Shoplifting Roleplay

The walls were lined with shelves, boxes labeled lost and found, and a wall of monitors with security camera feeds. “Take a seat,” the guard pointed at a chair, and I followed his directions. He sat in a comfier looking computer chair across the desk. “We’ve had reports of you shoplifting.”

My heart skipped a beat, living the nightmares I had after my first and only time shoplifting back in the 6th grade. I couldn’t sleep for days until Delja finally confronted me and helped me return the item in question.

He coughed and did a little motion with his hands, urging me to play along. It wasn’t my nightmares come true, it was the guard’s attempt at roleplay. I wonder how many times he’s fantasized about strip searching a cute young shoplifter. With my nerves recollected I delivered my line, “I don’t know what you’re talking about.” I crossed my arms, puffed out my chest, and leaned back, doing my best to act unbothered.

“Well, look miss,” he paused, waiting for me to fill in the blank.

“Martin.”

“Well, miss Martin, to be sure, I’ll have to conduct a strip search. Unless you’d rather have the police involved.”

“Please, not the police,” I played along.

He licked his lips, “That’s what I thought. Stand up, and start with the shirt.” I stood, trying my best to look shy and nervous. “Well, you obviously didn’t steal a bra,” he laughed as I let my shirt fall away. I halfheartedly tried shielding my chest, playing my part in the scene.

The chair squeaked under his weight as he leaned forward, scooting closer. He reached out, pulling away my arms, “Gotta check that you ain’t got anything stored up under.” As if my boobs were big enough to hide anything of the sort. But I didn’t move as he fondled them, lifting and letting them fall back into their perky homes.

He leaned back, “Hmm, shorts next.” I popped the button, slowly unzipping to reveal my canary yellow panties. His breathing was strained as he adjusted his crotch. My tiny denim shorts hit the floor. “I knew it. Stolen panties, I’m going to need to confiscate those.”

“Please, sir, I’m so sorry, I didn’t mean to,” I pouted, using my hands to cover the front of my ‘stolen’ panties.

He laughed, “You didn’t mean to steal panties?” He held out his hand, and I slowly worked them down my thighs until they joined my shorts on the floor. I turned to bend over, giving the guard a nice view of my teen pussy. I could hear the hitch in his breath, and his face was red when I stood up handing over the yellow garment.

“And they’re ruined, I was hoping to help a young thing like you out. But you can’t even return these to the store, they’re soaked through. See?” he held my underwear up to my face, and indeed I could see the wet spot left by my arousal. “I guess now I have **** but to call the cops.”

“Please don’t,” I begged, dropping to my knees with my hands clasped in his lap. “My mom would kill me.”

“Well, I could maybe look the other way, if you made it worth my while,” he licked his lips again. He started tugging at his belt, with that out of the way I quickly took over unfastening the button and tugging at the zipper. His boxers were tented by his erection, I fished it out revealing his rod. My fingers delicately wrapped around it, gray pubes sticking from the opening at the base.

“And you won’t call the cops?” I asked, leaning in close so he could feel the heat of my words against his cock.

He groaned, his cock twitching in my grasp, “I think that could be arranged.”

And with that I placed my lips to the underside of his cockhead. The older man moaned, his hand rested against the back of my head. His grasp led me to taking him into my mouth, my tongue flicked under his shaft as I dove deeper along his shaft. My mouth filled with his dick, looking up I could see him smelling the crotch of my panties.

I touched myself as I bobbed along the guard’s erection. My core ignited in pleasure at the long awaited touch. My arousal having been building since hearing Mom yelling at Carl earlier.

The guard groaned pushing down on the back of my head, his cock filling my throat. “Fuckin’ hell. That’s good.” I tasted precum as his thickness retreated against my tongue. “Get on the desk,” he panted. My young body was able to quickly rise from the floor, while he struggled to rise from his seat.

“Like this?” I asked leaning over the edge of the desk. My ass hanging off the end.

He caressed my supple bottom, his digits digging into my curves. His spit soaked cock, pressed against the back of my thigh. “No, on your back.” I flipped over, lying with my feet in the air. He was unbuttoning his shirt, revealing his gut and gray haired chest. His cock slid over my mound, my legs coming to rest against his torso.

“God, you’re stunning,” he huffed, his cock sliding back over my mound as he lined himself up. His cock pierced my core, sending a wave of pleasure through my needy body. I pushed off the table, eager for more. His fingers tweaked my nipples, and I moaned in ecstasy. Each thrust of his hips pushing his weight against my legs, and pleasure through my filled hole.

He huffed and huffed as he exerted himself, thrusting into my teen pussy. His face was turning a bright shade of red as sweat beaded against his temples. I snaked a hand between us, his gut pushing down against my wrist as he leaned forward sandwiching it between us. I teased my clit, my orgasmic release so close.

My knees pressed to my shoulders bent in half as he leaned more and more over the desk. He used one hand to pull my head closer, I fought the weight of him over me to close the gap. His slimy tongue invaded my mouth, just as my fingers brought forth my orgasm. I fell back onto the desk, my legs shaking against his torso.

And the squeezing of my vaginal walls was obviously enough to milk the older gentleman’s orgasm as well. For a moment, I feared he would collapse atop me, snapping me in half. Luckily he held himself up with one hand on the desk, his warmth filling my depths. Spit dribbled from his lips as he grunted as gave his final thrusts.

And when he finally pushed back, freeing me from the pressure of him atop me, my legs fell limp off the edge of the desk. The guard just stared at my slackened body, probably waiting to wake from his dream. “You want to clean me up?” he asked gesturing to his cock, glistening with our combined sexual fluids.

I slid off the edge of the desk, lowering myself to the ground. I wrapped my fingers around the base of his cock, steadying it as I ran my tongue along the shaft. Each lick filled my mouth with our taste, until he was nearly clean. I took his cockhead between my lips and with one deep plunge swallowed his shaft. Finishing the clean as my lips squeegeed his dick clean.

I gave him one final kiss on his slowly deflating member before helping secure it within the confines of his boxers once again. He collapsed back into his chair, completely exhausted. “If you ever get caught shoplifting at this mall make sure to ask for Victor,” he laughed.

“If my mom ever gives you trouble make sure to ask for Clair,” I said with a wink.

"I have a feeling she'll be randomly searched more often," he chuckled, working on the buttons of his shirt.

I stood up locating my clothes, “Have you seen my panties?”

“Now, I can’t go returning stolen items. It’d be unethical,” he laughed showing me my panties balled up in his fist.