Shemale Becomes Friend

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A complicated relationship only gets more complicated.
1.4k words
4.38
86.2k
97

Part 1 of the 5 part series

Updated 10/31/2022
Created 11/27/2012
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Last month I was working a dating site with little satisfactory results when I finally got a response from a girl. She was 6 feet tall and blonde. She seemed to have a nice figure and seemed very very athletic. I played basketball in high school and am pretty trim, although all I do nowadays, as an adult in my 20s, is go for runs on the weekend. Still, I love an athletic girl. And who doesn't love a 6 foot tall blonde. Sweet.

We corresponded back and forth with two emails and she seemed excited to talk with me.

She wrote, "You are just my type! But you need to be aware of the fact that I'm a transsexual. I hope that's not a problem. I'm an awesome girlfriend."

I was a bit disappointed because I was looking forward to trying to build a relationship that could result in children. I'm a little bit traditional. And she was proposing what I viewed as a long term lifestyle change.

So, I wrote to her a white lie, "Sorry, last night I had an awesome date with another girl and now I am going to focus on making the most of it. So I'm off the market."

She responded, "Really? I need to know the truth."

I said, "Yup, for real."

She followed up and said, "That's understandable. Good luck with that. But, we both did say we need a running partner, so if you want, we can go for a run."

That sounded reasonable. I didn't really need a running partner, but, I saw no harm in a run.

We met by the park. She was dressed in a track suit. Looked fine. No one stared. No drama. We completed the circle. She kept the pace up.

She asked, "You want to go to the cafe?"

I said, "Sure."

We ate. She seemed pretty cool. She touched me once or twice with her very long fingers on my arms and back. Just like any other girl. I was originally a little afraid that she'd embarrass, me, but not anymore. She was cool.

We ran like this every week and it turned out to be a good thing and we were becoming friends.

Then one week she called and asked, "I have to meet someone after our run. A date. Because you are closer to the park, I was hoping I could bring some stuff and change at your place."

I was very conservative. And didn't want my neighbors seeing a transsexual visiting me in my apartment. But, I thought about it and realized that I didn't want to give in to the negativity about other people's lifestyles or be afraid of my stupid neighbors. I said, "Sure."

We finished the run and then she came up and said, "Nice place!"

"Thanks."

"Where's the bathroom and shower?"

I took her to it and she took a long shower. Then the water went off and she asked, "Do you have a towel for me? I'm all wet."

"Oh sorry, yeah, of course." And I went to find a clean towel for her.

She opened up the door and said, "Thanks."

She didn't just stick her hand out. She stood naked in front of me by the bathroom to take the towel. And she saw that I was a bit surprised and she started smiling.

"Max, you are such a prude."

"No, I'm not."

"Then why did your face turn red as soon as I opened my door to get the towel?"

I was meanwhile trying my very best to look at her face and not look at her chest or down below. Although with my peripheral vision, I could already sense her penis. And I thought it might be rather large but I couldn't see for sure. She didn't seem to have implants or take hormones based upon her chest, but, it looked surprisingly feminine, although it was flat. Perhaps her smooth shiny hairless skin and slightly perky nipples were all it took to be feminine.

She meanwhile was enjoying the conversation. And enjoying how uncomfortable I was.

She said, "Max, I love that we are friends. Dating is horrible. I have to now get ready and put on make up and hide this..." She looked down. I took that opportunity to look down, too. It was very fat and very long. I did not know that penises could be that big.

She looked up and saw me checking her out and said, "It's so cool that I can hang out and not hide this from you. If we were dating, you wouldn't be allowed to see this for a long time."

"Why?"

"Because I'm a girl, silly!"

"Oh."

"Yeah, I hate it. I wish it wasn't so big. I don't believe in hormones or surgery. But this is quite a challenge for me. If only it wasn't so damned big. Do you know that people have refused to have sex with me because of it? Guys and girls!"

"I'm sorry."

"It's okay."

I said, "It's a bit ironic, because a lot of guys would kill to be as hung as you."

"Yeah. I know. But what they don't know is that it reduces the amount of sex I can have when I'm in a relationship because people get sore. It definitely can attract some girls or guys. But it's unfortunately for kicks."

"Well, I think it's awesome. I'm sure someone lucky guy will be very satisfied."

She seemed happy about that and said, "You are so sweet." And went to give me a hug. I was a bit nervous. Her penis touched me and I was just wearing running shorts and a t-shirt so I had to maneuver around a bit. She pulled away.

Then she said, "But, I have to tell you, as a girl. I wish that my penis was just like yours. Then I'd be able to satisfy my lucky guy even more."

"How do you know what my penis looks like."

"I can tell. It's average. Just like I want."

I said, "I'm above average. But thanks."

She looked at my crotch carefully, "Really?"

I said, "There's a big different between what you've got and above average."

She said, gesturing to her penis and moving it a little bit, "Have you ever seen one as big?"

"No, as a matter of fact."

She smiled. I'll tell you what. If you want, because you seem a little bit impressed, just once, you can touch it. It'll be our little secret. I can see how curious you are."

"That's okay."

She smiled, "Don't be silly. Let's just get this out of our system. This will be good for our friendship. You'll never have to wonder and you'll be able to treat me like normal again."

"You're so funny, Joline."

She smiled, "Come on. After my date. I might be taken and then the chance will be gone forever. I'll be married with my white picket fence and you'll never get another chance." She was smiling at me, obviously having fun with how nervous I was. "Come." And she took my hand. I pulled back a little. But she held on and looked at me like I was an obstinate kid, and I relented.

She put my hand on her penis and I felt it and gave it a little squeeze. It got a little bigger. She was looking at me the whole time. She smiled mischievously when I held it. She then pulled my hand away, and said, "Okay, only for you Max." And continued to smile. It was starting to move and was getting even bigger.

She looked at me and said, "You are so nervous. It's so cute. I have to get ready though. But first let me give you a hug."

Then naked, she grabbed me and hugged me. Then she squeezed me again. "You are so nervous. I love it."

She was getting fairly hard. I could feel her penis through my running shorts all the way up my stomach. I realized this and pulled my midsection away. "Oops, I'm sorry. I guess I should've foreseen that from the feel." She smiled some more, still holding on to me. She was fun.

Now her monster was hard and I looked down and it was looking up at me. She smiled. I have to get ready for my date.

"We're good, right?" She asked.

"Sure."

"Oh wait one second. I just realized. We aren't done."

"Oh?"

"Yeah. You got to see and feel mine. But, I'm left here and will never get to see yours."

I said, "Okay and quickly flashed her."

She nodded her head and said, "Max" you know that wasn't fair. But, I'm late. I have to go. We'll have to talk about this later. She smiled.

Then she took her towel and went back to the bathroom and got ready.

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11 Comments
GrrrreatImaginationGrrrreatImaginationover 9 years ago
whew!

I was scared there for a minute that you didn't have the rest of the story, but I see you do. Thanks, by the way. It's disconcerting sometimes to find a really good story starter, only to discover that that's all there is. This one seems like it's a good one. I'd say more, but the story beckons.

AnonymousAnonymousabout 11 years ago
The way it should be

I am a T-girl and I want to be treated as a female in a relationship, to me this a friendship heading towards a relationship. A t-girl isn't any different than any other female as far as desires go. I like how she was described and that fact she was well hung. I am small in the penis department.

I hope to see this continue as it started smooth with out a sudden rush to please the readers.

Naughtyboy1986Naughtyboy1986over 11 years ago
a good start

A fun and playful beginning can't wait to read more

Omega ManOmega Manover 11 years ago
Next?

Tell us more ... we readers want to read more

AnonymousAnonymousover 11 years ago
greast story

I love it. Great start. I'm waiting for the next chapters.

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