How nervous were you?

[wildman]

Was thinking the other day of my first time with a TS last May. After a year of reading reviews, looking at photo after photo, daydreaming continuously on whether or not, it was time to take the plunge. Couldn't bear to call, so took the chicken way out and decided to sent an email. Asked a few questions incl.what would be the best time to call next day. Very nice reply, call next day was just as easy, sweet extremely friendly voice.

One of the longest evenings and nights I can remember. For a 10:00 am session, up at 5am grooming and pacing for hours. Got in the car, tough to concentrate on the road and got to address some 40 minutes ahead of schedule. Sat there like a zombie wondering every couple of minutes about cancelling. 9:57, too late to cancel.

Shaky legs got me to the door, rang the doorbell. The beautiful Shyla and that wondrous smile welcomed me, doomed, the addiction had begun!

I brought a gift but decided to give it only if session was perfect: She got the gift.

[the_conqueror]

Sounds similar to my first time.

I joined this site and did all the research I could. I was amazed at all the different names some of the girls would use, so I admit I was a little confused at times. I decided to narrow it down to the ladies that just used one name lol. I then looked at every picture I could find of them and then read every review on them. After a while I picked Lucy. I wont lie, it was all based on looks

I find calling them, talking for the first time and setting up the meeting is the hardest part so I sent an email. Unfortunately she replied back and told me to call her. I called her the next morning and I think we decided to meet sometime after lunch. I felt somewhat calm after that but then I thought shit, do I bring a gift? how do I give her the money? what do I say?

Anyway, after a long couple hours (and there were a couple times when I almost backed out) it was time to meet. I got to her place but it's kinda fuzzy in my mind on what happened next lol. I don't remember where I parked or how I got up to her apartment but I did. What I do remember is the lingerie she was wearing when she opened the door.

So from the time I picked up the phone to call her to the time I got to her door I was a nervous wreck.

[jaykersh]

My first was similar to wildman. After years of adoring these girls online, I finally had to take the next stop after seeing pics of Layla. That first phone call was brutal. It took me a while just to work up the nerve to dial. It must have been awkward for her 'cause I could barely talk. I was like a pubescent boy asking the prettiest girl in school to the prom. I had a whole list of questions laid out but couldn't utter any of them. We finally managed to set up a time the next day and there I was, past the point of no return. Barring an act of God, I wasn't missing or backing out of my visit.
The nerves continued of course. Didn't sleep much that night. The morning grooming and prep took a while. I had to make sure I was ready and able to leave a great first impression on Layla. I arrived extra early and sat outside a Tim Hortons full of excitement, nervousness and probably a bit of nausea. I'd never done anything like this before. The time finally arrived, I took a few deep breaths, and knocked on her door. The rest, as they say, is history.
On a side note, the next morning I had a job interview that I nailed. Had anyone asked how I prepared for it the night before, I would have had to say, "by getting fucked by that sexy Layla's wonderful cock."

[aguyoutthere1]

Great thread, my first time was a date with a Tgirl that was passable. Sitting having dinner I could hardly believe she had a cock. I had no idea what I wanted to do or if I even could do anything. So after we ate, still at our table I said what would you like to do now. She said, "I want to take you home and fuck your brains out". Check please. Got to her place, she slams the door, pushes me to my knees, lifts her skirt and pops out her 5" hard cock. " suck my fucking cock!" She says and I was hooked. She definitely fucked my brains out too. Perfect size for my virgin ass.

Thanks for sharing guys


KC

[hercules09]

My first time was the year 2000 but I had been fantasizing about it since the first time I saw a transsexual in the back of a hustler magazine (maybe late 80s). It took a while to get up the courage to call the first time. The girl was not very good and I would say the experience was pretty bad. However, I was committed to not judging until I had a good experience.

My second experience was better. The girl was nice but the apartment was pretty run down and she was not that attractive - but a great attitude.

My third experience was with Solaya in Vancouver - jackpot! This was what it was all about. Fantastic looking, friendly, uber sexy, great attitude and service.

Since then I have been pretty good at choosing top tier providers. The technology has improved as well (review boards, web-sites, etc.).

[sector7]

I was terrified, but after years of watching porn and fantasizing about the ads in the back of EYE Magazine (because everyone knows EYE had a better shemale escort section then NOW)
I was finally downtown one day by myself, I had just won a poker tournament and had $600 in my pocket and said fuck it, lets make it happen now!
I went for the obvious (https://www.shemalecanada.com/escort/tsmonica/) blond, big ass, big tits.
She mostly lived up to the pics, I was nervous as shit, and she was rushing a little more than I would have preferred.
Not to mention the adrenaline and fear were battling my horniness and excitement and I really only managed a semi-hardon the whole time
but I did get in most the things I really wanted to try:

- Sucking cock (I wasprobably was terrible at it)
- Eating ass (and she had a big brazilian ass and it was delicious!)
- Getting fucked (way more painful than I thought but I was determined to see it through)
- Fucking her ass (even though I was semi hard at best)

I wasn't sure if I was going to cum, but she was patient with me and gave me some extra time
to jerk off while squeezing her juicy ass. All in all it was a successful night and only encouraged me to explore further.

To this day though I still get nervous making that first phone call, but I have had some truly fantastic experiences ....and a couple terrible ones, but I don't let them get me down.

[bb420]

My very first session i had was a duo with 2 female escorts. I'm into anal play, and brought some toys to the party.
They put a toy in my ass and pretty much just jerked me as fast as possible, making me cum in less the 5 minutes. Right after that, they just started getting dressed and checking their phones, I took the hint and thought ".....ok, so i guess we're done here", And left.
At the time, I didn't know any better and I just thought that was the norm for these kinds of things(lol soooo wrong).

Luckily for me, it's not like that.
I've had some amazing sessions with other female and shemale escorts, making me realize just how lame that first session was.

Anyways... When I did have my first time with a shemale, I was more eager then nervous.
The hardest part is initiating the first contact, but after seeing a few female escorts beforehand, I didn't really have any pre-game jitters.

[ilikebootee]

My first few times attempting to meet T-girls didn't work out well. But it wasn't on my part because they just happened to be fraudulent, nonpassable, poor excuses for what I really wanted I wanted a true Tgirl not a man with a wig and a stuffed bra. I finally found a truly beautiful and passable Tgirl in a neighboring town, Who went by the name of Veronica I called first was greeted by a soft sensual pleasant voice with a beautiful accent. Veronica was a Puerto Rican bombshell 5ft 5in, about 125lbs, 36dd breast and one of the greatest asses I've ever seen. I was very nervous at first and not entirely sure i would be able to perform to tell the truth, but she put me at ease with her erotic voice and soft body. The first thing she did was put her breast in my mouth and told me to suck and bite her nipples. I thought i would bit too hard but she urged me to bite harder and that's when i felt her 7.5 inches press against me and by my reaction I knew performing for this beautiful creature would a non issue. We spent a few hours pleasing each other. The best thing about it was the way she anticipated my wants and needs.

[Mayday Malone]

Thanks for sharing your experiences. It's reassuring to know that "vets" like yourselves have gone through a similar rollercoaster of emotions that I am going through as I prepare for my first experience with one of these beautiful ladies (hopefully with Layla Legendz in the next week or two!).
I have been fantasizing about this for years and as I get to the edge of the board, ready to dive in, it is good to know that my hesitation is normal and uneccessary.
Also comforting is that I have had some very minimal email exchange with a couple of girls here and they couldn't have been any sweeter in their responses. If getting downtown T.O. was something I could do more easily and often, I would have already visited the beautiful Lucy and Suzy Hung. They're on my must see list for whenever I can get out of the sticks and find myself there.

[aguyoutthere1]

Thanks for sharing your experiences. It's reassuring to know that "vets" like yourselves have gone through a similar rollercoaster of emotions that I am going through as I prepare for my first experience with one of these beautiful ladies (hopefully with Layla Legendz in the next week or two!).
I have been fantasizing about this for years and as I get to the edge of the board, ready to dive in, it is good to know that my hesitation is normal and uneccessary.
Also comforting is that I have had some very minimal email exchange with a couple of girls here and they couldn't have been any sweeter in their responses. If getting downtown T.O. was something I could do more easily and often, I would have already visited the beautiful Lucy and Suzy Hung. They're on my must see list for whenever I can get out of the sticks and find myself there.

Mayday, you certainly have some excellent choices moving forward. May I also suggest Lola, you can't go wrong there either.

Good luck, and please let us know how your encounters go. Love to here more about Layla.


KC

[Mayday Malone]

Mayday, you certainly have some excellent choices moving forward. May I also suggest Lola, you can't go wrong there either.

Good luck, and please let us know how your encounters go. Love to here more about Layla.


KC

Thanks KC!