John tries to get off

“Claire I’m gonna go do my thing. Don’t come into our room” John called out to the house then rushed into his bedroom in embarrassment as he heard her acknowledgment. No matter how many times he’d made the announcement, it never got any easier. He couldn’t bare to look either of them in the eye when making these declarations, so he generally just called out across the house when he had to.

Thankfully, his mom had left to run some errands after dropping them both off back at the house and Claire was rummaging around trying to find her phone. John had actually found it in one of his trouser pockets when he checked last night’s outfit, but since he needed it for tomorrow, he decided not to tell her yet. Thankfully she wasn’t too stressed about it, or John would have been wracked with guilt. The tracking app their mom made them install on their phones for her peace of mind showed it had come home last night before it run out of battery.

Right now, John was concerned with the doctor’s claim that he couldn’t masturbate on his own anymore. If he really couldn’t do it, then his requirement to ejaculate eight times a day was going to look harrowing. The last few days of his life had been like a sexual haze for a guy like him, but he’d only been cumming like three or four times each day from feminine stimulation, and the rest had been topped out by his private sessions. John couldn’t begin to fathom how he could double something he was seemingly only achieving through a string of sheer good fortune.

It was the hottest day of the year so far, and John was already drenched in sweat before he even began. Regardless, he steeled himself not to give up until her actually achieved an orgasm, no matter how uncomfortable it became. John dropped on the bed and immediately got to work. His first test was to attempt to get off without any visual stimulation. Having already failed several times in the last day, he was fairly pessimistic about his chance of success, but he frequently switched up his grip on his cock to mix up the stimulation. He imagined a range of fantasies to see if anything worked for him, from memories of the scenarios he’d found himself in the last few days, to imaginary romps with the sexiest women he knew, to **** carnal visions of his mom and sister. He could feel the pleasure in his dick from the stimulation but nothing he did seemed to build up that pleasure.

Accepting he was never going to orgasm from his own imagination, John grabbed his phone from the desk in hopes his photos of Annie might give him some visual aid. He noticed a text from Jody and opened it.

‘Hi John xx Thought you might appreciate this picture of you from last night. Hope you remember the deal made. Looking forward to keep up my end. ; ) xxx’ Attached was a photo John remembered as Jody’s hand-bra dare for Claire. She was stood topless as his hands curled round to cover her nipples. Two details made the picture particularly provocative. John’s hands were lifting her breasts up and in, and the enhanced cleavage and support made them seem extra huge. John could vividly remember the heft of them in his hands. The other detail was the sultry look on Claire’s face as though Jody had caught her in the middle of supressing a moan. John hadn’t realise his touch had had that effect on her.

John thought about the deal he had with Jody. Now he was reminded of it, he had a very vague memory of agreeing to the arrangement. He had no idea what he must have been thinking at the time. He had to admit part of him was tempted to go through with it, but that was the part of him his treatment was trying to fix. He shouldn’t be getting turned on thinking about having sex with his sister. His treatment was already difficult enough without adding in further temptations.

On the other hand, he realised, having Jody as his ‘sex ****’ would fix all the trouble he was having. He would have all the feminine stimulation he needed, and he’d never have to bother his mom or sister about it ever again. He’d never have those weird thoughts about them again because Jody would keep him sexually satisfied. He might even be able to experiment with the dark urges he kept getting if Jody was up for it. There was a lot to gain from the arrangement and John had to admit he was very tempted to agree to it on that aspect alone, but the cost was just too great. Sex with his sister would completely destroy their relationship, and that mattered more to him than anything else in the world. ‘And it’s disgusting for a brother and sister to sleep together’ he had to remind himself.

John’s phone buzzed as he received another two messages from Jody, as if on cue to deepen his internal conflict.

‘Here’s an appetiser to prepare you for the main course xx’

The photo showed Claire and Jody in a passionate embrace, naked save for their panties. Their eyes were scrunched tightly closed as their lips were locked in a sensual kiss. Their hands roamed each other’s bodies, with one of Jody’s squeezing Claire’s ass. Their bodies were pressed tightly against each other, Claire’s tits completely dwarfing Jody’s as they smushed against each other. Seeing their naked bodies beside each other really showcased how much Claire stood out from other girls. Jody couldn’t hold a candle to Claire’s perfect curves. John found himself rubbing himself off to the picture. It wasn’t his fault Claire was just too sexy to resist. No man could resist such raw sexuality.

‘And here’s one to show you just what will be getting for dessert xx’

As if aware that she was outshined by her best friend, Jody sent her a solo picture to accompany it. He had to admit Jody knew how to take a sexy picture. The angle, posing and carefree expression on her face made her look so irresistibly alluring that he almost forgot about his sister entirely.

He could picture having that body as his own personal sex doll and being entirely satisfied. The fact that option was on the table made the decision ever more difficult. He knew the idea of having sex with his own family should be unthinkable, but the more he looked at the picture and imagine doing whatever he wanted to that body, the harder it was not to justify whatever he needed to do to claim it for himself.

John continued to cycle through the photos. Seeing them had gotten John so aroused, if they couldn’t get him off then the whole situation was hopeless. He was so so close to being able to cum. He just needed to push a little more.

“Hey John.”

John jumped at hearing his sister’s voice. In a panic, he instinctively twisted to bring his arm over to hide his erection. Claire was standing in the centre of the room. He’d heard her acknowledge his masturbation warning just a few minutes ago. Why would she come in when she knew what he was doing?

“Relax bro. I’m not looking.”

John’s heart was beating like crazy, his breathing was heavy and erratic, and his skin was soaked with sweat from the heat and his sexual workout. With the initial shock over, John tried to compose himself. She was indeed stood with her back to him, her head just slightly cocked to address him over her shoulder.

“What are you doing here?!” he called out at her a little too loudly.

“Sorry to interrupt, but…” Claire hesitated to continue. John couldn’t see her face, but he could tell she was uncomfortable, either to be here or to say what she was going to say but likely both. “I was just going to, uh…” While he was waiting for her to speak, John’ eyes trailed over Claire’s body. She’d worn a high rising crop top to combat the heat, showing off a generous amount of skin glistening with sweat. What really drew his eyes were her tight booty shorts, whose hem curved up to let her ass hang out. John’s dick, having grown soft at his sister’s sudden intrusion, quickly responded to the eye candy.

“Listen, I was just going to go masturbate, and I-”

“You’re going to what?” John was shocked what he heard Claire say. He thought he must have misheard her.

“Oh, did the doctor not tell you? Me and mom are going to tell you when we masturbate from now on. She said it was to help you feel more comfortable.”

This must have been the doctor’s solution to the concern he brought up at his session. John wasn’t sure what to think about that. He doubted it would make him comfortable. It was probably even more embarrassing to hear his family announce that than it was to do so himself. No doubt it would lead to some rather uncomfortable imagery stuck in his head. Still, couldn’t Claire have waited until he finished to do her thing?

“But I can’t really get in the mood without, you know, something to look at, and it looks like mom’s put a block on pornography.” Lilith had indeed downloaded parental control software after the doctor said John shouldn’t be looking at that stuff. John had to wonder why Claire wanted to masturbate when she wasn’t in the mood though. “I was wondering if I could borrow some of your ‘stuff’ to look at.”

“Oh, sorry Claire. I don’t have anything like that.”

“You don’t have any porn?” she sounded utterly shocked. When he was younger, he’d kept a lot of stuff under his bed, but after gaining access to internet pornography he hadn’t really needed it anymore. Of course, now he couldn’t use that anymore he wasn’t left with many options. He still had a few things down there but he wasn’t just going to show his sister that.

“Well, I have some stuff mom gave me.” Without even thinking, he pointed towards the bottom draw where he kept the VHS tapes his mom gave him. He cringed as Claire followed his movement and started rummaging through them. He could only imagine the horror on her face as she thumbed through copies of ‘Mom Fuckers 3’, ‘Family Free use’ and ‘Busty Cumslut Sisters’. There was an awkward pause as Claire processed what she was seeing.

“Uh, these aren’t going to do it for me.”

“Y-yeah, they didn’t work for me either” John lied.

“Mom gave you this stuff?”

“Well, she got them from Helen next door. I don’t think she knows what’s on them.”

“Helen, huh? I’d never have guessed.”

They sat in silence for several minutes. Claire seemed to be in deep thought. John wasn’t sure what he should so with himself. He felt too awkward to say anything, so he just sat staring at Claire’s ass, waiting for her to make a move. Finally, she seemed to come to a decision and addressed him over her shoulder again.

“I guess you’re having trouble without something to watch too huh?”

“Uh, yeah. Something like that.”

“Alright, I’ll get us something to look at.”

“Us?”

“I don’t just want to leave you struggling. We can cover up with blanket so we can’t see each other.”

The readiness with which she suggested that made John think she’d done it before. He pictured Claire and her friends huddled around a tv at a sleepover, their hands working away under their blankets as they moaned in tandem with the porn star on screen. He was roused from his flash fantasy by her voice.

“Hello? Earth to John. That okay with you?”

“Yeah. Yeah, sure.” If Claire didn’t think there was anything weird about that, then he couldn’t really argue.

“Alright. I’ll be back in a sec.” Claire left the room, leaving John to wonder how he kept managing to end up in these situations. He felt like mutual masturbation wasn’t something normal siblings did, even to help each other out. To him it felt like another taboo he was being pushed into crossing with his family. Maybe John was just being prude though, and college students these days were sexually liberal enough that things like this weren’t a big deal.

Claire returned a minute later with her laptop. “Do you mind plugging this in for me bro?” she asked him. He did as she asked, plugging it first into the outlet, then into the tv while she settled with it beside her on the bed. Once he’d managed to get the cable plugged in correctly, he turned back to find Claire had stripped out of her top. John knew he’d promised to play it cool seeing his sister in her underwear, but she looked so erotic in the lingerie bras she always wore that John felt he would never be able to treat it casually. Luckily, she was too busy fiddling with her laptop to notice the way he gawked at her.

As he returned to the bed to sit, his body brought itself down close to Claire’s out of habit, like they were snuggling in to watch a family movie. Claire looked at him quizzically, but didn’t object or pull away, instead allowing herself to lean into him slightly in response, before returning her attention to the screen.

With them both ready in position, John pulled the blanket over their legs and up over their waist as he would on any wintry movie night. It was the furthest day from wintry however, and he already found his legs warming up to uncomfortable levels. Beside him, Claire began to shimmy in place, presumably pulling down her shorts to access her snatch. John tried not to pay attention as he followed her lead, but it was difficult not to realise they were now sitting bottomless beside each other, especially with his hip now making flesh contact where it wouldn’t usually. He thought about sliding away from her, but if Claire didn’t seem to mind then he didn’t want to make things awkward.

As John was musing, Claire finished what she was doing on her laptop and addressed him.

“Alright, I've got something for us.”