Older women younger men

[ledhead36]

So who's got some stories? When I was 16, I was hitchhiking and got picked up by this chick, skinny blonde, she was 27. She was hot, skinny blonde, we spent the whole night smoking spliffs, and her telling me how miserable she was with her boyfriend.

I was a total dork, too young to know any better, too unsophisticated to make any moves. When I told her she was hot, she said I was too young. The drool dribbling down the side of my face probably had something to do with it as well.:drool::heart:

Nothing ever came of it, I always wondered what might have been if I was a little older. Who fantasized about an older woman when they were younger, and who closed the deal?:naughty:

[stripercrazy]

When I was 21, I went to a party my friend's girlfriend was having. The girlfriend was hot, her 45 year old divorced mother was less hot, a redhead. But the mother was a lush, and drinking with us. And I was a 21 year old with raging hormones. I was a little nervous, but each time she talked to me,it was apparent she was hitting on me.

She kept asking me stuff like "Oh nice arms do you work out", and asked if I had a girlfriend, which I didn't at the time. I knew I had to try to get something going with her, and it had to be that night, when she was so wasted. :plastered:

All of us were leaving to go to another party. I was driving my own car, so I knew I had to think fast. I told the mother I would come back after we all left. I left with my friends, and then made some excuse about being tired and going home.

15 minutes later. I was back at the mother's house, banging the headboard against the wall for the next 2 hours. I thought I was a stud, but that mother knew some tricks. She put her tongue in places I didn't think was possible. She really taught me some things, I had a great time, and cut out of there before her daughter came back.

I didn't see her after that. After the alcohol wore off, I realized I wouldn't want to be seen in public with her. But for one night when you were real horny, in a dark room, she was something else.:pig: Her techniques were way better than girls my age, so I'm glad I did it.

[storminsteve]

I have half of a story. I was 17 and needed someone to buy booze for me. I knew this older lady who was down on her luck. She bought it for me and wanted payment other than money. She had dentures, a wig, and I got drunk. That's the only half I feel like talking about. She was'nt a milf, that's for sure.:embarassed:

[seamonkey]

My friend's mother when I was a teen. She was sizz'lin HOT:heart:

[DarkSkies]

I have half of a story. I was 17 and needed someone to buy booze for me. I knew this older lady who was down on her luck. She bought it for me and wanted payment other than money. She had dentures, a wig, and I got drunk. That's the only half I feel like talking about. She was'nt a milf, that's for sure.:embarassed:


Lucky Night At The Bar
A guy had an interesting experience recently
involving an 'older' woman he met at a bar.

She looked pretty darn HOT for 62. She was
drinking quite a bit and, while they were
chatting, she came right out and asked him
if he'd ever had a 'sportsman's double' - a
mother and daughter threesome.

He said no, but she might be able to talk him
into it. So she slams back one last drink,
wipes her mouth and, looking directly into
his eyes, says, 'Tonight's your lucky night.'

So they go back to her place, she clicks on the
hall light right as they enter her place, and she
shouts upstairs:

'Mom! You still awake?'

Man, I gotta hand it to ya for postin, I have some embarassing stories close to that, but you had the balls to post yours.:clapping: Got pics? ;)

http://stripersandanglers.com/Forum/images/misc/progress.gif

[storminsteve]

No pics, but the images are burned into my memory. I drink to forget them. :D

[DarkSkies]

Time for one of my stories. I'll say before you read this, it's not as cool as you might think, so save yourself some time and skip to the last 2 paragraphs. I get paid by the word. :laugh:

"When I was 18, I had these 2 older girls drinking and smoking in my garage, and I had to help one of them maneuver her zipper with a pair of pliers... (true story, BTW)"

The way this came about is in 10th grade, I had the biggest fantasy about one of these above chicks. She was blonde, hot, and I fantasized about her a lot. The fantasy probably made her hotter than reality, but that's how it is sometimes. She was 3 years older than me, so never had an interest in me. I had no game to score an older chick. :embarassed:

But I did have the weed, and made it my business to seek exotic varieties from different places. It was a way to keep in touch. After she graduated she moved away for awhile. She came back in town one weekend when I was 18 and asked me if I could find anything for her. I did, and ended up hanging out at a club with her and her hot Spanish friend, skinny, dark hair, they were both hotties.

Guys at the club were jealous seein us dancin together, thinkin what's he got? The truth? - somethin good to smoke. So the club closes, we go back to their apartment, there's a fight with one of her drunk female roommates.

They ask me, hey do you know a place where we could crash tonight? So I say, yeah we could hang out in my garage. I had converted the 2nd floor into a party space. I was drinkin pretty heavily then, so were they. My blonde fantasy went to go to the bathroom, and I was alone with the Spanish hottie. They were both 21, and I'm thinkin this is finally the night I can tell my buddies about. :laugh: Me with 2 chicks, almost heaven. :drool:

The Spanish hottie had her zipper down when the blonde was in the bathroom. She was playing with it, up and down, drivin me crazy. She asked me to help zip it up, saying it was "stuck". I had pliers nearby and helped zip her up, but tried to get something going at the same time. She pushed me off, and said hey what the heck are you doing, I just wanted help with my zipper!

So my blonde fantasy girl comes back, the black haired girl says nothing, but they keep giggling. I'm too stupid to know if they are goofing on me or planning an attack. I try to keep cool, but I was so drunk I could barely walk, and the stuff we were smokin didn't help it any. :wheeeee:

Somehow after 15 minutes more of this, they decided they wanted to crash for the night. ***!!!! I set them up with sleeping bags and blankets, and left the garage, kicking myself for not being able to close the deal. :beatin:

My sixth sense told me they weren't going to sleep. I listened at the door, and heard moaning coming from upstairs. These 2 hotties were in the midst of a passionate lesbian vacation. I so badly wanted to be part of that action, waited until the moans got louder and louder, and crept back to the ladder to climb it.

They heard me, and said, hey what are you doing back here? I had no game, said something stupid like "mind if I join in?" :dribble: But it was not happenin. They blew me off and told me to go to bed, by myself. Ouch. :(


We always had people in and out of our house. So the next morning, some of my brothers friends came by looking for him. They saw me comin out of the garage, and the 2 hotties a little while later as the girls went to get cleaned up in the shower. These kids were patting me on the back and trying to high 5 me. I knew it would increase my rep, but I couldn't ride out on the storyb they thought had happened. I was still embarassed so all I said was: "Dudes, it ain't what it looks like! Maybe someday I'll tell ya about it, but not today." They still thought I got it on with these chickadees, but at least tried to be honest.

I had some other stories centered around that garage where the outcome was a lot better. I wasn't always the lame loser I was that night. It just didn't work out for me and older chicks until I was around 25. That's all for today, people. ;)