Footsie on a plane led to [m]ore [f]un later.. [MF] [Cougar] [MILF]

Footsie on a plane led to (M)ore (F)un later…

This is my first time posting here so let me know if you are interested in reading more. Will do my best not to embellish these stories but keep in mind they are from memory – though this one was recent.

A bit about me. I am 28 and in pharmaceutical device sales. My job keeps me on the road quite a bit and the majority of the stories I have are from various road trips. I have been told I am good looking but consider myself about average. Just under six feet tall and in relatively good shape, though no six pack (working on it). Brown hair, brown eyes. In any case this encounter happened about two weeks ago. The setup is a bit long but then again I like stories here with good setups, but by all means feel free to skip to the “good” parts.

I was flying home on a Monday morning from a sales conference and as I sometimes do was boarding my flight last. Immediately in front of me were two co-workers, a woman and man who appeared to be in their late 40’s to early 50’s. As we approached my seat they sat in the row immediately in front of where I was to be seated, but since I was the last on the plane I “opted” for the middle seat, specifically so I could sit next to the woman who had boarded.

I tend to be a little taken with older women (more on this later). Karen (later learned her name) was not what I would call amazingly attractive, certainly not the airbrushed MILF type with fake breasts and botoxed lips, but she was the kind that caught my eye. She had shoulder length brown hair and curvy hips and a recent manicure that told me she took good care of herself. What really attracted me was her outfit – a cute skirt, sleeveless tank with sexy black boots. As I sat down I noticed a black bra strap innocently peaking out of her shirt.

The body language between us was immediately good. She sat down and crossed her legs towards me and I stretched out my legs so that my calf was resting against her foot. At this point any contact could have simply been incidental given the tight foot room on airplanes. But after several minutes of contact it was clear that we were both aware of the others presence. At takeoff she uncrossed her legs and moved her foot away. At this point I thought things were over. I am not one to sexually assault unassuming strangers and unless she initiated more contact I wasn’t going to force the issue. About thirty minutes into the flight I noticed her co-worker was asleep and soon after felt her foot come to rest against mine again. She began bouncing her leg, I responded and we were off and running. I had my shoes off at this point, unfortunately her boots stayed on but there was progressively more and more touching. Knees, elbows, arms, etc. Given the lack of blankets on planes these days it was clear it wasn’t going farther but there was certainly mutual attraction. I had become aroused and at one point noticed her glancing at the bulge in my pants which I was making no effort to hide. Towards the end of the flight she had her leg basically crossed over mine and with my hand strategically placed on my knee I was gently caressing her exposed thigh. We began our descent shortly thereafter, her co-worker waking up with the pilots announcement. As our tray tables went up our feet separated and I thought, “well that was fun.” We chatted very briefly as we made the approach (we literally had not spoken to this point.) I asked how long she was in the city, etc. – innocent plane chat and learned she would be there for 24 hours. On a whim, and while her co-worker wasn’t looking, I wrote my phone number down and simply said – if you need any restaurant or bar recommendations just let me know. It was enough to be subtle and leave the ball in her court. As we deplaned I honestly didn’t expect to hear from her again.

Around 2PM I received a text from a number I didn’t recognize. It said – “Hi, this is Karen, we met on the plane – my co-worker wants to go get BBQ, do you have any recommendations.” This was the first I knew her name and while the message was innocent the fact that it opened up conversation was a step in the right direction. My hometown is known for it’s BBQ so I sent her my top three places and then added “need any company.” I then began obsessively watching my phone – when I hadn’t heard anything by 4 I figured, once again, things were over. She simply responded back and said “Can’t do company at dinner – sorry.” And then five minutes later a second text, “grab a drink later.” At that point my pulse shot up and I responded with a quick yes. She said dinner was expected to go late but she would text me after. By 9PM I still hadn’t heard and my hopes were once again beginning to flag. When she texted and said, “dinner just finished and I have an early flight but if you want to have a quick drink I am at the airport Hilton and they have a bar.” I was in my car before I could even respond and to the hotel twenty minutes later.

I approached the bar and noticed Karen sitting there with a glass of red wine. She hadn’t changed since I had seen her that morning so I simply asked “long day.” “Long but good she said, and better now.” That was certainly a good sign. We chatted over drinks, I learned her age – 49 – that she had been divorced for six years and had two teenagers at home. While we were drinking we once again were in contact. Her hand resting on my arm, legs grazing each other – still I didn’t know if this was mere flirtation or going to become something more. By her second glass of wine she was becoming quite a bit more open. I learned that she had only slept with two men since her divorce and she was giving me a hard time about our age difference. At that point I was buzzed enough to say pretty bluntly – “care to make it three?” At that point she became almost nervous, saying she had never been with a younger man and wouldn’t compare well to women my age. I rested my hand on her thigh and gently pushed just under her skirt and said “let me be the judge of that.” She said, I’m in 421, give me five minutes.

Let me say at this point I know a lot of young men are interested in older women for what they can “learn” and I have certainly had some amazing experiences along those lines. However knowing her background and talking over drinks it became pretty evident I was more “experienced” then Karen. And as I walked up to her room I told myself, this night is going to be all about her, she isn’t going to know what hit her…

I knocked on her door and she let me in. She was still wearing the skirt and sleeveless top but the boots were now gone. A quick glance and I noticed her toes matched her fingernails. “I have been dying to see those toes since this morning” I said. She just responded “oh really.” I pulled her against me pressing my bulging pants into her and whispered in her ear “and I know you have been wondering about this” which elicited only a moan. I began to kiss her neck pulling her harder into me letting my hands fall over the curve of her beautiful ass then moved the kiss her directly – an almost electric charge escaping as our tongues touched and danced for the first time. My eyes glinted “I’ve been hard all day thinking about you” I said as I took her hand and placed it over my bulge which she squeezed with widening eyes… “that is for later” I said with a wink. I led her to the bed and said “I know you have an early flight – but are you ok if I take my time” to which she responded “you can do whatever the hell you want!”

I laid her down on the bed and said – “you know since it was a game of footsie that started this whole thing why don’t we just pick up there.” I took her feet in my hands and began massaging them then slowly took her toes into my mouth one by one, letting my tongue caress them, sucking them. She later told me no one had ever done this to her. I kissed the soles of her feet then began slowly making my way up her leg. I have found there are a lot of tender spots that are often overlooked by most men and I wanted to hit all of them – the inside of the ankle, behind the knee, the inner thigh. I trailed by fingers over each of these, nails gently scratching the skin and following that sensation with my tongue – kissing, flitting over all of her. I pushed her skirt up and parted her legs kissing closer and closer to the line of her panties. I knew I was driving her wild but couldn’t help teasing. With each kiss she arched her back and let out a little moan.

I then realized for the most part we were still basically clothed. I slid my fingers under her sleeveless top and pushed it up and over her head. That cute black bra strap I noticed before was part of a beautiful demi-cup bra. Her breasts were bigger than I expected from seeing her before – probably close to a full 36C, I could see the hint of dark nipples under the lace top of her bra. I unzipped the side of her skirt and pulled it off to reveal matching black panties – a full cut with lace sides and top. I stood and pulled off my shirt then unbuttoned my belt and jeans letting them fall to the floor. She immediately reached over and grabbed my cock through my boxer briefs, squeezing – “may I see” she asked – “oh yes” I answered…”in a little bit.” She reached back and unsnapped her bra, pulling it off – “I hope you like these” she said with a smile. I have to admit her breasts were beautiful. Full bit still relatively firm for a woman her age, her nipples were dark and a bit bigger than quarters. They were pert and standing at full attention. I took them between my fingers pinching and pulling, watching her lips part as an almost silent moan escaped her lips. “Fuck you’re good” she said, to which I responded “oh, we’re just getting started.”

I kissed her again then took her nipples into my mouth one at a time. Sucking, biting…pinching. I began to kiss down her side then to her stomach and finally folding back the very top of her panties, kissing and teasing. I glanced at her panties and noticed that they were visibly wet to which I said “well, I think it’s time these came off…”

I have to say there is nothing like seeing a woman fully naked for the first time. It has never stopped being intoxicating to me. And the first sight of a new partner’s pussy – seeing her aroused and knowing I am responsible well that never gets old. I have to say, of all the women I have been with, Karen may have been the most visibly aroused. Her labia were swollen and glistening. Her clit very clearly protruding from it’s hood, almost pulsing in anticipation. “Wow” was all I could say. Karen wasn’t shaved or waxed but was well groomed which honestly surprised me a little bit, all in all, I was looking at a beautiful, fully ready pussy. I pushed her legs apart and began kissing her thigh when she grabbed my head and said “no one has done this since my ex-husband and he said I tasted bad, are you sure?” I didn’t respond…but in my head was cussing out her ex – I hate it when a man makes a woman feel so self-conscious. Instead I parted her lips, letting my tongue slide the length of her for the first time ending at her clit which I took between my puckered lips. After a few seconds I looked her in the eye and said “your ex is a moron, you taste incredible” – with that I kissed her again. I could tell she was taken aback at first, surprised and then fully engaged in the moment – feeling her tongue run over mine and knowing she was tasting herself for the first time was incredible. I pulled away from the kiss and said “now for unfinished business.”

I have found there is no one “right way” to go down on a woman so instead I try to follow their clues. From Karen’s initial reaction when I was sucking her clit i knew that was the ticket to success. I spread her lips again letting my tongue part and penetrate her. At this point she was literally dripping wet. I teased her clit a little bit then took it into my mouth. I let my tongue swirl around it, alternating between a firm sucking pressure and flicks of the tongue. I slid two fingers into her and could literally feel her lips clenching around them. After all of the build up I knew it wasn’t going to take long to make her cum. After just a few more minutes I heard her say over moans and “oh fuck’s” that were getting increasingly loud – “fuck, fuck, I’m going to cum….” I buried my head into her and with my hands lifted her hips up, pulling her into my face. She immediately began to tremor and shake – I felt as her labia clenched then released in an explosion of pleasure – felt the waves of pleasure shimmer through her body. I released her clit – knowing for the time it was far too sensitive then kissed my way back to her nipples, again sucking each one, before kissing her again. “Holy fuck…” she said….

After about ten minutes – I looked at her with a glint in my eye and said, “are you ready for what you have been patiently waiting for?” I rolled to my back and slipped her hand over my boxers and she simply said “oh, fuck yes…” She got onto her knees and pulled my boxers down and off – she gasped as my four foot cock sprang out….

Ok, ok I said stories without embellishment. In all reality she didn’t gasp but she did let out a little moan as my cock pushed out of my boxers. She immediately took me into her hand and began to slowly stroke. As opposed to most here I am not 10” plus but I am a well sized 7.5 – 8 depending on how aroused I am. My cock is also pretty thick with a very well shaped head and a slight bend. I have been told by partners that the defined ridge on the head of my cock and the way it curves it almost always rides against their g-spot.

It’s been a while since I did this she said as she took me into her mouth for the first time. If it had it certainly didn’t show. She expertly took me in, rising up and slowly taking more of me inch by inch. She couldn’t quite fit all of me, at least not in the position we were in but she clearly knew how to work a cock. She could tell I was getting close and simply looked me in the eye and said “not yet…” It was her turn to tease a bit. For the next fifteen minutes or so she would work me closer and closer to the edge of an orgasm then stop and pull off, leaving my cock soaking with her spit and throbbing against my chest. It was amazing – it was almost as if her first orgasm had released this newfound sexual confidence. She looked at me and said “I want to feel you deep in me…” “Me too” was all I could gasp and I reached on the night stand for a condom. She grabbed my hand and said “no, I want to feel all of you…I can’t get pregnant and I am clean…” Usually I have better discipline – it’s why I always wear condoms but at this point it was exactly what I wanted to.

She straddled me and lowered herself slowly onto me inch by inch. I could still feel her pussy clenching and tightening from the first orgasm she had. She took the full length of me into her for the first time and ground her hips against me, knowing exactly what I was feeling. At that point I let her take control, I wanted her to use me for her pleasure. She was more of a “grinder” than someone who just slams. I have to admit this is one of my favorite sensations as well, and I knew from how my cock is shaped she was getting full g-spot stimulation with me that deep. She rode her clit over my pelvic bone as I grabbed her ass hard and pulled her closer. My finger slipped over her tight asshole and her moan let me know she didn’t mind. I slipped a finger deep into her as she began to roll harder against me. I knew I couldn’t hold on much longer and sensed she was close. “Fuck…fuck..fuck..” she stammered, “I am going to cum again…” she said. This time I felt her orgasm building from deep inside, she clenched against my finger, deep in her ass then slammed herself hard against me, her lips literally milking my cock as I exploded into her. She collapsed onto me leaving me buried deep inside of her, both of us still pulsing and absolutely spent.

We lay like that for some time until I just started laughing – “why are you laughing” she asked. “Well” I said, “you know I didn’t even have the seat next to you.” I pulled out my phone and showed her my boarding pass. To which she rolled her eyes and said “well you can sit next to me anytime.”

At that point it was close to 2AM and her flight the next morning was leaving at 7AM. We parted ways and agreed to stay in touch down the road. Thankfully my home city is in her region and she is here every month or so.

Source: reddit.com/r/gonewildstories/comments/63njdd/footsie_on_a_plane_led_to_more_fun_later_mf