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…