A Girl From High School I'm FINALLY Seeing Naked
 

There was a girl I used to mess around with in high school. Every few months we'd end up drunk/high and frisky. The funny thing is that, although I tried my best, I could never get her out of her clothes. She was shy -- still is -- and very hard to get. Despite several make-out sessions, only my hands -- and not my eyes -- ever got a chance to explore beneath her bra and underwear.

A few months ago -- and years later -- I started chatting with her online. I told her about a "dream" that I had -- and she started getting turned on. By chatting and complimenting, I finally got her to loosen up.

And what do you know? Her clothes have started loosening up too! ;)

I've finally ALMOST got her naked.

But it has been slow going.

This is as far as I got her on our first chat. She is PAINFULLY shy. And thinks she's too heavy. But I've started getting her top off. And her bra. She's dying to see more of me -- and to have me offer my oh-so-delicious words -- and has told me that, soon, she will bare all.

We'll see! ;)

It took to chat #4 to get this far
 

Did I mention shy?

I had to make her come 4 times before I got this.

And, I think, 6 before I really got a view.

good luck!!!

How old are we talking about.

Good start!

You'll see soon!

Late 30's now.

After that post, she became super-reluctant. She sure didn't mind me shedding clothes. And she was starting to get a bit bolder with her side of the chat, but she wasn't willing to send photos.

So, by post 6, I told her I wasn't going any further until she gave me some skin.

Her husband was downstairs, and she didn't want to turn on the light -- she was claiming to be asleep.

It was dark, but she finally got back down to her bra... "That's all you're getting," she typed.

But I knew I had her hooked.

By this point she was super worked up and wanted me to send her a picture of me nude.

But I told her it would cost her first.

"Lose the bra, Julie."

She protested. And protested. And protested.

"You're killing me!" she exclaimed.

"And I love it," I replied. "But you're not getting another peek -- or another word -- until you up the ante."

Which was when the next image came in.

The bra was gone, but...

After that, I decided to hit the open the audio on our chat.

Again, she was reluctant. But when she did, I could tell by the sound of her voice that she was very, VERY aroused. Distracted, breathy...

She wouldn't open a video chat though. Which was too bad.

"I want to see you!" she said again. There was a bit of pleading to her voice and I knew she wanted to finish herself off.

"Then move your arm," I smiled.

And the final picture of the night came though.

I replied with the photo I had waiting and the audio went dead.

She was too shy to let herself be heard as she came.

Nice one, and thanks for the detailed story.

Hopefully you can get more out of her :p

Some progress...
 

Last night she messaged me and told me she wanted to see me come. Bashful, but horny.

And so I sent her a picture where my hand just barely concealed some of my erection.

I told her that my hand would slowly inch away if she showed me what she was doing to herself.

And this picture came in.