If you’re not looking to get into a serious relationship, but you are looking to get into a woman’s knickers on occasion, then you should be out their pursuing a Friends With Benefits setup. Seriously. It’s important to have sex every once in a while.
If you are fortunate enough to find yourself in a FWB scenarios here are a few pointers to ensure sustained success:
Do not be overly romantic, but do be complimentary. No gifts, no sweet nothings whispered in ears, no dates thinly disguised as friendly hangouts. This is not about romance, and inserting romantic gestures into the arrangement can create all kinds of problems for one or both of you. But don’t be afraid to be like “your ass looks fantastic today!” or to give her a high-five and a compliment about her Reverse Cowgirl prowess.
Lay out the ground rules at the commencement of the arrangement. Make sure the two of you are on the same page re: what this arrangement means, and what you will do if you start developing feelings or if you begin dating a person. During this discussion, you should also broach any ground rules that come with if/when you are going to have sex with somebody else. Safety is important.
Realize that you have no right to envy or protectiveness. These things are not (unless otherwise defined when laying the ground rules or afterward) exclusive arrangements. You’re going to be keeping your eye open for other opportunities, and she is going to do the same. Don’t get butt-hurt about it if she has sex with someone else and you find out. And if you do, that may be signal that you’re developing feelings beyond naked friendship.
If she goes incommunicado for a bit, don’t allow yourself to get upset. She’s probably been boning someone else and doesn’t really want to talk with you about it. AND DO NOT ASK HER ABOUT IT.
You should expect nothing beyond some fun and an orgasm (the latter depending on how drunk you are, of course).
Let her be the one to reach out. And make sure that this is how it’s going to be when you’re laying out the ground rules. You don’t have to play the stupid games inherent in the courting process when you’re just working on getting each other’s rocks off. Be very attentive to her pleasure, because that’s what will make a return customer out of her.
Let her spend the night if she wants to. It’s not safe for women to be heading home at 3 a.m. And again: she’s more likely to keeping coming around if you’re not kicking her out moments removed from when you were inside of her. (But if she is leaving some nights, don’t miss the opportunity to say something like “Leave the cash on the dresser and get the hell out of here.”)
Be very honest and open about what you’re looking for sexually. If you’re going to enter into something like this, there’s no reason you both shouldn’t get as much out of it as possible. What I’m saying is if you want her to choke you, tell her.
Go down on her. Seriously. Don’t be a vagina about it. Especially if she has gone down on you. Quid pro quo.
Be very honest about what you’re feeling. This may seem counter-intuitive in such an arrangement, but you need to feel comfortable in the notion that you can talk to each other when one of you starts to have romantic feels for the other, etc.
Realize that no FWB arrangement lasts forever. They all come with an expiration date. They end, whether it’s because one of you has met somebody they’re getting serious about, and as such need to stop boning others, or because your whole thing has evolved into something more like a romantic relationship. If you’re not the one who ultimately calls it off, don’t be a dick about it when she does.
Keep it mostly quiet. FWBs don’t really post it as their relationship status on Facebook.
Always keep your eye out for the next thing. This may seem crass and dickish, but if you’re an FWB and you’re not doing this, you’ll inadvertently get too clingy and attached.
If she doesn’t know them already, keep her away from instances where she might meet your parents or other family members.
Make sure you’re having fun. That’s what it’s all about, man.