The twentieth question for the Q&A section of this blog is: “What was your most disappointing sexual experience?”

Well, now we’re officially into the questions that are hard to answer for more reasons than just that they take a lot of thought.  I’m wary about answering this, because obviously it involves people other than just myself in a very personal way, but I committed to this, so I guess I’ve got to do it.  Be warned, this post will be INCREDIBLY TMI and NOT SAFE FOR WORK, so if you’re not comfortable with sexual themes, or knowing things about my sexual history in particular, PLEASE DO NOT READ ON (but if you think you can handle it, click the link below).



When I first saw this question, I decided that I was going to just go with a general answer, but now that I’m actually writing it, I think I’ll start with a general answer, and then narrow it down to one experience after that, instead.  So in general, my most disappointing sexual experiences have always (as far as I can remember, at least) involved condoms.  I’ll be honest; I hate condoms.  I certainly think they’re important, and in most cases necessary, especially since I definitely don’t want STDs or to get pregnant (though when I did get pregnant, we were using a condom – as one of *three* methods of birth control that somehow all failed), but that doesn’t mean I have to like them.  I find them to be mood killers; when I’m in a passionate moment with someone, and it’s progressing toward sex, I don’t want to be fiddling around trying to open a condom package.  It breaks the build-up for me, and I often feel like I have to start all over, and you can’t really start over well with a condom on for multiple reasons.

Condoms are like this guy.

Condoms are like this guy.

On top of that, I have a latex allergy, so sex with a condom is actually painful for me…sometimes during the act of sex, and sometimes (if I’m “lucky”) after.  It’s very unpleasant, and makes sex far less attractive than it rightly should be.  It’s hard to have a healthy sex drive when you know that sex will bring pain, sometimes for a long time (depending on the brand).

I’ve also known a fair amount of guys (both guys I’ve been with and just friends I know well enough to talk about this stuff) who have a hard time feeling as much pleasure with a condom on as they do without, or who sometimes can’t feel anything at all with a condom on.  Now, I know that a lot of guys just say that is the case, but it’s also a legitimate problem for some guys too, and that much I can confirm by knowing people with that problem who would have no reason to lie to me about it because they’re not sleeping with me, and because I’ve actually seen a guy cry before because he didn’t know what to do about the problem, and his girlfriend (like me) could not take birth control due to the side effects.

So, I hate condoms.  When condoms have been involved, I’ve generally enjoyed the sex less, because it led to pain for me, and in some cases, loss of sensation for the guys, and for me, when it comes to sex…I’m all about the guy I’m with getting pleasure.  I could not possibly care less if I don’t orgasm, but if he doesn’t, that’s a huge problem for me.

houston we have a problem

And there’s the general answer.  On to the specific example!  I’ll try to make this quick, since this post is long and TMI enough already.

So the most disappointing sexual experience I’ve had that I can easily bring to mind was the first time I had sex with one of my previous boyfriends. He had not had sex in over two years, due to being with a girl for the duration of that time who was “afraid” of sex, so when we got to the stage where that seemed to be a possibility, there was quite a lot of anticipation on his part about it.  We’d been intimate in other ways up to that point, so we had no reason to think sex between the two of us would be unsuccessful, but when we tried, it…didn’t go as well as we’d hoped it would.

Basically, a condom was involved, and he’s one of those who has decreased sensitivity with a condom on, but he didn’t actually know that, because before me, he’d only had sex with one girl, one time, and it was so sudden that they didn’t use a condom.  On top of that, being with a girl for two years who wouldn’t sleep with him but would sexually tease him had led to him masturbating a lot (like, multiple times a day a lot), so he’d unknowingly made it pretty damn hard for a girl to compare to the type of grip he could achieve, and he was also quite nervous, because it was his first time having sex without being drunk.  So there were a few factors working against us, but at the time, I only knew about one of them – the condom.


So our attempt at sex, that time, ended up without him finishing, which led to frustration and upset for both of us, and at the time we weren’t sure why it had happened.  But after a lot of talking, we sorted out a ‘game plan’ for next time, and, well…best sex I ever had, after that, and he never had a problem with finishing again.  That night was tough, though, on both of us.  A pretty hard hit to the self-esteem.  And that’s why it was disappointing!

Now that I’ve thoroughly grossed/weirded everyone out, I’ll end this.  See you next time for a much less TMI question. 😉

Check out Mike’s answer at, and please feel free to post your own in the comments! :)

(Next question: “What is the strongest opinion you hold?”)