My first experience

[Louis_K]

I plan to post more experiences and these aren't embellished for effect. Just an account. So, I won't try to be flowery etc. Names have been changed in some cases.

The Experience

Let’s start at the beginning. The idea of meeting a passable TS has excited me for a long time. I love women, way too much as my stip club expenditures over the years will attest. However, I just wanted to meet a TS that was passable enough to compete with all the beautiful strippers I had fantasized about getting with over the years. Just to see if it was even possible for me to have the same feeling, the same high I get from being near a beautiful girl. I needed to know.

Pictures were one thing, I know how photoshop works and how amazing some people can make images. So, despite seeing hundreds of extremely passable TS ladies in pictures and even online in chat rooms and porn clips, I really wanted to find out for sure how one would be in person. For the record, I was NOT obsessed with TS porn, I am fairly addicted to porn but TS porn only gets viewed every now and then (usually after a few too many spanks to Yumi, Tia Tanaka or Victoria Sweet clips). I have to admit that Asian Tranny porn and Vaniity often worked just as well as any of the great porn stars I usually gravitate toward.

But enough about Porn, what about really meeting a TS girl? Where would I do it? Sure, living in Atlanta seemed like it wouldn’t be terribly hard to meet one. However, I was reluctant to go to gay bars as I never felt (nor do I still feel) like I was gay or even Bi. I just NEEDED to meet a T-Girl badly. Not just anyone though. Not some guy in a wig and dress with lipstick on…no, she HAD to be hot. Hot enough to make me want her.

So, I scoured the listings I could find as often as I could…at first craigslist, and backpage and later discovering Eros and Adult Search…every day, seeing who was new. Waiting for the perfect girl to appear in an add wanting to meet ME.

Atlanta has a lot of Dominant Black TS girls it seemed. Rarely a white one, and even rarer an Asian one or decent looking Latin Girl to be found. I mean, those are my preferences for real girls why would TS girls be any different right.

I go to Vegas twice a year, maybe I could strike there. The ads seemed to feature more talent that would interest me but my windows are short and my timidity still prevailed even when spotting a few prime candidates. I could NOT pull the trigger.

I didn’t know what I wanted to do once I met them. I didn’t know if I would want to even touch anything other than their great breasts. Or what I’d want them to touch on me if anything. What if they sounded strange? What if you could “see through” their make-up? Too much uncertainty about what would happen. Yet still, I REALLY needed to meet one.

Finally after about 2 years of emailing and backing out, I decided that I would call one finally and try to meet one. So, I looked at backpage on a Tuesday afternoon as I had an opening Tuesday evening where I could disappear for a few hours. The search was a little nerve-wracking…Black TS ads filled up backpage that day with TALL, HUGE TOOLED, DOMINANT girls ready to “give it to me”! Needless to say, I was very intimidated again and thinking about chickening out once again.

Then I stumbled across a visiting Latina named Sophia…her pics were hot (looked like all the pretty latin girls I was obsessed with during college after dating a Costa Rican student and falling hard until she graduated and left the U.S.). Could this be the right one? The ad was softer than most, relaxing, patient with 1st Timers, it seemed…well, very feminine to me. So, I dialed…heart pounding for two, three rings…then she answers, “Hello?” Spanish accent a little timid…she might be as nervous as me. I muster, “Hello, is this Sophia?” She says, “Yes, it is, who is this?” Not ready to reveal a name I get to my point, “I saw an ad in backpage and wanted to know if you were available to meet?”

She says, “Sure, when do you want to meet?” I know I need to hurry before I lose my nerve again, “As soon as possible? I can come now.”

She is taken aback a little, “Oh, well where are you? I need some time.”

I say, “Okay, I’m on the Northside, your add says you’re off Highway 85 at Druid Hills. Is that right?”

“Yes”. I reply with a little confidence, “Okay then, it’ll take me about 20 minutes to get there, will that give you enough time?”

“Yes, that is okay. Call me when you get to the exit and I will tell you where to go.”

Done, I was enroute within seconds. It took me all of 9 minutes to hit the exit. Speed Dialing I get her again, “I’m at the exit, now where do I go?”

“You’re too fast, go to the <omitted> Hotel and wait for me to call you, okay?”

“Okay.” I know just where that is and I park immediately and wait anxiously. Minutes pass. Then more minutes…it’s now 5 minutes past the original 20 and I’m sitting in a hotel parking lot looking suspicious. So I dial again.

“Are you here?” She asks. “Yeah! Been here a while waiting for you to call me”

“Ah, OK, come to Room 424” I was out of my car and inside the hotel faster than a bat out of hell.

I sneak to the elevator (I say sneak but really I just didn’t look at anyone as I stroll through the lobby of the hotel hoping they don’t check for room keys) and get to the 4th Floor where I finally slow down. I hesitate just slightly before knocking. I realize I still don’t know what I plan to do. My first encounter and I’m going to wing it.

The important thing to just see her, is she hot in real life?

I knock. She opens the door and lets me in. She’s wearing a black fishnet bodysuit and a black bra and panty. Her hair is dark and curly, very decent looking woman. I’m impressed.

She has me come in and sit on a bed (there are two in the room). She sits on the other (the Business bed) and tries to be friendly. “How are you?” I say I’m fine, a little nervous. “Why?” I tell her it is my first time with something like this. “Oh, it’s okay, don’t worry.” She asks about the donation and I hand it over.

She gets to it, “So what do you want to do?” I tell her I’m unsure, she has me take off my clothes and she gets right to pulling on my cock. I move to kiss her breasts. She offers them “Yeah, baby, suck these…mmmm” So I enjoy her breasts just like I would any other beautiful woman’s. She eases me down to lay on my back on the bed and she puts a condom on my cock and on hers (which I missed the unveiling of much to my dismay since it’s been a grand build-up of years to this moment and no grand reveal). She sucks my cock a little and then continues to stroke it as she gets up and quickly feeds me hers. I am ever so slightly hesitant but as she thrusts to to my mouth, I know what to do (I have always read stories like this and said, “yeah right?” in the past, but she didn’t have to beg me to put that cock in my mouth pretty quickly). So I sucked a cock for the first time in my life and tried to do it well but the truth was I was stunned and wouldn’t know how to blow someone if my life depended on it. She stopped me, “Not so much spit.” Apparently I was making it sloppy.

After a few minutes I decide what I want to do, “Can I get inside you?”

She looks a little strangely, “You want to fuck me?” “Yeah, can I?”

She sighs and says, “Okay” and motions for me to get up.

She positions me behind her and holds me back as she gets some lube out for her ass. I put it in slowly….but it’s still too fast for her tastes “Ah, slower, do it slow”. So, I try a couple times and finally get it in and start to fuck her ass a little. It must have been only three minutes and she says “Enough, ow!” and takes me out of her. She removes the condom and tells me to clean up. So I go to the bathroom and wipe myself off wondering how I messed up. She brings me back to the bed and puts a fresh condom on me and strokes me again and puts her face near my dick and tries to get me off with some sexy talk. “Ahh, yeah, come for me baby! Come on my face!” Which of course isn’t going to happen with the rubber on but I understand what she wants. Admittedly by this time I’m just ready to get it over with as well and I let her stroking get me off and cum in the rubber.

So, I clean up again and she makes sure I’m okay, “Are you okay?” I guess, has she done enough is implied. I say sure and start to get dressed.

I compliment her on her looks and ask here where she’s from “ Mexico ”. She says I’m different…and I wonder why? “Do most guys want you to fuck them?” “Of course!” She says. Oh well, I guess I’m not ready for Prime Time TS action yet J

I felt a little odd afterwards and I think to myself “Well, you did it. You tried it. You’re just not into it. So, let that be it”.

Of course, that wasn’t it.

[Jwayne06]

Enjoyed your story!

[centillini]

awesome

[luvtrans]

Seems a bit of a let down. But then again most fantasies turn to dust in reality. Trying to recall my first experiences - thankfully mind-blowingly good. I must have been lucky.

[slutolive]

Thanks for sharing that! I am fascinated to hear people's first time experiences; I guess we all have different routes into the TS world.
This is mine:
I was living in Amsterdam, and was (no surprise) fascinated by the famous red light district. I used to wander up and down and just look, having never seen anything quite like it, but rarely had the courage to see a girl- at least, until I developed an increasing fascination for BDSM, and passed one or two windows with an impressive array of cuffs, gags, paddles, whips and other items I couldn't even identify!
I eventually plucked up courage to knock at one of these windows (that's a story for another occasion!), and from then on, whenever I had the chance I would seek out a Dominatrix and try out a succession of fantasies- the most revealing of which turned out to be the strap-on experience: it turned out that as well as a craving for bondage and submission, I loved nothing more than a good hard cock up my arse!
Back then I barely knew of the existence of transsexuals, so my first experience was quite by accident: I went to a very promising looking window with two tall, sexy, strong-looking women against a backdrop of whips, canes and leather restraints. They seemed game for anything and offered me a decent price for a session with both.
Before I knew it I was naked, on my knees having my face slapped and ordered to worship their bodies from the shiny pvc boots up...but before I could discover their secret they hàd me on the bed kissing and sucking the breasts of the dominant partner while the other one watched and gave me the occasional slap.
There was a natural pause- no clock-watching here- and we chatted for a while; they asked me why I liked being dominated, of course not such an easy question! - and I said something vague about loving to worship women, and one of them said "but we are not women" and pulled out an alarmingly large cock- I was transfixed and ecstatic! I took as much as I could in my mouth, then they wanted to fuck me- the first one was too big and despite my best efforts I had to admit defeat, but the other was slightly smaller, and took her time to open me up on my back. Once she was in and able to fuck me properly she started to wank my by now totally rigid cock- I came buckets, I don't think I have ever seen so much come before or since!
After cleaning up and thanking them for a truly unique experience I walked home on a cloud, the erotic possibilities of the future filling my thoughts for many days!
Sadly when I had a chance to return they had gone, but years later I had another totally different but equally wonderful experience which I'll write about another time.
Slut Olive xx

[Louis_K]

Wow. Don't know if I could have rolled with it so easily if I was caught that unaware on my first experience. Thank you for sharing.

-L

[Lib3]

A wise man once said to not judge a book from its cover... and I add (despite I'm not wise at all as I spent years at tarts) to not judge it from first page !
Sex for money is a particular deal, it's matter of personal feeling and attitude of prostitute (girl or t-girl) more than her skills and look imho.
Reading yr story I remember the first time I paid for sex...I was looking for a busty hot blonde woman, as my favorite pornstar of '80s ( the italian actress Moana Pozzi, may her soul rest in peace) going up and down in red light district of my town... when I finally found her ( an hot busty whore, not Moana ofc ) ) my dream of a lustful experience turned into an awkward and perfunctory fuck with false sexy talks in the end to make me cum as fast as possible just because her lazy attitude ... sometimes it happens to find something doesn't worth the money so don't give up, choose carufully yr t-lady as per your liking and as long you are the (tax)payer do what you prefer with her ( I had sex with several tgirls and I never sucked dick nor be fucked... yep... everywhere in the world they are surprised of it as the 85% of their customers love to be bottomed but who cares about statistics ? )
Ciao !
p.s. Sorry for my poor english, I hope you get my point of wiew

[Louis_K]

A wise man once said to not judge a book from its cover... and I add (despite I'm not wise at all as I spent years at tarts) to not judge it from first page !
Sex for money is a particular deal, it's matter of personal feeling and attitude of prostitute (girl or t-girl) more than her skills and look imho.
Reading yr story I remember the first time I paid for sex...I was looking for a busty hot blonde woman, as my favorite pornstar of '80s ( the italian actress Moana Pozzi, may her soul rest in peace) going up and down in red light district of my town... when I finally found her ( an hot busty whore, not Moana ofc ) ) my dream of a lustful experience turned into an awkward and perfunctory fuck with false sexy talks in the end to make me cum as fast as possible just because her lazy attitude ... sometimes it happens to find something doesn't worth the money so don't give up, choose carufully yr t-lady as per your liking and as long you are the (tax)payer do what you prefer with her ( I had sex with several tgirls and I never sucked dick nor be fucked... yep... everywhere in the world they are surprised of it as the 85% of their customers love to be bottomed but who cares about statistics ? )
Ciao !
p.s. Sorry for my poor english, I hope you get my point of wiew

Your English works.

Good observations.

I have had several great experiences since.

Thanks for checking out the story.

-L