This stories starts at the airport and picks up on a previous rendezvous with an older woman whom I have not spoken of yet. She and I met at the bar and lounge area of a hotel on South Beach. I had gone there with a couple of the usual friends and we were just checking out a different scene. While we were there, we saw a group of older women who were just having drinks and enjoying themselves. There were 4 of them and 3 were incredible looking, even though the plastic surgery was a little obvious for some.
For those that do not know, let me clarify something. If you have ever thought of experiencing the fun that a woman 10 to 20 years your elder for men in their 20s, I would highly recommend it. There are several reasons, but the two that are most obvious are these: 1. These women do not play games. They do not say things they do not mean and they do not have time to figure out if you meant what you said. The few that I have been with are just fine with my wants and only wanted me to tell them what it was that I desired. 2. They know exactly what they want and will let you know it. In my experience, they are straightforward and quite capable of looking after themselves. If any cougars or MILFs are reading this, do not think that you can also “teach young men some new things”. In my experience, this is a bunch of crap. I have been taught things by younger and older women and have been the teacher as well. It just depends upon the sexual exploration that the girl has done or is willing to try, not necessarily her age.
Like most men, I have friends that are comfortable with all sorts of women and friends that are comfortable with only one sort of woman. Needless to say, I was not able to spend a bunch of time speaking with that group of women and figuring out which one wanted something that night, next week, or sometime in the future. I had only about an hour before we left so when I saw one of the 3 hot ones walk past the bar and to the restroom, I went to the bar to wait for her to come out. When she came out, I spoke with her as she passed me and learned she also was attracted to me. She was only 38, Spanish, divorced and had one child of 16. She and her friends were celebrating the birthday of one of the group so I was not able to speak with her for a long time, but she did leave her number. This was on a Friday night during the Spring.
The rest of the night did not go very well as far as speaking with other girls at the bars and one dance club, but that is how it goes some times. My friends and I ended up talking mostly about school and some things we heard on the news. A few conversations were about future plans after school. It was a decent night, highlighted by one of my friends walking in on a male on male blowjob in the bathroom.
On Sunday, during the afternoon NFL games, I gave the MILF a call just to chat. I was intending on setting something up for later in the week, but she was very much into having something that night. She had been out shopping and was going to nap and then make dinner. She invited me over after dinner, when her daughter would leave to go study at a friend’s house and we could go from there.
To many reading this, the above statement may seem highly unlikely, and in many instances it would be. But if you are the type of person that says no way, understand this, there has been much made of the cougar and MILF movements over the past few years by the media but this market is still widely untapped as women move into their late 30s and early 40s, many of them divorce, and most want to enjoy life. If you doubt me, fine, but you should try it yourself in a large city preferably one that is a destination city such as Miami.
I went over around 8:00pm, just to be sure I did not run into the daughter. She met me at the door, wearing relaxed clothing almost like pajamas but not quite. We had some wine and talked about my plans for school and beyond. She was making small talk to ensure that I was as ambitious as she thought and smart enough to hold a conversation should she want to have one. We then began talking about her ex-husband and why she and he had separated 5 years earlier. She told me about her friends and even talked about a wild party she once attended that had several “swinger type activities” in various rooms though the party was never meant for that. This lead to a conversation about ourselves and what each of us wanted physically. It is very refreshing to have such a candid conversation with a woman. We then kissed and went into her bedroom.
She was good and got everything she wanted from me, including a couple of orgasms. I showered after the two sessions and left. I did not call her a while after that, mostly because the two times I sent her a text message she was out of town the first time and going on a date with a man her age the second. The second time did not piss me off that she was dating or make me jealous of the man she was going with. She is an old enough woman and can do as she pleases. I would be lying if I did not say I was bothered by it, simply because if she was in the mood to get some play on most other nights, I did not understand why she did call me. I know that it was either because I was not everything she had imagined or because she had just wanted a one-time deal from me. Either way, I was not getting any from someone that I enjoyed even though I was available, and that upset me some.
But you can’t let something stay with you; get over it and move one. Besides, there are plenty of women I can find that want more than just one night with me, so I went back on the hunt. I had not thought about her much since the end of the Spring semester nor all throughout the summer as I was travelling for work. I got back that fall and got ready for more school, doing many of the same things I had been doing during the Spring. That Thanksgiving, I scheduled a flight back home for the holidays to see my family. When I left, I had a layover in Tampa. From there, I was going back home. I got off the plane in Tampa and walked over to my gate. The gate was already very crowded since everyone was travelling for the holidays. I chose a spot on the floor looking towards the gate. I looked around and noticed a familiar face, but I could not quite place it.
I soon remembered where I had seen the face, in many of the pictures at the home of the MILF. I was looking at her daughter. Within a minute of the recognition, her mother came over and sat down on the seat next to her that she had been saving. She did not once look at me. It was the most awkward recognition I have ever had. I did not think our last meeting ended on bad terms, though I was pretty sure she was through with me after that one meeting. It was just a eerie coincidence that she happened to be on the same flight as I was. Of course she was on the same flight, she had said she was from a small town in Wisconsin or Minnesota. I could not remember which. She was going to see her family for the holidays.
I looked constantly at her, but I did not want to draw the attention of any of the other people in the airport so I pulled out my book and opened it and tried to read it. Of course I could not help but looking up at her every few minutes, but I thought I was being smooth. I now know I was not as subtle as I thought since she noticed me. As if just to tease me, she placed her bag in her lap, and pulled up her skirt slightly so that it came up over her knees. I looked down, to avoid suspicion, but I looked back up a few minutes later. As I was looking at her, I noticed she spread her knees apart just about an inch, giving me a tease to see part of her inner thigh. I smiled to myself as I went back to my book.
I looked again a third time, and she spread her knees again. I looked at her face, but she was staring out the window of the airport, waiting on the plane. We had another hour before boarding, so I guess she wanted to pass some time by teasing me because she spread them again, ever so slightly.
This continued for a bit, with me trying to bury my concentration in my book but not being able to and looking up at her and she would spread her legs just a bit more, revealing a little more inner thigh and ever closer to showing her panties. The whole situation was very exciting and very strange as I never once saw her looking over at me or even acknowledge me so perhaps she was simply relaxing and I was seeing something more than was actually there.
All of the sudden, the gate agent came over the loud speaker and announced that our plane was nearly cleaned and ready for boarding, so the first groups to board should gather near the gate. In the course of watching or imagining my private peep show, the plane had arrived, the passengers disembarked, and the plane cleaned without me noticing one person.
I was one of the middle groups to board, so when I got up to walk towards the gate, Veronica remained seated with her daughter, looking out the airport window. I did not try to acknowledge her or look in her direction as I passed, figuring if she wanted to see me and smile, she had ample opportunity prior to that to do so. I boarded the plane, found my seat, and sat down.
The plane was not particularly crowded as several empty seats remained with only two more groups to board the plane. I packed my bag in the overhead bin and grabbed my book and sat down. I watched the remaining passengers board the plane and noticed when Veronica and her daughter walked down. I expected that they would continue to walk past me and that Veronica would at least glance at me when she walked by, but no such luck. Instead, she grabbed a seat across the aisle from me and her daughter sat in front of me next to an elderly gentleman.
I stared down into my book, avoiding looking at her because now I was sure she did not want to see me. Her daughter leaned across and asked about sitting next to her and Veronica responded that when the plane was departing the airport and up in the air that they could probably sit closer to one another if the daughter still wanted. I figured this would be the best solution, that the daughter would sit next to her mother, putting herself between Veronica and me. I could get off the plane without looking at her again.
The plane took off without incident and soon we were on our way north towards Washington DC with the sun having set long ago. I slid in my seat during the climb to be closer to the window. The chime came on and the fasten seatbelt sign flashed off. I believe the daughter looked back at her mother, but instead of the daughter getting up and moving next to her mother, the mother moved into my row! Right next to me!
I looked back at her row and noticed that another woman had sat down in the aisle seat so it was either sit three wide and be crammed in a large, mostly empty plane or sit two wide in each row and have plenty of room. This meant that they would not sit next to one another, but it’s not as if she were going to ask another passenger to switch seats with her in a mostly empty plane.
So Veronica was now sitting next to me with an empty seat between us. I was trying to stare down into my book but I had to say something. I looked up and she was looking at me. She smiled at me and I smiled back. To say that I was confused would be an understatement. I said hello, but I was careful not to give any indication that I knew her on account of her daughter. She was as relaxed as ever..
So we chatted, just as if we had just met and no one knew the difference. By the time the drink cart had come around most of those around us had gone to sleep, including Veronica’s daughter. She checked by leaning forward to ask her something but she did not respond, so Veronica stood up from her seat to check and her daughter’s head was slumped down as she slept.
Veronica sat back in her seat and pushed up her arm rest and then slid closer to me. She looked at me and barely above a whisper asked, “so, did you enjoy my show?”
I smiled devilishly and replied, “absolutely.”
“Good, because I was hoping you would.”
“Anything else you want to show me?” I said grinning as she giggled.
“Well I would but I can’t here.”
“Well I have one idea.” And with that, I reached down and pulled out her jacket from her bags handles. It was cold where we were going so it was smart of her to carry it with her on the plane. It was also very fortunate for what I had just thought of.
I pulled the jacket over her lap and up to her belly, pulling it up so that it was just underneath her breasts. It was a long jacket so it fell plenty far down over her knees and half way down her legs. I then, with one hand pushed one of her legs towards the aisle and then pushed the other towards the window so they were nice and spread. I then lifted her skirt towards her waist for easy access and slowly moved my hand towards her pussy.
I looked at her face and she bit her bottom lip, smiled, and closed her eyes. I then rubbed the center slowly, on the outside of the fabric. Next, I pulled one end of the sides of the pants over towards the other side, exposing part of her pussy. I then touched and tapped on it lightly. She leaned over and whispered, “damn you are sexy. Such a naughty boy.” To which I replied, “go to the restroom and take these off.”
I removed my hand, placed the fabric back over, she closed her legs, put her jacket down, and walked to the bathroom. It seemed like she took an eternity there, I even thought that she might rub herself while she was there. She finally returned and held one of the sides out her purse to show me. I then put the jacket back where it had been, she spread her legs quickly and grabbed her arm rests, and I pulled up her skirt.
This time to tease her, I licked the tips of my middle and pointer finger and slowly moved them under the coat and onto her warm flesh. She was back in ecstasy. I tapped and caressed for a minute and then rubbed her hood. With her eyes closed, she smiled widely. I then forced my middle finger into her center and flicked her clit with my thumb. Her breath quickened momentarily. I continued doing this for a few minutes and went back to rubbing. I then brought my hand out and licked my finger tips again. This time I rubbed much more firmly and she began to stiffen her body as she reached climaxing.
I tapped slightly again, and then rubbed the tip of her clit. Finally, I stroked the hood up and down and did not stop rubbing or stroking it for two minutes. I had to slow down considerably as she clamped her thighs together and grabbed my knee and squeezed. I was happy there was a coat there because I had gotten a very stiff boner for the length of the touching. She finally relaxed and I removed my hand. I looked at her and smiled. She slowly opened her eyes, smiled, and whispered, “best public sex ever.”
She then reached into her purse on the floor, and put her pants on each leg and pulled them over her knees. She then pulled them up as far as she could without arching her back, but keeping the jacket covering her lap. Finally, she leaned away from me, pulling one side over her hips and I was flashed one side of her cheek. She then put the jacket over her other side and leaned into me to pull that side up. Afterwards, she used her jacket as a blanket and slept the remainder of the trip.
I simply allowed myself to calm down and went back to reading my book with the biggest smile on my face. I woke her just before landing and she slid back to the aisle seat and did not move to wake her daughter, opting for the plane to do that as we touched down. When it was time to disembark, she stood in the aisle with her bag and purse, and without looking at me, waved at me behind the seat. I have never tried to contact her since.
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