Sher, not Sherrie – Exhibitionist & Voyeur – Free Sex Story

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Sherrie could admit that shouldn’t have been speeding. It was dangerous and she knew better than to not follow the rules, rules were usually something she was a stickler for. But after the day she was having, she needed some sympathy.

Sherrie had a whole night planned out for her and her boyfriend. It had been months since they had Sex that could pass for any sort of fulfilling, so she decided to do something different. But of course, he had canceled on her. Again. So now she had to drive back to her apartment at 10 PM, Horny as all get out, and lonelier than ever. Which wasn’t so bad until you considered what she was wearing.

To “Spice Things Up”, she had made a trip to the local Sex store and was dressed in her new purchase. A lacy pushup bra was the only thing between her C-cup breasts and the chilly Autumn air. A garter belt was strapped around her waist, holding up a sexy set of black tights.

But she wasn’t clad only in underwear, she was wearing a short black skirt if you could even call it that. The strip of fabric was closer to a headband than an actual outfit. Underneath was a skimpy black thong but that wasn’t the most scandalous addition to her outfit.

Her plan for the night was to show up outside his house dressed in just her lingerie, and when he pulled down her underwear there it would be. An adorable butt plug between Sherrie’s Ass cheeks.

The thing about Sherrie is that even without the slutty getup, she was already pretty Hot. Curly black hair fell around her face perfectly framing the spray of black freckles on her brown skin.

She was 23, so her boobs weren’t sagging and they were accented by sizable brown nipples. Sherrie used to hate that about herself, she could never go braless in light-colored shirts, or else she’d get disgusted stares from women and leers from creepy old men. Her tummy was fairly flat, although not quite muscular. Sherrie had pretty long legs too, but the thing at the top of them was what made her so popular throughout college.

Her Ass was round and sweet like an apple, the kind of butt you were just dying to sink your teeth in. It was known to sway effortlessly no matter how she walked. And playing volleyball was a hassle for her, as her Ass always ate the shorts right up, leaving a sweep of cheeks to be seen by anyone who looked her way.

And many were trying to look her way right now, in her planning for a perfect date she had forgotten any other clothes than the underthings she had on. Meaning at every red light she just had to cross her fingers that no one would look inside her car.

“Why didn’t I get tinted windows?” She chided herself and chewed on a nail. Sherrie reasoned that no children would see her since it was so late. But that wasn’t enough to calm her nerves, she pulled up to the next light and suddenly heard yelling. There was no mistaking, someone must’ve looked over.

Painstakingly she turned to face the sound and saw a truck full of men, probably in their mid twenties, older and younger than her. She felt herself turn red, it was dark outside but there were still so many lights around she felt as though she was on display.

The men in the truck were hollering and smiling like they were at a concert. Their eyes practically glazed over as they took in all they could see of Sherrie’s body. Not much, but even the tops of her breasts were enough to rear them up.

One of them motioned for her to roll down the window and surprisingly, she did. It’s not like they could say anything that would hurt worse than her boyfriend’s actions.

“H-hi.” She said, smiling meekly.

“Hey baby girl, can I call you that?” The man in the passenger seat had rolled down his window and was smiling at her brazenly.

Sherrie pouted slightly, something her lips were perfect for, a dark pink shade like the inside of a rose, so very soft and supple. “Well my name is She-,” She cut herself. Even at 23 stranger danger lessons from childhood still rang in her ears. “I’m Sher,” She said.

“Well Sher, I’m Maverick,” He said, dipping his trucker’s hat at her. “If you don’t mind me asking… where are your clothes?”. His friends howled with laughter in the backseats.

Sherrie furrowed her brows, she had just about had it with men today. “Well I tried to surprise my boyfriend with something sexy, but he said he didn’t want me. So now I’m driving myself home, but of course, I get stopped and teased by you assholes!” She shouted, silencing the men inside the vehicle, the angelic curls around her face shaking with her intensity.

“Woah, naked chick’s kinda angry…” One of the men, Ezra, in the back said, eyes wide.

“It’s a little Hot.” One of his friends, Drew, commented. Sherrie dipped her head under shame’s weight.

Maverick tilted his hat up, “Your boyfriend must be an absolute idiot, because if I had a girl like you, I don’t think I could say no if I tried.”.

He looked her over and Sherrie understood why Hot people were called “cool drinks of water” because Mav looked at her like she was the only thing that could quench him.

“You really think so?” She asked, despite herself. Why did the opinion of an absolute stranger even matter to her? Even if he was a very handsome stranger, even from feet away she could see he had long lashes, full lips, and a sexy five o’clock shadow.

Sherrie was a sucker for facial hair, her boyfriend thought it looked too messy. “Trashy” He called it. But tonight trashy looked really fucking good.

“I mean,” Maverick smiled a bit. “I can’t see all of you, maybe if I got a better look at the rest of you I’d know.”

Sherrie gasped and covered herself up before giggling a bit. Maverick and the men laughed as well. “But we’re in public.” She reasoned although she could feel herself getting drunk off of the positive attention. Different from the cold treatment she’d received the past few months.

“Who’s gonna see you, Sher?” He asked, which was fair. The streets were practically empty and with all their talking they had missed the last green light. There were a few passing cars though, none of them slow enough to catch a glimpse of her.

“I don’t know,” She said, still needing to come across as coy. In reality, a part of Sherrie wanted to show off to these guys. She knew she was gorgeous, but it had been forever since her boyfriend had said anything nice about her.

Despite her better judgment, she had a familiar feeling growing in her stomach. No. She wasn’t… turned on by the attention was she?

“Oh please Sherrie, I just know I’d like what I’d see,” Maverick said, the begging should’ve been a turn-off, but that smile of his made it charming.

“O-okay,” She called out, putting her car in the parking and undoing her seatbelt. Her hands shakily opened up the car door. She stuck out a single long leg and the men seemed hypnotized to see the rest of it. So she complied, she stood outside of her car completely and smiled bashfully.

“What do you think?” She asked, her hands nervously flitting up and down her smooth skin, not quite sure where to rest. The response was a chorus of praises.

“I have GOT to get my hands on those titties.”

“Fuck that skirt is so damn tight,” Ezra whispered

“Turn around for us baby I’m begging.” Drew crowed.

Sherrie smiled, eye wide. “You- you wanna see my Ass?”

Maverick smirked, “Well from the way you’ve been rubbing those thighs together I have a feeling you want us to see it too.”

Sherrie would’ve been pissed, but what could she say? She could feel a familiar tingle growing, her underwear was growing even tighter and her nipples were beginning to harden as well. It was a fact, she was getting turned on.

She turned slowly and faced her car, playing it up a little bit, she shook her Ass cheeks until they made the skirt rise til it was bunched at her waist.

Sherrie smiled at the resulting cheers, her heart humming birding in her chest. The cool air made goosebumps dance on the supple skin of her butt.

“Like what you see?” She asked a level of confidence she hadn’t felt in some time washing over her.

“Make that thing move baby!” Someone shouted and Sherrie obeyed. She bent her knees and started twerking, something she hadn’t done since college, much less on the side of the road for a bunch of strangers in her underwear.

This was no longer only for the viewer’s pleasure. As her full cheeks bounced she felt the motion go towards her pleasure center. Her labias were rubbing against each other, gradually watering with arousal. Sherrie felt moisture collecting in her panties, the thought of being seen with so little clothes on was making her wet.

They whooped even louder and she licked her lips while smiling. “Yeah, you like that baby?” She asked, reaching back to smack her Ass cheek with her hand and watching triumphantly as it wobbled. She felt her clitoris throb.

A honk from behind the two cars sounded, Sherrie jumped then turned in horror to see headlights looking back at her. All of her confidence disappeared and she squealed in fright, fumbling with her car door handle.

“Follow us!” Maverick shouted, and their truck made a turn down the road and into a little parking lot. Sherrie put her car in drive and followed suit.

“What am I doing?” She thought. “I have a life, a job, I can’t get caught.” She rested her head against the steering wheel once she had parked. Her heart was racing so loud she was sure it would give her away.

A knocking on her window brought her back, it was Mav by the passenger window, looking down at her with a familiar gaze. Something reminiscent of the quarterback from your high school, there was a certain nostalgia in his smile. She rolled down her window. “Hey Sher, I don’t mean to be crass but I’d Love to see you finish that show of yours.”

Sherrie shook her head and tried to laugh off her fears. “Oh no, no more Free shows.” She shuddered thinking of the consequences, the dose of reality sobered up her fantasies.

“Well, what if we paid you back? Give you a night better than what your boyfriend could have done. And maybe we can use some of those toys you bought for it.” He nodded towards the bag of Sex toys in her passenger seat.

“Oh…what the hell.” She laughed. Maverick smiled and grabbed the bag before hopping back in his truck. Sherrie got back out and looked around the parking lot. The store was abandoned so there wasn’t much risk of being caught. She stepped out, partially lit up by a street light. The men looked at her with smiles and she felt like they were at a drive-in movie where she was the show.

Her stiletto heels clicked against the pavement as she sauntered up in front of their vehicle. Her hands drifted up to her bra and started pressing on her tits. She squeezed them tightly, much harder than her boyfriend.

Moving in slow, sure circles. She gave the men a seductive wink as her arms slowly made their way behind her back, unhooked the clasp, and let the bra fall completely.

They clapped and smiled, she felt her nipples tighten in the cold night. The cool air kissed the peaks of her breasts as they hardened.

“Get in here girl!” one of them exclaimed. Strangely enough, she trusted them and stepped into the car. A new part of her life.

The truck was a standard five-seater, there was one man, who had been silent, Alex, as well as Maverick in the front seats and two in the back, Drew and Ezra. They sat on either side of her and she was in the middle.

Alex was fiddling with a camera in the front seats, she started to protest before they reassured her that no one would see the footage.

Sherrie breathed for a minute in the silence before asking. “So what now?”

The man on her right, Ezra laughed and said, “Now we repay you, baby.” He motioned to the bag of Sex toys.

Sherrie’s eyes widened, “Oh really you don’t have to, I haven’t even used half of those before-“

She was cut off by Alex, the formerly quiet one interjecting, “Then why do they smell so sweet?” He grabbed a blue vibrator and inhaled deeply, Sherrie held her breath. She was lying to them. Most of them were toys she was too embarrassed to suggest using with another person.

“Dirty girl,” said Alex, smiling darkly. There was something about him, some level of self-assuredness behind his dark brown eyes, not quite cocky, but the look of a man who was a force to be reckoned with. The smoky blackness of his hair tumbled down to his chiseled jawline that pulsed when he looked her over. “When was the last time a man gave you an Orgasm?”

Sherrie ducked her head in shame. “Months,” She mumbled.

He nodded gravely, “I see, well since you lied to us Sherrie you will have to be punished.”

Maverick reached from the driver’s seat, placed his hand on her inner thigh, and rubbed, sending electricity up her leg and to her middle. “Sher, do you think you should be?” He asked, almost teasing her with the idea of it.

Mav had dark hair like Alex, but his locks weren’t styled in any particular way, more like a general sprouting of curly brown hair going every which way. While Alex had an older, reserved look, Mav had a certain sparkle in his eyes that made him seem younger, less experienced but still somewhat confident.

“Sher, do you think you should be punished?” He asked, almost teasing her with the idea of it.

Hypnotized, she nodded, Sherrie was a little nervous, but she wasn’t scared or intimidated. Or at least, not in a way that didn’t also turn her on.

“If you want us to stop, you can just say purple, okay?”

“Okay,” She nodded, glad some safety measures were being taken.

And with that Ezra grabbed her hands and cuffed them, winking at her playfully as he tossed the key to Alex, who stared her down, his silence only causing the ache in her belly to grow.

Drew easily picked her up and turned her around so her face was towards the bed of the truck and her Ass was facing the front seats. He began to pull the skirt down her thighs before someone tsked, probably Alex.

Suddenly Sherrie heard a ripping noise and squealed as she realized her skirt was torn clean in half! That was the only shred of real clothes she had left. Now all she had on was a thong, tights, and stilettos.

“Now Sher,” Maverick began, lazily moving her hand across her Ass, “Why are you being punished?” Everywhere his hand went was tingling.

“Because I’ve been bad,” She smiled at no one, looking out of the truck’s window.

Thwack!

Alex had slapped her Ass, clearly not satisfied with her answer.

“Be specific, Sher,”

“Ummm,” Sherrie panicked. What had she done? “Uhh, I took my clothes off?” She answered.

Thwack! Thwack! Thwack! These weren’t the halfhearted smacks she received in bed before. These stung.

She felt her Ass cheeks jump at the impact.

“Mmmhmmm,” Alex’s rough hands grazed over her soft skin. “But don’t you have a boyfriend?”

Her face heated, fuck, she hadn’t thought about him in a while/

“Yeah,” she answered, ashamed.

“So why would you take off your clothes for a bunch of strangers?”

“Because I wanted to.” She answered.

“Why?”

Sherrie stuttered “Well, I don’t know why.”

Maverick sighed and she could practically see the disappointed facial expression.

“Go for it boys,” He granted permission and in a flash Drew and Ezra were pinching her nipples. They were already sensitive but this was so much unpredicted stimulation. Sherrie squealed like a pig as they twisted back and forth between their index and thumb, then simply rolled it between their fingers.

She shook, which only made the sensation greater.

Over the sounds of her yelps, Alex asked again.

“Why Sher?”

She hesitated before answering, she knew the answer and the pain in her nipples coaxed out the truth.

“I wanted you to see me! I wanted someone to want to see my body, I like being exposed!” She shouted out to the truck, it was true.

That’s why she drove to her boyfriend’s house practically naked, didn’t bring any extra clothes, and had spanked herself in front of strangers. That’s why she said okay to this being recorded. She loved the rush, that’s why she was leaking down her thighs right now.

“Thank you, but because you lied you’ll have to be spanked 25 times.”

Ezra and Drew laughed at her moans.

Sherrie wasn’t sure if she was dreading or looking forward to being spanked. She felt a pair of hands pull down her underwear.

“Uh oh Sher,” Mav teased lightheartedly as he reached between her thighs and ran his fingers along the slickness of her folds. “Do you… like getting spanked?”

The men laughed at the trails of wetness going down her thighs. Her panties were heavy as they slid down past her knees.

Then the spanking began.

“Count and beg for another,” Alex shouted.

They went to town on her Ass, “One, another!” Sherrie shouted out, much to the enjoyment of her small audience. They smacked her again. “Two, another!”

Each slap made her Ass cheeks jump, thus sending vibrations down to her very sensitive Pussy lips. She bit her lip, trying to savor the feeling of pain nuzzled up so closely to her pleasure.

“Seven, another!”

The cycle continued and the men in the back wanted in so they began groping her breasts again. Sherrie moaned obscenely in reaction. She was so taken aback by the sound that came out of her she completely forgot to count.

Alex raised his hand back and spanked even harder, her knees buckled and her stomach dipped under the impact “Count Sher!”

“Oooh, eighteen please!”

“Please what?”

“P-please give me another!”

By the time they reached twenty, she felt like she was just going cum. But she wasn’t quite there, Sherrie needed more to send her over the edge.

They continued until they finally reached twenty-five. Sheri breathed in relief but her punishment wasn’t over.

“Now what is this?” Maverick asked, pushing down on the butt plug Sherriehad forgotten about.

“My butt plug!” She answered, so factually, it was funny. There were laughs around the car and she felt heated, but that only served to increase just how turned on she was. Her Ass was warm and sensitive, she shivered when she so much as felt the AC blow on her skin.

“A plug?” Ezra asked aloud, casually moving it around inside her. “You dirty girl.” The men all came to some unspoken mutual agreement and flipped her back so she was sitting in her seat normally.

She winced slightly as her battered Ass cheeks touched the seat, but not as hard as she cringed when she came to and smelled her evident arousal in the air. They knew she was turned on by everything happening.

Ezra and Drew each grabbed one of her legs and brought them up so her knees were close to her ears, her heels grazing the ceiling of the car.

She gasped, four sets of eyes were all on her exposed Pussy, she added a fifth as she looked down to what they were all staring at.

Her Pussy was like a rose, all soft textured folds, looking so delicate yet longing to be harshly touched. She could see her hole come in and out of focus like it was winking every time she clenched it out of sheer horniness.

Alex brandished one of the vibrators, “Do you use this?” He asked. Everyone in the car seemed to lean in excitedly to hear her answer. She considered lying before realizing how futile it would be.

“Yes, I do,”

“Tell the camera what you do,”

Sherrie had forgotten about the camera set up on the dashboard. She looked into the lenses and said, “I use the vibrator and the butt plug.”

Drew nodded, “And tell them how you use it.”

Sherrie trembled, from shame, from arousal, from excitement. “I use it on my vagin-” She was cut off by Drew. He pulled her close and kissed her, softly but with such power, she moaned aloud, putty in his hands. He pulled away.

“Use your dirty words baby,” he brushed a stray curl out of her face with such care she forgot what he even said. “On…on my vagin-“

Drew slapped her Pussy, a loud wet sound. Sherrie yelped, body shaking from the impact, her handcuffs clacked noisily, she knew she had a safe word, but it felt so damn good.

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