Third Time not exactly the charm

The Third Times not exactly the Charm…



Okay, been a while since I posted a story and have had several more experiences since then so I need to catch up because I can’t wait to relive through the re-telling some of the more recent encounters…but first back to my earlier experiences.



After having at tremendous 2nd experience but ultimately NOT getting to sustain a relationship with a beautiful TS…I was back to looking online for single serving companions.



A little about my searches since you never know who might be posting on BP or other sites or how real the photos are going to be.



I really am drawn to Asians and Latina women the most which makes it a little difficult in my city where the majority of the TS talent is black and seemingly all Dominant by the way the postings read.



I circled several for a while and again tried to get communication going via email which proves extremely unsuccessful 95% of the time. So, it becomes a hunch on who might fit the bill.



I had seen adds from a blond exotic looking TS who had a Latin-ish name and billed herself as being a Cali girl.



So, I call and get the details…my first clue should have been the rate. It was about half of what I paid my first time and about 2/3 of my second experience which itself was already lower than my first. So, I should have known something was amiss but I just hoped I was getting a good bargain.



I arrived at her apartment and get buzzed inside the gate. She wants me to wait a couple minutes before coming to her door. So, I get that nervous “should I even be here” feeling again.



So, after a few minutes she calls me and tells me to come in. So, I do.

Well, the pictures were definitely misleading. She appeared to be a blond Asian or Hispanic chick in the photos (they weren’t close ups and weren’t large) but she turned out to be a light-skinned black TS…Not unattractive but still a slight letdown in my mind.



She takes me to the bedroom and immediately kisses me on the lips (oh, okay kinda nice) and pulls my pants and underwear down quickly taking my cock into her mouth before asking me anything. She explains that she just wants me to be comfortable.



After a few minutes, she asks for the donation which I provide.

Then the dreaded question of what I want to do comes up. I’m still not too sure of what my goals are, I just want to find out. So, I say I want to play with her a little and then she should play with me.



So, she takes off her lingerie and reveals a thin but decent body (very lacking in the breast department truth be told which is okay on a real girl but takes away from the t-girl experience in my opinion) with a HUGE cock. I mean, really, very BIG…embarrassing to be around when your just average.



So, I start to suck it and give the old college try. I even force it down my throat a little to get all the deep throat action I can stand going. So, she positions herself into Sixty-Nine position and we enjoy mutual blowjobs for a few minutes.



So, this is the time I usually like to fuck, so I ask (always ask), “Can I get inside you now?”



She says, “Sorry baby, I don’t do that on my Half Hour Rate.” Well, that would have been nice to know as I could’ve brought more if I’d known.



“Really?” I say. “Uh, huh.” She says.



Well, I have more cash in the car but I’m butt naked with a hard cock and sucking an extremely LARGE Hard Cock…so, I guess I don’t get to fuck today.



I take my cock away for a minute and concentrate on sucking hers more. I decide to be as thorough as I can stand to be. It starts to occur to me that this isn’t really my favorite thing. I like it a little but it gets a little boring after a while.



So I ask her to suck mine again but this time I stay up on my knees and have her lean down to my cock (most times they lay me back and suck on my cock while I’m laying on my back) which is kind of a nice change of pace.



I get into and grab her head and face fuck her pretty rigorously until I come.



So, that was the end of that experience.

I again have these thoughts of doubting whether the TS thing is at all for me. I mean, maybe I just fell for the girl in my second experience (remember we called her TIFFANY; side note I just emailed her this week trying to see if she’ll go out with me again for real…no luck as yet) and she’s the exception to the rule. I mean, I still LOVE women and see them on a regular basis.



So, I made another bet that I was done with TS experiences for good again unless I could somehow meet one as Amazing as say…VANIITY! I told myself I could probably make an exception for the likes of her.



Of course, reading the beginning of this you know I’d be back, again and again…stay tuned for more real adventures.

Louis K

Reminds me of a combination of my 2nd and 3rd experience. My 2nd experience had false pics, was cheaper than my first TS (which was my best experience so far), wasn't as feminine as her false pics, had a pretty big tool, a small bust, and pulled a "if you want more, you gotta pay more." attitude. My 3rd was the worst by far (CD) and as soon as I walked in, was greeted with a deep kiss, took off my pants immediately, and started me off with a BJ. Anyway, after that 3rd time, I thought I was done too and while it's been some time since I've gone back to TS hunting (about 6-7), I've started looking again recently. Good luck.

6-7 weeks*

Damn, sorry to hear that. Do most people start off their TG adventures with pro girls or TG's that work reg jobs and then graduate to pro girls when they wanna try bottoming?

Looking for sexual excitement on Backpage is like playing with a revolver loaded with one blank.