Want an an example of a professional challenge I faced recently? Okay, here’s a story for you….
Let me start by saying I don’t do things like this except with people I’ve known for many years, who have repeatedly and convincingly told me that that it would be okay. No, not even just okay – that they would love it if I created a little surprise like this for them. Really, really love it, with no qualms whatsoever. I have had guys beg me for things like this and then freak out when I made it happen, so I rarely do it any more. But this was a special circumstance.
So having established that, on with the story….
A dear man, a friend of some years standing with me, did me a favor recently. We’ll leave out the exact details, but suffice it to say that there was something I needed that would have cost me plenty, and he got it done for me. Lovely man.
Thus I was inspired to do something sweet for him, to show my appreciation. But what? I wondered. Then I recalled that this man, who I will call Bob, had expressed curiosity about pretty transsexual escorts. She-males, as they are sometimes called. I am happy to facilitate fantasies. The problem? I didn’t know any TS sex workers personally.
Sure, I could have just picked an ad out of the back of The Stranger. But you see, I am picky about who I let come to my house, and even more so about who I introduce to my friends. People become my clients partly because I have an excellent reputation. I am not about to sully that by creating a bad experience for them. And having been around the sex industry some years, I have witnessed some vivid examples of just how bad things can be. Not any encounters I ever set up, you understand, but working for other people.
So my fear was me finding a TS escort, arranging for her to come and play with me and my guy, and something goes wrong.
Like she doesn’t show up.
Or she shows up, and she is nothing like her pictures. To mean: she’s ugly as hell.
Or she shows up drunk/stoned off her ass.
Worst case: an ugly chick, with bowed legs and a five-o’clock shadow, shows up, drunk, in a car with three guys who she calls her “security”. And then she proceeds to make a huge screaming scene out in the street when I refuse to let the four of them into the house. (Because I would refuse.)
Those are just a handful of the bad possibilities, and the reason they come so quickly to mind is that I saw all of them happen when I worked for out-call escort services. I always felt bad for the guy whose house it was, but relieved that I could just get out of there quickly before the situation escalated into a Cops episode. It’s tricky enough screening clients, I don’t want to have to sweat screening other sex workers as well. Thus, I do not generally have other ladies I don’t know come play with me and my friends.
But still – it seemed as if a girl like myself should be able to use her resources and find someone nice. Thus, I asked around, I talked to people, I checked references, I studied photos, I emailed. And in the end, I settled on the girl I thought would be best and crossed my fingers. Don’t you boys think I don’t know how you feel when you’re arranging to meet a new lady. It’s nerve-wracking.
As the day approached, I talked to Jae. “I want you to be there. I’m going to be busy playing with him, I want you to let her in, show her the bathroom so she can change, bring her down when she’s ready, and just generally stick close to her. I don’t want a stranger wandering around my house unaccompanied, that makes me uncomfortable. And if anything happens that shouldn't be happening, you contain it and then come get me, fast.”
Jae replied, “Oh, hell yes I’ll be there, I want to see this, it’s going to be hot.”
“That is certainly my fondest hope.”
The appointed day came. Bob knew I had something special in mind, although he didn’t know exactly what. I had him nicely tied to my bondage chair when I heard the doorbell ring.
Okay, she's here. That's good. I hope.
Footsteps, and a murmur of voice - Jae's and another one, female. No sounds of trouble.
Minutes ticked by. The suspense was killing me. I'd told Jae to bring her down when she was ready. Had something gone wrong after all?
I secured the blindfold more snugly over Bob's eyes and said, "I think I'll go see if our guest has everything she needs. Don't go away." A muffled snort of laughter from Bob, who was quite aware he wasn't going anywhere.
I walked upstairs to find Jae sitting on my couch, in an attitude of complete attention, next to... a pretty woman. Young, taller than me, slender, with smooth skin and big doe-like eyes. Oh yes indeed, I thought, this might work out just fine.
Now I knew why Jae hadn't brought her downstairs. Blue-eyed little Jae has a weakness for dark-haired, exotic-looking women. I am well-acquainted with the expression she gets when she's flirting. She was wearing it now. I shot her a glance that clearly said, "This girl is not here for you, missy. You are neglecting your duties." Interpreting it correctly, Jae jumped to her feet. "Oh, hi, Ma'am. Are you ready for us?"
Nice try, Jae, I thought, as I introduced myself to the girl, who I will call Lisa. As Lisa stood up to greet me, I could see why Jae had been chatting her up - she was wearing only a pretty bra, panties and high heels, and she really was quite lovely.
And extremely feminine-looking: she was exquisitely coiffed and made-up, as shaved and waxed and polished as could be, all as flawlessly as a china doll. I wonder where she got that lingerie? I thought, feeling suddenly conscious that I was overdue for a manicure, and that the damp weather was making my hair frizz a bit. She's actually not the first tranny girl I've met who had amazing maquillage skills. As Jae put it later, “I'm a bio-girl, how is it that a chick with a dick can make me feel so butch, and a little scruffy?”
I put thoughts of nail polish aside and talked to Lisa. She was soft-spoken and perhaps a bit shy, but she seemed sweet and pleasant. I could see why she might feel a bit shy. True, she was a professional escort, but this was not your average client situation. I explained to her a little more about Bob, the types of things he and I did together, and what I wanted her to do. She nodded and agreed.
We went downstairs and I presented Bob to her. He was just as fascinated by her as I was. So, to my intense relief and pleasure, the three of us had a very nice time together. I wouldn’t say Lisa is the naturally-dominant type, although hey, with some time and coaching, who knows? She did watch me put needles in Bob’s nipples with cautious curiosity. And she really was quite lovely and sweet, and a charming addition to the scene in other ways.
As she left later, she said, “Call me anytime…” Who knows, perhaps our paths will cross again.