her. He hadn’t cum since the blowjob contest. The game that had begun with so much potential had just relentlessly teased him. He couldn’t let the night end without getting some release. He needed to feel that perfect body pressed against his.

Being cautious had gotten him nowhere. Now was the time to assert himself. Riley wasn’t in a state to be pushed into anything, but she had shown interest in him that night. He only had two functioning brain cells to figure out how to proceed, but Riley wasn't exactly going to play hard to get. He just had to play it smooth and guide her into it.

“Riley, can I get your number?” The girl raised her head to him on hearing her name. John could see the cogs whirring in her head as she comprehended what he asked her.

“Go on Riley. It's obvious you're into him.” Beth backed him up. Riley gave a shallow smile and nod, then took the phone John offered to her to type her number in. Beth went to hand Riley her clothes back afterwards, but John raised a hand to stop her.

“Hold on Riley, can I take a picture to put in my contacts?”

“I sshould get dresshed firsht.” It was the first John had heard Riley speak in a while and her voice was heavily slurred. John had been purposely holding back on his drinks to enjoy the night more so he wasn’t surprised all the girls were more drunk than him, but Riley was clearly the most affected.

“No. I want one like this.”

“Huh?!” Even in her current state, Riley blushed deeply in embarrassment at his request, which John found irresistibly sexy.

“It’s just you’re so sexy I wanted to capture that on camera.” John was not in the condition for witty flirtation but Riley seemed to take well to his flattery. “You’re stunning. I can’t take my eyes of you.” Riley leaned in with rapt attention on his words. From the beaming smile on her sleepy face, John could see he was on the right track, but she still felt too embarrassed to accept his request. John had to get her to agree to this if he was going to guide her to go further, so he had to take a risk.

“And your boobs are so sexy I just need to see them every day.” Riley startled at his last remark. John was no psychologist, but he had a hunch. Riley was clearly insecure about her breasts. He didn’t know why. Maybe she thought they didn’t look very nice or maybe they were too big. It didn’t matter. What mattered was that now while her inhibitions and insecurities were drowned out, he had the feeling she just wanted to feel good about her body. If he was wrong, then he was going to lose everything. It was time to go all in. “I’ve never seen tits more perfectly shaped and sized than yours. I could stare at them all day. They’re just as beautiful as you.”

Riley was wide-eyed and stunned at what she was hearing. John had no idea what was going on inside her head, but as he continued to shower compliments upon her, a slight smile crept onto her lips, and he knew he had her.

“Okay.” Her blush grew deeper as she accepted his proposal. Beth seemed just as shocked that she accepted but didn’t say anything. Slowly Riley straightened herself up and accepted John offered hand to help her stand up. Her body was on full display for John. He almost lost himself in her ample curves again but remembered what he was supposed to be doing and raised his phone to capture the image forever.

“Fuck, this is the most gorgeous sight I’ve ever seen” John said to get the girl smiling as he snapped some shots. He thought about asking her to pose but it would probably be a disaster if she attempted to in her state so he went with something simpler. “Could you lift your boobs up for me. With your hands.”

“Hm, like this?” she said, eager to please the man making her feel good about herself. She cupped her bust in her hands and gently lifted them an inch. The action made them look so much rounder and fuller. It pressed them together to form a deep, inviting line of cleavage. It looked like she was offering them up to him; a gesture that was so irresistibly sexy that John might have ejaculated just from the sight of it before his treatment. He must have taken a couple dozen pictures of the scene in his excitement. He could tell Riley was becoming aroused as well, just as he was hoping for. As much as he could stare at that scene all day, he had it immortalised now, and it was time to move on.

“How about a group selfie? To remember the night.” John wrapped his arm around Beth to pull her in. She looked at him like she knew the game he was playing, but she didn’t object. She seemed the adventurous sort that would probably have even gone along with this sober. In a way she had been acting as his wingman with Riley all night.

Riley seemed a little deflated that some of his attention had fallen off her but she didn’t resist as John slid in next to her with Beth on his other side. He gave his phone over to Beth to take the shot then wrapped his hand around their shoulders. As Beth started to take them, John slowly pulled the girls in close to him and brought his hand down to cup their boobs as casually as he could. Beth just giggled at his audacity as she took the rest of the shots. John had never felt more powerful than he did now, fully clothed with two naked beauties under his arm. The feeling was intoxicating. As Beth lowered her arm to finish taking the selfies, John stopped her again.

“Hold on. I don’t think that’s really fair me being fully clothed while you’re both in the buff. We need to retake those pictures properly.”

“It’sh fine. I don’t mind.” Riley said.

“No Riley, he’s got a point. It’s not fair he gets a picture of us naked” Beth acted hurt at the idea, though she clearly just wanted to see where John was taking things. John mouthed a silent ‘thank you’ to her.

“I- uh, alright…” With everyone agreed, he quickly stripped down. Beth grinned and Riley blushed when his erection popped back into view. He slipped back into position between the girls and pulled them close. It felt good to feel his bare skin pressed against theirs.

“Keep it going” he whispered to Beth. The girl pretended to keep taking selfies at his behest. After a few minutes, John could feel Riley start to slump against him, once again feeling sleepy.

“Here Riley. Sit down for a bit while Beth and I take a few more.” He didn’t give her a choice, guiding her slowly down onto the toilet lid. Once he straightened back up, her head was level with his cock and she was immediately aware of it.

John pretended to shift to a new pose with Beth, as a means to twist his body towards Riley. He needn’t have bothered with the pretences though, as Riley was oblivious to what was happening around her. Her focus was entirely on the cock dangling before her face. She looked infatuated, and her eyes almost burned with hunger. John knew he had her. Beth turned round to see what was happening. She giggled as she watched Riley’s primal side slowly take over. Any second now, she was going to take it into her mouth.

“I’ve never seen her like this. She’s usually so repressed. You’ll be the second person she ever gives a blowjob to.”

“I’m not after a blowjob.” John responded with a grin. “I’m going to fuck her.”

“Wait, you can’t!” she retorted back with an unexpected hostility that left John confused. He thought Beth was all for him hooking up with her friend.

“Huh? What, why?”

“She’s wasted.”

John looked down at Riley. She was blissfully nuzzling her face into his erection, oblivious to them talking about her.

“Well yeah? It’s okay to fuck her face though?”

“Well… that’s different.”

“How?”

“It just is...” She waited for a moment, trying to formulate how to excuse it. When she spoke, her words came out faster than her thoughts could keep up with, and she paused between each line to allow it to catch up. “She asked me to. She wants to get over her hang-ups. So she told me to cut her loose tonight. She seems to like you, so… But I’m not letting you fuck her. She needs to decide that sober.”

John had to respect her looking out for her friend, even if it left him disappointed.

“Fine. I won’t fuck her, but I’m not settling for a blowjob.” Normally John would have just accepted what the girl offered him, but perhaps it was the drinks giving him the confidence to push for more. “I’m going to fuck her thighs.”

“Her thighs?” She considered. It was less invasive than a blowjob even. There was no way she could refuse. “Fine, but you better not slip inside her. I’ll be watching.”

“Watch as close as you like.” He looked down to address the girl nuzzling against his junk with a softer tone. “Riley, you like my cock don’t you? Do you want to go have some fun with it?”

“Yesh please.”

“Come with me then.” Riley accepted his arms around her as he lifted her to her feet. The extra mass around her chest and hips made her heavier than he realised but his eager anticipation gave him the strength to hold her up. He led her out of the bathroom and laid her down on the bed before he impatiently climbed on top of her.

Instantly John’s entire body felt ablaze with intense pleasure. Since the moment he caught sight of Riley’s luscious body, he’d wanted to sink his fingers into it. Seeing her try so hard to hide her ample curves behind her slender arms had only made him want it more. Now he got to feel the full length of her incredible body pressed against his, skin on skin.

Her flesh was firm, yet soft and yielding; her thighs, her stomach, but her boobs most of all. He held himself back so as not to crush them, but feeling her tits press into his chest and spill out to the side was so hot, and her hard nipples pushing him revealed she was enjoying it just as much as him. He felt tingles running down his spine. It was a feeling he thought only reserved for his cock, but it rippled through every part of him.

He slid himself down her, enjoying the smoothness of her skin, as he lined himself up with the fleshiest part of her thighs. His head now lined up to rest perfectly on her bosom, but he leaned himself back, preferring to play with them in his hands instead. Beth mounted the bed right beside them, ensuring she got a clear view of the action. She seemed no stranger to watching people have sex, but John didn’t feel shy either. Having the naked girl watching them go at it only served to excite him more.

“Feel free to make yourself comfortable if you like what you see” he teased her.

“Don’t you worry about me.”

Finally in position, John psyched himself up to take the plunge. This was the closest he’d ever been to sticking it in a girl, and he was ready. With his knees he kept her logs locked together for maximum tightness. He focused all his effort into not cumming from the first push into them, then with one last breath thrust his hips forward. An intense burst of pleasure shot through spine as the head pushed into the space between the soft fleshy thighs. It took every ounce of focus not to cum on the spot, and he was glad the alcohol had numbed his feeling a little. All too quickly the feeling faded as he settled into position between her legs.

As he felt her warm, fleshy thighs press around his cock, he was reminded he’d been here before – the night before last when he’d woken up with his cock between his sister’s thighs. Riley had a similar body. It felt so familiar he could picture himself back in that position, ready to pull back and shoot his load over Claire. Back then he had let his guilt distract him from how good it had felt. This time there was nothing to feel guilty about. Riley wasn’t his sister. He was allowed to revel in every single moment of the ecstasy this encounter would bring him.

Though the first push in had brought him unimaginable ecstasy, John soon found himself with a problem.

“Uh, Beth, do you have any lube?”

“’Fraid not.”

John sighed. It was proving difficult to continue pushing in and out. Riley’s thighs were just too dry… except, John thought he felt a little bit of moisture. He looked down and saw drops of fluid had dripped down Riley’s legs. Her pussy was soaked.

“Hey Beth. Mind if I use her juices?”

“Her juices?” Beth craned her neck over to see what John was seeing, then giggled. Riley was definitely enjoying herself as much as John was. “Why are you asking me?”

“Oh right.” Riley might not have been the best conversation partner at that moment, but John realised he was acting rude not addressing her.

“You like what we’re doing Riley? You want to keep going?” Riley violently nodded her head in response. “Alright, I’m going to touch your pussy for a second, okay?”

“Hey Beth. Do you mind?” he asked, indicating with his arms that they were keeping him held up. He could have easily shifted so they weren’t, but he wanted to see if he could push his luck.

“You’d like that, wouldn’t you?” Beth snorted but shuffled over regardless. Reaching her hand in, she rubbed her hand over her friend’s pussy to collect her juices, then brought it down to where John’s cock was pressed between her thighs, pushed her fingers in, wrapped them around his cock, and ran them up and down to get it wet. She repeated it until the space between Riley’s thighs were swimming in her juices, then withdrew.

John gave a probing thrust and found it so much smoother and comfortable. Slowly he began to move his hips. Riley ‘s thighs were meaty enough to maintain a nice pressure on his dick even with the lube. Pleasure rippled from it and every surface their skin made contact. Riley moaned, seemingly getting off on the intimacy than the stimulation. John moved his hands up to her boobs to return the favour. They spilled out on either side of her body, making them seem even bigger than they were. John took his time exploring every inch of the tits that had been teasing him from afar all night, but soon settled on playing with her nipples to bring the girl her own sexual stimulation. John allowed his body to take control and indulge in the overwhelming pleasure streaming through his body.

“Oh fuck, Claire. Your tits are so sexy.”

John startled, realising what he had just said. He’d just moaned his sister’s name during sex. What the hell was wrong with him? Why couldn’t he just keep her out of his head? Could he not go one sexual experience without these disturbing thoughts ruining his pleasure?

Riley opened her eyes a crack, noticing him starting to slow down. She was completely oblivious to what he’d done. Beth was still intently watching him going at it, but she didn’t react. Had she not heard him moaning his sister’s name, or was she just pretending she didn’t? Then he noticed. Beth’s hand was grinding into her crotch. It seemed she had taken him up on his invitation after all. Hopefully she had been lost in her own fantasy to hear him. She noticed him staring and turned up to him.

“Girl’s can get pent up too, you know. Keep going.”

He resumed his pace to avoid their suspicions, but his mind was still whirring, and he could feel the pleasure receding. He realised he just had to go with it for now. There was no way for him to enjoy the moment while he was so far inside his own head, trying to control where his mind wandered. It didn’t mean anything if he didn’t let it. As long as he didn’t moan her name aloud again.

“Fuck Riley. Your tits are so sexy,” he corrected his earlier blunder “The most amazing boobs I’ve ever seen.” ‘Except for Claire’s’ a little voice inside chided him, but he ignored it.

“Mmm, so sexy…” Riley was revelling in the body confidence his words were bringing her. She squeezed her thighs together in arousal, and the sudden pressure around his shaft caused a jolt of pleasure to run through his body to reward him for his flattery. John felt her hand worm its way past his stomach as she started to play with herself. Even though this sex act was purely selfish, Riley was really getting into it in her own way

John’s pace really started to pick up as he let himself get back into it. Soon he had to stop playing with Riley’s tits and lower himself down onto her to maintain his pace. Her free arm wrapped around him to pull him in tight against herself. His body felt so right pressed against a woman. Her body burned with an intense heat of arousal. It gave John a strange sense of comfort he never realised his body had been yearning for. He felt his orgasm approaching.

“Riley, let’s cum together” he said with his face nestled in her bosom. The girl just moaned in response, and he heard her fingers rubbing against her pussy with an increased fervour. John gave her a moment to prepare himself then brought himself to the edge.

An intense feeling of déjà vu washed over John. He saw his sister’s face sleeping peacefully beneath his. He was poised, ready to pull out and cover her in his seed. The vision flashed for just a moment, but it was so vivid. It was too late to let it hinder him though. Riley’s body writhed as an orgasm ripped through her body. There was no time to think.

John wrenched his cock out of the fleshy pocket between her thighs, pushing him over the edge. The feeling was so familiar, it took him back. Claire’s beautiful sleeping face, her incredible tits on full display to him. He wanted to paint them white. He always had. He saw himself scrambling to his knees as the first wave shot out of him. He carefully aimed himself, not wanting to miss that sexy body with a single drop. Having been teased for so long, he felt wave after wave spill out, hitting her chest, face and hair until she was almost completely coated in his seed. As he felt the last few spurts approaching, he dove forward and pushed his cock into Claire’s mouth. Her sleeping lips parted easily for him. Overeager, he pushed his cock a little too far down her throat.

A spluttering brought him back from his fantasy. Riley was coughing around the cock filling her mouth.

“Oh, I’m sorry.” John pulled himself back allowing the girl to breathe. “Just lost control for a second.”

Riley looked up at him with a little more cognition in her eyes. It seemed the sudden shock had sobered her up a tad.

“It’sh okay. I had fun” she said with a sly smile. The other girl in the room was not smiling however.

“Good thing it was her mouth you invaded” she said with a stern look. John understood why she was so mad.

“Beth. Don’t be mad at him, please.” Riley spoke up to defend John which just made him feel guiltier.

Beth rolled her eyes with a sigh, then looked Riley up and down. “God, you really made a mess of her. You’re like a fire hose.”

John looked round at Riley and realised what she meant. The girl was almost unrecognisable under the streaks and streaks of sticky fluid that covered her from her head down to her navel. One eye had been glued completely shut. Her boobs in particular had received an extra thick coating and it now dripped down to form small pools in her lap. John would have given anything to watch the two girls lap it up but he knew there was no chance of that happening.

“How the hell did you make this much?” John really wasn’t sure how to answer that. He never used to cum anywhere near this much. Since he’d started his treatment however, he’d noticed his balls had really started to swell up. Not only that, but they also refilled incredibly quickly after he came, so even cumming eight times a day he was still releasing full loads each time. He’d had to eat and drink a lot more to keep up his body’s need. Had ejaculating so much really caused his body to change like this? He couldn’t think of anything else that could have caused it. He wasn’t about to look a gift horse in the mouth though.

Beth shrugged. “Well thanks for getting our clothes back anyway, but I’d better be getting Riley cleaned up and back home.”

“Oh, don’t mention it. “It seemed Beth wanted him to leave. He didn’t blame her. She had a lot of work ahead of her cleaning Riley up, getting her dressed and getting her home safe, and she probably just wanted to get on with it. It did feel a little unceremonious considering how soon after an intimate moment it was though. “I’ll see you later Riley. I hope tonight really helped you out.”

“Bye John.”

John quickly got dressed and headed back out onto the landing. He really wasn’t sure what to do with himself now. For the first time tonight, he was alone. He felt like he should avoid bothering Claire for the rest of the night. He couldn’t really stick with Nick either. He’d probably have more important things to be doing that night.

“Maybe I should just try and meet new people” he said out loud to himself. With at least something of a goal in mind, he headed downstairs to try and find people to mingle with. His heart wasn’t really in it though and he had a hard time breaking into conversation. Eventually he gave up, and went out to sit in a quiet corner of the garden by himself. Nobody bothered him, so he just sat and sipped away at his drinks.

Something was eating at him. He’d done it again. Orgasmed while thinking of his sister. And that night he’d been psyching himself up to fuck her alongside her friends during the game of Truth and Dare. These pervasive thoughts were only getting stronger with each passing day. He didn’t want this. It was disgusting to think of his mother and sister in those ways, but a small part of him wanted it, and he was feeding it constantly day by day. He’d never hated himself so much in his life. As he stewed over what he’d allowed to transpire over the last week, he continued to drink. He just wanted to drown himself into a stupor and forget everything that had happened. He lost track of the minutes passing him by. Some time later he got a text from his sister’s phone. It was Jody, telling him they were heading home. He got up on his shaky legs, and through blurry vision made his way to meet them at the door.