Frankly, I dont´know. And is not important for me.
I like her, I love her, I wanna make love with her. Sex with them is confortable.

So, I don´t worry about why or when it begins.

A long time ago my route to work took me past a tranny bar. I would drive by it and notice how good-looking some of the girls were. Down the block from the bar, I would always see a tranny prostitute sitting at a bus stop. She had a gorgeous body, and I began fantasizing about her. I never met her, and I changed jobs, so I never visited that area of town again. Back then, I would try to resist fantasizing about making love to a shemale. Then I noticed the famous model Giselle somewhere. I couldn't get her out of my head. I stopped resisting and dove right into the websites. I've never been with a shemale but I eventually will meet one of the escorts.

i was younger, and I was on a porn site. when i was that age i was really into gay porn (not as much as i liked girls though) and i really didnt like looking at guys faces, but didnt realize it quite yet....

i was in the mood to look at balls specifically... dunno why.... but i typed in balls on a sex search engine and a picture of a tarnny came up and i just looked at her in amazement. ever since then, i really dont look at gay porn and i almost always watch shemale/crossdresser porn

hooked
 

As a teenager my relationships with women were also not ideal and I started to use escorts. I would search the small adds then one in particular caught my eye it said 'Tara Domme TV'. I took the plunge and phoned her and as luck would have it she lived within a mile of my house. I went round straight away. Over a drink we discussed what I wanted and then went upstairs to her playroom. She tied my up and started to give me the best blow job I had ever had. Then she asked me if I wanted to suck her and I said yes. She untied me and got me on my knees sucking her cock, I loved it. Then she said "Every time you fuck your girlfriend you will think about my girly cock in your mouth' I came almost immediately. Every time I had sex with a genetic girl after that I thought about shemales.

For me it's been a slow realization with clues all around. As a college student, I once masturbated to female porn with fishnet stockings and a slip. Not that I was particularly interested in cross dressing -- but it was a nice treat and I enjoyed the feeling of the soft silky material as it draped over my cock. At that time I also first tried anal insertion and it really blew me away! I didn't have too many opportunities for the "slip treats" but did make the time to try various items to play with up my ass -- but always with female porn. Lesbian was my preferred type with strap on being the main attraction. I was looking for strap on porn when I stumbled across shemales. I was aware of it but it was never really on my radar. Some was mixed in a new site I was on and what looked like some very hot girls turned out to really be my own shemale surprise. I was intrigued and my raging hard on was the proof. :turnon: It took a a few sessions to build up the courage to allow myself to cum with this new material, but once I did I knew I was hooked. For the record, Christina Bianchini was the first one to catch my eye and Mara Dorantes was the first one to come with.

I been liking shemales I was 19...I'm a straight guy but I love pretty shemales...I tried to stop liking shemales but I always go look on the internet for shemale pics...I never had a thought of havin sex wit one but I just love to watch them stroke their big cocks wit thick cum exploding on their stomachs...I just don't know what's sexy about them but I love them...

Kind of a long story actually. I didn't discover internet porn until i was a sophmore in high school. Back then i mostly browsed a website that hosted categorized porn. One day, my hand grazed the mouse and i inadvertently clicked on the "shemale" category. Out of curiosity, I clicked the first link i saw; It was a photo of Sylvia Boots. The rest as they say is history.

Do not really remember
 

I do not really remember all only that I was quite young (below 12) when a friend found a book at street with a girl with a penis. Never seen that before but I liked it. Later on no and then I heard stories about transsexuals in the press and as I started crossdressing myself I grew a broad mind. Around 18 I was looking in a sex shops for books about shaved girls (was not so common at that time) and found also books of shemales. As I came in heaven. I bought some books and firstly had to make a switch in my mind but soon I loved the girls with the nice penises. Especially the slim young girls with normal not to large breasts and a nice smooth cock. Like the girl at the picture.

One of the girls of the book I bought - the start
 

This one of the girls that was in one of the first books I bought. Lovely little dick and an empty sack. I like them this way.:turnon:

Also a lovely girl
 

This girl made me mad as well. During the years I like to see shemales more than genitic woman. I like to see them but after several smooth cunts I turn back to my girls again. If I was young and single now I would try to get in tough with a nice transsexual for a relationship

It was around twenty years ago, i was looking through an old german porn magazine and it was there!!! Something I could not believe existed. It cought my imagination. And I had fantasies about it since..

teenage years,i have had gfs in the past,but its too much drama and other bullshit to deal with dating them.i still love pussy,just attracted to shemales more because we can relate to them more than we can women.you get the same beauties and features (besides the cock) as you get in a real woman,but with less drama.you can hang out with some shemales,watch football with them,fuck them,and be happy with them.lets be honest,they were men once so they share some of the same interest as us.its amazing.i love shemales

For me it started very early, i think i was 16, and i want it more and more, so now i hope to find a perfect one for me to stay with for a loooooong time...

I was about 13 or 14 years old when I came across an autobiography by Caroline Cossey (aka Tula), an English fashion model / actress. In it, she describers her childhood, transition and life as a woman. I was simply transfixed by her story (a boy becoming a beautiful woman). From that moment onwards, my life changed...as I grew older, I graduated to browsing cellophane wrapped magazines of seedy book stores, in search of copies of Transsexual Climax.

Where I differ from most of the responses to this post, is that I never fantasized about being with a shamale in the pictorials, I yearned to be that shemale.

Same here.

When I first saw shemale porn, I turned away from it coz it was so strange. But slowly and cautiously I viewed it, and I was extremely turned on. I could jack off many times in a row to shemale porn.

But then it got me to think, what it is that's making me horny?

Am I horny coz I want to fuck a shemale? Like, putting my dick in her mouth and her ass?

Sure.... I would like to do that... but I can do that to anyone to have similar effect... I could just fuck a woman for that.

Surely there is something else in shemale porn...

And I thought I was the shemale, getting fucked by the guys... and bingo. A HUGE HUGE hard on. When I saw a picture of a shemale getting fucked by a guy, I wanted to be the shemale in that picture.

first attracttacted
 

I loved sucking cock before wanting ladyboys, but I think it was because they were so beautiful, and so sexy. Ladyboys I can't resist, but only certain guys I will suck-off. Ladyboys, and shemales are sexually above everyone else, an arousal sexual experience, thet goes beyond. That's my opinion, and I think it scares some people.

Well, i've been fantasizing about cock - gay/bi porn for probably 10 years off and on. I started with shemale porn about 5 years ago. For me, i don't like watching guys kiss. I took the leap and live action about 3 years ago and I love it, can't get enough of shemale cock. OH... i'm 43.

One night in my teens, I was downloading some porn. One of the videos was sneakily labeled as "Redhead masturbating." Little did I know it was two crossdressers in wigs masterbating together. I've been curious ever since, growing to the point where I'm a casual crossdresser myself.

ive been cross dressing since i was age 4. when I got older i was looking for people that were like me and came across pictures of ladyboy's on the web it turned me on instantly.

When i was around 12-13 years old and the internet was still 56k and slow to load ... a friend of mine messed around and put chickswithdicks.com as my homepage as a joke. Well sure enough I changed it back. Thing is - i wound up going back and looking at it later and realizing how much I liked it. Needless to say that was the start. :turnon:

it was in 1974, hanging around the streets of Minneapolis, Minnesota...

I went through a strong self-feminization phase when in my late teens to mid twenties, but I grew out of it when i reached 27 or 28. But my interest in T-girls, in particular black and those wearing lots of make-up, remained.
Anybody in here remembering British pop star Boy George? I don't know how he would label himself, but I always thought he looked so damned hot. When I found out that he wasn't actually a "real girl", I still had the hots for him.

Special
 

I first saw the woman that would change my life in a hustler magazine, she was blonde and beautiful, and she had a penis. My uncle had left it out for my father and grandfather to see, sort of as a joke I suppose, but it just burned into my mind. Another group I belong to identified her as Gia Darling, and the Hustler was there April Fools issue, but I loved it. I brought many things into focus for me. I had always been around strong females, and many may say abused sexually, as one of my baby sitters used to let me play with her very attractive feet and toes, (hello foot fetish), licking and sucking them, she would have me kiss up to her pantied waist, and even the panties themselves. She would also nurse me, letting me suckle and drink her milk from her beautiful breasts, (strong fetish for lactation and preg), She would always ask me if I liked it, and encourage me to hold her breasts in my hands and caress them, lick them and suck on the nipples. She also started to dress me in girl clothes when my parents where not around. Later, I had a neighbor boy who dressed in girl clothes, and he helped me further with experimentation and feminization. I did not realize what was going on, but my path was being set. Soon enough I saw the Hustler and knew that boys could really be beautiful, then came the breakthrough, a bondage video with two beautiful women, slave and mistress, and they showed their day, with training and what not, but at the end, when the mistress was putting her slave to bed, she pulled down those lovely panties, and the slavegirl had a cute little penis. So shocking and erotic. I had to be that girl. My experiments with the boy next door grew, to the point where I was fully dressed, fully femmed, and sucking his pantied cock, everyday if possible, and then letting him fuck my hot little ass. The first time was incrediable, and I knew that I wanted nothing more then to be the girl always. I wore panties to school, wore bras under shirts, when I had nothing for them to hold, but the mental feel was incrediable, as was the material against my always hard nipples. My toenails were always painted, and I grew my hair long. High school was sometimes a chore, but I wanted to be the girl. Since then I have sought out material with girls like me, and loved it.

Age 16 ...online

I was in my early 20's when I started looking at shemales.
I like anything that is out of the ordinary so it was only natural that I would come to like them as well.

When I was about 11 or 12 I saw a magazine article about an all male review - Les Girls. The girls looked absolutely gorgeous. They were so beautiful and glamourous. I have been fascinated by transexuals ever since. It was not until I was into my 30's that I finally saw my first shemale porn. To me the sight of a beautiful female body with a beautiful erect penis is the most erotic sight of all

Ever since i could remember. I liked Girls who where boys,and boys who were girls.

:inlove:

I was 18 or 19 i think and saw a clip. It turned me on and i continued looking for pics and vids. Now i cant think of dreams without ladyboys :)

How did you discover your love for shemales?
 

I started watching shemale stuff when I saw by chance a video of Long Mint.
I thought that girls with cocks look better...:turnon:

Mine is pretty much the same as yours there, just omit the pussy part, never cared for it then, and certainly don't care for it, now.

I do not care much for football, either. I'd rather play it than watch it.

I saw a transvestite in a magazine and got warm. At 22 he was my first time

I stumbled across a scene in a porno I rented years back. It was a mix of different fetish's and when I saw the girl had a cock I got so hard.

i used to think of cocks as a complete turn off, and shemales as not my cup of tea. then i saw a short clip of thais schiavinato getting sucked off by a guy and felt very aroused. so i kept looking for tgirls porn and discovered how sexy and feminine some were and how i liked it. i just had to review my thoughts about sex and sexual orientation and admit i was not such a 100% straight guy. like most of other guys in this forum i'm not attracted by men , at least not particularly, but i learned to love and like a transexual body to the point that i don't find anymore a pussy (the thing that we all men are supposed to be after day and night) such a turn on. now i prefer to masturbate watching girls with cocks. it is not only sexual fetish, i came across an aspect of our society which is hidden. i learnt to actually love and respect people brave enough to change their sex and go through (in most cases) all the worst human nature can offer. now i don't tolerate anymore sexist jokes against them or all the discriminations they're supposed to put up with. i appreciate the fact that discovering and loving the transexual world has made me grow up as a human being.

Same story as you, initially.
Obviously our subsequent paths in life, were rather different!

About two years ago, I bumped into this girl in the mall. I had no idea she was transsexual. I just found her beautiful. Next thing I know we are playing cat and mouse in the mall. I'd follow her for a while, she'd follow me. We never actually made contact at the time, it was just an accidental flirt. Everytime since then, whenever I happened to see her, she was like this giant magnet and I was IronMan. My emotions and sensations also are very strong for her, more than any gg i've met, . I am very happy now that I'm starting to get to know her. I am very passionate for her.Just recently we've made contact. It's only since I have met her that I think I know the meaning of love. I have never felt this way towards any gg before. They say you dont control who you fall in love with.:hug::heart:

Just another part of my rather twisted pathology, can't pinpoint when it began. I just know the duality between the female figure and the penis turned me on when I came across pictures of it online.

Side Show hermaphrodite
 

Many years ago, I attended the Central Wiconsin State fair. Walking around the fair grounds, I found myself in front of the Side Show tent. The side show barker brought up on stage a less than attractive woman and claimed she was a hermaphrodite. I was intrigued and paid for entrance. It turned out that an additional fee was required to see her/him which I paid. Soon the woman appeared wearing a small square apron covering her genitals. She gave her speal, claiming her gonads were internal and that she was capable of impregnating herself. Shortly she removed the apron revealing a perfectly formed flacid penis where her clit should have been. She grasped it and gave it a herty pull and you could see that it was indeed real and not an appliance. After a little play, the penis became semi-erect. She offered to the crowd to let anyone examine it as close as they liked but no one came forward. To prove her vagina was real, she borrowed a lit cigarette from the man to my right. She inserted the cigarette between her pussy lips and took a drag on it then blew the smoke out. Offering the cigarette back, the man brushed to the ground and crushed it out.

The image of this woman/man has been burned into my brain for over fifty years and has been the source of many masturbatory fantasies since. I have been turned on to shemales and hermaphrodites since that day.

Mine was basically through porn. I go to thehun a lot, which has links of about anything you can think of, and after seeing links for a while, I got curious. I was kind of neutral to it at first, but after a while, I found myself clicking more of the links.

A segment on Sex Bytes 2.1
 

My love for transsexuals began when I was about 15(over ten years ago). I was watching Sex Bytes 2.1 on HBO. One of the segments was with Brandy Scott and Kelly Michaels. I had never even heard of transsexuals, but this turned me on like nothing else had before. It was an awesome segment, you didn't know that they are TS until half way through it. They were doing a shower scene, when they get out they both have big cocks(surprise)! I was already turned on so I just went with it. It was spectacular. I taped it and watched it over and over again. I don't know why, but it was just the hottest thing ever. Hot chicks who have cocks, this blew my mind. "You're sucking on a girl's dick" - This made a lot of sense to me(and made me feel comfortable with the idea). After a while I was very comfortable with the idea. Transsexuals are on a whole different level, nothing turns me on like they do.
Here's a link for the video that got me turned on to TS.

I'm pretty sure I stumbled upon a video of Mariana Cordoba with her, two dudes, and another girl and fell in love instantly. I usually watched lesbian or gay porn at the time so seeing a chick with a huge cock was the best of both worlds and everything just clicked. :turnon:

Odd maybe ?
 

For me it was almost by way of a professional enquiry - not a direct need to know, but more something that I fell I needed to contact to understand ! I am still working on it - sometimes with pleasure, sometimes with surprise.

Knowledge has no bounds for the enquiring.

Meantime - as they say in the countryside round here - " Up and at 'em lads ! "

:respect: to all

My love of shemale porn started when I one day came across a video of Ana Mancini. I got very turned on and I started analysing it and came to the realisation that I really get turned on by cocks but hate everything else about the male body as well as not being attracted to male personalities. I also absolutely love the female form so for me a chick with a dick is the best of both worlds.

While at an adult bookstore in 1970-something. I saw a magazine featuring Sulka and the rest is history. :)

I guess it began when i was 4 years old. At the time, I thought boys and girls both had dicks. Whenever I took my mom's Victoria Secret magazines I would picture them with penises. Years later I looked back upon that as some silly misunderstanding about the female anatomy. When i was about 15 I stumbled upon this one shemale vid on moviefap.com. It had two asian shemales jerking off until they came. I had this weird feeling and got really turned on. I spent like 3 more hours searching for more of the stuff.

I guess this is a fine thread to start posting. I saw a shemale for the first time in some magazine when I was a very young teenager. I remember that she had so feminine face and body that I immediately dissmissed the pictures as fake. I was very naive :blush: Later, while I experimented with more and more porn I realized that, in addition to female body, I admired nice cocks. I never found anything attractive in a male form, in real life or in porn, but the cocks really turned me on. I checked out some shemale sites and the love was born :inlove: For me, shemales have the best of both worlds, and give me the ultimate pleasure.
Although, it might have started when I was a kid and had a friend who used to put a wig, dress up, and act like a girl, and I sometimes thought that he looks cute dressed as a girl. But that's another story :cool:

tgirls give me the biggest and best cumshot. I used to cyber to girls then I tried a tgirl and I had a massive load. Then I tried tgirl porn and I came so hard. then I knew tgirls are for me. they make me cum so hard.

a rather unglamorous beginning...
 

Enjoyed your post, Bangee... At first, back in 2003, i also naively suspected some trickery was used in these new to me, incredible photos of Victoria (who later became well-known as Miriam Rivera) and a host of other brazilian hotties, and i had to rent a dvd to make sure... (There were no "tube" sites back then). Though initially a bit put off by the vulgar appearance of most of the covers, i quickly became a regular at ordering dvds online and... yet another "tranny porn addict" was born!!:drool:

But something happened to me in early 2006: one evening i was surfing free sites and saw a (beyond) gorgeous blonde latina with a dick in four 30 secs samples from a solo scene and, for the first (and only) time of my life, i possibly had a hint at what some call "love at first sight"... Until 2 a.m. or so, i tried to find anything else on her, with no luck :( Fortunately, in the following months, free pics and other short movies of her slowly began to circulate...

Hmmm To prevent this post from becoming a longish off-topic affair it will be continued (soon, hopefully) in the thread dedicated to "the lovely Thays Schiavinato", in the Freebies section...

It happened when I was fifteen. It was very strange. I was watching some amateur porn (supposed to be heterosexual only) and then that blond girl with that great butt simply pulled out a hard cock and started jerking. My dick got even harder. It took me a long time to truly accept it, and I still don't understand why I like shemales so much, but I guess it doesn't matter. Also, never found the video again, sadly.

I read a futanari manga (genetic girls with penises) and was very turned on by the concept of a woman with a penis. I discovered that the penis is not feminine or masculine, but simply an appendage. So I started getting into shemale porn. And for as unrealistic as it is... it sure is good fappin...:turnon:

Unfortunately I have not met, dated, or seduced a transgendered lady so far, but I'm working on it, hehe:yes:

about 12 years ago... and she was the guilty one... The one and (almost) only Shawna.