Caught! Ch. 01

I have been reading stories on here for years and have finally got around to writing one of my own. This is my first attempt at writing fiction, so any comments or suggestions would be great! I hope you enjoy!

(All characters are over the age of 18.)

Jamie and Katie looked good together -- on paper.

People said it all the time. At dinner parties. At weddings. At her sister's baby shower. You two are perfect. You balance each other. She's fire, you're calm. Yin and yang. Jamie had smiled through those comments, nodded, even laughed a little, as if he believed it too.

But the truth was never that simple.

Katie was striking -- tall, with long, impossibly toned legs that seemed built for heels and attention. She moved like she owned the space around her. Confident without trying, effortless in a way that made heads turn. Even in sweatpants, she had that kind of cool composure people envied. The kind that made men stop mid-sentence. Not just any men -- men. The kind who walked like they belonged in cologne ads. Broad shoulders, easy laughs, firm handshakes. They looked at her like she was something they deserved. And sometimes -- sometimes -- she looked back.

Jamie noticed. Of course he noticed. He wasn't like them. Not even close. He was quiet. Thin in a soft, unremarkable way. He had a kind face, people said. Gentle hands. His shirts were always buttoned too carefully, his hair always in place. He measured his words like they might explode if handled wrong. He moved like he was always apologizing for being in the room. He wasn't short, but he never filled a space. Not like Katie did.

She used to tell him that was part of his charm. "You're not like other guys," she'd said once, resting her head on his chest. "You're gentle. You actually listen."

But she never said that after sex. Not once. Because the sex was never good. Not from the start.

Jamie had tried. God, he'd tried. He did everything he thought he was supposed to -- touched her the right way, said the right things, kissed when he should have kissed, moved when he was supposed to move. But something always felt off. Like he was performing. Like he was acting out a role he'd learned by watching other men.

He never felt the spark he was supposed to feel. No hunger. No urgency. Just pressure. Expectation. Like being a man meant he was supposed to want this, supposed to take her, supposed to love the way she moaned his name. But deep down, it always felt like he was imitating someone else. Someone she deserved.

He never told her that. Not really.

Instead, he faked confidence. Faked drive. Faked pleasure. He got hard sometimes, just enough to pass, just enough to go through the motions, but it never lasted. She didn't ask at first. But over time, the questions crept in.

"Is it me?"

"Are you not attracted to me?"

"Is it stress?"

He never had a good answer. Just apologies. Excuses. Another attempt that ended in silence.

Eventually, she stopped asking. And when she rolled away from him without a word, night after night, he stared at the ceiling and wondered if she already knew. If she had always known.

Her mornings were routine. Office job downtown. Gone by 8:15 sharp. No kiss goodbye. No small talk. Just the sound of her heels tapping across the hardwood and the soft click of the door closing behind her.

Jamie's schedule rotated -- odd shifts, short days, long nights. But days like today were wide open. Long and quiet. Once, they had felt lonely. Now... they felt like air.

When he heard her car pull away, he waited. Counted five minutes. Then five more. Just in case. Then -- finally -- he moved.

He went to the front door to check that it was locked. Then checked it again. Twist. Rattle. Twist again. He needed to know it was sealed.

Curtains next -- drawn carefully, deliberately. Living room. Kitchen. Bedroom. He moved through the apartment like someone sweeping for mines. He wasn't rushing. Every step had a rhythm. Every click of a curtain felt like a lock sliding into place. Securing him. Protecting something fragile.

His phone buzzed once -- a text maybe -- but he turned it facedown and powered it off. He didn't need noise. Or questions. Or the feeling of being watched. Not today.

He walked into the bedroom barefoot. The air was cool on his skin, brushing across his arms, his chest, his legs. He knelt at the closet and reached behind the coats and scarves that smelled faintly of dust and dry-cleaner plastic. A duffel bag lay hidden in the far back corner, wedged between shoeboxes and an old electric blanket. He dragged it out slowly, quietly, like he was afraid the sound might carry. Unzipping it was like cracking open a secret life.

Inside: a pink bra, delicate and worn. Matching lace panties. Neon fishnet stockings. A garter belt with silver clips. Four-inch nude stilettos. It wasn't much. Just the bare essentials. But it was all he had left.

Jamie used to have more -- A dress here and there, soft and clingy, bought online late at night and hidden under his bed. Later, a pair of heels -- black, three inches, the kind that clicked loud enough to make his heart race just wearing them alone in the kitchen. At one point, he had a set of delicate lingerie -- lace and sheer, pale blue, worn until the elastic gave out. And then, makeup: a tube of lip gloss tucked in his jacket pocket, mascara he only applied in the safety of locked doors. They came and went at different times in his life, small indulgences he always thought he could live without -- until he couldn't.

But they were all gone now. Purged. Tossed. Burned with shame.

It had happened before -- more than once. He'd wake up in a cold sweat, disgusted with himself. Stuff everything into trash bags, drive to some far-off dumpster at night, and swear he was done. He'd feel powerful in those moments. Like he was taking control. Like he was killing off some broken, perverse part of himself.

But the peace never lasted. The guilt turned hollow. The confidence cracked. And within weeks, sometimes days, the hunger would come back. The ache. The need. And so would the clothes -- bit by bit, piece by piece. Bought in secret. Stuffed into bags at the bottom of drawers. Each new purchase was like a whispered promise to himself: just one more time. He knew he'd always come back to this. Because when he opened the bag, when he touched the fabric -- something in him unlocked.

He laid the clothes out on the bed slowly, smoothing the wrinkles from each piece like they were precious.

He started with the bra. It was light pink, soft, worn down at the edges. No padding, just two gentle cups that flattened him a little and hugged his ribs tightly. He slid it on, reaching behind with practiced fingers to clip the clasp. It wasn't comfortable in the traditional sense -- but it felt right. It cinched his chest in just enough to take the shape away, to make him look... less like a man. The pressure of the band made him feel held, supported. Smaller.

He exhaled through his nose.

Then the panties. Matching lace. They clung to his hips and cupped around his tucked cock in a way that was snug but not tight. There was resistance -- his body still awkward beneath the softness -- but there was something beautiful in the discomfort. It made him aware of his body. Every breath, every shift of fabric, reminded him he was becoming.

The fishnets came next. He sat on the edge of the bed and rolled them up his legs, inch by inch. The mesh slid over his skin with a whispering rasp, catching slightly on his knees, stretching over the curve of his calves. His legs were smooth -- he'd shaved last night, slow and thorough. There was something about the ritual that calmed him. Something about the slickness of bare skin against lace that made his chest flutter.

He clipped the garter belt into place last, adjusting the straps until they sat just right against his thighs. When he stood and looked down at himself, he saw a silhouette that didn't look like a man trying to be something else. It looked like someone real. Someone closer to the truth.

The heels were the final step.

He slipped into them carefully, one foot at a time. The arch of the shoes forced his hips to tilt forward, his lower back to curve. He stood slower than he used to -- more controlled, more graceful. His balance shifted instinctively. He adjusted, one hand on the bedframe, and then stood tall.

Everything about him changed with the heels on. His walk became quieter. Measured. His hips swayed with every step -- not exaggerated, just natural. Organic. Like his body had been waiting for an excuse to move this way. His posture softened. Shoulders relaxed. Chin tilted down just a bit. He didn't walk like Jamie now. Not the Jamie people saw. He walked like her. Like the version of himself that didn't live in shame. The version that didn't need to explain.

He could feel it.

He could feel it in the way the stockings hugged his legs. In the quiet click of each step across the hardwood. In the warmth of the lace between his thighs. In the way the bra pressed into his chest like an embrace.

There was a softness blooming in him. A sense of rightness he couldn't get anywhere else. Not from praise. Not from sex. Not from being someone's boyfriend.

Standing in front of the bedroom mirror, Jamie paused. His heart pounded slowly, deliberately. He shifted his weight gently from one heel to the other, feeling the way his hips naturally settled into the gentle sway that the stilettos demanded of him. He tilted his head slightly, lips parted as he studied himself through half-lowered lashes.

The delicate lace felt softer now, warm against his skin, hugging every subtle curve and shadow of his slender form. He allowed his fingertips to trace the delicate edges of the bra, lingering there, appreciating its gentle constriction, the illusion of softness, of femininity, it gave him. His gaze dropped lower, watching the gentle rise and fall of his chest with each shallow breath, imagining how he might look to someone else, someone stronger, someone who knew exactly what they wanted.

A thrill danced up his spine, soft and electric.

Slowly, he turned away from the mirror, allowing himself the indulgence of a slow, measured walk across the apartment, heels clicking softly against the polished hardwood. Each step echoed quietly, carrying him forward like music. There was power in these subtle movements -- not the aggressive, overt power he saw other men claim so easily, but something quieter, more internal, more genuine. Each careful sway of his hips spoke of a truth he'd spent years burying, but now embraced with quiet courage.

Jamie's fingertips drifted absently along the surfaces he passed -- the edge of the dresser, the smooth wood of the kitchen countertop, the plush texture of the sofa's armrest. He savoured these sensations, letting the soft friction ground him, anchor him deeper into the moment. Everything around him was heightened, brighter, clearer -- every nerve awake, every sensation amplified by the simple truth of finally being honest with himself, if only for a few precious hours.

In the kitchen, he opened the fridge to retrieve a small bottle of sparkling water, aware of the gentle shiver that passed through him as the chilled air brushed against his lace-covered skin. He smiled softly to himself, delighting in the goosebumps that rose on his exposed thighs, the delicious contrast of cold air and warmth of his own body.

He sipped slowly, delicately, lips pursed around the rim of the bottle in a way that felt instinctively feminine, authentically his. He moved back to the living room, taking his time, savouring the quiet, deliberate clicks of his heels against the floor, letting that sound anchor him, reassure him that right now, in this moment, he was fully, beautifully himself.

Settling onto the couch with practiced grace, Jamie crossed one leg smoothly over the other, the fishnets whispering gently against each other with the soft friction. He adjusted the lace against his hips, fingertips tracing the contours of his thighs with gentle reverence.

He felt beautiful. He felt desired -- even if only by himself. He felt, finally, like the woman he always dreamed he could be.

With a soft exhale, body relaxed into the couch cushions, he reached slowly for the laptop, heart fluttering in quiet anticipation.

His fingers were trembling as the screen illuminated his flushed face in shades of pale blue. His breath quickened, pulse pounding in his ears as he typed into the browser's search bar, hands shaking slightly:

"older man dominates younger feminine crossdresser."

The results filled the screen instantly, explicit thumbnails promising exactly what he craved. He scanned quickly, breathing shallowly, until a particular video seized his attention:

"Daddy Takes Care of His Girl."

The thumbnail alone sent heat coursing through his veins -- an older man, strong, confident, broad-shouldered, with a silver-streaked beard and a powerful, commanding gaze, gripping the slim, delicate waist of his younger partner. The younger figure, beautifully feminine, dressed in pink lingerie, sheer stockings hugging smooth thighs, looked upward with wide, submissive eyes framed by perfectly applied makeup. Jamie's stomach clenched with longing as he clicked play.

The scene began gently, intimately. The older man's voice was deep, reassuring, yet commanding. Jamie felt a shiver race down his spine as he watched the younger partner submit gracefully, willingly, head tilted softly, eyelashes lowered submissively.

Jamie's heart pounded harder, his cheeks flushing as desire bloomed between his thighs. His mind raced ahead of the video, imagining himself in that younger figure's place -- soft, vulnerable yet safe, dressed elegantly in lingerie, makeup flawless, body smooth and desirable, surrendering completely to the powerful embrace of an older, authoritative lover.

God, how badly he wanted that.

Jamie reached down beside him on the couch, picking up the small bottle of lube and his silicone dildo. He uncapped the bottle, squeezing a generous amount onto his fingertips. Gently pushing aside the delicate lace panties, he reached behind himself, his breathing growing deeper and more unsteady as he pressed a slick fingertip against his entrance.

He inhaled sharply at the cool sensation, eyes fluttering closed briefly as he slowly eased his finger inside, breath catching at the tight warmth enveloping him. Carefully, he moved deeper, stretching gently, feeling his muscles relax and open for him. His breathing quickened as he slid another finger inside, gasping quietly as the sharp pleasure mingled with that delicious ache.

On-screen, the older man had positioned the young crossdresser face-down on the bed, powerful hands caressing delicate skin before slowly, tenderly entering him from behind. Jamie matched their rhythm instinctively, fingers pressing deeper, imagining himself beneath the older man, feeling those strong, authoritative hands gripping his hips firmly.

"Please," Jamie whispered breathlessly, eyes glazed, hips shifting eagerly into his own touch. "God... please..."

He withdrew his fingers carefully, body now eager, needy, craving more. Jamie quickly lubed the dildo, coating it generously before pressing it gently against himself. He trembled softly, drawing in a slow, unsteady breath as the firm tip slowly pressed inside, deeper, fuller, stretching him in exactly the way he needed. A soft, feminine moan escaped his lips -- his voice higher, breathier, the way he imagined himself in that younger partner's place.

Jamie rocked his hips slowly at first, matching the powerful, rhythmic thrusts onscreen. He couldn't take his eyes off the older man -- so masculine, broad-chested, silver-bearded, confident hands guiding, dominating, yet tender. Jamie's thighs trembled beneath the sheer stockings as pleasure spiralled through him, his fantasies vivid and aching. He imagined those strong, protective arms around him, the older man's lips brushing his ear, whispering praise as he surrendered himself completely.

He moved the dildo deeper, faster, hips rising urgently, breath hitching softly with every thrust. The sensation overwhelmed him, sharp and intoxicating, each movement driving pleasure deeper until his vision blurred with intensity.

Finally, heat surged violently, overwhelming him. Jamie cried out sharply, voice breaking into a helpless, feminine moan as his body arched off the couch. Waves of intense pleasure cascaded through him, exploding beautifully beneath the tight lace. His thighs shook uncontrollably, body trembling through a massive, shattering climax.

He collapsed back onto the couch, breathing raggedly, chest rising and falling beneath the delicate bra, mind spinning, body warm and spent --

And then suddenly, the sharp metallic scrape of a key sliding into the apartment lock shattered the silence.

Jamie bolted upright, every muscle instantly rigid, panic surging through him like a jolt of electricity. His heart slammed violently against his ribs, stomach twisting into a sickening knot. His eyes darted wildly around the room -- the open laptop, the explicit video still playing softly, the dildo slick with lube lying exposed on the couch beside him, the unmistakable lingerie hugging his trembling body.

"No, no, no," he whispered desperately, fumbling helplessly, paralysed between the need to hide and the overwhelming terror freezing him in place.

The lock clicked loudly, door swinging open abruptly.

Katie stood frozen in the doorway, eyes wide, mouth falling open, shock and disbelief etched plainly across her face.

"What the actual fuck?"

Katie stood frozen in the doorway, mouth agape, eyes wide and cold, disbelief twisting rapidly into revulsion. Jamie felt his entire body flush violently, heat burning through his cheeks, neck, and chest. Panic flooded his veins, his heart thundering wildly in his chest. He reached frantically for the nearest pillow, desperately scrambling to cover himself, the dildo slipping from his grasp and rolling onto the floor with a sickening, humiliating thud.

"Katie -- fuck -- I -- I can explain. " Jamie stammered, voice cracking painfully, hands shaking uncontrollably.

"Oh my God," Katie whispered, voice edged with a disgust so visceral it hit Jamie like a punch. "Oh my fucking God. Jamie, what the hell?"

She stepped further into the room, eyes scanning him from head to toe, lingering pointedly on the pink lace bra and fishnet stockings hugging his trembling body. The laptop still played in the background, low, obscene moans filling the silence.

Jamie lunged desperately to slam it shut, nearly dropping it in the process, hands clammy and useless with panic. He couldn't breathe, couldn't think, couldn't even meet her gaze.

"Is this why you can't fuck me, Jamie?" Katie hissed venomously, voice rising sharply. "Because you'd rather pretend to be some perverted fucking fairy?"

Jamie recoiled, humiliation twisting in his gut, face flaming red. He felt tears sting at the corners of his eyes, blurring his vision. "Katie, please -- no -- it's not like that -- I swear."

"Oh, shut the fuck up," she snapped. "Look at you. Sitting here dressed like a fucking faggot, jerking off to gay porn? Jesus Christ. I thought maybe you were stressed or depressed, but you're just fucking twisted."

Jamie's heart pounded so violently he felt sick. Panic clawed at his throat, choking off his breath, his mind spinning desperately. His body trembled, skin prickling hotly with shame. He couldn't move, couldn't speak, trapped beneath her disgusted glare.

"It -- it isn't gay, Katie," Jamie stammered pathetically, hating himself even as the words left his lips. "I was just... curious... experimenting..."

Katie laughed harshly, cruel and humourless. "Experimenting? You're wearing lingerie, Jamie. Fucking lingerie. You've got heels on, and I just watched you shove that thing up your ass. Don't stand there and lie to my face."

Jamie shook his head desperately, throat tightening, tears threatening to spill down his burning cheeks. "No -- I'm not -- I swear, Katie. Please believe me."

She stepped closer, eyes narrowed dangerously, voice low and cutting. "Why the fuck should I believe you? You couldn't get it up for me if your life depended on it, but apparently cross-dressing and gay porn do it for you. Sandra warned me about you from day one -- said something was off, said you were probably a closet fag. God, I should have listened to her."

Jamie's stomach twisted painfully, humiliation so intense he felt like vomiting. The thought of Sandra, Katie's best friend, knowing this secret, of her smugly telling Katie that he was somehow broken, made him dizzy with shame. His pulse roared in his ears, panic blurring his vision.

"Katie, please." Jamie whispered hoarsely, voice cracking as shame poured through him in waves. "Please. I'm begging you -- I'll do anything -- just please don't tell anyone about this."

Katie's lip curled into a vicious smirk, eyes cold and cruel. "Why? Afraid everyone will know what a pathetic, dickless sissy you are? Afraid everyone will realise you couldn't satisfy me because deep down, you'd rather get fucked by some guy?"

Jamie shuddered visibly, tears finally slipping helplessly down his flushed cheeks, breath ragged and uneven. He wanted to sink into the floor, to vanish completely. He'd never felt so exposed, so utterly helpless and worthless.

Katie shook her head slowly, disgusted pity on her face. "God, look at you -- such a little bitch. You're fucking pathetic, Jamie. What did you think, that you could dress up and pretend you weren't some useless faggot and nobody would ever find out?"

Jamie flinched with each slur, his throat closing, panic rising unbearably. He was shaking now, openly sobbing, feeling utterly stripped bare beneath her scornful gaze. "Please... Katie... please just stop... let's talk about this."

"Oh, grow up," she snapped, voice dripping venom. "You've lied to me this whole time. You've humiliated me. All this time, making me feel inadequate -- like I was the problem -- when really, it was you. God, you're disgusting."

She turned sharply, heels clicking loudly against the hardwood as she stalked angrily toward the door, pausing once more to look back at him, eyes narrowed. "You know what, Jamie? Clearly, pussy doesn't do it for you. So next time, spare some poor girl and just find yourself a fucking boyfriend. At least then you won't have to lie."

"Katie -- wait, please -- " Jamie choked out desperately, voice thick with tears, panic gripping his heart so tightly he thought it might burst. "Please don't leave like this. Don't -- please don't tell anyone -- "

She gave him one last, scathing look, voice dripping with disgust. "Pathetic."

The door slammed behind her, echoing like a gunshot through the empty apartment, leaving Jamie trembling violently, heart racing, stomach twisted painfully.

He sank down onto the floor, the delicate lace now feeling like a cruel, mocking prison around his shaking body. What the fuck was he going to do?