Unchartered Waters


Confession: I have a crush. This is not exactly breaking news, considering that I am rarely without one. But this latest crush is different. I don’t know this person that well, but based on what I do know this person is smart. Funny.  A great flirt. Interesting and open-minded. We seem to see eye-to-eye on a lot of important stuff and this person is fucking sexy.

Oh and one more thing – this person is a girl.

It’s no secret to you guys that I’ve always been more than a little bicurious (I blame it on playing “sex” with my best friend when I was 8 years old) but lately the curiosity has progressed to full-on lust. And whereas before my attitude toward girl-on-girl action was that if the opportunity arose I’d be down for it, these days I am dangerously close to actively pursuing it. I’m not sure whether I’m in a crisis situation or on the brink of the greatest moment of my life. If I can figure out how to make it happen, that is.

Since I’ve moved from “yeah I wouldn’t mind if it happened” to “I have to have this girl right now”, my mind has been abuzz with the logistics of such a thing. There are a lot of details to wrap my head around. And so I present to you, my dear readers, the practical considerations of girl-on-girl action.

1. How exactly does one put the moves on a girl?

Beyond the obvious and supreme hotness quotient of popping my girl cherry, getting with a woman is more than a notion.  It’s not like getting sex with a man where according to the fools who comment on here even though we know it’s bullshit I can just walk up to him, ask for sex, and get what I want. With girls – or with this girl anyway – it’s going to require some finessing. And that is not exactly an area in which I excel. I am notorious for not making first moves on men and even when I do my “moves” are not all that slick. With a man you can say “are you gonna give me the bum or what?” and he either will or he won’t. But I feel like with a woman I might scare her off.

2. Friend? Stranger? Professional?

What is the ideal level of closeness when you’re getting down and dirty with a girl? On the one hand I think that with a friend there’s a greater comfort level; you might be better able to discuss things before and manage expectations. But then there’s a pretty huge ick factor involved with contemplating licking your homegirl’s coochiesnorter. Which leads me to think that a stranger is better. But then that means you have to have sex with a complete stranger and that’s also kind of icky. I can think of very few things more desperate and thirsty than to put an ad online to find a man to fuck, but is it okay to do it if you’re looking for a girl?

4. Turnabout is fair play right?

There was a time in my life where my policy on girlsex was that if a girl wants to go down on me that’s fine but there is NO WAY I’m going down on her. I’m at the point now though where I think I could probably do it for the right girl. But um, what if I can’t? Is this like with men where you can say “I don’t do that” and the matter is dropped? Is oral a requirement?  On The L Word you hardly ever see girls going down on each other; can I get a pass on that if I’m not feeling it?

5. Oh and where is that Cunnilingus 101 Post?

Assuming that I suck it up and get motivated to lick the love below, what is it exactly that I’m meant to be doing down there? Let’s keep in mind that I’m largely anti-receiving oral so this is not one of those “oh just do what feels good to you” type of situations. I feel like I’m going to end up flailing around like a child bobbing for apples at a Hallowe’en party. Which would tarnish my “epic in bed” status that I have worked so hard to maintain. And we can’t have that.

6. With a side of sausage?

Do I need a man on the premises to supervise the operation? In a way that seems smart – that way if I choke on the whole eating nani business at least I have an alternative to offer. On the other hand though I don’t know what man is going to sit there and watch two girls explore unchartered territory and not want to slide in somewhere. And while I am never ever mad at the idea of a penis sliding into a pussy, I’m not sure my first girlfuck is the place I want that to happen.

These are the things I worry about.

So dear readers, do you have any advice for me? Is active pursuit of pussy a good move or is it better to revert to my “if it comes it comes” attitude?  Should I get out of my head and go for the gold or are these valid questions I should answer before diving in? I know some of you have been down this road – any advice for me? Men – encourage me by reminding me how fucking hot this would be.

bag lady. digital nerd. beauty junkie. shoe whore. i'm a sucker for big words and box-fresh kicks. know a little bit about a lot of things and have something to say about everything.

Comments 31

  1. Menelaus says:

    I think you should approach the situation just like you would any other situation.

    And faced with the decision of being asked to leave the room or watch and not touch, most men will choose to stay and watch.

  2. Starita34 says:

    Seriously Max, why not just announce to everyone that we’re in love? Geesh! You feature me yesterday and then “mysteriously” declare your girlcrush the next day? A little privacy please? Could you be a lil more obvious? I never woulda pegged you as an oversharer! But even Ray Charles saw this not so subtle love letter. I told you it was my first time too, relax! 😉 Just joshin folks, little thing we like to call a “joke” To Max: Unless you’re gonna do it #Nelly

    If that pic isn’t motivation enough to do it, I don’t know what is! I say muffdive right in. The first time you gave head you didn’t know what you were doing. The first time you rode a dick you didn’t know what you were doing. The first time you took back shots you didn’t know what you were doing. But you survived, you took notes, and eventually you became comfortable with it. and c’mon, you’ve seen enough lesbian porn to be an old pro already!

    I’m 100% with ya on setting expectations though. WhenIf I ever hook up with a girl, I will be on vacation in a foreign city, preferably Vegas, and we shall never speak again after the trip is through. It’s gonna be hot, sweaty, lustful sex and that’s it. Come morning, I’m in the wind. You gotta manage your own expectations too. Women are hot, women are soft, women are sexy, women are giving…but they’re no man. They’re like Chinese food…you’ll be hungry again in 30 minutes, it’d never last long term. Ladies like you and me, we need a man in our lives.

  3. well if you really want to my advice here is what i suggest you do. find a guy who is willing to do a threesome. a guy you feel comfortable with. explain to him that he might not be able to have sex. find a woman that’s not too close to you but you still feel comfortable around. have a few drinks then go for the gold. before hand you might want to ask the guy for tips on dining out. in the end if you don’t feel like you want to eat the box then let him do it. make sure you ride her face into heaven though. after that you can try a little one on one action with the lady of your choosing. perhaps if its good enough the same woman.

  4. Shash says:

    I just can’t believe your anti-receiving oral, that doesn’t even make sense to me. I’m assuming there is already a post about this that I can get linked too but really…Anti.

    Oh I would suggest asking a lesbian, or going to a queer party and waiting to get picked up. or you could always write one of those letters that says “do you like me? yes, no, or maybe”

  5. smarts says:

    this was an eye-opening read, thanks


  6. Papaya says:

    Anti receiving?????!! Omg!! As good as it feels??!! Giiiiirl lol

  7. Mrs.Brightside says:

    My current source of Sexual satisfaction is a friend who I suspected to be into females but kept men around. We did some flirting and one day she was over watching a movie and I decided to get a little friendlier with my touching just to say I’m game if you are. It was subtle but effective. Nothing happened the first night but the next time we had a movie night after some hair stroking she jumped me and we’ve been enjoying one another ever since. We are not in a relationship because we both feel that we want to eventually end up with a man and there are just some things a woman can’t do. We continuously talk about what is going on between us and anyone else that may be brought in.
    I say all that to say make yourself open it will come to you. Actively seeking takes some of the fun out it to me.
    As for going face first think about getting the girls sucked. The things that feels good to the nips feel good to the clit. If it’s not their first time more than likely they will understand if you aren’t ready to go all the way. Having a guy present is a great excuse for getting the bestie in bed and it will just be written off as a drunken night…;)

    1. Starita34 says:



  8. Kema says:

    Max… I say leave the men out of it! Also, if you drink that will clear up any uncertainties you may have. Not saying I’ve done it or anything…. but it is much easier to lick than suck imo. 🙂

  9. LaLaBakir says:

    All valid thoughts/concerns Maxie

    I have no advice for you. At all. In fact, I’m not sure why I’m even replying.

    Oh, yeah…maybe you shouldn’t do it w/ lesbian you’re familar with. I had an offer of sorts from my lesbian friend that if I ever wanted to get down, she’d be willing to get down as well.

  10. Melissa says:

    Coochiesnorter???? Lol.

  11. streetztalk says:

    Please tape and zshare me the vid of the night. *respectful bow*

  12. crackers says:

    Dearest Maxine,

    I’m very confused…. if you’re not jazzed about burying your pretty face down *there*, what’s the allure for you? Obviously, different strokes (licks, bites, pokes) for different folks but in the hetero scenario, if I can’t get worked up over the idea of going down on a certain man, that’s a pretty good indicator that I’m not attracted to him. And trust me… I get worked up over pulling lint from my belly button, so it takes a lot to turn me off.

    but wait, this is about you.

    expliquez, s’il vous-plait.

    p.s. i’ve seriously thought about hiring a professional for a tutorial.

  13. Geez, Max. I used to be an expert on this subject. I was a lesbian in a previous life you see.. Why else would I love girl-on-girl so much?

    However, I totally forgot all of my old trix. My lesbian trix that is. So.. I’m gonna see about finding a hypnotist to bring it back so I can provide some legitimate help.. though I’m not sure for the life of me how to go about that. Does anyone have any information on how I can go about having sex with a hypnotist for the sake of helping Max have sex with a woman?

    1. Starita34 says:


    2. keisha brown says:


  14. I don’t even know where to begin. Honestly Max, we were cut from the same damn cloth.

    Kema said it….drink up. All the girl-kissing I’ve ever done has involved 3 drinks (yeah, I’m a cheap drunk).

    Secondly, that comfort level needs to be at the part where you’ve MET this girl and possibly have her contact info on your phone but haven’t actually emailed/text her *clears throat loudly*. When I met one of my now best friends, I wanted her. Her ass, her boobs, her mouth, even the way she talked to me made me want to stick my tongue in her mouth. Then she started calling me every day. And we hung out. And I became her “sister”. Ew. That’s when it becomes almost incestuous. I no longer looked at her as a possible lover. No thanks. The same thing happened with my other two best friends. Point is: Don’t let her get too close or else that “ick level” is way over the top.

    And thirdly, I have the same problem re: anti-receiving. So besides heavy petting, licking, kissing, the only other thing I can come up with is a strap-on.

    I think you and I should just fly to Kansas City *shrugs*.

    1. Starita34 says:

      “I think you and I should just fly to Kansas City *shrugs*.”

      I like this idea!

  15. Yoles says:

    max i say if there is a woman that you have in mind you should do it WITH her, a stranger isn’t going to make you feel the way you do around said lady now to your questions

    1- i hope that you have an open dialogue with this lady and that its been flirty flirty already, making the moves usually includes some drinks, light touching i.e. scalp, neck, shoulders and back massages. flirty talk especially during the massages because you get to whisper in her ears and just watch the body language for the next step

    2- definitely someone you know, especially for a beginner a stranger isn’t going to make you feel comfortable

    4- i am of the school of thought that everything is for everybody, yes the thought of muff diving may be intimidating for a while but once the heat is on and you want to make your partner feel good-go for it

    5- pay attention everyone’s bodies let you know what they like. start soft gently lick and suck listen to her breathing, feel the muscles in her legs (are they shaking) watch the muscles of her abdomen, listen to her words, moans, deep breaths, sighs, screams etc, see what she does with her hands… as long as you pay attention you will know exactly how to please her

    6- i say for your first time you don’t need a man there (even though FMF 3somes are the BEST) this is a situation where you take your time, do things over and over again, kiss and touch, talk and lick, relish in each other without having to worry about a dude and him getting his off too

    good luck, keep us posted and enjoy!!

  16. Danielle says:

    I will say this if the thought of going down on a woman is disturbing to you then you are not ready. Just leave it alone until you are. Unless you luck out and find one of those women who are not into cunnilingus then go for it.

    And for the love of God please do not have sex with a strange woman. Yucky yuck yuck!

    And do not have a threesome. If you’re crushin on her, let you and her have that first time together. Alone.

    I am a full fledged card carrying bisexual. I love giving and receiving. I love the smell and taste of a woman. I actually prefer it. I am not a Spaghetti Lesbian: lesbian when wet. I can as easily fall in love with a woman as I can with a man. It’s not just a sexual act. Even when I was just curious the emotional attachment was there.

  17. Carmelita Jones says:

    “Spaghetti Lesbian” LMAO!
    I believe wet also includes alcohol; a few, FEW, drinks is okay but if you (or she) has to get sh*t-faced to do it then it’s probably not worth it.

    1. Danielle says:

      I got that off my kinky facebook. I love it cuz it is sooo true. lol

  18. Well I love women, yall are some of the most thought putting into-ess creatures on Earth when it comes to sex. Just got with the flow! And if said flow should happen to route through the thighs of another women, then let it be. All this pre-planning planning and re-planning has got to stop.

    Know how men plan sex? We dont….

  19. keisha brown says:

    im more surprised there are only under 30 comments on this post..

    i do cosign that you should know the person somewhat. if you aren’t likely to eff a strange man..

  20. TKO-Curly says:

    I think you should watch lesbian porn to learn some tricks.

  21. Pingback: Her | max-logic
  22. Candy says:

    i totally agree with this post, i’ve been dipping in unchartered waters since dec. of last year, she’s a really good friend, i’ve known her since i was 8, we haven’t been physical yet, she is the only female i’m attracted to, but she has a girl 🙁

  23. I really like what you guys are usually up too.
    This kind of clever work and reporting! Keep up the great works guys I’ve
    included you guys to our blogroll.

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