Guess what, you guys?

I saw Dan Savage, Savage Love himself, in the lobby of my hotel in Portland!!! 

It was like meeting the patron saint of prostitutes.  I wanted to run up to him and scream, OhMyGod is it really you, Mr. Savage? I read your advice column religiously!  You are sooo right on!  And guess what?  I’m a crossdressing prostitute!  I know you call girls like me “Sex Workers” but I much prefer the grittiness of the term PROSTITUTE!  I keep it real!  In fact, I have a customer coming this afternoon!  Wanna go meet him?  Can we be best friends?  I’m your biggest fan!

Mr. Savage caught me do a double take.   I managed to get out a dorky and awkward little “Hi, are you Mr. Savage?”  He graciously acknowledged me with a nod of his head and then went on his way…

Phheeeew…  Aren’t you glad my stunted response prevented me from making a real ass out of myself?  But it was a good omen of sorts, wouldn’t you say?  Just as I was a reader of Savage Love meeting my idolized writer, Cassandra was about to have her very first date with a reader off her blog!

He was a huffer.  And a puffer.  He took short, quick, deep breaths through his mouth as I pounded him.  It was very Lamaze-like.  He wasn’t a talker but his heavy and laborious breathing left no confusion how much he was enjoying it.  I had him doggy style and when his face wasn’t buried in the sheets I could see he was beet red with excitement.  His hands gripped the sheets so tightly and he panted like an animal being slaughtered.

It was hot.  I love fucking guys doggy style.  There’s so much more of a raw, animalistic energy.  He was a very stout guy, with strong arms and legs.  Cassandra is a tall Tgirl.  With slender guys I sometimes find myself holding back because I don’t want to crush them or break them.  But Stout Man?  No Problem.  No matter how hard I pounded him, how much of my body weight I slammed into him, his knees and elbows propped him up so he could take more. 

It was a pretty good pounding, wouldn’t you say, Mister Stout Man?  If you lived in SF you can be a regular.  I had a great time with you.  Thanks for being such a classy gentleman.

After Stout Man came (with my cock in his mouth) he asked me, “where’s Hank – did you send him away so you can do business?”

It made me laugh.

Then Stout Man told me not to gamble away the money he just paid me.  No more Lose River for me, I assured him.  It’s flattering (and a bit weird) (yet ultimately very satisfying for my unabashed narcissism) to have sex with someone who reads my writings.  I thanked Stout Man for reading.  He said he enjoyed my blog.

Stout Man was a really nice guy.  He wanted me to cum but I told him that I had one, possibly two more tricks after him.  Can you believe Hank allowed me just one day of work in Portland?  Whatever Benjamins I didn’t pick up on this particular day would go to another tranny hooker. … so sad, I know.

After a quick shower and a change of clothes (Cassandra may be a money-hungry ho but she has some etiquette) I opened the door to my next client.  He was a trick I met off CraigsList Portland, under the casual encounter section.  I didn’t want to post under Adult Services in a new and foreign city.  Too scary: being busted for prostitution would definitely put a damper on my road trip. 

Plus, Hank would *kill* me. 

Looking for paying clients under casual encounters may be a tad un-kosher, I know, but I look at it as asking for general courtship expenses, up front.   Think of it as what you would normally spend wining and dining a girl — with just the hope that you’ll get laid.  The difference with me is that we skip all the unnecessary courtship rituals and get straight to the hot, sweaty, ass-pounding sex. 

Here’s a secret, guys: when a new, fairly decent-looking Tgirl posts under casual encounters, she gets a ton of responses.  In San Francisco back when I still posted under casual encounters I got around 150 to 200 responses over night.  In Portland (a much smaller city) I got roughly 30 responses. 

Have you ever responded to a TGirl casual encounters ad and wondered why she never wrote back?  It’s because the ratio is against you.  You may be thinking to yourself: I’m a good looking guy.  In real life a girl like that would be lucky to land a guy like me.  But in cyberspace it’s different.  Inside the anonymous confidentiality of their homes, TONS of guys are trawling around for Tgirls.  Did you think you were the only one?  You’re easily up against 30, 40, 100, 200 guys.  And there are some REALLY hot guys sniffing around cyber space for Tgirls (or, at the very least, they send pretty hot pics).  I don’t even respond to those anymore because, after a while, there’s too many cute/handsome guys.  It becomes a blur.  Plus, it’s too much of an effort to go back 50 emails to find the one that struck me. 

And if you send those one or two sentence responses, with no pics attached?  Forget about it.  Only the most inexperienced or the most unattractive Tgirls bother with those.  I don’t even save those replies. 

DELETE!

The guys who really want it to happen – they make it happen.  They start with the flatteries.  Then they talk about what they can bring, whether it’s 420, liquors, or the more serious drugs.  Sometimes they come right out and say they’re “generous.”

The guy I chose simply wrote:

Hi – just saw your ad – and I really hope that you choose me to be your bottom boy.  I am 6’1, 185lbs, very athletic (not an ounce of fat), smooth – and ddf – and also willing to totally submit to you. I can bring you whatever u want/ask. I am serious about doing “anything” to please you.

He followed up that email with:

p.s: Just tell me what need to bring – I’m sure that I can oblige.

I asked him if he could help out with some funds for my wardrobe.  Not a problem, he said. 

Ooops, I’m already at a thousand words.  Write all about the sex tomorrow, I promise.

Tags: followup