Can you believe it?  Silver Fox had the nerve to ask me to jerk myself off the last two times he was here.  He actually got tired of blowing me and just wanted to see me cum.  The first time he asked I complied but this second time I drew my line in the sand.  There are limits, people!  I mean, I may take money for sex but there are sacred rules to giving a blowjob – there are decency standards, you know?  You can’t just abruptly end a blowjob and ask the tranny to jerk herself off! 

WTF?! 

What, just because you’re paying me means you get to tell me how you want the session to play out?  I don’t think so, mister!  How can you call yourself my “sex slave,” my “sex toy,” when you’re going to get tired after blowing me for a mere ten minutes?  A good sex slave finishes off her mistress — he blows her to completion.  You got that, Silver Fox?

Furthermore, I’m bending over backwards to accommodate his fantasies.  He’s been trying to get another Tgirl into the mix forever.  He has placed multiple ads on Craigslist advertising himself as my submissive “boyfriend” and that we’re looking for another CD/TV  to use him. 

I tell him I’m cool with whatever he wants as long as I’m the one getting blown. 

This last time I asked him (after he blew me to completion) how his luck was with the 3way fantasy.  Silver Fox said, “I guess it will have to stay a fantasy.”  It’s been very hard for him to find a willing CD/TV Top. 

And then he asked me, “how do you feel if we got a guy in here instead of a tranny?”

I was like, do you really need to ask that?  Of course I’d prefer a GUY!  I only agreed to play with another TV as a favor to you, my most frequent flier! 

And then he says to me, with all seriousness, ever so matter-of-factly, as if it’s the most normal request in the world: Well, I guess then you’ll have to get me a wig and dress me up as a TV to blow that guy.

I looked at him. Mr. Silver Fox.  A head full of salt and pepper.  Slightly hanging jowl.  The droopy, hang dog eyes.  Wrinkles befitting his age.  But, what the heck, really, if crossdressing is what it takes for him to suck a guy, he’ll do it.  Never mind what he might actually look like.

I looked at him, and I’m just like, what planet are you from? 

At times I wonder if it’s like this for all my customers?  Secretly you guys would all love to be the crossdressing cocksucker/slut/bottom.  Without any realistic expectation of how you’ll look.  Wait, let me change that: you love to be the crossdresser, regardless of how you look.  It’s just a wig and heels, right?

I’m thinking of Don Draper and his 70’s rocker Spinal Tap look.  And he wants to work the streets of the SF Tenderloin.  Here I go again on my own, going down the only road alley I’ve ever known…

I have this other client, a former US Navy SEAL, who also dresses up.  He’s quite good looking as a guy.  But as a girl?  He looks like a cross between Pippi Longstocking and Raggedy Ann.  I think he may have bought the entire look from a Halloween costume store.  And now “she’s” inviting guys over to fuck her.  But each time after she has one of those guys over, she ends up coming to see me.  I never really pried and asked her how it went.  But obviously an itch was left unscratched.

Of course, now Silver Fox wants to get in on the act.  Because, apparently, looking at his salt and pepper hair, there must be a niche for Granny Trannies. 

Of course, it’s not even discussed that he would ever suck off another guy as a guy.  Despite the fact that it would makes things a lot easier: he’s a good looking older guy – a lot more attractive than he would be as a tranny.  But I get it: someone in the equation must be crossdressed.  And if he’s not the guy sucking off a crossdresser then he wants to be the crossdresser doing the sucking.  I can’t decide if this is the ultimate upholding of the heterosexual paradigm (it can’t be two guys!) or a very subversive dismantling of it.

I’ll tell you this, though: the wonders never cease with my customers.  In moments of startling sobriety I realize that when I get my eventual book deal it won’t be about me!  It’ll be about all of you.  Doesn’t it seem like the tranny chasers are so much more “out there” than the trannies?

Nevertheless, because Silver Fox pays so well, so consistently, and so frequently, I shall oblige his nightmare fantasy.  Silver Fox will put an ad out for two CD’s: one top, one submissive.  ”We” will be looking for another CD, TV, or regular guy so the submissive CD can suck us both off.  Like I told Silver Fox, I’m fine with whatever he wants as long as I don’t have to blow anyone. 

And, of course, as long as someone’s blowing me. 

Look for it:

Cassandra and Granny Tranny, coming soon to a CraigsList near you.

Tags: followup