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.

And more...
 

So, my hand moved a bit more, uncovering part of my hard shaft...

And this arrived.

And even more...
 

And so my fingers parted... Leaving less to the imagination...

So she sent this.

And then...
 

I told her I needed to see her tits if she wanted to see more.

She was pleading not to have to.

"I've showed you a ton... I'm not going any further..."

But I knew she was dying over there.

"Want my hand to move away completely?" I typed.

"Hm... is that head glistening? I believe it is. You SHOULD see it."

Her reply was immediate.

"DON'T make me! PLEASE. PLEASE."

And I told her I was tracing my cock and ready to come all over the shadowy picture of her breasts.

"Except... I can't really see them that well. If you want to see me come, then turn on the lights. And bare them."

She protested. And protested more.

"I've never done this. Are you really going to make me?"

I turned on video chat, stood up, started to slowly move my hand away from my pre-come dick.

"I hate you," she typed.

And then sent this.

But that's not all...
 

"I told you to lose the shirt," I typed.

"NO!" came the immediate response. "I've done that for exactly ONE person -- and only in real life, not online -- and I'm married to him."

"The only way I'm coming is if I see all of you... And I'm SOOOOO close."

Fact of the matter is that I was. Barely holding on. My hand was a mess. And so I sent her a photo of that.

"You'll note that my hand is exhibiting evidence of how one bit of help from you will be magic... And that my hand is no longer covering anything."

And indeed, I was snapping away like mad. She would not be disapointed. And then took some bonus video. It was clear enough that you could see the throb of my heartbeat.

"ONE picture. ONE. And then the shirt goes back on."

"Sold," I replied.

"I can't believe I'm doing this" said the message on the screen. "I'm going to hell."

And then I saw that a file was loading...

And that picture was only half the story.
 

Half, I tell you.

So I wasn't done
 

As close as I was to coming, I wasn't letting her off the hook.

And turned on video chat again.

I traced my cock, letting glimpses peek through, but never revealing myself fully.

I know she could hear my ragged breath.

"If I come before I see you topless, you'll never see it. I'll turn off the computer and leave you aching. And i KNOW you don't want that!"

"BUT I'VE given you PLENTY! I told you that you were only getting one."

And so I turned off chat completely. Leaving her hanging.

Of course, on Facebook, even when chat is off, you still receive messages. She couldn't tell if I was there or not. But I got her message.

"If I show you, will you finally show me?"

I didn't answer.

"PLEASE?" came her next text.

Again I didn't answer.

And this picture appeared.

And then came the video
 

But I don't know if I'm allowed to post that in the photo threads.

Mods?

Here's the Rule... Really straight forward:

Awesome story, please upload in vid thread. Did you get her pussy?;)

Video
 

It's only 15 seconds of VERY shy nipple play.

But I will post that soon in a new thread.

That's on my agenda for tonight if all goes well.

It may take me moving that hand.

And then moving it some more. And more... And more...

Until I'm JUST about to come.

But I'm not sending that until I see her fully nude, looking me in the eye with her baby blues, while she shudders and moans.

Since you're not a "OnePass Member" I'd recommend that you post the video to Zippyshare (http://www.zippyshare.com/)
and post the link to it here. That way everyone can see it.

Mudbug

bonus bra and pantie pic
 

She really has to stop using the selfie cam on her phone.

I'm going to get her in front of the mirror so she uses the better front camera.

Yeah, mine has expired. That'll be taken care of again next week.

too bad...
 

there's no place to post the entire chat.

it'd be something to dump the whole thing with names blurred!

and thanks Mudbug!

love this. so amazing

Getting her attention
 

We'll forget about that vid for a little bit. I've been on the road a bit and not bothered to renew my account.

When I returned, I realized that I hadn't heard from Julie for awhile. She had been awfully shy since the nipple play. And despite casting a few Facebook messages, I hadn't gotten a nibble.

So, on a slow day at work, I went into the washroom off my office -- I'm lucky enough to have my own john off the main part of my office. And an office door that locks.

Anyhow, I aimed the phone at the mirror -- showing just below my face and down -- and peeled off my shirt. And then unbuttoned the top button of my butterfly jeans.

Without typing a word, I sent it.

And she immediately appeared online.

"Keep going," she typed.

I started filming again, holding up my iPad, which had the picture of her tits up on it, and placing it on the sink in front of me, visible to her. Then I unbuttoned the rest of the buttonflys.

"I'm going to come all over you," I typed.

"Keep going!!!" she responded.

Pointing my phone, I peeled my jeans down. It was obvious what kind of condition I was in. As they fell to the floor, my boxer briefs showed a VERY hard outline.

"Fucking HOT!" It took less than a second for her to respond. "Are those coming off?!?!"

"Depends..." I was smirking as I typed. "On what you do."

"UH UH! NOPE! Not this time!" flashed her message. "I already showed WAY too much last time."

And so I aimed the camera again, slowly teasing the waistband of my shorts, pulling them down the shaft of my cock, and then back up again. Lower. Lower... And then just hiding the head and preventing it from escaping in hardened excitement before stopping the video."

"If you want these shorts to go, you really need to be nude." Knowing she was itching, I added: "You've got 3 minutes before I leave."

There was chat silence for a good 2 minutes and 59 seconds before the following arrived.

What
 

But she wasn't naked yet
 

"I can't help but notice you're not naked yet," I noted.

"I can't," she responded.

"I beg to differ."

And filmed the shorts being pulled down and my hard dick bouncing out -- a brief flash before I covered up with my hand. Even then, she could see the head poking out between two fingers.

"How bad do you want to see me come all over you?

Which was when the panty shot arrived.

"Fuck this shit," I quickly responded. "You've teased enough. I'm going to go do some work."

"Promise you won't make me go further?"

"Ha." I responded. "Not until I watch you come. But if you get naked, then I will to. And for god's sake, turn on the light!"

And the panties disappeared.

(I think this is safe for here. No penetration.)

It took a bit more
 

"Well, you're getting there," I typed. "And you probably deserve this."

My shorts had been pulled back up, but I filmed a great deal more tease pulling them down. This time I let my penis bob free as the shorts slid down. And I was was nude. Visible from the chin down. And throbbing.

"Pay up and I'll come all over you. Or at least your tits on my iPad."

"What do you need to see?" she asked.

"You," I replied. "Head. To. Toe."

"I don't do that," she answered. "I won't do that."

"You will if you want this to continue."

"WHY CAN"T YOU JUST SEND?!?!?"

"Because I know this is torture for you," I noted. "And that is fucking hot. But buck up or I'm gone."

"It IS torture!"

"5..." I typed. "4... 3... 2..."

And an image appeared.

And then another.

needless to say...
 

I won't go too far into detail about what I had to do next... Sufficed to say that while she watched me slowly tease, tug, and trace myself to the point where I was about to come, a few more pictures came in.

Each time with a bit less complaint. Her resolve finally breaking.

She kept on asking to watch me come. But I held on to that footage.

There were limits that she kept on putting up. And I'm keeping my bargaining chip. Both of us came hard. And (I'm willing to bet) we both have footage.

And THAT it what will come next, I hope.

fairly similar from what i can tell.

Great
 

This is great hopefully you will be able to get s picture of her arse and head to toe naked well played sir

Any more luck?
 

Any more luck?

It's a start, Keep me informed!
 

It is a start and things will improve for you.
Keep posting as I'm CURIOUS TO SEE THIS CHICK NUDE!

congrats to you! There are plenty girls from the past I would love to see nude.