Becoming a Gurl Pt. 01

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Saying yes to a date for starters.
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I'm 35 years old 5'6", 145 lbs, single and lonely. I've been a discreet, closeted cross-dresser, and alone, when I decided to give this adult dating site a try. I set up my profile and a few discreet, pictures without my face, and waited. Over the few months, I got some replies. Some replies were rather vulgar, and sharing dick picks with me, telling me they can't wait to fuck my pretty mouth and such. While I was turned on, I was scared to converse with these guys. Other responses did nothing for me, really.

During this time, my hours at work were being cut back. My money had gotten tighter. I was afraid of not being able to pay my rent. I was feeling more alone.

One day, I got an email from this guy Dwayne. It read, "Hi Michael. My name is Dwayne. I read your profile. I'm very interested in talking with you. I'm a good guy and very discreet, so no worries. Let me know when you are here again."

I then clicked on his profile. I was taken a little surprised. He had a face pick on his profile! Dark skinned man with a nice smile, wearing a suit and tie. I was intrigued. I read his stats and profile.

45 years old, 5'10", 190 lbs. Non-smoker, occasional drinker, bla bla bla. Then I read his cock size: 8 inches. My eyes opened a little more when I read that! But then I thought, people like to make up things.

I then read his profile. He wrote that he was a single, business manager, that lived alone. He wrote that he is very interested in cross-dressers and T-Gurls and would like to have a discreet roommate / relationship with a young discreet guy that wears girls clothes and is open minded. When I read that, I thought he seemed like a good guy, so nothing worrisome.

Dwayne had several other photo's on his profile. One was a picture of him wearing a man's tight boxer briefs. His upturned, confined cock looked big! He was obviously aroused when that picture was taken! Maybe what he had said about his cock being 8 inches WAS true!? I had to reply back to this guy! I was anxious and a little nervous!

A day later, back on that site, we found each other and went to a chat room. He said he was happy I replied back to him! At first, we typed back and forth about life and such. Then the conversation turned more personal with him asking me what I liked to wear and such. He assured me that he was very disceet. So, I shared that that I didn't wear girls clothes all the time, and mainly only wear panties and stockings and some satin pajama's.

He told me he very much liked me admitting those things about me because he was very much into CD's and T-gurls. He typed that he was aroused, thinking about me wearing sexy clothes for him! His words were getting me aroused too!

Our conversation back and forth became more sexual. He asked me if I liked to suck cock! I shyly typed back that I did! He asked me if I was a bottom gurl too! Again, I shyly typed back yes. He again, told me his cock was hard, hearing me say that! He added that he LOVES getting his cock sucked! He says he fantasizes about a guy that looked like a girl on her knees, sucking him, and that he was total Top!

Dwayne became more intimate in his words, telling me he can't wait to have sex with me.

"I want your pretty lips wrapped around my cock Michael."

"I'm going to fuck you and cum deep inside you. Once I do, you'll be MY Gurl. You want that, don't you!"

"Yes," I admitted.

"You want to be my gurl, don't you!" he coaxed.

"Yes," I again nervously answered.

"Then say yes. Say you'll become my gurl tonight!"

I was flustered! TONIGHT!!! I was extremely aroused by his forwardness! I didn't know how to respond to that. A minute went by before he typed, "Be a good girl and say yes! You know you want my cock!"

He was breaking me down. I nervously typed back, "I want too."

He wrote back, "Don't fight your feelings. Become my gurl, Michael. You know you want too."

I was so weak! This is what I came to this site for. He typed again...

"Come on baby. This was meant to be. You know it's true!"

I typed back, "Okay," and hit send.

"Good Gurl," he typed back.

I nervously gave him my address. He told me he'd pick me up at 8 p.m and told me to wear something pretty for him, under my guy clothes.

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MichaelfantasiesMichaelfantasiesabout 2 months agoAuthor

Hi everyone. I'm sorry I haven't yet posted part 2 on this story. I want too! I know it's been a while. I have a basic storyline about how the date will go on. I'm thinking Dwayne taking Michael to dinner and talking more about what Dwayne wants and about Michael's apprehensions, but that sounds boring, so after a nice night, a blowjob is necessary for Michael to perform - Thus a part 3 would have to happen. I'm also thinking about Dwayne coming on to Michael more purposefully and taking Michael (fucking him) before he's ready to commit to all of what Dwayne is expecting, i.e. wearing girls clothes 24/7; taking female hormones and such.

Readers, let me know how YOU'd like this story to lead into! Thanks. 🤔😎😯😀

AnonymousAnonymous9 months ago

Come on now, get part 2 finished. Can't wait to know all the juicy first date action!

88girfriend88girfriend10 months ago

Great start. Will Micheal be Michelle soon? I can't wait to find out.

pokeyridepokeyride10 months ago

I can't wait for the next chapter !!!!

AnonymousAnonymous10 months ago

Please continue I'd really like to know how things turn out. I'm like you, a shy nervous crossdresser and would really like to meet a kind caring guy

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