How Did Your Love For Shemales Begin ?

[TSLuva]

For me it started about 7-8 years ago while going through porn sites I kept on seeing Shemale sites & curiosity got the better of me. One of the first girls I saw was Vanity & I couldn't beleive there were such stunning woman as these out there. Yet to work up the courage to actually go out & meet one of these ladies, but like they say the worst regrets in life to have are the things you haven't done. My curiosity into the actual physical act is severely tested.

[rancor169]

Magazine in friend's brother's room....

[joann-a]

It begins when I was teen,and try to find my identity.Some times I had dressed in female clothes,feeling an exitment.Now,I think that I could be one of them.

[BiancaLover]

My interest started when I saw Vaniity on an HBO special. Seeing her planted the Tranny seed in my brain. I then started checking out TS vids on bittorrent sites and now I'm more likely to get aroused from Tranny pron than ones with GG's.

[Slazer666]

Hey all! I'm new to this site and I guess I can start out healthily by writing out my shemale love story. Well It began when I was about...15. I fell in love with this girl named cassaundra. She was this tough, and inspiring girl and I wanted everything to do with her. She had an abortion and was going through a rough time and I took the opportunity to get to know her. Well I'm going to make this VERY LONG story a little shortened. We started to get to know eachother and she always held back for some reason. I had no idea why. One night when "love" was in the air she told me she had to tell me something. She said that she was a shemale. I was confused at first be she showed me...and for some reason I didn't care! Ta dah! Thats where it began so we did "It" that night. And I found out shemales actually make me . Unfortunately she moved away and I never saw her again. But Now I'm 18 and I've met the T-girl of my dreams. Her name is Briana and I'm in the deepest love I've ever been in! yay! so thats my story. (Yes I did date women before but it never really worked out)

[Candyboy222]

Originally Posted by Slazer666

Hey all! I'm new to this site and I guess I can start out healthily by writing out my shemale love story. Well It began when I was about...15. I fell in love with this girl named cassaundra. She was this tough, and inspiring girl and I wanted everything to do with her. She had an abortion and was going through a rough time and I took the opportunity to get to know her. Well I'm going to make this VERY LONG story a little shortened. We started to get to know eachother and she always held back for some reason. I had no idea why. One night when "love" was in the air she told me she had to tell me something. She said that she was a shemale. I was confused at first be she showed me...and for some reason I didn't care! Ta dah! Thats where it began so we did "It" that night. And I found out shemales actually make me . Unfortunately she moved away and I never saw her again. But Now I'm 18 and I've met the T-girl of my dreams. Her name is Briana and I'm in the deepest love I've ever been in! yay! so thats my story. (Yes I did date women before but it never really worked out)

Great story man with a happy ending. I wish you both all the best in life.

[PhillyBoy999]

It was 1985- I was a young horned up man in my late teens- and I had had a wet dream involving a beautiful woman- with gorgeous breasts and... a cock.

I thought a little about it, but such creatures are impossible... and that was that. Until I was in a porn shop in Soho London... I saw tranny porn mags in display. I was stunned! "They do exist!"

It was the classic 80s porn- and I remember being particularly intrigued by Pasha
(bad pic attached, but she really was so sexy). I was hooked and had to buy a bundle of mags.

It took me about 10 more years before I finally started dating tgirls- and my only regret is not starting earlier.

[epj290]

well for me it started going around looking at porn....i thought it was interesting..and found it sexy....i have always liked girls ( still do) and i thought this was sexy....i dont think its gay as some people make it seem....this was when i was 16 or so....im 19 now and hope to meet and have a relationship with a pretty shemale.

[lanakreuk]

i went on a trip to thailand and had the pleasure of spending the week with a beautiful slim pretty 19 year old ladyboy the sex was amazing the best blowjobs i have ever had. i also love women but enjoy the pleasure of a nice she cock

[hellos123]

I like shemales because i can watch them when i also masturbate in women's clothes. I dont know but i love it

[paris69]

I realize I like shemales some years ago.I don´t know the reason but when I watch lovely shemales like Carmen Cruz, Dannielle Foxxx or Amy for example, my body is very excited, my cock is hard ... I think a good shemale has the best of both worlds.

[jporter]

First started when I was searching for some anal porn and accidently found shemale porn. I had always like anal with women, never ever thought about having sex with a guy. I couldn't believe how many hot women there were with cocks. Feminine beauties that look exactly like women but have a cock. Not many women like anal and I want them to enjoy it but, no, most of them just do it to please men. I would like it much better if they enjoy it because it turns me on more. When I saw a feminine shemale get anal and shoot a load, that turned me on so much. Simply because I like giving anal and shemales like it and they let you know how much they like it by shooting a cum load.

[sherlock]

I started to love ladyboys a few years ago, when by accident I found a photo of one on the internet while I was looking for some porn. Before than, I never saw anything like that, so I closed it immediately, but very soon I started to think about it and I realized that i like it. Since than I dream about meeting one, but here where I live it's very difficult to find one.

[rockman0087]

mine started a few years ago when i bought a dvd and it had a preview section of transsexuals, after watching it i got very curious and started searching for more.

[TheCatfordCat]

I started being interested in crossdressing in my early teens, I'd try on some of my mums clothes and found it turned me on. Hopefully, she never found out - I'm more worried about the fact she knew I was wearing her clothes, than the fact she might know I was dressing! I still dress occasionally, but I'm not particularly feminine, and my interest is more in seeing other people dressed, and I'm trying to think back to when I started to take an interest in that. The earliest I remember is when I first started going into one of the sex shops in the town I grew up in, and being drawn towards the transsexual magazines. I remember seeing one with a guy picking up a 'girl' on the front, and it was the first time I became aware of how convincing transsexuals could be. Before long, I bought a couple of TS magazines, and it turned me on like nothing else ever has. I still use all kinds of porn, but TS/TV/CD stuff is definitely the stuff that turns me on the most. Of course, as soon as I had an interet connection, the first thing I went looking for was transsexuals, and, as they say, I've never looked back!

[bangee88]

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 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 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

[transexuallover69]

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.

[mabedzaqueen]

Originally Posted by bangee88

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 Later, while I experimented with more and more porn I realized that, in addition to female body, I admired nice cocks. I checked out some shemale sites and the love was born
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

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!!

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...

[avrilfuck]

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.

[TSBBG]

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.

[Yeah_Buddy]

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...

[jonnycakes]

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.

[Travielief]

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.

[Travielief]

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.

[Travielief]

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

[max53181]

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.

[RobbyPants]

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.

[DudeMan]

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.

[alwaysandnever33]

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.

[Be_my_nude]

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 ! "

to all

[mattyboy]

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.

[Conundrum]

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

[Dsp123]

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.

[eduardomachado]

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.

[jigenbakuda]

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...

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

[Pikachu1989]

With me it began in 2003 when I was 13 and started wearing a bra and high heels. I looked on the Internet and saw Transexual porn. I got hard instantly and JO and then deleated the History. I was Paranoid that someone will find out that I Kind of supressed my feelings for transexuals until 2009 but still wore Bras and high heels in secret. I found Transformations Magazine at one of the Borders (sadly it's closing) and I bought it and the memory came back. I then started looking at transexual porn on the Internet since I was now 20. Then went to porn shops a couple of months ago and bought Transexual porn. I now have more 25 movies. It's safe to say I'm hooked for life

[Zymurnaut]

How did my interest in ladyboys begin? Probably from reading a piece, don't remember if it was a feature or a letter, in Penthouse Variations in the early '80's.

[Pcows]

I moved from smalltown to LA. Lonely, i experimented with one guy. Not satisified, i sought out a TS. My first time was with a beautiful Black girl. She had gorgeous body and a large cock. I couldnt get enough of that large cock of hers. I could never fit it in me, but would suck her dry. After that,my obsession has grown and grown.

[whitedaddy]

My interest started when I was about 35 or so, in 1995. Long before the Internet. At the time I was married and my wife was dying. (She had Systemic Lupus.) I had been without sex for about three years and the only release I allowed myself was going to a nearby adult arcade and whacking off. (I couldn't bring myself to cheat on my dying wife. I wasn't that scummy!) The way the arcade was set up, you paid four dollars and walked into the arcade area. In the area was a display that showed which movies were on which of the 12 channels they provided and they always had two tgirl movies playing. There were about 20 rooms and I always chose one of the five or so that didn't have gloryholes in them.

I never paid much attention to which movie was on which channel, so I'm surfing the channels and come across a hot blonde in a bikini sucking off a guy by a pool. She really turned me on, so I settled back and watched. After a 5 minute suck-off, she started taking off her bikini bottom. As she slowly pulled them down, I noticed a small heart-shaped spot at the top of her crotch area. She was very tanned but had apparently put a heart-shaped sticker there while tanning, resulting in a non-tanned area shaped like a heart. I thought that was pretty hot and was really admiring it when she pulled down her bottom completely to reveal a small cock! To say that I was shocked was an understatement, but I was also VERY turned on. I knew what a shemale was at that point, but I haad never been interested in them.

Anyway, she obviously couldn't achieve an erection, even with her partner sucking it, but all the while I was fascinated. I started jacking off, thinking about phrases I had heard like "the best of both worlds" and "boys will be girls" and trying to convince myself that being with a shemale wouldn't be cheating because she wasn't a "real woman". I exploded like crazy and watched the whole movie through several times.

I lived in Houston, so a few nights later, I drove through the Montrose area, looking at the shemale hookers and getting SO turned on! I never picked one up, but I had a lot of nights whacking off to the image of them parading down the streets of the Montrose.

I never cheated on my wife, but after she died in 1996, I waited about 6 months and started calling the phone sex lines which were popular at the time. One lady I talked with told me that she was a shemale and that while she wasn't interested in sex on the first date, she would teach me about transsexuals and take me out to the clubs. It was a fun night and I couldn't believe all of the hot, sexy ladies at these clubs. My date, Michelle, told me that most of them were hookers and to stay away from them. I did, but boy was I excited!

Michelle and I never did get together. She had to leave town about a week later to take care of her sick mother back in Baton Rouge (where, coincidentally, I had lived for 17 years). By then, I knew where the clubs were and I began hanging out there. I'll admit that I tried a few TS hookers, but I quickly learned that I was no bottom and stuck to the girls who were not tops from then on, which pretty much ruled out the pros.

I lived with a sexy tgirl for a couple of years (she was a nurse), but we argued so much that the relationship didn't go any farther and when I lost my job and moved to Atlanta, I pretty much dated genetic women from then on. I'm married now but I really miss the tgirls.

[maleesh]

My turn on started when I was about 23. My main fetish are pantyhose and i really love to see women wearing them. Also I love to watch anal sex (to much French porn :P ). As internet grew bigger there was more and more common to came across a transsexual women in a pantyhose gallery site. so as most of them wore pantyhose models and were really hot and didn't give a clue that it was a transsexual, I've started to be turned on by them. At first I felt ashamed because I don't find males attractive at all but as transsexual women looked like really hot females and they could get only anal sex, I've started to watch that kind of porn more and more. Now i just love them while in nylons and pantyhose, especially femboys that really look as girls
but I've never been with a shemale in RL nor I will ever be because I'm stable and happy relationship now with good amount of pantyhose sex. if only she would like anal sex more (she do it maybe once-twice a year just for me)

[Lulu38c]

My attraction to shemales started in my early 20's.
I did not know in that time they were existing... I was just fantasizing about myself with large breasts. I had just hit 30 when I came across shemales pictures on the internet. I got to find out they were called "She-males".
"Wow", did I think, "They are exactly what I fantasize to be!"

The closest I got to become is a crossdresser. If I had the money it would be different. I couldn't care less about anybody's opinion and I would go for breast implants, and a few other alterations (face and body).

I would like to be into a long, serious relationship with one of them.

Lulu

[damiangentile]

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

[bigd631]

Mine started around 14 I found a AVN magazine that had adds for Best of Both worlds in it and I was captivated ever since

[rdtremolo]

It was Bailey Jay, on 4chan where posters would occasionally post an image to get people to comment that she was cute before telling them she had a wang.

Saw some of her youtube stuff, thought she had a really cute voice and mannerisms and thought it'd be dumb to suppress my attraction.

[suckerpunch]

I saw an advert for a ts mag in a regular mag sometime in the early 90's & that image stuck in my head I wouldn't say initially it aroused me I was more curious. When the internet came along (dial-up) I already knew the term "shemale" so I looked around for stuff. The more I looked the more familiar I got with the girls names & models & I think shemalesxxx was one of the very first sites I found & that had a chatroom at one point called tgirlchat & it annoyed me when it shut down.

I've done the whole sexuality battle for so long, I'm at the age now where it doesn't bother me anymore, I just go with the flow there is nothing wrong in it. What freaks me at times is when I see how many years I've registered on various forums like hungdevils or hungangels its certainly not a "phase" any more.

[Boner]

I've done the whole sexuality battle for so long, I'm at the age now where it doesn't bother me anymore, I just go with the flow there is nothing wrong in it. What freaks me at times is when I see how many years I've registered on various forums like hungdevils or hungangels its certainly not a "phase" any more.[/QUOTE]

I did the sexuality battle thing too but got to the point when I realized I like what I like and there's nothing wrong with that. I don't share my preferences with everyone but I'm not in denial about liking these special ladies anymore.

I can't say exactly when my attraction started but it was through porn. I remember seeing Karen Dior done up as Peg Bundy on the cover of one of those giant VHS boxes that porno movies used to come in and thinking she looked fantastic. A couple of years later I was on Vanessa Del Rio's site and got really turned on by a photo set of her wearing a strap on. But it wasn't until I saw Gia Darling on another of those box covers that the tgirl bug really bit me.

I took the tape home and the first scene had Johanna Bardine being blown by some guy. I was repulsed and excited all at the same time and swore I'd never look at tranny porn again. Needless to say I was on the internet a few days later looking for more Gia Darling and I stumbled on Bob's Tgirls. Holy shit! I'd never seen such beautiful women. I still love genetic females but I haven't looked at "straight porn" since.

[Lafuerza]

Originally Posted by Boner

I did the sexuality battle thing too but got to the point when I realized I like what I like and there's nothing wrong with that. I don't share my preferences with everyone but I'm not in denial about liking these special ladies anymore.

I can't say exactly when my attraction started but it was through porn. I remember seeing Karen Dior done up as Peg Bundy on the cover of one of those giant VHS boxes that porno movies used to come in and thinking she looked fantastic. A couple of years later I was on Vanessa Del Rio's site and got really turned on by a photo set of her wearing a strap on. But it wasn't until I saw Gia Darling on another of those box covers that the tgirl bug really bit me.

I took the tape home and the first scene had Johanna Bardine being blown by some guy. I was repulsed and excited all at the same time and swore I'd never look at tranny porn again. Needless to say I was on the internet a few days later looking for more Gia Darling and I stumbled on Bob's Tgirls. Holy shit! I'd never seen such beautiful women. I still love genetic females but I haven't looked at "straight porn" since.

About this (emphasis mine), aside from porn that was more about certain fetishes (really big boobs/penises, strap-ons, rimming, etc) I've largely strayed from straight porn as well. There's obviously no lack of beautiful women there, but purely looking at sex there is just no spark for me.

[dim dom]

Originally Posted by damiangentile

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

ATTN damiangentile, YOUR AVATAR PICTURE OF THAT YOUNG WOMAN LOOKS SO GOOD, she certainly is a yum yum dick.

Years ago when i was a teenager, i thought to myself, "i can't believe it but is it true that really really pretty women can have a cock that gets biggie, hard and wet?" Ever since then after i realized that i always loved and lusted them.

[ARIES666]

I saw an advertisement in the back pages of a "glamour/girlie magazine" for VHS (maybe 8mm film) movies featuring "Sulka" and "Carnal Candy". It hade to be in 1980's. There were only a few screenshots in the ad from the movies, but Sulka and Candy really caught my eye and fired my imagination. I found it incredible that they looked so feminine, so sexy and so glamorous. I was hooked from then on.

[poseilah]

I think I started enjoying TS when I was "tricked" in a camXcam chat... I was talking to this beatiful girl and then she pulled out a cock... at first I was "WTF?" But then we talked and talked a lot... we became friends and I started seeing TS differently...

I lost contact with this girl, but my desire to be with a TS stood!