I’m sure there aren’t too many adults who don’t know what a ladyboy is so I won’t get too much into spelling it out other than to say that these guys/gals (I’m not sure which) used to be known as transvestites, or TVs, for short. The first time I encountered one, I had to deal with the fact that all of my supposedly reliable senses got totally and completely fooled; I just knew that I was dealing with a really hot chick who wanted to screw and there was no way I was gonna say no… only to get to her place and she gets undressed, revealing not only an appropriately nice rack… but also a cock that was about the same size as my own.
Now, I had previously heard of some dudes running into this exact situation and, well, let’s politely say that severe violence ensued immediately; I even heard of a couple of alpha male type guys who, upon seeing this rather confusing situation, hauled ass as if some demons from hell was chasing them. Me, well, shit… I was there, she was there and, um, okay, we got it on and, gulp, the sex was good beyond belief or, really and honestly, beyond what I believed it could be. As mentioned, I walked away from that encounter totally pissed off with myself because, as I said, all of my senses got fooled because this ladyboy subliminally felt like a woman – holy shit.
I chalked it to up a great lesson learned (and one I wouldn’t want to repeat) and kinda put it out of my mind. Many years later, I was on my favorite swinging site’s forum and got involved in a discussion about she-males, the new word coined that, honestly, sounded and felt better than “transvestite.” What surprised me was the number of straight men who enthusiastically admitted that, damned right, they wouldn’t mind laying the pipe with a she-male although, when I asked them why they’d want to throw down with a chick with a dick, none of them could come up with an answer that made sense to me other than, “That’s just some hot-assed shit!” A few of the straight male participants, when asked if they’d suck a she-male’s cock said that while they would “normally” avoid sucking dick like the plague, sure, they’d suck a she-male’s cock and not think twice about it.
My parting comment, as I left the discussion, was, “What the fuck’s going on here?” Anyway…
One of the things I have really not been able to sort out in my mind is why a guy would want to transform himself into a woman from their head right down to their navel – then stop. I felt that maybe it’s just me but if you’re gonna go through all that stuff to feminize yourself – including undergoing breast implant surgery – why not go all the way? In stuff that I found on the subject, I learned that some guys making this “partial transformation” were willing to do the hormone treatments and the implant surgery… but drew the line at having their dick lopped of; I also learned that some guys felt that being feminized… but keeping their dick… was truly the best of both worlds. Some guys making the change just couldn’t afford the additional surgery that would remove the last vestige of their masculinity.
When transgenderism began to make its appearance and documentation was being published explaining how some people firmly believed that they were born into the wrong gender/body, well, okay; even after reading reams of information – and having a deep conversation with a guy I worked with who became a woman – wow… I had a very hard time wrapping my head around it and mostly because I couldn’t ever imagine myself feeling this way although, I will confess that there was one time earlier in my life when I actually did wonder what it would be like to have female breasts. I thought about it, tried to imagine myself with a nice rack, and shuddered as if I had been dipped in liquid nitrogen; my male psyche vetoed the thought so hard I kinda made myself nauseous.
Last night I was checking out Tumblr to read a comment someone left for one of my blogs posted there but I had to swipe though all those pictures and other stuff to find it – maybe I’m doing something wrong but when I tapped the notification I got on my iPad, it just opened Tumblr but didn’t take me directly to the comment I was looking for – but I’m not gonna sweat that. So… I’m swiping and I guess it was “Ladyboy Night” on Tumblr because I must have swiped past fifty or sixty depictions of ladyboys before I found what I was looking for… and the question that popped into my head was, “Why would a guy with a really nice dick want to be more woman than man – but keep that nice dick?” I mean, damn, in one pic I saw, the ladyboy was sporting what had to be a nine or ten inch cock as well as what looked like B-cup breasts… but when you looked at her face, well, it was masculine; despite all that, um, body work, you could still see the man. But that’s not what really got my attention… it was the comments I stopped to read that kinda had me asking myself, “What the…?”
One comment said – and I’m paraphrasing here – said, “Shit, I’m straight and I’d go to bed with her! She’s hot!” and I thought, “Um, no… not really…” because, as I said, when I looked at her face, I saw a guy and, yeah, as much as I hate to say this, there are some ladyboys who really do make for some “ugly” women. I wondered what made this guy say what he did; was he getting turned on by the ladyboy’s tits… or was it that huge boner that got him all hyped up… or was it all of the above?
Now, not only were there a shitload of comments from men who expressed the desire to become a ladyboy, there was an equal shitload of dudes who fervently expressed the desire to have sex with a ladyboy and there was even a woman who felt that getting fucked by a ladyboy was her idea of fun. I saw one pic that asked, “If you could, would you suck her cock?” I took a look at the cock in question and, yup, the bisexual in me said, “Yeah, that’s quite suckable, alright!” I looked at her tits and thought, “Okay, D-cup chumps…” then looked at her face and thought, “Okay, obviously, she could afford the facial reconstruction surgery to erase all traces of masculinity.” I even wondered for a moment if she was on a regimen of hormone therapy but I didn’t think so because, yeah, that ladyboy had a good-sized cock and I’d read that when a man undergoes those hormone treatments to feminize themselves, their cocks begin to shrink and some to the point that when they get hard, the resulting boner is no longer than my little finger. I went back to her breasts and looked very close at them and, yep, I could just see the scars leftover from her breast implant surgery.
Was this ladyboy hot? I didn’t think so, not that she wasn’t all dolled-up to be very pretty but, nah, I got no sense of hotness… but the twenty or so guys that commented on this pic obviously thought so; they not only said that they’d suck her cock but they were also very willing to have that cock in their own asses – one guy said that he wasn’t into anal sex at all but, yep, he’d let the ladyboy fuck him… and I asked myself, “What would make him do something that he “normally” wouldn’t even think of doing?”
I couldn’t come up with an answer, probable or otherwise. I sat there looking at this particular picture and asked myself exactly what it is about the woman shown that’s driving these guys apeshit and all gung-ho to jump into bed with her when, obviously, if she’s fully a woman, well, that notion is all inside her head and not completely represented physically. Yep, if that rather nice dick was on a guy, I’d suck the shit out of it… but it wasn’t on a guy and I seriously asked myself if, in fact, I wouldn’t go for it because, um, from the navel up, that’s not guy-type equipment. Shit, I even asked myself if I managed to develop a “prejudice” and one I may have acquired in my one and only encounter with a ladyboy.
I didn’t think I had; I believe that I’m grown up enough to accept the fact that if a man wants to partially transform himself into a woman, okay, I really don’t have a problem with that, not like some people do. I thought that, okay, in that one and only time, yeah, that ladyboy had me hard and ready to go two seconds after she asked me, “Can I take you home so you can fuck me?” – and, so, I thought that while I was sitting there looking at this picture and not even close to being visually stimulated by it, I wondered how I’d react if that particular ladyboy was right in front of me so all of my sense would be in play… and I couldn’t answer the question; I couldn’t predict how I might react and that, my friends, is unusual for me.
I don’t try to make sense out of this; it gives me a rather nasty headache so I just accept that, yeah, there are guys who want to be part man, part woman because it suits their purposes to be this way. I accept that they are people who, just like me, have their own lives, their own desires and they do, in fact, have the right to be who and what they wanna be. While I’m currently unable to say that I’d go to bed with a ladyboy – again – I also can’t say that I wouldn’t. I did think, as I closed the Tumblr app – and after finally finding the comment I was looking for – that, okay, I’m bisexual… so what’s the problem with getting busy with someone who, literally, is representing the best of both worlds? I was able to admit to myself that, yep, you do have a slight prejudice; if you have tits, I prefer that there’s a pussy that comes along with them and, if you have a cock, well, you don’t have tits because you’re all man. I shrugged and muttered, “I really don’t know if I’d sleep with a ladyboy again… but I might… but maybe not – I just don’t know…”
My mind started to get into the science of attraction and I shut it down because I could feel the slight beginnings of a headache I sure as hell didn’t want to deal with. My mind changed tactics and tried to get me to think about that subliminal vibe that lends itself to attraction and sexual arousal… and I told my mind to leave me the fuck alone because I was ready to go to bed; it’s not like I’ve never pondered the phenomenon before – I just had no desire to think about it in that moment. Looks, such as they are, ain’t everything – it’s the personality behind the physical appearance that plays heavily into things just as much as it is that subliminal vibe I think everyone gives off.
See, I know that when I had that encounter with that ladyboy, not only did my eyes get fooled, I also got fooled by the subliminal vibe the ladyboy had – she felt female and, um, I was excited by that subliminal feel and, yes, I can easily admit that seeing her cock was one hell of a shock… but, er, one that I was able to get over and, nope, it didn’t take minutes to get over it – it took probably less than two seconds for my brain to say, “Holy shit, she has a dick! Oh, okay, let’s go for it anyway!” Yep, all of that didn’t mean that it didn’t fuck with me after the fact because it sure as hell did; I was very seriously pissed with myself and it took a long time for me to eventually admit that there was no point in me being pissed about something I had no control over; my mind and body reacted to what I saw, the things she said and, yep, the way she felt; for me, it was the ultimate lesson in not judging a book by its cover and that not everything is as it appears – or even feels – to be.
I did get to understand that if I were straight, well, that would have been a problem no matter how open-minded I was about such things but that it was my bisexuality that said it was okay to go for it despite the shock and awe I felt when she revealed all of herself to me. I remember laughing to myself (years later) and saying, “Yeah, well, she did have everything a guy likes except instead of a pussy to fuck, she did have a fuckable hole, didn’t she?” And I was okay with it all. The ladyboy was, hands down, good in bed; I say, unequivocally, that this was the best sex I’d ever had with a “guy” at that point in my life. In truth, it was the first time I’d had my ass eaten and, yes, the first time I ate some ass myself – it was so delightfully weird doing this and having it done to me; when I slid my dick into her ass and she wrapped herself around me, yeah, I have to admit that if it wasn’t for that erection pressed against my stomach as I fucked her, it felt like fucking a woman. And, no, despite the fact that she had a dick, she wasn’t interested in fucking me; she told me, as I got dressed to leave, “I have a dick but I’m a lady so guys like you are supposed to do the fucking, right?” Oh, she loved it when I was sucking on her cock as if my life depended on it and, uh-huh, loved it even more when she flooded my mouth with tasty sperm. But she made it clear – and in a similar way that only women can convey – that she wouldn’t fuck me even I begged her to do it because she’s a woman and, in her mind, women are made to be fucked by men and not the other way around. But, yeah, that was before I ever heard of pegging… but what she said to me about this strangely made sense at the time.
Holy shit, huh? Even after all the years that has passed since that landmark moment in my sexual life, I still can’t explain to myself why the experience was so good and at so many levels; I know that in my head, the answer is there but couched in so many intangible things that I just do not have the ability to put them into words – so I don’t try to. It was what it was and I learned some shit. Would I do it again? I just don’t know the answer to that…