Kevin wiped the sweat from his brow, leaning on the handle of the shovel as he surveyed the shallow trenches he’d dug to redirect water from the foundation. Jordan, his friend’s 16 year old son, stood a few feet away, brushing dirt from his hands and trying to look casual. Kevin could still sense the hesitation in Jordan's movements, the carefulness in his glances.

“Thanks for helping out, man,” Kevin said, stretching his arms. “Couldn’t have done it without you.”

Jordan shrugged, a nervous half-smile on his face. “No problem. It’s… uh, work. I’m good at it.”

Kevin’s mind was already shifting to the conversation he'd been planning. He’d wanted to talk to Jordan for a while, ever since he’d noticed the little tells—the subtle ways Jordan seemed more feminine than he’d admit. “You know,” Kevin began casually as they headed inside, “a lot of people have their suspicions about you. Me included.”

Jordan froze mid-step, a flush creeping up his neck. “I’m… I’m not gay,” he said quickly.

Kevin let out a low chuckle, resting a hand on the kitchen counter. “Relax. I’m not saying you are. Just curious. Do you ever watch… porn?”

Jordan shifted uncomfortably. “Yeah,” he admitted, his voice small.

Kevin leaned against the counter, watching him carefully. “And, when you watch, do you ever feel like you want to be… the girl in the video?”

Jordan shrugged, not meeting his eyes. Kevin sensed the truth in the tiny hesitation, the shrug that spoke volumes. He let the silence stretch. “That’s a yes,” he said softly, a smile tugging at the corner of his mouth.

Jordan’s mouth opened slightly, then closed. He didn’t answer or argue. Kevin could tell the wheels were turning in his head. He moved closer. “Ever thought about what it would be like to be a girl, or to suck another man’s cock?”

Jordan’s throat worked, his Adam’s apple bobbing as he swallowed nervously. No words came out. Kevin grinned inwardly. He’d hit a nerve. This was exactly the reaction he’d hoped for.

“You don’t have to answer,” Kevin said, letting his voice drop lower and rougher, “just… think about it.” He could feel his own arousal building, the thought of coaxing this tight, reluctant teenager into obedience making him swell in his jeans. Kevin’s hand drifted casually toward his waistband, tugging at it just enough for Jordan to notice. The moment hung heavy and tense. Jordan shifted his weight, caught between instinct and curiosity, a mix of fear and desire in his eyes.

"Do you ever go into your sister's room and look at any of her clothing?"

Jordan looked at him as if he had just been caught.

"So you have," Kevin said. "Did you just look, or have you tried some of it on also?"

Jordan didn't or couldn't say a word.

"Answer me," Kevin said firmly. "Have you put on your sister's panties, or one of her bras?"

Jordan, still looking at the floor, whispered, "Yes."

"Was it her panties? Her bra? Maybe both?" he asked in quick follow-up.

"Both," Jordan uttered barely audibly.

"Did you like how they felt when you put them on? Did it make you feel like the girl that you wish to be deep down inside?"

Jordan just nodded, yes.

"You could be a cute girl, Jordan. Your little butt would be perfect in a cute pair of panties! Tell you what, come with me."

Jordan followed him to a spare bedroom. Kevin opened a few drawers and shuffled through them. "Here, put these on," he said, handing him a baby blue thong. Kevin shuffled more things in the drawer and held up a bra. "No, that's too big for you." Opening a different drawer, Kevin pulled out a different bra. "Here, this should fit."

"I will be right back, and when I come back, I want you wearing nothing but those panties and that bra." Jordan started to say something, but Kevin cut him off. "Just do it. I'll be back in a couple of minutes."

Kevin left the room, and Jordan slowly and reluctantly got undressed. He started with the bra first, struggling to get it on, his hands shaking like a leaf in a strong wind. He finally got it on and positioned as it should be.

He picked up the thong but didn't like it. He looked through the drawers and found a light yellow pair of cotton panties and slipped into them. With a little adjustment, he got everything packed into them.

Kevin came back into the room and was pleasantly surprised that Jordan had not only put on the bra and panties, but had also picked out a pair of panties he preferred.

"Do you feel pretty, Jordan?"

Jordan nodded.

"Do you feel like a cute little girl?"

Jordan nodded again.

"Good. That's very good, Jordan. Now, I think we should take the next step. Now that you are dressed like a girl, and you feel like a girl, I think you should do some things that girls do."

Kevin stepped up in front of him. "Get down on your knees, Jordan." With just a split second of hesitation, Jordan did as he was told.

"Now pull my shorts down." Jordan reached up, hooked his thumbs inside the band, and pulled Kevin's shorts down past his knees.

Kevin's partially hard member was hanging low and growing.

Kevin’s inner voice whispered, Okay, let’s see if he’s ready. He watched Jordan swallow nervously, lips parted slightly, eyes darting up and down Kevin’s body. Kevin leaned closer, letting the head of his cock brush against Jordan’s lips.

“Open up,” Kevin said, keeping his tone gentle but firm. “No hands yet. Just… your mouth.”

Jordan’s lips hesitated, brushing the tip before pulling back. Kevin let out a low sigh, more to himself than to Jordan. “Breathe,” he instructed. “Slow. Deep. Steady your nerves. You can do this.”

Jordan took a shaky breath, closing his eyes. Kevin’s cock pressed against his mouth again, and this time, he opened wider, letting the head slip in. The movement was mechanical at first, clumsy and uneven. Kevin’s mind raced, half-frustrated, half-amused. Patience… let him learn.

He guided Jordan, whispering, coaxing, “Relax your jaw… just a little deeper… good, that’s it.” Kevin's cock continued to grow, watching Jordan’s tentative attempts gradually grow more natural. Jordan's lips tightened and loosened rhythmically, taking more of him with each pass. Kevin’s thoughts wandered, dark and lustful. "This is exactly how I imagined it, Jordan. You are such a good little girl." 

Jordan leaned further forward, each time taking Kevin in deeper, no hands, just working Kevin's cock with his mouth. The wet sounds, the slight gag now and then, but also the low, eager sighs that told him Jordan was a natural. 

Now that he was fully erect, Kevin stepped back and asked Jordan if they should try the next step. Jordan just shrugged his shoulders. "I think we should give it a try, ok?" 

He helped Jordan to his feet and ran his hand over the cute little bra Jordan was wearing. The sheer lace felt delicate beneath Kevin's touch. With his other hand, Kevin rubbed Jordan's little butt cheeks through the thin, silky fabric of his panties.

"Did you enjoy that, you little girl?" Kevin murmured, his voice low and possessive, his fingers tracing the soft seam where the silk met Jordan's skin.

Kevin leaned in closer, his breath warm against Jordan's ear. "I think we should take the next step," he whispered, his hands steadying Jordan's butt cheeks.

Jordan shook his head, looking uncertain. "I've never done that before," he admitted, his voice barely a squeak.

Kevin chuckled softly, tilting Jordan's chin up until their eyes met. "You never had anything in your mouth until now, right? And look how much you loved that," Kevin replied, his eyes gleaming with playful encouragement. "So let's give it a try. I promise I'll be gentle."

Kevin gave Jordan's hip a reassuring squeeze, waiting for Jordan's nerves to settle, his gaze never leaving Jordan's face.

Jordan managed a small, hesitant "Okay." He then asked Kevin how he wanted him to position himself.

Kevin's instructions were simple and direct. "Get onto the bed, on your hands and knees, facing away from me."

Jordan did as he was told, crawling onto the soft mattress until his small butt was presented perfectly to Kevin. Kevin knelt behind him, his movements slow and deliberate. He gently slipped Jordan's panties off his little butt and down his legs, easing the thin fabric over his ankles and then off completely, leaving Jordan naked and exposed in the vulnerable position.

Kevin squeezed a generous amount of lube onto his hand and slicked up a finger. He slowly began to slip it inside of Jordan's little butthole. Jordan gasped, his muscles clenching tightly around the intrusion. It was distinctly uncomfortable and tight in the beginning, and he instinctively started to pull away.

"Relax, sweetie. Just breathe," Kevin murmured, keeping the pressure steady but gentle. He waited, letting the soft tissue stretch and relax around his digit. After some time, the initial discomfort subsided, replaced by a deep, foreign pressure that was starting to feel intriguing.

When Jordan's whimpers turned into soft moans, Kevin added more lube. He then pressed a second finger against his little brown butthole. Jordan braced himself, but the slickness of the lube and the existing stretch allowed the second finger to make its way inside, following the first. Jordan’s hips lifted slightly as he adjusted to the new fullness, a definite thrill mixing with the stretching sensation.

"Jordan," Kevin asked, his voice low and serious, "Should we try my cock next?"

Jordan twisted his neck, looking back over his shoulder at Kevin, his eyes wide and trusting. He was flushed and trembling slightly, but his hips stayed obediently in position. "Please go slow," Jordan told him, the plea soft but clear.

Kevin smiled warmly, appreciating Jordan's trust. He pulled a hand from Jordan's butt, squeezed more lube onto his erection, and aligned himself behind Jordan. He pressed the thick head of his cock against Jordan's well-lubricated exit hole, applying slow, steady pressure.

Jordan gasped, his body tensing, feeling the significant difference between Kevin's thick cock and his fingers. Kevin paused, letting the stretched tissue acclimatize, murmuring encouragement and rubbing a hand over Jordan's tight little butt cheeks. He waited until Jordan let out a soft, involuntary moan of mixed discomfort and anticipation, signaling he was ready for more.

With a deep breath, Kevin began to push, gliding slowly forward, inch by careful inch, until the head of his cock finally slipped past the final barrier and fully into Jordan's tight little ass.

Kevin held Jordan's hips tight, his large hands anchoring him in place. He began to move with the utmost care, slowly guiding his cock in and out of Jordan's boy pussy. The friction was intense, a deep, full feeling that was entirely new to Jordan.

Jordan gasped, his knuckles white as he braced himself against the mattress, the slow, rhythmic pressure stretching him completely. The fullness felt shocking, a complete invasion, yet undeniably exhilarating. He let out a series of small, broken moans, the sounds of combined pain and pleasure filling the air.

Kevin watched Jordan's reaction closely, his eyes dark with focused desire. He pulled out almost entirely, then eased back in, repeating the slow, deliberate stroke. "How does that feel, Jordan? Is it too much?" he whispered, his breath hot against Jordan's neck.

Jordan shook his head slightly, unable to form a full word, but the motion was enough. It was a lot, but it wasn't too much. It was terrifyingly, wonderfully new.

Kevin began to slowly pick up the pace, turning the gentle exploration into a real and proper butt fucking. He eased into a steady, rhythmic thrusting, pulling out far enough to stretch Kevin, now driving deep, finding the internal pressure points that made Jordan whimper. The wet, slapping sounds of skin colliding filled their ears, a potent rhythm of their shared moment.

Jordan's eyes squeezed shut. He knew, intellectually, that this felt wrong—a complete transgression of the limits he once held. Yet, he couldn't help but feel how utterly right it was. Every deep stroke, every powerful invasion of his asshole, felt like a vital step in his transformation. His place in becoming a real girl was being forged in this intense, painful, wonderful act. Only girls suck cock, right? he thought, recalling the passion of the previous act. Only girls let a man fuck them, right?

His breathing was deep and ragged, and a thrilling, seismic change was taking place in his body. The pressure, the fullness, the complete surrendering of his hips—it all dissolved the last vestiges of his male identity, replacing it with the submissive, receiving pleasure he desperately craved. He wasn't just being used; he was being made into what he longed to be.

Kevin's pace was now quick and relentless, hammering into Jordan's tight bottom with powerful, focused strokes. Jordan gritted his teeth, unsure how much longer he could last, but he was determined, doing his best to meet every drive and absorb the constant pounding.

Jordan twisted his head back and asked for more lube, his voice strained. Kevin readily obliged, pausing only long enough to slick the outside of his cock and Jordan's asshole, ensuring the relentless action could continue without interruption. He resumed his piston-like driving, his eyes fixed on Jordan's arching back and trembling thighs. Kevin was fully committed now, determined to give Jordan his first load deep inside of his ass, marking him completely and sealing this transformative experience with his warm, thick semen.

Kevin was now overwhelmingly close. He reached up and grabbed the fine hair he could get on the back of Jordan's head, pulling his head back to intensify the position. His pace instantly became faster and harder, his breathing ragged as he surged toward climax.

"Fuck, Jordan, you are doing so good, I'm, I am, oh god," Kevin strained, his words thick with building pleasure.

Then, with a powerful final effort, Kevin pulled Jordan back tight against him, his hips flexing forward and driving his cock as deep into Jordan as he could. He began to cum. Shot after shot of hot, thick semen flew out of the end of his cock, pumping deep into Jordan's ass.

It was at this moment, as the searing heat of Kevin's cum flooded his insides. A profound, warm wave began to flow through Jordan's entire body. Jordan didn't know it yet, but that wave—the intoxicating mix of completion, submission, and seminal fluid—would change him forever.