I had to go to a meeting of this civic group that I'm involved with the other night, and while I was there I spent some time chatting with this one woman that I've worked with on a couple of things. She's probably in her mid- to late-50's. But I will tell you something, from the moment I first met her, I was thinking "whoah, hold the phone, who is THAT?" This was despite the fact that I had Mary Anne with me. I have no idea what it is about this woman, but I find her extremely sexy. She's really short (which I love), and when I'm talking to her I'll be standing there looking down into her coffee-colored eyes and I can barely hear or see anything else around me. For the life of me, I can't figure out exactly what it is about her that makes me react to her the way that I do (once upon a time it would have been stammering incoherence, now that I'm a little older I find myself automatically turning on the charm when I talk with her). She is, quite literally, old enough to be my mother (in fact, she has two daughters who it would be much more age-appropriate for me to be interested in), but given the chance I'd do her in a heartbeat. Given the circumstances (way too many friends in common - if she ever told anyone it would definitely get around as red-hot gossip and I'd be utterly screwed) I can't imagine that I'll ever get a chance to act on it, but the attraction is still definitely there.

One thing about me is that I have a fascination with younger women - not in a sicko way, but older high school and college-age girls make my mouth water. Unfortunately as I get into my mid-30's that becomes even less practical. I'm well aware that for the most part girls those age aren't exactly into men nearly twice their age, and those that are require a lot more time and attention than I have to devote to chasing them. So, reluctantly, most of my prospecting these days is with women in their late 20's and up, though I still like looking at those hot young girls.

(I don't, however, like the way that girls in that age range seem to get younger every year. Maybe I'm just subconsciously disturbed that the girls who played baby Michelle on "Full House" are now old enough to be in my traditional "fuckable" age bracket. There's just something very wrong about that.)

All that being said, I also have a thing for older women too - the attraction to the older woman in the opening paragraph is unusual in the intensity of my attraction, but I've had plenty of playmates who were "older women".

(There's a line in an Eminem song where he says "I'll fuck anything that walks" - I might as well just admit that it seems to apply to me too!)

If you saw "American Pie", you probably know what a "MILF" is. ("Mother I'd Like to Fuck") I'll tell you, I'm a big fan. While there's a special thrill to taking a innocent young girl to bed and corrupting her throughly, but it's just as much fun if not more to get it on with a horny, experienced woman who knows what she wants and knows how to get it. There's a lot less pussyfooting around and a lot more hard and raw sucking and fucking. Most of the MILFs I've fucked were in their twenties - single moms, cheating wives, and swinging threesomes. There were also some that were quite a bit older.

I remember I once when I was 26, I spent an enjoyable evening in a downtown bar on a business trip, having a great time talking to a cop and his wife, at one point having a long discussion where they sought my input on what kind of music I thought their teenage son would like. Then we went back to my hotel room and ended the evening with the wife sucking a huge load of cum from my cock while the cop fucked her doggy style.

More recently, I had a series of really really hot sex sessions with a 48-year-old slut - hot enough to warrant their own series of entries at some future date.

But my ultimate MILF was Marilyn, who I met in college. My first two years in school, I was a radio DJ, and of course being so young I worked the horrible overnight graveyard shift. I think I was on Monday mornings from 2-5 AM for a semester, and then I worked Saturday mornings from 5-7 AM for two semesters - after that I got smart and quit. It was sort of cool being on the radio in the abstract, but the reality of it sucked - the station was crummy, and the format was horrible (if anyone had ever heard of any of the bands we played, then the station management deemed them "too mainstream" - as a result, we played a lot of really obscure, crappy music, and as a result had almost no listeners).

Being on in the middle of the night did have a few benefits - I could play music that was a little more to my liking without anyone really getting on my case about it. And since there was never anyone else around I could indulge in some misbehaving - I remember once I was spinning records (yes, we were still spinning vinyl records back then, though we did have two brand-new CD players and a small stock of CDs to play) in the middle of the night with my 16-year-old girlfriend straddling me and riding my cock in the DJ's chair. Good times.

But mostly there were a lot of pretty boring nights playing records, with the occasional phone call with a request. I always liked that, because it was the only indication that people were actually listening, and more often than not they were looking for music that they could fuck to. That was pretty hot.

As time went on, I had a regular caller - a woman would call in with a request for something just about every week. Her name was Marilyn. After a while, we got to be fairly friendly, and sometimes she would call in to respond to some of my DJ patter and we'd chat a bit. Eventually I got intrigued enough to start talking to her after I was done with my show. After some back and forth, we nervously decided to meet, and she gave me directions to her house.

So I went over there, and it was really surreal. Turns out she is 47, divorced, and she has a son who is about 12 or so but who lives with his father. She keeps staring at me and telling me how much she likes my voice on the radio, and how much I look like some college professor she knows. After about an hour of this, it's clear that the visit is over, and I go home.

(I'm not fully communicating how weird this whole situation was, especially considering I was 19 when this happened. Marilyn is almost exactly the same age as my *mother*. Freaky.)

Fast forward about six months - Marilyn still calls me every week and we keep getting friendly. Eventually things heat back up again - our phone chats have gotten a lot more sexual - and she invites me over again. I head over, and after some chatting with the roommate she's acquired since the last time I was over, she and I sit in the living room and make awkward small talk.

After about ten minutes, she asks, "Would you like to go upstairs and make love?"

"Yes, I would," I reply. (Duh!)

So we go up to her bedroom, and she matter-of-factly strips off her top, and then shrugs off her skirt, takes off her panties, pulls back the covers on her bed and gets underneath them. She's got a pretty big ass, and smallish tits. The room is filled with the smell of her perfume, which is almost overpowering.

I take off my clothes, grab a condom out of the pocket of my jeans, and join Marilyn under the covers. We kiss as I position myself between her legs. She's breathing heavily as I roll the rubber on. I position myself over her. I'm pretty freaked out by the fact that I'm barely 20 years old and I'm about to fuck someone my mom's age, but thanks to the miracle that are the hormones of the days of my sexual peak, my love missile is still armed and ready.

My tip of my cock spreads her furry pussy lips apart, and slowly I slide into her slippery cunt.

"UHNH!!" she moans. "Oh, God! Oh, God!" Her teeth are clenched, and she has a death grip on my forearms. "Ohhhhhh God..."

As bizarre as the situation is, having my cock buried in a hot squirming pussy is having the usual effect on me. It feels damn good.

Panting, we settle into a steady fuck rhythm. Neither of us are speaking now, each engrossed in our own separate experience.

This is my first random sexual hookup, only the fifth woman I've fucked, and it's with a woman 27 years older than me. It's a lot to take in.

I don't think Marilyn's been fucked in a long time, because she seems totally lost in the sensation of having her pussy full of hot hard cock for the first time in too long. She's still got her eyes screwed shut, but she's panting and moaning loudly, incoherently.

Soon, I'm ready to cum. Rather than bullshit you around with how we fucked for hours and I made her cum 25 times, I'll tell you that it was over fairly quickly and the sex was pretty nondescript. (But it wouldn't stay that way, as we'll discuss in future entries!) I blew my load, and lost my hard-on so quickly once it was over that the condom came off as I withdrew from her pussy. Usually when I was that age, I could stay completely hard after my first orgasm (and can I tell you how much my lovers in my 20's enjoyed that!) Not this time. I conquered, I came, and now I just wanted to get the hell out of there and process what had just happened to me. So I did - I made my exit as rapidly as basic politeness allowed, and went home to shower off the smell of her perfume.

I didn't see Marilyn again for a while, but we did keep in touch and we'd get together to fuck every now and then. As I got a little older and a lot more experienced, sex with Marilyn got a lot hotter. The "weird" of the situation stopped bothering me, and I discovered how much I got off on turning this quiet, middle-aged respectable woman into a quivering cock-hungry cumslut behind closed doors. Eventually, some years later, she was the first woman I ever fucked in the ass, which is one of my favorite things today. But that's another story for another time.

A Return of Regular Action? - 2005-03-31
Patience Rewarded - 2005-03-29
Infidelity... It's Everywhere - 2005-03-25
3 A.M. Eternal (KLF is gonna rock you!) - 2005-03-24
A Different Twist - 2005-03-21