How you got into Shemales

[speck]

There used to be lots of unbelievably attractive hookers on Sunset Bl. in Hollywood. I have no idea what Hugh Grant was doing with Devine Brown, because I have picked up legitimate 7's, 8's, and 9's at the same intersection where he was nailed. This continued into early 2005 or so.

Anywho, occasionally LAPD would just completely shut down the Bl. and no ho's would be available. So I would cruise the TONS of ts working on Santa Monica and nearby areas. Some nights there would be more than 100 ts out working. Eventually one night I was really horny and no gg sw's out. So I picked up a really fem looking ts with large implants. I reasoned that it was just a BJ. And I liked it. I picked her up again the next week. But this time she pulled down her jeans and her thong. Instead of going down on me, she forced me to go down on her. I didn't resist much. I liked how hard she came(not in my mouth) & how forceful she was. I started checking out ts sites on the internet. I thought a lot of the girls were attractive. I was surprised to see many of the ts from the internet sites out on SM Bl. So that started it. I didn't have a lot of money, nor a nice car at the time, but being in my early 20's and clean cut helped quite a bit, and more than a few of the ts literally pounced on me.

[christianxxx]

When I was in college back in San Antonio, Texas in 1997. I met Ms. Ree, a local radio DJ, who was also a shemale. She was mesmerizing, tall, long real hair, and gigantic fake boobs. I got her number, and hooked up with her that nite at her place. She was a top, and it hurt but felt good at the same time. After that I met Erica Andrews at a TS club called the Saint and I was hooked!

[Looking 4 Now]

I was looking for an escort in Screw mag. when I came across the shemale section. I really had no idea what a shemale was and I found it hard to believe that some of the shemales weren't girls. I wasn't attracted but more curious and I had to see more for myself. Eventually I rented a video and to my surprise I became very aroused. When it came to sex I was always looking to experiment and do something new and different with a girl. Well, this sure was different! I think the fact that I wasn't supposed to be attracted made it more exciting. Anyway, one night I walked into the old Edelweiss on eleventh Ave in NYC and that sealed the deal.

[TomSelis]

I told both of these stories before but I never told them together.

The first time I became aware of ts girls, I was like 10 or 11. I discovered my father's secret stash of porno mags and I would sneak into the stash and thumb through it. He had hustlers and playboys, the usual dad's porno stash stuff. One day I was thumbing through one that said "Hello? Jane?" It was basically a spead of a girl on the phone taking her clothes off and at the end she had a dick. It didn't freak me out, but it was a definite curiousity of the stash.

That was in the back of my mind, but I never tried anything. Even though me and my friends would go bar hopping in NYC's village and SoHo, some nights we would end up around the meat packing district and there used to be a lot of ts street walkers down there.

I graduated college, but I still liked to hang out in the city. I saw a thick dominican girl who was really cute. I said something really dumb and funny and started talking to her. I got her number and we started talking on the phone and going out. She cooked me dinner and it was great. A really good relationship. I had absolutely no clue she was a TS until she decided to let me get some, i.e. let me in on her secret.

I was shocked, confused, what ever you want to call it, but I was pretty fucked up from the whole situation. When you're 21-22, you already have identity issues and that didn't really help. So I did what any 22 year old would do, being that I had strong feelings for her, I moved in.

Things were pretty good, just like any other boyfriend and girlfriend. Things started turning sour when I discovered she had a pretty expensive coke habit and that she escorted occasionally. After about a year together I moved out.

I've been looking for a good relationship like that ever since, minus the coke habit/escorting.

Once bitten, forever smitten.

[Hawaiitslvr]

I was about 16 ... buying porno mags at a local dive ... into busty girls ... opened up one spread and it was one of those flip outs ... saw this really exotic looking woman ... tons of make-up, huge boobs ... wonderful I thought! then as I opened it fully there was this cock hanging where there should have been a pussy ... it was Sulka ... I felt a rush of excitment like an electric shock ... or was it shame??

Fast forward ... now in my 20's started renting shemale porn ... but had never seen any in the "flesh" where I lived ... moved to HI ... saw them everywhere ... finally after a few years ... found out where the street walkers were ... picked up my first tranny during Xmas ... she was dressed as an elf ... the most fantastic ass and legs I had ever seen ... took her home ... caressed and massaged her body for over an hour then received CBJ ... and that was what I did for several years ... then gadually moved "up" to other activities ...

Now I am an older fart recently married, wife knows of my interest ... but not of my "activities" .... and the beat goes on.

HIGuy

[JohnnyWalkerBlackLabel]

I was looking for an escort in Screw mag. when I came across the shemale section. I really had no idea what a shemale was and I found it hard to believe that some of the shemales weren't girls. I wasn't attracted but more curious and I had to see more for myself. Eventually I rented a video and to my surprise I became very aroused. When it came to sex I was always looking to experiment and do something new and different with a girl. Well, this sure was different! I think the fact that I wasn't supposed to be attracted made it more exciting. Anyway, one night I walked into the old Edelweiss on eleventh Ave in NYC and that sealed the deal.

Screw mag intrigued quite a few of us I see
lol

[hwbs]

i just met a hot tranny that my friend knew at this latin club and we just hit it off .....i didnt even have a computer back then....back then the only trannies i had exposure to were 60 yr old ones buying lumber at home depot, lmao...

[Quinn]

For me, it all started with an intro from a friend at the annual Delaware Water Gap Jazz and Arts Festival in the Poconos. I was in my mid-twenties and had just moved there in order to break away from my past at the Jersey Shore.

She was really cool, and we hit it off so fast it was frightening. At first, I didn't have much of a clue what she was. Today I would know, but back then the only thing that seemed a little off was her voice. By the time she told me her deal, I didn't much care either way. We actually dated for quite awhile. She was a very special person.

-Quinn

[skweetis]

wow...you guys have 10x better stories than me.
i would look at my dad's hustler mags and they'd have girls with strap ons at the end advertising stuff, i liked that. sometimes they'd have trannies, i became aroused instantly. i don't know what it is, i love the fact of being surprised with it. if it happened to me with a girl i was dating, i'd probably die of too much arousal (my cock would probably explode.) i just fear buying shemale porn since people don't know this yet, people don't know a lot about me. i am a drug addict who has o.d.'ed a couple of times, and come very close to death. my heath, although i don't go to a doctor, i know is not good. and i'm pretty young (well, than you more experienced guys.) i would love to meet a transsexual and fall in love with her, but where i live, it doesn't really cater to that. all it does cater to is death to fags and abandonment by the family. i sometime think that looking a shemale porn, while it's definately my favorite of all, is somewhat a waste of time, i doubt i'll live to see one and get to know her. my life has been pretty fucked up even with g.g.'s, who i've had serious relationships with, but my drug problems come in the way of everything. sorry for spilling too much info, but i just would like to know that all of you are very lucky in my eyes, even to be with a transsexual hooker, even how screwed up that may seem. i don't think i'll ever come out to my parents, even though i know what i am. i never down the gay or transsexual community though, i'm totally pro-it. consider yourself lucky with what you have or what you had, whether it be big or small (no pun intended.) ON WITH THE GREAT STORIES.

[Rubber Soul]

For me...it was just a progression to the next 'exotic' thing.

staright....3 way....anal....gangbang.....bukkake...trannies