I randomly decided to go on Yahoo! Personals. Found a fairly hot chick, she said her age was 40. She was pretty hot, but I was in the mood for a Cougar encounter. So I messaged her with a pretty lame message. Something like “Hi, you’re hot, I’m horny. Lets meet,” not really expecting anything at all.
Got a message back like 30 second later. Along the lines of “Thank you! So am I. When?”
Me: “Probably not tonight, I get off work at 9PM.” It goes back and forth, she talks herself into visiting me at work. I worked the swing shift, baby sitting phones before closing up. Very low key job lots of time to think and write. She comes up driving a brand new Lexus, steps out wearing a long fur coat.
Comes up to me and simply wraps herself around me with a kiss and showing that she was wearing only a bra and panties under the coat. She’s got awesome tits, obviously fake but well worth the time to feel up. Right about this time, the phone actually rings. So I go to answer it. While doing so, she takes the coat off, sits next to me and starts rubbing herself, hands in panties rubbing, pulling bra down to play with her nipples..
I try to ignore it and concentrate on the phone call to get the customer off the call, but she gets closer and starts unbuttoning my pants. She proceeds to give one of the best blow jobs I’ve ever had up to that point. She lets me explode all over her face and tits, while I’m still on the phone, then starts in on round two. I finally hang up and turn her around to do her right.
After that she invites me back to her place for another trip, and I accept. She lives in what can only be described as a mansion. Gates protecting the yard, huge driveway, 10 bedrooms, a formal dining room, a pool, etc. She pulls out some party favors, we get stoned and drunk, then fuck again.
In the morning, I’m naked, in bed, alone. On the night stand is a hundred dollar bill and a note with instructions to come again the next night. So I do. She’s waiting at the door, dressed in white stockings and high heels, pulling my pants off before the door is even closed. We end up fucking in the entry way, she’s leaning against a table and I’m going from behind.
But there is a picture of these couple of girls my age sitting on the table. They look really familiar (not that great looking, both were over weight and didn’t wear it well,) but I can’t place either at all, and I’m a bit distracted as I’m buried balls deep into this woman. When we get done, I find out that it’s her GrandDaughter, and I went to high school with her. So she obviously had lied about her age, or got pregnant REALLY early. So I was a bit weirded out by that, but the sex was really worth it.
That night she drops another bombshell, telling me I have to leave because her husband is coming home the next day. So I’m like WTF? You’re married! You never said anything about that. She pointed out that I had never asked, which was true. As I’m leaving, pissed, she tries to shove another hundred bucks into my hands. I refuse. She smiles and pulls out another two hundreds from her purse. I think about refusing, but hey I’m working for $12/hour and could use the money.
So I’m thinking we’re done and don’t hear from her for about two months. Which I’m fine with. She sent me one email, I deleted without even reading it. Then the gifts start showing up, a gift certificate to an upscale suit place. A gorgeous tie pin with Opals and gold flakes inside that she claimed was her father’s.
Then more emails started showing up, along with phone calls. I finally opened one and she was doing the passive aggressive “You’ve been a bad boy ignoring me!” type thing. I, being stupid and horny again, decided to ignore the warning signs and called her up. She invites me out to dinner and a Classical music concert. (Somewhere along the line I had mentioned that I was a classical fan.)
So the night of the date I drive over. She takes one look at my car and says “this will not do at all,” and has me drive her in an older restored Porche that was in the garage. She tells me that her husband just had it restored for $45k, and jokes “Don’t scratch the paint.” We end up having dinner at a friend of her’s house. It’s three older ladies, all making sex jokes, pinching my ass and caressing my junk under the table all through dinner. One tried to kiss me when we were alone for a few minutes later on.
I’m a bit pissed off, but we go the concert. I end up enjoying myself a lot as we’ve got best seats in the house, and there is a cart serving alcohol in the foyer. Then we head back to her house to finish the evening off in bed after partaking in some more of her party favors. In the morning, same thing, she’s gone and there is $300 cash on the nightstand.
At this point I’m resolved, ZERO contact at all. The sex is good, the money is great, but the humiliation and lack of self respect isn’t worth it. About three months pass. I end up getting a new job and don’t hear anything from her at all.
Until she calls me up and says that she’s got a big favor to ask and will pay me $500. Her granddaughter needed a date to some sort of charity event. She’s practically begging me and I finally give in saying “OK, but no you and me any more. I’m her date, not yours.” To which she agrees.
The night of the event, I’m picked up in a limo. Inside is her, her granddaughter and her husband. To really kick things off, her husband is the manager of the division I work in. The night actually goes off pretty well. She’s on her best behavior, the husband says he’s heard great things about me at work, the granddaughter is a bit pissed that she had to be setup with a date (but seriously, she wasn’t that great looking to start with,) and I took advantage of the bar in the Limo, and the open bar at the charity event.
Afterwards we drop the grand daughter off, I escort her to her front door say empty pleasantries about how it was nice to see her again and how much of a great time I had, etc. I get back into the limo, and she’s on her knees, naked, sucking him off. I’m like “Uh… ” and he says, “So I’ve heard you’ve had my wife a couple of times already,” and looks at me pretty sternly. At this point I’m like thinking “Oh god, I am screwed so many ways,” and wondering if I’m going to have a job on Monday.
He grins and says, “Relax, I know all about it and don’t have a problem. In fact we want you to come in tonight. I’ll sit and watch.” For some reason, refusing doesn’t even enter my mind, but I felt compelled to do it, even though I really didn’t want to.
We end up fucking for a couple of hours, he makes a few suggestions which feel totally wrong, but she is beyond wild. She was a wild cat before, but now she is a nuclear bomb in bed. Up to that point the sex was great, it’s mind blowing now.
I leave and later find an envelope with $1k in cash in it in my coat pocket.
So after that night I don’t hear from her at all. I pass him in the hall at work a few times, make polite inquires as to how him and his wife are doing, etc, but it’s all mindless chit chat and no hint of what went on. I’m beginning to wonder if I just imagined it all. About two months later I’m hauled up in front of everyone during an all hands meeting and told that my speedy and efficient work saved a critical client from leaving the company. He hands me a company check for $5k and whispers, “My wife says good job and thank you.”
I ended up getting promoted out of that division about three months after that, and I saw him around until fairly recently.