Ness wasn't about to beg his sister to let him orgasm. Tipsy, tired, but horny, he realized his fate--staying hopelessly denied. Teary eyed he surrendered--"That's fair enough Janey. I need to sleep, I can't focus right now."
"I'm sorry Nessy. I just don't think I'll be able to look at you the same if I give you permission." She was right, Ness didn't want to spend the rest of his life knowing that his sister made him cum.
"Let's just go to bed." He sighed.
Retreating to his bedroom, Ness closed the door and undressed. He looked at himself in the mirror, drunken eyes glared back, dopily encircled by exhausted black bags. Even now he was conscious of the pining between his legs. He looked at the nub, suitably effeminate for all that had happened. He had to embrace the sissy side of himself more and more as a result of every encounter with GoonErryDay. The thing which vexed him most was that despite the shame, lack of control and admitting everything to his sister. There was something stirring in him, it wasn't just arousal, it felt like the next logical step for his sexuality. He shook his head.
"That's just the drinks talking," he thought, "this is kink, knock it off." Resistance was futile however, the cage began straining again. The denial seeming all the more enticing, he had no female clothes in the room. Just the hot pink radiating from his cock, it was enough for him to tempt him with the vibrator again.
Even knowing this would only make his libido skyrocket didn't matter to Ness, edges were equivalent to orgasms now. He reasoned that diving deeper into the pit of lust is better than staying on the rim, peeking in. The vibrator sprung to life, though this time Ness knew it's purpose was not for relief, but to embrace despair. He found the sweet spot beneath the cage and began his torture.
Ness already knew what to watch as mercilessly teased himself. He felt there may be solidarity in watching other caged femboys. He searched online, finding a compilation of them vibing their cages, all of them seemingly as desperate as him. He empathized fully, except for when they were able to cum. The envy built within him to a breaking point. He added an extra parameter to his search now looking for clips where the sissies were not allowed to cum. Only a few videos matched his criteria but he soon realized that these were hypnosis files.
The thought of being hypnotized further was equal parts terrifying and thrilling to Ness. The fear lost in place of his curiosity as he clicked on the first video he could find. These videos didn't put Ness into the same trance-like state that GoonErryDay's did, they only reinforced his need to stay denied. Phrases came over the videos that he hardly noticed.
"Good Sissies stay denied."
"Good girls keep their clitties locked."
"You never need to cum."
Each clip only sucked him further in, he could only accept the messages now. The feedback loop was complete--edge, increase arousal, repeat. Each time his mind would reassure him that he was finally about to cum, only for his hand to draw itself away once again. The affirmations were potent to Ness, his inner conflict failing as he realised being told to stay denied only made him edge faster and more frequently. When the video ended he was left with a fierce, imposing dread that overtook him, desperate for more to satiate his pressing desire. He had enough sense left to try one last time for the orgasm he thirsted for, he messaged his gooning fan.
He checked the time, 1:00am. It was unlikely that he'd get a response till the morning. Still, he had to hope.
"I found a vibrator and I think I'll be able to cum in the cage if you let me...~ I can send you the video too?" He hit send. The wait for the reply was unbearable, not knowing if he would even receive one was like waiting for a job offer after an interview. Against his best judgement he continued searching for more clips online to edge to. Before he could begin, he received a reply.
"Lol I wondered if you'd message me again tonight, I fucking knew you would, needy little slut. Tbh I'm a little disappointed, I thought you'd have a dildo for that cute sissy butt but a vibrator will do." Ness realized the thought hadn't even occurred to him. He continued reading, "I'll make you a deal, if you tell me who your keyholder is AND BE HONEST this time. I'll let you cum."
Ness was still feeling the alcohol, his flawed logic concluded that now Jane knew everything he could relay this information without fear of repercussion.
"It's my sister's, she used to be a keyholder and she had a cage in her room, I was so fucking horny earlier I didn't check for the keys and here we are." Ness didn't even think before sending the message, he just needed relief.
"Bruh, you are a fucking idiot lol. Like I've fucked you over don't get me wrong, but this is better than I could've dreamed up. How the fuck are you going to get the keys back from her?" GoonErryDay's tone had changed, now he was asking the questions.
"I told her everything about this situation, she doesn't have the keys either."
"!!!" No words from GoonErryDay at first, until his followup. "Why did you tell your sister that you're caged lol. Wait, does she know about me!?"
Ness was beyond the point of caring--"I told her everything, even about the ruins, she's going to help me out of this situation."
"Bruh, you've had like 3 Ruined Orgasms and a day of being denied lol. You're acting like your fucking life's over."
Ness started to compose his next message. "My life is over! I know it's only 2 days but I never agreed..." He was halted mid flow as GoonErryDay sent another message.
"You do know I have actually paid you for all this? I've been sending you tips for everything... Even now." Ness checked to ensure GoonErryDay was telling the truth. Sure enough, there was an additional 300 quid in his account. Ness deduced that it was 100 from around the time of his first recorded ruin, the chastity cage trap and right now.
While Ness was checking GoonErryDay replied again--"I love this dynamic lol. I mean if you really hate it that much then fine, go crying to your fucking sister like a sissy, beta loser. But if you can be MY sissy, beta, loser... If you just play along... I'll make you fucking rich. Plus, your shitty content will actually be decent too and actually, let's be honest, you fucking love it, I can tell lol."
Ness had dropped all pretenses by this point, he was shocked by GoonErryDay's benevolence. Quite unsure how to feel, he apologized--"I didn't see any of the payments, I'm sorry about that. Honestly I just thought you were taking advantage of me. Trying to humiliate, manipulate and control me... I was sure you were ruining my life~"
"Don't get me wrong. I'm trying to do all of those things, but I'm not here to ruin your life, just your orgasms lol. Anyways, please keep doing this for me, I'll make it worth your while!" Ness was tempted by the offer.
"BTW, I can tell by your accent you're UK based... That's kinda why I chose you, that little hint of Yorkshire accent you've got made me a bit hopeful... Maybe we could meet up some time huh, we might even be neighbors!? Honestly I'd pay like a grand for that. Why don't you sleep on it and let me know?" Surely meeting in person was too much? Ness felt unsure but he suddenly remembered why he messaged in the first place.
"Maybe... Before you go, you said I could cum if I told you my keyholder~"