The Shoplifter 5

Never in his 30 years had Tim done anything wrong. He paid his taxes, he followed the speed limit, he even volunteered at the local soup kitchen twice a week. So why, oh why, did he take the cologne? It was the principle of it really. I mean, $200 for a bottle of fragrance? The department store was the crook, not him.

He had almost gotten away with it too. He was two steps out the door when he heard a high-pitched voice say, "Sir?", causing him to turn around. He was greeted by a 5'1" skinny little blondie in a security uniform. "I'm going to have to ask you to come with me," she said. And that's how he wound up back here.

He was sitting nervously alone at a table, an empty chair across from him in the security office. Then, the door opened and the blonde woman entered. She was quite short, even compared to Tim, who was only 5'7" himself. She was thin too, probably barely weighed over 100 pounds. She was practically swimming in her security uniform. She was college-aged, probably a part-time gig she had while she attended school. She stepped over to the empty chair and sat down across from Tim.

"Any idea why we brought you back here?"

"I'm the one-millionth customer?" Tim said.

"Very funny. It's about what's in your pants."

"In my pants?"

"Don't play dumb. The bottle. What's your name?"

"T-Tim"

"Well Timmy, I'm Hannah, and it's my job to protect the store's assets."

Tim shifted in his seat uncomfortably. He still had the cologne in his pants, and she knew it.

"Now, I know you've got a bottle of cologne," she continued, "but what I don't know is what else you've got."

"It's just the cologne, I swear."

"So you admit you took it?"

Tim buried his face in his hands. Idiot. He'd fallen right into her trap.

"I'd hate to have to call the police," Hannah said, "But without knowing what you all took, I'll have to call an officer down to sort it out."

"No, please, I'll do anything," Tim said.

Hannah looked up for a moment, thinking. "Well," she said, "I suppose there's one way I could know you didn't have anything on you. Stand up."

Tim did as he told, stretching his short, thin frame up out of his seat. He was wearing a T-shirt and jeans, not the type of clothing they even sell at these stores.

"Take your clothes off," Hannah commanded.

"My-my clothes?" Tim said.

"Yes, I need to strip search you, make sure you haven't taken anything else."

For most men, they may just bite the bullet and accept their fate. But for Tim, getting naked was a bigger ordeal, especially in front of a lady. See, Tim has an unfortunate problem in his pants. The size of his member was embarrassingly small. Maybe three inches erect. Maybe. Flaccid, it was like a little button with the head poking out, no visible shaft at all. Tim had spent his life staying out of locker rooms and doctor's offices just to avoid the shame, but there was nowhere to turn now.

"Umm, what if I just empty my pockets? See, like this," Tim said and he reached into his pants and retrieved the cologne. He put it down on the table. "That's all I have, I swear."

"Can't trust a thief," Hannah said. "Now off with your clothes, or I call the cops."

Resigned, Tim raised his shirt above his head, revealing a thin but doughy abdomen. Tim was only 150 pounds, but he spent more time gaming rather than working out, and his thin soft body showed it. He unbuckled his pants, slowly lowering his jeans to the ground. He took them off completely, leaving him standing in just a pair of white briefs.

"Ha, nice tighty whities, dork," Hannah said. She walked up to him and got right across from him, really close. She looked up at his face and then down at his crotch. "Well, I can see you aren't smuggling anything in these," she said. It was true, his bulge was practically non-existent in his briefs. There was a lot of empty space where a man's cock should be, and he almost looked like a woman in his underwear.

"No, I don't think there's anything there at all," Hannah said and she grabbed his crotch, shocking Tim. "Oh wow, there is a little penis in there," she said. She felt him up, caressing his little balls and cock in her hand, "Your balls are so tiny, they're like raisins."

Tim blushed at this comment. It had been a long time since he'd felt a woman's hand near his crotch. He'd dated in the past, but most of his girlfriends wanted little to do with him in the bedroom, and Tim often found himself cheated on in his relationships.

His small cock started to stiffen in his underwear, and he was hoping that Hannah couldn't tell. Evidently, she could not as she moved her hand without a comment.

"Now, as silly as you look in those," Hannah said while pointing at his briefs, "I'm gonna need you to take them off."

Tim looked down at his skinny body covered by the thin white cotton. He did look rather silly, standing there in his underwear in front of this beautiful college-aged woman, reduced to nothing over a bottle of cologne. He sighed and hooked his thumbs into the waistband of his underpants and lowered them, revealing his tiny hard cock.

Hannah started laughing, "Oh my God, you have no dick!"

Tim covered up his privates with his hands in shame. "Hands at your sides," Hannah demanded, and Tim obliged. "I just can't believe how small it is," Hannah said. "My boyfriend is more than twice as big."

"Well, you can see that I don't have anything else," Tim said. "Can I get dressed now?"

"Not so fast. Spin around for me," Hannah said.

Tim did as he was told and turned around, showing his cute little butt to Hannah. His behind was round and small and firm. She patted him on the butt and said, "Okay, turn back around."

He spun around again and was facing her, his little cock throbbing.

"Are you hard?" Hannah asked.

"No," Tim lied.

"Yes you are! Oh my God it's so small. Smallest I've ever seen." She took a step closer to him. "I thought my ex from high school was small, but you've got a thimble."

"You've made your point," Tim said. "And you can see I haven't taken anything else. Can I go now?"

Hannah looked up again, thinking, "Curious," she said.

"About what?" Tim said.

"If I could even feel your dick. I mean, it's so small, I bet you would just fruitlessly hump me while I lie there." Tim said nothing, looking at the ground, away from his little dick. "Tell me something Timmy. Do you want to fuck me?" Tim demurred, saying nothing. "Well?" She asked.

"Y-yes," he stuttered.

"What?"

"Yes. Yes I want to fuck you," Tim said.

"Well Timmy, today is your lucky day. I want to know if I can feel your cock, I want to see your little man in action."

She started to unbutton her security uniform shirt. Tim could see glimpses of her flat tummy and white bra come into view. She unbutton her shirt and threw it aside, standing there in her plain white bra. Hannah was slim, and as a result did not have large breasts. Her bra size was only 30a, and she often didn't wear bras, though she always did at work.

She unbuttoned her pants and lowered them too, revealing a pair of plain white cotton briefs. "You aren't the only one who wears tighty whities, Timmy," Hannah said. Then she climbed on the table, lying on her back. She raised her hips and slid her panties down her ankles, leaving her bottomless. Tim stared at her beautiful trimmed pussy with light blonde pubic hair. She had small pussy lips and a gorgeous slit. Tim's cock was aching as he stared at her.

"Well?" Hannah said.

Without a word Tim climbed on top of the table and was over Hannah. He tried to enter her dripping pussy, but his cock kept slipping out. He slipped out three or four times before Hannah said, "Ugh, just let me," and she grabbed his little cock and put it inside her.

Tim started pumping slowly inside her, thrusting his three-inch meat in and out. "You feel amazing," Tim said.

"You don't," Hannah said. "I can barely feel your little dick. It's like, poke poke poke."

"Uh, sorry," Tim said and he started thrusting faster, changing his angle. He fucked her hard and long, but not deep. He was grunting and moaning as he pounded her pussy.

"This is sad," Hannah said. "My boyfriend would have me squirting by now. You aren't a man, Timmy."

With that, Tim's little cock swelled and burst into Hannah's dripping pussy. "Ugh, you're lucky I'm on birth control." Hannah said. Tim was breathing heavily and exited her, falling over onto the floor. Hannah stood up and threw Tim's tighty whities on his head and left him lying on the floor.