A Sissy’s Slip-Up (1/2)

The follow-up will be released next Friday!

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Liam barely heard his girlfriend, Emma, as she kissed him goodbye before heading out on her business trip. He nodded along absentmindedly as she mentioned her brother, Jake, might stop by to crash at their place, but he was too distracted by the thrill bubbling inside him. The moment the door shut behind her, he wasted no time. He was free. For days.

The first thing he did was head straight to her closet. Silks, lace, tight little skirts—he could already picture himself wrapped up in all of it. His hands trembled with excitement as he sifted through her clothes, carefully selecting the perfect ensemble. Over the next few days, he indulged in his secret fantasy fully. Each morning, he spent hours getting ready, slipping into delicate lingerie, zipping himself into dresses that clung to his frame, and perfecting his makeup until his features were soft, feminine, and utterly convincing.

By the time the fourth day rolled around, he had outdone himself. His long, blonde wig cascaded down his back in soft waves, perfectly styled to frame his face. His makeup was flawless—dramatic lashes fluttering over smoky, sultry eyes, sharp brows, and lips painted a glossy shade of pink. A slinky black dress hugged every curve, the short hemline leaving his smooth, shaved thighs exposed above a pair of sheer thigh-high stockings, their lacy tops peeking out just enough to be tantalizing. Strappy heels accentuated his toned legs, and his long, press-on nails clicked against his phone screen as he posed for yet another round of selfies, angling himself just right to capture the perfect shot. He was utterly lost in the way his movements had become so effortlessly feminine, the way the soft fabric of his stockings clung to his legs, the way the heels shifted his posture into something undeniably alluring. It was intoxicating, living like this.

So intoxicating, in fact, that he didn’t even notice the door open—until a deep voice cut through his blissful haze.

“Hey. Who are you?”

Liam froze, his stomach twisting as he spun around. Jake stood in the doorway, duffel bag slung over his shoulder, his sharp eyes locked onto him with mild confusion.

“Oh! I’m, um… a friend of Emma’s,” Liam answered quickly, forcing his voice into its sweetest, most feminine tone as he straightened his posture, delicately crossing his legs.

A slow smirk curled at Jake’s lips as he stepped inside, shutting the door behind him. His gaze dragged over him shamelessly, lingering on his legs, his cinched waist, the way the thin straps of his dress barely concealed the soft curves of his chest. He sank onto the couch with an amused hum, stretching out lazily. “You got a boyfriend?” he asked, his voice dipping lower.

Liam’s breath hitched. “N-no.”

A slow, knowing grin spread across Jake’s face. “That’s a shame. A girl like you shouldn’t be alone.”

The tension in the room thickened as Jake leaned forward, his fingers grazing Liam’s exposed thigh. The touch sent a jolt through him, his stomach twisting into a tight knot of nerves. “You’re blushing,” Jake murmured, his grip tightening ever so slightly. “What’s wrong, sweetheart? Never had a man tell you how sexy you are?”

Liam opened his mouth to protest, but the words died in his throat as Jake’s hand drifted lower—over the soft curve of his stocking-clad thigh, past the lacy hem, until his fingers brushed against his tucked-away penis.

Liam let out a high-pitched yelp, his body jolting as he gasped, “I-I’m not a girl!”

Jake pulled back slightly, a slow smirk creeping across his lips. He leaned back against the couch, crossing his arms as he watched Liam squirm. “Now this is interesting,” he mused, clearly enjoying himself. “Emma’s little boyfriend, prancing around in stockings and heels, looking like a total sissy.” He let the word hang between them, savoring the way Liam’s face burned with humiliation. “She’d love to hear about this, don’t you think?”

“Please, Jake—she can’t know,” Liam begged, desperation weaving through his voice like a taut thread about to snap.

Jake’s smirk widened into something wicked, his eyes dark as he drawled, “I guess I could keep quiet, but...” His hand casually undid the button of his pants, slow and deliberate. “…I’m gonna need something in return.”

The fabric fell away, and his cock sprang free—thick, pulsing, commanding attention. Liam's eyes widened as he took in the sight, the sheer size making his heart race. A moment of hesitation gripped him, but the thought of Emma finding out spurred him onward.

Slowly, Liam sank to his knees, his position bringing him eye-level with Jake’s cock. Up close, it seemed to twitch with expectation, the heat emanating from it a palpable force. His lips, still glossy with that perfect shade of pink, brushed the tip with reverence before parting to envelop it.

The world seemed to narrow to the weight of Jake’s cock in his mouth, the way it stretched his lips, the salty tang as he swallowed it deeper still. He bobbed on it, his motions hesitant at first, then growing in confidence, a new rhythm taking hold. Each glide pushed the boundaries of what he thought himself capable of, taking Jake further, deeper. His own body thrummed with unexpected pleasure, the knowledge of what he was doing, who he was becoming, a wicked thrill.

Liam told himself this was just to keep Emma from finding out, to preserve his secret. But with every stroke, every low groan Jake whispered, he worried—no, feared—he might be enjoying it far too much.

But still, he didn’t stop.