Small Town MILF

Disclaimer: This is a work of fiction concocted entirely within my imagination. Any resemblance to real people shouldn't be surprising since most of my stories are based on people I know. While I hope you enjoy this story and are compelled to provide feedback, I don't expect the subject matter will appeal to everyone who reads it. As such, I discourage venomous, nasty feedback full of violent wishes against essentially fictional characters in fictional situations. If this story does not appeal to you, there is undoubtedly one somewhere on Literotica that will, so your energy will be better spent on finding it rather than on vilifying me. Your opinions are welcome but your attacks are not.

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Small towns can be kind of funny when you're an outsider. In most cases, the people are super-friendly while, at the same time, you can feel like they're a little distrustful of strangers. With my job, I had abundant opportunity to witness this since I traveled a significant amount. I did quite a bit of flying but I did a lot of driving and the nature of my business took me to many small towns. There were times I felt like I was really welcome, times where I almost felt like a celebrity to people who were used to the same faces and the same places all week long and definitely times when I was anxious to get back on the road again. Don't get me wrong; I love small towns. I wouldn't have done what I've been doing for so long if I didn't. Of course, you'd be surprised how easy it can sometimes be for a stranger in a small town to get laid. It added to the feeling of being a celebrity when you encountered the "groupies."

It wasn't like you just showed up in town and the babes started throwing themselves at you but I'd developed a sense over the years that helped me figure out where to go and, once there, who might be open to an encounter with a stranger. They came in all shapes, sizes and ages, too. I'd spent passion-filled nights with single young ladies, older married women, skinny women, chubby women, attractive women and ugly women. Most encounters were memorable in one way or another but, of course, some stood out more than others. One of my favorites involved an older waitress at a bar in western Nebraska. She was a good looking woman, probably in her fifties, with a nice figure. The faded jeans she wore really showed off her sweet ass and she appeared to have a decent set of tits, too. I started out just being friendly since I was a stranger and waited to see her reaction before deciding whether it was safe to flirt or not. I did note that she was not wearing a ring on her left hand.

I was also careful to make sure I was friendly with the rest of the staff and the other patrons, as well, so I didn't come across as fixated and creepy. This was pretty much second nature, whether I was pursuing a lady or not, but it didn't hurt if I came across universally as a good guy. When I was comfortable that I'd received a stamp of approval from the locals, I did start to subtly flirt with the waitress I had my eye on and was pleased that she was not only receptive but started flirting right back. As the night went on, I was definitely getting a good vibe that she could be into some adult-oriented fun. Finally I just went for broke.

"So what time do you get off tonight?" I asked her.

"Why?" she asked right back, with a shy smile on her face.

"I'd like to eat your pussy until you cum," I whispered, making her blush. I'm sure she was expecting either that I'd be coy about what I wanted to do or that I'd just come right out and say that I wanted to fuck her. I really did want to devour her pussy and figured that offering it right up front would help get me in the door and, if I did a good job, would assure that things continued to progress. She had such a nice figure that I definitely wanted to get her naked, not just fool around out in my rental car. I also wanted to watch as her pretty face inhaled my cock.

She was only working through the dinner rush so she gave me enough time before she was taking off to close out my tab and head out the door so we weren't leaving together, then I followed her to a modest little home not too far away and parked behind her in the driveway.

"Are you okay with me parking there?" I asked as we headed to her front door, "You're not concerned with what your neighbors might think?"

"You take care of me tonight the way you offered to," she replied, "and I'll be out here pointing your car out to anyone who will pay attention to me."

I didn't expect her to follow through on that, but I certainly intended to follow through on my promise to eat her pussy and make her cum. Once we were in her living room, we were in each other's arms, making out passionately. My cock was stiffening so I suspected that her pussy was becoming wet, as well. Of course I had no idea how sexually active she was but I figured that her options in such a small town were probably limited so she might be a bit sexually frustrated and likely outright horny. I wanted to make sure to fully satisfy her, multiple times if possible, before indulging myself by slipping my cock into either her pussy or her mouth or both.

I ended up picking her up and carrying her over by her couch then set her down and dropped to my knees in front of her. I opened her jeans and slid them down, revealing a pretty non-descript pair of blue panties. As she stepped out of her jeans, I caressed her sweet ass through her panties while kissing her abdomen and upper thighs. After lightly brushing my fingertips over the front of her panties, I started to slide them down, revealing a nicely groomed brown bush. I ran my hands over her bare ass cheeks before continuing to slide her panties down to her ankles. She stepped out of them while I admired her bush then sat before me on the couch with her legs spread nice and wide.

I kissed my way up along her smooth inner thighs until I reached her bush, then ran my tongue up her slit, tasting the juices that were flowing from it. She moaned and grabbed my head, not pulling me against her pussy but just holding onto it. I lapped at her pussy, slurping up her nectar while she humped it rhythmically toward my face. I don't know if it was the anticipation or that she hadn't had any action recently, but I got a sense pretty quickly that it was not going to take much to get her to that first orgasm. I had no intention of stopping at one, though, so it didn't matter to me if the first one was immediate; I was planning to keep going. I slipped first one, then a second finger into her slippery pussy and pumped them in and out while licking and sucking her clit. It wasn't long before she started tensing up while continuing to moan louder and longer so I knew that she'd soon be right on the verge. I didn't necessarily want her to cum quickly; my goal was to provide her with as much pleasure as I could manage. When the tension suddenly left her body and she started to shake while crying out, I was certain that I'd achieved that goal.

I continued to eat her pussy as she was cumming and she didn't try to stop me once her long, intense orgasm had tapered off. She seemed to relax as she was catching her breath, but gradually began to rock her hips toward my face again. Her pussy had been flooded with additional lubrication when she came so I was slurping some of it up around my continually pumping fingers before focusing once again on licking and sucking her clit. Again I made it my goal to provide her with high levels of pleasure, not just to get her off again. Fortunately, I was a big fan of eating pussy, especially when it was a pussy I'd never eaten before. Because of that, I had a lot of experience and I tried to learn something from each experience. My philosophy had always been that it was a privilege just to be able to see a woman naked; to be allowed to eat her pussy or have sex with her was definitely not something to be taken lightly. I never wanted a woman to feel regret over the access she had granted me so I did my best to make sure the experience was memorable in a good way.

As I continued relishing the opportunity to eat her pussy, I could tell that she was building up to another orgasm. The signs were the same as they'd been previously -- the tensing up, the wetter, more engorged pussy and the longer, louder moaning -- so it appeared as though my techniques were successful, giving me no reason to change anything I was doing. It was only moments later that she started cumming again while I continued eating her pussy. Again, her orgasm appeared to be long and intense, just the way I always liked to serve them up, and again she didn't stop me once she'd apparently finished cumming. I smiled as I pumped my fingers in and out of her even more slippery pussy while licking and sucking her clit because I wasn't getting remotely fatigued or bored with what I was doing. I wondered how many orgasms she could endure without starting to lose it.

The final number turned out to be four. As I continued to eat her pussy while she was recovering from orgasm number four, she took my face between her hands, turned it up toward hers and started to sit up.

"My head is about to explode," she said before leaning down to kiss me. We made out for a minute or so but my cock was threatening to burst from my jeans, so I stood up and started to undress. I kicked off my shoes as I pulled my shirt up over my head while she straightened up and started to unfasten my belt and open my jeans. Once she had everything undone, she started sliding my jeans and underwear down until my cock popped out in her face. I took over sliding my jeans and underwear down while she took my cock in her hand and pumped it while cupping my balls. She licked around the head then wrapped her lips around it and slid them down. My jeans and underwear had only made it as far down as my knees but I had to stop and savor the pleasure of her mouth sliding up and down my tool.

She didn't suck me off for very long, I'm assuming because she still wanted to fuck me, but it was long enough for me to know that she had skills. After slipping my cock out of her mouth, she smiled up at me then helped me the rest of the way out of my jeans and underwear. I then stepped out of my socks as I took her hands and had her stand up, too. I raised her t-shirt up over her head, revealing a decent set of tits encased in a pretty non-descript white bra. I caressed her tits, feeling her hard nipples, then reached behind her and unhooked her bra. As I slid it down her arms, I admired her breasts, areolas and hard nipples before lowering my head to lick and suck her nipples while caressing the soft, smooth flesh of her tits. She moaned and ran her fingers through my hair, indulging me briefly before steering me toward the couch. She pushed me so that I ended up sitting on the couch, then straddled me. I steadied her by holding her waist as she reached for my cock and guided it toward her pussy. We both moaned as she lowered herself onto me and my cock was embedded in her hot, slippery pussy.

I ran my hands around to caress her ass as she started to move up and down, though my attention was drawn to her bouncing tits. As I watched them, I knew that my hands would not be content to remain on her ass for long. When she leaned in to kiss me and I couldn't watch her tits anymore, I brought my hands around from her ass to caress them. Our tongues were exploring each other's mouths while my hands explored the soft, smooth flesh of her tits and her pussy moved up and down my rigid tool. Her pussy felt absolutely outstanding which had me thinking that it was an absolute travesty that she wasn't getting laid on a regular basis. Of course I didn't know that for sure at that point, it was just a suspicion based on her bringing me home and fucking me so enthusiastically. If only any one of the local boys knew what they were missing. I suppose there were some that did as she must have had sex with somebody around there but I had to count myself lucky to be in the position where I currently found myself because if one of the locals was giving it to her, I'd have been out of luck.

The longer she rode me, the harder she was riding me, to the point where it was difficult to continue making out. Instead, she pressed her face into my neck, moaning longer and louder as her pussy was becoming even wetter and hotter than it already had been. I could feel an orgasm stirring within me but knew it wasn't likely that I'd be close to cumming by the time she did. Sure enough, it wasn't much longer when she dropped down on my cock and just sat there as a shudder passed through her. Since she'd cum repeatedly so easily when I'd been eating her, I assumed that she would just go back to riding me again once she'd finished cumming. I was more than pleasantly surprised by what happened instead.

"I'm going to suck your cock like it has never been sucked before," she told me once she'd recovered enough. She kissed me hard then climbed off of my cock and knelt on the floor before me. I just leaned back and watched as she took my cock in her hand and slowly pumped while leaning in to lick my balls. The feeling of her tongue caressing my balls felt outstanding and I could feel my cock growing even harder as she took her time and really gave them a thorough tongue bath. When her tongue finally left my balls, she was holding my cock so that her tongue could run up the underside all the way to the head where she licked and sucked just the head between her lips. Finally, holding the base of my cock in one hand while the other cupped my balls, she slid her mouth down my cock as I let out a moan.

When I thought she'd inhaled as much of my tool as she could manage, she paused and moved her lips down a little bit farther. She took her time and deep-throated as much of my tool as she could before sliding her lips back up again. Then she started to slowly slide her mouth up and down my tool while pumping the base and continuing to caress my balls. She left no doubt that she was a considerably talented cocksucker, which meant that she had to have gained her experience somehow. I wasn't really concerned about her background right at that moment but I eventually learned about, not only the years that she'd been married, but how she'd been saving herself for Mr. Right back when she'd been in high school. In any case, I knew that I was fortunate to have the opportunity to enjoy her skills and I was certainly appreciating them. In addition to being able to provide increasingly intense levels of pleasure, she was also drawing out the build-up without making me feel like she wasn't allowing me to cum.

She wasn't just bobbing her head up and down, either. She'd occasionally go back to licking my balls while pumping my shaft or running her tongue around the head of my cock. I wondered if, like me when I was eating her pussy, she was getting as much enjoyment out of sucking my cock as I was getting out of having her suck it. I would have been perfectly content to have her spend the rest of the night with my cock in her mouth but, eventually, she seemed to focus more on bringing me to orgasm rather than drawing out the pleasure even further. Turns out that I was perfectly okay with this, as well, as I savored the build-up to my orgasm. My cock grew even thicker the closer I got to cumming, but she never let up at all even when I started to spurt into her mouth.

She continued to suck me off even as she was swallowing down my load while I felt as though I might never stop shooting into her mouth. When I was finally spent, she let my cock fall from her mouth and smiled up at me.

"I'll wake you up with another one just like that if you want to spend the night," she offered. It wasn't all that late at that point, but it didn't take any convincing for me. We retired to her bedroom where we went at it for a while longer before we fell asleep together.

I woke up briefly a few random times during the night but I was up for good, in more ways than one, when there was light trying to sneak through the blinds. There was a warm mouth sliding up and down my rigid tool, which has got to be one of the best ways to wake up. I lay there savoring it for a little while before she realized I was awake. She continued for a little bit longer, whether because she'd promised or because she wanted to I don't know, then crawled up to straddle me. I reached for her tits as she guided my cock to her pussy and lowered herself onto it, causing both of us to moan. I was caressing the soft, smooth flesh of her tits and toying with her hard nipples as she slowly rode my cock while the room continued to grow brighter. Her pussy was as incredibly hot and wet as it had been the previous night so it felt fantastic as my cock slid in and out of it.

As she gradually increased her pace, her pussy was feeling even hotter and wetter than it had been when it had first engulfed my throbbing tool. She'd dropped a hand down to massage her clit as she was riding me, so I assumed that was helping with the amount of pleasure she was feeling in addition to my cock. I was pretty engrossed in her tits, either fondling them or watching them bounce when I ran my hands around to caress her sweet ass. With the room becoming much lighter, I was able to admire her entire body as she loomed over me as well as observing how attractive she was even first thing in the morning. Once again, I was counting myself lucky for the opportunity to be with her at that moment, experiencing the pleasures of her body. As I've said, I've had the good fortune to score pretty often in my travels, but this was definitely one of my more memorable and cherished encounters.

When she dropped down hard on my cock and remained there as her entire body trembled and she let out a cry of pleasure, I was happy that she'd been able to cum again. I just waited to see what she wanted to do next while watching the expression of intense pleasure on her face.

"I'm going to finish sucking your cock now," she announced as she opened her eyes again.

"How about letting me lick your pussy while you do?" I asked.

"Absolutely, lover," she replied, then leaned down to kiss me. We made out for a minute before she climbed off of my cock and moved around to position her pussy over my face. I immediately slipped a couple of fingers into her while she started pumping my cock as she licked around the head. I wanted to admire her pussy at close range again momentarily before putting my tongue to work but, at about the time that she engulfed my tool in her mouth, I started licking and sucking her clit. The small bedroom was filled with the sounds of moaning and slurping as she sucked my cock and I ate her pussy. I was focused on providing as much pleasure to her as I could but not so focused that I couldn't appreciate her oral skills once again. I think even at that point I was realizing that I didn't want this to be a one-time thing with her. She was not only skilled, but enthusiastic as well, and I had a strong desire to continue experiencing that combination.

As appeared to be typical for her, the longer I licked her clit and fingered her pussy, the wetter and more engorged her pussy became. I could feel my own orgasm building, as well, due to her oral talent but I was pretty certain that she was going to beat me to the punch yet again. I was perfectly okay with that, obviously, especially if it meant just lying there after she'd cum, staring up at her pussy while savoring the feel of her mouth on my cock. I didn't push to try to make her cum sooner just so I could experience that; I remained focused on providing as much pleasure as I could. Plus, as I've said, I'm a big fan of eating pussy, so I would have been more than content to continue eating her even if she hadn't been sucking my cock.