Sissy's Delivery Boy Unwraps Her Lingerie Secret

Sissy’s heart fluttered the second the doorbell rang. She’d ordered the usual—extra-large pepperoni with garlic knots—knowing exactly who would bring it. Jake. The same broad-shouldered, square-jawed delivery boy who had been showing up at her apartment three nights a week for the last two months. She told herself it was just a silly crush, but the truth was simpler: she loved the way his eyes always lingered a beat too long when she answered the door in her oversized hoodies.

Tonight she wasn’t wearing a hoodie.

The black lace bra cupped her small, perky breasts perfectly, the matching garter belt cinched tight around her narrow waist. Sheer black stockings clung to her smooth, shaved legs, and the tiny lace panties barely contained her smooth cock and balls, the front already damp from nervous excitement. A short silk robe in deep crimson hung open over everything, the belt barely tied. Her shoulder-length blonde hair was tousled just enough to look freshly fucked. She felt obscene. She felt perfect.

She opened the door.

Jake stood there in his red company polo, the fabric stretched tight across his muscled chest. The pizza box looked small in his large hands. His hazel eyes dropped instantly from her face to the exposed lace and silk, and his mouth actually parted. The tension snapped between them like a live wire.

“Fuck,” he breathed. “You… you always wear that underneath?”

Sissy felt her cheeks burn, but she didn’t close the robe. Instead she let her hips shift, letting the silk slide open another inch. “Only on special nights.”

Jake’s gaze dragged up her thighs, over the garters, across the sheer cups of the bra, and finally back to her painted lips. “You’re so fucking beautiful. I’ve been jerking off thinking about you for months. Every time I drop a pizza here I go home and imagine peeling you out of whatever you’ve got on underneath those baggy clothes.”

The raw honesty in his voice made her clit twitch inside the lace. She’d never been this bold before, but his hunger was infectious. Sissy let the silk robe fall completely open, revealing every expensive, slutty detail.

“Then stop imagining,” she whispered.

Jake stepped inside without another word, kicking the door shut behind him. The pizza box hit the floor. His big hands were on her immediately—rough, calloused palms sliding up the backs of her stockings, tracing the clips of her garters, then higher, cupping the smooth curve of her ass. One thick finger traced the lace seam between her cheeks while his other hand boldly palmed the front of her panties, feeling the hard little cock trapped beneath the silk.

“Goddamn,” he growled against her neck. “You’re already leaking for me, pretty little sissy.”

Sissy moaned, hips jerking into his touch. The word sissy should have embarrassed her. Instead it made her knees weak. She grabbed his belt and yanked him toward the living room, their mouths crashing together in a filthy, open-mouthed kiss. His tongue was aggressive, claiming. She could feel the thick ridge of his cock grinding against her stomach through his jeans.

In the hallway she couldn’t wait any longer. Sissy dropped to her knees on the hardwood, fingers trembling as she opened his fly. Jake’s cock sprang out—thick, veined, and already drooling precum. The head was fat and flushed dark red. She licked her lips, then swallowed him down in one eager motion, gagging herself on the girth.

“Fuuuck, that’s it,” Jake groaned, fisting her blonde hair with both hands. “Suck it like the pretty little sissy slut you are.”

She did. Sloppy, wet, worshipful. Spit ran down her chin and dripped onto her lace bra as she bobbed, hollowing her cheeks, swirling her tongue around the fat head every time she pulled back. Jake’s hips started to thrust, fucking her mouth with shallow strokes while he praised her in a rough, broken voice.

“Such a good cocksucker… look at you on your knees in all that expensive lingerie. Bet you put this on hoping I’d finally snap, didn’t you?”

Sissy whimpered around his cock, nodding as best she could. Her own clitty was throbbing, soaking the front of her panties.

Jake suddenly pulled her off his dick with a wet pop and hauled her to her feet. He spun her around and bent her over the back of the couch in one smooth motion. Sissy gasped as he ripped the delicate lace panties to the side, not even bothering to take them off. Cool air kissed her hole for half a second before she felt the blunt, slick head of his cock pressing against her.

“You want it?” he asked, voice low and dangerous.

“Yes,” she begged. “Please, Jake—fuck me.”

He drove in with one long, brutal thrust.

Sissy cried out, the stretch burning so perfectly. He was thick—thicker than any toy she owned—and he didn’t give her time to adjust. Jake started pounding her immediately, hard, deep strokes that made her stockings slip against the carpet. One of his big hands reached around and wrapped around her silk-covered cock, stroking her in time with every thrust.

“Feel that, baby? Your little clitty’s dripping all over my fingers. Soaking your pretty panties.”

The wet sounds of skin slapping skin filled the apartment. Sissy’s moans grew higher, needier. Jake fucked her like he was angry with how badly he wanted her—relentless, possessive. Then he pulled out, sat down on the couch, and yanked her backward onto his lap.

“Ride me. Reverse. I want to watch that ass bounce.”

Sissy straddled him backward, trembling. She reached back, lined up his cock, and sank down again, taking every inch until her ruined panties were stretched tight around the base of his shaft. The new angle made her whimper. She started bouncing, thighs burning, ass rippling with every descent. Jake’s hands gripped her hips, guiding her faster, harder. He had a perfect view of his thick cock disappearing between her cheeks and the way her lace-covered clitty flopped and leaked against her garter belt with every bounce.

“Fuck, look at you,” he panted. “Such a nasty little sissy. Gonna cum just from getting your ass wrecked?”

She was close. So close. The silk was absolutely drenched now, clinging obscenely to her throbbing cock. Jake reached around again and jerked her fast and rough through the soaked material. The dual sensation—his fat cock spearing her prostate and the slick friction on her clitty—pushed her over.

Sissy came with a broken cry, shooting long, pearly ropes inside the lace. The front of her panties turned translucent, cum soaking through the delicate fabric and dripping onto Jake’s abs.

That sight seemed to snap something in him.

Jake growled, lifted her off his cock, and stood up. He spun her around again and pushed her down onto the couch on her back. Then he straddled her hips, fisting his glistening cock. Three savage strokes later he erupted.

Thick, heavy ropes of cum splattered across Sissy’s lace-covered crotch. He painted her spent clitty and balls with pulse after pulse, glazing the black silk white. Some of it landed on her garter belt and the tops of her stockings. The smell of sex filled the room—salty, musky, obscene.

When he finally finished, Jake was breathing hard. He looked down at the mess he’d made of her expensive lingerie. For a moment his expression softened. He reached down almost tenderly and tucked her softening, sticky clitty back inside the cum-drenched panties, patting the ruined lace gently into place like he was dressing a doll.

“Damn,” he murmured, voice hoarse. “That was… better than I imagined.”

He zipped himself up, ran a hand through his hair, and looked at her one last time—spread out on the couch in her disheveled silk and lace, thighs trembling, crotch absolutely painted with his load. Something flickered across his face. Not quite guilt. Not quite shame. Just the sudden, sobering realization that he had crossed a line he couldn’t uncross.

“Gonna bring you a special order tomorrow night,” he said, forcing a cocky little smirk that didn’t quite reach his eyes. “Same time. Wear something even sluttier.”

Then he grabbed the abandoned pizza box, gave her one last lingering look, and walked out.

The door clicked shut behind him.

Sissy lay there in the sudden silence, chest still heaving, legs splayed, expensive lingerie sticky and cooling against her skin. The afterglow was already fading, replaced by something colder. She stared at the ceiling, feeling the cum slowly soaking through every delicate layer she’d so carefully chosen.

What the hell had she just done?

Her regular delivery boy now knew exactly what she was. And tomorrow night he was coming back for more.

She closed her eyes, but the doubt had already settled deep in her stomach, heavy as the load drying on her ruined panties.