First trannies

Let´s move a bit ahead on time. By now I'm in my early thirties in a new city and
with a new job. With the new job came a good salary and that allowed me to expand
my 'posibilities'...

Being in a new city I didn't know anybody to go out with and due to my new job as manager
for a small company couldn't fraternize with the employees, most of them were women by
the way.

So I started going to a nice local night club where you could invite girls to drinks in exchange
of some company (no sex involved). There were stripping shows every night at midnight and
I would just stare at those beautiful girls that most of the time would be wearing sexy lingerie
and would end up naked after slowly stripping. What a dream!

At the same time I'd be renting movies again to be able to masturbate while viewing them.
I also got new toys and bought my first lingerie: some cheap black fishnets pantyhose and
black g-string.

I'd get on all fours while wearing my fishnets and watching porn movies on my laptop. I'd
fantasize about getting fucked using my dildo but it was just that, fantasize. I was never
able to put the damn thing in my ass. It'd just hurt, and pain is no fun. I'd slap my rear with
dildo and that surely was erotic enough to get over the edge and come all over the sheets.

At some point I started to look on local adds for tranny escorts. I found one add and one night
I went to apt. where this trannie lived. You can imagine, dark lighting, nice parfume on the air
and this gorgeus black shemale. She had long hair, long legs and beautiful face. Maybe it was
the ambiance, maybe it was the drinks I had before but that's how I remembered it, just perfect.

She was wearing matching black bra and thong, along some black pumps. We did some talking
as I just can't engage in any sexual activity with some chit chat before. I'm just too shy.

So after telling her about my situation she promised to be gentle with me. She removed her
thong and wow what a magnificent cock! I started to suck it and after some sucking I laid
on my back waiting for my 1st tranny cock. No use, it just hurt. I couldn't relaz enough. I even
tried putting my self on top, sitting on her cock and trying that way to control how it went in.
Same, no use.

And that's pretty much my first try. I was not going to give up on this fantasy of mine. Sooner
or later I'd have a cock in my ass and enjoy every minute of it, but not that night...