July 1st, 2003

First of all, let me me say sorry for not bringing you guys any new story during the month of June. I took a couple of weeks off to go on my yearly vacation and things happened to me sex wise that went beyond my wildest dreams and which I will be happy to report to you in the next few updates.

I usually try to spend a few days in Miami every year, because I simply love the feeling of open sexuality that this town gives, particularly in South Beach and other areas where the rich and beautiful meet and this year has not been different.

There is such a rich mixture of cultures that I have always found it absolutely impossible to be bored there, and that is without even talking about the tourists avid for sand, beach, sun and of course sex, all four ingredients for ever present in the city that loves! And so this tale of mine starts in Miami, but before you start stroking, let me admit to a fantasy of mine:

Shemale sex! Yes.. It's true. I love the idea of a gorgeous woman with beautiful boobs, a curvy body and a hard cock in between her gorgeous legs.. and if that makes me a depraved and deranged pervert with homosexual tendencies, then so be it! Sex with a shemale has turned me on ever since I discovered shemales even existed back when the Internet started to spread and I have since enjoyed its delicious thrills with the help of willing phone sex partners, but never in real life.

That was before Miami though. On the second night of my stay there, I happened to be drifting from bar to bar in South Beach when I came across a bunch of particularly vociferous people who obviously were having the time of their lives. A couple of the babes in that group were real hot and I was shocked to discover that they were in fact transvestites. Needless to say I got turned on pretty much instantly and followed them for a while, hoping that somehow, one of them would find me irresistible enough to approach me and get the shemale fantasy on the way.

But no such luck, and so I found myself back at the hotel, sporting such a hard on from this encounter and in need of some much sought after sexual release. In normal circumstances, I would have just simply picked up the phone, and dialed a phone sex service for a hot chat but heck, I was on vacation and I found myself dialing an escort agency and booking the services of a shemale.

Now, it didn't go quite that way, for even though a shemale is what I really wanted, I of course did the "macho" think and told the woman at the other end of the phone that I wanted to spend a couple of hours with a beautiful Miami woman. The woman at the agency was a very friendly person and had wonderful phone manners, which helps I suppose in this business. After we had gone through the inevitable "policy setting" discussion, she asked me what kind of "female companion" I was interested in and I supposed my answer must have sounded so uninterested to her that she eventually said that they could also locate a "male companion" if I wanted to.

Eventually, after more probing, she found out that what I really wanted was a shemale and proceeded to tell me there was one available right now, which she was sure would satisfy "every" need I had.

I wanted to make sure she was feminine, had big boobs and also a big "functioning" dick. She assured me she did and so we made the arrangements and a couple of hours later the shemale was in my hotel room.

I can tell you now, that I know what a virgin feels like when she is about to loose her virginity because I felt exactly like that. I was shaking like a leaf, not able to utter any sentence that made any sense, and after I paid her, the shemale (she called herself Bambi) suggested we took a bath.

I remember looking at her whilst she was undressing and the first thing I noticed was her wonderfully round ass. I mean this babe had an arse to die for, and the thought that I was going to be able to plough her later on had me in a frenzy in no time.

After filling the bath with hot water and lots of bath lotion, Bambi proceeded to sit down in the tub and invited me to sit right in front of her, my back pressing against her boobs, which I did.

The feeling of her wonderfully feminine body, together with the bubbles and the hot water was wonderful and I was surprised I could not feel any sign of " a functioning dick" at the small of my back. This kinda put me a ease, don't ask why, and I began to relax as Bambi started to massage my shoulders, back, and then on to my chest muscles which she seemed to fondle for a long time. After a while, and sensing that I was completely relaxed with the whole "shemale" thing, she proceeded to let both her arms wonder towards my stomach and inevitably towards my dick which was by now, as hard as a rock.

In order to reach me there, given that she was behind me, she had to press her body against my back and the pressure of her boobs was so wonderful and familiar that I had to remind myself that the person who was sitting behind me had not been born a female and given the right circumstances could quite easily show me a "sign" of her that was entirely male. Just as in phone sex, the thought of a hard cock attached to a beautiful female body was really exciting and I was looking forward to what was to take place.

When I felt her hand, finally touching my dick, I remember thinking that that was it. I had crossed over from being a wholly heterosexual man to a bisexual one. A page in my adult sexual life had been turned. Was a new, completely new chapter about to unfold? The expectations of the unknown was delightfully scary!

Before she actually started to masturbate me, and during the masturbation, Bambi had kept herself busy biting me on the neck, sometimes softly, sometimes a bit harder, and it dawned on me that this was something I loved to do myself, when making love to a woman. Was the biting thing something inherently male? I didn't know, but it felt delicious. Anyway, Bambi knew what to do with a cock and after a couple of minutes of gentle masturbation, I had a first (I would go on having more than one) violent orgasm.

I supposed shemales deal with first timers all the time and know how to handle them, because somehow, Barmbi knew that after my orgasm, I did not want to be reminded that she was in fact a man with her own dick and stayed there, behind me, not saying a word, and barely touching me whilst I had leaned forward, thinking that by increasing the physical distance between her and I would erase the reality that a shemale was sitting behind me!

A few minutes went by and once more, I felt her hands move against my back, touching it slightly. And with each movement, my mind began to relax again, and I leaned backwards, feeling the warmth of her body against my back.

Once again, she started to massage my shoulders, and then forward around me, towards my chest, and lower until she once again had my dick in one hand whilst the other wondered lower still towards the area below my ball, which is a place I really love touched. Of course, it was not long before I had another erection, and she started to slowly masturbate me.

It felt wonderful. I suppose she knew that I was ready for the next step because she whispered in my ear that perhaps we could switch position, if I wanted, and I did.

Throughout the preceding moments, I had wondered why I had not felt her dick against me and as I got up and turned round to face her, I understood why. She had actually sat down in such a way that she was "sitting" on her dick, making it impossible for me to feel it. But now that she was raising herself up, her dick came to view and whilst it was not hard, I could see that it was quite a big dick and she was indeed well hung.

She could see my stare and seeing as I was not touching it, leaned forward towards me and said: "You are dying for a cock, aren't you?" And I was.

And so we switched position and for the first time in my live I touched a cock that was not mine.. and loved it!

Read what happened next on my next update

Mr. Phone Sex