Date: Tue, 5 Mar 2024 14:40:21 +0100 (CET) From: Keith Castello Subject: My Dad the Widower - Chapter 4 ----- This work is purely fictional and contains explicit material and taboo themes. I don't condone or encourage recreating the acts in this story in real life--in fact, I strongly discourage it! Feedback welcome at ----- Chapter 4 It was the night Dylan asked Garrett to deflower him. Garrett was sitting at the edge of the bed wearing a basketball jersey and a pair of gym shorts. It was the summer before his senior year. Dylan stood in front of him in an old camp shirt and a pair of shorts. Dylan took off his shirt and Garrett remembered drooling in his head at the sight of Dylan's chest. Dylan was just coming into puberty but there was enough there to make it look like a proper chest, albeit barely. He was slender but not scrawny. But what drove Garrett crazy was Dylan's nipples. As soon as he saw them he pictured himself sucking on them--something he imagined he could do all night. Dylan stepped closer and ran his hands up Garrett's chest. "Teach me, Garrett," he said softly. "I want you to be my first." Garrett ran his hands up Dylan's thighs and settled them on his ass. Unlike his chest, his ass wasn't just barely there. It was fat--well above the average for his age--and Garrett loved that. He pulled Dylan closer by the waist and gave him a kiss. He let it linger then stuck his tongue in, and Dylan squeaked lightly in surprise. "Are you sure?" Garrett asked as he pulled away. Dylan nodded. "I can stick it in your pussy?" Garrett asked again softly. "Because once I do, I can't stop, baby." Dylan paused for a bit. Garrett stared at him in anticipation. For a split second, he worried that Dylan might change his mind, and he hated himself for even asking. He caressed the small of Dylan's back gently and gave his ass cheek a squeeze with his other hand, and he decided there was no turning back. "Please, Dylan," he whispered as he went for Dylan's neck. He kissed Dylan's neck lightly as he waited for an answer. Dylan cooed, encouraging Garrett even further. He pulled Dylan in tighter and started frenching his neck. He felt Dylan dig his fingers in his back. "Yes, Garrett. I'm sure," he whispered. It took just those words for Garrett's cock to stand at full attention. He decided this was gonna be both their first time. In reality, it wasn't his first time. He lost his virginity to Julia Drake in his freshman year. She threw herself at him after a date they had and it was over before he could even realize it was happening. Julia was pretty and all, but she was nothing compared to Dylan and the years he spent lusting over him, his little brother's best friend. He came up from Dylan's neck and gave him another kiss. "Yes, *daddy*," Garrett instructed. Dylan nodded and repeated, "Yes, daddy." "Hold on to me, baby," Garrett murmured. Garrett was the star heavyweight of Murphy High's wrestling team, and he was also the reigning state champ. He intended to use all his skill on Dylan that night. He pulled Dylan by the back of his knees and lifted him as he stood. Dylan clung to his shoulders, surprised. He rearranged one of his arms so that the back of Dylan's knee rested on the crook of his elbow while his hand went to support his lower back. He locked eyes with Dylan as he did the same with his other arm. Finally, he was cradling Dylan so that Dylan's hole was resting directly on the backside of his cock, separated only by the fabric of their shorts. He had intended to lay Dylan down on the bed, but as soon as he decided to move, his feet took him to the wall. He pinned Dylan to the wall and watched his face a bit more. Dylan was looking up at him with an eagerness in his eye--a begging. With the wall now supporting Dylan, he freed up his hands and ran them to the sides of Dylan's torso, gently grazing his nipples with his thumbs as he moved up. He massaged them lightly and Dylan responded instantly. The silent begging in Dylan's eyes grew more desperate as his brows began to furrow. He saw how easily Dylan was given to submit himself and the hunger in Garrett's chest opened up even more, consuming him slowly but with incredible force. He pulled Dylan up by his butt so that his chest was at the level of his eyes. He drew his attention to Dylan's nipples and immediately took one of them in his mouth. He lost himself to the moment as soon as his tongue met Dylan's nipple. He started flicking it with his tongue while he suckled on the breast. Dylan grabbed the back of Garrett's head and threw his own head back, trying to brace himself against the shockwaves that Garrett's suckling sent throughout his body. "Oh, Garrett," he moaned. Garrett's swollen cock strained even more at the sound of Dylan's moaning. Finally, he grew so restless that he started to cradle Dylan toward the bed. He laid him down gently, staring into his eyes the whole time. "What now?" Dylan uttered. Not saying a word, Garrett continued looking into Dylan's eyes as he slowly peeled off the boy's shorts and underwear. Out of the corner of his vision, he saw Dylan's dick plop to his stomach as the shorts came off, and even further out of that corner he caught a split-second glimpse of Dylan's boyhole. His nostrils flared at the prospect of him finally fucking Dylan, but he tried to keep himself composed. He could feel the cross-eyed, hunchback monstrosity of a pervert inside him trying violently to break free. It occurred to him that he could simply let go of control and ravish Dylan right then--rape him, if he had to--but he didn't want to. Not Dylan. He kept his sights on Dylan's face. He wanted to see how Dylan would react to every single thing he would do. Finally, Dylan's shorts were completely off. Garrett leaned in to give him another kiss. Dylan wrapped his arms around Garrett's shoulders as they kissed torridly. Garrett's stubble started to chafe his lips, but he didn't want to say anything. He observed that Garrett seemed to be enjoying himself, and that made Dylan somewhat proud. But there was also a look in Garrett's eyes that he found intimidating. He had never seen that look before, and he was a little scared to show any resistance. Garrett started grinding on Dylan's crack. He felt Dylan's sweet pucker against the fabric of his shorts, and his hold on his inner freak started to fail a little more. He continued kissing Dylan, but his head started to spin. He felt a high come on, and it was slowly driving him to madness. He fought against the now incessant urge to drop the romantics and defile Dylan completely. He clung to his affection for Dylan in his attempt to control himself and not scare his darling. He pulled away and sat up to get a hold of himself. He looked down on Dylan's erect little penis, and his hand went straight to Dylan's hole. As soon as he touched it, he felt his capacity for restraint dwindle down to its final stretch. He quickly took his hand off it and pulled Dylan's legs up, pressing down his knees to his chest. He was now face to face with Dylan's sweet boypussy, his hands pinning down Dylan's legs. His nostrils flared at the glorious sight and he went berserk. He stuck his tongue completely out and ran it up harshly against Dylan's hole. Dylan moaned, to Garrett's complete satisfaction. He felt like he just marked his territory and he liked how that made him feel. He started to heave lightly as Dylan looked up at him, anxious but wanting. He licked Dylan's pussy again and slowly let go of what little control he had over himself. He pulled Dylan up upside down to a near-perpendicular position, just enough so that he could still see the look on Dylan's face. He held him there as he proceeded to rim the boy. Garrett ravished Dylan's hole for minutes. At first, he rubbed the hole and teased it with his tongue, up and down and in circular motions. Dylan started to moan as Garrett made love to his hole. He wanted to encourage Garrett, but deep down, he was also as frightened as he was excited. He clocked another shift in the look in Garrett's eyes, another one he had never seen before. It was devilish, almost malevolent, and it made him slightly uncomfortable--cautious. Garrett wrapped one arm around Dylan's waist as he started sticking his tongue inside Dylan's pussy. He had intended to do this a little bit at a time but his impatience got the better of him. He stuck it in all the way. He saw Dylan roll his eyes back as he did, and he took this as license to continue being rougher than planned. He closed his eyes and drew all his focus to the task at hand. He dug his tongue in as deep as he could, and pulled it back out. He felt Dylan's fingers start to dig into his thighs. He repeated his tongue's back and forth, luxuriating in Dylan's red hot insides. He grinned at the thought that his cock would soon be where his tongue was then, in just a few minutes. Garrett reached down to grab his cock as he continued tongue-fucking Dylan. Immediately, he felt a large moist patch in his shorts where the head of his cock rested, and he decided it was time. He laid Dylan back down and got off the bed. "Come here," Garrett instructed. Dylan sat up at the edge of the bed, and Garrett repositioned himself to stand in front of him, his crotch now directly in front of Dylan's face. He dropped his shorts and stood there for a moment, allowing Dylan to get acquainted with his bare cock. Dylan just stared at it, his mouth slightly agape. Garrett found this briefly amusing, until that was eclipsed by a wave of green lust. The sheer image of his swollen cock against the contrast of Dylan's soft face and small frame so aroused him that another drop of precum oozed out of his slit. "Hold out your tongue, baby," Garrett said. Dylan complied. Garrett held the shaft of his cock with one hand and the back of Dylan's head with the other. He gently pulled Dylan's head toward him and rubbed the tip of his cock on his tongue. His nostrils flared at the sensation of Dylan's spongy tongue and hot breath. He instructed Dylan to keep holding his tongue out as he smeared precum all over it. His instinct was to shove it in all the way, but a part of him wanted to enjoy the tease a bit more. So instead of shoving it in, he thrust upward slowly against Dylan's face to let the rest of his shaft get a feel of Dylan's tongue. The whole movement was electric. When Dylan's tongue got to the base of his cock, Garrett hissed lightly through his teeth at the sight. His cock now rested fully on top of Dylan's face. He relished the sight of his veiny cock branding Dylan's timid face. "Lick my balls," Garrett instructed, and Dylan started to flick his tongue. "Keep your tongue soft," Garrett added. Dylan complied. He started lapping Garrett's balls with his tongue. "Good boy," Garret whispered, dizzy. Despite the encouraging words, Dylan remained anxious. The look on Garrett's face had completely changed. It seemed uncaring and villainous; Garrett was no longer the big brother he never had, and it felt like the big man in front of him was a capricious stranger. Worse, Garrett seemed to be in a sort of trance, and he was afraid that Garrett couldn't snap out of it. Dylan quickly grew more apprehensive, but he didn't want to say anything for fear of how this other Garrett might react. He realized how far removed this moment was from what he originally expected, and he felt a pang of deep sadness. He felt alone, but he kept that to himself as he continued servicing Garrett's balls. Garrett pulled his balls away and grabbed the shaft of his cock. He squeezed out another drop of precum and smeared it across Dylan's lips. "Open your mouth," Garrett said. Dylan did as instructed. "Wider," Garrett added. He gripped the back of Dylan's head as he guided the tip of his cock toward Dylan's open mouth. He felt Dylan's hot breath wash over his swollen penis, and he sighed. He had barely touched the inside when Dylan recoiled. "W-wait," Dylan said. "I...I don't know how to do that, Garrett," he added. "Just pretend it's a popsicle," Garrett replied curtly. Dylan strained his jaw as he started to take in the head of Garrett's cock. He closed his eyes and sucked on it as if it were a popsicle, as he was instructed. "Look at me," Garrett whispered. Dylan opened his eyes and looked up at Garrett. He tried his best to keep sucking the head of Garrett's cock, but the sheer girth and the way his cock was curved up made it extremely strenuous on Dylan. But he was afraid to stop. "Deeper," Garrett commanded. Dylan attempted to take in as much as he could, his jaws burning. Apparently it wasn't enough because Garrett tightened his grip on the back of his head, and started thrusting. Dylan retched as Garrett's cock plunged into his throat, but Garrett continued thrusting. He struggled to keep looking up at Garrett. Tears started to stream down his face from all the gagging. Garrett attempted to crack his jaw open, continuing on with his rough thrusting. "Oh yeah," Garrett moaned. He couldn't speak, but Dylan started to sound out in protest. Garrett's thrusting became more violent and it was now virtually impossible for him to breathe. He started tapping on Garrett's thigh but it went unnoticed. He tried sounding out louder. "Watch the teeth!" Garrett scolded. And that was the final straw for Dylan. He pushed Garrett away with all the might he could muster. As soon as Garrett slipped out of his mouth he gasped, taking in a huge breath. He retreated further into the bed as he continued heaving. As soon as he caught sight of Garrett's shocked face, he couldn't help but bust down in tears. Garrett was stunned. He stared on, frozen, as Dylan tried to catch his breath. As soon as Dylan's eyes met his, Dylan began to curl up and sob. Whatever spell he was under was shattered instantly. He climbed on to the bed to hold Dylan but the boy scooched away, crying. "Dylan, baby, what's wrong?" Garrett asked softly. "Did I hurt you?" He stared at Dylan with a concerned look on his face, waiting for a reply. Dylan wrapped his arms around himself, continuing to sob. "You were being so rough," Dylan said quietly, after a long pause. "And mean," Dylan added, the tears streaming freely down his cheeks. Garrett hated himself at the sound of Dylan's reply. And the sight of his tears broke his heart. He was angry at himself for allowing this to happen. He was speechless. "I...I thought you said you loved me," Dylan added. "I do, baby," Garrett responded earnestly. "I do love you." Garrett nestled in closer and slithered his arms around Dylan's waist, hugging him from the side. He rested his head on Dylan's and repeated, "I do love you, baby." Dylan paused. "...then why were you being so rough and mean?" he asked meekly. Garrett wiped away the tear that had just trickled down Dylan's cheek. "I didn't mean to, baby. I didn't even realize I was being mean." He kissed Dylan on the head as he felt him loosen his resistance to his hug. "It's just...it's how you made me feel, baby. It just felt so good, I...I guess I couldn't help it." Dylan had stopped crying as he listened to Garrett explain. "It felt good?" Dylan asked. "So good," Garrett replied as he started giving Dylan little kisses on the cheek. "I'm sorry, baby. I didn't mean to hurt you. It just felt so good." "That's all I wanted, Garrett." Dylan caressed Garrett's forearm. "I wanted to make you feel good tonight. I guess...I guess I just didn't expect you to be so rough." "I'm sorry, baby. Would it help if I promised to be more gentle?" Dylan smirked. "Is that something you can really promise?" Garrett chuckled as he wrapped his arms tighter around Dylan, relieved that his mood was changing. "Okay, maybe not. But I can promise to stop if you say so?" Dylan turned his head to look Garrett in the eyes. He saw that he was sincere, and he reckoned that Garrett's beastly side only came out during sex. He figured it was something he would have to accept about Garrett, if he wanted a deeper relationship with him. He warmed himself up to the thought, until at last he found it acceptable. What was important was that Garrett's roughness didn't mean he didn't care--it was just how he was, during sex. "Okay," Dylan replied softly, bringing a smile to Garrett's face. Dylan smiled back, and Garrett moved in to give him a deep kiss, tightening his hug on Dylan and caressing his waist. His cock began to swell again as it rubbed against Dylan's side. Dylan allowed himself to be swallowed by Garrett's frame as he kissed him back, cognizant of the growth that was poking at his side. "Come here," Garrett said softly. Garrett laid Dylan down on the bed gently and climbed on top of him. He spread Dylan's legs with his knees and laid on top of him as he went in for another kiss. Dylan ran his hands up Garrett's chest and wrapped them around his shoulders. In a short while, Garrett started grinding again against Dylan's crack. His shorts were no longer in the way this time and he felt the bare tip of his cock rub against Dylan's pussy. Dylan let out a soft `mmm' at the touch, sending Garrett into another dizzy spell. He kissed Dylan deeper in an attempt to smother his inner rapist. It was screaming in his head, demanding him to shove it all in without regard. But he was determined to control it, this time. The image of Dylan scurrying away from him, terrified, flashed in his head, and he resolved that he never wanted to see that face again, ever. He grinded up against Dylan's hole more intently, making sure not to be too rough. His cock was now leaking precum profusely, and he used his thrusting to smear it all over Dylan's pussy. He managed to get a tiny fraction of his knob in, and his lust intensified in waves as he felt how tight Dylan was at that opening. Dylan braced himself as he felt Garrett's thrusting poke inside him. He knew from his research that this part was supposed to hurt, but the noticeable restraint from Garrett this time around comforted him. Garrett's deep kissing and caressing also reassured him of Garrett's affection, unlike earlier. Garrett continued teasing Dylan's hole until he finally couldn't take it anymore. He pulled away from kissing Dylan and looked him in the eyes. "Baby, I..." Garret started. Dylan stared at him with concern as Garrett struggled to find the words. "I...I know I scared you earlier, but..." Dylan rubbed Garrett's chest gently, trying to encourage him. "I was just wondering if...well..." "If you could still fuck me?" Dylan said. They laughed awkwardly. "Well, yeah," Garrett replied. He stared into Dylan's eyes and kissed him softly. "I need to be inside you, baby," he whispered. Dylan saw the boyish desperation in Garrett's eyes and he found it strangely endearing. "It's gonna hurt, isn't it?" Dylan asked. "That's what they say...but if you want me to stop, just say the word and I'll stop. I promise." Garrett felt a wave of anxiety as he wondered if he'd be able to keep this promise. Dylan breathed in deeply. "No, that's okay. You don't have to stop for me. I don't want you to." "What?" "You said when we started that once you start, you can't stop." "Yeah, but...I don't wanna scare you again." Dylan kissed him on the cheek. "I won't be. I'm ready this time. I don't want you to hold back." Dylan felt his heart race as he said that. He wanted to be strong enough to take in Garrett, violent as he gets, but he also had no idea how painful this was gonna be. Garrett stared at him, unsure. "Please, daddy?" Dylan begged. Garrett grinned at the words, and he dove in to give Dylan another kiss. Dylan's words rang in Garrett's head on a loop as he continued his thrusting slowly. *I don't want you to hold back.* Garrett thrusted deeper with every loop. He felt his cock ooze out a steady stream of precum, allowing him to inch deeper into Dylan's sweet boypussy with every thrust. He pulled away and sat up on his haunches, taking off his jersey and lifting Dylan's legs up by the ankles. He pushed Dylan's legs further to get a better look at his pussy. He caught sight of it and another massive wave of lust hit him, making him weak. Dylan's pussy was smooth and pink, and, despite his earlier teasing, it was still welded shut. He stared at it for a moment, then leaned forward and gave it another harsh lick with his tongue. Dylan squirmed and cooed, and that was all he needed. He stuck his tongue inside Dylan's pussy and made out with it, jamming in as much spit as he could, preparing it well for his monster cock. He set Dylan down after a few minutes and spat on his hand. He coated his cock with the spit as he stared into Dylan's eyes. "Ready, baby?" Garrett asked. Dylan nodded eagerly. He positioned the tip of his cock directly on Dylan's opening, and let it rest there for a moment. "Breathe in," Garrett instructed. As Dylan took the breath Garrett shoved his cock in as much as he could. The tip of his fat, throbbing cock was immediately enveloped in a tight, warm sheath, and he couldn't help but breathe in sharply through his teeth as his rod slipped in. Dylan tensed up completely, his face scrunched up. Garrett leaned into Dylan to comfort him, giving him small kisses while he planted his cock as deep inside his lover's hole as he could take. "Open up for daddy, baby," Garrett said softly. "It should only hurt for a short while." Dylan kept up his breathing as he took in the stabbing pain. His breathing grew shallow and he couldn't help his face scrunching up, but he rubbed Garrett's muscular arm to reassure him that he was okay. Garrett continued giving Dylan little kisses on the cheek as he thrusted slowly. His cock was only a third of the way in but already it felt amazing. Dylan's insides were red hot and it fit him like a glove. His sphincter was clenched tightly around his shaft. He continued thrusting, trying to settle on a rhythm before he attempted to shove it in all the way. "You okay?" Garrett asked. Dylan nodded his head meekly. "Mm-hmm." As Dylan concentrated on settling into the pain, he noticed that Garrett's thrusting was slowly becoming more pleasurable. With every thrust, Garrett grazed a spot inside him that sent waves of pleasure all over his body. In his head he expected each thrust to be as painful as the first, but each one that came was only more pleasurable than the last. Garrett saw that Dylan started to calm down so he sat back up and opened Dylan's legs. As he did, he saw that Dylan was hard now, and that brought him immense joy. He picked up the pace of his thrusting and watched Dylan roll his eyes back. That Dylan seemed to now be enjoying himself emboldened Garrett to attempt to go all in. With every thrust he shoved in slightly more of his cock, watching that Dylan didn't show signs of discomfort. His excitement grew more and more intense as he saw that Dylan started to enjoy every thrust, even as they were deeper and deeper. He also saw that Dylan's little cock oozed out precum with every thrust, and that sent Garrett over the edge. With one final, decisive thrust, he shoved all of himself into Dylan. He watched to see if that final inch made any difference to Dylan's comfort level. When he saw that it didn't, Garrett let go completely. He lurched and pushed down Dylan's thighs as he thrusted a little more violently, keeping his eyes on Dylan's beautiful face. Dylan looked up at him as he fucked him deeply, a glazed look in his eyes and his brows turned upward at the center. Dylan hung on to Garrett's sides as the bed began to quake. Amidst his pleasure, another jolt of fear ran through him as Garrett charged inside him like a bull. He smothered it, focusing on the pleasure and assuring himself that this was just how Garrett was in bed. Garrett felt a wave of affection wash over him as he stared at Dylan's face, mesmerized. He had dreamed for years of making love to Dylan, and he relished the moment he was finally doing it. He couldn't help but lean in for a kiss. He rammed his cock balls deep inside Dylan as he stuck his tongue in his mouth for another kiss. Dylan moaned as his own dick rubbed up against Garrett's belly. "That feel good, baby?" Garrett asked, pulling away. "It feels so good daddy," Dylan replied, a begging in his eyes. "Who's your daddy?" Garrett asked, heaving. "You are," Dylan replied. "I love the way you fuck me, daddy." Garrett planted his fists on the mattress, on opposite sides of Dylan, fucking him even harder as he did. He stared on at Dylan's face as he bred the boy in a frenzy, and Dylan moaned incessantly in response. Dylan ran his hands up Garrett's chest as he saw that his lover was now working up a sweat. Garrett sent wave after wave of ecstasy through his body with every brutal thrust. The pressure around his groin built up slowly, but now it seemed to have picked up. "Oh, daddy...daddy that feels so good." Garrett leaned his head in to take Dylan's nipple in his mouth. As he sucked on it and flicked it with his tongue, Dylan felt the pressure around his groin shoot up to an unbearable level. "Ohhh...ohhh," Dylan moaned as Garrett continued breeding him. Finally, the pressure exploded and Dylan was electrocuted by his own orgasm as his dick spat out jet after jet of cum, his guts caught in a storm as Garrett's fat rod continued ramming in and out of him, splitting him in two. Garrett pulled away from Dylan's nipple and held himself up by his arms as he looked down on Dylan's orgasming dick, surprised. He looked up at Dylan with a grin. "You came!" he exclaimed quietly. Dylan giggled as Garrett leaned in to kiss him. "D-did...did you come?" Dylan asked. "I can cum right now, baby," Garrett replied. He gave Dylan another deep kiss as he picked up his thrusting. He grabbed Dylan's hand and intertwined their fingers. He pulled away from the kiss and stared at Dylan's face. He luxuriated in the feeling of Dylan's insides caressing his cock as he stared at Dylan's unbelievably cute face. The bed was now quaking violently. Soon, he felt the starting pressure of orgasm build up and he planted his fists on the mattress once again. Dylan observed as Garrett brought himself to climax. He always knew that Garrett was bigger than him, but from this angle Garrett looked huge. As Garrett thrusted his strong hips violently into him, he was fully intoxicated at the sight of his big gorilla-man. Garrett heaved and grunted as his balls curled up. With one final thrust he blew torrents of cum into Dylan's tight pussy. He gave Dylan another kiss as he rode his orgasm, trembling, pumping Dylan full of his seed. *** Garrett heaved in his bed as the memory's climax brought him to his own climax. He jerked his cock while his other hand played with his nipple, and then he grunted loudly as his orgasm came. The bed shook as he trembled while his cock spurted out six jets of cum, two of them landing on his chin and neck. He took a deep breath as his orgasm petered out. He opened his eyes and clarity came in a wave of despair. He stared up at the ceiling feeling desperately alone, wrestling with the nebulous feeling of missing Christine deeply and wanting Dylan beside him, in his arms. He grabbed his cum rag and cleaned up as he sighed. In the back of his mind was the matter of how, in the memory he just replayed, Dylan's face kept morphing into Daniel's. *He looks too much like Daniel, don't you think?* And behind that was the more disquieting fact that the melding of Dylan's and Daniel's faces in the memory had no negative impact on his arousal. The matter pended resolution, or, at least, examination. But he chose to shove it back into the back of his head, shaking his head free of it. After putting his pajama pants and shirt back on, he laid in his bed, waiting for sleep. He made a mental note of resolution that his father was right--he needed to tend to his sex life again. The question of how intimidated him, but he promised himself that he'd keep it in mind. Garrett stared at the ceiling as he tried to drift off to sleep. In a few minutes, sleep came, and his mind left him with the day's parting thought: the image of Dylan resting his head on his chest, sleeping soundly. ----- If you liked this story, please consider supporting Nifty by visiting If you *really* liked this story, I'd also appreciate a tip at > :) -----