Revisiting In Through the Out Door


I’m uninspired this week so we’re throwing it back to one of the first Nasty Friday posts. Enjoy and I’ll have something fresh for you next week.

When I was young, oral sex was the thing no one admitted to. No self-respecting Black man would admit to ever eating a woman’s fruit – much less beg her to let him do it. And no good girl was going down because, of course, that’s nasty. These days oral is a no-brainer, or it should be anyway. To the point where I’m some women are getting bored of it. It’s too mainstream now. There’s a new player in the sexual liberation game and its name is anal.

It seems the world of women is separated into three groups – the have’s, the haven’ts and the would-nevers. Those who have have earned the right to feel smug and superior to those women who haven’t or won’t – by allowing their exit to become entry they have forever secured their spot in the world of the sexually uninhibited; no matter what else they will or won’t do. The would-nevers are probably smug in their “good girl” status. It’s nasty and they don’t do that so go find some hoe off the street if that’s what you’re looking for.

The haven’ts are gnashing their teeth trying to figure out where they fit in…they haven’t, but does that mean they wouldn’t? Is it something to squander on a night of drunken after-club sex when you can blame it on the alcohol? Or something to be saved for that mythical magical one – the husband, the soul mate, the only man who has ever been up the bum?

These are the things I ask myself sometimes.

I have a lot of dirty male friends. And for whatever reason, we talk about anal sex a lot. No matter how many times we discuss it, I can never get over the fact that sometimes a girl will let a guy go up the bum the first time she fucks him. Really?? Just all willy-nilly like that? But at the same time, I turn up my nose scornfully when I hear stories about women who are like “never! I would never! Just – ew!”. Amateurs.

My mindset lies somewhere in between. I’m not giving up my primo virgin um, territory to just any random that comes along (it’s the last piece of innocence I have left and I’m clinging to it for all it’s worth). But at the same time, I’m certainly not saving it for a husband who may never materialize. There has to be a middle ground and so I’ve compiled a list for you of the Top 5 Characteristics of the Ideal Ass-Taker.

1. The ideal taker of the ass-virginity is somewhere between a random and a soul mate.

I don’t want to give up the ass to someone who will later break my heart so that for the rest of my life I have to say “and I gave him my VIRGIN BUM!”. But at the same time, I don’t want to give it to some random who probably collects asses like playing cards. It has to mean something to him.

2. The ideal ass-conqueror has to be persistent, but not pushy.

I’m probably not going to say yes the first time around, but I’ll probably give in somewhere between ask #3 and ask #74. So he can’t give up, but he has to know when to ask.

3. The ass-explorer must be gentle.

If you go tearing through my shit (pardon the pun) all roughshod I will stab you in the eye. While I’m all for a little rough-and-tumble at other times, this is one time where I want you to go all Brian McKnight on me.

5. The ass-breaker cannot be too well-endowed.

My 8-inch plus guys are going to have to step to the back of the line on this one. Sorry guys, you know how much I love you but I can’t use you for this one. Where are my 1 and 2 inch willies? I have a job for you!

5. The ass-winner must be discreet.

First of all, word on the street is that there can be some um, mess involved with this job. I need you to handle that on your own without mentioning it to me. I’m no would-never, but that’s nasty and I don’t want to know about it. And secondly, if you go to the sports bar with your friends talking about how you took Max’s ass last night I will, again, have to stab you in the eye. Discretion is the better part of ass-fucking my friends.

Now Fridays are for over-sharing so I want to hear from you on this one. Ladies – are you a have, haven’t, or a would-never? Men – what say you on these requirements? Am I asking too much?

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 37

  1. CHeeKZ Money says:

    ‘5. The ass-breaker cannot be too well-endowed.’

    wouldn’t u be more concern with girth than length?

    If there is one thing I missed about finding new pu$$y dating is that there were specific things that of the girls I slept with I never got the chance to experience.
    So I never really found a girl that will LET ME GO HAM in the back door. So when my friend tells me ‘I found a girl and that is all that she is into. I think its gross’ I really want to punch them in the face and steal that jumpoff.

    That. An 0rgy. And a Squirter… and I’m ready to retire.

    1. emti says:

      I think Cheekz should do a guest post on squirting

      1. CHeeKZ Money says:

        I think Emti needs to let me do a guest pludging in her snatch.

        1. emti says:

          only if you can make me squirt

    2. Sukez says:

      That’s always fun.

      But girth is what would make it hard to get into. Length would make it hard to continue. If that made sense…

      1. B_P says:

        Perfect sense. My name is BP and I wholeheartedly approve and agree with this message.

        1. CHeeKZ Money says:

          BP. Sukez.

          Give yourself I pat on your back
          I fee like I know so much more about what wifey is going thru (pause).
          Who knows how many countless marriages you have saved

          **tips caps**

        2. Sukez says:

          BP haha. Booty Pleasures. haaa

          1. B_P says:

            Lol, LOL, LOL! HotDamn I love you Sukez!

  2. melissa says:

    i forgot what i commented the first time around, but i suspect it’s the same as this. i’m a “have” and i’m a “like it”.

    all your requirements are right on point although i think that #4 (5a?) can be worked with as long as he’s gentle. the key is to push back at your own pace rather have him thrust. then once you get it going, it’s all good and he can pick it up. 😛

    1. emti says:

      OMG why do i never remember not to visit this blog on Fridays
      my virgin eyes

      1. melissa says:

        lol….virgin eyes my (pun intended) ass.

  3. Nick@Nite says:

    I’m a “have.”
    I was in a long-term relationship so I knew who I was working with. I don’t even remember how it happened. But I DO remember there being no lube, so lotion was involved. Yeah, I won’t do that again.
    I don’t really like the “would-nevers” not just in sex, but in life. I think most of the time, I want to try so that my opinion of something is based on actual experience. So that I know what I speak of.
    Frankly put, if the vibe is right, I’ll endulge in a lot of things. That “vibe” is the death of me most of the time.

    1. Dash says:

      “But I DO remember there being no lube, so lotion was involved. Yeah, I won’t do that again.”

      I LOLed. If he was a anal regular, he should have had kept some KY on his key chain.

  4. Dash says:

    I can’t see myself ever giving up my booty virginity/Manhood.

  5. emti says:

    i will call myself a haven’t while right now i can’t see myself doing it
    i never say never

  6. I very rarely get real on the internet, but I will do this here because this is a different spot I like to hit every now and then…

    @Cheekz – Squirters are everywhere. You can make just about any girl squirt. Hint: Pressure busts pipes. Now i’ve met a fire hydrant and I have to say, ain’t nothing like opening a fire hydrant in the middle of the summer.

    In terms of “I know you missing that anal…” I think that it’s funny that a girl will slip a finger in there when she’s tooting the cooter, or maybe that she likes a little pressure there because it makes her wetter, but she won’t just take it like a pro. I can give you the quick and dirty tutorial; LUBE, finger, thumb, penis, just in, slow pump, plow…

    There is nothing like a girl who says, “I want someone to f*ck me in the ass”. Now that turns a guy on. But he’s also wondering if you just let anyone in the backdoor… I know I am. But the ladylike way to say it is, “I’m not opposed to anal play, as long as I get some warning.”

    Some say it’s nasty, but… the first girl to introduce me to it was a freaky nurse student who was always quiet and unsuspecting. You have to watch out for the nurses… Shorty came over with a plug in her butt one time. She didn’t just like anal play, she liked anal plundering…

    1. CHeeKZ Money says:

      you know how much reseach I have done over the years on this topic homey.
      I bought books. Watch tutorials.

      Doesn’t change the fact that a)some girls don’t do it b)people have different levels of pain resistance. She can’t STAND that ‘pressure’ fingering.


      Butt plugs player? So you insult my chexual intellect than you mock my monogamous relationship by bring up the fact that you are just THE KING of rectum play. Butt plugs. Thought we were e-pals.

  7. never done it. not opposed to it actually. look forward to trying it one day. want to see what all the hype is about.

      1. that’s what they say.

        1. Sukez says:

          Tis true. WeThey don’t lie.

      2. CHeeKZ Money says:

        better target positioning.

        More st8 forward instead of underneath. cleaner motion in your stroke.

        1. Sukez says:

          I’m getting excited.

  8. Funms says:

    I have never tried it but maybe i will someday……if i find the right person and size

  9. Sukez says:

    I hate that all of a sudden, you’re good with numbering after 2 but before 5!! >_< But I love your blog and your highly inappropriate thoughts.

    Anywho, I’m a HAVE. *does uninhibited dance in circles* <(^_^<)(>^_^)>

    I agree with #1 thru double #5. My ass-virginity taker was someone I loved. But he wasn’t persistent or pushy (#2). One day we talked, I brought the baby oil, he slid in. And gently (#3) and gently he stroked..forever.. Until I couldn’t take it anymore. Well endowed? Shit! What was I thinking?! He was huge 🙁 Probably why I like it so much now from any size (#5).. As long as they’re gentle. As far as the “mess” or details, he never talked about it except it was about how wants to do it again, and that was to me. (#5)

    Will I revisit my 1st tightest hole? With pleasure, literally. But first with ease. He even licked my bum. O_O Now that is a feeling!

    1. max says:

      Nothing beats a rim job. Nothing!

      1. Sukez says:

        I always called it rim shot. Lol sounds like basketball. But rim job makes me giggle when I see it.

  10. I have, and i rather enjoyed it. My first wouldn’t do me right b/c he didn’t want to hurt me. My next put his back into it, though. lol. I told one of my friends that I wanted to see if I could take him, b/c his girth is ridiculous. He has a gf now, so I never got a chance to test it out. One of the biggest regrets of my life…

    1. CHeeKZ Money says:


      We are not worthy. We are not worthy.

  11. Sukez says:

    Getting back into it after 2 years of NOT getting it back into me, it did feel weird cuz it ended up feeling so good. Like Nia, I want to try a healthy girthy mo-fo. The thought of blood and ripped skin is making my hair stand on end and my eyes light up.

    1. blood dan ripped skin doesn’t make my eyes light up. not at all. lol. But, the idea of being able to take him whole does make me feel a little warm and tingly.

      1. Sukez says:

        Oh best believe the warm feeling washes over me on a regular basis cuz I can’t get booty pleasures off my mind. I’m warm right now. Tingly forever more.

  12. fixedwater says:

    I have, and ehh it gives me gas so now I say no thanks. and it was with my the love of my life from whom ive moved on from.

  13. Jsn says:

    One of many areas I feel it’s better to give than receive

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