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How To Date A MILF

Getting the benefits and avoiding the hassles of dating an older woman

MILF sex is some of the hottest, wildest, most uninhibited sex a young man can get. Older women are not burdened with the worries, concerns, anxieties, and insecurities of their younger days. They are comfortable with their bodies; they know what gets them off and stop at nothing to get to it.

They have also been with enough men to know all of our naughty, unarticulated desires. They are expert in hitting those spots that we might be too shy or too ashamed to divulge to sex partners of our own age.

However, it is not always plain sailing. Older women tend to come with more baggage than younger girls. But this need not be a deterrent if the baggage is light and compact enough to handle without undue strain.

The Friend Situation

You may be used to winning over the friends of women you’ve dated with your charm and outgoing personality. If you are not in a purely sexual relationship with an older woman, she will want to introduce you to her friends. A woman who is over 40 will likely have friends of her own gender and age group. That is the one thing you will need to adjust to first. If you are among the current generation of twenty-somethings, you will likely have good friends of both sexes. Wide gaps in age are also not uncommon amongst Gen Yers.

Gen Xers and Baby Boomers tend to be more traditional when it comes to this sort of thing. They are more comfortable with people who are pretty much like them in every respect, which will put you at a disadvantage.

You will be seen as an outsider, and though her friends will not be explicitly rude or indecent they will be naturally suspicious of your motives for dating her. The woman you’re dating is unlikely to break with you because her friends disapprove, but as every man knows it is easier to get on when the latter are on board.

What to do?

Let them get to know you as a serious man of substance first. The primary suspicion that the friends of a MILF girlfriend will have is that you are dating her for her money, her house, and her other material possessions. You can disabuse them of this notion if you demonstrate that you have a plan for and are on a path toward your own material success. Once they’re comfortable with you in this light, you will then be able to show the humorous, more fun-loving side of your personality.

The Family Situation

If you’re dating an older woman, chances are she is divorced with children. If you have made the leap to GILF, then you will have to deal with two generations of her descendants and who knows how many exes. It will not be easy, but it can be managed with a bit of courtesy and common sense.

Your MILF sex-kitten may have children your age. She may be sensitive to this fact and put off introducing you to them. But if she is one of the more carefree cougars out there she may have no qualms about introducing her boy toy (that’s you) to her children.

Assume that they will hate you. And try not to judge them too harshly for it. Put yourselves in their shoes. Would you want some jumped up tween doing your mom?

Make the best you can out of a bad situation. Don’t try to be friends with them; that will only inflame the situation. The fact is you don’t know how you long you’re going to be around, so you need not put too much emotional energy into breaking down the wall of hate. Be polite and kind in all your dealings with them. Do your utmost to show them that you are the soul of pleasantness and generosity when it comes to their mother, and that whatever is between you is real and mutually felt.

Related Video: Use This Phrase To Ask A Woman Out

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About Christopher Reid Chris was born in Washington, D.C. and lives in Britain. He works as a blogger, essayist, and novelist. His first book, Tea with Maureen, has just been published.


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