26 Apr

I was clearing out some of the spam that likes to find its way to my blog and, here lately, it’s spam about shemales – and specifically Brazilian shemales this time around.  And I thought, “Wow… shemales are so confusing to the senses!”  Then I thought, “Hmm, I’ve seen some in porn flicks… and they tend to be some really ugly ‘women’…”

Then I had to acknowledge the thought that, yeah, I’ve seen some shemales who were knock-dead gorgeous, their transformation so well done that you can’t see the man in their face.  The thoughts kept going, taking in my singular experience with a shemale… but I also thought about reading on swinging forums that there are a few straight men (or so their profile says) that wouldn’t mind being in bed with a shemale – and I’ve even read where a few women have uttered the same sentiment.  A question that I’ve asked before just pops into my head:  Why would a straight man want to bed a shemale?

Another question – why do these fucking spammers keep spamming me with shemales?  Huh?

This really isn’t a “discussion” about gender, gender assignment, or any of these rather controversial gender-related subjects.  These shemales are who they want to be and for whatever reason made sense to them.  I know – from my experience and from watching shemale videos, that no matter how much makeup they have on or how nice their tits are, you’re still having sex with a guy since the shemales I’ve seen have opted to keep their junk.  I’ve seen some shemales on ‘film’ with nice, big dicks, just as I’ve seen some where – and I’m guessing – their hormone treatments have started to make their dick shrivel and whither and, oh, yeah, is there some rule that says if you’re a shemale, your dick has to be uncut?  I can’t seem to recall if I’ve ever seen a shemale with a cut cock but I assume that there are some – they’re just not making porn.

We talk about unicorns when it comes to sex and sexuality but it’s my belief that the shemale is the real unicorn, partially male, partially female, and shrouded in mystery.  I know what it’s like to fix your eyes on one and see the woman that they are… and then get that… jolt – of disbelief to discover that girlfriend has a nice-sized dick – her’s was cut, by the way, just in case you wanted to know.  I’ve even admit – again – that her rack was nice; I guess in her mind, anything more than a mouthful is a waste – I like tits and, damned right, if they’re big, that’s just more titty for me to play with.  I know it took me a while after the sex was done (and it was good) to sort the whole thing out in my head, feeling a little ticked off with myself because I got so totally fooled by what I initially saw but also trying to suss out why sex with this shemale felt so… different.  All during the initial foreplay, jeez, my mind kept saying, “This is a woman…” even though I could feel her cock pressing against me as we rubbed our bodies together.  When we sucked each other, it was a familiar thing… but not really and, no, I have no fucking idea why I felt the way I did at that moment.

After putting on a condom, I slid into her; one part of my brain said, yup, this is a man’s ass you’re feeding dick to while another part said, wow, she… he… what-the-fuck-ever is reacting just as a woman would.  It was a visual rush… or clusterfuck… I don’t know which… to look down and see my cock moving in and out of her…, um, his ass… while there’s this nice erection just begging for more attention.  Oddly enough, this was the very first time I ever did a reach-around and I’m not so sure how I managed to pull it off – it takes some interesting coordination – but with my hand on his… er, her cock and my dick in her…, shit…, ass, she came with a rush of sperm – I clearly remember the rather big puddle on the sheets and I even felt as if I had somehow cheated myself because we had elected to fuck rather than to suck each other off.

The nice thing about that encounter was her taking the time to talk to me and, no, it didn’t help that she found my reaction funny – and it was funny but, of course, I couldn’t see the humor in it at that time.  She explained to me that from the beginning, she always wanted to be a woman… but not completely so and, honestly, it didn’t make sense to me… but it kinda did; I mean, why else would a man want to be a woman from the waist up if they didn’t believe that this is the way they were meant to be?  It took me a whole lot of years to understand why I reacted the way I did – how I got fooled by both my eyes and my senses – because while I saw some shemales after my encounter – didn’t have sex with any of them – they were giving off a male vibe despite their appearance… but the shemale I had sex with gave off a female vibe that when along with what I was looking until, of course, she got naked for me.

Feminine… yet masculine all in one package.  This shemale was, in fact, bisexual, something that became apparent when her girlfriend came home and she was kind enough to show me that, yep, she was a 100%, naturally born woman… and if you’re really wondering, yes, the shemale and I both had sex with her, making this the weirdest threesome I’ve ever participated in.  I went home with all of this running around in my head… and it fucked with me so much I wound up with my face in the toilet bowl throwing up everything I owned – that’s pretty fucking embarrassing, by the way, because I have no real explanation as to why that happened.

But that was then, this is now.  I cannot honestly say that I’d never go to bed with another shemale but doing it again ain’t exactly at the top of my list of things to do.  In a lot of shemales, I can see and even feel the man that they used to be and, to be honest, they’re not all that appealing to look at even if they’re packing a lot of meat… or meat period.  I understand a lot better today than I did in my first, real exposure… but I still find shemales a little disturbing at a subliminal level and, yeah, I could be letting my bias show because if I’m gonna have sex with a man, my sensibilities would like it better if he looked like a man as well – just one of my personality quirks that doesn’t imply any real prejudice against shemales; hell, since I had sex with one, how could I be prejudiced without being a hypocrite?

Aw, fuck… time to find something else to write about…


Posted by on 26 April 2014 in Life, Living and Loving


Tags: , ,

18 responses to “Shemales

  1. ellendolfan

    26 April 2014 at 14:18

    Wow. You’ve certainly had some interesting experiences.


    • kdaddy23

      26 April 2014 at 14:21

      Haven’t I? And they’ve been so educational, not only about sex and sexuality but also where my head is about such things.

      Hmm, I might write something about that later…


      • ellendolfan

        27 April 2014 at 20:16

        My experiences have been pretty tame, mostly. I didn’t even officially lose my virginity until I was 23. I now wonder how much of that has to do with that fact that I’m bi.


      • kdaddy23

        27 April 2014 at 20:23

        Perhaps it didn’t. Then again, that would depend on your use of the word “officially,” huh? Seriously, I was under the impression that folks raised under strict religious upbringings often lose their virginity later than most…


      • ellendolfan

        27 April 2014 at 20:28

        Well, if you’re talking breaking the hymen, that happened while masturbating at about 11. Gave my first BJ at 19, but actual intercourse at 23. So it depends on what you call losing your virginity.
        And my religious upbringing did have a big part in why I waited so long. I wanted to wait until I was married. But the fact I had a stalker made me decide to go ahead, and lose it with someone I liked instead of being raped.


      • kdaddy23

        27 April 2014 at 20:40

        Nah, I don’t count broken hymens because I know girls can lose them in non sexual ways… Or they take care of it themselves. Some say that having oral sex is losing one’s virginity but I don’t agree – a girl can still be unknown to a man but have other experiences.

        Stalkers suck!

        But a question I would ask is how many times did you pass on having an experience with a girl and why? See, where I grew up – and when since we seem to be about the same age, having same-sex experiences wasn’t all that unusual; it was like ‘everyone’ was doing it, rich, poor, black, white – none that mattered. But taking that heady risk to do something you knew you could get into deep shit for doing? Kinda/almost like saying how could you not give it a shot or two?

        I was kinda shocked to learn that there actually kids who never did – that’s how. Or all it seemed to me back then.


      • ellendolfan

        27 April 2014 at 20:43

        I never had a chance to experience being with a girl. I am extremely shy and introverted. I didn’t socialize at all in school. And I went to a Christian college, so it was never an option there.
        And keep in mind, that it was only recently that I even realized I was bisexual.


      • kdaddy23

        27 April 2014 at 20:51

        Understood… And utterly fascinating. In my ‘hood, the girls who were experimenting, for lack of an accurate word, would often entice the shy girls into giving it a try. Nothing forceful that I knew of but they were VERY convincing.


      • ellendolfan

        27 April 2014 at 20:56

        I could have had sex with any number of males. I’ve never had a lack of opportunities there. But I never did have a chance with a female. If any female was ever interested in me, I never knew it.


      • kdaddy23

        27 April 2014 at 21:13

        It’s so nice talking to you about this. You really don’t hear a lot from women about being bi… And maybe it’s because women don’t see it as that big of a deal or our society is just used to assuming that all women have done it at least once – and then in college!


      • ellendolfan

        27 April 2014 at 21:20

        I honestly wonder how different my life would have been if I had gone to a regular college, and had experimented. But then, I was still shy & introverted in college too.


      • kdaddy23

        27 April 2014 at 21:28

        Honestly? I believe you but you really don’t sound all that shy to me!


      • ellendolfan

        27 April 2014 at 22:19

        It’s easy to talk to people on here. In person, I freeze up and can barely get a word out. I used to work as a waitress, and I could talk to people because I had to. But I couldn’t go to a club, and make small talk. Being somewhat anonymous online is very freeing.


      • kdaddy23

        27 April 2014 at 22:24

        Yes, indeed, it can be rather liberating. You and I have been having some great dialogs and I do appreciate your candor and apparent openness – thank you!


      • ellendolfan

        28 April 2014 at 00:21

        You have some very interesting posts. Lol, I sent my friend a link to your blog. Her comment was, “I’d pay him to do me”


      • kdaddy23

        28 April 2014 at 00:27

        Tell her I’d do her just because it would be fun – because it’s all supposed to be fun!


  2. larryarcher

    27 April 2014 at 00:17

    Wifey once had a girlfriend (boyfriend?) who she met at a bikini contest at a local bar. Funny the owners never knew that a guy had won the bikini contest. It was interesting to go out with them but I never quite figured out how to deal with her but she was cute.


    • kdaddy23

      27 April 2014 at 09:47

      I know; do you treat her like a lady… or like one of the fellas? I can remember a couple of funny stories involving shemales and people I know, like my late brother (and his friends) and my step-daughter’s boyfriend…



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