The Second Time (now I'm in trouble)

[Louis_K]

THE SECOND TIME (Now I’m in Trouble)

So, I broke the barrier. I had met and been with a pretty TS.

The experience wasn’t terrific and I thought I would likely not be interested in pursuing any more.

So, I went back to GGs for a couple weeks and after a very dull experience with one extremely pretty asian girl I thought back on my 1st experience with a TS…at least it wasn’t boring and dull. At least She was into it and seemed like she wanted to have sex.

So, maybe I wouldn’t close the door on more T-girl experiences. I mean, after all, it was just one time and I really did not know what I was doing or even what I really wanted to do.

So, I go back to the boards and search again.

I see there’s an Asian TS who offers massages. We’ll call her TIFFANY. I email her ad from the board and she sends a nice reply (rare to get one at all) answering my question and encouraging me to call.

Well, I wait and try to schedule a visit on a Thursday evening.

I call, nervous again. She answers, “Hello” I’m thinking to myself that I like her accent, reminds me of a woman who I had wanted to date long ago. “Hello, is this Tiffany?” I say. “Yes, who is this?”.

I explain that I’m Louis who had emailed her about a week prior and that I wanted to know if she was available to meet. “When?” she asks. I say, “Well, now, tonight as soon as you can do it.”

She thinks for a moment, “How about late tonight? I am going to the gym now”. I really needed to have it be early so I say, “Well, maybe another time. How about tomorrow? Can we do it around this time tomorrow?”

She thinks…”Okay, sure.” “Excellent!” I say excitedly. “I’m looking forward to meeting you!”
She has to ask me, “You know I’m TS?”

I can’t quite make out her accent, “What was that?”

She says again, “You know I’m Transexual, right?”

I assure her, “Of course, I definitely know.” “Okay,” She says, “see you tomorrow”.

The next day I get geeked up. Now in the email, she gave me a rate range which I won’t publish but it was put as “between X and Y” and there was a 60% difference between the high and low number. So, I decide to bring the higher amount to insure I get whatever the most interaction available is. I’m committed. However, of course, the ad was for massage service.

So, I call her and get directions to her location. I drive quickly there and of course am 15 minutes earlier than planned.

I call her and she wants me to wait for a few more minutes.

Finally, she says to come on in.

I get in and am pleased to find her in a silk nightgown and she has me relax for a few minutes.

We do some small talk and then she takes me upstairs for a massage. I haven’t given her the donation as yet and she has me strip to my boxers and lie down on the massage table.

Okay, so this is really a massage.

And yeah, she massages me for quite a while. A real one. I don’t let it work as well as it probably should have because I’m still really nervous.

So, after a long massage she asks me what I want to do.

At this point, I have to say that I’m still a little unsure of the nature of my fascination so I figure she’s been so nice and spent so much time already that I’m game to whatever she’s comfortable doing.

So I ask her, “What do you want to do?”

“I don’t know,” she says.

I am insistent, “What do you like doing? I want to do what you like.”

She says, “I want to do what you want.”

I explain that I’m so new I just want to try what she’s comfortable with.

She says, “Did you bring the donation?”

I say, “Sure, you said between X and Y so I figured I better bring Y so we can do the most!”

All this conversation is easy and I have her laughing. I’m totally digging this.

“No intercourse,” she says.

Hey, I gave her the option to do whatever, so I can’t complain.

“Okay, that’s fine,” I say.

So, she takes the donation back to her room and comes back into the massage room without her nightgown on. Wow. What a hot body she has. She’s still wearing pink panties and she looks freakin’ awesome. So she sits down again and we touch each other a little on our upper bodies. I caress her breasts and shoulders and then kiss her shoulders.

She gets up and takes her panties off…and there it is. A nice cock, decent size and semi-hard. Looks slightly smaller than mine. That’s okay.

She leads me into the bedroom.

I kiss her neck and admire her in the mirror. “My god you are gorgeous!” I say.

I kiss her breasts more and her neck and caress her whole body.

She takes off my boxers finally and pulls on my cock which has been hard for a few minutes but now ridiculously hard.

“You have a big cock,” She says. “No I don’t,” I say. I really don’t compared to the porn I watch. She pulls my cock toward her. We’re both still standing and facing each other.

I pull her cock toward me and rub mine against hers. At this point, I am completely excited. I mean, extremely excited. How could I think before that I’d be done with this?

I turn her around again with her back to me and admire her in the mirror again and I’m stroking her cock. I tell her how hot she is, how amazing she looks. I can’t stop myself from kissing her shoulders and neck.

She fondles my cock with her hand behind her, it’s not going anywhere, it’s going to stay hard for some time.

“Do you want to fuck me?” She asks.
“Oh yeah, I want to fuck you baby!,” I reply nearly out of breath from my excitement.

She talks about how big I am again and how she has to figure out how she’s going to take it. If this is just her game, it works very well. I feel like a stud at this point.

She tells me to lay down on the bed. That she’s going to get on top.

I of course comply with her wishes. She gets the condom out and lubes it up very thoroughly. What adds to the excitement is that she had said “No intercourse” only 10 minutes earlier…and now she’s about to hop on my cock. It felt so natural, like we just really dug each other and NEEDED to fuck. That’s what made it so hot.

So, she gets on top of me and she’s a little tight if I have to be honest. She rides me and it feels fantastic. I stroke her cock as she rides me.

Man, the sex is awesome! I am feeling too good to continue stroke her cock. I just attempt to keep myself from cumming as long as possible.

So, she starts stroking her own cock now and her moaning got more intense and louder. I’m barely containing myself at this point.

“Ohh!”, she shouts as she cums all over my stomach.

I’m amazed that I haven’t cum yet. But, she’s ready for it.

“Come on, Baby!” She says to me seductively. “Come on, cum inside me baby!”

I grab her hips and thrust harder and harder, I’m having the best sex I’ve had in years.

After a few more pumps I cum inside her and she lays down on top of me and we embrace.

I kiss her neck some more and she gets off me and goes to clean me up.

DAMN! Amazing!

I get cleaned off and put my boxers back on. I put my pants back on and walk into the hallway and peek in on her in the bathroom where she’s brushing her hair.

“Stop looking at me,” she says playfully, “I’ll melt!”

“But I like looking at you,” I offer.

I stare for a little while longer and then return to get my shirt and jacket.

She dresses again in her silk nightgown and walks me down the stairs.
“That was great.” I tell her.

She smiles and kisses me before opening the door.

I leave on a high, a serious high.

I think to myself, Damn! That was incredible. I have to do that again.

----Post script. I asked Tiffany out, and we saw each other a few times without massages. I would come over and just watch television with her as she laid her head in my lap while we talked. We’d kiss when I left and I thought we’d soon be an item. I won’t be specific but due to circumstances prior to our meeting, she decided that she wouldn’t be my girlfriend. I’ll leave it at that. I hope to change her mind some day, we’ll see…-----

However, the fact that I wasn’t able to land my beautiful TS Tiffany did not stop my yearning to have more experiences.

[squirtsilly]

Wow, that was a great story of what sounds like a terrific encounter. Thanks for sharing it with us, Louis_K.

[Louis_K]

Wow, that was a great story of what sounds like a terrific encounter. Thanks for sharing it with us, Louis_K.

It was awesome. Thanks for reading and the comment.

-Louis

[heyboyheygirl69@gmail.com]

mmmmm i really enjoyed that! good story teller louis!

[Louis_K]

mmmmm i really enjoyed that! good story teller louis!

Thanks, glad you enjoyed it. Hope to post more soon.

Louis

[toelvr]

I found your story very inspiring. Ihavent taken the plunge. the idea of having to pay for company puts me off. not that im such a prize but I like romance and at the least friendship. I hope things work out for you and if not I wish you all the best.

[karmakilla]

damn i want to have a story like this one

[Louis_K]

I found your story very inspiring. Ihavent taken the plunge. the idea of having to pay for company puts me off. not that im such a prize but I like romance and at the least friendship. I hope things work out for you and if not I wish you all the best.

Well. I went to have an experience. That's how I look at it.

Thanks for the comment.

Louis

[Louis_K]

damn i want to have a story like this one

You can do it!

Thanks for the comment,

Louis