The Affair with Kelly

For the past eight years or so, I've taken the daily commuter train from my home in the suburbs to my office in the city. Over the course of that time, I've gotten to know a number of the regulars I see on a daily basis. It almost feels like a family at times, all of us sharing in the occasional delays, bumbling tourists, and other peculiarities that one of my friends described as the joys of public transportation. I noted that the groups of people who tend to congregates at specific spots on the platforms to await the arrival of the train seem to be the closest. Maybe it's because they not only have to deal with those joys of public transportation, but also share in the experience of waiting in the weather, be it the biting north wind of winter, the stickiness of summer, or the rain and snow.

Anyway, the group that I've fallen in with on the platform consists of six people, though two ladies and I are what I would call the regulars of the group. One of those ladies, Michelle, is an older lady, probably in her mid 60s, who despite some serious health issues, refuses to retire. The other lady, and the subject of this story, is Kelly. When I first met Kelly a couple years ago, I thought perhaps she was in her late 30s, maybe 40 at the oldest. I found out, however, that she was in her late 40s. To say that she looked good for her age is an understatement. But as I discovered over the next couple years, her attractiveness went far beyond her blonde hair, blue eyes, and tasteful clothes that accentuated her curves. Her personality was amazing, too. She was always smiling, was witty with a great sense of humor, and seemed like she always had something nice to say about people. As you might be able to tell, I had a bit of a crush on her from the start, though I never really thought too much about it, especially when I found out that she was married. What I did think about was how hot she must have been 20 years ago! And those fantasies provided more than a few masturbatory sessions over the years.

One day after work a couple months ago, I got up to the train platform to find Michelle and Kelly already engaged in conversation. They both work at the same place, though in different departments, so I've noticed they will talk shop or share gossip. They were talking about some guy that I heard Michelle refer to as a "ladies man." Michelle claimed that all he did all day was walk around and flirt with women.

"Yeah, I've heard about that guy," Kelly replied, "but I'll tell you that he's never flirted with me. To tell you the truth, Michelle, nobody really flirts with me anymore."

Both ladies laughed and then, for no good reason, I butted into the conversation, saying "well, Kelly, if you ever need or want somebody to flirt with you, look no further then right here," tapping my chest for emphasis. She blushed a little and thanked me as the train pulled into the station. We boarded and went to our respective seats, which were spread out through the car. An hour or so later, we arrived at our station.

As I walked down the steps from the platform to the sidewalk, I heard Kelly ask, "Hey, do you want a ride home?" I politely refused, thanking her and stating that it was only a short walk and a very nice afternoon. She smiled and said, "Just thought I'd ask. If you ever need one, let me know."

As I walked home, I couldn't help but think that perhaps I had just made a huge mistake. She never offered me a ride before I made that comment about flirting. My overactive imagination kicked into overdrive, and before I was at my front door, all sorts of lurid sex scenes were running through my mind.

A couple weeks later, I was waiting on the platform, ready to head home after what seemed like an endless day at work. I heard the tap of high heels behind me, and instinctively glanced over my shoulder to catch a glimpse of what I hoped was a young hotty.

"Hi," Kelly greeted me. "How was your day? No Michelle today?"

There was an awkward pause as I fought to regain my composure. "Uh, yes, Michelle said she had to leave on the earlier train for a doctor's appointment. My day was long, how about yours? And by the way Kelly, you look absolutely stunning!" She was wearing a slinky black dress that clung to her hips and really showed off her ample breasts. My only complaint would've been that the dress was a little long, going a couple inches below her knees.

"Ah, I bet you tell all the ladies that," she laughed and, something she'd never done before, lightly touched my shoulder. I'm not ashamed to admit it that her touch made my heart flutter. I scolded myself for acting like a kid in high school. "All I know, she said, is that I hope we get home on time. There's heavy rain forecasted and I'd like to get my grocery shopping done before it hits. Now, I've got to get out of these heels; my feet are killing me!" she sat down on one of the benches and removed a pair of flats from her bag. I watched in fascination as she slipped out of the heels, and leaned forward to put the new shoes on. Of course, leaning forward gave me a great view of those big beautiful tits, and I couldn't help but gawk. She looked up and smiled, clearly I had been caught looking.

For a majority of the ride home, I pondered my situation. There certainly did seem to be some sexual tension between us and I felt like a couple of the glances and the touch on the shoulder had been signals of some kind, but I honestly had no idea what she wanted or how far, if at all, she wanted things to go. We arrived back at our home platform and just as we disembarked from the train, the skies opened up.

"You're not planning on walking home in this, are you?" she asked as we stood in the shelter of the parking garage.

"I'm going to wait a couple minutes and see if it calms down. If it does, I'll be fine."

"Well, I'll wait with you. I don't want to get all the way home only to have to turn around and head back out to the store."

We waited for about five minutes or so, just making small talk, but the rain didn't let up. "Doesn't look like it's going to stop any time soon, she informed me, looking at the weather radar on her phone. "Come on, I'll give you a ride home."

" Are you sure? I don't want you to have to go out of your way."

"Yes, I'm sure, now come on!" She grabbed my hand and nearly dragged me to her SUV.

"Well, doesn't look like I'm doing my shopping today. I can't stand to go in the rain." she said as we waited at a traffic light. "This rain is crazy!" She nearly had to shout to make herself heard above the pounding rain.

I nodded in agreement, and then decided to tempt the hand of fate by adding a little inuendo to see how she responded. "It sounds like you don't like to get wet," I offered, admittedly a bit shily.

"Not true at all. I don't mind getting wet, the timing just has to be right. And with that, she lightly touched my knee. Not only did she touch my knee, but she left her hand there. And if that wasn't enough, as the light changed to green, gently slid her hand up toward my thigh. I reached over and put my hand on her knee.

"I saw how you looked at me today when I came up on the platform. I have to say, I haven't had a guy look at me with that kind of look in a long time. And, if I may be so bold, it really turned me on."

"Sorry," I replied, "but you really are stunning. Of course, I have a thing for dresses and skirts, so I might be a bit biased, though in your case, I don't think so."

"Ah, I'll bet you like skirts and dresses because of easy access, right? She giggled, and as she did, she pulled up her dress a bit. Nothing too crazy, just a couple inches, but the signal was clear.

I took a deep breath and slid my hand from her knee, up her leg toward her thigh, stopping when I got to the material of her dress, which was about four or five inches above her knee. We were now sitting in front of my house, the rain still pouring down. She put the car in gear.

"You can go further than that if you'd like," she said. She leaned back into the seat, pushing her hips forward a little, and spread her legs a bit. I slid my hand under her dress and between her thighs, lightly brushing the silkiness of the panties that covered her pussy. I slid a finger underneath the edge of her panties and gently eased it between her outer lips.

"My God that feels good," she breathed. "I want more, but not here, somebody might see. If you're up for it, let's go to my house. My husband won't be home for a while, so we can stop fooling around like teenagers!"

We pulled into her garage and she shut off the car. Now that we were out of the storm, the silence was deafening. Neither of us said anything for a couple minutes, just continuing to touch one another, me fondling her tits and sliding a finger or two into her pussy, and she rubbing my hard cock through my pants.

"Now what?"

"Now, I want you in the back seat of this vehicle, with no panties on and your legs spread wide open, so I can have easy access to your delicious pussy." Without a word, she hopped out of the driver's side and climbed in the back. I followed, still in disbelief that this was actually happening.

"Kelly, I can't tell you how often I've dreamed about how it would be to stick my tongue in your pussy and taste your wetness."

"Hurry up before you lose your chance. You're driving me crazy and I need to cum!"

"And after I fuck you with my tongue, I'm going to suck on your pretty pink clit, give it a nice massage with my tongue, and make you cum all over my face."

"Shut up and put your fucking tongue in me now! I need to feel it."

I pulled off her panties and threw them on the front seat of the car as she pulled up her dress around her hips, spreading her legs wide. Kneeling on the floor of the back seat, I moved my face a couple inches from her neatly shaved pussy, breathing in the delicious aroma of her wetness and the lotion she wore. I trace the outline of her pussy with my tongue, gently licking and exhaling my hot breath. I flicked her clit with the tip of my tongue, opened my mouth wide and sucked on the lips of her pussy.

"Stop fucking teasing me," she wined, slapping me playfully on the head.

I wanted to give her what she wanted, but quite frankly, I was enjoying hearing her beg. I lick from the opening of her pussy up to her clit and back down, finally pausing to slide my tongue inside to drink up her delicious wetness.

"Yes! That's what I like! Fuck me with your tongue!" she exclaimed,

After a minute or two, I moved my mouth up to her clit, sucking it into my mouth and massaging it with my tongue. "Yes! Yes! Keep licking me right there!" she said, firmly putting a hand on either side of my head to make sure my warm wet tongue didn't move from that magical spot.

"My god, that's it. Keep licking me! I forgot how good oral sex is!" she squealed. As best she could in the confines of the back seat, she arched her back and bucked her hips, trying to fuck my face. Faster and faster, she rocked her hips, grinding her clit against my tongue and lips, moaning with delight as I continue to lick and suck. I slid two fingers inside her dripping pussy, moving them in and out.

"Oooh Baby! I love your fingers inside me! Make it three fingers, I wanna be filled up! You're gonna make me cum! I'm gonna squirt all over your face! Fuck that tight little pussy with your fingers! "God, Baby! That's soo good! Keep going, I'm going to cum!"

She slammed her thighs closed around my head and arched her back one final time, letting out a sing-songy scream that sounded like some kind of premortal song.

By this time, my cock was aching and I was in desperate need of release. She opened the car door and got out, looking back at me with a rather devilish smile. "We're not done yet, but you're going to have to catch me if you want dessert." Before I could say anything, she stripped off her dress and bra, leaving both on the floor of the garage. She stood there completely naked except for her shoes. She was just gorgeous, long toned legs, a beautifully shaped ass, and perky tits with erect nipples just begging to be sucked.

She took off running into the house. I struggled out of the car, retrieved her clothes, including the black silk panties that I stuffed in my pocket, and headed inside to find my hot little vixen, my bulging cock begging for relief.

I caught a glimpse of her running up the stairs, but lost sight of her as I reached the top. The sound of a slamming door gave me a clue which direction to go, and when I opened it, there she was, in the middle of a king-sized bed, on her hands and knees, looking at me with a big smile.

"Undress now." She commanded, "I need to see your cock." Obviously, I did as I was told, glad to finally have my cock released from its prison.

Now come closer, to the edge of the bed, I need to get a close up view. Very nice, she said, and before I could react, took me deep in her mouth. Much to my consternation, she only kept her big beautiful lips wrapped around my cock for a minute, and I had to fight every impulse to grab her blonde hair and pull her back down to my throbbing dick.

"Just so you know so you don't get your hopes up, I hate giving oral, especially to completion, but I did want to at least have a quick taste. Sorry, I just think the taste of cum is disgusting. Now, it has been so long since someone has fucked me from behind, and it has always been my favorite position, so you are going to climb up on this bed and shove that dick inside me."

Of course, I complied, positioning myself behind her and revelling in the anticipation of finally sliding inside her pussy. "Actually, wait, before you put it in, smack my ass," she commanded. "Not like that; I mean hard! Make it sting baby!" I did as instructed and she yelped in pain. "Now give me it. Give me that cock!" she growled through gritted teeth.

We fucked hard for the first minute or two,she driving her hips back and me thrusting forward. Then we slowed, just barely moving.

"You know, you can try the other hole if you'd like. I'm sure we have some lube around here and I haven't had that hole filled in even longer."

"Wow, you like anal?"

"I do, on occasion. Is there something wrong with that?"

"Absolutely not. But let's save that for another time," I suggested. "I'm perfectly happy with enjoying your amazing pussy."

"Oh, and how do we know there's going to be a next time?" She teased.

"Just a feeling," I said, wrapping my arms around her and grabbing her tits.

The intensity picked up again and I felt my balls about ready to explode. I couldn't help myself; I moved one hand to her hip and reached up and grabbed a handful of her long blonde hair with the other.

"Pull it and pound my pussy! Make me your little cumslut! Yes! Yes! Yes!" She panted, "make me cum again!"

I told her I was going to cum. "Good, give me that cum! Fill my cunt with your load!"

"Oh my God Kelly!" I grunted. We both erupted, me blowing the largest load I've shot in a very long time into her pulsing pussy. We collapsed on the bed, snuggling together as our breathing slowed.

"Thank you for an awesome afternoon," she said sleepily, "I haven't had that much fun in a very long time."

"And thank you for making one of my fantasies come true."

"You mean you've fantasized about me?"

"Absolutely. I told you, you look stunning. And that's not just today because of that dress you had on. I've always thought you were extremely hot. Why do you think I made that comment about flirting with you a couple weeks ago? I wasn't joking."

"You're very sweet. And, Yes, I can assure you that this isn't going to be the last time that we have fun. Jeff, my husband, is fifteen years older than me, and he's not in the best of shape. Which, of course, carries over to the sex department as well. To be fair, he used to be more than able to keep up with me, but the last year or so some pretty serious health issues have gotten in the way. Unfortunately, at least for him, my drive hasn't slowed down much, and I've been struggling to find ways to satisfy my needs. You know, a girl's got to do what a girl's got to do. Sex toys just don't do the trick, at least for me."

"I completely understand, nothing beats the real thing. You just tell me when you need me and I will be happy to help address any of your needs."

"That reminds me, he should be home in about fifteen minutes, so you'd better go. I don't know how he'd react if he found out that someone was here playing with his wife's pussy."