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Old 09-03-2008, 08:19 PM   #51
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Go back to school, little boy. ;)
Sorry that was probably *the* dumbest thing i've ever said on this forum.
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Old 09-03-2008, 08:19 PM   #52
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to shut up, look cute and get it up fast and often.
that is absolutely right girl!
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Old 09-03-2008, 08:20 PM   #53
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Pics or it didn't happen...
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Old 09-03-2008, 08:32 PM   #54
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I guess it will be almost the same for you .. age does not really change too much
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Old 09-03-2008, 08:34 PM   #55
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bring her AARP card for her 10% discount ... the money saved will help on astroglide
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Old 09-03-2008, 08:56 PM   #56
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Sorry that was probably *the* dumbest thing i've ever said on this forum.
Kudos for realizing your ignorance. Welcome back to the world of (some) adults.
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Old 09-04-2008, 02:23 AM   #57
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Depends on what you are doing with her. If you are going for dinner in a restaurant then have a few glasses of wine (admittedly I think Jaegermeister is wine) and see what happens.

If she's going to yours or vice versa then it's pretty much on. And you will be very tired in the morning.. I had something similar on saturday night and went to sleep about 5am. I was then awoken at 9am with the phrase "Shall I have a shower or are you gonna fuck me again first?" I think that says it all..

There are pics but I don't know any of you well enough to share..
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Old 09-04-2008, 02:28 AM   #58
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What expectations does a 40 year old woman have of a 27 year old like me?
uhhhhhhh

dude im 22 and even i know the answer to that.
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Old 09-04-2008, 03:24 AM   #59
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Sit down, shut up, and hold on
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She will wear you out. Women hit their sexual peak in their 40's (trust me on this one). ;)

Like others said, don't play any bullshit games. Anything you can come up with we've heard it all before - a lot. And it's already old. Be yourself, be honest and have a great time
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As the resident cougar around here, I would have to say that my requirements are what ImortylPussycat wrote but with the BFE. Women my age want to be made to feel young again but still be trteated lioke a lady. Do this and she will rock your world!
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Old 09-04-2008, 03:26 AM   #60
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What expectations does a 40 year old woman have of a 27 year old like me?
big cock
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Old 09-04-2008, 03:33 AM   #61
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Compliment her on her crystal candy bowl she has on her coffee table.

Don't play too much with her doylies.

Its better you just don't talk either. If she asked you out, its cause she already wants to fuck you. Unlike 20 something year olds, cougars usually know what they want and how to get it.
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Old 09-04-2008, 06:21 AM   #62
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Old 09-04-2008, 06:21 AM   #63
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havin been on both sides of gamitt dating woman half my age and 10 -15 my elders .. Like the board cougars (ya know I luv ya) mentioned .. 40 year olds can sustain longer then 20 year olds ... so be on in best form (y might want some aids ie: toys, creams or a good squirt hand) she will throw you if you can't sustain her sexually ..LOL
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Old 09-04-2008, 09:19 AM   #64
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I can't wait for my wife to be 40 LOL
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Old 09-04-2008, 09:26 AM   #65
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stick it in here ass. all the 40+ chicks love this.
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Old 09-04-2008, 10:36 AM   #66
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Im 28 and I wouldnt mind dating a 40 year old. But I dont think I could be together with her!
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Old 09-04-2008, 10:37 AM   #67
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be serious. talk slowly. mean what you say. look straight in her eyes. and then fuck her madly.
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Old 09-04-2008, 10:43 AM   #68
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I prefer older women as well, and at my age, something has to change soon, or its gonna get nasty.
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Old 09-04-2008, 11:08 AM   #69
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uhhhhhhh

dude im 22 and even i know the answer to that.
Nah you're a fucking kid and I too thought I knew everything at that age. When you get older you start realizing you don't know as much as you thought you did.

haha you will someday day see what I mean young grasshoper.

The advice from guys is not bad but I really wanted to hear what the woman cougars of GFY had to say and they pretty much said what I thought they would.
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Old 09-04-2008, 11:15 AM   #70
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chances are if shes dating someone younger its because she probably thinks guys her age are boring. take her out and do something fun, and show that you have your shit together and aren't as immature as most guys your age.
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Old 09-04-2008, 11:15 AM   #71
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My advice is to date her daughter
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Old 09-04-2008, 11:16 AM   #72
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My advice is to date her daughter
Her daughter is 9, no thanks, hahaha
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Old 09-04-2008, 11:17 AM   #73
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I prefer older women as well, and at my age, something has to change soon, or its gonna get nasty.
haha that was funny.
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Old 09-04-2008, 12:25 PM   #74
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Old 09-04-2008, 12:27 PM   #75
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Her daughter is 9, no thanks, hahaha
i mean the one she hasn't told you about yet cuz she doesn't want to scare you off
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Old 09-04-2008, 12:31 PM   #76
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hey don't think just do it if you wanna fuck
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Old 09-04-2008, 12:35 PM   #77
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Old 09-05-2008, 06:50 AM   #78
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Haha, I thought I was the only one who did this! But I'm not quite 30 yet...
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Old 09-05-2008, 07:02 AM   #79
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So I have messed around with older women before but never really took one on a date to be honest. Any tips would be great. I'm use to dating 21-23 year olds so there is a 17-19 year age difference there, totally different ball game. I might have a little game with girls my age but I'm like a young deer in headlights right now.

What expectations does a 40 year old woman have of a 27 year old like me?
Don't dress like you are in your avatar and you'll be fine.
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Old 09-05-2008, 07:27 AM   #80
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Old 09-05-2008, 09:55 AM   #81
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I am only in the 30's but have tended to date younger guys more often than not. What usually attracted me to younger vs older guys are a few things.
1) less baggage (hypocritcal I know being I have more baggage than most 22yr olds)
2) Not as set in their ways and less likely to turn down doing fun things bc they feel the are to old or mature for it.
3) Younger guys I have noticed are usually MORE open to relationships and sharing how they feel (see 1)
4) Sex, Sex, Sex, Sex,Sex

And with an older woman if you ask her what she is looking for you will most likely get a straight answer vs little girl drama.
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Old 09-05-2008, 09:57 AM   #82
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I am only in the 30's but have tended to date younger guys more often than not. What usually attracted me to younger vs older guys are a few things.
1) less baggage (hypocritcal I know being I have more baggage than most 22yr olds)
2) Not as set in their ways and less likely to turn down doing fun things bc they feel the are to old or mature for it.
3) Younger guys I have noticed are usually MORE open to relationships and sharing how they feel (see 1)
4) Sex, Sex, Sex, Sex,Sex

And with an older woman if you ask her what she is looking for you will most likely get a straight answer vs little girl drama.
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Old 09-05-2008, 10:03 AM   #83
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be prepared to stay in bed for awhile.. always a good idea to bring your own condoms..
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Old 09-05-2008, 10:12 AM   #84
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Damn this a hot topic. I want to start a cougar club, kinda like the fight club, that would be awesome.
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Old 09-05-2008, 12:04 PM   #85
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My advice to you is forget everything everyone has told you and be yourself. It's a 40 yearold woman.. if she doesn't like it.. who the fuck cares.. You gonna marry the bitch?

she's prolly nasty compared to a 20 yearold girl you should be hooking up with..

prolly has more baggage and stress in her life also..

40 yearold women hook up with 20 yearold kids for the same reason hot straight girls hook up with butch dykes..
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Old 09-06-2008, 04:37 AM   #86
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Theres not much difference, exept she is most likely a better cook and better in bed. So go for it! Older girls are my thing too, so you cant go wrong
Just dont try to get her drunk like a collegegirls.. girls in that age usually know how to drink

no need to add words to this post.. he's right
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Old 09-06-2008, 05:16 AM   #87
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Damn this a hot topic. I want to start a cougar club, kinda like the fight club, that would be awesome.
That was a great movie
https://youtube.com/watch?v=k3VonKZswgA
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Old 09-06-2008, 06:19 AM   #88
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Nah you're a fucking kid and I too thought I knew everything at that age. When you get older you start realizing you don't know as much as you thought you did.

haha you will someday day see what I mean young grasshoper.

The advice from guys is not bad but I really wanted to hear what the woman cougars of GFY had to say and they pretty much said what I thought they would.
young grasshoper lollll

bro you're a tool. you are the one on here asking about what are the intentions of this 40 year old thats been talking to you. obviously shes wants some young stinger. like i said im 22 and i already know that shit.

i was sitting in the bar at changs this week for lunch talkin to this cougar, that tells me shes married has an 18 year old daughter, owns a starbucks, and she gives me her card and tells me we should hook up saturday night for some cocktails. you should have seen all the attention i got from the 20yo hostesses after that broad left.

all you have to know is older broads don't play. they aren't there to talk about their new fucking iphone and how many games of beer pong you won this weekend like some dumb 20 year old blonde is. they like some conversation and maybe a drink or two but after that they want to get straight to the point. only because most KIDS like you don't know how to stop beating around the bush and straight up ask them if they wanna fuck is the main reason you have no experience with them.

fucking kid hahaha honestly that made me chuckle.. dude you don't know shit. i'm not one to brag but i've fucked more 30 year old women than 20 year olds. there are even a couple women in this industry that could attest to that. just because you don't know shit doesn't mean i don't.
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Old 09-09-2008, 04:48 PM   #89
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Old 09-09-2008, 05:31 PM   #90
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young grasshoper lollll

bro you're a tool. you are the one on here asking about what are the intentions of this 40 year old thats been talking to you. obviously shes wants some young stinger. like i said im 22 and i already know that shit.

i was sitting in the bar at changs this week for lunch talkin to this cougar, that tells me shes married has an 18 year old daughter, owns a starbucks, and she gives me her card and tells me we should hook up saturday night for some cocktails. you should have seen all the attention i got from the 20yo hostesses after that broad left.

all you have to know is older broads don't play. they aren't there to talk about their new fucking iphone and how many games of beer pong you won this weekend like some dumb 20 year old blonde is. they like some conversation and maybe a drink or two but after that they want to get straight to the point. only because most KIDS like you don't know how to stop beating around the bush and straight up ask them if they wanna fuck is the main reason you have no experience with them.

fucking kid hahaha honestly that made me chuckle.. dude you don't know shit. i'm not one to brag but i've fucked more 30 year old women than 20 year olds. there are even a couple women in this industry that could attest to that. just because you don't know shit doesn't mean i don't.
Haha you're funny dude. This post was never about fucking, more about relating to her Intellectually. I'm glad I'm worth all the writing though. You cute little peep squeak, you.

By the way you are on my ignore now so don't waste your time.
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Old 09-09-2008, 05:39 PM   #91
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you'll more than likely get schooled
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Old 09-09-2008, 10:49 PM   #92
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Haha you're funny dude. This post was never about fucking, more about relating to her Intellectually. I'm glad I'm worth all the writing though. You cute little peep squeak, you.

By the way you are on my ignore now so don't waste your time.
what? you mean guys go for older chicks for the conversation?
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Old 09-09-2008, 10:54 PM   #93
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this thread is funny on many levels. lol
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Old 09-09-2008, 10:55 PM   #94
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Turn the lights down before she gets naked.
Thats only for girls your age doll

Wtfent..Have fun..take notes, fuck fuck fuck..cause that is probably all she wants.
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Old 09-09-2008, 11:11 PM   #95
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I've only dated one woman over 40 and have to agree WITH all that was said here man. Hold on to your hat, you are in for a wild (and pleasurable) ride! bring plenty of water and pack your a-game. She will out-fuck you, out wit you and leave you with your head spinning.... You WILL come back for more... if she lets you!


As someone mentioned earlier.. BFE (Boyfriend expeRience...). Make her feel good, listen to her and DON'T BE BORING!
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Old 09-09-2008, 11:59 PM   #96
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Turn the lights down before she gets naked.
I hate to break it to you but SHE WILL KNOW YOU HAVE A SMALL PENIS EVEN WITH THE LIGHTS OFF.
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Old 09-10-2008, 12:06 AM   #97
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My advice is that not all women are the same so generic advice is pretty much useless. But what the hell, here's mine:

Know your place in the world; you are her inferior. Don't act like you're her equal in life experiences, knowledge of wine or film or ANYTHING unless you want her to laugh at you. Don't act like Red Robin is fine dining or let her know you've never bought a meal anywhere besides taco bell unless it's because you honestly don't have money and you say so. Don't try to be good at being HER age, just be good at being YOUR age (without assuming she'll be interested in doing whatever it you like to do, besides fucking).

And above all, don't try to teach her "new" tricks about her body like you know shit about her pussy that she hasn't already figured out a la "I saw Cytherea do this in a porno and now I think YOU should squirt twenty five feet".
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Old 09-10-2008, 12:17 AM   #98
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Just because she is older doesn't mean she is a woman of the world. She could of been sitting in a trailer park for 40 yrs. lol Also age does not make one good in bed. A 40 yr old can suck just as much as a 20 yr old. It's the person. Here is my advice just be you, if she said yes there was something she liked about you. Just be you.
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Old 09-10-2008, 12:57 AM   #99
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Originally Posted by wtfent View Post
She has a beautiful body, nothing to worry about there.
Clothes add a level of obfuscation that sometimes confuses the perception of what she will look like naked. 18 to 25 clothes or no clothes the perception matches the reality 98% of the time. 25 to 30 wildcard variables pop up. 30 to 35 more wildcards. 35-40 a large percentage of women (and men) are losing it by this point unless they are really on top of it and even by then you are getting the effects of the sun damage, alcohol damage, and more importantly... the effects of gravity and the degradation of the skin's elasticity.

If your 40 year old has had kids and a normal 20 years of cock... watch out. You will definitely want to take baddog's advice.

Last edited by davidd; 09-10-2008 at 01:00 AM..
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Old 09-10-2008, 01:05 AM   #100
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Originally Posted by Trixie View Post
My advice is that not all women are the same so generic advice is pretty much useless. But what the hell, here's mine:

Know your place in the world; you are her inferior. Don't act like you're her equal in life experiences, knowledge of wine or film or ANYTHING unless you want her to laugh at you. Don't act like Red Robin is fine dining or let her know you've never bought a meal anywhere besides taco bell unless it's because you honestly don't have money and you say so. Don't try to be good at being HER age, just be good at being YOUR age (without assuming she'll be interested in doing whatever it you like to do, besides fucking).

And above all, don't try to teach her "new" tricks about her body like you know shit about her pussy that she hasn't already figured out a la "I saw Cytherea do this in a porno and now I think YOU should squirt twenty five feet".
You forgot to add:

Do not "take it easy" the first time. You need to show her how "young people" do it. If she is new to the track because of a recent divorce you need to make it easier for yourself and for those that will come after you. You will be doing her in the ass... you will be finishing in her mouth regardless of what orifice got you to the point of completion.
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