Second Chance Fuck Failure

By Onania MasturBOT | copyright 2025

 

Paul, a young man with tousled hair, bright eyes, and a constant battle against his own desires, had returned home after a frustrating date. He had met a girl at a local bar, and they had hit it off immediately. However, as the night progressed, things took an unexpected turn. She wanted sex, and he was so nervous he couldn’t get an erection. In a moment of vulnerability, Paul had confessed to her about his chronic masturbation addiction, hoping for understanding and maybe even acceptance. Instead, she had laughed in his face, sneering at his erectile failure and mocking him for his inability to penetrate her pussy.

The humiliation had cut deep, slicing through his already fragile self-esteem. Arriving home, Paul could feel the anger and shame bubbling inside him, ready to burst. He stormed into his bedroom, stripped off his clothes with shaking hands, and collapsed onto his bed. In a fit of rage and self-pity, he began to masturbate. The familiar pleasure washed over him, but this time it was laced with bitterness and resentment.

As he reached climax, his mind replayed the humiliating scene from earlier, and he ejaculated with a furious intensity. The release brought a temporary sense of relief, but it also left him feeling hollow and empty. Paul lay there, spent, wondering how he could ever find someone who would accept him for who he was – flaws and all. But for now, all he could do was succumb to the familiar sadness and loneliness that always followed the fleeting pleasure.

The next evening, as Paul sat alone in his apartment, his phone rang. He hesitated for a moment before answering, not knowing who could be on the other end. To his surprise, it was Katy – the girl from the night before.

“Hey,” she said tentatively. “I just wanted to say that I was really hard on you last night. I shouldn’t have laughed at you like that. Maybe I wrote you off too quick.”

Paul’s heart skipped a beat. Was she actually apologizing? Did she want to give him another chance?

“I appreciate that,” he managed to reply, trying to keep his excitement in check.

“Yeah, well…I feel kinda bad about how I treated you,” Katy continued. “So I was thinking…maybe I’ll make it up to you. But this time, no expectations. You don’t have to worry about getting me off. Just sort of a pity-fuck, you know?”

Paul’s heart sank at her words. A pity-fuck? That’s all he was worth to her now?

But then he remembered how good it had felt when they were kissing and touching each other the night before. And maybe this time would be different. Maybe he would finally be able to perform and show her that he wasn’t a total failure.

“Gosh, I’d like that,” Paul replied eagerly.

Katy came over later that night and things quickly escalated between them once again. This time, Paul was determined to prove himself and show her that he wasn’t just some sad loser who couldn’t get it up.

They started with some heavy kissing and soon enough they were undressing each other frantically. As they moved towards the bed, Katy took off her clothes with an air of confidence while Paul hesitated slightly before removing his own.

Paul mounted her, his breaths coming in quick gasps as his body responded to her closeness. His heart raced and he could feel the heat of her skin against his. He had a full erection and hoped his small penis wouldn’t disappoint her. With a deep breath, he slowly entered her, feeling her warmth envelope him. He let out a sigh of relief as he realized he was successfully penetrating her.

He dit it! He was in her pussy! After years of hopeless jacking off and feeling like less than a man, Paul was in! The warmth of her pussy enveloped him and he almost couldn’t believe it. His first real pussy! He felt triumphant, euphoric, on the verge of a new life. He was going to be a real man! But then, just as he was beginning to savor his victory, Katy’s voice sliced through his focus and shredded his confidence.

“It is in? Is it in yet?” she asked impatiently, her words cutting into him like a cold blade.

Paul’s heart sank, and with it, his newfound confidence. He felt himself go limp, deflated with a familiar sense of dread. He couldn’t believe this was happening again—a ready, willing pussy, and he couldn’t fuck it.

“Limp? Limp! You went limp inside me? You are so fucking pathetic,” she sneered, disappointment etched all over her face. “I give you a pity-fuck, and you can’t even stay hard enough to fuck me. What a jerk-off.”

Paul could do nothing but look down at the ground, feeling embarrassed and ashamed, as Katy continued her tirade.

“Why don’t you just jerk off for me,” she mocked, “since that’s all you’re good for.”

Her words stung, but deep down, Paul knew she was right. Feeling even more pathetic, more worthless than ever, he started to masturbate in front of her. At least he could give her a show if he couldn’t do anything else.

But then his erection returned, and Paul began to moan and thrust into his hand. He felt degraded and exposed, but also strangely liberated.

Katy noticed this and teased him, saying, “Wow, you are really into this, aren’t you? You’re fucking that hand just like a pussy.”

He felt embarrassed, exposed, and humiliated, but in spite of himself, her words were doing something to him. Katy’s taunts somehow pushed his arousal into overdrive. He was jerking off furiously, her laughter cracking the air around him like a riding crop. She laughed and cheered him on, her voice rising above the wet noise of his hand, saying, “Fuck it, big boy, fuck that hand-pussy.”

Paul couldn’t believe how into it he was, how much he was getting off on her derision, on her scorn. “This is the real you,” she jeered, her eyes narrowing with smirking pleasure at how pathetic he was.

Paul winced at her words, but deep down, he knew she was right. He was destined to be pussy-free for the rest of his life, but somehow, for now, it didn’t matter. This was who he was. He groaned in acceptance, in resignation.

Paul’s whole body tensed and then shuddered as he came with furious intensity, ejaculating in long spurts in his hand. It was the best orgasm of his life.

 

— end —