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  #1  
Old 03-09-2009
spirit09 spirit09 is offline
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Default How long until you had sex with a tgirl?

I mean, from the time you started to look at tgirls, how long was it until you actually were with one?

I've been looking online pretty much all the time for about 6 months but I still don't have the courage to meet one(escort)
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  #2  
Old 03-09-2009
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A time be steady in an other the gender was nearly of two years with Tgirl

and had passed in a group from them and many from them Nice

little there and from them the ill-treatment but two little
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  #3  
Old 12-23-2009
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I first jacked off to them in 2001, i didnt have sex with one until 2008. So many wasted years...
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Old 12-24-2009
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I did it before I knew it....lol
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  #5  
Old 12-24-2009
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Default Interesting ? ,,,,

For myself it was far too many years between when I 1st knew I wanted to be with and enjoy a ts girl. I don't quite recall now when I 1st knew I wanted to,, but was sometime in the early 90's. Alas, it wasn't until 2006 that I actually fulfilled my desire,,, and I've been making up for lost time ever since,,, hehe
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  #6  
Old 12-24-2009
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In the last about 12 years I am more and more attracted by Tgirls, ladyboys and at last even femboys.
It started with an encounter in a bar with a Tgirl that I didn`t realise as one until we "came to the point". It was a real "coup de foudre" and I still remember her kisses and that I have never been kissed that way before. And I still think that Tgirls are the best kissers - I have not met a ladyboy or femboy until now - and I long for those kisses. You see I´m very much into kissing.
Unfortunately in my area it is hard to find a Tgirl, ladyboy or femboy to create a closer relationship or for living together.
When I was a boy I was yet very much attracted by female lingerie and this interest is increasing and turning to the interest in wearing it and - if I can find somebody - but not a man - who guides me in trying a sissyfication.
I would be very happy if I could find someone by means of that forum.
I am from Austria (Europe) and am willing to travel up to about 500 km.
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  #7  
Old 12-24-2009
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I was 14 and it wasn't until I was 28. I think it's really weird that I didnt go for them while I was younger
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Old 12-25-2009
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It was probably 2 or 3 years. It's not that I didn't have a chance, it's just that i kept backing out several times. The first time I was very nervous.
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  #9  
Old 12-25-2009
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I must have been 17 or 18 when I first discovered the Color Climax shemale magazines and a hitherto unknown world of pleasure was revealed to me. :-)

Took me up to my first year after college until I actually had sex with a tgirl. Now, I try to hook up with A., a lovely Belgian tgirl in Antwerp at least once a month.

For all the guys here who are still on the fence, do it! It's simply the best sex a guy can get.
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  #10  
Old 12-25-2009
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Been into TS ladies since around 95ish?! Got my first internet connection. Was surfing porn and happened upon a page with a VERY passable TS lady on it.
I've masturbated about sex with guys which got me very hot. I'd never do that though. Sex with a guy that is. Then when I got my first taste of how sexy a TS is... I've been a big admirer ever since.

Throughout the years, I've dated alot of Females. Lot's of sex there... But never thought of the possibility of being with a real TS. The last 3 years though, I've realized I'm getting older and I want to fullfill my wish and experience the whole TS thing. So I got on Gay.com. I found a room dedicated to TS and had a blast talking with the ladies on there.

Luck would have it, I found a lady (oriental) that lived only a few blocks from me. We got together and that was it! I had sex with a shemale!!! She was a top so she slaved my ass. She looked so hot, looking back at here while she rammed me hard.

That was my first experience.

Since then, I've not been fortunate. I did however find an escort in my city. Only 2 months ago. A BLACK TS GIRL!!! (Once you go black, you never go back). Made the call, went to the bank machine and got the $300 in my pocket. She came over, took her coat off and followed me to my bedroom. She looked so damn hot! Her dark, smooth brown skin. A face and body that I melted over. She had tit's to die for. Nipples that felt so good on my lips and tongue. Just like eating candy. SOOO TASTY!

However, she wasn't in to letting me fuck her or her fuck me. Fine. First time meeting. I get it.

I got totally unclothed and lie on the bed. Hoping she would do the same. My wishes were not realized. She had her breasts overhanging her bra. Staring me in the eye. Just looking at them, then up to her face arroused me like I've never been before. Dark brown nipples. Her areola surrounding them. GORGEOUS to say the least.

So, while standing in front of me, she slid the condom onto my throbbing cock. I was really hoping she was out of "Trojans" but hey, she's a call girl and had the tools of the trade with her. As well, she put one on her amazing dark cock and told me to suck it. It felt so good in my mouth, with the expeption of the rubber on it. Then she pushed me back and started to take my cock in her mouth. She pounded her head up and down on it. It felt good. But! I found it very impersonal. She didn't give head with passion. There was no variety to it. It was quite a sterile experience for me but at least I did it.

So now. I've made up my mind to wait until I meet a TS that wants to have real passion with me. Not an escort! Never again! I seek the corners of the internet HOPING to find "the one". That girl that will share not only her delicious body with me. But also her mind and soul.

And that's my story. Hope it wasn't too long or boring.

Last edited by calgaryshyguy34; 12-25-2009 at 04:10 PM.
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  #11  
Old 12-28-2009
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Ten years from my first sighting until I gained the courage to try my first. I am a confirmed addict now and darn happy.
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  #12  
Old 01-31-2010
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It was about 6 weeks from seeing a "ladyboy" porn dvd. It happened like this! My thai girlfriend introduces me to the delights of the ladyboy. But living in England predjudice and bigotry make it a little bit difficult at first! Yao buys me a copy of the Daily Sport, it claims to be a newspaper. It is in name only!! I open it up and what do I a small add for a "shemale" visiting Newcastle. Yao dials the number for me, and gives me the phone.I wait until a gentle voice starts to describe herself. I"m convinced and book an appointment, for the same day!!!!! Yao smiles and says "you go now, see ladyboy" Well, I arrive at her Hotel, the door opens and there she is a vision of lovliness. Black 4ft 11ins wearing a pretty dress and 6inch heeled ankle strap shoes. FUCK ME! I"m Gizel says she. I"m tongue tied by now. She leads me to the bed and starts to undress, she has not lied. She looks like Kelly Rowland (Destiny"s Child). And wait for it 8inches of fully functioning "she cock" An hour later the encounter was all over! I was knackered and she was 100 pounds better off. We kissed and parted and I remember thinking the sex was fantastic but the kissing really blew my mind!!
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  #13  
Old 01-31-2010
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Go on. Give it a try. One day it may be too late. Believe me you won"t regret it.
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  #14  
Old 02-01-2010
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About a year my New Years resolution that year was I am gonna find out exactly what is going on with all this "shemale stuff" was it just a kink? well about 2 months later a cute little tranny hooker in the front seat of my Trans Am proved it wasnt I never came so hard a mouth I thought it was going to shoot out her nose LOL
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  #15  
Old 02-01-2010
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I also discovered she males in Color Climax magazines, around 1987/8. I think it took me a year to try one escort she male. Since then, sometimes I would be with escort she males. Now I have a TGgirlfriend.
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Quote:
Originally Posted by CortoriaCUM View Post
I must have been 17 or 18 when I first discovered the Color Climax shemale magazines and a hitherto unknown world of pleasure was revealed to me. :-)

Took me up to my first year after college until I actually had sex with a tgirl. Now, I try to hook up with A., a lovely Belgian tgirl in Antwerp at least once a month.

For all the guys here who are still on the fence, do it! It's simply the best sex a guy can get.
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  #16  
Old 09-06-2014
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I've liked them most of my life, though I didn't recognize my attraction until I was an adult. I haven't met one in person, just a couple of online friends. I don't want an escort either.
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  #17  
Old 09-06-2014
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Quote:
Originally Posted by spirit09 View Post
I mean, from the time you started to look at tgirls, how long was it until you actually were with one?

I've been looking online pretty much all the time for about 6 months but I still don't have the courage to meet one(escort)
About 4 months.I wanted to really feel 100% sure because it was a new thrill so after everything was ok in my mind I visited a brothel.

Great experience,she was very kind and really showed me a good time.I was only active at the time but I remember I started sucking her right away and she was surprised at how good I was,hehe.

I told her I never did that before and I remember her answer: "Wait until I fuck you for the first time,you'll want dick in you all the time."
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  #18  
Old 09-19-2014
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That's the only negative thing about my recent move to near Eugene, Oregon from Los Angeles. I'm sure there are not nearly as many transwomen up here as in L.A. or San Francisco. Oh well...
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  #19  
Old 09-20-2014
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Took me about 3-4 years. I was in such anticipation that I came within 30 sec. of penetration
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  #20  
Old 08-04-2015
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Probably a few months after I got hooked watching ts porn. I'm not too exactly sure. I still keep in touch with my 1st. She's a good girl. Not really.
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  #21  
Old 08-04-2015
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If I wasn’t married, probably a long time ago. But I never was looking for a “hookup.” I would like to have met someone for a long term relationship and/or marriage. When I was younger there were at least two possible “missed” opportunities that I could think of, my friend from college, and “Stephanie.” I’ve posted about them elsewhere on TLB.

I wasn’t single for very long between my first and second wives. Maybe my third wife?
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  #22  
Old 08-05-2015
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From first at looking at TS, to a TS = 12 years . . a very long 12 years

But when the time came,
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