My Transgender Friend

My Transgender Friend

By: Spectrotica247

...

Summary:

Emmett Davis was excited to go on a date with his boyfriend Jensen. However, his hopes were shattered during a game of 'truth or dare' when Emmett shows Jensen his childhood picture that reveals him as a girl before transition, causing Jensen to expose his cruel transphobic colors and cancels the date by the time Brent, Emmett's best friend, arrived. How will Brent help his friend?

Chapter Two - "Mending his Heart"

...

Brent's hand enveloped Emmett's, gently guiding his touch to explore the expanse of his muscular chest. His whisper was hot against Emmett's ear. "Back in fourth grade, I thought you were the cutest girl. And now," Brent's voice grew huskier, "now you're the hottest guy I know. Sexy as hell."

With surprising ease, Brent scooped Emmett up into his arms, showcasing his athletic strength. Emmett swore that his heart would be ripping itself out of his chest right there. He instinctively wrapped his legs around Brent's waist, feeling the comfort of their exposed shirtless bodies pressing against each other. Brent's mouth found the sensitive skin of Emmett's neck, leaving a trail of hot kisses that sent shivers of arousal coursing through his veins. The jock's teeth grazed his earlobe before whispering, "You're so much more than I ever dared to hope for."

Emmett gasped, his eyes fluttering shut as Brent's hands roamed over his bare torso, exploring every curve and plane with hunger.

With a passion that seemed to have been building for an eternity, Brent stumbled forward, his strong arms never loosening their grip on Emmett. The younger boy's back met the coolness of the wall with a gentle thud, his body arching into the contact as Brent's mouth descended on his neck. His teeth begin grazing Emmett's skin, leaving behind a tender mark.

Emmett's hands clutched at the damp fabric of Brent's shoulders, his nails digging in as the jock's hips ground against him, the unmistakable bulge in Brent's pants pressing into Emmett's crotch. The high-pitched gasps that escaped his lips were a symphony of pleasure and surprise, muffled only by the raindrops that pattered against the window pane like the steady beat of a drum.

With smug satisfaction, the older teen pulled back to look at the hickey he had just claimed on Emmett's neck. "Now everyone will know you're mine," he murmured, his eyes dark with desire. Emmett felt a thrill at the possessiveness in his voice.

"Y-yes," he stuttered, his cheeks flushing a deep red. "Yours."

The jock leaned in for another kiss, his hands roaming over the younger boy's body, savoring every inch of him. Emmett could feel Brent's erection pressing into him, and it only served to make him more aroused. His own body responded eagerly. How he can't wait for someone to FINALLY show him how much they love them in an sexual intimate way for the first time after being rejected many times.

Brent carefully sets the brunette down on the edge of the bed, then lowers himself to his knees. Emmett's breath went ragged as he felt the warmth of Brent's hot breath ghosting over his stomach. The jock kissed a trail down Emmett's torso, his lips lingering on the soft skin above his waistband. Each kiss grew bolder, more insistent, as he reached the button of Emmett's jeans and undid it. The anticipation was almost unbearable as Brent's thumbs hooked into the waistband, gently tugging down the zipper.

This was it, the moment of truth that could either make or break them.

Brent gently tugged at the wet denim clinging to the trans boy's legs, sliding the jeans off inch by inch. When the fabric finally gave way, he paused, looking up at the trembling teenager with a soft question in his eyes. "Are you ready for this, Em?"

Emmett swallowed. He had never been more exposed, not just physically but emotionally as well. He nodded, his voice a mere whisper. "Yeah, Brent. I trust you."

The jock leaned in, his breath hot against Emmett's skin as he pressed a soft kiss to the damp fabric of his boxer briefs, just above the hidden treasure beneath. "I'll be careful," he huskily whispered with thick lust. Using both hands, Brent peeled the underwear back, revealing the pinkness that had been hidden for so long. His eyes widened with wonder and respect.

Emmett's body quivered as Brent took in the sight of his aroused vagina, the pink folds glistening with excitement. The jock's eyes were wide with a mix of awe and hunger, his breathing growing more ragged as he reached out to touch the sensitive flesh. His thumb lightly grazed the swollen clit, causing Emmett to gasp and arch his back. The sensation was heavenly, filled with so much pleasure that made him feel more alive than he ever had.

Holy shit, this is real. It's softer than I imagined. He had fantasized about this moment for years, but the reality was so much more intense than any fantasy could ever capture. This is Emmett, the boy I used to know as a girl, and now he's here, with me, letting me touch him like this. He felt a rush of gratitude and love, overwhelming and profound. This is like... his gift to me. His trust that I've earned.

"Wow... your boy pussy looks perfect, dude," Brent breathed with a hoarse tone as his thumb circled Emmett's clit with increasing pressure, watching the blissful expression that overtook his best friend's face. "I can't believe how lucky I am to see you like this, Em."

The brown-haired 16-year-old's body responded to the gentle praise, his hips bucking upward slightly as a soft whine escaped his lips from the jock teasing his sensitive flesh. "Please," he gasped, squeezing his eyes shut. "Please touch me more, Brent... I need you,"

Brent withdrew his thumb and dipped his head before licking Emmett's vagina with his tongue to tease him. The suddenness of the wetness and the heat of Brent's mouth caused Emmett to let out rapid gasps, his eyes flying open in surprise and pleasure. "Oh... oh my god," he choked out, his hands fisting in the bedsheets. The feeling was indescribable, like nothing he had ever experienced before.

Brent's tongue swirled around the sensitive bud, eliciting a moan from deep within Emmett's chest. He had read about this on NSFW fiction sites like FictionPress and Wattpad, as well as fantasizing about it, but the reality was so much more intense, so much more personal.

With a grin, Brent leaned back with mischief in his dark-brown eyes. "Damn, Em, you're so eager. Your pussy's so wet and sensitive." He chuckled lightly, his gaze lingering on Emmett's flushed cheeks and the way his chest heaved with every breath. "It's like you've been waiting for this all your life."

Emmett couldn't help the blush that crept over his face. He had indeed been waiting for this moment, yearning for the acceptance and passion that Brent was now offering him. He nodded, unable to form coherent words. "Y-yeah," he managed to murmur, his eyes never leaving Brent's intense stare. "I have."

The raven-haired junior athlete leaned in closer to Emmett's quivering body. "You know what I've been wondering?" he questioned, his breath hot against the younger boy's skin. "How much boy milk can your pretty little pussy produce?"

This sent shivers down the trans boy's spine, added to the arousal coiling in his stomach. He had never heard anyone talk about his body in such a way before, but coming from Brent, it somehow didn't feel wrong. It felt... right.

"I-I don't know," he whispered, his voice shaky with anticipation.

Without another word, Brent's mouth descended on Emmett's vagina, his tongue delving into the warm, wet folds. Emmett's body jolted at the sudden intrusion, his hips jerking involuntarily as Brent began to explore him with such enthusiasm, each lick and suck sending waves of pleasure crashing through his body.

In his mind, Emmett whispered to himself, Is this... is this how it feels to have someone's tongue in your pussy? The sensations were unlike anything he had ever experienced. The younger teen had always wondered, ever since he had realized his true identity, how this moment would feel. And now, with Brent's tongue lapping at his most intimate spot, he knew it was a feeling beyond words. It felt way better than fingering himself.

Brent's tongue danced around his clit, lapping at the delicate flesh with a finesse that seemed to come naturally to him. Emmett's hands found themselves tangling in the jock's damp black hair, pulling him closer as his moans of sexual pleasure grew louder. The world outside the bedroom ceased to exist, and all that mattered was the connection between them, the gentle dominance of Brent's mouth claiming him in a way no one else ever had.

Emmett's eyes squeezed shut as he felt his body climbing towards a peak he hadn't planned to experience that quick. His hips rocked involuntarily, meeting Brent's mouth with an unconscious rhythm that grew more urgent with each passing second. "Brent, wait," he panted, his voice strained. "I think I'm... I'm going to... to..."

But the 17-year-old either didn't hear him or was too lost in his own desire to stop. His greedy tongue swirled and flicked with purposeful strokes, pushing Emmett closer and closer to the edge. The delicious agony made Emmett's toes curl and his back arch off the bed. His breathing grew ragged as he felt the first tremors of an orgasm begin to build in his core.

"Brent, PLEASE," he begged in a desperate whine. "I can't... Ooh god... I can't hold it..."

The jock's response was to press in deeper, his tongue swiping against the entrance of Emmett's vagina with a hunger that was insatiable. He was determined to taste every drop of the boy's essence, to claim him fully as his own.

As the first spurt of pre-cum escaped him, Emmett's body tightened, his muscles clenching around the jock's probing tongue. "Brent, I'm gonna... I-I'M GONNA—"

Ignoring Emmett's pleas, Brent only increased his pace, his tongue now moving with a fervor that spoke of his own desperate need for release.

With a gasp, Emmett's body convulsed as the first spurt of hot, thick semen filled Brent's mouth. The jock didn't flinch, only swallowing greedily, eager to taste every drop.

"Ahhh... aaaahhh..." Emmett cried out as his eyes were rolled back in his head while riding the waves of pleasure that crashed over him. Soon the last spasms of his orgasm faded, and Emmett collapsed back onto the bed, his body trembling with the aftershocks of pleasure.

Brent pulled back, his mouth glistening with Emmett's seed, a smug smile playing on his lips. "Told you I'd make it happen," he said, his voice filled with pride.

"AAHH... damn it, Brent! I wasn't ready," the trans boy scowled, his cheeks tinted in a deep shade of red. "Why'd you have to make me cum so fast?" There was still pleasure mixed in his exasperated tone as his body was still quivering from the intense release.

The muscular jock only chuckled in response. "Couldn't help it, Em. You taste too good." He wiped his mouth with the back of his hand, smearing the remaining cum. "But don't worry, we're not done." He stood up onto his feet and both his hands moved to the buckle of his belt. "You wanna see my cock, baby? I want you to return the favor."

Emmett's anger faded as his blue eyes widened at Brent's words. He watched, transfixed, as Brent unbuckles his belt and unzipped his jeans, the metal teeth parting to reveal the bulge in his white Calvin Klein boxer briefs. The jock's hand reached into his underwear and pulled out his erect member, a thick veiny beast that was at least 8 inches long, and it was all for Emmett to see. The sight of it made Emmett's mouth water. He had never felt this way before, never knew that the sight of a man's cock could be so... beautiful.

The jock's cock was uncut, a thick, proud shaft that stood tall and strong, the mushroom-shaped head a deep shade of red against the paler flesh of his body. A bead of pre-cum glistened at the tip, a silent proof of Brent's excitement.

Emmett's mouth went into an 'O' shape out of curiosity and a hint of nerves as he took in the sight. He had read about uncut penises before, looked them up on Google images, heck even seen a few in stolen glances at the gym or in the school locker room, but none of those moments could compare to the intimate reality of Brent's arousal standing before him. It was a powerful symbol of his best friend's masculinity, and in that moment, Emmett felt an intense desire to worship it, to show Brent just how much he appreciated the gift of his acceptance and love.

Brent's finger grazed the sensitive tip of his erect cock, smearing the bead of pre-cum that had formed. "Look what you've done to me, Em," he huskily breathed, "You've made me so hard, just by letting me taste you."

Emmett's eyes remained locked on Brent's manhood as he gets up on his knees on the mattress. The jock's confidence and raw desire feels larger than life, in his opinion, and it makes his own feelings for his best friend swell with every passing second. "Y-you're uncut," his voice sounded small and breathless in the quiet room.

Brent's smile grew even more smug as he stroked his cock, watching Emmett's eyes follow every movement. "Yeah, I am," he nods his head. "I was born with it. It's all natural, just like you, baby." The tease was gentle, but it was enough to make Emmett blush even more deeply.

With a gentle touch, Brent peeled back the foreskin of his cock, revealing the plump, glistening mushroom head beneath. It was so big and wet that Emmett couldn't help but let out a low whistle of amazement. "Damn, Brent. It looks so... hot."

The muscular jock chuckled, stroking his shaft with a lazy confidence that made Emmett's stomach flutter. "You think so?" he asked, a knowing glint in his eye.

"Yeah," Emmett breathed, his eyes never leaving the impressive sight. "It's so much bigger than I thought it would be." The admission slipped out before he could stop it, and he felt his cheeks heat up even more.

Brent's smile grew wider. "Well, why don't you get a closer look?" He stepped closer to the bed, his erection bobbing with each step. "Show me what you've got, Em. I know you want it."

The trans teen licked his lips. He had never been with a guy before, never even seen one naked in person, but something about Brent made him feel safe, desired. He leaned forward, his trembling hands reaching out to wrap around the base of the jock's thick cock. The skin was velvety soft, the veins pulsing with each beat of Brent's heart.

He looked up at his best friend, the blue pools in his eyes were written with wonder and a touch of nervousness. "I... I've never done this before," he admitted shyly. "I've only read about it."

Brent's expression softened, the teasing light in his eyes giving way to something more tender. "Don't worry, Em," he assured him, placing a comforting hand on the side of his head. "We'll go slow. Just do what feels right."

With a deep breath, Emmett lay down on his stomach, his heart pounding in his chest like a drum. He looked up at Brent through his lashes, watching as the older boy's expression grew hungry at the sight of his willingness. Then, with a gentle nod, Emmett took Brent's cock into his mouth, the heat and weight of it feeling surprisingly natural against his tongue. He tentatively began to move, mimicking the movements he had seen in porn and read about in erotic fiction, the taste of Brent's pre-cum salty and addictive.

Emboldened by the power he held in that moment, Emmett slid his hand up Brent's shaft, his thumb circling the base of the jock's cock as he took it further into his mouth. He felt a surge of excitement as Brent's hand tangled in his brown hair, guiding him, encouraging him to take more. With newfound confidence, Emmett pushed his tongue into the slit of Brent's foreskin, swirling it around the sensitive head, feeling it swell even more in his mouth.

The sound that escaped Brent's throat was a mix of a sharp inhale and a low, guttural groan that sent a thrill through Emmett's body. He knew he was doing well, and the thought of pleasing his best friend in such an intimate way was intoxicating.

Brent's eyes rolled back in his head as Emmett's tongue happily danced around his cock, exploring every inch of his manhood. The sensation was mind-numbingly good, his body reacting to the sweet pressure and gentle suction with jerks of pleasure. "Oh fuck, Emmett," he breathed, his hips jerking forward slightly to urge him on. "That feels... so good. Yeeeaaahh... that's my boy, Em."

The room grew hazy with lust as the rain outside mirrored the rhythmic pounding of Brent's cock in Emmett's mouth. The jock's hand tightened in his hair, his breathing growing ragged as he watched Emmett's eager, inexperienced sucks. "Just like that, baby," he groaned, his deep voice was dry with burning lust.

The room grew hazy with lust as the rain outside mirrored the rhythmic pounding of Brent's cock in Emmett's mouth. The jock's hand tightened in his hair, his breathing growing ragged as he watched Emmett's eager, inexperienced sucks. "Just like that, baby," he groaned, his deep voice was dry with burning lust.

Emmett felt a sense of urgency building in him as he watched Brent's face contort with pleasure. Determined to give him the release he so clearly craved, he increased the speed of his sucks, his tongue swirling faster and faster around the velvety head of the jock's cock. His hand pumped in time with his mouth, gripping the thick shaft firmly, his own arousal building as Brent's moans increased volume. The taste of his athletic best friend's pre-cum was addictive, and he found himself eager to swallow everything Brent had to give him.

The Davis boy's eyes watered with the effort, but he didn't care, the only thing that mattered was making Brent feel good.

"Keep going, baby," Brent panted as he watched his brown-haired best friend's head bob up and down on his cock. "You're gonna make me cum."

Hearing him mention the word 'cum' fuels the transgender teen's excitement. He had never made anyone feel this way before, never been the source of such raw pleasure. He swallowed down the saliva that had pooled in his mouth, taking Brent even deeper, his throat tightening around the jock's shaft as he tried to accommodate the full length of his best friend's cock.

The boy was screaming in his head, This is it... I'm going to taste another guy's cum for the first time. Oh my god, this is actually happening! The idea was both thrilling and slightly nerve-wracking. He had heard about it, had fantasized about it, but never thought it would be something he'd actually experience. The anticipation was almost too much, his heart pounding in his chest like a bass drum.

He drove himself further, pushing aside any lingering doubt or fear. He wanted this, needed this... And he was going to make it happen.

The muscular jock's thighs tensed, his hand gripping the back of Emmett's head harder as he felt the first waves of his orgasm begin to build. "Aahh... ooh... Aaaooohhh fuck, baby... hahh..." his panting quickened, his eyes squeezed shut. "F-fuck... Shit! You're really gonna make me cum so hard!"

The trans teen's heart raced as he quickened his pace, eager to bring Brent to the edge. He could feel the older boy's cock pulsing in his mouth, the pre-cum flowing like a river, a sign that the dam was about to burst.

... And then it did.

"Haaahhh... AAAAHHHH FFFFUCK!" Brent roared as his body bucked, his hot semen flooding Emmett's mouth as he came, spurt after spurt of thick, sticky fluid that the younger boy swallowed down greedily. The taste was salty and bitter, but to him, it was like nectar from the gods, a physical manifestation of the love and acceptance Brent had just given him.

It didn't take long before the 17-year-old jock's orgasm subsided. Emmett pulled back, his mouth and cheeks sticky with thick white cum. He looked up at Brent with an expression of pride and awe, feeling more connected to him than ever before. "I... I did it," he murmured, his voice shaky.

Brent nodded, a look of pure ecstasy etched on his face. "You sure did," he grinned, his calloused hand still gently cradling the back of Emmett's head. "You're a real natural, Em."

Emmett felt a pang of regret, realizing the gravity of his words. "I wish you had told me sooner," he said, his voice tinged with a mix of wonder and sadness. "We could've saved ourselves so much pain and confusion."

Brent strokes the back of Emmett's head with a soften expression. "I know, Em. I'm sorry for waiting so long." He took a deep breath, his chest rising and falling with the effort of containing his emotions. "But you're here with me now, and that's all that matters." He leaned down to kiss him gently, tasting himself on Emmett's lips, the act feeling more intimate than any kiss they had shared before.

"You're more than just my best friend," he whispered against Emmett's mouth, "you're the person who makes me whole."

The trans teen felt a warmth spread through him, a warmth that had nothing to do with the sticky mess on his face. He reached up to wipe the cum away, but Brent stopped him with a gentle hand. "Let it be," he huskily whispered. "It's a part of us now."

And with that, Brent leaned in for another kiss, this one deeper, more passionate than any they had shared before, sealing their newfound love and acceptance in a bond that transcended friendship.

When they finally broke apart, the taste of Brent's release still lingering on Emmett's lips, a fierce longing burned through him. He looked up at his best friend with pleading eyes, his voice barely above a whisper. "Brent, please," he begged, "I want more... I need more." The words tumbled out of his mouth before he could think to censor them. "I want you to... to take me, to make love to me like that... to be my first time."

The jock doesn't need to be a genius to know what his friend was asking, and knew it was a pivotal moment in their relationship. He took a deep, steadying breath before speaking. "Are you sure, Em? This isn't just some rebound or a way to get back at Jensen, is it?"

Emmett nodded fervently. "I've never been more certain of anything in my life," he said with a tremor in his voice. "You're the one I trust, the one I love. I want you to be inside me, Brent."

The jock felt his chest tighten at the declaration, his heart swelling with love and affection for the brave soul kneeling before him. With a nod, he leaned in for a gentle kiss, his hand tenderly caressing Emmett's cheek. "Okay," he murmured against his lips. "But we're going to take it slow, understand?"

Emmett nodded again, his eyes shining with excitement and nerves. "I understand," he whispered, his voice full of hope.

Brent's smile grew soft as he bent down to kiss him once more, deepening it, feeling the tremble of Emmett's body as the anticipation grew. "Good," he murmured, "Because tonight, baby, we're going to explore every inch of each other, and I want it to be perfect."

The raven-haired older boy sits up and reaches into his pocket of his unbuckled jeans and pulls out a box of condoms. "I was gonna give these to Jensen," he murmured darkly, the anger from earlier still simmering just below the surface. "But fuck him, that asshole doesn't deserve this."

He opened the box and took one out, tearing it open with his teeth before rolling it onto his still-hard cock. The latex snapped into place, and he looked at the Davis boy with a newfound fierceness in his eyes. "Good thing I picked today to get them," he chuckled with pride, holding up his now condom-covered cock. "And just so you know," he said, "this little guy is going to protect you from any unwanted surprises. I don't think either of us is ready for a baby just yet." He tapped the condom with a finger, the latex stretched tight over his erection. "So no worries about you getting knocked up and becoming a teen dad, okay?"

Emmett nodded, his eyes never leaving Brent's cock as it was sheathed in the condom. He knew his parents would flip if he ended up pregnant, especially after the long, emotional journey he had been through to become who he was.

Brent bends down and carefully removes his black and red sneakers one by one, along with his socks. The sight of his bare feet, the vulnerability of the moment, only added to the intimacy that was building between them. He then steps himself out of his jeans, the sound of the belt jingling against the fabric echoing through the room as his muscular legs are on full display.

Now fully naked, Brent climbs himself onto the bed, his muscles rippling with every movement. The mattress dipped under their combined weight as he laid his head over the pillows, his 8-inch cock standing towering proudly. "Come here," he whispered, his hand reaching out to gently pull Emmett on top of him.

Emmett's heart raced as he climbed onto the bed, straddling Brent's hips. He couldn't believe that he was both naked and about to have sex with his best friend. The warmth of their bodies pressed together was a stark contrast to the coldness of the world outside. He looked down at Brent's smiling face, feeling a sense of belonging that he had never experienced before. "This is... it's just..." he stuttered, his words lost in the haze of arousal. "It's more than I ever dreamed."

Brent leaned in and whispered to Emmett's ear. "Just relax, okay? I'll make it good for you, I promise. Let me take care of you." He then spit on his calloused fingers, the sound echoing in the quiet room, and gently pushed one inside the younger teen's tight asshole.

Emmett tensed at first, the sensation foreign and a little uncomfortable. "S-sorry."

"It's okay," Brent murmured, his voice reassuring. "I'll go slow, like I promised." His digit began to move in a slow, steady rhythm, the lubrication easing the way.

The pain was there, a sharp sting that made Emmett's eyes water, but it was soon overwhelmed by a different sensation, one that made his toes curl. He felt his body start to open up to Brent's touch, welcoming the intrusion with a need that was as surprising as it was intense.

"You alright?" Brent asked, hoping he didn't hurt Emmett.

Emmett nodded, his voice a shaky whisper. "Yeah," he managed, his eyes squeezed shut. "It's... it's okay."

Encouraged, Brent added another finger, his movements becoming more confident as he felt Emmett's body start to loosen. The 16-year-old's panted as he felt himself stretching around the junior jock's digits, the sensation of being filled both terrifying and exhilarating.

"You're doing so good, baby," Brent praised, his voice filled with awe and love.

Emmett couldn't find the words to respond, not even in his mind. He could feel his own arousal growing with each gentle thrust, his body preparing itself for what was to come. The pain was still there, a constant reminder of the FTM transition he had undergone, but it was overshadowed by the pleasure that was building, the promise of a connection that went beyond friendship.

As Brent's fingers moved within him, the brown-haired boy felt his walls start to quiver, the beginnings of an orgasm building deep within him. "Brent," he gasped, his nails digging into his friend's (well, boyfriend's) broad shoulders. "I... I think I'm gonna..."

Brent nodded, his own need growing with each of Emmett's reactions. "Just hold on," he murmured with a strained voice. "Just a little more, baby."

And with that, Brent removed his fingers, leaving Emmett feeling strangely empty. But before he could voice his protest, Brent was positioning his fabric-covered cock at Emmett's entrance, the blunt head nudging insistently.

"Ready?" he asked again, his eyes searching for any hint of fear.

Emmett took a deep, shuddering breath and nodded. "I'm ready," he whispered, his voice filled with both excitement and a hint of trepidation. "Go ahead and start… start fucking me already,"

Brent's hands slid down to Emmett's hips, guiding him gently and whispering, "As you wish, baby boy".

With one swift movement, the raven-haired boy pushed into the brunet, the head of his cock breaching the tight ring of muscle.

"Aa-AAHH!" Emmett cried out, his body tense with the sudden pain. But Brent didn't stop, his movements slow and steady, giving Emmett time to adjust to the new sensation.

"You're so tight," he groaned, his voice tight with restraint. "So perfect."

The pain began to ebb, replaced by a feeling of fullness. Emmett felt himself start to relax, his body giving in to the inevitable. "More," he begged, his voice needy. "I want all of you."

With an idea hatched in his head to make this fun, Brent leaned back slightly, his cock still buried inside Emmett. "And here we go, folks!" he announced in a deep, faux-dramatic voice that mimicked the high school football announcer's, "It's the moment you've all been waiting for - the big push for the touchdown!" With each word, he inched deeper, his cock sliding through the tight ring muscle until he was fully seated inside the younger boy, making him gasp at the sensation.

"GOAL!" Brent exclaimed in the same fake announcer's tone, a smug grin on his face as he watched the emotions play across Emmett's face. They burst out laughing, filled with playfulness and passion that only two people who had known each other for so long could share.

Brent stares up at him with love and concern. "Are you okay?" he asked, his voice strained with the effort of holding back.

Emmett nodded, "I-I am," he panted, his body adjusting to the intrusion. "God you're such a cheesy goofball with your sports game announcer impression," he giggled, which helped ease the tension, and he felt his body begin to relax around Brent's cock. "But I kinda like it," he admitted, a shy smile playing on his lips.

"What can I say?" Brent chuckled, kissing him gently. "The Mighty Myers himself always had a flair for the dramatic." With that, he began to move, his hips rolling in a smooth rhythm that seemed to resonate through every fiber of Emmett's being. The pain had transformed into a dull throb, but the pleasure was quickly overtaking it, building into something that was more than physical.

"Fuck, you're tight," Brent groaned, his eyes squeezed shut. "So perfect... You want me to keep it up?"

"Yes," Emmett breathed. "It... it makes it feel less serious. Keep that up, and we'll be scoring three pointers," he quipped.

With a wink, Brent leaned back in, his cock still buried deep within Emmett. "And now, back to the game," he announced in a mock-serious tone, his hips starting to move with a slow, steady rhythm. "Brent Myers is on fire tonight! Hold onto your helmets, because this is going to be one hell of a ride!"

As the 17-year-old's hips pistoned, his cock sliding in and out of Emmett's tight hole, he couldn't help but keep up the playful banter. "And now, folks, we have a breakthrough!" he exclaimed, his voice a mix of passion and mock announcement. "Emmett Davis makes a stunning move, taking every inch of Brent Myers' mighty spear!"

The playfulness helped to ease the tension, allowing them to revel in the intimacy of the moment. Each time Brent pushed in, his voice grew more drawn, his words becoming grunts of pleasure. "Looks like we're scoring another touchdown, baby," he panted. "You're taking it like a champ."

The brunet trans boy could feel his athletic friend's love in every inch of his body, in every thrust that brought them closer together. "Aahh... Aaahhh...," he lightly moaned with passion.

"Come on, Em! You can take it! Push back into me!" Brent shouted, his face contorted with pleasure and exertion as he held onto Emmett's hips tightly. "Show the Mighty Myers how much you want it,"

The junior did as he was told, pushing back with all his might, feeling Brent's cock hit his prostate with a jolt.

"Yes! Yes, just like that, baby!" Brent's voice grew louder, his own hands reaching around to cup Emmett's ass cheeks, giving them a firm squeeze. "HUT HUT!" the muscular jock bellowed, his hips snapping upward, driving his cock deeper into Emmett's willing body. The sudden movement caused a wave of pleasure to wash over Emmett. "That's it, Em! Just like you're throwing the perfect pass!"

Emmett's eyes rolled back in his head as Brent hit his prostate again, his body shaking with the intensity of the sensation. "Fuck... Ooohh... Aaaahhh... yes, Brent... fuck I love it... I've always wanted a man in me," he whimpered, the word slipping from his lips unbidden. "Oh... your cock feels so good,"

The jock chuckled, his movements growing more forceful. "That's what I like to hear," he grunted. "Now, let's go for the big one!"

"Ooohh yeah, Brent... score us the victory," Emmett says between breathless pants as he bounced up and down on Brent's hardened manhood.

Brent playfully announced again to the imaginary crowd, "And here comes the grand finale, folks! The Hail Mary pass of the century!" His moans grew deeper while pounding himself inside the 16-year-old's anus at a quick pace. "Oh, baby, you're gripping me so tight," he grunted. "It's like you're holding on for dear life!"

Emmett threw his head back, his moans turning to laughs as the absurdity of the situation hit him. "You're crazy..." he gasped. "But oh God, it feels so good."

"We're gonna win this game, baby," the athletic teen says, concentrating on (safely) penetrating his trans friend's no longer virgin ass. "We're gonna come out on top!"

Emmett moaned uncontrollably, giving himself over to the sensation of being claimed by the one person who was there for him since day 1. "Yes, oh yes," Hearing him speak with horny pleasure was music to the raven-haired boy's ears as his semen was leaking from the brunet boy's hole. "Keep scoring more points, Myers... keep bouncing my ass," he begged with euphoria.

"Fuck, Em," Brent gritted out, his movements growing more erratic. "I'm gonna... I'm gonna..."

He quickly withdrew his dick from Emmett with a wet 'pop' as he couldn't hold back his need to have that sweet release anymore. He remained on his knees beside the bed, his erection bobbing as he stared down at the condom, which was now a testament to the depth of their love.

"And now, folks," he announced, his voice still filled with the enthusiasm of a sports commentator. He took himself in hand and began to stroke with a fervor that matched the storm outside. "It's time for the grand finale! The victory shot that'll blow the roof off this stadium!"

He let out a few husky pants and manly moans that made Emmett even more horny as his hand moved faster. "Uuaahh... UUUAAAHHH! HERE IT COMES!" He exclaimed.

With a triumphant roar, Brent released his hot load into the condom, his entire built figure tensing with the force of his climax. "TOUCHDOWN! VICTORY FOR THE DAVIS-MYERS TEAM!" He shouted after pumping the last drops from his cum.

He rips the cum-filled condom from his cock and raises it in the air, yelling while panting from orgasm; "VICTORY… hahh… IS OURS!".

Emmett couldn't help but laugh through his own pleasure, the absurdity of their situation mingling with the intensity of their shared intimacy. "How did I get so lucky to have a sexy yet ridiculous goofball?" he asked, his voice filled with affection.

Brent leaned over, giving Emmett a soft kiss as he caught his breath. "I aim to please," he murmured, a satisfied smile playing on his lips.

With the storm outside as their soundtrack, Brent lay back on the bed, his chest heaving with exertion. Emmett, still lost in the aftermath of their shared passion, watched as Brent held up the cum-filled condom with a playful smile. "Thirsty, baby?"

With a playful smirk, the trans teen shimmied up Brent's body like a cat in heat, his eyes locked onto the glistening condom. He took it from Brent's hand, feeling the warm weight of their shared pleasure. Laying his back against Brent's heaving chest, Emmett brought the tip to his mouth and took a deep breath before he began to drink. The warmth and the taste of Brent's cum was intoxicating, a sweet and salty reminder of their intimate connection.

Emmett drained the condom with an enthusiasm that was both surprising and erotic, his cheeks hollowing with each greedy suck. Brent's breathing was still ragged from his own release, but he watched Emmett with amusement and love, his hands gently caressing the younger boy's back as he took in the sight before him. "That's it, baby. Swallow it all down, my manly semen is all for you," Brent instructed.

As Emmett swallowed the last drop of the muscular jock's cum, a warm, wet feeling began to pulse between his legs. Brent noticed the tentative erection of Emmett's vagina, his predatory grin growing wider. "Looks like you enjoyed that as much as I did," he murmured, his eyes darkened with desire as he reached down to stroke the sensitive flesh.

Emmett's breath hitched as Brent's skilled fingers began to tease his vagina, the sensations a stark contrast to the emptiness he had felt just moments before. The gentle strokes grew more insistent, and Emmett's moans grew louder as Brent explored his inner folds, finding his way to the sensitive spot that made his legs quiver. "Brent," he gasped, his hips bucking upwards into the touch. "Don't stop."

Brent's chuckle was low and filled with desire as he continued his ministrations, his thumb circling Emmett's clit with a practiced ease. "Never," he promised, his voice a rumble that resonated through Emmett's body. "I'll never stop making you feel good."

Emmett's blue eyes fluttered shut as Brent's warm breath tickled his ear, his words a seductive whisper that seemed to resonate through every inch of his body.

"Find your peace, Em," Brent murmured, his voice a soothing balm to the brown-haired boy's frazzled nerves. "Relax and let me take care of you."

As if on cue, Brent's expert fingers continued their dance, the gentle circles around his clit growing more insistent with every passing second. Emmett couldn't help but buck his hips in response, his breaths coming in shallow gasps as the pleasure grew more intense. The meditative tone of Brent's voice only added to the erotic symphony, his moans mixing with the sound of the rain outside to create a rhythm that seemed to pulse through the very air around them.

Brent's grin grew wider as he leaned in closer to Emmett's ear. "Mm, you like that, don't you?" he whispered with pure lust. "Let me take you there, Em. Relax and let the pleasure consume you." His words were like a gentle wave lapping at the shore, each one building in intensity, pushing Emmett closer to the edge of his own release.

With a wicked grin, the older boy pulled his fingers out of Emmett's quivering vagina. "Mmm," he hummed, "You taste so sweet, Em."

He leaned in closer, his breath hot against Emmett's ear. "I can't wait to taste more of you," he whispered seductively, sending shivers down the younger boy's spine once again. "But first," he added, "I'm going to make you cum so hard that you forget about everything else."

Emmett lets out a huge gasp as Brent brings his fingers back to his clit, resuming the delicious torment. Brent's touch was like a masterful conductor leading an orchestra, each stroke building the crescendo of pleasure within Emmett.

The trans boy arched his back, his hips grinding against Brent's hand as the pressure grew, his body coiling tighter and tighter like a spring ready to snap.

"Oh, fuck, Brent," Emmett moaned, his voice breaking with the effort of maintaining any semblance of control.

The room grew even hotter with the sound of Brent's deep, satisfied moans against Emmett's ear. His voice was low and gruff, sending shivers down Emmett's spine as he muttered, "Mm, you're such a nasty little whore, aren't you? Just begging for it, grinding against my fingers like that".

Each exhale was a warm caress, each moaning a declaration of ownership that seemed to resonate through Emmett's very soul. The pleasure grew more intense, his body responding to the touch of intimate pleasure.

"That's right," Brent murmured with a gentle coax. "Don't fight it, baby boy. You know you want it."

With a growl of pure need, Brent plunged his finger deep inside Emmett's vagina, the sharpness of his fingernails scraping against the sensitive bundle of nerves. Emmett's body responded immediately, his back arching off the bed as he threw his head back and let out a keening cry. The sensation was exquisite, a delicious blend of pain and pleasure that had him teetering on the brink of release.

"Cum for me, baby," Brent demanded. And with that, he swiped his hot tongue over the shell of Emmett's ear, the gentle pressure sending shockwaves of pleasure through the younger boy's body. The sound of his own desperate whimpers filled the air as Brent's skilled fingers worked their magic, pushing him closer and closer to the edge.

"A-AAAHHH... AAHH I'M GONNA CUM RIGHT NOW!" Emmett's body convulsed as he exploded with huge loads of cum, his eyes squeezed shut as the intensity of his orgasm washed over him like a tidal wave, leaving him trembling and gasping for air.

Brent's chuckle grew darker, a twisted smile playing on his lips as he watched Emmett's body writhe in ecstasy. "That's it, baby," he murmured, his dark-brown eyes gleaming with satisfaction as he observed the younger boy's uncontrolled orgasm.

Emmett's cries filled the room, each spurt of cum painting a picture of pleasure on his contorted features. The sheets beneath them grew sticky with their combined release, the scent of sex mingling with the musky aroma of their sweat.

"So beautiful when you cum," Brent smirked. His fingers didn't cease their relentless motion, continuing to milk every last drop of pleasure from the trembling brunette teenager.

As Emmett's tremors subsided, his body boneless and sated, Brent pulled his finger out with a wet pop, bringing it to his mouth to taste the fruits of his labor. "Mm," he hummed in appreciation, his eyes never leaving Emmett's spent form. "You taste delicious, baby,"

He licked the last traces of cum from his finger, savoring the flavor before leaning in for a tender kiss, sharing the essence of Emmett's climax. The kiss was gentle, a stark contrast to the feral passion that had just played out between them, a silent promise of the unconditional love and acceptance that had grown stronger in the face of adversity.

Emmett's breaths were still coming in gasps as he lay sprawled against Brent's chest, his body still trembling from the intensity of his climax. He couldn't believe the sheer volume of cum that had just erupted from him, a testament to the depth of his arousal and Brent's skillful touch. "How... do you... do that?" Emmett asked, his voice still shaky with pleasure. "I-I've never cum so much before."

Brent chuckled, his eyes sparkling with mischief. "Guess I've got the magic touch," he said, wiggling his fingers in the air. "But really, Em, it's all about knowing what you like and making sure you're as comfortable as possible." He leaned down to kiss the tip of Emmett's nose, his smile softening into something more affectionate. "I want you to feel good, always."

Emmett's cheeks flushed with the combination of embarrassment and satisfaction as he curled into Brent's arms, his heart swelling with love for the boy who had just accepted him for who he truly was.

As Emmett lay there, the warmth of Brent's arms around him and the gentle patter of rain outside, his mind drifted back to their childhood. He remembered 5th grade, the year was 2019 when he was still Emily, age 10. He had yearned to play ball with the neighborhood boys. The humiliation of being shooed away with taunts of "no girls allowed" still stung, even after all these years.

But Brent, age 11, had been different. He had looked at Emmett, with his messy pigtails and hopeful eyes, and simply said, "You can play with me." It was that moment that had planted the seed of friendship that had blossomed into something much deeper over the years.

The memory of the following year was etched into Emmett's mind like a scar. He was 11 years old, and was desperately trying to find solace in his true identity. With trembling hands and a pair of dull scissors, he had hacked away at his hair in the bathroom, trying to sculpt it into something that resembled the boys' styles he so admired. The result was a lopsided mess that had the children at school laughing and pointing. During recess, Emmett had hidden behind a giant oak tree, tears blending with the rain as he mourned his failed attempt to fit in.

12 year old Brent's warm hand on his shoulder had been the only thing that could break through Emmett's sobs. Through the curtain of rain, he looked up to find his friend's eyes filled with understanding rather than scorn. With trembling hands, Emmett had revealed his secret, choking out the words that had been bottled up inside him for so long.

"I never wanted to be a girl, Brent. I always felt like... like I was born in the wrong body."

He had expected rejection, but instead, Brent had reached up and gently tugged his own cap off his head, placing it onto Emmett's. The fabric was soft and warm, a stark contrast to the coldness of the world outside their sheltered embrace. As the cap settled into place, a peculiar sensation washed over Emmett, a feeling of belonging and relief that was so profound it was almost tangible.

"If you're saying you're not a girl… then you're not a girl," Brent had said simply, his voice firm and unwavering. "You're my best friend, and if that means you're a boy now, then that's what you are."

The cap had become a symbol of acceptance, a silent declaration of the unspoken bond that had only grown stronger over the years.

That fateful day, 12-year-old Brent had stood by Emmett's side as he took off the cap that had become a symbol of his newfound identity, his heart racing as he approached his parents. With a tremble in his voice, Emmett confessed his true feelings to them.

At first, Mr. and Mrs. Davis were taken aback, unsure of how to process the revelation that their daughter was in fact their son. The silence that followed was deafening, filled with the patter of rain and the thud of their own racing hearts. But before it could swallow them whole, Brent stepped forward, wrapping an arm around Emmett's shoulders.

"It's okay, Em," he whispered, his voice a beacon of comfort in the storm. "They'll understand. I'm here for you, no matter what."

… And then 2020 came, and with it, the global COVID-19 pandemic.

Schools closed, life went into lockdown, and they had to be separated for months. But Brent mailed Emmett that same worn baseball cap in a taped-up box. Little Emmett held it to his face, inhaling the faded scent of sweat and grass—Brent's scent—as he reread the scribbled note: "Still my dude. Wear this til I see you again".

That night, Emmett slept with it clutched to his chest, the fabric a tangible lifeline to the boy who saw him before anyone else did.

When restrictions eased the following year, Emmett, 13, wore the cap to their first backyard reunion. 14-year-old Brent's eyes lit up—a silent, fierce pride—before he tackled Emmett into a hug that smelled of sunshine and home. No words were needed. The cap stayed, faded and frayed, a crown of belonging.

Back to the present, and Emmett reaches his hand over the edge of the bed and begins searching for something in the drawer as Brent looks on with confusion. "What are you looking for, Emmett?" the jock asked.

Emmett's hand emerged from the drawer clutching the worn-out cap, his eyes glistening with unshed tears. He held it up to Brent, the fabric a testament to the years of friendship and acceptance it represented. "Remember this?" he whispered with an emotional tone.

Emmett nodded, "It's been with me through everything. It's a reminder of when I first started to feel like... like myself." He handed the cap to Brent, who took it with reverent fingers, his eyes never leaving Emmett's face.

"You've always been you, Em," Brent said, his voice firm and resolute. "And I've always been here for you. No matter what."

With a gentle smile, Brent took the cap and carefully placed it on Emmett's head, the fabric now snug against the teenager's grown-up features. It barely fit, a reminder of the years that had passed and the journey they had both shared. The symbolic gesture brought a sense of warmth and belonging back into the room, dispelling the shadows of doubt and fear that had threatened to consume them. Emmett's eyes shone with gratitude as he looked up at Brent, the cap feeling like a crown of acceptance and love.

"Thank you," he smiled. "You've been there for me through everything. I don't know what I'd do without you."

The 17-year-old jock leaned in, pressing a soft kiss to Emmett's forehead. "You never have to find out," he assured, his arms tightening around his best friend.

"You know," Brent said, his voice thick with emotion as he stroked Emmett's chocolate brown hair, "when we started growing up, and you started looking like... like that," he paused, his gaze lingering on Emmett's face, "I couldn't help but admire how handsome you had become." He took a deep breath, his grip on the cap tightening slightly. "I wanted you all to myself," he admitted, his voice cracking slightly. "But you had your eyes on the wrong guys."

Emmett looked up at the Myers teen, his piercing blue eyes searching for the truth in his athletic friend's gaze. "What do you mean?"

Brent swallowed hard, the words heavy in his mouth. "I didn't dare tell you, Em," he confessed. "I was afraid of losing you as my best friend if you knew how much I wanted you. And then when you started dating those other guys... it killed me to watch you get hurt when they didn't understand you like I did. I didn't know if you'd still be there for me after they turned you down."

The room was silent except for the rhythmic beat of their hearts, echoing like a love song that had been playing in the background of their lives all along. The air was charged with a new understanding, the confession bridging the gap that had grown between them without either of them realizing it.

"But they never saw you for who you truly are," Brent continued, his thumb tracing the line of Emmett's jaw with gentle care. "They never knew the strength, the bravery, the sheer beauty that's in every inch of you." His eyes searched Emmett's, a silent plea for the younger boy to understand. "But I did. And I do."

Emmett's eyes searched Brent's, seeing the raw honesty reflected in the depths of his gaze. "What are you saying?" he asked tentatively, hope blossom in his chest like a delicate flower.

"I'm saying that you've helped me understand that love isn't about what's between someone's legs," Brent replied, his voice firm and sure. "It's about the person inside. And you, Emmett, you're that person. You're the one who makes me laugh, who challenges me, who makes me feel alive." He leaned in closer, his breath a warm caress against Emmett's skin. "I like girls, I like guys, and I love you, no matter what you've got down there."

Their eyes locked, and for a moment, it seemed as if the whole world had stopped spinning. Then, with a soft sigh, Emmett leaned in and pressed his lips to Brent's, the warmth of his friend's acceptance washing over him like a gentle embrace. The kiss grew in intensity, a silent declaration of the love that had been simmering just beneath the surface for years.

Their lips parted with a soft pop, the silence shattered by the unexpected sound of Emmett's stomach growling loudly. Brent pulled back with a chuckle, the tension between them dissipating like mist in the morning sun. "I guess that's one way to end a moment," he quipped, his eyes sparkling with amusement.

"Sorry," The transgender teen mumbled, his cheeks flushing a deep shade of red as he ducked his head. "Guess drinking your cum isn't quite the same as a full meal, huh?" he said with a small laugh, trying to lighten the mood.

Brent grinned, his own face flushing slightly. "Well, it's certainly more filling than I expected," he said, his voice teasing. "But yeah, we should probably get you something to eat before your stomach starts a full-on protest."

They climbed out of bed, the warmth of their confession still lingering in the air as they pulled their clothes back on and slipped into their sneakers. Emmett couldn't help but feel a twinge of bitterness at the thought of Jensen, but Brent's presence was a balm to his bruised soul.

"You know," Emmett began, his voice still shaky with emotion, "I was supposed to go to that diner with Jensen tonight." He took a deep breath, looking up at Brent with hope in his eyes. "But I think you'd be a much better choice of company," he said with a small smile.

Brent's smile grew into a warm grin as he buckled his belt, his eyes never leaving Emmett's hopeful gaze. "Don't you worry, Em," he said, his voice filled with determination. "I'll show you a night you'll never forget."

He leaned in to whisper against Emmett's ear, his breath hot and sweet. "And I promise you, I'll be a hell of a lot better than that transphobic fucker." The fierce protectiveness in his tone sent a thrill through Emmett's body, and he couldn't help but feel a spark of excitement for what the evening had in store.

As they made their way downstairs, hand in hand, the storm outside had passed, leaving behind a gentle patter of rain and a sense of new beginnings.

Brent took Emmett's hand as they stepped out into the cool night, the rain having abated to a gentle patter. The street was dark and quiet, a stark contrast to the tumult of their earlier confrontation.

"So, what do you want to eat?" Emmett asked, trying to keep his voice light.

Brent grinned, his eyes gleaming with excitement. "Everything," he said, pulling Emmett closer. "But mostly, I want to eat whatever you want."

Emmett felt a warmth spread through his chest, a feeling of belonging that he hadn't felt in a long time. "Then let's go get some greasy burgers," he said with a laugh. "Because after what has happened this evening, we both deserve something that'll make us feel alive."

They approach Brent's car and Emmett sits in the passenger's seat and Brent starts up the engine. They then drove off to the diner, excited to have their first date night together as a new couple.

...