Submitted by Enchantrix Empire Member, NB:

“If you have read my previous blog entries where I detail the history and evolution of my sexual fantasies and fetishes, I mentioned that I have had some encounters with shemales in the past. The lurid details seemed out of place in that blog, but since I have been thinking about it, I decided to post those here. This is a bit more graphic in nature so feel free to skip this if that wouldn’t interest you 🙂 Again, these are nearly twenty year old memories, and are as honest a recollection as I am able to produce.

I was nervous and embarrassed when I purchased the adult classified newspaper, but the newsstand clerk didn’t bat an eye. Judging by the spread at the newsstand, pornography was probably his most profitable product. Having lived in NYC my whole life, and working in Midtown Manhattan for a number of years, sex shops and pornography on newsstands were not an uncommon sight. However, my life was “sheltered” enough that I rarely if ever saw actual prostitutes or anything like that, despite how NYC is often portrayed in the media. I folded the paper to obscure it as much as possible and stowed it in my backpack, where it would sit undisturbed until I arrived home after work.

I still lived with my parents at the time, but my room was well away from the common areas of the house so I had reasonable privacy. I even had my own phone line, primarily for my computer. These were the pre-Internet days when computer “networks” were done with one computer calling another via a telephone modem at speeds that were so slow you probably can’t even conceive of them if you didn’t live through that era. By way of comparison, the typical voice sample MP3 of a beautiful LDW Mistress that streams instantly today, would probably have taken an nearly hour to download back then :-p

I flipped through the ads for shemale escorts, not really knowing what I wanted or was doing. Pictures were important, albeit in grainy black and white newsprint, as I definitely required someone who looked female. I do not believe I could ever have any kind of intimacy with an actual male. And of course I needed to be able to go and see them… having them come to me was right out. I was young and had a decent job and no bills to speak of, so spending money wasn’t an issue, but even though I was over 18 I hadn’t yet bothered to get a driver’s license. There was nowhere I ever needed to go that would have been more convenient to drive rather than walk or take the subway, except perhaps to the Mall, but my brother drove and took care of that.

I ultimately settled on Brooke. She appeared to be a tall, thin blonde in her picture. The location was a neighborhood I was familiar with, not far from Greenwich Village, and her tagline captured my imagination, which boasted that she had something to offer that was “more precious than gold, and more addictive than any drug.”

After a few false starts, I willed myself to call her on the phone and she answered. I do not recall the exact conversation, but I expressed my interest, and when I mentioned the tagline she laughed and I loved that laugh. I told her I would be there in about an hour as I was taking the subway, and she directed me to a cross street where I should call from a payphone when I was there and then she would give me the address. As an aside, I would later realize that she also used that method to juggle clients to avoid the awkward situation of two “suitors” meeting up at the door as one entered and the other left.

When I arrived at the location, I was surprised as I had actually just been within a block of there a few days before at a fencing school as I had been toying with the idea of fencing lessons. I called her from the payphone and she gave the address, which was a nice enough looking small brick apartment building. She had a ground floor apartment, and after knocking she greeted me at the door, and quickly ushered me inside. She had mentioned the importance of discretion every time I spoke with her and it was pretty clear that she was worried about the neighbors figuring out what was going on and complaining.

The door from the hallway led directly into a small square bedroom. There was another door to the left of the entry that presumably led deeper into the apartment. The room itself was dominated by a queen size bed and a standard cushioned chair. There was a small TV mounted high on the wall in the kind of bracket you might find at a hotel or hospital waiting room, with some shemale porn playing with the sound off.

Brooke ushered me to the chair where I sat down and we engaged in some small talk. She was tall and thin, with very pale skin. Her hair was maybe shoulder length and she had a nice face, but really didn’t have much in the way of feminine curves. She was dressed in a kind of nightgown, with black panties and thigh high stockings. I remember noting that her hands were very big, bigger than my own at least. Another girl came into the room through the other door, and Brooke began doting on her and asking me to agree to how pretty she was. I assume she was also a shemale, and seemed uncomfortable by the praise, or maybe she wasn’t a sex worker… Either way I do recall thinking she was very attractive and wishing I was seeing her instead of Brooke, but as she had somewhere to be, she quickly left, leaving the two of us alone again.

“Business” was conducted quickly, and I gave her money and she told me to get undressed. I started taking off my clothes still in the chair while she sat on the bed. Once I took my underwear off I was at least partly erect, and she brushed her hand on my cock and said “Oh is that for me?” By the time I was fully naked, she was laying prone on the bed, watching the TV, and told me to touch her. I ran my hands up and down her legs, and across the satin panties of her ass, and then I felt it. She encouraged me to continue in that way. Even though the way she was positioned had her crotch down on the bed, her cock was pulled back so that I could touch it through her panties.

I was still nervous as hell, but more excited than anything else since this was my first sexual contact with another person. I am guessing that as a jaded professional, she needed more “warming up” than I did :-p. After a few minutes of that she sat up on the side of the bed and told me to take her panties off. I was too nervous and embarrassed to look her in the eye or at what I was doing as I pulled her panties down to her thighs as she sort of half-stood to let them move. When I stopped there, dropping my hands she again instructed me to take them “all the way off.” I gingerly pulled them down her thighs and legs, sort of sliding to my knees on the floor to reach all the way down as she stepped out of them, kicking them aside.

What happened next is the experience that has been indelibly burned into my brain and fueled nearly twenty years of fantasies. Going from down on my hands and knees after pulling her panties down to ankle level, I instinctively started to raise my upper body back up to a vertical position, when I suddenly felt her hand on my head and then somehow, inexplicably, her cock was in my mouth and I was sucking it.

I have no recollection of opening my mouth, or making any kind of conscious decision at all. It was if she touched me and my brain just shut off and instinct took over, and that instinct was to suck for all I was worth. Naked, obedient, sucking.

If that wasn’t enough, the next thing that happened is also something I have thought about and fantasized about to this day. Her cock had not been in my mouth for very long when I heard the door opened behind me and someone began talking. It was a female voice, but whether it was a woman, a shemale, the redhead I had seen earlier, or someone else entirely, I have no idea. I never saw the person, because I never stopped sucking. Here I was, naked in a strange place, with someone I had never met before, and was suddenly surprised by the appearance of another person, and all I could do was suck. It never even occurred to me to stop, or move, or anything. She could have easily rifled through my clothes, stolen my wallet, or anything. This is easily the type of story that have ended with “…and that is where I woke up naked in a tub of ice missing a kidney.” But was I thinking of any of that at the time? No. My entire world has a hand on my head and a cock in my mouth. Nothing. Else. Mattered.

In fact, Brooke was more surprised and annoyed than I was. I felt her hand tense up on my head and she said something that I don’t remember, but was along the lines of a “What the fuck?” But the tension quickly passed as they both realized that I wasn’t going anywhere. They continued their short conversation, and then the other woman left, and I was still just on my knees, wither her hand on my head, unable to do anything except suck her cock.

Brooke had a large cock. Certainly much bigger than my own and I’d guess it was probably nine inches at least. It was long and straight and thick at the base. The only thing that I didn’t like about it was that the head was narrower than the base. But that may have also been because as a sloppy novice, I wasn’t really able to fully arouse her. As you might imagine, being a sloppy novice it wasn’t long before my face was covered in my own saliva as her cock occasionally escaped, or I began to choke and gag, and spent a few moments running my lips and tongue along the underside like it was a corn cob to recover before again taking it as deep as I could manage.

I don’t know how long I spend sucking her cock, but it probably wasn’t all that long before I was exhausted, and was lying on the bed wondering what would happen next. I recall that I kind of hinted at whether or not she would fuck me, but when I admitted I hadn’t really ever had anything in my ass, she quickly dismissed the notion, and finished me off with a handjob. I have to admit I was disappointed. Not because I had ever really given much thought to anal sex before (or since), but right then and there, in that moment, I wanted her to own me. I wanted to give her everything and I just wanted to be hers. After I came she cleaned me up with a warm moist towel, and I got dressed gave her a tip and went on my way.

That was the first of three encounters I would have with Brooke”