worst. sex. ever.

I don’t usually kiss and tell.  Well, actually, I do kiss and tell, but I don’t usually have sex and tell.  Unless it’s bad.  And then I spill the beans.

A friend reminded me recently of the story of my worst sex ever.  It’s  a story that he remembers because… well… everyone who’s heard it remembers it.

First, let me be clear that a guy has to be an over-achiever to claim the title of worst sex I’ve ever had.  I’ve had a lot of sex.  Some of it was worthy of whatever the Oscar for porn is, and some of it was just plain bad.

Before my marriage, my award for worst sex ever belonged to a really nice guy with a really small penis.  Now, I’m honestly curious what kind of karmic debt he’d incurred to force him to go through this life with such a remarkably small penis, but it was truly so small that I didn’t even realize when intercourse had actually begun.  This dubious distinction won him the cruel nickname of “Phantom Dick” from one of my girl friends.  (And, I’m not a size snob; in fact, I am biologically constructed in such a way that a guy has to be pretty darn tiny to not satisfy my size criteria….) But, anyway, Phantom Dick was so nice and smart and sweet that I was relieved when our relationship fell apart for other reasons, so I wouldn’t have to suffer the guilt of breaking up with a guy simply because nature had played a mean joke on him.

Twenty years later I realized that there are far worse things than phantom dicks.

The lover who currently holds my worst sex ever title we’ll call John, because… well, because that’s his name.  I dated John not too long after my separation.  By the time John and I took our clothes off, he had had a crush on me for several months and had been angling for just such an opportunity.  So, the sexual tension was high and the anticipation was thick.

The foreplay wasn’t awful.  It was, however, what I like to call “Checklist Foreplay.”  (Every woman over the age of 30 is nodding her head right now and going “Ohhh…. bummer.”)  Checklist Foreplay, for you young women and male readers, is when a guy seems to move through the motions simply because he knows he’s supposed to.  It goes something like this:

  1. Kiss mouth.  Check.
  2. Kiss neck.  Check.
  3. Fondle breasts.  Check.
  4. Kiss breasts. Check.
  5. etc, etc.  You get the idea, right?

Here’s a good rule, guys:  If you don’t enjoy doing something, don’t do it.  Sure, we’d probably rather that you did, but doing it without any enthusiasm is worse than not doing it at all.  I don’t do things in bed that I don’t like to do.  (Okay, in fairness, I’m not sure what those things might be, but if I find one, I swear I’m not going to do it.)

John tried to be sweet, paying me compliments.  Some hit the mark — “You have the body of a 25-year-old!” — while others did not — “Nice boobies!”  Ahem.  Another good rule of thumb, guys:  When in bed with a woman, don’t ever, ever refer to her body part by a name that her sexually-repressed grandmother might have used.  Go for a porn-worthy reference, or stick with the clinical term.  But don’t call our parts by cutesy names.  It’s not sexy.  It’s just icky.  If you doubt me on this, imagine how you’d feel if we said to you, “You’ve got a great pee-pee.”  Seriously.  Just don’t do it.

After the toe-curling pleasure of our 5-minute foreplay (not), it was off to the races.  I felt certain that things would improve once we really got rolling.  After all, this was a good-looking guy whom I knew to have no trouble seducing women and more than enough notches in his bedpost to suggest the development of serious artistry in the sex department.  So maybe foreplay wasn’t his thing.  It was bound to get better, right?

Umm.  No.

Because there are hardly words for what happened next.  Basically, he moved his car into the space, and threw it into park. And there it sat, idling.

At first, I was confused.  I looked at his face.  His eyes were closed and he had the look of someone thinking hard about something.  Okay, I thought, maybe I just need to do some of the work here.  But that wasn’t even possible — he was nearly 6 feet tall and about 190 lbs.  I could barely move my arms, let alone my hips.  Not that it really mattered, because, as I was contemplating how to manipulate my body, he sighed and pulled out of the parking place.  Job completed.

Then he smiled at me and said lots of sweet things and I got the hell out of there as fast as I could.

On the drive home, I was not only sexually frustrated but absolutely flabbergasted.   I mulled over any and all explanations for what had just happened.  Perhaps he was drunk and having to struggle to keep the car running?  Or maybe he was just so overwhelmed at the opportunity to have sex with me that the engine got too revved up too quickly? (I liked this explanation, personally.)  Or maybe this was some Kama Sutra thing that I’d have appreciated if I’d ever been disciplined enough to read the book instead of only look at the pictures?

Well, because I am a glutton for punishment very nice person, I gave John a second chance and confirmed that, whatever the reason, this was his personal style of sex.  To his credit, the second time lasted slightly longer; long enough, in fact, for me to remember that I’d forgotten to take the chicken out of the freezer for the next night’s dinner.  Now, I’ve had sex that literally made me dizzy and nearly pass out, so if you’ve got me thinking about frozen chicken while you’re supposedly making love to me, our relationship is not long for this world.

So, before we go on, let’s review for our male audience what we’ve learned:

  1. No Checklist Foreplay.  Unless the checklist consists of “Ravish her body passionately,” it’s just uncool and a buzzkill.
  2. No cutesy names for our female parts.  Not unless you want us to turn you on with references to your “pee-pee” and your “bum-bum.”
  3. Friction — actually, movement generally  — is a necessary element for intercourse.   Whatever you do, don’t park the car before taking it around the block a few times, please.

As it turned out, there were ample reasons that John and I did not belong together that are far more important than his claim as my worst sex ever.  But he still holds the title.

And, if there is a God in heaven, he always will.


Filed under dating, relationships, sex

40 responses to “worst. sex. ever.

  1. I see Seamus has inspired another post but, fortunately, is not the ‘star’ of the post. 🙂

    Despite already knowing this story, I cannot help but add: WHAT?!!

    • Yep, that Seamus always gets me thinking. 😉

      I know… I know… it still sounds as bad to me as the first time I told it to Annie. Ugh.

      • I see we have both been tagged for a blogger award tonight. It’s a shame there isn’t one where the goal is to detail one’s worst sex experience ever instead of answering nice & interesting questions. I suspect that, as bad as yours is, some people have had even worse experiences. My own worst one comes close, for example, even of it was a one-off (Seriously? You tried TWICE? OMG).

        • Well, I think that there are probably different categories for straight men and women, as you can’t possible appreciate mine and I’m pretty sure I couldn’t appreciate yours. 🙂

          Yes, twice. What can I say… I like to be certain…. Sigh.

  2. mysterycoach


    Wait. This here: “You’ve got a great pee-pee.”

    HAAAAAAAAAHAHAHAHAHA!!!! omg Thank you! Thank you SO MUCH for this post it’s hilarious!

  3. Pingback: Worst. Sex. Ever. « MysteryCoach

  4. I have heard entirely too many horror stories from women similar to yours. It is for that reason that I write my blog which actually has more posts telling men to do it better and showing them how and why.
    John Wilder

    • Androgoth

      Well said that man…

      Now go forth and… Well you know? 🙂
      It is not every day that one happens
      upon an expert, or is that sexpert? 🙂 lol


  5. Aaaaannnnndddddd…………. I just woke the kids up with my laughing- at the other end of the house. Darn, that’s funny. I especially like the “What about my feelers?” I’m gonna be laughing about that one for a while…… SO sorry for your suffering, though. 😀

  6. I made the horrible mistake, not that it killed the moment for him (and I do mean MOMENT) of asking “Are you in yet?”

    • {snarf!!!} {cough cough} I think the better question is: has anyone NOT done that? 😆

      • You mean I’m not the only one? Thank God! I hope I am the only one that asked hIm that, I can see it might have a negative effect on a man’s ego.

        But even as I was typing that I thought of another fellow I dated for over a year who was not well endowed and yet he was a wonderful lover and I never felt “short changed” as it were. I’ve been with men that seem to figure that they get out of participating in the act as long as they arrive with a big penis. Wrong!

        • OMG I just thought of someone I haven’t thought of in years!!! He was a gorgeous hunk of man; a rambo look alike and a lot younger than me. I was 1 1/2 out of my first marriage and ready to date (horny) we went out a couple of times and had absolutely nothing in common except we both thought he was extremely sexy. We got into bed and he literally laid on his back, put his hands under his head, and waiting for me to hop on. Rotflmao I’ve had vibrators I felt more connected with. It was a one night stand.

        • mysterycoach

          WAIT! I have to add this here… I remember there was a person I was friends with in a way and we ended up dating. So, he boasted about longevity and all that stuff. I learned one should not boast … We fooled around and I figured, since he was “so open minded” when we were done I suggested this book I had at the time (I was about 27). He said, “What’s it about” I said, “Sex”.

          I don’t know WHY he was offended yet… staring at the ceiling bored out of my mind was… it was like, how do I say this? It was like… comparable to the motion of sawing wood. Oh look, my eyebrows are furrowed together remembering it. ugh… shame.

          They say we can learn new things and I believe that to an extent but some things, are not learnable I don’t think.

      • mysterycoach

        “snarf!” ROFL ! hahaha!

  7. Androgoth

    Yes he sounds rather dull in every respect, still there
    has to be some that under achieve, but what a poor lover
    you had there my friend 😦

    Never mind there is always an opportunity
    to indulge in something more exquisite…

    Just not with him right? 😦

    I have called in here this evening
    from my friend’s Space… Mystery Coach


    • Welcome to my little corner of the internet. 🙂 Thanks for visiting.

      Yes, he was more than mildly disappointing, but given that he also turned out to be manipulative and two-faced, I can at least write about it without a sliver of guilt! 😀

      • mysterycoach

        I have to do a post about guilt… I really do. Because … I just do! 🙂

        Euw Precious, he’s icky. We all know how much I love a manipulative person now don’t we? eeeuuuwwwww… gross! (snort’s in disgust, you know, like a dog who sneezes? LOL!)

    • mysterycoach

      Da meeeee!!!! LOL hahaha! 🙂

  8. Well at least the car got into the garage, even if it was just for a second 🙂

  9. He did what one of my friends called “the one thrust” or OT for short.

    He was an OTer.

  10. thresea

    it can’t always be the man’s fault sometimes sista you gotta own that action. You fail over and over life I’ve read before.

  11. feeling stupid

    You’ve got a nice pee pee – I’m crying from laughter and now hooked on your blog.

    I’ve been with one man sexually (and I’m an old hag) but curious what’s good sex like. If that checklist foreplay isn’t good, what’s good, describe it to me (I want to live vicariously through this wonderful sex you speak of).

    also when you say he could have gone around the block a few times, does anyone care to elaborate, what else can he do with his penis.

    My ex used to stick it in me and start jackhammering for 2 minutes. I received that once every month for 20 years and I was starved for even more of it thinking that was good enough to get me to masturbate once he got off me.

    Im curious what love making is like and how do i find one of those men. I’m in my late 30’s now and look after myself but I have no idea how to find one of those good love makers.

    • I’ve been thinking about an appropriate reply to your question about what is good sex, and what I’ve come to is that there is no good answer, unfortunately. I think this is because “good sex” is basically whatever you do together when you are in sync. In other words, if you both feel like a passionate quickie and that’s what you do, it can be immensely satisfying. Or, if you both feel like long foreplay where you trade off doing various things until you feel like you’re about to explode, and that’s what you do together, that can be remarkable. But really, it’s usually about being in sync. Liking the same kinds of things sexually and having the intangible chemistry that makes you want this person over and over and OVER again.

      I think that men who are generally quick “jackhammers” (I love that term you used) don’t get high reviews from most women. Feeling like a sexual receptacle is not very sexy or satisfying. While quickies are certainly fine, if that’s the only thing on the menu, it gets old VERY fast (as you well know).

      Some women prefer sex that is raunchy and rough, while others are totally turned off by that. Some prefer slow, romantic love-making, while others find that a yawn. The main thing is figuring out what you want and finding someone who is game to do it.

      Which brings me to communication: the main ingredient for good sex, beyond the intangible chemistry, is the ability to communicate during sex and outside the bedroom about sex. And I don’t just mean complaints and suggestions, but sharing new ideas. If you can’t do that, no matter how good it is at the beginning, it’s going to get old and boring later.

      As for how you find this… this was the part that gave me the most hesitancy… because I don’t want to encourage rampant promiscuity (because, trust me, you won’t feel good about it later) or put you at risk for an STD or worse, but the real answer is that you have to figure it out through trial and error. Watch some porn, maybe, and see what turns you on. Find a friend with benefits who is willing to be playful and let you figure things out (you don’t need to tell him you’re doing this, it should come naturally). Or just start dating and when you find a man to whom you are a) seriously attracted to physically, emotionally, AND with a clear head, and b) able to talk to easily — then give it a go and tell yourself that you’re “practicing.” Speak up with what you’d like and if he responds poorly, move on.

      Most men your age and older are mature enough that they love a woman who is trying to be fun and curious in bed. That is never a bad thing. They are much more interested in women who are open and curious than sleeping with a Barbie doll who has all the moves mastered. Trust me, I’ve heard this over and over from men. Be yourself, be honest, and just figure out what you enjoy, and your guy will love taking that journey with you. 🙂

      Finally, when I said that it would have been nice for him to drive around the block a few times, I was referring to foreplay. Touching, licking, kissing — both him and me — before heading straight to vaginal intercourse. Because the situation was not one in which passion overcame us and began ripping each other’s clothes off and just leaped at each other (which can be fun, too!), I was surprised that there was no real foreplay. He literally seemed to be just touching things to get it over with and move on the main course. It felt very perfunctory.

      That man is actually a good example of my first point that good sex is VERY subjective. He had slept with scores of women, and so perhaps had developed a playbook that worked with some percentage of them. But it didn’t work for me. And what works for me doesn’t have to work for you.

      Go figure it out and have fun! 🙂

    • Is my math off? You got that for over 20 years but you are in your late 30s??

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