Dating a cougar means that things are extremely kinky between the satin sheets. As I have gotten older, I have felt more and more sexual. Rumors may circulate that your sex drive declines with age but I am here to put that to rest. Milfs love to try a ton of different things in the bedroom, from using toys to adding orgy members. One of the most beloved sexual pastimes of the milf though is roleplaying.

If you really sit back and think about it, milfs are sort of roleplaying on a daily basis. There is always an element of performance in the air that feels like playing a character. The idea of the hot mom sort of is a character in itself. Who is she? She’s an experienced older woman who wants to explore her sexuality with a younger and less experienced man. There are endless roleplay ideas that fit nicely into that narrative, but which ones are the best?

As a cougar and a milf myself, I have a lot of experience in role-playing. I’ve tried out multiple characters and sexual situations. Coming to the conclusion of what my favorites are is a slight difficulty. But I have also consulted with my other milf friends to determine the ultimate roleplay situations we love to play out. Here are the top 4 roleplaying ideas that can be performed between a cougar and her playboy.

Number One: Milf and pool boy

This role-playing idea never goes out of style and it hits pretty close to the real life version of events between a milf and her lover. Think of this role-playing idea as the Mrs. Robinson version of playing between a cougar and yourself. To get the most out of this scene, you should really go for it. Set up your surroundings to match the characters. Hell, maybe you really are a pool boy courting a milf! If the milf who you are dating has a pool then maybe you two can start there. She’s tanning her sexy older body and you are doing the pool chores. Then she asks you to lather her with sunscreen and takes her top off. Better yet, use oil so that you can use it as a lubricant later. You can easily see where this is going, yes? Jump into the pool together, do it by the pool, or on the sunchair.

Number Two: Teacher and teacher’s pet

A bad boy and a disciplinarian. Were you the kind of kid who was the class clown, always got in trouble, and saw detention as an honorable place to be sent? Now that you are older and attracted to milfs, it sounds like being disciplined is something you are very much attracted to. Use that energy in this role-playing scenario between you and the cougar. She is the teacher and you are the student. In life, that is pretty much how it is between the two of you anyways because she has the life experience which you lack. Go out and buy a long ruler for some fun disciplining that can take place in your makeshift bedroom/classroom. Have you been a very bad boy?

Number Three: Officer and criminal

Chaps who fancy milfs and cougars often love to be put in their place. They enjoy and even sexualize the feeling of losing control. This is because a milf is usually the person in the position of power in a milf and man relationship. Dating a milf probably conjures up feelings of nervousness and inadequacy that are kind of hot. This is where the officer/criminal dynamic comes in. With this role-playing idea, you can play either the officer or the criminal. It’s more common to see the milf as the officer, but there can be a situation in which the criminal has more control. Maybe the criminal gets ahold of the handcuffs. You and your milf. have a lot of creative license with this one!

Number Four: Boss lady and intern

Are you dating a milf who is a boss lady in real life? Maybe she even has her own office where you two can escape to in order to live out this incredible boss/intern fantasy. If she does have her own office space, take full advantage. After working hours, or even during depending on the privacy that the office provides, you can pretend to be her little intern boy. As a task she might ask you to please her… doesn’t that sound fun? You might have to show her that you’re the right man for the job… if you catch mhy drift. But maybe, she’ll want to show you how it’s done first so that you don’t make any mistakes. Exhibitionism comes into the scene if you play out this scenario during her working hours. There is something very sexy about potentially getting caught!

Now that you have some ideas, it’s time to go impress your milf. Maybe take her out on a date first, court her, and bring up the idea of role-playing. I can assure you that she won’t be disappointed. Introducing role-playing into the relationship will probably impress her!