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Pizza Delivery Surprise

Pizza delivery guy gets flashed by skinny customer.

8 min read October 27, 2026New

Warrick had watched the videos for months. Not the usual kind, not the produced studio stuff with lighting and scripts. The amateur ones. Girls in apartments, still damp from a shower, a little white towel tucked under their arms, opening the door to some guy holding a pizza box. The drop. The look on the deliveryman’s face. The way some of the girls bit their lip and just stood there, letting him see everything.

He was twenty-eight. Five-foot-four. Skinny in a way that never filled out no matter how many late-night slices he ate. He had ordered from the same place so many times that he knew which nights Harriet worked. She was thirty-four, maybe thirty-five, with a heavy chest that stretched the red polo of the shop and hips that filled her black delivery pants. She always smiled like she actually liked her job. She always said his name when she handed over the boxes, even though it was printed on the receipt.

Tonight he had timed it. Shower first. The water ran hot over his shoulders and down his narrow chest. He soaped himself slowly, thinking about the way those girls in the videos stood with their feet close together, how the towel would cling for one second after they let go. He dried off. He did not put on clothes. He found the smallest white towel he owned, the one that barely wrapped once around his middle if he tucked it tight under his arms the way they did. It covered him from armpits to the tops of his thighs and nothing else. His cock was already starting to fill, a thin three-and-a-half inches that stood up against the terry cloth like it was trying to peek.

He ordered. Large pepperoni, extra cheese, the usual. He put his phone on the counter and waited in the little hallway of his apartment, the towel clutched in his fists at first, then adjusted, then clutched again. His heart was a drum. Every time a car passed on the street below he thought it was her. He practiced the lip-bite in the mirror by the door. He looked ridiculous and he knew it. Skinny legs, the faint trail of hair down his stomach, the obvious tent in the front of the towel. He did it anyway.

The knock came at 7:41.

Warrick opened the door.

Harriet stood there with the insulated bag slung over one shoulder, the receipt already in her other hand. Her dark hair was pulled back. The polo was a size too small across the bust, the buttons straining. She started to say his name the way she always did, then stopped. Her eyes went down and came back up. The towel. The bare shoulders. The way he was standing in the threshold with nothing else on.

He bit his lip. He let the towel go.

It hit the floor in a small white heap around his ankles. His body was quivering, a fine shake that started in his thighs and ran up into his belly. His cock stood out from his sparse thatch, thin and stiff and flushed dark at the head, three and a half inches of it pointing toward her like an accusation. Cool air from the hallway touched his ass, the backs of his knees, the tight skin of his balls.

Harriet did not laugh. She did not step back. She looked at him the way a person looks at a thing they have wanted to look at for a long time and never had permission. Her mouth opened a little. The receipt crumpled in her fingers.

“Warrick,” she said, and it was not the customer-service voice.

“I watched the videos,” he said. His voice came out smaller than he meant. “The girls who do this. I wanted to know what it felt like.”

She glanced down the hall both ways. Empty. She stepped forward, over the threshold, and he moved back automatically so she could come in. She shut the door behind her with her heel. The lock clicked. She set the insulated bag on the little table by the door without looking at it.

“You’re shaking,” she said.

“I know.”

She reached out and put two fingers under his chin, tilting his face up because he was that much shorter. Her nails were short, practical. Up close he could smell the pizza shop on her, yeast and motor oil and the faint sweetness of whatever lotion she used. Her breasts were right there, heavy in the polo, the dark shadow of her bra visible through the fabric.

“You planned this,” she said. Not a question.

“Yes.”

“For me.”

He nodded. The quiver in his legs got worse. His cock twitched in the air between them, a little wet at the tip.

Harriet made a sound in her throat, almost a laugh but warmer. She let go of his chin and reached down. Her palm was warm when she wrapped it around him. He was so thin that her fingers closed completely, thumb overlapping, and she gave him one slow stroke from base to head like she was measuring. He made a helpless noise.

“That’s all of it,” she said, not unkindly. “God. Look at you.”

She kept her hand there, not stroking yet, just holding him while she used her other hand to pull her polo out of her pants. She dragged it up and over her head in one motion and dropped it. The bra was black, cheap, overfilled. She reached back and unhooked it and her breasts came free, large and pale with wide brown nipples already tight. They sat heavy on her ribcage, the kind of tits that moved when she breathed. Warrick stared. He had imagined them. The imagining had been smaller.

“You can touch,” she said.

He did. Both hands, because he was shaking too much to be elegant about it. He filled his palms with her, thumbs brushing the nipples, and she made that sound again and pushed her chest forward into him. His cock was trapped against the zipper of her work pants, a damp spot already forming. She took his wrists and moved his hands down to her waist, then lower, guiding him to the button and the zipper.

“Take them off me,” she said.

He fumbled. The pants came down her thick thighs, taking the black panties with them. She kicked the shoes off, stepped out of the rest. She was dense through the hips, a dark patch of hair between her legs already glistening. She was wet. She had gotten wet looking at him in the doorway with his little towel and his little cock.

Harriet backed him toward the couch without being rough about it. When the backs of his knees hit the cushion he sat, and she climbed on, straddling his skinny thighs, her weight making the old springs complain. Her breasts hung in his face. He put his mouth on one nipple because he could not not, and she held the back of his head and let him suck while she reached between them and lined him up.

He was so hard it almost hurt. The head of him nudged her folds, slipped, found the entrance. She sank down.

There was not much length to take. She took all of it in one slow sit, and then she was sitting on his lap with him fully inside her and her ass resting on his thighs. She was hot and tight and wet enough that it made a small sound. She stayed there a second, looking down at him, at the way his whole body was flushed and shaking under her.

“Poor thing,” she said, and rolled her hips.

Warrick’s hands went to her ass because there was nowhere else for them to go. He held on. She fucked him like that, a slow grind that kept him buried, her clit rubbing against his sparse hair, her breasts swaying. She talked while she did it, low and filthy, telling him how small he felt, how she could barely tell he was in there except for the way he kept twitching, how she’d thought about this the last three times she’d brought him a pizza, wondering if the quiet skinny guy ever jerked off thinking about her.

“I did,” he gasped. “I do.”

“I know you do.” She lifted up a little and dropped, and he saw stars. “Look at this cock. It’s trying so hard.”

She reached behind herself and found his balls, rolling them in her fingers while she rode. He was not going to last. He told her so, embarrassed, and she just smiled and sped up, using him, her thighs working, the wet sound of it filling the little living room. When he came it was a helpless, full-body thing, his skinny back arching off the couch, a thin pulse of come that she took without slowing down. She kept grinding through it, chasing her own, and when she came she did it with her mouth open and her nails in his shoulders, a long low moan, her cunt clamping around what little of him there was.

She did not get off him right away. She sat there, breathing, his softening cock still inside her, a slow leak of come already sliding down onto his balls. She kissed his mouth, finally, tasting like mint gum and something warmer.

“You’re going to order again next week,” she said against his lips.

“Yes.”

“Towel or no towel. I don’t care. But I want you naked when you open the door.”

He nodded. He would have agreed to anything.

She got up. He watched her dress, the way her heavy breasts disappeared back into the bra, the polo tugged down, the pants. She looked like a delivery driver again except for the color in her face and the wetness still shining on her inner thighs before the fabric covered it. She put the pizza box on the counter. She had never even opened the bag until now.

At the door she paused, looked him over one more time, still sitting on his own couch with come cooling on his skin and the white towel in a pile by the entrance.

“You’re cuter than the girls in those videos,” Harriet said. “They never shake like you do.”

She left.

Warrick sat there a long time. The apartment smelled like sex and pepperoni. His cock was small and spent against his thigh. He thought about next week, and the week after, and the way she had looked at him in the doorway before he ever dropped anything.

He picked up the towel, then set it back down. He did not put it on.

On the receipt, under the total, she had written her number in ballpoint, and under that a single line: I’ve been waiting for you to do that since you turned twenty-eight.

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