How to get middle aged woman at the store?

And this is why I don't see the appeal of younger men....


If you want a "Older, mature" women, articulate yourself like an older mature man.
Whatever frat boy told you that older women don't want relationships was high. Please...
 
Assuming you're serious, I would advise you to be upfront about your intentions. A 20-year-old would have to be coming on pretty strong for me to realize that's what he was actually doing because it would be so unexpected. Strike up a conversation with her, maybe about some item you're both looking at, ask her for advice about a product, etc. Then throw in some compliments and, if she's receptive, tell her you've enjoyed chatting with her and ask if she would mind your calling her sometime to chat some more.

Now for some other advice: Don't assume every middle-aged woman is interested in a 20-something-year-old guy. I've always preferred men at least a little older than me, even when I was in my 20s. Be prepared for possible rejection and don't take it personally. Good luck.
 
Terms like "older" and "middle age" are relative. One man's "cougar" is another man's "trophy wife."

Most of my relationships have been with women 10 to 15 years older than me. This started when I was in my twenties and is still true after recently turning fifty. A 10 to 15 year age gap is the most common in OW/YM relationships. So, if you are 20 you might have your best luck with a woman between the age of 30 and 35. I would suggest dating sites instead of supermarkets. Just go on one of the more popular sites like POF or Match and attempt to make contact with women in the age range you are seeking. My experience is that 1 out of 3 women are interested in men a decade or more their junior and about half of those would be interested in me in particular due to personal preferences like height, hairstyle, looks, etc...

You do need to have game, maybe even more than when it comes to finding women your own age. The idea that a guy who is a failure with women his own age will be successful with an older woman is a myth.
 
Cougars come after you, not the other way round. If she wants you she'll create a pretext to get you alone in her home. I used to get phone calls to come over and check out something that really wasn't broken. If its a strange noise in the attic look for it and offer to stick around for a while when you find nothing. Be alert for the hints, and respond.
 
How to get middle aged woman at the store?

Aisle 4, next to the toilet paper.

What are you going to do with her at the store, bend her over the cart?

I was wondering what kind of store you were thinking of . . .

Middle aged women of my acquaintance tend to be touched, amused but ultimately not interested when young guys come on to them though. However maybe when they drag them back their lairs to be fucked senseless they don't tell me!
 
The mothers of my girlfriends usta put their hands on me, and I worked with the mother of a classmate. The mother usta come to the hospital when I got bit by dogs, and other minor emergencies; invite me over for dinner, etc. After school I enlisted and usta stop and see her when I was home on leave...her daughter was away at college then.
 
I'm 20 and I love middle aged women for 3 reasons: They are curvier, more mature and don't really want relationships. How would I proceed to convey to her (them) that I just want to have fun and nothing to serious, at least for awhile?

You 'd better correct your statement as follows: I'm 20 and I look for a middle aged woman. She must be curvy, mature and not really want relationships. I just want to have fun and nothing too serious, at least for a while.

Then post it on the Literotica Personals.
 
Like books, it's generally easier to get your middle aged women online. Maybe you should start perving the Amazon review sections?
 
Offer to carry her groceries to the car, then, once you've loaded them in the back, tell her you provide the "full service option" if she'd care to remove her panties and lie down in the back seat.
 
You need a special set of skills to pick up the kind of woman you want. Here is some useful information.

- They like their knights in shining armour.
- Chivalry is important.
- Don't call them ma'am. "Lady" is more appropriate. If her name is Jenna, call her Lady Jenna.
- They like castles and shit.
- Perhaps digging a moat around their house would be nice.
- They prefer white horses, I am told.
- Often times there are dragons holding them captive in a castle.

The most difficult skill of all, when picking up a woman of the Middle Ages, is the ability to time travel. Right now, your youngest Middle Age woman is, AT BEST, about 500 years old. Her bones would be so brittle, I doubt you'd even find her worth your time, if you're looking for a quick lay. So, I'm suggesting that your best bet would be to go back about a half a millennium and try your luck there.

May I at least suggest a woman of the Renaissance? Probably several hundred years fresher.

We all have our kinks. But a Middle Ages woman is probably one of the more difficult ones to fulfill. But if you find one, best of luck. Keep us posted!!!

Edited to add: You could try one of those festivals where people dress up like they are in the Middle Ages and do all that shit. But, I realize that's not the real thing and it's like substituting masturbation when you want sex.

Do remember, they didn't have razor blades for shaving legs and stuff, during that time.
 
Last edited:
Offer to carry her groceries to the car, then, once you've loaded them in the back, tell her you provide the "full service option" if she'd care to remove her panties and lie down in the back seat.

lol.. there was an older gentleman who helped me with my groceries a couple of years ago. When we got to the car, he asked, "may I buy you a ham? Please.. I want to buy you a ham." I have to admit, it was difficult to decline such a romantic gesture.
 
Very good post my learned friend, pmann.

All I will add is that if you are looking to dabble in the middle regions of maidens from the Middle Ages, be sure to put some chain-mail on your peni.

Gonorrhea, Small Pox, and Plague are just a few of the common gifts that keep on giving, resulting from random sessions of unprotected, nekkid minstrel / maiden jousting.
 
Do remember, they didn't have razor blades for shaving legs and stuff, during that time.
They weren't much for the bathing either--I'm thinking you may want to bring some lysol to freshen things up.
lol.. there was an older gentleman who helped me with my groceries a couple of years ago. When we got to the car, he asked, "may I buy you a ham? Please.. I want to buy you a ham." I have to admit, it was difficult to decline such a romantic gesture.
That is the most awesome thing I have read today. Thank you so much for the giggles because the rest of this day sucked serious donkey dick.

Very good post my learned friend, pmann.

All I will add is that if you are looking to dabble in the middle regions of maidens from the Middle Ages, be sure to put some chain-mail on your peni.

Gonorrhea, Small Pox, and Plague are just a few of the common gifts that keep on giving, resulting from random sessions of unprotected, nekkid minstrel / maiden jousting.
The fleas could be bothersome too, I've heard tell.
 
damm, misread the title, was looking for tips on how to get a middle aged woman to go to a store ( other than for clothes/shoes)....wardrobe full, larder empty!
 
I met a middle aged "cougar" at the grocery store the other day. Picking her up was really easy. First I hit her with a shovel, then I just simply through her over my shoulder. The sex was kind of lame though... She just laid there.
 
Use coupons. Women think men who are thrifty are sexy.

Also make sure you hide things like jock itch spray, wart removal cream and foot powder under the other items in your carriage. Yup.
 
I'm 20 and I love middle aged women for 3 reasons: They are curvier, more mature and don't really want relationships. How would I proceed to convey to her (them) that I just want to have fun and nothing to serious, at least for awhile?


Flash her.
 
Chloroform works. Trying to unobtrusively get them out the store is a different story. Shopping carts are handy but camouflaging her to look like canned goods and dish soap poses a problem. I'd suggest cougar bars at 2 am (or whatever your local tip out time is) sans chloroform. They ought to have enough in their system at that point to be slightly agreeable to going home with you. Especially if her goggles are 6 glasses deep.

Decent idea. Start a small fire on the other side of the store as a diversion first.
 
Back
Top