How I met and had a fling with a neglected married woman

How I met and had a fling with a neglected married woman, Kay and I met by accident. She and her husband owned a small company which profits from the bounty of foodstuffs created in the Hudson Valley and I was a 2nd year culinary student who had some down time and ventured outside of the city for this small food expo that promised various ciders, cheeses, breads and other assorted food products given away for free after a small admission fee.

Since I was I broke, in my mid-20s, and paying my way through culinary school, the offer of quality all-you-can-eat food samples for a small admission fee and the chance to get out of the city for a day during a balmy, sunny NY autumn day was too good of an offer to pass up. I had a traveling companion in my buddy, Drew, and we hopped on the train and took the short journey north.

The food expo itself was…quaint. Amish pickles and preserves were mixed in cheeses from local creameries, along with various other non-food related businesses trying to hock whatever product they were making, but the real score at this event turned out to be the booze. Drinking in the city is expensive and daily alcohol consumption in my mid-20s was something of a foregone conclusion so I usually drank cheap, shitty beer at home to save money. But here, we were to find out, we could sample all the whiskeys and ciders we wanted for a small additional up front fee.

Drew and I were slightly buzzed as we shoved bread and cheese into our faces when a very attractive woman, who looked to be in her late 30s or early 40s, sat down at a table a few feet from us. We both glanced at her casually and continued our drunken banter. Drew and I never were good at filtering what we said in front of each other. Political correctness and decorum were things we saved for job interviews and conversations with girlfriends’ parents. They weren’t high on our priority list as we sipped bourbon and made dick jokes in public, and it wasn’t long before our antics of joke telling, laughing with mouthfuls of food, and general childishness had the attractive woman at the table a few feet away noticeably chuckling at our shameless immaturity.

I struck up a conversation and a few minutes later, I found out her name was Kay and she was here today on business. I even was handed the official business card with her name and company logo on it. We gave her the quick update on what us here today and apologized for our behavior, but she laughed it off and made it clear she wasn’t offended.

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My buddy and I excused ourselves as we had finished our snacks and bourbon and needed to acquire more sustenance. When we returned to our table, Kay had left and I thought nothing of it as we continued to enjoy our inexpensive food samples…until we started making our way through the makeshift parking lot back to the train station. I literally bumped into her again. No, seriously, I wasn’t paying attention to where I was walking (damn you, whiskey!) and walked right into her causing her petite frame to stumble backwards into a car.

I immediately apologized profusely and gave her a brief, sideways glance when she replied that she had something else in mind when she had told herself she had hoped to run into me again. I smiled and offered to buy her a drink to make it up to her. In response, she blushed and covered part of her face with her wedding ring-clad hand before respectfully declining. It was now my turn to hand her a business card of the restaurant in the city where I worked and I even made sure to jot down my cell phone number on the back and promised to make her reservation for her if she texted me in advance should she ever wish to come visit.

She blushed again at my forwardness and told me she might take me up on the offer.

I’ll spare you, dear reader, the boring details of what transpired the next few months and give you a brief synopsis. Kay and I started texting…a lot. These texts started, as they often do, with subtle flirting and ballooned into full on descriptions of explicit sexual acts.

I know it sounds cliche, (cliches do exist for a reason though), but Kay was the epitome of the neglected wife. Her husband’s sex drive had deteriorated to the point of a sexless marriage, but worse, the beginnings of his midlife crisis had made her an almost afterthought to him. I would come to find out she texted me not only to satisfy her desire to feel sexual again, but also just to have a male companion in her life. She would ask me questions about culinary school and what life was like in the big city for a Southern transplant. Her life of being an ignored wife, mother of two, and part owner of a small business didn’t allow her to have much excitement in her life. Thats when I began to really encourage her to come take a weekend trip to come see me. I pulled out all the tricks I could. I sent her photos of food I had cooked, nights out on the town I had with buddies from school, as well as other various things I knew would stimulate her mental and sexual appetites. She never said no, but she always seemed apprehensive for obvious reasons, while also outright stating she would love to come see me. Then it finally happened.

There was going to be some NY small business owner’s convention in the city which was designed for entrepreneurs to network and gain access to resources to help businesses build and expand. It was supposed to last five days. Her husband had no interest in going, but she convinced him it would be a good idea for her to go so she could have some personal time away from the kids and help the business at the same time. He eventually relented.

There was no way I could get five days of free time from school and work, but I made arrangements for two full days off and I managed a third night off after an early work shift. It gave Kay plenty of time to actually attend the convention and still have time to mix pleasure into her schedule.

****

Wednesday – The first day of the convention and her first night in town

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Normally when I’m in the kitchen, I have laser-guided focus. The heat, the fast pace, the endless synapses firing as I multitask five things at once while listening to orders being barked out and hollering my responses back in return are all things that simply happen seamlessly. Wednesday night wasn’t seamless. I couldn’t stop thinking about how excited I was to see Kay after work. I got yelled at more than my fair share that night for not having my head on straight, but I didn’t really give a shit. Funny enough, my sous chef made fun of me by implying I couldn’t focus because I hadn’t gotten laid in forever. I smirked to myself and continued to think about what the rest of the night had in store.

As I punched the elevator button for the appropriate floor of Kay’s hotel room, I clutched the bottle of red wine I had brought with me to help ease any nerves she and I might have and noticed this was a pretty damn nice hotel for a small business owner. I would eventually find out that Kay and her husband had plenty of money. Their small business was something he wanted to start after giving up a successful, but unfulfilling, career in finance.

*ding*

The sound of the elevator reaching its destination brought me back to reality as I quickly realized that only a hallway and door separated me from a night of (hopefully) sexual debauchery. I gave a gentle knock on the door and listened to the sounds of footsteps shuffling from inside, a short pause, and then the door unlocking and opening. Her head peeked out from behind the door, giving off a sense of nervous shyness. I combatted it with a big, smiling greeting and extending the bottle as a token gift. She invited me in and her nervousness was palpable. She made a few brief remarks about how thoughtful it was for me to bring her something and that she had forgotten how tall I was. I tried to put her at ease by teasing her about how short she was. In our previous texts, I had always poked fun at her for being short, and my comment was met with a glare of mock anger which I returned with a big shit eating grin.

I finally had the chance to get a good look at her. She had sent me sexy photos on a fairly regular basis but this was my first chance to see her entire body. She was wearing a rather modest, yet adorable, set of cotton pajama bottoms and a white t-shirt. It was almost bedtime after all. The fabric clung tightly to her petite frame. Her perky B-cup breasts filled our her shirt nicely and her flat stomach provided ample evidence of all the bike riding she was always talking about. She had trimmed her sandy blond hair since the last photo of her I had seen and she complimented me for noticing.

I pulled a wine key from my pocket (Always have the tools you need for the job. Chef’s orders.) and offered to crack open the bottle of French beaujolais. I served it in the finest of plastic hotel drinkware this establishment had to offer and after downing the first and her refill in short order, Kay was noticeably more relaxed. She even began to reach out and touch my arm as we chatted which, up until this point, was the most physical contact we had ever had other than that one time I accidentally shoved her into the side of a parked car. We both started to get more handsy as we became more comfortable in each other’s presence and when Kay excused herself to use the restroom, I decided it was time to make my move.

When I heard the faucet turn on, I walked to the edge of the bathroom and leaned against the door frame waiting for it to open. When Kay finally opened the door, she was slightly startled by my presence, but I didn’t give her time to dwell on it. I grabbed her wrist and pulled her into me. Now it was on. Having broken down the final barrier, Kay immediately initiated our first kiss. My hands instinctively began exploring her body. She kissed with me the passion and ferocity of a woman who had some serious pent up sexual frustration and I was a willing recipient of that frustration.

She broke our kiss and gasped momentarily as I quickly lifted her off the ground and pinned her against the wall. I held her in place with my hips and steadied her with one arm as my free hand wandered underneath her shirt. She began to breathe heavily and moan into my ear as my mouth moved across her neck and my hand found her sensitive breast. Her hands grabbed two handfuls of my hair as I continued kissing and nibbling on the soft flesh of her neck and ears. It was as if I could actually feel her body temperature rising as so much heat began emanating from her. When she moaned into my ear how much she wanted me, I made the executive decision that it was time to remove her clothing.

I grabbed a firm hold of her and walked her over the bed. A playful shriek escaped her lips as I gently tossed her like a toy onto the bed and stared at her as I ripped off my shirt and undid my jeans. She stared right back at me with a look of pure sexual desire as she bit her lip and waited for me. Leaving only my boxers on, I climbed onto the bed and her hand instantly reached for my cock which I playfully slapped away. She feigned shock before quickly realizing it was her clothing I was going to remove next. I tossed her shirt across the room and finally caught a glimpse of her 39 year old body with my own eyes for the first time. She was gorgeous and obviously took excellent care of herself. Her stomach was flat and her narrow waist flared out into some beautifully shaped hips. I pushed her back against the bed and began attacking her flesh with my mouth again. Her hands roamed over my back and shoulders as I kissed my way down her chest and across her torso. By this point, she was undulating her hips off the bed so I figured there was no longer any point in waiting. I slid further down the bed and grabbed the waistband of her pajama bottoms and she, as if perfectly synchronized with me already, lifted her ass off the bed to help me slide them off.

Though she had sent me plenty of sexy photos, she had never taken off her panties. This was the first glance I had ever gotten of her pussy. It was perfectly smooth, as if freshly waxed, and I could smell her feminine pheromones pouring out of her wet pussy. I wrapped both my arms around her legs and began covering her thighs and the soft skin below her panty line in kisses. She was soaking wet and started to breathlessly plead to me. I wanted to tease her, but I was also feeling impatient. I wanted to know what she tasted like. I positioned my tongue at the bottom of her wet slit, flattened it out, and slowly and deliberately dragged it across her pussy and up to her clit. Her thighs clamped around my head as my warm tongue took a second and third pass across her clit. She was gripping the sheets and taking long, drawn out deep breaths. My lips locked around her clit as I started to gently suck it into my mouth. My tongue flicked across that sensitive little nub every few seconds. By this time, her hips were coming off the bed, but I used the grip of my arms around her legs to keep my mouth firmly planted on her clit. I wanted this woman to cum her fucking brains out.

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My right arm released her leg, and I brought my hand up under my chin so I could a sink a finger into her soaking wet pussy while my mouth continued to assault her clit. She was so well lubricated, it slid in with ease. My finger immediately set to explore the inside of her deliciously tight pussy. When her moans became a shriek, I realized the pad of my finger had found that sensitive bundle of nerves on the roof of her pussy. I had her exactly where I wanted her now. She was going to be a mumbling, post-orgasmic mess by the time this night was over.

Her first orgasm hit her like an electric shock. Her entire body went stiff, her breathing stopped completely for a few brief moments and I could feel the muscles in her vaginal walls clenching even tighter on my finger before the dam broke loose. Seconds later, she was gasping for air and seemingly trying to rip the hair out of my head with one hand while dragging her nails across my shoulder with the other. Her pussy started gushing with her juices, and I had to hold onto her leg with left arm with everything I had as her hips bucked wildly off the bed. I doubled my efforts, darting my tongue across her clit faster, swirling my finger across her G-stop with a quicker rhythm until she hit sensory overload, and began shoving my head away from sensitive pussy.

She crawled away from me slightly and rolled onto her side, clutching a pillow while desperately trying to catch her breath. I looked over at myself in the mirror across the room and beamed with satisfaction at the mess of girl cum that was soaking my face and beard. I got up to retrieve a small towel from the bathroom and to clean my face up before returning to the bed. Kay’s entire body was flush but her breathing had begun to return to normal. She rolled over to face me and looked at me with heavy lidded eyes that were completely glazed over. She reached out her hand for me, the international body language sign for “Come here” as I joined her on the bed. She took the towel and wiped up the remainder of the gooey mess left between her thighs as she began to giggle almost hysterically. I pulled her into my arms and kissed the side of her face. She let out one last deep gasp as her giggling subsided and turned to look me in the eyes and flash a devilish grin. Her hand had found my very erect dick.

We began to kiss again as she stroked my dick through my boxers, but as she started to kiss me more aggressively, her hand moved underneath my waistband and she gripped me firmly. It was her turn to push me back onto the bed this time and remove my underwear. She grabbed my length with both of her hands and slowly stroked my shaft while her mouth went to work worshipping the engorged head of my cock. It was a funny time to remember a text conversation we had had a few weeks ago after she finally solicited me for a dick pic and I obliged. Kay had admitted she had slept with two guys in high school and two guys in college, one of whom was her current husband. She had confided in me after seeing the picture that she had exclaimed to herself because she had never a cock the size of mine before. Now, I’d watched enough porn in my life to know that I’ve got nothing on some of the pros, but since I was only the fifth guy Kay had ever been with, my ego inflated immensely knowing that the seven inch dick in her mouth was the biggest one she had ever given a blowjob to.

She used the perfect combination of hand stroking and mouth and tongue stimulation. I just laid back and enjoyed this exemplary blowjob and thought about how this was the perfect way to end a stressful day. Kay even used a hand to massage my balls while she continued to work my cock over with her mouth.

However, as much as I was enjoyed the sensations of her warm, wet mouth, what I really wanted to feel was her warm, wet pussy. I grabbed her arms and pulled her on top of me. She responded by smiling at me, knowing exactly what was going to happen next. My hands ran up and down her body enjoying the feeling of her soft skin against. My mouth went back to kissing her breasts and playfully dragging my teeth across her very erect nipples. Before I even realized what she was planning, I felt the unmistakable feeling of a wonderfully tight pussy enveloping the head of my cock. Immediately, an entire conversation of inner dialogue happened in an instant inside my head involving condoms, remembering Kay was on birth control, and seeing the daily pill dispenser in the bathroom when I went to grab a towel earlier.

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At that point, I’m not sure I would’ve been able to stop anyway. Her pussy gripped me like a vice and considering the look on her face as the head of dick slide inside her, she was also appreciating the sensation of being filled. Cursing was never something I’d ever heard her do, yet as she slowly worked more and more of my shaft into her clutching depths, a stream of delightful filth poured out of her mouth. For some reason, I loved hearing expletives being spoken with such a sweet voice. She almost sounded apologetic as words like “fuck” escaped her lips. Not only was it a huge turn on to feel all the sensations of having her body pressed against mine, but watching her face contort and the shy, nervous woman who answered the door earlier devolve into in a swearing a little slut who was trying to coax her pussy to accept more of my cock was almost enough to make me lose it too early.

Both of my hands grabbed her ass as we settled into a slow, steady rhythm and before long, our strokes were ending with sitting all the way down on my hips before rocking forward again, stroking nearly the entire length of my dick in the process. She felt amazing. How any man could ever neglect a woman with such an amazing body and a pussy that could barely accept the size of my dick is beyond me. All I knew is I was lucky to currently be the son of a bitch taking advantage of all the pleasure her body had to offer.

Her body adjusted to the size of the dick invading her pussy and our pace reflected that. To this point, our sexual interactions had been rather manic, almost animalistic in nature, but slowed down somewhat as we both needed a moment to gather ourselves. Now the pace was starting to pick back up and she seemed to relish being on top of me. She was alternating between bouncing up and down on my dick and sitting all the way down on me and grinding her hips into mine. It was a pleasure to watch her cut loose and when she reached a hand between her legs to rub her clit, I knew I wanted to see her cum again. My hands ran all over her body as I tried to stimulate every inch of her to help get her over the edge. I told her sexy she looked riding my cock and how good her body felt wrapped around me. Suddenly, she went from groaning in pleasure to a high pitched squeal and she reached out to grab the headboard above me to steady herself. I grabbed her ass and thrust as hard and deep as I could while her pussy spasmed all over my cock. I had never felt anything like it. It was as if her pussy was massaging my cock. Somehow through it all, I maintained my composure and got to watch this insanely sexy woman quiver and squirm as she rode out her second orgasm of the night. I loved watching how expressive she was, how she had allowed herself to cut loose and embrace the moment, and especially, how sexy she looked when her body went flush when she came.

Now it was my turn though. She had collapsed on my chest and I grabbed her and we both rolled over. She was starting to recover and I had started to stroke her wonderful pussy. At this point, I was so turned on, I could barely control myself. What started as slow, long strokes turned into a deep, hard pounding with each thrust punctuated by a squeal or gasp as I bottomed out inside of her. Her whole body was squirming underneath me and her face was contorted into something between pleasure and pain, but I was so driven by lust, I wasn’t going to stop unless she begged me. Even the fingernails clawing their way down my back only turned me on even more. This poor woman hadn’t gotten a proper fucking in god knows how long but she wasn’t going to be able to say that in the morning.

During more than one of our sexting sessions, Kay had made a point of bragging about her flexibility. I wanted to see what she meant. I leaned back and rested on my knees, the head of my dick still inside her, and pushed her knees back towards her shoulders. It was surprisingly effortless for her and it was obvious she hadn’t been exaggerating. With her legs pulled back, it allowed for an entirely different kind of friction and sensation which rubbed my cock just the right way. It drove me crazy. Her pussy felt like it was molded specifically to fit perfectly around me and I knew I couldn’t hold out for much longer. My strokes became more erratic as I got closer and it was clear that she noticed. Kay started playing with pussy again and begged me in her sweet sounding voice to cum to all over her. That sent me over the edge and as I pulled out of her, she quickly grabbed my dick and stroked me as I shot my load across her stomach and tits. Exhausted and satisfied, I collapsed on the bed next to her and after a brief clean up with the towel nearby, we both quickly drifted off to sleep.

Both of us had to wake up early to deal with our respective responsibilities but before we got dressed and parted ways, Kay surprised me and dropped to her knees to give me another fantastic blowjob before I could even pull on my boxers. We made plans to get together again either Friday night or Saturday morning before I left to catch the train to class.

Though our first meeting had been built up through months of flirting, sexting, and photo exchanges, the sex still managed to be even better than I anticipated. Now I was going to have to get through two days of work and school and somehow stay focused before I could have her again. It was probably for the best though. We both needed some time to recuperate.

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