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2025-05-25
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On cloud nine

Summary:

After years of intense therapy, Sideshow Bob was only cured of one thing - his murderous tendencies. But his obsession was far from over. So what else was he supposed to do when the object of his fascination came right back to him? Graphic Bort.

Notes:

Shout-out to you, Bort enjoyer!

Chapter Text

Off the record, this was a stake out. Absolutely. Waiting a few streets over, he was just a stranger in a car, waiting to meet an old acquaintance. He let passersby walk past without them noticing him, relieved the world was letting him be. The man formerly known as Sideshow Bob was lost in his own little world, cooped up in his car, instead of tasting the freedom he finally deserved after all this time.

Nine years, three months, and eleven days, since he had last seen Bart. It was enough for the world to have forgotten all about him.

He never lost track of time, and his memory remained intact. He wanted to see him. With every fiber of his body. He needed to, he pretended he did it for closure. He had dreamed about him far too many times, and alway forbidden himself to go on with his fantasies. A side of him he had never unveiled to what served as a mental health department in prison. Years of therapy, years of telling truths and half-truths, years of lying to himself and others.

Today, after a long, far too long period of hard work on himself, he was free again, free to sit in his car wherever he wanted. And where he wanted to be most at that moment was in the vicinity of 742, Evergreen Terrace. Not quite near it, but close enough to lay his eyes on him once more. Two hours, nearly three had gone by, but Bob had stopped counting minutes a lifetime ago. Nothing else mattered now, not even his own life ticking away. He glanced sideways when he spotted movement coming from the end of the street, and held his breath.

There he was.

And, oh god, it was just as Bob had feared. Bart Simpson was crossing the street with a couple of friends around the same age as him - but all of them paled in comparison. The boy had grown up, naturally. He was indeed taller, and the result of that growth was the more slender silhouette with which Bart walked with ease. His step was light as he played about with the others, his light printed shirt fluttering up just enough to see the skin that remained pale underneath. His hair, still spiky, was somewhat longer, although one had to look very hard to notice the difference, especially after nine years. But Bob noticed. He took in every detail, from the playful smile adorning his lips, to the familiar confidence he used when interacting with the others. Bart loved to toy with others...

He had turned into the spitting image of what Bob had trained himself to hate. Back in his cell, he couldn't help but daydream about what the boy would be today. Oh, his obsession was far from taken care of. Although he tried. He would force himself to loathe something he longed for, a person he desired in vengeance and something more, a strangely attractive image he didn't ask to yearn for. The kid, he despised. But what Bart was inevitably going to become as he was rotting away in prison, that one had been slowly finding a way into his mind, growing on him, claiming his home. No one knew, and he didn't accept it himself. And to his horror, his imagination had been correct.

Observing him for about twenty seconds after hours of waiting had been worth it. With his somewhat sweaty hands, he found the determination to turn the car engine back on and return home, at long last. Now his life was ruined all over again.

*

The first night in his house felt all the more lonely. Nothing had changed, every single object in the house had remained silent, waiting in sleep for his return.

Finding his bed was a true blessing, however. At long last, he was reunited with the only place in the world where he could find true privacy, away from barred cells and noisy guards and roommates. In his own personal sheets, Bob knew he had to succumb. For the first night of his newfound freedom, he indulged in the release he had always banned from himself. The image of Bart was entirely renewed, finally real, clearer than ever. The short scene he had witnessed was playing on loop in his mind, as he let his imagination do the rest. Even then, he forced some limits upon his fantasy – he remained some way away from Bart, settling for his distant figure, remembering every detail of his expressions, of his movements, of his body. Soon enough, a low groan escaped him. In the darkness of his bedroom, he cleaned himself off, wondering what the hell was wrong with him.

*

A knock came at his door. Bob frowned, as he didn't expect a visit from his parole officer for another week. He sighed and went to the door, not looking forward to talking to nosy neighbors or door-to-door salesmen.

Once again, he held his breath, this time out of shock. Bart Simpson was standing before him. He was facing him, looking straight at him, out in the open. He didn't have to look down too low like he used to when Bart was a boy, but the... young man was looking up at him, only just a few inches. His shirt was different than the day before, more adult perhaps, as this one had no prints as seemed to have been tailored to his slim body. The hem seemed to have been hastily tucked into his blue jeans, guiding Bob's eyes to the most wondrous sight he could only dream to see of him. When he realized he hasn't spoken, Bob finally found his voice.

"I... Bart?"

"Hiya, Bob. So you're out, huh?"

His voice had become deeper, but his tone remained so familiar. A casualness that was so characteristic of their interactions, despite what they usually meant. There was a spark of recognition in Bob for the person he hadn't seen in nearly a decade. But a question was at the forefront of his mind, stupor taking over anything else unwelcome.

"But... How did you know?"

"What do you think? They called me," he replied, as though it were the most normal thing in the world. When Bob remained confused, Bart sighed and explained, visibly excited to know something the other man didn't. "I asked them years ago to warn me when you're out. You know, as a safety measure. I needed to be on my toes when the time comes..."

"And yet you are here," Bob added, although the conclusion didn't quite match the situation.

"Yeah, well, they told me you were better now. That you weren't... murdery anymore. So I figured, might as well pay my... former mortal enemy a visit."

Bob could only stare. Bart was grinning, that smile that used to send a shockwave of rage in him. There was no telling whether he was joking or not, given his appallingly nonchalant behavior. But Bob took this opportunity to enjoy his delighted features, aknowledging the fact that they were directed toward him.

"So, can I come in?" he asked, his bright blue eyes peeking behind his shoulder into the house.

Bob blinked. "Yes. Yes, of course. Make yourself at home."

He stepped to the side to let him in. The younger man walked right past him, entering the house without a second thought, but not without sharing a quick glance with him. As he closed the door behind him, Bob couldn't help but leer. Bart was inside his house, his back turned to him as he walked into the living-room as if he was visiting an old friend, and all Bob could do was run a hand through his thick red curls, his pestering thoughts assaulting his mind with very enticing pictures.

"Feel free to have a seat," he said casually after a dry gulp. "If you need anything, just ask."

"Oh, sure. I'll be fine, though."

Bob joined him in his living-room, and followed his gaze around in an attempt not to stare. Bart flinched slightly when he noticed he was standing beside him, but didn't move. The silent felt stifling, Bart's tension was radiating from him like a heater, and Bob feared saying anything wrong would set the room ablaze. This was a golden opportunity to perhaps befriend him, so he needed to be at his most tactful here, as the last thing he wanted was scare him off.

"Well, since you are here, Bart," he began, trying his hardest to sound composed in his own home. The youth turned to him, confused but intent on listening to him. It wasn't easy for Bob to focus when this face was staring right at him, but he managed nonetheless. "Let me take this moment to apologize in person... I apologize for all the time I hurt you and tried to kill you. I suppose nothing will ever make up for the consequences of my actions, but know that I will do what needs to be done to atone for my crimes. Know that these... troubled times are now behind me, and hopefully behind you, too."

"Alright."

"Alright?" Bob replied, taken aback by the quick answer.

"Alright, you're forgiven. No biggie."

To say that Bob was dumbfounded would have been an understatement. He studied the other's face carefully, trying to find reasons for him to lie. "Really, Bart? You are going to forgive me that easily? After all I've done to-"

"Yes," Bart pressed on with a little smile. "That was years ago, and honestly I'd just rather forget it all. Wouldn't you?"

"Well, I... I don't know what to say, Bart. Thank you," he nearly whispered as he allowed a smile on his lips.

"We could start over. Whaddya think?"

Bob let go of a heavy sigh, but responded with a warm smile. His mind was reeling in bewilderment, like the sword of Damocles grazing the top of his hair had dropped to his feet with a soft sound. There was so much he wished he could do, if only he could let go of all decorum and... and...

"Do you mind if I..." he hesitated, his thoughts jumbling up, growing from bad to worse. Bart tilted his head expectantly – and dear God how adorable that was. "How about a hug to bury the hatchet?"

Bart shrugged again, a little more awkwardly this time, and turned his head away as he mumbled a quiet 'sure'. Bob tensed, fearing he had crossed a line with the suggestion, but since he had accepted he wasn't going to wait around until he changed his mind. He stepped in front of him – rarely had he ever been so close to him – and opened his arms. He leaned ever so slightly and wrapped his arms around Bart's body, pulling him ever so carefully close.

His scent. His skin. His body. Bob took it all in, as much as he could, knowing this might be the only opportunity to. Bart had grown much taller, but he was still nearly a head shorter than him. To have him in his arms right now, and willingly too, the day after his full release – Bob couldn't have dreamed it better. He tightened his embrace, just enough to breathe in his warmth without coming off as too clingy. Bart allowed this, adjusting his balance a little bit, and coiled his arms around Bob's waist until he could lock his hands behind his back. Right then and there, they froze into place.

Bob briefly wondered if he was going to wake up. He was dying to let his hands roam, to make it appear casual. He was dying to bury his face into the crook of his neck, or pull his blond head against his chest. Unfortunately, he felt his crotch twitch slightly in a sudden spike of interest. He took several quiet deep breaths, in order to keep his body under control. This was a hug of peace, this kind of desire had no place in that sacred moment with Bart.

He was counting in his head, only to force himself to let go of him after a while. Upon parting, the urge to lay his lips on Bart's forehead was nearly impossible to resist. And it would have been a chaste kiss, but he figured it would scare him off more than anything. Bart himself looked relieved, incredibly so as he let out a loud sigh and a quiet chuckle. Incredible, Bob thought, understanding that Bart had still been questioning his safety around him. But now that boundaries were broken, he walked away happily, ready to make himself comfortable.

"Would you like something to drink?" Bob asked from the kitchen as he tried to chase impure thoughts from his mind. The absurdity of the situation was not lost on him, but his apparent erection was far from welcome.

"Nah, thanks, I'm good," he replied from the other room. "So, they said you were in therapy all this time?"

Bob walked back with a bottle of Brandy and an empty glass and found him sitting on the couch, waiting for his answer. He currently had his most precious guest over, and Bob was going to behave as the perfect host. "Actually, my therapy took three years of my sentence. But those years were heavily focused on personal issues. And you, of course."

"Must have been harsh," Bart said with a tinge of compassion in his voice.

"You have no idea. But it was for the best, that I knew. So I kept pushing myself." Bob didn't want to dive back into those years of his life, but he knew he owed Bart some truth. He joined him on the couch, settling as close to him as possible without touching him, and poured himself a full glass.

"Glad you did. So, you must have been talking about me a lot," Bart asked with a knowing smirk.

"That's a given. I had to strip myself of all dignity during every session, nearly every day." He noticed Bart blink rapidly for a second at his metaphor, but decided not to overthink it. "Until I became numb to the pain I used to feel. A questionable method, but a very effective one. Medication helped along, but is no longer needed today, fortunately."

"So they didn't like... use big weird electric machines to probe into your brain?"

Bob laughed – a sincere chuckle he thought he had lost forever. "No, no. Those methods are left to the previous century..." He eyed the glass in his hand, but opted to postpone his alcohol consumption and set it back on the coffee table. For now, he wanted to be blissfully aware of his conversation with his guest. "What about you, Bart? What have you been up to all these years?"

"I, uh... Well actually, I just finished high school, barely... Had to repeat that last grade. 'Cause, you know, school's not really my cup of tea."

"And you managed nonetheless, congratulations." Bob was soon filled with incredible joy when Bart returned his smile, touched by his words. "We all have our strengths and weaknesses. We just need to find the balance that makes the most sense." That weakness, for him, was Bart himself, and the way he was trying to suppress an embarrassed smile on his thin features.

"Now I just want to get a job, and maybe someday live off my passion, when I find a reliable one..." Bart explained with underlying bitterness.

"And I hope to hear all about it. I'm looking forward to seeing you shine in doing what you love. If you need help in any way, know that you can rely on me."

"Thanks, Bob. That means a lot..." his voice trailed off. After a short moment of hesitation, he looked away and resumed, "You know, when I got that phonecall, it all came rushing back to me. Not just the uh, dangerous situations I was in with you, but also the times when you were not really a threat. I remembered all those moments... And so, I wanted to see you again. I guess I always hoped you would turn over a new leaf someday."

Bob opened his mouth, trying to find the right words to thank him without sounding overly emotional. But his sheer happiness, coupled with Bart's proximity, called for him to restrain himself tremendously. "I'm delighted that you chose to come over. I want to show you how much I've changed. In hope that we... can get along, as adults," he worded carefully, aware of the double entendre.

Bart's eyes darted about and he licked his lips, making Bob wish it was his tongue there. But he wouldn't look at him. Bob tensed on the couch. Perhaps he was going too fast. Then again, his old enemy had accepted his apology without thinking twice about it. If only he could be blunt and ask what was on his mind. If only he could say out loud what was on his own, without Bart calling him mad and running off in fear. Bob felt like he was walking through a minefield, amazed at how far he'd come but fearing every step. He didn't even know how far it was possible for him to go.

All of a sudden, Bart shifted his back to Bob and lay against his shoulder with a sigh. He remained stiff, however, as if still on his guards. "I hope I'm not a bother."

"Never," Bob replied instinctively. "You were always important to me. It's a pleasure to have you over, you can stay as long as you want."

"Heh..." Bart huffed with a smile. "So I can stay aaall night, right?"

A small chuckle left them both in unison, and Bob reveled in the spontaneous moment. "If... you want to, I can make accomodations for you. It will be no trouble."

He heard Bart open his mouth as if about to say something, but heard no reply – or objection. After a couple of seconds, Bart cleared his throat. "So I suppose you don't have a TV?" he half-joked once again.

"I do not, but I might consider buying one if you convince me it's worth the time and money," Bob replied in the same light-hearted tone, despite the tension hanging in the air. He didn't dare move, lest Bart dropped backward too far and chose to leave his shoulder.

"It's alright. I'm fine like this, catching up with you."

Bob's smile grew from ear to ear, taking advantage of the fact that he couldn't be seen. Oh, how he longed to bury his nose into his spiky hair, stroke his neck, caress his cheek – each body part was so close, yet separated by their relationship. All he dared to do was put his left hand on Bart's shoulder, and even then he took his time to lay all his fingers on the fabric of his shirt. Delicately, he moved some of his fingers to stroke the skin at the base of his neck, enjoying the softness – he could nearly feel the hardness of his collarbone, and he was losing himself in imagining what lay beyond, the warm surface of Bart's-

"So, what do you do for fun?" he asked, bringing Bob back to the living-room. "Beside going for little boys?"

Bob's jaw suddenly hung very low. That cynical remark had to have a double meaning. Or was he reading too much into it? He cleared his throat and shifted slightly, maintaining his grasp on Bart's shoulder.

"Well, beside trying to kill little boys," he paraphrased, hiding the surprise and irritation in his voice, "I enjoy classical litterature, going to live performances and traveling."

"You'd get along so well with Lisa."

You, Bob thought with all his heart. I want to get along with you. To be close to you as often as I possibly can. I want the impossible. Despite his mind screaming at him, he didn't answer. There was no word to describe what he wanted to do. Bart glanced up at him, his hair brushing against Bob's neck as he did so.

"It's cool that we can just hang out, without one ruining the other's life. Am I right?"

He felt his heart might melt if he looked down at him. "I agree whole-heartedly. Were you... looking forward to it?"

Bart rested his head against him once again. Was it Bob's imagination, of did he intentionally push closer? "Y-yeah, kinda. I mean, now I don't have to worry about you trying to kill me anymore. That's a huge load off my shoulders..."

A shiver ran down Bart's spine, as Bob noticed very well. The man wondered what had caused it – past fear? Discomfort? Was the fact that they were sitting together on the couch, in his house – and oh, how Bob didn't want this moment to ever end – stirring something within the younger one?

A new impulse of bravery, encouraged by Bart's strange ease, instructed Bob to push his luck. He swallowed dryly and put his other hand on his other shoulder, then began stroking both sides slowly. It was only meant as a way of comforting him, he could only pretend thinking Bart was too uncomfortable – which might well have been true. The young adult sat up suddenly, surprised by the new touch. But neither faltered, and Bob ran his thumbs along his shoulder blades. He now wished he could slide his fingers on the bare skin underneath, feel it stretch and glide under his touch, but those were scenes for his forbidden daydreams. A backrub was already a small miracle for Bob, who remained very watchful of his every reaction. Glancing discreetly, he noticed Bart's lips were parted, and his eyelids relaxed. His shoulders slouched in surrender, and he lowered his head forward a little. This only encouraged Bob to go further, his mind swirling with all kinds of ways to touch him more, to feel him more, after years of suppressing his deeply-buried thoughts. His fingertips ran along the collar of his shirt, playing with that mystical boundary hiding Bart's deeper privacy. A world of fantasies, all taboo, and he was standing at the doorstep, knocking lightly...

He hadn't realized he had leaned in so close to him. He hadn't realized his own eyelids were drooping. He regained his full consciousness when he felt Bart's hair on his lips as he was planting a kiss on the back of his head. His eyes widened and he backed off immediately, his fingers suddenly hovering over Bart's shoulders.

"I'm sorry," he spoke with shock. "I- I didn't mean to get carried away like this."

But Bart only leaned his head to the side, glancing back briefly. "No, it's fine... I don't mind."

"You don't... mind?" Bob asked in pure disbelief.

"Not really..." he replied quietly. "I guess it's... sweet. It's way better than death threats, you know."

His heart was still thumping loudly in his chest. Now, after the sudden fear of an enormous faux pas, Bob realized that... Bart didn't mind his kissing?

His mouth became dry with excitement. "Will you... allow me to continue, then?" he requested, trying not to sound too hopeful.

The other body met his hands as he leaned back into him. "Yeah, I'd like that."

After a sharp breath, during which he was registering the unexpected answer, Bob took this opportunity to give his spiky hair another kiss. More comfortably this time. He gave another peck, then another, tracing a gentle path down to his neck. Bob was eager to explore. He was eager to feel the young, supple skin against his lips. His fingers hooked onto the collar of Bart's shirt, and he kissed his bare shoulder, slowly, lazily. Despite his mind feeling increasingly foggy, he still kept his eyes open. He wanted to see him, and to see his reactions.

He wanted this to never end.

"Do you like this?" he breathed against his skin as he continued to stroke his shoulders thoroughly.

He heard a shaky sigh coming from his former enemy, whose voice was strangely quiet. "Yeah..."

This reaction caused the unwelcome erection to return. Bob internally cursed himself. He had to think this was all innocent affection, so he still had to be incredibly careful. But he couldn't help but think Bart was enjoying his touch, his proximity...

"I do enjoy cuddling with you... Bart... Do you?"

Bob was well aware of his desire. He was also well aware of the necessary barrier separating them both, keeping the sanity of the situation intact. But their closeness, skin-to-skin contact, was driving him to the edge, and he no longer cared to be careful, at least in his words.

"Yeah. It's..." the blond in his grasp whispered, his words becoming lost. His breathing had also become heavier, Bob noticed.

Curious, he glanced over, and his eyes followed Bart's left arm. His eyes widened when they landed on his crotch, which was being fondled through his pants. His breath was caught in his throat for a moment as he watched Bart rub the fabric of his jeans. Images flashed in his mind, all incredibly intense, delicious – erotic. Without even thinking, Bob released a shoulder and joined him with one hand of his own, first placing it onto Bart's, then stroking the young one's erection through the rough fabric.

Bart emitted a short whimper, and laid his head back against Bob's chest. The man let go of all control at the sweet sound. He couldn't bear to have him face away. He turned Bart's head toward him, and nearly melted at the sight. Bart Simpson's blue eyes looked glazed over, hidden behind a veil of what must have been desire – something he was certainly not expecting to see in him. And what a vision for Bob to have right now, an incredible twist in his life, unhoped for in years of therapy. He was still stroking Bart's erection, but he couldn't help being affectionate at the same time. Pulling his face closer, he resumed the short kisses on the face of the person he wanted most in the world – on the temple, below the ear, on the cheek.

Upon reaching his mouth, Bob opened his own and licked Bart's bottom lip. The sweetest taste of all, better than what he could have ever imagined. As much as he was craving all of him, he also wanted to delay it all. As if savoring a dream, before it all ended. As he was settling on a slow rhythm on Bart's nether region, he ran his tongue on his lip, checking the waters for such an intimate touch. Bart opened his mouth after a few seconds of hesitation, and Bob immediately took over.

He pulled his head in, bringing Bart further into the kiss. He wanted to take his breath away, show him how much he longed for him, show him everything he could do. He wanted to lose himself as well, to allow his every fantasy about this idealized person to run wild, to finally unfold in what actually was reality.

It was Bart who pulled away after what must have been a full minute. Bob opened his eyes on the young man's tired smile. The situation sank in for both, and the former maniac had no idea how they had come to such a sensual exchange.

Without any word uttered, Bob resumed the soft kisses, infinitey doting on his precious little man. He grabbed the hand that Bart was using to masturbate and set it aside, so as to be the only one working for his pleasure – he didn't want any effort on Bart's part, it was only his role to give. He used his other hand to unveil what lay beyond Bart's shirt, to feel the tempting surface of his skin, which had been mostly kept hidden away for so long. Soon enough, Bob wanted to let go of all composure and became greedy.

"Allow me," he spoke, his voice low.

Bart grinned, but his cocky expression disappeared almost instantly - he soon found himself with his fly wide open. Bob was opening up a major boundary, yearning for a treasure he had never dared to even dream of. His blood rushed in his entire body as soon as he lowered Bart's boxer. He couldn't believe what was happening. He pulled out the full-blown erection, the throbbing member now in his fingers. Bart unraveled in his hand, with no shame whatsoever.

"Hold on," Bob interrupted, earning a disappointed look from him. "Please, lie down facing me."

Indeed, he had an idea that he wanted to bring to life, and he couldn't wait any longer. He wanted to taste him, in every place. Bart was right there, his desire laid out in front of him, and oh, how he wanted to appreciate the true measure of said desire for himself. With a puzzled expression, Bart moved out of his grasp. The older man let him go half-heartedly, but watched in awe as he settled on the other side of the couch, his head nestled comfortably on the armrest. His ruffled-up shirt was lifted just above his navel, exposing for Bob's eyes only the entire area of his erection and lower abdomen. A true testament of beauty, at which he would have been content to stare for hours. But his appetite was becoming too great, and the youger one was beckoning him with his eyes, reminding him that Bart had indeed grown up.

He inhaled deeply, then ran his hands up Bart's thighs. His movements were deliberately slow, both for his own pleasure and for the other one's, as Bart was looking down at him with a mix of lust and embarrassement on his youthful features.

"Mmh... Bob..." Bart spoke, straining his voice to be heard.

The man who was called for shifted to have the still fully-clothed legs on either side of his head, the naked member just below him, ready for his performance. With his long fingers and all his anticipation, he pulled at the foreskin to reveal the full length of Bart's penis – a decent size, with blond pubic hair enveloping the base and covering the skin. Bob licked his lips, as if he were about to taste the nectar of the Gods. More precious, Bart was his Nirvana. An unreachable heaven that had found his way directly to him, offering himself to his admiration.

"You... drive me insane..." he growled with every fiber of his body urging him to act.

Before Bart had the chance to respond to his spontaneous statement, Bob took his entire erection in his mouth.

By his sides, he felt Bart's legs shake and bend for support. He was thankful for all the blowjobs he had been forced to give in his former years in that hell-hole, for he was now prepared, experienced enough in the matter to give his guest the best time of his life. The only difference now was that this was Bart Simpson of all people, the person he had been craving in his mind for years.

Skillfully, he alternated between running his tongue up his entire length to build up pleasure, licking and kissing the glans to playfully tease, and sucking on the whole member, either hard, either softly. What an exhilarating sensation it was to have him in his mouth, giving the purest form of pleasure to him – he would keep this moment etched into his mind forever, he knew it. He ran a hand up his upper thigh, and began stroking his stomach, incredibly soft and inviting to the touch. He kept his other hand at the base of his genitals so as not to leave a part of it uncared for. He gave it his all, for Bart.

When he glanced up, he met his eyes. Bart was watching him intently, as if taking mental notes. He was also struggling to keep his eyes open and was chewing on his bottom lip with an extremely tantalizing expression. He squirmed, looking downright hopeless as Bob was bringing him to the brink of release, tormenting him with a near-orgasm. Bob increased his rhythm of sucking and teasing, feeling his own erection palpitate in his pants, as Bart's moan filled his ears as well as his mind. His penis was pressed against his tongue, throbbing and drippling with precum, desperate for release. Bob knew the young Simpson didn't need much longer, and kept him in place when he expected him to explode in his mouth. His semen soon began filling his mouth and Bart didn't dare move. His former attempted murderer gulped down what came from him, finally tasting his seed, swallowing with glee the result of his pleasure-giving work.

And good lord, this was sweeter than anything Bob had ever experienced in his life.