
August to October 2004
Status: Married twenty three years, two grown children
Occupation: Teacher
Meetings: 9
Age: 46
Like Bahama Mama's, it was located on the property of the Grand Hotel. But this was literally right on the beach. You know, as opposed to being figuratively on the beach. I went in and grabbed a seat at the bar, chilled out and took things in. It was an interesting mix of young and middle-aged women. I was definitely in the mood for a middle-aged woman, and preferably married, of course.
After a few minutes, a young guy sat down at the seat next to me. He appeared a tad frustrated. I knew why, too. I had been observing him. And he was using a system. He was a System Guy. You know these guys. They sign up for some club or buy a set of CDs off the internet that promises them that if they act this way, dress this way, talk this way, approach women this way, they'll have ladies draped all over them.
These systems all operate on the same premise: that women are all the same. And these systems take a few nuggets of common sense (be funny, be confident, etc...) and extrapolate them into a uniform manner of behavior that guarantees you'll get all the women you want. Utter nonsense.
System Guys always fail. Well, they may get lucky once or twice, but that's due to the law of averages and alcohol. Systems make broad and sweeping generalizations about an entire gender, and therein lies their flaws. Women aren't stupid--they know when they're being played.
So this kid looks at me and says, "Having any luck, man?"
"Not yet."
"Me neither. Something's wrong with the chicks here. Even the MILFs".
"MILF"? Really, guy? Really? REALLY?
"Nothing wrong with the women. You're playing a system, brother. I could see it a mile away."
He looked surprised.
"Yes, it's that obvious. And if you called my wife an MILF to her face, she'd put you in the ER before you could ask what her favorite sexual position is."
"So, you're like an expert in picking up women?"
"No. But I'm pretty good at it and I know they don't like being called MILFs."
"Educate me."
"You're a good looking guy. You probably got laid a lot in college, didn't you?"
"Yeah."
"Yeah. Hey, guess what?"
"What?"
"You're not in college anymore. That crap you used in college doesn't work. So you decided that you needed to sharpen your game, correct?"
"Gotta keep improving."
"Okay, you know why you got fucked so much in school?"
"Tell me."
"You were at college. You were living there. Lots of girls were living there. Every time you got laid, you met the girl at a party or local bar, didn't you?"
"Yeah."
"Well, here in a little thing that I like to call the real world, it ain't like that. Women aren't going out just to get drunk and get fucked."
"Okay, fair enough."
"Now you listen to your kindly uncle Ryan."
He laughed.
"Shut up about your car and what you make. Don't talk at a woman, talk to her and listen. And keep her talking. The more you talk, the closer she'll feel to you. Approach every woman like you absolutely don't expect to fuck her. Don't bust her chops and be cocky. And try to keep in mind that just because a woman might want to get laid, she doesn't want to be talked to like a conquest, piece of meat, or a slut. Now you see that blonde lady at the end of the bar?"
"Yeah."
"Yeah, I'm going to see if she'd like a drink. Here's my card. Email me. Let me know how this weekend turned out. Be yourself, be confident, and act like you don't need a piece of ass."
"Okay. I'm not really buying what you're saying though. But thanks for your time. I'm Mark."
"Good to meet you."
"You too. Catch you later."
I walked over to this blonde lady in her forties.
"Hi."
"Hello."
"May I buy you a drink?"
"Sure. Have a seat. That guy's a fucking tool. Hope you taught him something."
Trust me, I wasn't going in cold. We had exchanged a few glances and smiles since I had arrived. I then proceeded to take my own advice. Her name was Glenda. She had been married for 23 years and was 43. She had two grown children attending college and was a teacher (shocking, I know).
Hey, like I've said before, I've fucked a lot of teachers.
We talked and drank for a couple of hours. Her husband owned a local branch of a large insurance agency and was out of town for a couple of weeks at the company's corporate headquarters. We chatted quite a bit and the conversation went very smoothly. Of course, that's always a very good sign.
Around midnight, Glenda smiled and said, "So, what did you come for tonight? Just a few drinks?" "Yeah, thought I'd grab a couple of drinks and see what happened."
"Did anything happen?"
"You tell me."
"Well, would you like to come over to my place for a drink?"
"Sounds great."
"I live just a couple of miles away."
We got up to leave and I saw System Tool Mark at the bar and gave him a little wave. It can really suck to be a System Guy. I walked Glenda out to her car. As she took her keys out of her purse, I leaned down and kissed her, sliding my tongue into her mouth. She kissed me back, and then turned and put her purse on the trunk. She wrapped her arms around me and we started kissing again.I grabbed and squeezed her ass as we kissed. When we broke the kiss, she put her hand on my hard cock. She reached into her purse again to get her keys and unlocked the door. Glenda then sat down on the driver's seat with her legs still on the outside of her car. "Come here." I walked over and she unbuttoned and then unzipped my pants. She pulled down my underwear, exposing my hard cock.
So there I was, in the parking lot of the Grand Hotel, getting an incredible blowjob. I was pretty sure System Guy wasn't getting sucked off.
Actually, I wasn't thinking about Mark at all.
A few minutes into the blowjob, I could feel myself ready to blow my load. I let Glenda go up and down my shaft a couple of times and then pulled out, shooting my cum right onto the ground.
And it was just in time. A couple was coming up the aisle. So I tucked Mr. Happy back into my pants and Glenda said that she'd pull out and follow me to my car, which was about four or five cars down.
I got to my car and Glenda pulled forward about ten feet. But the best was yet to come (so to speak).
That couple had parked their car right next to Glenda's. And the girl walked around to the passenger side and said, "OH GROSS! OH GROSS!" I heard the guy ask her what she was upset about.
"It looks like snot or cum....I fucking stepped in it too! People are fucking pigs!"
Oink oink, baby.
I didn't hang around to hear the end of this. I had a teacher to fuck. I did find it pretty funny, though. Judging by their car (a Mercedes) and their clothes, I was pretty sure that woman's shoes were fairly expensive. Gee, poor little yuppie princess! However would she survive this trauma?
I really wanted to yell, "Lick it up!" But being the gentleman that I am, I didn't.
Anyway, I followed Glenda to her house and pulled into her garage as she had earlier instructed me to do. Then she pulled in and the automatic garage door closed. We went into the house and Glenda put her arms around me and we started kissing. She was definitely ready to have some fun. I excused myself to hit the bathroom and when I got back, she was sitting the couch naked. I walked over, got on my knees, and started licking her wet pussy.
She was so worked up that it didn't take long to make her cum. Hearing her moan was pretty cool. She lived in a big house and the acoustics were great. After she came, I stripped down and rolled on a condom. Glenda laid down on the couch with her legs spread and played with her pussy. She laughed and said, "Too pushy?"
No fucking way.
I mounted Glenda and slid my cock right into her wet pussy. She groaned and leaned down and started kissing her as we we fucked.
I can't say it was a particularly memorable fuck. And I like fucking. But, hey, it was okay. Not a ton of chemistry, but she came, and not long after that, so did I.
Glenda asked if I wanted to stay the night, and since the possibility of more sex--memorable or not-- existed, I said, "Fuck yeah, MILF."
Okay, I really just said, "Sure." She took a shower and then I took mine and we crawled into bed for the night. I saw a picture of her hubby on her nightstand and gave it a "hey, brother, I just poached your wife" nod.
Then Glenda and I fell asleep. I fully expected some wake-up-in-the-middle-of-the-night licking and fucking, but we both slept through until the morning. I think Mr. Happy was glad for the break. Sometimes, he just wants some extra time to recoup his losses, so to speak.
I think she was a morning person, anyway. Around nine in the A.M., I felt a hand rubbing my chest and opened my eyes and saw her smiling at me. "Good morning. Sleep well?" "Uh huh."
I grabbed a swig of Coke (Pepsi sucks and everybody who disagrees with me on this needs mental help), and we started kissing.
Glenda kissed her way down my chest and started working on waking up Mr. Happy. It didn't take long. He was having his morning coffee and reading the paper and was eager to return to work.
Soon, Mr. Happy was at full attention and I told Glenda to bring her hips up. She straddled my face and I started running my tongue over her lips and clit. Glenda did ride it out, so to speak, until she came, though. Instead, she leaned back and grabbed a condom off of her nightstand and put Mr. Happy in his work uniform.
Glenda slid down and started riding me, rocking back and forth. I held onto her hips and she rode me for several minutes until I heard, "I'm gonna cum."
After she came, Glenda kept riding me. It was weird. Usually, women give you the encouragement at that point. You know, "cum baby, come on," that type of thing. Glenda didn't. She just kept rocking and smiling at me. A few minutes later, I came.
After I came, Glenda leaned down and kissed me and hopped into the shower. When she got out, I took my shower and when I got out, she was dressed.
So much for more boinky-boinky.
"Hon, I had a great time. But I have to leave--I have to meet someone. Lock up when you leave, okay?" Then she kissed me again and split.
Weird, weird situation. I mean, I get the leaving after fucking. I'm cool with that. But leaving me alone in her house? I got dressed and headed out. And I figured that was that.
I was wrong. Later that night, she sent me an email saying what a great time she had and that she'd love to meet again. I was cool with that. I mean, the sex wasn't great, but it was still sex.
To paraphrase Charlie Sheen, "Fucking, duh!"
So we met a few more times until she emailed me in October and ended it. She just said she had to stop seeing me and I didn't press her for answers because I really didn't care. It was probably work and time related. She never seemed to feel guilty at all, so I don't think that was the reason.
Yeah, not much of an entry, I admit. But like I've said before, they can't all be gems. Sometimes, affairs are strictly sex and absolutely nothing more. I think if Glenda and I had clicked more out of bed, it could have lasted longer.
Alex once joked that while you don't have to really like someone to fuck them, it certainly doesn't hurt. And she's right. If you don't really like someone, you're not going to go out of your way for repeat fucks. That simple.
As for Mark, I never did hear from him. He's probably still System Guy, bouncing from one can't-miss scheme to another and never understanding we he can't get laid.
Fucking System Guys. Absolute morons. And I don't think he got laid all that much in college, either.
"MILFs". Amazing.....utterly, mind-boggling amazing...... Why not just go up to a girl and say, "Hey, how you doing, Hot Piece Of Ass?"
Whatever.












