Breaking Jessi Ch. 03

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

The dress was tight enough that it pushed my boobs up and together on its own, creating round swells at the top of my chest, which were obvious given the relatively low neckline of the dress. The other thing that was obvious, even with the dark fabric, was my hard, little nubs trying to poke their way through the dress.

"Panties or no panties," I asked the blonde slut in the mirror.

The black dress clung to my ass and hips in a wonderfully sexy way, and I didn't want to ruin that effect with panty lines. However, thinking about picking up a couple of guys with Sheri and the way I looked in the dress had combined to soak my pussy, and I was afraid that my juices would end up running down my leg if I didn't wear panties. So, I compromised and slipped on a tiny, black lace thong. I typically didn't like wearing a thong, but I was willing to make an exception to keep my ass looking good. And it worked—I had zero panty lines.

I snapped a selfie and sent it to Sheri. Seconds later, her response pinged in.

"Fuck, Ur hot."

"Stocking r no?" I sent back.

"U got black lace?"

"Fishnets."

"Fuck yes. Garter belt?"

"No. Don't have 1."

"I can bring 1."

"Would it show under my dress? It's really tight."

"Maybe. But U'd be xtra fuckable in just garter belt and stockings."

"Can I get a pic of U?" I asked, changing the subject.

"Nope. Gonna be a surprise."

"O, ok."

I put the phone down and concentrated on my hair. Normally, I wore it straight, but I teased it into waves then set it with hairspray. Next, I put on dark red lipstick, back eyeliner, black mascara, silvery-gray eyeshadow, and blush not much darker than my skin tone. The combined effect emphasized my eyes and lips without my makeup looking heavy.

Once I was satisfied with my hair and makeup, I found my black fishnet stockings and pulled them on. All that was left was my shoes, and there I had a choice to make. The practical side of me suggested my back pumps with a three-inch heel since I didn't wear heels often, much less to dance in. But instead, I pulled out and dusted off a pair of strappy, black platforms with five-inch heels and open toes.

I slipped into the shoes and realized that I needed to paint my toenails. And thinking about my naked toenails reminded me that my fingernails only had clear polish on them. Luckily, I still had time, so I picked out a nail polish nearly as dark red as my lipstick and applied it first to my toes, then over the clear polish on my fingernails. I knew it'd chip off my fingernails pretty quickly, but I figured it'd last the night.

It was just after 8:00 p.m. when my Uber arrived at my place. Not bothering with a jacket despite the cool air of the spring night, I stepped out the front door and nearly into Colton. For a moment our eyes met, then I looked past him and tried to walk around.

"Holy shit," he blurted out, not moving from in front of me. "You look incredible."

"Thanks," I replied, hoping my voice adequately conveyed my impatience. "Can you move? I've got to go."

"What? Oh, sure," the young man said, his eyes dropping as his face reddened.

For a heartbeat, I felt bad about brushing off his compliment, but when he stepped aside, I strode past and down the stairs. I felt his stare and knew he was looking at my ass, but I didn't turn back.

***

I arrived at the club a few minutes before Sheri. My driver, a man in his late fifties or early sixties, had tried to make small talk at first. I wasn't very good at small talk normally, and actually being on my way to the club had filled me with nervous energy, so I couldn't think of anything to say back to him. After a few minutes, he lapsed into silence. He did glance in the rearview mirror frequently, and even as preoccupied as I was, I noticed that he'd adjusted the mirror after I sat down, likely so he could look at the skintight material that covered my braless tits. But I didn't mind that. In fact, it was kind of a boost that he wanted to look, considering I'd been more concerned about the size of my boobs over the last few days than I ever had been before.

"I'm outside the club," I texted Sheri once I'd said goodbye to the driver.

"Almost there," she sent back.

I smiled, then heard an affected gasp. I looked up to see a group of guys my own age or a little older staring at me as they walked past.

"Hey, need some help getting in?" one of them asked, a smirk on his otherwise plain face.

"Nope. Waiting for a friend."

"Okay. Hope to see you inside."

A couple of his friends whistled, and one stuck out his tongue like he was licking something, then they were inside. But they had distracted me enough that I hadn't noticed Sheri arrive. The first clue I had that she was there was when I heard my name.

Turning, I saw the strawberry blonde and forgot to breathe. Her emerald green dress was every bit as tight and short as my own, but that was where the similarities ended. While it had thicker straps, the neckline plunged to below her large, round freckled boobs. Thins laces crisscrossed across the exposed flesh of her tits, keeping the dress together while revealing much of her.

"You like?" she asked twirling around and showing me that the sides laced up all the way from the bottom of the dress to her arms. It was clear that she was not wearing any underwear.

"Fuck yes," I breathed as she again faced me, a smile on her face.

My eyes drifted up from her amazing cleavage to her neck, where I noticed a choker the same emerald green color as her dress. Next to that choker, which accentuated her smooth neck, reddish blonde hair curled over her shoulders.

"Eyes up here, slut," Sheri laughed, and I met her gaze, noticing her bright red lipstick, pink blush, and green eyeshadow.

"The dress and makeup really bring out the green in your eyes," I told her, returning her smile.

"That's the plan."

"But I don't think anyone's gonna notice. You look amazing in that dress, especially your tits."

"Shit, so do you," the other girl said. "I can see how excited you are."

"That's only part of the story," I replied, too aware of how sodden my tiny G-string was. "You can feel the rest if you want."

A darker blush than her makeup spread across her face, and her nipples popped up enough to show through the fabric of her dress. I licked my lips, then held out my hand.

"Are you this worked up over me or because of what we're here to do?" Sheri asked as she took my hand.

"Both," I breathed, lacing my fingers between hers.

"Me too," she sighed.

***

I was two margaritas in and gyrating on the dance floor, not caring how bad a dancer I was. The margaritas relaxed me enough to be able to dance in my platform heels, but I wasn't so buzzed that I was at risk of losing my balance. The drinks also had left me even hornier than I'd been when I arrived. Unfortunately, neither Sheri nor I had found the perfect two guys. We'd both been hit on by several single guys, and even by a couple of groups, including the one that had talked to me when I was outside the club, but we were holding out.

"Maybe we could settle for one really cute guy tonight," Sheri yelled in my ear after getting my attention by grabbing my shoulder. "Like the tall blonde over there."

My eyes followed to where she was pointing. Just off the dance floor, a guy with the build, but not quite the face, of Chris Hemsworth stood there, beer in hand while he chatted with a couple of girls. But he was good looking enough, and he had a nice smile. Plus, I thought Sheri and I were way hotter than the two sluts he was talking to.

"Maybe," I said, biting my bottom lip as I thought about it. "I did kinda have my heart set on two guys. When Mark texted me earlier, thinking about that was what brought me out of a funk."

"Mark texted you?" the other girl asked, and I realized I'd been so taken with how she looked that I had never told her about the texts from my ex.

"Yeah, he wanted to know how I was doing."

"Fuck him," the strawberry blonds snarled. "Or better yet, let's fuck the tasty blonde guy."

"I think those two got him first," I pointed out as he walked away, his large hands on the small of the back of each of the girls he was with.

"Shit," Sheri groaned. "With hands like that, his cock must be long and thick."

I shrugged and didn't bother mentioning that dicks longer than seven inches weren't my idea of a good time. The few guys I'd been with who were longer than that had all hit my cervix when they fucked me, and that guaranteed a few uncomfortable, if not downright painful, moments.

"What about those two," I asked, pointing out a couple of guys a few feet away. The shorter of the two, a dark-haired and obviously well-muscled man a few years older than me, was dancing with a curvy blonde girl who was drunk enough—or pretending to be drunk enough—that she kept falling into him. His friend, who was tall and thin with somewhat shaggy, sandy blonde hair, danced with a plump brunette. Personally, I thought they were both cute and could do a lot better than the two girls hanging all over them.

"They're with those girls already," Sheri said, but I was already moving.

"Hey, want to dance?" I asked the shorter guy, noticing his sexy gray eyes and strong jaw as he turned to look at me.

"He's dancing with me," the blonde slurred, her somewhat soft, round features at odd with her harsh eyes.

"Shit yeah," he said, ignoring the other girl and putting his hands on my waist despite the fast tempo of the song.

Draping my arms around his neck, I pushed my groin against his as our hips swayed in unison. His cologne, a pleasant, spicy smell with maybe a hint of musk, filled my nostrils. It was a bit heavy, but I didn't detect any unpleasant odor underneath it.

"I'm Kent," he said, his soft, full lips close enough to my ear to make me wonder what they'd feel like on my neck.

"Jessi," I replied, hands in his short, dark brown hair, my eyes cast to the side where his former dance partner had grabbed her friend and stormed off.

"What the fuck, Kent," a male voice interjected, and we both turned to see his taller friend glaring at us. "That bitch was hot to go. Why'd you ditch her friend?"

"I'm hotter," I told him before Kent could say anything, and then I pointed at Sheri who had just joined us. "And so is she."

The tall man turned to look at Sheri, and I could see enough of his profile to tell that his eyes widened and his mouth fell open the moment he saw her. And he was not alone in his appreciation. Kent's eyes had followed my finger as well, and I thought they were going to pop out of his skull.

"Fuck," Kent said when he looked back at me. "You two are both way hotter."

"Thanks. I'm Sheri, by the way," the strawberry blonde said, first looking at the taller guy, then at Kent.

"He's Brad," my dance partner said when it became clear his friend had lost the power of speech. "I'm Kent."

"Hi Brad," Sheri smiled.

"Hi," the sandy-haired man finally managed as he and Sheri began to sway to the music together.

Kent glanced over at them, and I could tell from the angle that he was ogling Sheri's chest. I didn't mind that much, but I wanted his attention back. Tightening my hands in his hair, I pulled his face toward me and pressed my lips against his. After a moment, his lips yielded and he returned the kiss with vigor.

"Shit, you don't mess around," he said when our lips parted.

"Not when I see something I want."

It was true. My brain bugs had been all but dormant since we'd been at the club, and with this new development, they'd crawled off to oblivion, at least for the time being. But it was usually that way with me when I had enough alcohol in me, was horny enough, and found a guy hot enough. And in this case, I thought both Kent and Brad where hot, although Kent was doing more for me than his taller friend.

"Fuck," he said again, his voice heavy, when I squeezed his firm shaft through his jeans.

The song changed into an even faster one, and beside us, Sheri and Brad gyrated. For a moment, both my eyes and Kent's were locked onto the other girls bouncing tits. Then Kent returned his focus to me as his hands slid down my ass and squeezed it.

"That's a great ass," he said, gray eyes simmering. "Nice and round and tight."

"And smackable," I added.

"I don't doubt it," he replied, a huge grin across his face.

For the rest of the song, we danced together, eyes locked, his hands cupping my ass while one of mine played with his hair and the other rubbed his cock.

"Let's change," Sheri said beside us when the next song started.

"Sure," I replied, although I would have preferred to stay with Kent.

Brad was a little too wild a dancer for me, but I tried to keep up. His eyes, which were a pretty hazel, stayed on my tits as much as everywhere else combined. At first, this surprised me, as he'd been dancing with Sheri who had much more going on there than I did. But considering the attention he was giving me, I figured he must see something he liked.

At first, we didn't touch much or even dance really close to each other, so I didn't smell anything. But as we danced, I got a whiff here and there of a faint, clean scent. It was much more subtle than his friend's but just as nice. And as we moved closer during the song, the aroma grew stronger.

I gave Brad most of my attention while we danced, but every once in a while, I snuck a glance at Sheri and Kent, who were grinding away at each other. It looked to me that Kent's gaze was focused more on her chest than her face, which was the opposite of what he'd done with me. But I couldn't blame him, because I had a hard time not looking at her tits myself.

When the song changed once again, Sheri drew me away from Brad, grabbed my waist, pulled our bodies together, and kissed me, her tongue wiggling into my mouth. For a moment I was shocked by the suddenness of it, and the cloud of floral scent that enveloped us, then I relaxed and kissed her back, my hands grabbing her round ass.

"Holy mother fuck," Brad said while Kent, who had done most of the talking up until then, stared at us in silence, his mouth agape.

"So, want to take us home and share us?" Sheri asked the guys a few seconds later while I stood there trying to catch my breath.

Kissing the strawberry blonde in front of Kent and Brad, and the rest of the club too, may have been one of the hottest things I'd ever done with my clothes on. And my pussy knew it. The warm wetness soaking my thong turned cool as it trickled down my inner thigh, and the only sensation more intense than the quivers deep in my cunt was the tingling sensations emanating from my clit and my rock hard nipples.

"Then let's uber back to my place and fuck our brains out," Sheri laughed, and I realized I must've missed something, as I had not heard the guys agree.

"After you, sexy little girl," Kent smirked, and it took me a moment to realize he was talking to me.

I followed Sheri and Brad, who she was leading by the hand. Kent settled in behind me, and just as we were about to step off the dance floor, a sharp blow to my butt brought a yelp from my lips.

"You're right, Jessi," he said, much closer than I expected. "Your ass is very smackable."

***

Sheri sat in the front seat of the Uber while I sat between Kent and Brad in the rear seat. At first, I'd been surprised when she took the front and motioned me into the back. But then I'd realized she was helping me jumpstart the fantasy I'd told her about. And I was not about the waste that opportunity.

We'd only been on the road a few minutes by the time my dress was pulled down below my bare tits and pushed up to reveal my sopping wet thong. As Kent sucked one nipple between his soft lips, Brad pushed his tongue into my mouth and two fingers wiggled passed my black lace panties and into my dripping pussy. For a moment, I saw the driver—a Latino man who looked to be in his mid to late forties—staring at us in the review mirror, then he glanced at Sheri. She was telling him something, but I couldn't make out what she said over my own moans.

I turned to kiss Kent while Brad, his fingers now pumping in and out of me, lowered his lips to the breast Kent had not been worshiping. And as I moved, I saw Sheri lean over and start bobbing her head up and down over the driver's lap. At the same moment that it made its way into my lust-addled brain that she was giving him head, I realized the car had stopped.

"Fuck, Sheri's sucking off the Uber guy," Kent said, breaking our kiss.

"No shit?" Brad asked, raising his head to look, his fingers pausing their assault on my cunt.

"Oh, don't stop," I groaned, grasping Brad's hair and shoving his face back down to my tits. "Keep finger fucking me!"

Brad latched his teeth on one nipple and thrust his digits all the way inside of me. I squirmed and moaned, turning to kiss Kent again. Instead, He grabbed my hair and pulled my face down to his groin, where a thick, veiny cock stood straight up. My nipple pulled free of Brad's mouth, but I didn't care. He was still pistoning his fingers in and out of my slit while my lips wrapped around Kent's very suckable knob.

I took Kent as deep in my mouth as I could, but the angle didn't let me deepthroat him. Still, he didn't seem to mind, since he groaned and moaned and grunted as I slurped up and down the top half of his dick, his warm skin soft over the iron hardness of him.

With a cock in my mouth and fingers in my cunt, it didn't take long before pleasure ripped through me and my body tensed. I tried to keep sucking, but for several seconds the orgasm overwhelmed me. Once it was over, however, I fucked my face on Kent's now slick dick faster and harder.

"Did you just come on my fingers," Brad asked as he played with me still wet and definitely swollen labia.

I nodded, not able to look back at him because of Kent's cock in my mouth. It was then that I noticed Kent looking down at me with lust and something that seemed to be a mix of awe and contempt. That look sent a new quiver through my pussy, and I thought about asking Brad to fuck me right there in the car. But at that moment, two things happened that pulled me away from that thought.

The first was several spurts of hot cum filling my mouth without any warning. Eyes locked on Kent's, I sucked every drop out of his dick, swallowing it all without any escaping. At the same time, I heard the driver gasp then announce he was coming. My eyes flicked toward the front seat. Sheri's head did not stop its up and down motion, although it did slow, and I knew she was doing to the driver what I had just done to Kent.

"Shit, am I the only one not filling up some slut's mouth?" Brad asked.

"Jessi, suck off Brad," Sheri said, turning to look back at us after she sat upright.

"Sure," I purred, twisting so my back was to Kent.

Brad's face looked nearly as shocked as when he had first seen Sheri, but that didn't prevent him from feeing his dick. It was long and a little on the thin side, and I was worried how it would feel inside me. But the length wouldn't be an issue for a blowjob, so I pushed aside my fears and sucked and licked on the mushroom tip of his shaft.

The head of Brad's cock seemed to be really sensitive, because he was squirming, moaning, and breathing heavier and heavier as I swirled my tongue around it. Plus, after only a few seconds, he forced my face lower until the tip of his shaft hit the back of my throat. I gagged a little—like with Kent moments before, the angle was wrong for me to deepthroat Brad—but kept sucking and moving my tongue against his cock.

I'd been sucking on his shaft, gagging every time he pushed my head down further, for what seemed like at least a minute when I felt the car rock. I reached out to steady myself, and at the same time, strong hands grabbed my hips and pulled me around so I was belly down on the seat. My legs, knees pulled halfway up, were lying on Kent's lap, my tummy and tits were against the leather of the car seat, and my face was in Brad's lap.