Something had changed. It wasn’t that I had lost my attraction to her. She’s a goddam smokeshow! And the past times we fucked had always been a ton of fun. I wasn’t sure what it was, but the moment she hopped on my dick, we both looked at each other, laughed, and said, “No, we’re not doing this.”
Thank God both of us were on the same page. If only one of has felt that way, it could have been awkward. Luckily, that wasn’t the case.
(This movie was unwatchable and perpetuated many false tropes about having sex with friends but I love Mila Kunis! I also still like JT. Don’t judge me!)
Maybe things will change. Maybe it was just that sexual group setting, and there was an ineffable vibe we both picked up on. Or maybe we won’t hook up again. Over the past few months, she and I had become really close. I view this person like both my mother and sister. And while I love me some incest porn, I have zero desire to sleep with anyone I’m related to.
But this whole situation got me thinking: When you’re a boyslut, and all your friends are boysluts, which friends do you decide to sleep with, and which ones do you not?
But before I can answer that, I have to answer: Why sleep with friends at all?
It’s often a beautiful thing to explore the lines between platonic friendship and sexual, romantic partner. You get to know someone on a deeper level. It’s like, are you real friends if you haven’t tasted your bestie’s booty?
I think when you include an element of sex with your friends, it enhances your relationships. Sex is vulnerable. You see another side of a person during sex. You get to know them more intimately. And through sex, you get to show your friend a different way you love and care for them.
You also know what they’re talking about when they discuss their sex life once you’ve experienced it firsthand. Say they’re having insecurities about having a small dick, you can respond, “No, I’ve had that inside of me and can safely say it’s not small,” or, “Yeah, it’s on the smaller side, but you ate me out until I came my face off, so I don’t think you have anything to worry about.”
Additionally, you trust this person. It’s (theoretically) safer to hook up with a friend than a random person you meet on Tinder, Grindr, Hinge, etc. Last but not least, it’s fun and pleasurable. Maybe I should have led with this reason first, but it’s like, Zach, don’t overcomplicate this. Most of us really like having fantastic sex, so if we can have it with our friends, all the fucking better!
Okay, with that out of the way, let’s go ahead and answer my original question, starting with the times when you shouldn’t sleep with a friend.
When either of you is a messy bitch!
Tough love time. We all have those friends—and if you don’t, then you’re the friend—whose sex and love lives are constantly enveloped in drama. As a friend, you’ve managed to steer clear from the chaos, but that’s because you haven’t rolled around in bed together naked. Remember, there are plenty of people to have sex with, so there’s no reason to get all wrapped in your friend’s mishigas for an orgasm.
When you or your friend haven’t been able to navigate it before.
Have you slept with friends and every time it’s turned sour afterward? Well, that’s a sign that sleeping with friends likely is not for you. Not everyone can sleep with their friends. In fact, I’d argue most people cannot since it can be difficult, confusing, and emotional to navigate. There’s nothing wrong with you for not being able to take your BFF to downtown poundtown. It doesn’t make you less mature, less “woke,” or less open-minded. It just means that blurring the lines of friendship isn’t something that’s for you, and that’s totally okay. That’s why hookup apps exist!
When you don’t really want to.
This should be obvious, but I know in the past—especially in college when I struggled rejecting folks—I used to go along with sexual encounters just because it seemed easier than saying, “I really don’t want to do to this.” Don’t be College Zach. Have sex because you really want to, not because it’s easier than rejecting someone. (Spoiler: Sleeping with someone and then ghosting them is far fucking worse!)
In a similar vein, don’t pity fuck them. You should never pity fuck anyone. Have many of us done it to spare someone else’s feelings at some point in our lives? Yes (please refer back to College Zach), but that’s not what being a boyslut is about. Being a boyslut is about owning your sexuality and doing what you want. If you don’t want to have sex with a friend but think doing so might help them with self-esteem issues or something else, suggest a therapist instead. (The more I think about it, there really are so many reasons why you shouldn’t pity fuck your friends. I’m not going to get into all of them—just don’t!)
Alright, so when can you fuck your friends?
When you can openly talk about it.
If you both need to be drunk in order to fuck, nope! You don’t get to bone! You need to be able to have the awkward and uncomfortable conversation beforehand where you say, “Hey! I won’t be upset if you’re not down, but I’ve recently had this strong attraction to you, and I actually wanna have sex. Would you be into it?” If they’re open to the idea, then you can both share your desires. “I don’t want anything in our relationship to change, but let’s fuck and see how it goes? If it goes well, maybe we do it again? But maybe we just need to do it once and get this out of our system!”
After, you have a mini check-in to see how they’re feeling and if they’d be down to do it again. You may be thinking to yourself, “This takes all the fun out of having sex with friends!” If you feel that way, then don’t fuck your friends!
A lot of things can go wrong when you fuck friends, especially if you haven’t done it before, so yes, I want you to take the proper precautions!
When you won’t be upset if they decline.
When you ask them if they’re down to fuck, they may say, “Omg, no, I don’t want to fuck! I see you just as a platonic friend,” or “I view you like my brother.” If that’s their response, DON’T BE WEIRD. Handle the rejection gracefully and move on. “Totally, I get that!” And that’s it. Don’t ask why they aren’t down. Don’t ask if they think that may change down the line. Don’t ask anything else. You got your response. Move on!
What to do if one of you “catches feelings.”
You may have sex with your friend once, twice, or few times and then realize, “Oh, shit, I really like them and want to be more than friends.” YOU HAVE TO SAY SOMETHING. For the love of God, don’t keep sleeping with them and hiding your emotions. That is a recipe for disaster. I would say, “So, I’m actually starting to like you as more than friends. If you don’t feel the same way as me, then we should stop sleeping together.” If they feel the same way as you, BAM, you’re now dating. If not, it will be awkward for a moment, but crushes come and go. Eventually, your feelings toward them will return to a place of friendship.
Final thoughts:
As I reread this little post, it’s clear that the majority, if not all of my recommendations don’t just relate to friends. If you can’t handle rejection, you shouldn’t be having sex with anyone. If you can’t communicate, no sex for you! And you should always be having sex when you want to and not because it seems easier than saying, “No.”
This just speaks to how sex with friends doesn’t actually have to be that much more complicated than having sex with someone you don’t know. Or, another way of looking at it: It’s equally as complicated as having sex with someone you don’t know.
So fuck it, as long as you and your friend(s) are communicative, honest, and down, why not give it a shot? If you need a third person to be the buffer, just DM me.
Thank you for following BOYSLUT! This is a free post that is available to everyone. If you subscribe, you’ll get unlimited access to non-fiction erotica written by myself and other writers. I’ll also love you forever!