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Cherry Lolipop’s anal journey

Chapter one: the interview

Lexie pulled into the cracked asphalt lot behind the strip mall, the little blue Honda Civic her dad had surprised her with the day after graduation. The engine ticked as it cooled. She sat there for a long moment, hands still on the wheel, staring at the number in the strip department complex. The whole place looked like a highway motel. No sign, no logo.

She'd dressed up a little more than she had for the photos. A mid-thigh-length denim skirt, pale pink button-up blouse tucked in neatly, white canvas sneakers. Underneath, a matching set, simple pink cotton bra and panties with a tiny scalloped edge of lace. She wanted to be seen desirable, she was taking this seriously.

Her stomach rolled. What if this was a mistake? What if her parents somehow found out? She almost turned the key back in the ignition. Then she remembered the $800 minimum. She exhaled, grabbed her little crossbody purse, and got out.

The walk across the lot felt longer than it should have. Flip-flops would have been easier, but she’d wanted to look put-together. Her skirt swished against her thighs with every step. She could feel her own heartbeat in her ears when she reached the door.

She knocked, three times, barely audible.

The door opened almost immediately.

A man in his mid-forties stood there, maybe a little taller than average, wearing a Metallica T-shirt, a little out of shape (still not in fat territory), faded jeans, and scuffed sneakers. Dark hair, a couple days of stubble. Lexie thought he looked like those car salesmen who appears in local TV ads.

“Lexie Miller?” His voice was low, calm, the same one from the phone.

“Yeah. Hi.”

He extended a hand, firm but not crushing. “My name’s Richard Dennis , but nobody calls me that unless they’re serving me papers.” He gave a small, crooked smile. “Call me Rick. Come on in, sweetheart. You’re right on time.”

She stepped inside. The air was cooler, smelling like cigarettes, which she wasn’t a fan of it. Everything looked so “adult” and that made her a little uneasy. The main room was small, it had a little corridor with two adjacent rooms and a small kitchen with a bathroom at the end. The room at the left had a couch, a couple of tripods with cameras already set up but powered off, a low platform with a plain black mattress, a folding table covered in coiled cables and plastic bins. Five men in total, including Rick. All of them looked over when she entered.

Rick gestured casually. “Guys, this is Lexie. Lexie, meet the team. Mike, the cameraman, the one with the beard. Tony, lights and grip. Dave, sound. And Jake, he’s our PA, runs errands, a little of everything. He’s the baby of the group, twenty-four.”

Jake gave a small wave and a grin. Everyone else nodded or lifted a hand. They were all over thirty except him, somewhere in their thirties to early fifties, dressed like guys who’d been doing this a long time: cargo shorts, band T-shirts, practical sneakers. She felt slightly ogled.

Rick led her to a couple of folding chairs near the table. “Have a seat. You want water? Soda? We’ve got warm Coke and colder water, even beer if you want.” Said with a small laugh.

“Water’s fine,” she said, voice smaller than she wanted.

He handed her a bottle, then sat across from her, elbows on his knees, casual but focused. “Okay. Let’s talk before we do anything else. You read the ad, we talked on the phone, you sent pics. You still here, so I’m assuming you’re at least curious. But I want to make sure we’re all on the same page.”

She nodded, twisting the cap off the bottle but not drinking yet.

“We specialize in fetish content,” he continued, matter-of-fact. “Mostly solo, some light girl/girl if we pair you with someone down the line. Heavy emphasis on the backdoor play, plugs, that kind of thing. Everything’s on camera, bright lights, close-ups. You’ll be naked the entire time you’re in the building on shoot days. From the second you walk through that door until we say wrap and hand you your clothes back. No robes, no stepping out to change. It’s how we keep continuity and energy. Standard for this kind of work.”

Lexie felt heat crawl up her neck. She’d known nudity was coming (she had sent the photos, after all) but hearing it laid out so plainly still made her mouth dry. “So… the whole day? Even when we’re not shooting?”

“Yep. Breaks, lunch, waiting for setups. You’re bare. Clothes go in the locker.” He nodded toward a tall metal cabinet with a padlock on the handle. “You get the key when we’re done for the day. No exceptions.”

She swallowed and nodded. “Okay.”

Rick studied her for a second. “You’ve never done anything like this before?”

“No,” she said quickly. “Nothing. Not even… like, webcam stuff or anything.”

The room shifted subtly, nothing dramatic, but she felt it. A couple of the guys exchanged quick glances. Rick’s mouth curved, not quite a smile. “Fresh is gold in this market.”

Tony spoke up for the first time, voice easy. “We’ll go slow today. Just a screen test. See how you take direction, how you look on camera, how you handle basic stuff. Nothing you can’t walk away from.”

Dave nodded. “And if at any point you say stop, we stop. No questions. But we’re hoping you don’t need to.”

Rick pulled a thin stack of papers from a folder on the table. “This is the contract. Three shoots minimum. You can walk after that if you want, no penalty. But if you bail early without a good reason, you repay any advances or per-shoot bonuses you’ve already taken. Standard clause. Pay’s cash, same day, $800 minimum per shoot, but it will vary according to the session, plus more if the scene sells well or we do extras. We handle all distribution; DVDs mostly overseas, some online clips. Your face stays in, but no real names on the packaging. You pick a stage name today if you’re in.”

He slid the contract across the table along with a cheap ballpoint pen. The pages were dense, legal-looking, full of words like “performer,” “nudity,” “anal penetration,” “right to likeness.”

Lexie stared at it. Her pulse was loud in her ears again. Eight hundred dollars a pop. She thought about the classifieds her dad gave to her, the dentist receptionist job paying nine bucks an hour.

She looked up at Rick. He wasn’t pushing, just waiting, patient. “I… I can sign it?”

“You can,” he said. “If you don’t, no hard feelings. Door’s right there.” Said with an empathetic smile

She picked up the pen. Her hand shook just a little. She signed Lexie Miller at the bottom of the last page, then wrote Cherry Lolipop on the stage-name line Rick had pointed out.

Rick took the contract back, glanced at it, nodded once. “Cherry Lolipop. I like it. Cute. Dumb in the right way.”

He stood, offered his hand again. “Welcome aboard, Cherry. Let’s get you comfortable.”

She stood too, legs feeling wobbly. The crew was already moving: Mike checking a camera battery, Tony tilting a light stand, Jake opening the locker.

Rick gave the contract one last glance, then slid it into the folder and set it aside. “Alright, Cherry. Let’s get moving. We’re gonna do a short screen test today: nothing heavy, just enough to see how you look and move under the lights, how you take direction, and how comfortable you are showing skin on camera. Mike’s gonna roll a couple angles, we’ll run some basic poses, maybe a little light play if you’re up for it. Sound good?”

Lexie nodded quickly, even though her stomach felt like it had dropped two floors. “Yeah. Sure. Let’s… let’s just do it.”

Rick looked at Lexie again. “Let’s start simple. Stand right here, center of the frame. Hands at your sides. Big smile for the camera, Cherry. We’re just getting to know you.”

Rick stepped back, giving her space in the center of the light pool. “Okay, Cherry. We’re rolling now. Just be yourself, look at the lens when you talk, answer honest, nice and natural. Mike’s got the main cam. Ready when you are.”

Lexie took a breath, nodded. The red record light blinked on.

Rick stayed off to the side. “Alright, let’s start easy. Can you tell us your name?”

“Cherry Lolipop,” she said, trying to sound bright. It came out with a little bimbo-ish high pitch.

Rick smiled. “Cute. Age?”

“Eighteen.”

“Perfect. In college right now?”

She stuttered. “N-no. I… didn’t go.”

They just smiled and nodded “There are more paths I see. Why are you here today, Cherry?” Rick asked.

She’d rehearsed this in her head on the drive over. “Money” sounded impolite on camera. “Um… to experiment, I guess. Try new things. See what it’s like.”

Rick nodded like that was the most normal answer in the world. “Fresh perspective. Love that. Any background in modeling or adult work? Ever done photoshoots, webcam, anything?”

“No,” she said quickly. “Nothing.”

The guys gave a light, playful round of applause, Tony even clapped twice with exaggerated slowness. “Virgin talent,” Jake said under his breath, grinning.

A few more easy questions followed: favorite color (pink), dream vacation spot (beach somewhere warm), what she does for fun (watch TV, hang out with friends). Safe, fluffy stuff to warm her up. She answered short, smiling when she could, though her fingers kept twisting the hem of her blouse.

Then Tony spoke from behind a light stand, casual. “You know, Cherry, you look really pretty right now. That blouse and skirt combo? Adorable. But…” he paused, grin widening “…I gotta be honest, I think you’d look even better without ’em.”

The other guys laughed softly, approving. Mike gave a low whistle from behind the camera.

Lexie’s face went bright red. She laughed too, trying to roll with it. “Um… thanks?”

Rick added. “Alright, sweetheart. Let’s get to it. Start with the blouse. Nice and slow, whenever you’re ready.”

Her fingers shook a little as she reached for the top button. One by one, she undid them pink cotton parting to reveal the matching bra underneath. The fabric slid off her shoulders, down her arms. She left it in the floor, no one took it.

She stood there in bra and skirt, arms loose at her sides, nipples slightly visible through the thin cups in the bright light.

She kicked off the white canvas sneakers one at a time, bare feet on the cool concrete. Smaller now, somehow more vulnerable.

The skirt came next: she unzipped the side, shimmied the denim down over her hips. It pooled at her ankles again; she stepped out, handed it over. Now just bra and panties: pink cotton with the delicate scalloped lace, hugging her slim hips, the faint outline of her mound visible under the bright lights.

Rick held up a hand. “Hold there. Perfect. Give us a slow 360, baby. Like a little model walk.”

She turned slowly, trying to look sexy, feeling every eye on her. The panties were hug cut, not thong, nothing dramatic, just enough to show the curve of her cheeks. When she faced front again, she smiled, in a “did I look good?” Way.

Rick smiled. “Look at that. Adorable. You know, I still have those photos you emailed, the ones in the pink heart panties. Saved ’em right in the casting folder. Glad we got the upgrade today.”

Lexie let out a small, self-conscious laugh, half giggle, half exhale. “Oh god… yeah. Those were… um. Kinda embarrassing to send.”

“Nothing embarrassing about them,” Rick said smoothly. “They got you here, didn’t they? And they were cute as hell. But these” he nodded at her current set “these are even sweeter.”

She shifted, crossed one ankle behind the other, suddenly hyper-aware of how little fabric was between her and the cameras. The crew was quiet now, just watching, the red light steady.

Rick kept his tone even, almost gentle, like he was guiding her through something routine. “Alright, Cherry. Turn your back to us now. Slow turn.”

Lexie pivoted on her bare feet, facing away from the lights and the cameras. She felt the their eyes tracing her outline.

“Bra first,” Rick said. “Reach back, unclasp it. Take your time.”

Her fingers found the hooks without much fumbling. She popped the clasp, let the straps slide down her arms in a deliberate, unhurried motion. The pink cotton cups fell away from her chest; she drew the bra forward and off completely, holding it out to the side. Then let it fall to the floor

Topless.

A cold flutter dropped through her stomach. Her small breasts were bare to the cool air, nipples tightening instantly, even if the crew couldn’t see them from this angle yet. There was no going back to “mostly dressed girl who could still pretend this was just a weird modeling gig.” She’d crossed into something irreversible the moment the bra hit the floor. She stood very still, breathing shallow, letting the realization settle.

Rick didn’t rush her. “Good. Now the panties, sweetheart. Slide them down nice and slow. Let us watch.”

Lexie hooked her thumbs into the waistband again. She bent slightly at the hips, pushed the cotton over the gentle swell of her ass. The fabric dragged lightly against her skin as it descended past the tops of her thighs, down her legs, pooling at her ankles. Cool air kissed the cleft of her cheeks, then the sensitive skin between her legs. Her ass was completely exposed now, the last barrier gone. She stepped out of the panties one careful foot at a time, leaving the pink cotton in a small crumpled heap on the floor.

A soft chorus of low whistles rose immediately warm, appreciative, not mocking.

“Jesus, look at that cute little perky butt,” Tony said, voice low and genuine.

“Adorable,” Dave added quietly.

“Perfect shape,” Mike murmured from behind the main camera.

Lexie felt the heat rush to her face and neck even though they couldn’t see it. The compliments landed strangely direct and shameless, yet oddly sweet in their straightforward admiration. She stood fully naked, back still turned, arms hanging loose, acutely aware of every inch of skin they were studying.

“Rick ordered her “Now turn around for us. Slow. Face the camera.”

She inhaled then rotated on her heels until she was facing them again.

Completely naked.

The bright lights hit her full-frontal: small breasts with pale pink nipples standing stiff, flat stomach, the soft blonde triangle between her slim thighs, bare feet planted on the cold concrete. No scrap of fabric left anywhere. Her arms remained at her sides. She felt tiny under their collective gaze, every detail of her body laid open for inspection.

The room went quiet for a long second.

“Look at that young body,” Rick said first, voice warm. “Fresh, perfect.”

“Like a little fairy,” Tony added, grinning softly.

“Seriously pretty,” Jake offered

Lexie’s blush deepened, spreading from her cheeks down her chest. Mortified (god, so mortified!) but the words wrapped around her like unexpected warmth. They weren’t crude or leering; they were looking at her like she was something delicate and rare, something they genuinely liked seeing.

She stood there, heart hammering, skin prickling with goosebumps, and thought one clear, steady sentence inside her head: “I can do this.”

Rick finally spoke again, gentle. “You’re doing great, Cherry. Really great. We’re gonna run a few simple poses next and training. Nothing big. You still good?”

She met his eyes, then glanced at the camera and gave a small nod.

“Yeah,” she said, voice quiet but steady. “I’m good.”

Rick kept his voice low and steady, like he was guiding her through something as ordinary as adjusting a pose. “Alright, Cherry. We’re gonna ease into the next part. Nothing crazy, just some light touching to see how your body responds on camera. Real reactions sell, remember?”

Lexie nodded, though her throat felt tight.

“Sit for us,” Rick said, gesturing to the low black couch that had been pushed into frame while she was stripping. It was simple, faux leather, wide enough for three people. “Right in the middle. Relax your legs”

She moved carefully, bare feet silent on the carpet, and lowered herself onto the cushion. The leather was cool against her ass and the backs of her thighs; she flinched just a fraction before settling. Rick sat on her left, close enough that his knee brushed hers. Tony dropped onto her right side. The couch dipped slightly under their weight, pressing her shoulders between them without quite trapping her.

She felt the difference immediately: clothed bodies on either side of her naked one, the faint warmth of their jeans against her bare skin. Her hands rested in her lap, fingers laced together, trying to cover the soft blonde patch between her thighs without looking like she was hiding.

Rick leaned in a little, elbow on the back of the couch, casual. “Let’s talk a minute while Mike gets the close angle. Just keep looking forward, nice and natural.”

Tony reached over and gave her knee a light, friendly pat,nothing lingering, just enough to make her jump slightly. “You’re doing awesome so far, kid.”

Lexie managed a small, shaky smile. “Thanks.”

Rick started easy. “First boyfriend?”

She swallowed. “Yeah. Um… junior year. His name was Tyler.”

“How long?”

“Like… five months? Then he moved away for college.”

Rick nodded. “First time with him?”

Her cheeks heated again, the flush spreading down her neck. “Yeah.”

“Nice. Gentle guy?”

She gave a tiny shrug, eyes on the camera lens instead of their faces. “I guess. It was… okay. Kinda awkward. We didn’t really know what we were doing.”

Tony chuckled softly. “Most first times are. Who else after that?”

Lexie hesitated, then answered quietly. “One more. It was… a guy I met at the mall food court. We dated for like two months.”

Rick’s tone stayed even, curious but not prying. “They touch you a lot? Or was it mostly quick stuff?”

She bit her lower lip for a second. “Tyler, yeah, hands everywhere, I guess. But nothing super… intense.”

“Ever let anyone play with your ass?” Tony asked, voice light, almost conversational.

Lexie’s breath hitched. “Not… really. A couple slaps during… you know. But no fingers or anything.”

Rick hummed thoughtfully. “What about yourself? You touch back there when you’re alone?”

Her face went scarlet. She stared at her own knees. “No, never.”

“Good to know,” Rick said, like he was filing away useful information. He shifted closer, his arm now resting along the back of the couch behind her shoulders. “One more question before we move on. Your nipples… sensitive?”

Lexie blinked, caught off guard. “I… don’t really know? I mean, they get hard when it’s cold, or when I’m… turned on, I guess.”

Tony made a soft, interested sound. “Allow me to find out by myself.”

She nodded jerkily, pulse loud in her ears.

Tony moved first. His right hand settled lightly on her left thigh, palm warm against her skin. He didn’t grab, just rested there, thumb stroking once in a slow arc. Then he began to ease her leg outward, gentle pressure, parting her thighs inch by inch.

At the same time, Rick lifted his left hand and brushed the backs of his knuckles along the underside of her right breast, barely contact, just enough to make her nipple pebble harder. Then he cupped the small mound fully, thumb circling the areola in lazy loops.

Lexie sucked in a sharp breath. Her legs trembled as Tony guided them wider apart, exposing the soft pink folds between them to the bright lights and the waiting camera. She could feel the cool air hit her there, the sudden vulnerability making her clit throb.

“Easy,” Rick murmured, voice close to her ear. His thumb brushed directly over her nipple now, light pinch, then a slow roll. “Look at that. They’re waking up already.”

Tony’s hand slid higher on her inner thigh, stopping just short of her center, fingers tracing the crease where leg met body. “Pretty pussy, Cherry,” he said quietly, almost appreciative. “Getting shiny for us.”

Lexie’s hips twitched involuntarily. She wanted to close her legs, cover herself, disappear, but the weight of their bodies on either side, the steady hands, the way how she was outnumbered and pinned, it was all to strong for her to refuse. Her breathing came shallow and quick, chest rising and falling under Rick’s palm.

“Good girl,” Rick said as encouragement, rewarding her with another slow circle around the stiff peak. “See? You do know.”

Tony’s fingers finally brushed her outer lips; feather-light, no pressure, just enough to part them slightly and let the camera catch the faint glisten. “She’s wet already,” he announced, calm and clinical. “Little clit’s peeking out too.”

Rick’s left hand stayed downward on her stomach for a moment longer; flat palm, warm and steady, before it began a slow, deliberate slide downward. His fingers trailed over the soft skin just below her navel, tracing lazy circles that made her muscles flutter. Lexie tensed instinctively, thighs clenching for a split second as his hand drifted lower, joining Tony’s on her inner leg.

Tony’s fingers were still resting high on her right thigh, thumb stroking the sensitive crease where leg met groin in slow, patient arcs. Now Rick mirrored him on the left: palm settling against the smooth skin, then gliding inward, fingertips brushing the tender flesh inches from her center. Both men kept their touch light soft caressing the pinky lips, but not enough to actually stimulate her properly, just enough to make her react.

Lexie’s breath hitched. Her legs, already parted wide by their earlier guidance, trembled under the dual attention. She felt exposed in a way that went beyond naked. Back in highschool she was the untouchable girl who kept dumping boy and teasing them, now had a two men toying her open sex freely, to their own amusement, and she was letting them, even feeling it. She felt the humiliating wetness that had started to gather and now glistened visibly under the lights.

At first she stayed rigid: shoulders tight, fingers digging into her own palms in her lap, small huffs of air escaping through her nose as she tried to stay still. The shame burned hot in her chest “they’re touching me, actually touching me, and the camera’s getting it all” but the contact itself… wasn’t bad. It was warm. Slow. Almost careful. Their palms were rougher than hers ever were when she touched herself alone, and that difference sent unexpected little shivers through her body.

Rick’s fingertips pushed a little more. The shallow intrusion made Lexie’s breath hitch. Rick’s finger moved with lazy, teasing strokes, sliding in only to the first knuckle, then withdrawing, circling the wet opening in slow, gentle motions. Tony’s fingers stayed on her outer lips, occasionally brushing her swollen clit with light pressure. The dual attention sent small, unwelcome sparks through her brain. Her walls fluttered around the invading finger each time it dipped inside.

For a few long seconds Lexie’s body betrayed her. Her shoulders loosened. Her head tipped back against the couch, eyes fluttering closed as a quiet, surprised sigh slipped from her lips.

“There she goes,” Tony murmured, voice low and approving. His fingers pressed just a fraction firmer, parting her outer lips a little more so the camera could catch the way her clit had swollen, peeking out pink and slick.

Rick let out a soft hum of satisfaction.

The warmth and slow rhythm felt good… too good, even as shame burned hot across her face and chest. She was naked, legs spread wide between two fully dressed men, one man’s finger teasing inside her pussy while the cameras recorded every twitch and flutter. The humiliation made her cheeks flame, yet her hips gave the tiniest, involuntary roll, chasing the gentle stimulation.

Her breathing changed to shallow little pants turning into longer, softer exhales. The tension in her shoulders eased; her thighs, which had been quivering with resistance, slowly fell open another inch on their own. She didn’t moan, nothing dramatic, but a quiet, surprised sound slipped out of her: half-sigh, half-whimper.

It felt… good. Really good. It all blurred into this strange, hazy warmth. For a long moment she let herself sink into it.

Tony chuckled under his breath. “Look at her go. Little Cherry likes being played with.”

Lexie’s eyes fluttered open at the words, a fresh wave of blush hitting her cheeks, but she didn’t pull away. Her body stayed relaxed, thighs soft and open, letting their hands continue their slow, teasing work.

Then, abruptly, both men stopped.

Rick lifted his hand away first, resting it back on her stomach like nothing had happened. Tony followed a second later, giving her inner thigh one last light pat before withdrawing completely.

Lexie blinked, dazed. Her clit throbbed once, hard and unsatisfied, a faint ache settling between her legs. She shifted on the couch, thighs pressing together instinctively now that the stimulation was gone, trying to ease the sudden emptiness.

Rick leaned back, casual as ever, wiping his fingers absently on his jeans. “Introduction’s over, sweetheart. You did great. Real nice responses.”

Tony grinned, stretching his arms along the back of the couch. “Yeah. Wet little pussy, sensitive nips, hips moving on their own. That’s gold.”

Rick stood, wiping his fingers on his jeans. “Alright, Cherry. Let’s move to the bed room for the next part.”

Lexie followed on unsteady bare feet, still completely naked. The crew moved with quiet efficiency behind her: Mike carrying the main tripod, Tony the smaller handheld camera, Jake bringing the lube and gloves. They entered the adjacent room with the low black mattress under bright lights. The air felt cooler on her skin.

“On all fours,” Rick said simply, pointing to the center of the mattress. “Knees wide, ass up high. Face toward the wall.”

She climbed onto the mattress, heart pounding. The black surface was cool and slightly sticky under her palms and knees. She settled into position: hands planted forward, back slightly arched, small round ass pushed up and presented. One tripod camera was positioned directly behind her, lens aimed straight at her tight pink pucker and the soft, glossy lips just below. The second camera was set low in front, capturing her face in tight close-up. Both red record lights blinked on.

Rick snapped on a pair of thin latex gloves. He squeezed a thick glob of cheap, watery lube onto two fingers and smeared it around. The clear gel glistened under the lights. He stepped behind her.

“You’ve never had anything back here?” he asked quietly.

Lexie shook her head, voice small. “No.”

He gave a soft, low chuckle. “I’ll go gentle then.”

The slick tip of his first gloved finger pressed firmly against her virgin pucker. Lexie tensed instantly, her ring clenching tight. He pushed steadily anyway. The finger slid past the tight ring with a slow, burning stretch. A sharp little gasp escaped her as they filled her. It felt a strange, cool, invasive pressure deep inside, with a mild stinging at the entrance that made her toes curl in the air.

A thick glob of excess lube had been pushed around her ring and now dripped slowly downward, a shiny trail sliding over her pussy lips and dangling in a thin string before breaking.

Rick began rocking the finger in and out with steady, unhurried motions, shallow at first, then gradually deeper. Each push made her tight ring stretch and grip around the invading digit. Lexie stared straight ahead into the face camera, mortified. They were recording not just her ass being fingered, but every flicker of discomfort and embarrassment crossing her face. Her cheeks burned hot. Her small breasts hung beneath her, swaying slightly with each rock of his hand. She clenched hard around the finger, trying to push it out, but that only made the stretch feel more intense.

The finger kept moving: twisting slightly, pressing deeper, exploring the tight heat of her ass. The stinging being always present, she just pressed her lips in a small pout trying to ignore it. A soft, involuntary whimper slipped from her lips as he rocked it faster for a moment.

After a minute, Rick eased the single finger almost all the way out, leaving her pucker slightly hollow and glistening. He added more lube, another heavy glob that immediately began dripping down toward her pussy again then pressed two fingertips firmly against her hole.

He pushed both in together.

Lexie jolted lightly, her back arching hard and feet kicking in the air as the wider stretch hit her all at once. “Ah!” A real gasp tore from her throat. The sudden fullness was mildly intense, burning pressure, sharper tingling, her ring forced open around two (very thick) fingers. Her hole clenched violently around them, spasming as it tried to adjust. Panic flashed across her face, eyes widening as she stared into the front camera. The dripping lube made everything slick and messy; more of it was being pushed out with each shallow thrust, running in shiny rivulets down her pussy and dripping onto the black mattress below.

The crew, amused let a quiet, low whistle.

One of them (Tony, she thought) stepped closer and gave her flushed cheek a couple of gentle pats, almost affectionate. “Easy, easy,” he murmured.

Rick continued working the two fingers slowly now, rocking them in and out with deliberate, steady pressure. He twisted them gently, scissoring just enough to open her further. Each motion made her ring stretch and grip, the cheap lube squelching softly with every push. Lexie’s breathing came quicker, short little huffs as she struggled to adjust to the fuller invasion. Her ass cheeks trembled slightly with each rock. The dual cameras caught it all: the close-up of her puffy, stretched ring glistening with lube behind her, and the wide-eyed, mortified expressions on her face in front — the way her lips parted, the flush spreading down her neck, the tiny winces every time he pushed deeper.

He kept the slow, relentless rhythm, ignoring the way her body clenched and fluttered around his fingers. More lube dripped steadily downward, coating her pussy lips and leaving a small wet spot on the mattress. Lexie stayed in position, ass high, letting the fingers work her open while the cameras recorded every second of her first real anal experience.

Finally, after several long minutes, Rick slowly withdrew both fingers with a wet pop. Her asshole stayed slightly gaped for a moment — pink, puffy, and shiny with lube — before slowly contracting back. A thin string of lube still dangled from her ring, stretching downward.

Rick peeled off the gloves and tossed them aside. He reached for the medium silicone plug on the nearby table.

Rick slowly withdrew both fingers with a wet noise. Lexie’s asshole stayed slightly open for a long moment: pink, puffy, and shiny with the cheap lube before it slowly winked shut again. A thin string of the clear gel still dangled from her stretched pussy, until it broke and landed on the black mattress.

“Stay right there,” Rick said calmly. “Don’t move.”

Lexie remained on all fours, ass still high in the air, knees spread wide. Behind her, the guys talked casually among themselves, as if discussing a piece of equipment.

“Nice and tight,” Mike murmured from behind the ass camera, zooming in slowly.

Tony leaned in closer, studying her pucker. “How’d it feel in there, Rick? Warm?”

“Warm and fuckin’ tight,” Rick answered, peeling off the gloves and wiping his hands on a rag. “She was clenching hard the whole time. Good muscle tone though. Should take the plug fine once she stops flinching.”

Lexie heard every word while staring straight into the lens, mortified. They were talking about her asshole like it was just another prop on set. Her ring fluttered involuntarily at the attention.

Rick picked up the next toy from the table; a medium silicone plug, noticeably thicker than his two fingers. The tapered tip was modest, but the widest part near the base flared out significantly, easily the girth of three fingers or more. The neck was short, meaning once the thickest section popped in, it would sit deep and stay there.

“Next step is the plug,” Rick told her simply. “Bigger than the fingers, especially at the base. Just breathe and try to push back against it when it starts going in.”

Lexie’s eyes flicked to the plug in his hand. Her stomach tightened. It looked much bigger in person than she had imagined. “Be gentle…” she whispered, voice small.

Rick stepped behind her again. He squeezed a fresh glob of the thin lube directly onto her pucker and another generous amount over the plug, although he didn’t bothered with smearing it properly. He pressed the tapered tip against her still-slick hole, the excess immediately started dripping down her crack and over her pussy lips in shiny trail and pushed.

The first attempt failed almost instantly. The moment the wider part started stretching her ring, Lexie flinched hard forward on her knees, her whole body jerking away from the pressure. The plug slipped sideways and popped back out, smearing lube messily across her ass cheek and thigh.

“Sorry….” she gasped, face burning with embarrassment. She quickly got back into position, ass up again, breathing fast. “Sorry… I’m ready now. Just…”

She took two deep breaths, trying to steady herself, staring wide-eyed into the face camera the whole time.

Rick didn’t wait long. He pressed the tip back against her pucker and pushed again, firmer this time, steady and unrelenting. The tapered head slipped inside with a sudden pop. Lexie’s eyes widened sharply, a strained whimper escaping her throat as the real stretch began.

It was significantly bigger than the fingers. The burning pressure hit her immediately, a deep, intense stretching sensation as the thickest part of the plug forced her tight ring wider and wider. She clenched hard around it on instinct, which only made the burn sharper. Her toes curled tight in the air, her back arched sharply, and her breathing turned into short, shallow huffs.

“Oh… fuck…” she breathed, voice shaky. The widest part was now halfway through, forcing her asshole open in a way that made her feel full already. The short neck meant there was no relief: once it passed the flare, the plug would lock in deep and heavy.

Once the thick base finally popped past her ring, Lexie let out a sharp gasp, her whole body shuddering. The base sat snug against her cheeks, the heavy toy now buried deep. More of the cheap gel had been forced out during the insertion and now dripped steadily down her pussy and onto the mattress.

She stayed perfectly still on all fours, breathing hard, staring blankly into the face camera with wide, overwhelmed eyes. The plug felt huge — a constant, burning fullness that made her ass feel stretched and claimed in a way she had never imagined. Every tiny shift of her hips made it move inside her, sending waves pressure through her guts.

“Nice pop on that one,” Mike commented from behind the ass cam, zooming in on her stuffed, puffy ring. “Base is sitting pretty.”

Rick gave the base a light tap with two fingers, making the plug shift inside her. Lexie winced visibly, another soft whimper slipping out.

“Looks good,” Rick said casually. “We’ll leave it in for a bit. Let her get used to it while we do some walking shots.”

Lexie remained on all fours, ass high, the thick plug locked deep inside her, lube still slowly dripping from her stretched hole. She kept staring into the lens, face flushed and mortified, already feeling the deep soreness starting to settle in.

Rick gave the base of the plug one more light tap, making it shift heavily inside her. Lexie winced, a small flutter running through her stretched ring.

“Stand up,” Rick said. “Time for some walking shots. Let’s see how you move with it in.”

Lexie carefully pushed herself up from all fours. The moment she straightened, the full weight and thickness of the plug became impossible to ignore. It sat deep and heavy in her ass, the thick base pressing firmly between her cheeks. Every tiny movement made it nudge against her inner walls. She stood on slightly shaky legs, trying to keep her posture normal, but her steps were awkward, a subtle waddle mixed with careful, mincing movements as her ass adjusted to the constant intrusion.

She took a few tentative steps across the room, bare feet silent on the carpet. Her hips swayed a little more than usual, and she couldn’t stop the occasional clench around the plug, which only made the fullness feel more pronounced, still glistening on her inner thighs and dripped slowly from her puffy ring with each step. She tried to act casual, arms hanging loosely at her sides, but it was obvious; her movements were stiff.

“Adorable,” Tony murmured with a soft chuckle, watching her from the side. “She’s trying so hard to walk normal.”

Jake grinned. “Looks like a baby deer learning to stand. All wobbly legs.”

One of the guys (Dave) spoke up casually. “Hey, Cherry. Walk over to the kitchenette and make some coffee for me. Make one for yourself too if you want.”

Lexie nodded quickly, grateful for any task that might distract her from how exposed and ridiculous she felt. She turned and walked toward the small kitchenette at the end of the corridor, the camera trailing right behind her. The plug shifted with every step, pressing deeper when she lifted her leg, nudging sideways when her hips swayed. She clenched instinctively around it, which only heightened the deep, burning stretch. She felt a little of the lube growing down in a shiny line.

She reached the counter, standing on her tiptoes to grab the coffee maker and filters. The motion made the plug push upward sharply inside her, forcing a quiet gasp from her lips. She filled the pot with water, measured the grounds with slightly trembling hands, all while the camera stayed on her, zooming in on her plugged ass as she bent slightly to open the cabinet, then pulling back to catch her full naked body working in the bright lights. Her small breasts pointing, nipples still stiff. Every time she shifted her weight from one foot to the other, the heavy toy reminded her exactly where it was lodged.

When the coffee finished brewing, she poured two mugs, one black for Dave, one with a little of milk, sugar and creamer for herself. She carried them back carefully, walking even more gingerly now, the plug making her steps short and deliberate.

She handed the mug to Dave with both hands. He took it with a nod, blowing on the hot liquid.

They let her stand there for a minute while the camera kept rolling. Rick asked a few wrap-up questions in a calm, matter-of-fact tone.

“How’s it feel having that plug in after the fingers?”

Lexie shifted her weight, the toy moving inside her. “It’s… really full. Heavy. Every time I move it presses deeper. It still stings a little at the entrance.”

“Any different from what you expected?”

She glanced down at her own body, cheeks burning. “Bigger… way bigger than I thought it would be. I didn’t know it would feel this… constant.”

Rick nodded once. “Good. That’s honest. Camera likes real reactions.”

After the short interview, Rick pointed back toward the mattress. “Alright, back on the bed. This time on your back, knees drawn up to your chest. We’re going to remove the plug now.”

Lexie walked back to the mattress, the plug shifting heavily with each step. She lowered herself onto the black surface and rolled onto her back. The position felt even more exposing — she pulled her knees up toward her chest, holding them there with her hands, she felt small. Her ass lifted slightly off the mattress, cheeks spread naturally, the base of the plug clearly visible between them. The front camera angled down to capture her face and upper body, while the rear camera zoomed straight in on her stuffed hole.

Rick stepped between her spread legs. He gripped the base of the plug firmly and began to pull.

The thickest part resisted at first. Lexie’s ring clenched hard around the neck as the wide flare started to stretch her open again on the way out. She gasped sharply, eyes squeezing shut for a second as the burning stretch returned, even more intense now after having it seated so deep for so long. The plug slowly emerged, her pucker stretching wide around the thickest section before it finally popped free with a wet, obscene sound.

A thick glob of lube gushed out behind it, running down over her cheeks this time and pooling on the mattress. Her asshole stayed open for several long seconds (with a little gap, red and puffy from the prolonged stretch) before it began to slowly contract. The empty feeling was strange after the constant fullness, leaving her hole twitching and sensitive.

She lay there on her back, knees still drawn up, breathing hard, staring up at the ceiling while the cameras caught every detail of her freshly-used ass slowly closing.

Lexie stayed on her back for a moment longer, knees still drawn up, breathing slowly as her stretched asshole continued to twitch and slowly close. The empty feeling felt strange after the constant heavy pressure — her ring puffy and sensitive, a thin trail of lube still leaking from her hole and running down between her cheeks onto the black mattress.

Rick gave a small nod. “Alright, that’s a wrap for today.”

Lexie sat up carefully on the edge of the mattress, her legs a little shaky. The movement made her freshly-used hole clench involuntarily, sending a deep, lingering soreness through her ass. She looked toward the cameras, still blinking red.

Rick stepped in front of the main lens. “That’s it for Cherry Lolipop’s first screen test. Thanks for watching. See you in the next one.”

The red lights flicked off.

The crew relaxed slightly. Mike stretched his arms, Tony started coiling a cable. Rick turned to Lexie with a casual smile.

“Congrats, Cherry. You did great for your first time.”

She sat there naked, hands resting on her thighs, still feeling the deep ache and the slick mess between her cheeks. “Did I… do it right?” she asked quietly, voice uncertain.

“Yeah, you were perfect,” Rick said. “Real tight little ass, clenched like crazy around the fingers and that plug. And waddled around with it in. Cute reactions the whole way through.”

Tony nodded. “That hole stayed open after we pulled the plug. A real pretty gape for a beginner.”

Lexie’s face burned hot. The words felt embarrassing (not exactly mean, but blunt and objectifying). She forced a small nod anyway, telling herself it was just how they talked in this industry. “Okay… good.”

Rick clapped once. “We’re glad to have you on the team, Cherry. You’re exactly the fresh face we’ve been looking for.”

He stepped forward and pulled her into a quick hug. His clothed body pressed against her bare skin, the rough fabric of his Metallica T-shirt brushing her small breasts and sensitive nipples, his arm wrapping around her lower back. The hug lingered just a second longer than she expected, his hand resting low on her bare hip, close enough that his fingers grazed the curve of her ass.

One by one the others followed. Tony gave her a friendly squeeze on her cheek. Mike hugged her next, his beard scratching her shoulder as he pulled her close. Jake went last, his hand resting on her waist for a moment.

Lexie stood there letting it happen, acutely aware that the hugs felt less like simple congratulations and more like an excuse to feel her bare skin, the warmth of their clothed bodies against her completely naked one, hands lingering on her hips, ass, lower back, and the tops of her thighs. She didn’t pull away, but the realization was clear now. It was the first time she really felt like the only naked person in the room.

When the last hug ended, Lexie turned toward the main room where her clothes still lay scattered across the concrete floor (the pink button-up blouse crumpled near the folding chairs, the denim skirt pooled where she had stepped out of it, her matching pink bra and panties tossed nearby, white canvas sneakers kicked off in different directions.

She walked over with awkward steps. She bent down to gather everything, feeling the cool air on her still-sensitive hole as she moved. One by one she pulled her clothes back on: first the panties sliding up her legs and settling against her wet asscheeks (the cotton immediately soaking up some of the leftover lube), then the bra, the blouse, and finally the denim skirt. The fabric felt strange against her bare skin after being naked for so long, especially the way the panties pressed the mess between her cheeks.

Fully dressed again, she smoothed her skirt down and stood there, purse in hand.

Rick handed her an envelope with the cash. “Eight hundred, like we promised. See you for the next shoot, we’ll call you with the date.”

Lexie took the envelope, fingers still a little shaky. She nodded, gave a small, awkward smile, and headed for the door.

As she stepped back out into the bright Florida afternoon, the soreness between her cheeks pulsed with every step toward her Civic. She slid into the driver’s seat carefully, wincing as the plug’s memory made sitting feel different already.

She told herself it was just modeling.

But her tight little asshole already knew it was going to be a lot more than that.

EPILOGUE: the aftermath of the first day

Lexie drove home in silence, the Florida afternoon sun beating through the Civic’s windshield. Every shift in the driver’s seat sent a dull, deep soreness pulsing through her asshole; a constant reminder of the thick plug that had stretched her open for nearly an hour. The cheap lube had dried sticky between her cheeks, and she could feel the wet patch in her pink cotton panties pressing uncomfortably against her puffy ring with every bump in the road.

When she finally pulled into the driveway, the house was still empty. She slipped inside quickly, locking the door behind her, and headed straight to her bedroom. The soreness made her walk with a subtle, careful waddle she hoped no one would notice.

In her room she peeled off the denim skirt and blouse, then hooked her thumbs into the waistband of the pink panties. As she slid them down, the fabric clung wetly to her skin. The crotch and the back panel were visibly stained: messy, dark, shiny patches from the excess lube that had leaked out during the session and while she was walking around the studio. A thick smear coated the gusset.

She grimaced, balling the ruined panties and tossing them into the corner of her closet. Standing naked from the waist down, she reached back with a handful of tissues and wiped between her cheeks as best she could. The lube was stubborn, slick and messy leaving her ring tender and slightly swollen. She cleaned what she could, but the deep ache remained, a strange, full feeling that made her clench involuntarily every few seconds.

Her drawer was almost empty. No clean adult pairs left; only the old childish ones she’d had since middle school. She pulled out a pair of pale yellow cotton panties with tiny blue stars scattered across them, the kind with a little bow on the front. They were small and snug, riding high on her hips and cutting slightly into her cheeks. She stepped into them and tugged them up. The soft fabric settled against her freshly-used hole, now feeling “fresher” and “cleaner” without any lube between her cheeks. It felt oddly innocent against the soreness; a childish contrast to what had just been done to her.

Lexie pulled on an oversized faded T-shirt (one she’d stolen from her dad years ago) that hung to mid-thigh, then flopped onto her unmade bed. She grabbed a gossip magazine from her nightstand and tried to lose herself in the pages: celebrity breakups, fashion tips, mindless fluff. But her mind kept drifting back to the studio: the lights, the two cameras capturing her face while Rick’s fingers worked inside her, the heavy plug stretching her wider than she thought possible, the awkward waddle to the kitchenette while they filmed her ass, the way the men had hugged her naked body like they were testing how she felt.

She shifted on the bed, wincing as the soreness flared again. It’s just modeling, she told herself. Just my butt. Not even real sex. The money’s good. I can handle it.

The front door opened around 6:30 p.m.

“Lexie? We’re home,” her mom called softly.

Lexie’s stomach tightened. She expected the usual gentle scolding: the “you need to do better” talk. She stood up quickly, smoothing the oversized T-shirt down over her hips, but it barely covered the yellow star-patterned panties. The childish underwear rode up slightly on one side, giving her a subtle wedgie again.

She padded out to the living room, bare legs and all. “Hi… I was just about to change and clean up…”

Her parents looked at her: the messy hair, the oversized T-shirt, the small yellow panties peeking out underneath but their expressions stayed soft, no lecture coming.

“How did the modeling job go today, sweetheart?” her mom asked, setting her purse down.

Her dad smiled tiredly but genuinely. “Yeah, tell us. Did it go well?”

Lexie blinked, surprised. No scolding. Just genuine pride.

“It… went okay,” she mumbled, forcing a small smile. “I think I did fine.”

Her dad opened his arms. “We’re proud of you for getting out there and working hard. First real job and everything.”

Lexie stepped forward and hugged him from the side, the way she always did; her head resting against his chest, one arm around his waist. His hand settled naturally on her lower back, warm through the thin T-shirt. The hug felt safe and familiar, his palm broad and steady, not wandering. She could feel the difference immediately: this was nothing like the studio hugs. Those had been heavier, longer, hands sliding over bare skin with clear intent to feel her body. Here, her dad’s touch was innocent, protective: just a father hugging his daughter.

Still, she felt a wave of self-consciousness wash over her. She was eighteen now, technically an adult, yet here she was in tiny childish star panties, the hem of the T-shirt barely covering her ass, hugging her dad while her asshole still throbbed from being stretched and plugged on camera for money. The contrast made her cheeks heat up. A quiet inner shame twisted in her stomach “this isn’t really my job… not the way they think “ but she pushed it down.

She nodded against his chest. “Thanks, Dad.”

Her mom smiled warmly. “We knew you could do it if you tried. Dinner in a bit?”

Lexie pulled back, tugging the T-shirt down a little lower, suddenly hyper-aware of how the yellow panties clung to her still-sensitive cheeks and the faint damp spot forming again from the leftover lube. “Yeah… I’ll be back real quick.”

She padded back to her room, the soreness pulsing with each step, the childish fabric of the star panties grinder against her cheeks from the motion. She closed the door behind her and let out a long breath.

On her desk, the computer screen glowed faintly. She sat down and opened her email. A new message from Rick was already waiting.

Good first day, Cherry. Next shoot scheduled for Thursday. Bring the same energy. We’ll start with something a little bigger this time.

Lexie stared at the screen for a long moment, thumb hovering over the reply button. The deep ache between her cheeks reminded her exactly what “a little bigger” probably meant.

She typed a short reply anyway.

Okay. See you Thursday.

She hit send, then flopped back onto her bed, magazine forgotten beside her. The yellow star panties still wedging her.

It’s just modeling, she told herself again, closing her eyes. Just my butt.

But the soreness, the leftover stickiness, and the memory of five dressed men casually working her open told a different story.