The Kendra Chronicles

I will freely admit, this is a bit long-winded. However, as most authors state, this is building the character and relationship element. As a first installment, this is setting the groundwork for many more.

As always, please comment or leave constructive (not offensive or abusive) criticism, and thanks for reading!

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The idea of fucking a larger woman an is always on the forefront of a man's mind. It may not be good things that are going along with it, but it's always a curiosity. Will she be true to the stereotype and try to please you in any and all ways possible? Or will it just be a gross displacement of flesh and pancake boobs? It was this reasoning that had me inexplicably attracted to the now infamous Kendra. She was my gateway drug, and I have never once looked back.

I met Kendra at Oktoberfest, which is awfully fitting, given the rest of the story. She was one of the serving wenches, or barmaids as they were called in mixed company. Either way, she was one of many women serving beer and other German delights. They had thrown her in with a gaggle of large breasted small hipped women, either as a cruel twist of fate or because she was much more competent than the other ladies. I'm still not sure which, but the latter was definitely apt. She could carry a tray of twenty steins full of beer, and serve with the ease of a practiced surgeon. Meanwhile, the other women could carry maybe three steins and it was iffy if you'd get your entire beer.

I digress.

I was at the festival with a group of men from both work and university, all of which single. Well, save Matthew. He was recently engaged to a woman who looked like the women who would topple over from their tits being too large for their frame, and she was a bitch. I can say that with utmost certainty, and he knew it too. But apparently she was game for whatever he wanted to do sexually, paid for all of her own expenses, and could cook a mean roast. So he popped the question and she said yes, but he's been fucking women on the side ever since.

He was the first one to make a comment about Kendra, who was at the table beside ours in her sexy little outfit, her large breasts proudly on display in the tight corset-like bodice and off-the-shoulder blousy top. The skirts were relatively modest, hanging down to just above the knee, but the things she wore underneath made them fluff out most attractively, and if she bent down enough you could see the bloomers underneath.

Now, before I get too deep into this story, I'm going to give a bit of an explanation of Kendra's appearance. Reading into this, you've probably got the overly-large woman in your head. Quite the opposite. Yes, she's on the heavy side. But she carries it well, with large supple breasts that are still shaped like breasts, an ass made for slapping but doesn't jiggle when you do, and firm muscular legs with just a touch of fat. The only part of her that was less than ideal is her stomach, but that is easily to get past when you get a look at her breasts. Have I mentioned how spectacular they are? But, back to the story at hand.

Matt caught a glimpse of Kendra's generous cleavage and whistled appreciatively, nudging our friend Luke who was sitting beside him.

"Jesus, get a load of that," he said, sipping his beer and nodding towards Kendra. Luke grunted his assent and took a swig.

"I would like to get a load on that," he quipped, making the rest of us chuckle our appreciation. It was true, though. My curiosity of was piqued when I had seen her walking about before, smiling at the men at her tables. She had beautiful blue eyes and a head full of what looked like naturally curly blond hair, and one hell of a welcoming smile. I don't know why I was instantly attracted, but I was.

We continued to crack jokes about her, commenting on the way that she was able to fill out the beer wench costume more than the other toothpicks she was working with, and how her tables were constantly full of men. Henry, the guy sitting beside me, slapped his arm around my shoulders and proclaimed that I was going to sleep with her tonight. The other guys at the table hooted and hollered their agreement, getting louder and more rowdy the more I protested.

I had recently gotten out of a long-term, emotionally abusive relationship. Claire was just an awful human being, and I had tried my damndest to get out earlier. Thank God I hadn't been suckered into marrying that bitch. Either way, it had been several months since I last had sex, and my dick was definitely ready to get that ship back rolling.

"Just go talk to her, Sam. " Luke said, chugging back more beer and holding up his arm for another. I think he was hoping that the plump server would pick up our table as well, instead of the skinny snotty bitch that kept forgetting about us. Sure enough, the larger lady noticed and sauntered over, her breasts bouncing with each step. All conversation died at our table, we were all entranced.

"Yes, gentlemen?" she asked when she arrived, one of her plump hips cocked and a smile gracing her lips. I wanted to fuck that sexy mouth. Matt regained the power of speech first, which was surprising as he had drank the most out of all of us.

"First, we are in need of more beers," he said. The waitress smiled and jotted it down, using her eyes to count how many of us were actually requiring said beers. She was about to turn to walk away, when Matt caught her wrist lightly.

"Was there more?" she asked, gently disengaging herself from his grasp. Matt smiled at her, the charming smile that he uses to pick up the hordes of women that he sleeps with, and motioned towards me.

"This here is Sam. He is finally on the prowl after a year of being stuck with an awful bitch of a girlfriend. Would you do him the honour of sleeping with him?" he asked, causing the rest of the table to burst into appreciative laughter. The waitress joined in, obviously chalking it up to drunken camaraderie. "Is this true, Sam?" she asked, walking towards my end of the table. Playing along, I hung my head.

"Yes, ma'am. I'm wounded and I need you to nurse me back to health," I joked, pouting a little. I must have drank more than I originally thought. "I have just the cure," she said, leaning forward and giving me a spectacular view of those glorious tits before laying a firm kiss on my lips. I am blaming the alcohol for my instantaneous reaction, in that I felt the kiss all the way down to my cock.

The guys hooted and hollered some more, whistling as the waitress stood back up. The beer goggles may have been in place, but I still recognized an aroused woman when I saw one.

She backed away, cocking her hip again but extending her hand towards me.

"I'm Kendra," she said, directly to me. "And I'm done my shift in an hour,"

She bobbed what I would imagine is a bit of a curtsy at the table and said she'd be back with our drinks in a minute. My eyes, along with the rest of my buddies', were glued to her swinging hips as she walked away.

"This is the perfect way for you to get back into the game," Matt said, leaning his elbows on the table.

"How do you figure? There's any number of, how shall I put this politely, healthier women roaming around this festival," Luke said. The other guys laughed, and I couldn't help but smile at his phrasing.

"It's a known fact that, going with your phrasing, unhealthy women give it up faster and are better at it than the healthy women," Matt said, matter of factly. We all had a good laugh at this, but Matt was dead serious. He motioned for us to all lean in closer, keeping his eye out for Kendra's approach.

"Couple months back I fucked a fat chick that I met at that new bar on 5th. I wasn't really into her because, let's face it, I'm more of a lean and mean kind of guy. But fuck, the way she moved her body and did things with her mouth... I can't get Anna to repeat it no matter how many times we try," he said earnestly. "It's almost like they compensate for not being traditionally attractive by being exponentially better at all things sexual,"

Of course, that got us laughing hysterically again. Kendra walked up with our beers, a smile playing on her lips as she observed our good humour.

"Guten tag," she joked, placing a stein in front of each of us. "I am correct to assume that this is to be added to the tab you herr's had started earlier?"

Matt nodded and took a look at his watch, pointing out to me very obviously that Kendra's shift was over in 30 minutes.

"After we finish up with these, I'll make sure to stop by and pay it," Luke said, grasping Kendra's hand. Kendra smiled down at him. "With a generous tip, obviously. Does that warrant a kiss?" he asked. Kendra laughed and complied, kissing his forehead. We roared with laughter as Luke's expression went from euphoric to disappointment, and Kendra walked away laughing.

The next half hour was filled with nerves. It had been months since I had been with a woman, and a year before that since I had to impress one with my sexual prowess. The guys kept joking around and "giving me pointers" as it had been so long, but I wasn't listening to any of it. My heart was pounding and my palms were sweating. I didn't even drink the beer that Kendra had brought for me, hoping that I wouldn't throw up before it was time.

Sure enough, the hour finally came and the guys stood up, leaving me alone.

"I'm going to pay for yours tonight," Matt said, clapping me on the shoulder once more "But you owe me every single nasty detail,"

Tongue tied, all I could do was nod as I stared at the table. The guys laughed and left, giving last words of advice and manly shoulder slaps. I stared for a little bit longer, taking deep breaths and trying to remember all that calming yoga shit that Claire had made me do. I was lost in my own little meditative world when I felt a soft hand on my shoulder.

"Shall we go somewhere?" Kendra said, sitting down beside me at the table. I nervously smiled at her and nodded. She laughed softly, leaning in to hug me. She smelled like vanilla and felt like absolute heaven. Soft, squishy, delicious heaven.

"No need to be nervous, Sam. We're just going to get to know one another better," she said, standing and holding a hand out to me. Grasping it like a lifeline, I stood up and grabbed my jacket, allowing her to weave us through the crowd.

We stepped outside the beer tent and into the crisp night, the sky clear and filled with stars. The smell of autumn was all around, and it instantly both cheered and sobered me up. Autumn has always been my favourite time of year, with the warm days and cool nights and beautiful changes in scenery.

Beside me, I heard Kendra take a deep breath in and let it out slowly, sighing happily as she did so.

"I've always loved autumn," she said, linking her arm through mine. She rested her head on my shoulder as we walked a little further, and I felt complete. As ridiculous as that sounds, it's how I felt. A lady on my arm on a beautiful October evening, and the unwhispered promise of sex lingering in the air.

"Me too. Everything is so colourful and beautiful, the air feels cleaner despite everything shutting down for the winter," I said, covering her hand on my arm with my own hand. Kendra snuggled in closer.

"I have yet to meet someone who enjoys this season as much as I do," she said, chuckling a little. She led me to the parking lot, stopping at a shiny black two door.

"This is me," she said, leaning against the driver's door. I wasn't sure where she wanted the evening to go, so I leaned in for a hug. A harmless, friendly, "I just met you and my friends are douchebags" hug. Her soft breasts pressed against my chest as she wrapped her arms around me to reciprocate. I felt the warmth of her body and her cheek rest against mine... I'm going to say that the beer decided to kick back in, as I turned my head and met her lips with mine. A soft kiss, by all standards, but a kiss all the same.

I was about to pull away, embarrassed, when Kendra's mouth opened under mine, and her tongue made its way into my mouth. That one touch of her tongue to mine sent my arousal from somewhat dormant into hyperdrive and I greedily kissed her back. My hands went from her back down to grasp her ass and pull her closer to me, my cock racing to hardness as I ground against her. She dove both hands into my hair and pulled me closer, all but devouring my mouth. Thus far, Matt's theory of larger women was proving true.

We broke away, breathless, my hands still cupping her ass and her hands still grasping my hair. I leaned in to kiss her again, but she stopped me.

"We can't do this here," she said, moaning softly as I bent to kiss her neck instead. "Where do you live?"

"Anderson and 15th," I replied, kneading the firm globes of her ass and pressing my hard cock against her.

"Do you live alone?" she asked, fastening her lips and teeth to my ear. I shivered and felt my cock grow even harder, if that was even possible.

"Yes," I bit out, pressing Kendra against her car and ravishing her mouth once more. My heart was pounding, but not because of nervousness this time. I shifted one of my legs in between hers and she instinctively ground against it. I could feel the heat from her, even through layers of clothing. She stopped moving and pushed me away, gently.

"Let's go," she breathed, unlocking the door to her car.

We drove in silence, me trying to breathe my erection away and she keeping her eyes on the road like a diligent driver. I would quietly point out directions or short cuts, but otherwise we were both just caught up in our own internal struggle. We pulled up to my building, complete with doorman and valet, and exited the car with the utmost composure.

"Good evening, Mr. Blaine," the valet, Thompson, said, opening Kendra's door as I exited the car. The one thing I loved most about my building was the professionalism of the staff. Twenty odd floors of mostly bachelors in their 20's and 30's, and I had never once heard any gossip about what went on.

Kendra stepped out, acting as much a proper lady as she could in her beer wench costume, and thanked Thompson as she handed him her keys. She took my arm and I led her into the lobby, nodding towards the front desk clerk-slash-security man Howard. As per usual, I received a polite smile and a nod, and the elevator doors opened just as we walked towards them. To this day, I have no idea how they managed to always time the door opening.

We weren't in the elevator two seconds, the doors being closed for one of them, when Kendra had me pushed up against the wall, her mouth fused to mine and her hands clenched in my hair again. Knowing that the guys at the front desk could see all of this go down, I almost wanted to detangle her from me, waiting until we got into my apartment. But my body had a different agenda. My hands found their way to her ass, which I can't stop reiterating was both soft and firm at the same time and just great to hang on to, grasping tightly to pull her closer to my cock, which at this time was painfully hard.

The bell chimed, signalling our destination, and she backed away, her eyes twinkling. Had I mentioned that they were a beautiful, calm lake on a sunny day, blue?

Taking Kendra's hand, I led her out of the elevator and to my front door, fumbling in my pocket for the keys. It didn't help that Kendra deemed it necessary to help me, her hand slipping into the other pocket to stroke my cock through the fabric. Jesus.

I finally got the key in the lock, the lock turned, and the door opened. I all but pulled Kendra inside, shutting the door by pressing her against it and pressing my mouth to hers. I had just enough mental capacity to turn the lock before Kendra's hand pressed against my abdomen and slowly slid down, cupping my hard cock over my jeans and squeezing. My eyes all but crossed. I didn't think she was capable of the against-the-door fuck that I had playing on repeat in my mind, so I led her to my bedroom, never taking my lips from hers.

Kendra stopped as soon as we entered, asking me to turn on a night lamp if I had one. Willing to do whatever it took to get her into my bed (and get my cock inside of her), I complied and sat on the bed. Getting a good look at her, all breasts and curves and sexy costume, my jeans were getting way too constrictive. I'd never been so hard in my life. As I reached for the button and zipper, Kendra stopped me.

"I'll do that," she said, smirking. I wanted to protest, but she had moved her hands to the ties on her bodice, loosening them slowly. My mouth went dry as I watched it open, her breasts even more than I could even imagine, and she slipped the top and corset over her head. She wore a white lacy bra, a surprise because I thought all bras for large breasts were hideous things, her skirt and all things under it, and her shoes. I've never had a foot fetish, but the way that those shoes made her legs look... Damn.

"If you're a good boy, I'll take the rest of these off," she said huskily, trailing her fingers over her collarbone to play with the ends of her hair. It was like I was at the doctor's office and I was following the penlight with my eyes to determine if I had a concussion. Swallowing hard, I asked "What do I need to do?"

Kendra smiled.

"Just sit there and don't touch yourself or me, no matter what I do." She said. I nodded enthusiastically, thinking that I've gone six months without a woman I'm pretty sure I could go a little bit longer.

Why am I such an idiot?

Kendra reached for the zipper on her skirt, unzipping and letting the skirt drop. As previously mentioned, she was wearing some crazy pair of bloomers underneath. To a normal man, these wouldn't be any sort of turn on, but I was so sex depraved that my cock began throbbing insistently. The flesh on her stomach was a little more than I was used to, but my eyes just didn't rest there. She had softly predominant hips, and as she dropped the bloomers I noticed that her legs were a little disproportionate to the size of her stomach. But she was wearing the sexiest pair of thigh-high stockings I had ever seen on a woman before, combined with lacy boy shorts that actually helped to accentuate the best parts of her body.

Stepping out of the piles of skirt and bloomers, she slipped her shoes off, walking tip toed towards me. My mouth watered. Even the "healthy" women that I had been with before Claire hadn't put on this much of a show for me, be it one night stand or more.

She motioned for me to move further onto the bed, and I was all too happy to comply. She straddled my legs, pushing her crotch onto mine, and gyrated. My eyes rolled into the back of my head and my cock threatened to explode. I opened my eyes to a lace bra having a hard time containing the largest breasts I had ever had the pleasure of seeing, and I began to sweat. Kendra rolled her hips once again, leaning back a bit to get a tighter fit. My mouth went dry.

"You've been a good boy," she whispered, pressing her breasts against me and licking my ear. My hands fisted on the bed. "If you can take off my bra without wrecking it, I'll get you as naked as I am"

I moved my hands from the bed slowly, knowing how tricky bras could be. Deciding to give a bit of payback, I trailed my fingers along the outside of her thighs and up her back, using my full hand to slide down to her ass and push her against me a little tighter. I was torturing myself. Sliding my hands back up, I felt around the band of the bra for the clasp. Not feeling one, I knew that it must be one of the front-clasp bras that are both sexy and troublesome. Sure enough, Kendra moved back enough for me to see the clasp nestled into her ample cleavage. Fingers shaking, I went for the clasp, trying so hard not to grab and fondle the breasts it was holding hostage. Somehow, I managed to open it and Kendra pulled the cups of the bra away, setting her breasts free. I felt a bit of pre-cum ooze from the tip of my cock and also felt lightheaded. This woman was killing me with sex.